Hennadiol

Details

• Internal ID: 7c13ea9c-d91e-4721-a4d4-1664076db88a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-(3-hydroxyprop-1-en-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1O)C)CCC4C3(CCC5(C4C(CC5)C(=C)CO)C)C)C)C
• SMILES (Isomeric): C[C@]12CC[C@H]([C@@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C(=C)CO
• InChI: InChI=1S/C30H50O2/c1-19(18-31)20-10-13-27(4)16-17-29(6)21(25(20)27)8-9-23-28(5)14-12-24(32)26(2,3)22(28)11-15-30(23,29)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1
• InChI Key: ZNUAKACHFYTNFX-QGTGJCAVSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₂
• Molecular Weight: 442.70 g/mol
• Exact Mass: 442.381080833 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 8.60
• Atomic LogP (AlogP): 7.00
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 30-Hydroxylupeol
• 20065-99-0
• (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-(3-hydroxyprop-1-en-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
• 29-hydroxylupeol
• (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-[1-(hydroxymethyl)vinyl]-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
• CHEMBL518390
• AKOS040761829
• Lup-20(29)-ene-3.beta.,30-diol
• (1R,3aR,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-(1-Hydroxymethyl-vinyl)-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	-	0.5654	56.54%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.4831	48.31%
OATP2B1 inhibitior	-	0.5799	57.99%
OATP1B1 inhibitior	+	0.9285	92.85%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6385	63.85%
BSEP inhibitior	+	0.6926	69.26%
P-glycoprotein inhibitior	-	0.7977	79.77%
P-glycoprotein substrate	-	0.8376	83.76%
CYP3A4 substrate	+	0.6837	68.37%
CYP2C9 substrate	-	0.6284	62.84%
CYP2D6 substrate	-	0.7222	72.22%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9297	92.97%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.5882	58.82%
CYP inhibitory promiscuity	-	0.6441	64.41%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6609	66.09%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9182	91.82%
Skin irritation	-	0.6073	60.73%
Skin corrosion	-	0.9611	96.11%
Ames mutagenesis	-	0.7570	75.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6457	64.57%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.6442	64.42%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.5702	57.02%
Acute Oral Toxicity (c)	III	0.7441	74.41%
Estrogen receptor binding	+	0.7464	74.64%
Androgen receptor binding	+	0.7798	77.98%
Thyroid receptor binding	+	0.6047	60.47%
Glucocorticoid receptor binding	+	0.8125	81.25%
Aromatase binding	+	0.7346	73.46%
PPAR gamma	+	0.5492	54.92%
Honey bee toxicity	-	0.7060	70.60%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9839	98.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL204	P00734	Thrombin	93.66%	96.01%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.88%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.11%	96.09%
CHEMBL233	P35372	Mu opioid receptor	90.98%	97.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.52%	94.45%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	90.22%	95.42%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.24%	97.25%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.53%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.42%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.40%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.30%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.85%	92.94%
CHEMBL206	P03372	Estrogen receptor alpha	87.30%	97.64%
CHEMBL1937	Q92769	Histone deacetylase 2	86.23%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.62%	95.89%
CHEMBL237	P41145	Kappa opioid receptor	85.12%	98.10%
CHEMBL2996	Q05655	Protein kinase C delta	84.91%	97.79%
CHEMBL2581	P07339	Cathepsin D	84.50%	98.95%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.86%	85.49%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.69%	96.95%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.42%	91.03%

Plants that contains it

• Abutilon grandiflorum
• Adenopeltis serrata
• Aniba parviflora
• Astragalus pamirensis
• Beaumontia brevituba
• Bituminaria bituminosa
• Cajanus cajan
• Cassipourea madagascariensis
• Celastrus hypoleucus
• Centaurea hololeuca
• Centaurea seridis
• Ceriops decandra
• Chisocheton cumingianus subsp. balansae
• Chrozophora tinctoria
• Cneorum pulverulentum
• Coccinia grandis
• Cratoxylum arborescens
• Cyclolepis genistoides
• Dalbergia stipulacea
• Daphne oleoides
• Delphinium ajacis
• Elaeagnus commutata
• Elaeodendron croceum
• Eucalyptus flocktoniae
• Euonymus carnosus
• Euphorbia chamaesyce
• Euphorbia humifusa
• Euphorbia kopetdaghi
• Flindersia brayleyana
• Flourensia heterolepis
• Gymnema sylvestre
• Heracleum sphondylium
• Ipomoea muelleri
• Iryanthera juruensis
• Jungermannia obovata
• Kummerowia striata
• Lawsonia inermis
• Liabum bourgeaui
• Lychnophora pseudovillosissima
• Lychnophora rupestris
• Lydenburgia cassinoides
• Maerua oblongifolia
• Mandragora officinarum
• Mascarenhasia arborescens
• Meconopsis napaulensis
• Merremia umbellata
• Microtropis fokienensis
• Millettia conraui
• Nuxia sphaerocephala
• Palafoxia rosea
• Pedicularis condensata
• Peperomia heyneana
• Perityle vaseyi
• Perrottetia arisanensis
• Phoebe formosana
• Piloselloides hirsuta
• Plectranthus barbatus var. barbatus
• Plectranthus garckeanus
• Pluchea sericea
• Porella swartziana
• Prunus japonica
• Quercus mongolica
• Quercus variabilis
• Reissantia indica
• Rheum webbianum
• Rohdea wattii
• Salacia chinensis
• Salvia coulteri
• Sanguisorba minor
• Satureja cuneifolia
• Senecio flavus
• Sida cordifolia
• Sinocrassula indica
• Solanum sisymbriifolium
• Thapsia transtagana
• Thryptomene kochii
• Thymbra spicata
• Tolpis webbii
• Toxicopueraria peduncularis
• Turraeanthus mannii
• Uncaria lancifolia
• Valeriana cardamines
• Viburnum rhytidophyllum

Cross-Links

• PubChem: 489919
• NPASS: NPC248830
• LOTUS: LTS0182745
• wikiData: Q104389627