(12S,13S)-12,13-dihydroxylabda-8(17),14-dien-18-oic acid - Compound Card

(12S,13S)-12,13-dihydroxylabda-8(17),14-dien-18-oic acid

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(12S,13S)-12,13-dihydroxylabda-8(17),14-dien-18-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Myristicaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles C=C[C@@]([C@H](C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@@]2(C)CC(=O)O)O)(O)C
InChI InChI=1S/C21H34O4/c1-6-21(5,25)17(22)12-15-14(2)8-9-16-19(3,13-18(23)24)10-7-11-20(15,16)4/h6,15-17,22,25H,1-2,7-13H2,3-5H3,(H,23,24)/t15-,16-,17-,19-,20+,21-/m0/s1
InChIKey RWCBOSBMPBXXBY-IZTFOULLSA-N
Formula C21H34O4
HBA 3
HBD 3
MW 350.5
Rotatable Bonds 6
TPSA 77.76
LogP 3.93
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 350.25
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pycnanthus angolensis Myristicaceae Plantae 224864

Showing of synonyms

  • Wabo HK, Tatsimo SN, et al. (2007). Pycnanthuquinone C: a new terpenoid-quinone from Pycnanthus angolensis.. Planta medica,2007, 73(2), 187-189. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C=C(C1)CCC(C12)CCCC2

Level: 0

Mol. Weight: 350.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.95
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.97
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.78
Plasma Protein Binding
86.39
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.01
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.32
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.58
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.1
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
-1.4
Rat (Acute)
3.41
Rat (Chronic Oral)
2.33
Fathead Minnow
4.03
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
382.27
Hydration Free Energy
-7.24
Log(D) at pH=7.4
0.98
Log(P)
3.09
Log S
-4.0
Log(Vapor Pressure)
-8.97
Melting Point
160.55
pKa Acid
4.93
pKa Basic
6.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9166
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9018
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8785
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8758
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8681
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8403
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8245
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8210
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8192
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8154
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.8088
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7953
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7891
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7859
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7706
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7704
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7627
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7615
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7580
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7577
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7532
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7428
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7427
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7377
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7332
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7325
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7290
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7220
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7208
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7187
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7125
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7053

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