(1R*,2R*,3E,7R*,11R*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,8(17)-dien-2,7,9,16,18-pentol - Compound Card

(1R*,2R*,3E,7R*,11R*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,8(17)-dien-2,7,9,16,18-pentol

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(1R*,2R*,3E,7R*,11R*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,8(17)-dien-2,7,9,16,18-pentol

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles OC(=O)C[C@@](CC(=O)OC/C/1=C/[C@@H](OC(=O)C)[C@@]2(C)CC[C@H]([C@@H]2C[C@H](C(=C)[C@@H](CC1)O)O)C(O)(C)C)(O)C
InChI InChI=1S/C28H44O10/c1-16-21(30)8-7-18(15-37-25(34)14-27(5,36)13-24(32)33)11-23(38-17(2)29)28(6)10-9-19(26(3,4)35)20(28)12-22(16)31/h11,19-23,30-31,35-36H,1,7-10,12-15H2,2-6H3,(H,32,33)/b18-11+/t19-,20+,21-,22-,23-,27+,28+/m1/s1
InChIKey VBPRRBFPNNAJBG-HWBFDHIJSA-N
Formula C28H44O10
HBA 9
HBD 5
MW 540.65
Rotatable Bonds 8
TPSA 170.82
LogP 2.27
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 540.29
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Chrozophora obliqua Euphorbiaceae Plantae 316753

Showing of synonyms

  • Mohamed KM, Ohtani K, et al. (1995). 3-Hydroxy-3-methylglutaryl dolabellane diterpenes from Chrozophora obliqua. Phytochemistry,1995,39(1),151-161. [View]
Pubchem: 162869067

No compound-protein relationship available.

Structure

SMILES: C1C=CCCCC(=C)CCC(C12)CCC2

Level: 0

Mol. Weight: 540.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.17
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.03
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.79
Plasma Protein Binding
77.54
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.69
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.53
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.42
Micronucleos
Toxic
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
-329.22
Rat (Acute)
2.79
Rat (Chronic Oral)
2.72
Fathead Minnow
4.04
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
495.03
Hydration Free Energy
-3.09
Log(D) at pH=7.4
-0.51
Log(P)
0.75
Log S
-2.55
Log(Vapor Pressure)
-11.61
Melting Point
163.61
pKa Acid
3.61
pKa Basic
5.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8881
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8881
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8237
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8237
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7866
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7866
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7835
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7835
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7830
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7830
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7826
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7826
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7608
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7608
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7384
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7384
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7349
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7349
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7306
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7306
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7227
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7227
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7132
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7132
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7074
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7074
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7054
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7054
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7006
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7006

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