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20(S)-protopanxadiol

Family: Plantae - Burseraceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Triterpenoid

Canonical Smiles	CC(=CCC[C@@]([C@H]1CC[C@@]2([C@@H]1[C@H](O)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)(O)C)C
InChI	InChI=1S/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h10,20-25,31-33H,9,11-18H2,1-8H3/t20-,21+,22-,23+,24-,25-,27-,28+,29+,30-/m0/s1
InChIKey	PYXFVCFISTUSOO-HKUCOEKDSA-N
Formula	C₃₀H₅₂O₃
HBA	3
HBD	3
MW	460.74
Rotatable Bonds	4
TPSA	60.69
LogP	6.5
Number Rings	4
Number Aromatic Rings	0
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.93
Exact Mass	460.39
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Boswellia species	Burseraceae	Plantae	173701

Showing of synonyms

Melese A, Dagne E. (2007). Phytochemical investigation of the resins of Boswellia species collected from Kebtele area in Agew-Awi (Gojjam). M.Sc. Thesis, Addis Ababa University, Ethiopia, 2007. [View] [PubMed]

Pubchem: 11213350

Cas: 30636-90-9

Zinc: ZINC000008740122

Chebi: 75950

Metabolights: MTBLC75950

Chembl: CHEMBL375563

Bindingdb: 50423990

CPRiL: 65020

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 460.74 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.82
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.66
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.57

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.21
Plasma Protein Binding: 88.25
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: 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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.51
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.68
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.32
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 5.72
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: -72.12
Rat (Acute): 3.01
Rat (Chronic Oral): 1.85
Fathead Minnow: 3.87
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: 422.53
Hydration Free Energy: -2.74
Log(D) at pH=7.4: 5.83
Log(P): 7.08
Log S: -6.03
Log(Vapor Pressure): -8.51
Melting Point: 188.58
pKa Acid: 11.0
pKa Basic: 7.83

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9438
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9438
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9156
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9156
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8537
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8537
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8153
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8153
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8007
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8007
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7791
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7791
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7784
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7784
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7748
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7748
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	4	0.7610
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	4	0.7610
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7576
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7576
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7449
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7449
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7415
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7415
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7278
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7278
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7133
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7133

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