ANPDB

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Alpinoside A

Family: Plantae - Apocynaceae
Kingdom: Plantae
Class: Steroid
- Subclass: Polyhydroxypregnane Glycoside

Canonical Smiles	CO[C@@H]1C[C@H](O[C@H]2CC[C@]3(C(=CC[C@@]4(C3C[C@@H](OC(=O)/C=C/c3ccccc3)[C@]3([C@]4(O)CC[C@@]3(O)C(=O)C)C)O)C2)C)OC([C@H]1O[C@H]1C[C@@H](OC)[C@@H](C(O1)C)O[C@@H]1OC(C)[C@H]([C@@H](C1O)OC)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)C
InChI	InChI=1S/C63H94O27/c1-29-51(87-44-25-37(78-8)52(30(2)81-44)88-58-50(73)55(79-9)53(31(3)82-58)89-57-49(72)47(70)54(39(28-65)85-57)90-56-48(71)46(69)45(68)38(27-64)84-56)36(77-7)24-43(80-29)83-35-18-19-59(5)34(23-35)17-20-62(75)40(59)26-41(86-42(67)16-15-33-13-11-10-12-14-33)60(6)61(74,32(4)66)21-22-63(60,62)76/h10-17,29-31,35-41,43-58,64-65,68-76H,18-28H2,1-9H3/b16-15+/t29?,30?,31?,35-,36+,37+,38?,39?,40?,41+,43-,44-,45+,46-,47+,48?,49?,50?,51+,52+,53+,54+,55+,56-,57-,58-,59-,60+,61+,62-,63+/m0/s1
InChIKey	VCIOSRIGGRVAII-NEHJDXMRSA-N
Formula	C₆₃H₉₄O₂₇
HBA	27
HBD	11
MW	1283.42
Rotatable Bonds	19
TPSA	385.89
LogP	-0.68
Number Rings	10
Number Aromatic Rings	1
Heavy Atom Count	90
Formal Charge	0
Fraction CSP3	0.81
Exact Mass	1282.6
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Oxystelma esculentum	Apocynaceae	Plantae	126763

Showing of synonyms

Hamed AI, Sheded MG, et al. (2004). Polyhydroxypregnane glycosides from Oxystelma esculentum var. Alpine. Phytochemistry,2004,65(7),975-980. [View] [PubMed]

Pubchem: 163017614

Nmrshiftdb2: 70080324

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCC(C5)OC(OC6)CCC6OC(OC7)CCC7OC(OC8)CCC8OC(OC9)CCC9OC1CCCCO1

Level: 6

Mol. Weight: 1283.42 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCC(C5)OC(OC6)CCC6OC(OC7)CCC7OC(OC8)CCC8OC9CCCCO9

Level: 5

Mol. Weight: 1283.42 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC(OC5)CCC5OC(OC6)CCC6OC(OC7)CCC7OC(OC8)CCC8OC9CCCCO9

Level: 5

Mol. Weight: 1283.42 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCC(C5)OC(OC6)CCC6OC(OC7)CCC7OC8CCCCO8

Level: 4

Mol. Weight: 1283.42 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC(OC5)CCC5OC(OC6)CCC6OC(OC7)CCC7OC8CCCCO8

Level: 4

Mol. Weight: 1283.42 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCC(OC3)OC4CCC(OC4)OC5CCCOC5

Level: 4

Mol. Weight: 1283.42 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCC(C5)OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 1283.42 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC(OC5)CCC5OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 1283.42 g/mol

SMILES: C1OCCCC1OC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1283.42 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCC(C5)OC6CCCCO6

Level: 2

Mol. Weight: 1283.42 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC(OC5)CCC5OC6CCCCO6

Level: 2

Mol. Weight: 1283.42 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1283.42 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C(C23)CCC2)CC4C3CC=C5C4CCCC5

Level: 1

Mol. Weight: 1283.42 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 1283.42 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1283.42 g/mol

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 1283.42 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1283.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1283.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.5
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 3284887966458.150
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 429296052618107.06

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.680
Plasma Protein Binding: 74.26
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: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 2.220
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -9984453734362.570
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -4076772.160
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.050
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: -779151664625277824.000
Rat (Acute): 551.040
Rat (Chronic Oral): 1671212230.570
Fathead Minnow: 983513189597997.750
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: 87632954712871424.000
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -48715175786.980
Log(P): -5671019.41
Log S: -2.93
Log(Vapor Pressure): -2885709988923942.5
Melting Point: -876860134.79
pKa Acid: -21026943154458.008
pKa Basic: -169161148530.5

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8347
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8347
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7807
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7807
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7746
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7746
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7521
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7521
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7434
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7434
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7400
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7400
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7175
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7175
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7085
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7085

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