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(25R)-3beta-[(O-beta-D-glucopyranosyl-(1→3)-O-beta-D-glucopyranosyl-(1→2)-O-[O-alpha-L-rhamnopyranosyl-(1→4)-beta-D-glucopyranosyl-(1→3)]-O-beta-D-glucopyranosyl-(1→4)-beta-D-galactopyranosyl)oxy]-5alpha-spirostan-12-one

Family: Plantae - Agavaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Steroidal Saponin

Canonical Smiles	OCC1OC(O[C@H]2CC[C@]3([C@H](C2)CC[C@@H]2[C@@H]3CC(=O)[C@]3([C@H]2C[C@H]2[C@@H]3[C@H](C)[C@]3(O2)CC[C@H](CO3)C)C)C)C(C(C1OC1OC(CO)C(C(C1OC1OC(CO)C(C(C1O)OC1OC(CO)C(C(C1O)O)O)O)OC1CC(CO)C(C(C1O)O)OC1OC(C)C(C(C1O)O)O)O)O)O
InChI	InChI=1S/C64H104O32/c1-22-8-11-64(84-21-22)23(2)38-31(96-64)14-30-28-7-6-26-13-27(9-10-62(26,4)29(28)15-37(70)63(30,38)5)86-58-50(82)47(79)53(36(20-69)91-58)93-61-56(95-60-51(83)54(42(74)34(18-67)89-60)94-59-49(81)45(77)41(73)33(17-66)88-59)55(43(75)35(19-68)90-61)87-32-12-25(16-65)52(46(78)40(32)72)92-57-48(80)44(76)39(71)24(3)85-57/h22-36,38-61,65-69,71-83H,6-21H2,1-5H3/t22-,23+,24?,25?,26+,27+,28-,29+,30+,31+,32?,33?,34?,35?,36?,38+,39?,40?,41?,42?,43?,44?,45?,46?,47?,48?,49?,50?,51?,52?,53?,54?,55?,56?,57?,58?,59?,60?,61?,62+,63-,64-/m1/s1
InChIKey	QMNKTBBRCHBSLW-WDNHQDTMSA-N
Formula	C₆₄H₁₀₄O₃₂
HBA	32
HBD	18
MW	1385.5
Rotatable Bonds	17
TPSA	501.2
LogP	-6.39
Number Rings	12
Number Aromatic Rings	0
Heavy Atom Count	96
Formal Charge	0
Fraction CSP3	0.98
Exact Mass	1384.65
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Furcraea tuberosa	Agavaceae	Plantae	39538

Showing of synonyms

Tapondjoua LA, Jenett-Siems K, et al. (2017). Flavonol glycosides and cytotoxic steroidal saponins from Furcraea tuberosa (Agavaceae). Natural Product Communications, 2017, 12(3), 347-350. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8OCCC(C8OC(OCC9)CC9OC1CCCCO1)OC1CCC(CC1)OC1CCCCO1

Level: 6

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8OCCC(OC9CCCCC9)C8OC(OCC1)CC1OC1CCCCO1

Level: 5

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8OCCC(C8OC9CCCCO9)OC1CCC(CC1)OC1CCCCO1

Level: 5

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3C(CCOC3OC4CCCOC4)OC5CCC(CC5)OC6CCCCO6

Level: 5

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCCC8)C8OC(OCC9)CC9OC1CCCCO1

Level: 4

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8OCCC(C8OC9CCCCO9)OC1CCCCC1

Level: 4

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCC8)CC8OC9CCC(CC9)OC1CCCCO1

Level: 4

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3C(OC4CCCCC4)CCOC3OC5CCCOC5

Level: 4

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC1OC(CC2)CCC2OC3C(COCC3)OC(OCC4)CC4OC5CCCCO5

Level: 4

Mol. Weight: 1385.5 g/mol

SMILES: C1OCCCC1OC2OCCC(C2OC3CCCCO3)OC4CCC(CC4)OC5CCCCO5

Level: 4

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCCC8)C8OC9CCCCO9

Level: 3

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCC8)CC8OC9CCCCC9

Level: 3

Mol. Weight: 1385.5 g/mol

SMILES: C1OCCCC1OC(OCCC2)C2OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC1OC2C(OC3CCCCC3)CCOC2OC4CCCOC4

Level: 3

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC1OC(COCC2)C2OC3CCC(CC3)OC4CCCCO4

Level: 3

Mol. Weight: 1385.5 g/mol

SMILES: C1OCCCC1OC(OCC2)CC2OC3CCC(CC3)OC4CCCCO4

Level: 3

Mol. Weight: 1385.5 g/mol

SMILES: C1CCCCC1OC2C(COCC2)OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8CCCCO8

Level: 2

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1385.5 g/mol

SMILES: C1COCCC1OC2CCC(CC2)OC3CCCCO3

Level: 2

Mol. Weight: 1385.5 g/mol

SMILES: C1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1385.5 g/mol

SMILES: C1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 1

Mol. Weight: 1385.5 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1385.5 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1385.5 g/mol

SMILES: C1CCCCC1OC2CCOCC2

Level: 1

Mol. Weight: 1385.5 g/mol

SMILES: C1CCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1385.5 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4=O)C6C(CC5)CCCC6

Level: 0

Mol. Weight: 1385.5 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1385.5 g/mol

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 1385.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.04
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 6305044644645503.0
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 823995241452811400

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.55
Plasma Protein Binding: 2.97
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: 0.99
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -19164264601231330
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -7824995459.26
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.05
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: -1495511743828678400000
Rat (Acute): 1205984.66
Rat (Chronic Oral): 3207741074894.77
Fathead Minnow: 1887764910405100800
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: 168203596227312940000
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -93504416220201.62
Log(P): -10885017627.79
Log S: -1.1
Log(Vapor Pressure): -5538860306781245000
Melting Point: -1683060952489.95
pKa Acid: -40359326475656160
pKa Basic: -324689599970186.1

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8721
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8721
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8615
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8615
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8500
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8500
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8475
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8475
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8371
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8371
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8123
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8123
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7902
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7902
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7692
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7692
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7637
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7637
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7584
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7584
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7559
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7559
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7537
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7537
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7439
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7439
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7380
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7380
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7372
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7372
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7308
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7308
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7294
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7294
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7185
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7185
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7183
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7183
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7142
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7142
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7137
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7137
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7070
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7070

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