(1R*,2R*,3E,7R*,11R*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-l8-O-acetyldolabella-3,8(17)-dien-2,7,9,16,18-pentol - Compound Card

(1R*,2R*,3E,7R*,11R*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-l8-O-acetyldolabella-3,8(17)-dien-2,7,9,16,18-pentol

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(1R*,2R*,3E,7R*,11R*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-l8-O-acetyldolabella-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 O=C(C[C@@](CC(=O)O)(O)C)OC/C/1=C/[C@H](O)[C@@]2(C)CC[C@H]([C@@H]2C[C@H](C(=C)[C@H](CC1)O)O)C(OC(=O)C)(C)C
InChI InChI=1S/C28H44O10/c1-16-21(30)8-7-18(15-37-25(35)14-27(5,36)13-24(33)34)11-23(32)28(6)10-9-19(20(28)12-22(16)31)26(3,4)38-17(2)29/h11,19-23,30-32,36H,1,7-10,12-15H2,2-6H3,(H,33,34)/b18-11+/t19-,20+,21+,22-,23+,27-,28+/m1/s1
InChIKey FRLDVKJGPODRTR-UJWFBMNUSA-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: 163070941

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)
-6.12
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.100
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.800
Plasma Protein Binding
77.31
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
10.290
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.430
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.330
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-339.630
Rat (Acute)
2.920
Rat (Chronic Oral)
2.760
Fathead Minnow
3.990
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
494.480
Hydration Free Energy
-3.050
Log(D) at pH=7.4
0.040
Log(P)
1.08
Log S
-2.41
Log(Vapor Pressure)
-11.7
Melting Point
157.28
pKa Acid
3.55
pKa Basic
6.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8606
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8606
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8506
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8506
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8433
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8433
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8099
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8099
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7800
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7800
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7683
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7683
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7667
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7667
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7655
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7655
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7648
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7648
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7600
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7600
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7582
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7582
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7418
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7418
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7328
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7328
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7217
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7217
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7152
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7152
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7120
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7120
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7098
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7098
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7019
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7019

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