8 alpha-hydroxy-13-epi-pimar-16-en-6,18-olide - Compound Card

8 alpha-hydroxy-13-epi-pimar-16-en-6,18-olide

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8 alpha-hydroxy-13-epi-pimar-16-en-6,18-olide

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles C=C[C@@]1(C)CCC2[C@](C1)(O)C[C@H]1C3[C@]2(C)CCC[C@]3(C(=O)O1)C
InChI InChI=1S/C20H30O3/c1-5-17(2)10-7-14-18(3)8-6-9-19(4)15(18)13(23-16(19)21)11-20(14,22)12-17/h5,13-15,22H,1,6-12H2,2-4H3/t13-,14?,15?,17-,18+,19+,20-/m0/s1
InChIKey ROWAYMVYPPFJTI-GAKRIXCDSA-N
Formula C20H30O3
HBA 3
HBD 1
MW 318.46
Rotatable Bonds 1
TPSA 46.53
LogP 3.85
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 318.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tetraclinis articulata Cupressaceae Plantae 13717

Showing of synonyms

  • Barrero A.F, Quílez del Moral J.F, et al. (2003). Diterpenoids from Tetraclinis articulata that Inhibit Various Human Leukocyte Functions. Journal of natural products, 2003, 66(6), 844-50. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=C1OC(C2C13)CC4C(C2CCC3)CCCC4

Level: 0

Mol. Weight: 318.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.82
Plasma Protein Binding
60.28
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
14.22
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.12
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.97
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.2
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
-5.17
Rat (Acute)
1.76
Rat (Chronic Oral)
1.87
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
375.88
Hydration Free Energy
-4.14
Log(D) at pH=7.4
3.53
Log(P)
4.02
Log S
-4.65
Log(Vapor Pressure)
-5.88
Melting Point
153.38
pKa Acid
9.64
pKa Basic
6.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9221
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8440
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.8432
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8394
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8378
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8119
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7805
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7781
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7768
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7624
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7516
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7497
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7496
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7473
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7458
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7427
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7352
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7311
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7295
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7281
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7251
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7245
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7229
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7210
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7178
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7170
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7142
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7133
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7103
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7101
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7100
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7094
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7092
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7092
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7088
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7049
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7033
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7022
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7021
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7006

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