ANPDB

Select a section from the left sidebar

Heinsiagenin A 3-O-[alpha-L-rhamnopyranosyl-(1→2)-beta-D-glucopyranosyl-(1→2)]-[beta-D-glucopyranosyl-(1→4)]-beta-D-glucopyranoside

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

Canonical Smiles	OC[C@H]1O[C@@H](O[C@H]2CC[C@]34[C@H](C2(C)C)CC[C@@H]2[C@@]4(C3)CC[C@]3([C@@]2(C)CC[C@@H]3[C@@H](/C=C/C=C(/C(=O)N[C@@H]2C(=O)O[C@@H]([C@@H]2C)C)\C)C)C)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O
InChI	InChI=1S/C60H95NO23/c1-25(11-10-12-26(2)50(74)61-37-27(3)28(4)76-51(37)75)30-15-17-58(9)35-14-13-34-56(6,7)36(16-18-59(34)24-60(35,59)20-19-57(30,58)8)81-54-49(46(73)47(33(23-64)80-54)82-53-45(72)42(69)39(66)31(21-62)78-53)84-55-48(43(70)40(67)32(22-63)79-55)83-52-44(71)41(68)38(65)29(5)77-52/h10-12,25,27-49,52-55,62-73H,13-24H2,1-9H3,(H,61,74)/b11-10+,26-12+/t25-,27+,28-,29+,30-,31-,32-,33-,34+,35+,36+,37+,38+,39-,40-,41-,42+,43+,44-,45-,46+,47-,48-,49-,52+,53+,54+,55+,57-,58+,59-,60+/m1/s1
InChIKey	XKQVRFDRHHYCRC-SDOYSNKRSA-N
Formula	C₆₀H₉₅NO₂₃
HBA	23
HBD	13
MW	1198.4
Rotatable Bonds	16
TPSA	372.0
LogP	-0.68
Number Rings	10
Number Aromatic Rings	0
Heavy Atom Count	84
Formal Charge	0
Fraction CSP3	0.9
Exact Mass	1197.63
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Mussaenda luteola	Rubiaceae	Plantae	43523

Showing of synonyms

Mohamed S.M, Bachkeet E.Y, et al. (2015). Potent antitrypanosomal triterpenoid saponins from Mussaenda luteola. Fitoterapia, 2015, 107, 114-121. [View] [PubMed]

Pubchem: 134693005

No compound-protein relationship available.

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC(OCC(C7)OC8CCCCO8)C7OC(OCCC9)C9OC1CCCCO1

Level: 5

Mol. Weight: 1198.4 g/mol

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC(OCCC7)C7OC(OCCC8)C8OC9CCCCO9

Level: 4

Mol. Weight: 1198.4 g/mol

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC(C7OC8CCCCO8)OCC(C7)OC9CCCCO9

Level: 4

Mol. Weight: 1198.4 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC(OCC(C6)OC7CCCCO7)C6OC(OCCC8)C8OC9CCCCO9

Level: 4

Mol. Weight: 1198.4 g/mol

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1198.4 g/mol

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC(OC7)CCC7OC8CCCCO8

Level: 3

Mol. Weight: 1198.4 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC(OCCC6)C6OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1198.4 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC(C6OC7CCCCO7)OCC(C6)OC8CCCCO8

Level: 3

Mol. Weight: 1198.4 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CC(COC3)OC4CCCCO4

Level: 3

Mol. Weight: 1198.4 g/mol

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CC(CC5)OC7CCCCO7

Level: 2

Mol. Weight: 1198.4 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC(OCCC6)C6OC7CCCCO7

Level: 2

Mol. Weight: 1198.4 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC(OC6)CCC6OC7CCCCO7

Level: 2

Mol. Weight: 1198.4 g/mol

SMILES: O1CCCCC1OC2CC(COC2)OC3CCCCO3

Level: 2

Mol. Weight: 1198.4 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1198.4 g/mol

SMILES: O1CCC(C1=O)NC(=O)C=CC=CCC(CC2)C(CC3)C2C4CCC(C5(C346)C6)CCCC5

Level: 1

Mol. Weight: 1198.4 g/mol

SMILES: C1CCC(CC2)C1C3CCC(C4(C235)C5)CC(CC4)OC6CCCCO6

Level: 1

Mol. Weight: 1198.4 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1198.4 g/mol

SMILES: C1CCCC(C1(C234)C2)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 1198.4 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1198.4 g/mol

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 1198.4 g/mol

Antitrypanosomal

Absorption

Caco-2 (logPapp): -6.38
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 12024500480.490
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1571461459234.86

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.810
Plasma Protein Binding: 83.72
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: 1.130
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -36548636988.810
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -14923.380
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.050
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2852126729686187.000
Rat (Acute): 4.200
Rat (Chronic Oral): 6117561.170
Fathead Minnow: 3600203437382.410
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 320785177267820.625
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -178324533.750
Log(P): -20756.62
Log S: -2.8
Log(Vapor Pressure): -10563293193183.3
Melting Point: -3206605.51
pKa Acid: -76970250237.67
pKa Basic: -619223197.28

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8772
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8286
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.8220
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.8192
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7973
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7506
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7030
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7030
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7004

Download SDF