ANPDB

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Semipapposide B

Family: Plantae - Caprifoliaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Triterpenoid Saponin

Canonical Smiles	OCC1O[C@@H](O[C@H]2C(C)O[C@H](C([C@H]2O)O)OC2[C@H](O)CO[C@H]([C@H]2O)O[C@@H]2C(O)[C@H](O[C@@H]3[C@@H](OC[C@@H](C3O)O)O[C@H]3CC[C@]4(C(C3(C)C)CC[C@@]3(C4CC=C4[C@@]3(C)CC[C@@]3([C@@]4(C)CC(C)(C)CC3)C(=O)O[C@@H]3OC(CO[C@@H]4OC(CO)[C@H](C([C@@H]4O)O)O)[C@H]([C@@H](C3O)O)O)C)C)OC([C@@H]2O)C)[C@H](C([C@@H]1O)O[C@@H]1OC(C)[C@@H]([C@@H](C1O)O)O)O
InChI	InChI=1S/C77H126O38/c1-28-40(82)46(88)51(93)64(103-28)113-60-45(87)34(23-79)107-68(56(60)98)110-57-30(3)105-65(53(95)49(57)91)111-58-32(81)25-100-63(54(58)96)112-59-41(83)29(2)104-67(55(59)97)114-61-42(84)31(80)24-101-69(61)109-39-15-16-73(8)36(72(39,6)7)14-17-74(9)37(73)12-13-38-75(74,10)19-21-77(20-18-71(4,5)27-76(38,77)11)70(99)115-66-52(94)48(90)44(86)35(108-66)26-102-62-50(92)47(89)43(85)33(22-78)106-62/h13,28-37,39-69,78-98H,12,14-27H2,1-11H3/t28?,29?,30?,31-,32+,33?,34?,35?,36?,37?,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-,65-,66-,67-,68-,69-,73-,74+,75+,76-,77+/m0/s1
InChIKey	WCIQMSJUMCHOHU-YRKGGOSKSA-N
Formula	C₇₇H₁₂₆O₃₈
HBA	38
HBD	21
MW	1659.82
Rotatable Bonds	19
TPSA	589.58
LogP	-5.99
Number Rings	13
Number Aromatic Rings	0
Heavy Atom Count	115
Formal Charge	0
Fraction CSP3	0.96
Exact Mass	1658.79
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Scabiosa semipapposa	Caprifoliaceae	Plantae	87007

Showing of synonyms

Bendamene S, Boutaghane N, et al. (2020). Semipapposides A-M, triterpenoid bidesmosides saponins from the roots of Scabiosa semipapposa. Phytochemistry, 2020, 180, 112526. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC(OCCC8)C8OC(OCC9)CC9OC(OCC1)CC1OC(OC1)CCC1OC(OCC1)CC1OC1CCCCO1

Level: 8

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC(OCCC8)C8OC(OCC9)CC9OC(OCC1)CC1OC(OC1)CCC1OC1CCCCO1

Level: 7

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC(OCC8)CC8OC(OCC9)CC9OC(OC1)CCC1OC(OCC1)CC1OC1CCCCO1

Level: 7

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC(OCCC8)C8OC(OCC9)CC9OC(OCC1)CC1OC1CCCCO1

Level: 6

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC(OCC8)CC8OC(OCC9)CC9OC(OC1)CCC1OC1CCCCO1

Level: 6

Mol. Weight: 1659.82 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC(OCC7)CC7OC(OCC8)CC8OC(OC9)CCC9OC(OCC1)CC1OC1CCCCO1

Level: 6

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC(OCCC8)C8OC(OCC9)CC9OC1CCCCO1

Level: 5

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC(OCC8)CC8OC(OCC9)CC9OC1CCCCO1

Level: 5

Mol. Weight: 1659.82 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC(OCC7)CC7OC(OCC8)CC8OC(OC9)CCC9OC1CCCCO1

Level: 5

Mol. Weight: 1659.82 g/mol

SMILES: C1OCCCC1OC(OCC2)CC2OC(OCC3)CC3OC(OC4)CCC4OC(OCC5)CC5OC6CCCCO6

Level: 5

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC(OCCC8)C8OC9CCCCO9

Level: 4

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC(OCC8)CC8OC9CCCCO9

Level: 4

Mol. Weight: 1659.82 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC(OCC7)CC7OC(OCC8)CC8OC9CCCCO9

Level: 4

Mol. Weight: 1659.82 g/mol

SMILES: C1OCCCC1OC(OCC2)CC2OC(OCC3)CC3OC(OC4)CCC4OC5CCCCO5

Level: 4

Mol. Weight: 1659.82 g/mol

SMILES: C1COCCC1OC(OCC2)CC2OC(OC3)CCC3OC(OCC4)CC4OC5CCCCO5

Level: 4

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC8CCCCO8

Level: 3

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1659.82 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC(OCC7)CC7OC8CCCCO8

Level: 3

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4CCOCC4

Level: 3

Mol. Weight: 1659.82 g/mol

SMILES: C1OCCCC1OC(OCC2)CC2OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1659.82 g/mol

SMILES: C1COCCC1OC(OCC2)CC2OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1659.82 g/mol

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(O6)CCCC6COC7CCCCO7

Level: 2

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 2

Mol. Weight: 1659.82 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC7CCCCO7

Level: 2

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCOCC3

Level: 2

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1659.82 g/mol

SMILES: C1COCCC1OC(OC2)CCC2OC3CCCCO3

Level: 2

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 1659.82 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 1

Mol. Weight: 1659.82 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1659.82 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1659.82 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1659.82 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 1659.82 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1659.82 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.04
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 30332929954323522000000000
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 3964154028819992400000000000

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.49
Plasma Protein Binding: 33.85
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: 1.28
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -92197243894974320000000000
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -37645237791064490000
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: Toxic
T. Pyriformis: -7194748012288728000000000000000
Rat (Acute): 5802267697304655.0
Rat (Chronic Oral): 15432110196844233000000
Fathead Minnow: 9081840608938766000000000000
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: 809209729180919600000000000000
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -449839865651576840000000
Log(P): -52366673936587260000
Log S: -2.37
Log(Vapor Pressure): -26646863572587580000000000000
Melting Point: -8097027873388704000000
pKa Acid: -194164551195951060000000000
pKa Basic: -1562047194383216500000000

No predicted protein targets found for this compound.

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