Ingredient Details :(2S,3R,5R,9R,10R,13R,14S,16S,17R)-17-[(2R,3R)-2,3-dihydroxy-5,6-dimethylheptan-2-yl]-2,3,14,16-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one


TCMI-ID: TCMI18326


Physicochemical Property
Ingredient Name (2S,3R,5R,9R,10R,13R,14S,16S,17R)-17-[(2R,3R)-2,3-dihydroxy-5,6-dimethylheptan-2-yl]-2,3,14,16-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Pubchem CID 44449996
Iupac name (2S,3R,5R,9R,10R,13R,14S,16S,17R)-17-[(2R,3R)-2,3-dihydroxy-5,6-dimethylheptan-2-yl]-2,3,14,16-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Molecular Formula C28H46O7
Molecular Weight 494.7
Isomeric smiles CC(C)C(C)C[C@H]([C@@](C)([C@H]1[C@H](C[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)O)O)O
InChI InChI=1S/C28H46O7/c1-14(2)15(3)9-23(33)27(6,34)24-22(32)13-28(35)17-10-19(29)18-11-20(30)21(31)12-25(18,4)16(17)7-8-26(24,28)5/h10,14-16,18,20-24,30-35H,7-9,11-13H2,1-6H3/t15?,16-,18-,20+,21-,22-,23+,24-,25+,26+,27-,28+/m0/s1
InChIKey RVRAYMBCPTYQKZ-UFOPSCFWSA-N
External Database Links ChEMBL: CHEMBL411238  
Structural Information
nHA(Number of hydrogen bond acceptors) 7
nHD(Number of hydrogen bond donors) 6
nRot(Number of rotatable bonds) 5
nRing(Number of rings) 4
MaxRing(Number of atoms in the biggest ring) 17
nHet(Number of heteroatoms) 7

Stability
nRig(Number of rigid bonds) 21
Flexibility 0.238
Stereo Centers(Number of stereocenters) 12

Solubility
TPSA(Topological polar surface area) 138.45
logS(The logarithm of aqueous solubility value) -3.645
logP(The logarithm of the n-octanol/water distribution coefficient) 2.522
logD7.4(The logarithm of the n-octanol/water distribution coefficients at pH=7.4) 1.95

Pharmacokinetic Property
Quantitative Estimate of Drug-likeness 0.343
Synthetic accessibility score 5.421
Natural Product-likeness score 3.176
Lipinski Rule Accepted
GSK Rule Rejected
Golden Triangle Accepted

Absorption
Caco-2 Permeability -5.035
MDCK Permeability 1.52E-05
Pgp-substrate 0.994
HIA(human intestinal absorption) 0.043
F20%(20% Oral Bioavailability) 0.054
F30%(30% Oral Bioavailability) 0.724

Distribution
PPB(Plasma protein binding) 89.63%
VD(Volume Distribution) 0.736
BBB Penetration(Blood brain barrier penetration) 0.097
B3 Penetration(Blood brain barrier penetration) Non-Permeable
Fu(The fraction unbound in plasms) 6.17%

Metabolism
CYP1A2 inhibitor 0.004
CYP1A2 substrate 0.261
CYP2C19 inhibitor 0.011
CYP2C19 substrate 0.751
CYP2C9 inhibitor 0.033
CYP2C9 substrate 0.082
CYP2D6 inhibitor 0
CYP2D6 substrate 0.039
CYP3A4 inhibitor 0.546
CYP3A4 substrate 0.514

Excretion
CL(The clearance of a drug) 2.288
T1/2 0.344

Toxicology
NonBiodegradable Rule 1
Pfizer Rule Accepted
SR-MMP 0.88

Toxic Dose
FDAMDD(FDA Maximum (Recommended) Daily Dose) 0.979
IGC50 4.528
LC50FM 6.239
LC50DM 6.37

Reproductive Effects
NR-AR(Androgen receptor) 0.806
NR-AR-LBD(Androgen receptor) 0.108
NR-Aromatase 0.874
NR-ER(Estrogen receptor) 0.12
NR-ER-LBD(Estrogen receptor) 0.008

Allergy
Skin Sensitization Rule 3
Skin Sensitization 0.335

Acute Toxicity
Acute Toxicity Rule 3
Rat Oral Acute Toxicity 0.926

Organ Toxicity
hERG Blockers 0.185
H-HT(The human hepatotoxicity) 0.456
DILI(Drug-induced liver injury) 0.031

Primary Irritation
Eye Corrosion 0.003
Eye Irritation 0.039
Respiratory Toxicity 0.976

Mutagenic Effects
AMES Toxicity 0.037

Tumorigenic Effects
Carcinogencity 0.021
SR-ARE(Antioxidant Response Element) 0.041
SR-ATAD5(ATPase family AAA domain-containing protein 5) 0.516
SR-p53 0.649

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