(8S,9S,13S,14R)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

Details

• Internal ID: 5ed74d6f-0920-4e21-a567-b8b3273a4cc5
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Estrane steroids > Estrogens and derivatives
• IUPAC Name: (8S,9S,13S,14R)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• SMILES (Canonical): CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)O
• SMILES (Isomeric): C[C@]12CC[C@H]3[C@@H]([C@H]1CCC2=O)CCC4=C3C=CC(=C4)O
• InChI: InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15+,16-,18+/m1/s1
• InChI Key: DNXHEGUUPJUMQT-HPFXQQBRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₂
• Molecular Weight: 270.40 g/mol
• Exact Mass: 270.161979940 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.82
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7753	77.53%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7882	78.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9753	97.53%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.7750	77.50%
BSEP inhibitior	-	0.7221	72.21%
P-glycoprotein inhibitior	-	0.9167	91.67%
P-glycoprotein substrate	-	0.6988	69.88%
CYP3A4 substrate	+	0.6957	69.57%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.7000	70.00%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9353	93.53%
CYP2C19 inhibition	-	0.8954	89.54%
CYP2D6 inhibition	-	0.9599	95.99%
CYP1A2 inhibition	+	0.9017	90.17%
CYP2C8 inhibition	+	0.9412	94.12%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7600	76.00%
Carcinogenicity (trinary)	Non-required	0.3609	36.09%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9584	95.84%
Skin irritation	+	0.6660	66.60%
Skin corrosion	-	0.9023	90.23%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7459	74.59%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.9435	94.35%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	III	0.7811	78.11%
Estrogen receptor binding	+	0.9287	92.87%
Androgen receptor binding	+	0.8695	86.95%
Thyroid receptor binding	+	0.7772	77.72%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	-	0.5378	53.78%
Honey bee toxicity	-	0.8981	89.81%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9907	99.07%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	199.5 nM	Potency	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	1.3 nM	Potency	via Super-PRED
CHEMBL3181	P14061	Estradiol 17-beta-dehydrogenase 1	109 nM	IC50	via Super-PRED
CHEMBL206	P03372	Estrogen receptor alpha	7 nM	EC50	via Super-PRED
CHEMBL242	Q92731	Estrogen receptor beta	8 nM	EC50	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	15.8 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	11.2 nM	Potency	via Super-PRED
CHEMBL3305	P04278	Testis-specific androgen-binding protein	6.607 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	98.11%	91.11%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	97.84%	89.05%
CHEMBL2581	P07339	Cathepsin D	93.63%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.49%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.91%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.29%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.10%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.09%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.81%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.76%	97.25%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	88.03%	97.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.15%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.00%	90.71%
CHEMBL217	P14416	Dopamine D2 receptor	84.73%	95.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.01%	93.40%
CHEMBL1937	Q92769	Histone deacetylase 2	82.58%	94.75%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.41%	100.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.14%	85.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.19%	100.00%

Plants that contains it

• Aconitum maximum
• Aconitum vilmorinianum
• Actinidia kolomikta
• Aglaia elaeagnoidea
• Aristolochia littoralis
• Astragalus gummifer
• Boronia koniambiensis
• Canarium strictum
• Cardiospermum halicacabum
• Centaurea nigrescens
• Cirsium japonicum
• Coreopsis fasciculata
• Coreopsis grandiflora
• Crepis foetida
• Crinum viviparum
• Cuphea carthagenensis
• Dioscoreophyllum cumminsii
• Dipteronia dyeriana
• Dodonaea polyandra
• Dorstenia lindeniana
• Erigeron canadensis
• Euphorbia segetalis
• Garcinia celebica
• Garcinia macrophylla
• Gymnanthemum amygdalinum
• Gymnosporia serrata
• Hyphaene thebaica
• Maytenus loeseneri
• Murraya kwangsiensis
• Odontites vulgaris
• Olea europaea
• Ongokea gore
• Ophiorrhiza blumeana
• Ozoroa insignis
• Parastrephia lepidophylla
• Penstemon secundiflorus
• Peucedanum palustre
• Phalaenopsis aphrodite
• Phedimus kamtschaticus
• Phlogacanthus thyrsiformis
• Physalis solanaceus
• Phytolacca acinosa
• Piper arboreum
• Plectranthus mollis
• Podocarpus salignus
• Pouzolzia occidentalis
• Prosopis ruscifolia
• Prunus armeniaca
• Psychotria bahiensis
• Punica granatum
• Ruta microcarpa
• Schistostephium rotundifolium
• Selinum carvifolium
• Sidastrum multiflorum
• Sideritis syriaca
• Siphocampylus verticillatus
• Syncolostemon parviflorus
• Thuja plicata
• Triglochin maritima
• Urtica triangularis
• Vepris pilosa
• Veratrum shanense
• Viburnum chingii
• Zanthoxylum melanostictum
• Zanthoxylum schreberi

Cross-Links

• PubChem: 670995
• NPASS: NPC144109
• LOTUS: LTS0031044
• wikiData: Q104985822