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3alpha-hydroxylup-20(29)-ene-23,28-dioic acid 28-O-[4’-O-alpha-L-rhamnopyranosyl-6'-O-beta-D-glucopyranosyl]-beta-D-glucopyranosyl ester

Family: Plantae - Araliaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Lupane-Type Triterpene Glycoside

Canonical Smiles	CCC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CCC[C@@]1(C)C(=O)O)C(=O)O[C@]1(O)OC(CO[C@]2(O)OC(CO)[C@H](C([C@@H]2O)O)OC2O[C@H](C)[C@H]([C@@H]([C@@H]2O)O)O)[C@H](C([C@@H]1O)O)O
InChI	InChI=1S/C49H78O20/c1-8-22(2)24-12-17-47(19-18-45(6)25(30(24)47)10-11-29-43(4)14-9-15-44(5,41(59)60)28(43)13-16-46(29,45)7)42(61)69-49(63)38(57)34(54)32(52)27(68-49)21-64-48(62)39(58)36(56)37(26(20-50)67-48)66-40-35(55)33(53)31(51)23(3)65-40/h23-40,50-58,62-63H,2,8-21H2,1,3-7H3,(H,59,60)/t23-,24+,25-,26?,27?,28-,29-,30-,31-,32-,33+,34?,35+,36?,37-,38+,39+,40?,43+,44-,45-,46-,47+,48+,49-/m1/s1
InChIKey	YIFOLXBSBFRWMW-ZSXVYUFLSA-N
Formula	C₄₉H₇₈O₂₀
HBA	19
HBD	12
MW	987.14
Rotatable Bonds	11
TPSA	332.28
LogP	0.15
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	69
Formal Charge	0
Fraction CSP3	0.92
Exact Mass	986.51
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Schefflera actinophylla	Araliaceae	Plantae	52501

Showing of synonyms

Wanas AS, Matsunami K, et al. (2010). Triterpene glycosides and glucosyl esters, and a triterpene from the leaves of Schefflera actinophylla. Chemical and Pharmaceutical Bulletin,2010,58(12),1596-1601. [View] [PubMed]

Pubchem: 162817486

Nmrshiftdb2: 70089214

No compound-protein relationship available.

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C3C(CCC5)C45C(=O)OC(O6)CCCC6COC(OC7)CCC7OC8CCCCO8

Level: 3

Mol. Weight: 987.14 g/mol

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C3C(CCC5)C45C(=O)OC(O6)CCCC6COC7CCCCO7

Level: 2

Mol. Weight: 987.14 g/mol

SMILES: O1CCCCC1COC(OC2)CCC2OC3CCCCO3

Level: 2

Mol. Weight: 987.14 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCC2)C4C(CC3)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 987.14 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 987.14 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 987.14 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 987.14 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 987.14 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.27
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 12365.89
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1617019.55

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.94
Plasma Protein Binding: 79.21
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: Inhibitor

Excretion

Clearance: 0.91
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -37601.3
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.07
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2934808153.07
Rat (Acute): 3.47
Rat (Chronic Oral): 7.16
Fathead Minnow: 3704578.09
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: 330079166.22
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -171.6
Log(P): 2.46
Log S: -2.94
Log(Vapor Pressure): -10869201.97
Melting Point: 216.44
pKa Acid: -79122.65
pKa Basic: -618.16

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	0.9769
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.9769
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.9420
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.9420
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8804
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8804
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8576
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8576
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8437
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8437
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7630
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7630
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7548
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7548
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7369
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7369
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7267
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7267
Cellular retinoic acid-binding protein 2	P29373	RABP2_HUMAN	Homo sapiens	3	0.7243
Cellular retinoic acid-binding protein 2	P29373	RABP2_HUMAN	Homo sapiens	3	0.7243
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7002
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7002

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