15S,16-dihyroxy-7-oxopimar-8(9)-ene - Compound Card

15S,16-dihyroxy-7-oxopimar-8(9)-ene

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15S,16-dihyroxy-7-oxopimar-8(9)-ene

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OC[C@H](C1(C)CCC2=C(C1)C(=O)CC1[C@]2(C)CCCC1(C)C)O
InChI InChI=1S/C20H32O3/c1-18(2)7-5-8-20(4)14-6-9-19(3,17(23)12-21)11-13(14)15(22)10-16(18)20/h16-17,21,23H,5-12H2,1-4H3/t16?,17-,19?,20-/m1/s1
InChIKey VHQSTIAIPGOSMC-LNXHZJMOSA-N
Formula C20H32O3
HBA 3
HBD 2
MW 320.47
Rotatable Bonds 2
TPSA 57.53
LogP 3.63
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 320.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Lavandula multifida Lamiaceae Plantae 260634

Showing of synonyms

  • Politi M, De Tommasi N, et al. (2002). Structure and absolute configuration of new diterpenes from Lavandula multifida. Journal of Natural Products,2002,65(11),1742-1745. [View] [PubMed]
Pubchem: 162970389
Nmrshiftdb2: 70121407

No compound-protein relationship available.

Structure

SMILES: C1CCCC(=C12)C3C(CC2=O)CCCC3

Level: 0

Mol. Weight: 320.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.05
Plasma Protein Binding
62.76
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
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.06
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.07
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.36
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
-0.52
Rat (Acute)
1.98
Rat (Chronic Oral)
1.87
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
390.91
Hydration Free Energy
-7.21
Log(D) at pH=7.4
3.3
Log(P)
3.47
Log S
-3.74
Log(Vapor Pressure)
-7.18
Melting Point
151.91
pKa Acid
10.1
pKa Basic
6.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9098
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9098
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8884
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8884
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8711
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8711
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8223
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8223
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.8201
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.8201
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7991
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7991
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7988
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7988
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7835
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7835
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7734
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7734
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7641
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7641
Transcriptional activator protein LasR P25084 LASR_PSEAE Pseudomonas aeruginosa 4 0.7467
Transcriptional activator protein LasR P25084 LASR_PSEAE Pseudomonas aeruginosa 4 0.7467
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7432
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7432
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7430
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7430
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7402
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7402
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7395
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7395
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7376
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7376
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7339
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7339
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7325
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7325
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7064
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7064
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7020
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7020
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7005
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7005

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