Procyanidin A2

Details

• Internal ID: 53d983ef-a682-450b-981f-d1f96108b4f3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC3=C2C4C(C(O3)(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O)C7=CC(=C(C=C7)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=C1C(=CC3=C2[C@@H]4[C@H]([C@](O3)(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O)C7=CC(=C(C=C7)O)O)O
• InChI: InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1
• InChI Key: NSEWTSAADLNHNH-LSBOWGMISA-N
• Popularity: 127 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₄O₁₂
• Molecular Weight: 576.50 g/mol
• Exact Mass: 576.12677620 g/mol
• Topological Polar Surface Area (TPSA): 210.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 12
• H-Bond Donor: 9
• Rotatable Bonds: 2

Synonyms

• Procyanidin A2
• 41743-41-3
• Proanthocyanidin A-2
• Procyanidol A2
• Procyanidoepicatechin
• UQN6668Q4R
• Procyanidin dimer A2
• CHEBI:28472
• Epicatechin-(2beta->7,4beta->8)-epicatechin
• CHEMBL286933
• (2r,3r,8s,14r,15r)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-2h,14h-8,14-methanochromeno[7,8-d][1,3]benzodioxocine-3,5,11,13,15-pentol
• LITCHIDERM LS-9704 COMPONENT
• (+)-Proanthocyanidin A2
• (1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
• Dimeric catechin
• (+)-Epicatechin-(4.beta.-8,2.beta.-O-7)-epicatechin
• PROCYANIDINA2
• bis(3,4-dihydroxyphenyl)[?]pentol
• 2,14-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-8,14-methano-2H,8H,14H-1-benzopyrano(8,7-c)(1,5)benzodioxocin-3,5,9,11,15-pentol
• 8,14-METHANO-2H,14H-1-BENZOPYRANO(7,8-D)(1,3)BENZODIOXOCIN-3,5,11,13,15-PENTOL, 2,8-BIS(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R,3R,8S,14R,15R)-
• 8,14-Methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R,8S,14R,15R)-
• UNII-UQN6668Q4R
• SCHEMBL981582
• DTXSID00904175
• Procyanidin A2, analytical standard
• BDBM50478905
• C30H24O12
• EC-(4b,8)(2b,7)-EC
• AKOS037514797
• AC-35008
• Epicatechin-(2b->7,4b->8)-epicatechin
• MS-30365
• A903788
• Q7247550
• (+)-EPICATECHIN-(4beta-8,2beta-O-7)-EPICATECHIN
• Epicatechin-(4.beta.-->8,2.beta.-->O-->7)epicatechin
• PROANTHOCYANIDIN A2;PROCYANIDIN A2; PROCYANIDOEPICATECHIN
• 8,14-Methano-2H,14H-1,7,9-trioxabenzo[6,7]cycloocta[1,2-a]naphthalene-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R,8S,14R,15R)-
• 8,14-Methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, [2R-(2.alpha,3.alpha.,8.beta.,14.beta.,15R*)]-
• 8,14-Methano-2H,8H,14H-1-benzopyrano(8,7-c)(1,5)benzodioxocin-3,5,9,11,15-pentol, 2,14-bis(3,4-dihydroxyphenyl)-3,4-dihydro-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7002	70.02%
Caco-2	-	0.8957	89.57%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5149	51.49%
OATP2B1 inhibitior	-	0.5655	56.55%
OATP1B1 inhibitior	+	0.9133	91.33%
OATP1B3 inhibitior	+	0.8374	83.74%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9320	93.20%
P-glycoprotein inhibitior	+	0.7152	71.52%
P-glycoprotein substrate	-	0.7386	73.86%
CYP3A4 substrate	+	0.6247	62.47%
CYP2C9 substrate	-	0.7965	79.65%
CYP2D6 substrate	+	0.3672	36.72%
CYP3A4 inhibition	-	0.9095	90.95%
CYP2C9 inhibition	-	0.8939	89.39%
CYP2C19 inhibition	-	0.8571	85.71%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.9758	97.58%
CYP2C8 inhibition	+	0.7468	74.68%
CYP inhibitory promiscuity	-	0.9554	95.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6019	60.19%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8118	81.18%
Skin irritation	-	0.6303	63.03%
Skin corrosion	-	0.9314	93.14%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8853	88.53%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8144	81.44%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4799	47.99%
Acute Oral Toxicity (c)	IV	0.5178	51.78%
Estrogen receptor binding	+	0.7781	77.81%
Androgen receptor binding	+	0.8055	80.55%
Thyroid receptor binding	+	0.6647	66.47%
Glucocorticoid receptor binding	+	0.6738	67.38%
Aromatase binding	+	0.5579	55.79%
PPAR gamma	+	0.7312	73.12%
Honey bee toxicity	-	0.6521	65.21%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.7943	79.43%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1697671	P49763	Placenta growth factor	394 nM	Kd	via Super-PRED
CHEMBL1783	P15692	Vascular endothelial growth factor A	476 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.57%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.21%	91.49%
CHEMBL233	P35372	Mu opioid receptor	94.99%	97.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.82%	96.09%
CHEMBL236	P41143	Delta opioid receptor	91.91%	99.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.49%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.94%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.48%	93.40%
CHEMBL2581	P07339	Cathepsin D	89.21%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.11%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.21%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.56%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.79%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.84%	94.62%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.69%	85.11%

Plants that contains it

• Aconitum liangshanicum
• Aconitum sachalinense
• Aesculus hippocastanum
• Ageratina gracilis
• Aizoon africanum
• Alangium premnifolium
• Alstonia deplanchei
• Angelica tarokoensis
• Arachis hypogaea
• Aster bellidiastrum
• Asteriscus graveolens
• Baccharis megapotamica
• Bombax ceiba
• Caragana halodendron
• Centrosema pascuorum
• Ceratiola ericoides
• Ceratozamia fuscoviridis
• Cinchona pubescens
• Cinnamomum bejolghota
• Citrus glauca
• Crataegus sinaica
• Critonia quadrangularis
• Cupania latifolia
• Davallia divaricata
• Dimocarpus longan
• Diospyros ferrea
• Dolomiaea souliei
• Epimedium davidii
• Erysimum odoratum
• Eucalyptus camaldulensis
• Ficus simplicissima
• Flemingia macrophylla
• Frullania tamarisci
• Garcinia mangostana
• Globba variabilis
• Gynura bicolor
• Haplophyllum dauricum
• Heterotheca inuloides
• Hypericum perforatum
• Ilex amara
• Isodon japonicus
• Ixora coccinea
• Knightia excelsa
• Lasiosiphon lampranthus
• Leonurus glaucescens
• Lepidium draba
• Ligularia vellerea
• Litchi chinensis
• Lonicera hypoleuca
• Marrubium supinum
• Metalasia capitata
• Micromeria pineolens
• Nicotiana sylvestris
• Orthosphenia mexicana
• Oxyanthus speciosus
• Paullinia cupana
• Pavetta owariensis
• Quercus dentata
• Quercus petraea subsp. petraea
• Rheum tanguticum
• Rhynchopsidium pumilum
• Rumex acetosa
• Salacia madagascariensis
• Saussurea lyrata
• Senecio latifolius
• Senecio peripotamus
• Serpocaulon triseriale
• Solanum acaule
• Solanum elaeagnifolium
• Stevia mercedensis
• Strychnos tabascana
• Styrax hookeri
• Swertia delavayi
• Swinglea glutinosa
• Tainia bicornis
• Theobroma cacao
• Thuja standishii
• Urceola laevigata
• Urceola micrantha
• Vaccinium vitis-idaea
• Vepris hiernii
• Verbesina rupestris
• Vismia jefensis

Cross-Links

• PubChem: 124025
• NPASS: NPC272552
• ChEMBL: CHEMBL286933
• LOTUS: LTS0117726
• wikiData: Q7247550