17-hydroxy-ent-pimara-8(14),15-dien-3-one - Compound Card

17-hydroxy-ent-pimara-8(14),15-dien-3-one

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17-hydroxy-ent-pimara-8(14),15-dien-3-one

Structure
Zoomed Structure
  • Family: Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OC[C@]1(C=C)CC[C@H]2C(=C1)CCC1[C@@]2(C)CCC(=O)C1(C)C
InChI InChI=1S/C20H30O2/c1-5-20(13-21)11-8-15-14(12-20)6-7-16-18(2,3)17(22)9-10-19(15,16)4/h5,12,15-16,21H,1,6-11,13H2,2-4H3/t15-,16?,19-,20+/m0/s1
InChIKey YTULBIIRXFWHFX-HUBHPDRSSA-N
Formula C20H30O2
HBA 2
HBD 1
MW 302.46
Rotatable Bonds 2
TPSA 37.3
LogP 4.29
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 302.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sclerocroton integerrimus Euphorbiaceae Plantae 1206814

Showing of synonyms

  • Tembu VJ, Langat MK, et al. (2014). Use of Circular Dichroism to Determine the Absolute Configuration of a Pimarane Diterpenoid from the Southern African Sclerocroton integerrimus (Euphorbiaceae). Natural Product Communications, 9(8) 2014, 1131-1133. [View]

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C=12)C3C(CC2)CC(=O)CC3

Level: 0

Mol. Weight: 204.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.56
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.39
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.07
Plasma Protein Binding
64.37
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
18.06
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.76
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.13
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.97
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.56
Rat (Acute)
1.86
Rat (Chronic Oral)
1.76
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
364.46
Hydration Free Energy
-4.41
Log(D) at pH=7.4
3.64
Log(P)
3.86
Log S
-4.29
Log(Vapor Pressure)
-5.98
Melting Point
118.73
pKa Acid
10.95
pKa Basic
6.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9207
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9083
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8984
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8638
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8577
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8421
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8393
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.8373
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8362
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8347
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8307
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8201
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8124
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8120
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7933
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7886
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7843
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7823
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7735
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7703
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7663
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7633
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7627
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7612
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7603
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7550
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7541
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7497
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7472
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7435
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7432
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7395
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7387
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7383
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7349
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7330
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7286
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7269
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7260
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7245
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7242
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7236
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7224
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7215
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7171
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7159
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7149
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7144
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7141
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7108
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7085
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7070
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7060
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7057
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7045
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7031
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7019
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7008

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