Diplopimarane - Compound Card

Diplopimarane

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Diplopimarane

Structure
Zoomed Structure
  • Family: Fungi - Botryosphaeriaceae
  • Kingdom: Fungi
  • Class: Terpenoid
    • Subclass: Pimarane Diterpenoid
Canonical Smiles C=C[C@]1(C)CCc2c([C@H]1O)c(O)c(c1c2CCCC1(C)C)O
InChI InChI=1S/C19H26O3/c1-5-19(4)10-8-11-12-7-6-9-18(2,3)14(12)16(21)15(20)13(11)17(19)22/h5,17,20-22H,1,6-10H2,2-4H3/t17-,19-/m1/s1
InChIKey SSDQVAYQSDWMDH-IEBWSBKVSA-N
Formula C19H26O3
HBA 3
HBD 3
MW 302.41
Rotatable Bonds 1
TPSA 60.69
LogP 3.88
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 302.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Diplodia quercivora Botryosphaeriaceae Fungi 1281306

Showing of synonyms

  • Andolfi A, Maddau L, et al. (2014). Diplopimarane, a 20-nor-ent-pimarane produced by the oak pathogen Diplodia quercivora. Journal of Natural Products,2014,77(6),2352-2360. [View] [PubMed]
Pubchem: 101889605

No compound-protein relationship available.

Structure

SMILES: C1CCCc(c1c23)ccc2CCCC3

Level: 0

Mol. Weight: 302.41 g/mol

Phytotoxicity
Zootoxic

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
72.61
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
14.98
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.0
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.41
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.85
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
2.45
Rat (Acute)
2.33
Rat (Chronic Oral)
2.76
Fathead Minnow
3.98
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
362.72
Hydration Free Energy
-8.11
Log(D) at pH=7.4
3.09
Log(P)
4.24
Log S
-3.77
Log(Vapor Pressure)
-7.37
Melting Point
165.71
pKa Acid
9.2
pKa Basic
5.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8799
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8799
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8183
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8183
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7614
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7614
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7589
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7589
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7455
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7455
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7435
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7435
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7317
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7317
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7292
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7292
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7219
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7219
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7169
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7169
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7035
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7035

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