Procyanidin B2, (+)-

Details

• Internal ID: aac209f7-8866-445d-aef1-f9ba3eedb754
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=C1C(=CC(=C2[C@@H]3[C@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• InChI: InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29-/m1/s1
• InChI Key: XFZJEEAOWLFHDH-NFJBMHMQSA-N
• Popularity: 788 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₆O₁₂
• Molecular Weight: 578.50 g/mol
• Exact Mass: 578.14242626 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.00
• H-Bond Acceptor: 12
• H-Bond Donor: 10
• Rotatable Bonds: 3

Synonyms

• 29106-49-8
• Procyanidol B2
• Proanthocyanidin B2
• (+)-Procyanidin B2
• Procyanidin B-2
• CHEBI:75632
• 2,3-cis-proanthocyanidin
• UNII-L88HKE854X
• L88HKE854X
• EC-(4b,8)-EC
• Epicathechin-(4beta->8)-epicathechin
• NSC 623097
• PROCYANIDIN B2 DIMER
• CHEMBL38714
• PROCYANIDIN B2, (+)-
• NSC-623097
• (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• [4,8'-Bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R,2'R,3R,3'R,4R)-
• (2R-(2alpha,3alpha,4beta(2'R*,3'R*)))-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-(4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol
• (4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R-(2alpha,3alpha,4beta(2'R*,3'R*)))-
• PROCYANIDIN B2 (USP-RS)
• PROCYANIDIN B2 [USP-RS]
• (2R,2'R,3R,3'R,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol
• (4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL, 2,2'-BIS(3,4-DIHYDROXYPHENYL)-3,3',4,4'-TETRAHYDRO-, (2R,2'R,3R,3'R,4R)-
• PROCYANIDINB2
• Procyanidin-B2
• C30-H26-O12
• Procyanidin dimer B2
• SCHEMBL288579
• XFZJEEAOWLFHDH-NFJBMHMQSA-N
• DTXSID701028797
• HY-N0796
• Procyanidin B2, analytical standard
• BDBM50553253
• LMPK12030002
• MFCD01861513
• AKOS008901339
• CS-5982
• BS-49221
• 4,8″-Bi-[(+)-epicatechin], cis
• C17639
• (-)-Epicatechin-(4.beta.-8)-(-)-epicatechin
• A912693
• J-017393
• Q7247552
• (-)-EPICATECHIN-(4beta->8)-(-)-EPICATECHIN
• (-)-EPICATECHIN-(4.BETA.->8)-(-)-EPICATECHIN
• cis,cis"-4,8"-Bi(3,3',4',5,7-pentahydroxyflavane)
• cis″-4,8″-Bi(3,3',4',5,7-pentahydroxyflavane)
• PROCYANIDIN B2 (CONSTITUENT OF GRAPE SEEDS OLIGOMERIC PROANTHOCYANIDINS)
• (2R,2'R,3R,3'R,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichromane]-3,3',5,5',7,7'-hexaol
• (2R,2'R,3R,3'R,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-4,8'-bichroman-3,3',5,5',7,7'-hexol
• (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]chromane-3,5,7-triol
• (2R-(2.ALPHA.,3.ALPHA.,4.BETA.(2'R*,3'R*)))-2,2'-BIS(3,4-DIHYDROXYPHENYL)-3,3',4,4'-TETRAHYDRO-(4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL
• (4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL, 2,2'-BIS(3,4-DIHYDROXYPHENYL)-3,3',4,4'-TETRAHYDRO-, (2R-(2.ALPHA.,3.ALPHA.,4.BETA.(2'R*,3'R*)))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8698	86.98%
Caco-2	-	0.9107	91.07%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4793	47.93%
OATP2B1 inhibitior	-	0.5605	56.05%
OATP1B1 inhibitior	+	0.9408	94.08%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9057	90.57%
P-glycoprotein inhibitior	+	0.6991	69.91%
P-glycoprotein substrate	-	0.8066	80.66%
CYP3A4 substrate	+	0.5743	57.43%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	+	0.5264	52.64%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9155	91.55%
CYP2C8 inhibition	+	0.6770	67.70%
CYP inhibitory promiscuity	-	0.8625	86.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6139	61.39%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8204	82.04%
Skin irritation	-	0.6044	60.44%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8993	89.93%
Micronuclear	+	0.7859	78.59%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.7665	76.65%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6052	60.52%
Acute Oral Toxicity (c)	IV	0.5696	56.96%
Estrogen receptor binding	+	0.7555	75.55%
Androgen receptor binding	+	0.7545	75.45%
Thyroid receptor binding	+	0.6710	67.10%
Glucocorticoid receptor binding	+	0.5949	59.49%
Aromatase binding	-	0.5919	59.19%
PPAR gamma	+	0.7488	74.88%
Honey bee toxicity	-	0.7797	77.97%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.6855	68.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.52%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.87%	83.82%
CHEMBL1951	P21397	Monoamine oxidase A	96.88%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.71%	96.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.59%	96.12%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.66%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.86%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.20%	99.15%
CHEMBL2535	P11166	Glucose transporter	86.62%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.17%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.92%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	84.40%	94.73%
CHEMBL3194	P02766	Transthyretin	83.39%	90.71%
CHEMBL236	P41143	Delta opioid receptor	83.31%	99.35%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.46%	94.45%

Plants that contains it

• Abies lasiocarpa var. lasiocarpa
• Acacia adunca
• Aconitum liangshanicum
• Aconitum sachalinense
• Acrotrema uniflorum
• Actinidia chinensis
• Adiantum philippense
• Aesculus hippocastanum
• Ageratina gracilis
• Albizia lebbeck
• Alcea rosea
• Aldama incana
• Alhagi sparsifolia
• Alkanna cappadocica
• Alpinia roxburghii
• Alstonia deplanchei
• Annona cornifolia
• Apocynum venetum
• Arachis hypogaea
• Areca catechu
• Artemisia pedemontana subsp. assoana
• Artemisia rupestris subsp. rupestris
• Aster bellidiastrum
• Asteriscus graveolens
• Astragalus sempervirens
• Atalantia racemosa
• Averrhoa carambola
• Baccharis megapotamica
• Balanops australiana
• Banisteriopsis caapi
• Begonia fagifolia
• Buddleja cordata
• Calluna vulgaris
• Calostephane divaricata
• Camellia reticulata
• Camellia sinensis
• Campylotropis hirtella
• Caragana aurantiaca
• Caragana halodendron
• Cassia fistula
• Cecropia glaziovii
• Centrosema pascuorum
• Ceratozamia fuscoviridis
• Chaenomeles sinensis
• Chaenomeles speciosa
• Cinchona pubescens
• Cinnamomum aromaticum
• Cinnamomum bejolghota
• Cinnamomum burmanni
• Cinnamomum camphora
• Cinnamomum verum
• Citrus glauca
• Cola nitida
• Coleogyne ramosissima
• Crambe tatarica
• Crataegus laevigata
• Crataegus monogyna
• Crataegus pinnatifida
• Crataegus sinaica
• Critonia quadrangularis
• Croton lechleri
• Cryptocarya obovata
• Curarea candicans
• Cynomorium coccineum subsp. songaricum
• Davallia divaricata
• Davallia perdurans
• Dimocarpus longan
• Dioscorea cirrhosa
• Diospyros eriantha
• Dolomiaea souliei
• Dumortiera hirsuta
• Echeveria secunda
• Eriobotrya japonica
• Eucalyptus camaldulensis
• Eucalyptus melliodora
• Euonymus tingens
• Euphorbia cornigera
• Fagopyrum acutatum
• Fagopyrum esculentum
• Ficus simplicissima
• Flemingia macrophylla
• Fragaria vesca
• Fritillaria monantha
• Garcinia mangostana
• Gentianella germanica
• Geranium sanguineum
• Gnetum latifolium
• Goniothalamus malayanus
• Gonzalezia decurrens
• Griselinia littoralis
• Guazuma ulmifolia
• Gymnosporia senegalensis
• Gynura bicolor
• Haplophyllum dauricum
• Hedysarum inundatum
• Helietta apiculata
• Hoffmannia strigillosa
• Houttuynia cordata
• Humulus lupulus
• Hylocomium splendens
• Hypericum erectum
• Hypericum japonicum
• Hypericum laricifolium
• Hypericum perforatum
• Ipomoea digitata
• Iryanthera megistophylla
• Juniperus sabina
• Kandelia candel
• Kokoona reflexa
• Larix gmelinii
• Laurus nobilis
• Lepisorus ussuriensis
• Ligularia vellerea
• Lindera umbellata
• Lonicera hypoleuca
• Lotus corniculatus
• Lotus pedunculatus
• Lysimachia mauritiana
• Maesa ramentacea
• Malus domestica
• Malus pumila
• Malus sylvestris
• Marrubium anisodon
• Marrubium supinum
• Melilotus tauricus
• Mespilus germanica
• Metalasia capitata
• Millettia erythrocalyx
• Millettia laurentii
• Monodora tenuifolia
• Myrsine lancifolia
• Naucleopsis ternstroemiiflora
• Nelia pillansii
• Nelumbo nucifera
• Neolitsea cassia
• Nicotiana sylvestris
• Ocimum tenuiflorum
• Ocotea pittieri
• Ononis vaginalis
• Orthosphenia mexicana
• Oxyanthus speciosus
• Pastinaca sativa
• Paullinia cupana
• Peltostigma guatemalense
• Phaseolus vulgaris
• Pinus strobus
• Pinus sylvestris
• Platanus orientalis
• Pluchea odorata
• Premna odorata
• Prunus dulcis
• Pseudotsuga menziesii
• Psidium guajava
• Psorospermum febrifugum
• Pteris semipinnata
• Quercus dentata
• Rauvolfia vomitoria
• Reynoutria multiflora
• Rheum tanguticum
• Rhizophora stylosa
• Rhodanthe chlorocephala subsp. rosea
• Rhynchopsidium pumilum
• Rubus chamaemorus
• Rumex acetosa
• Rumex maritimus
• Salacia lehmbachii
• Salvia hispanica
• Salvia syriaca
• Salvia yosgadensis
• Saraca asoca
• Saxifraga stolonifera
• Scorzonera pseudodivaricata
• Scutellaria amoena
• Senecio latifolius
• Senecio peripotamus
• Serpocaulon triseriale
• Sideritis brevibracteata
• Sideroxylon cubense
• Sideroxylon inerme
• Solanum elaeagnifolium
• Solanum laxum
• Spatholobus suberectus
• Spirotropis longifolia
• Stenocereus griseus
• Stevia aristata
• Stevia mercedensis
• Strychnos tabascana
• Styrax hookeri
• Swertia franchetiana
• Swinglea glutinosa
• Syncarpia hillii
• Taxus mairei
• Theobroma cacao
• Thuja standishii
• Thujopsis dolabrata
• Trichilia catigua
• Uncaria gambir
• Uncaria macrophylla
• Uncaria rhynchophylla
• Uncaria sinensis
• Urceola micrantha
• Vaccinium macrocarpon
• Vaccinium oxycoccos
• Vaccinium vitis-idaea
• Verbesina rupestris
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum
• Ziziphus jujuba
• Ziziphus lotus

Cross-Links

• PubChem: 122738
• NPASS: NPC236202
• ChEMBL: CHEMBL38714
• LOTUS: LTS0135510
• wikiData: Q7247552