ANPDB

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Caretroside A

Family: Plantae - Apocynaceae
Kingdom: Plantae
Class: Steroid
- Subclass: Pregnane Ester Glycoside

Canonical Smiles	COC1CC(O[C@H]2CC[C@]3([C@H](C2)CC[C@@]2(C3C[C@@H](OC(=O)c3ccccc3)[C@]3([C@]2(O)CC[C@@H]3C(=O)C)C)O)C)OC(C1OC1CC(OC)C(C(O1)C)O)C
InChI	InChI=1S/C42H62O12/c1-23(43)29-15-18-42(47)40(29,5)33(53-38(45)26-11-9-8-10-12-26)22-32-39(4)16-14-28(19-27(39)13-17-41(32,42)46)52-34-21-31(49-7)37(25(3)51-34)54-35-20-30(48-6)36(44)24(2)50-35/h8-12,24-25,27-37,44,46-47H,13-22H2,1-7H3/t24?,25?,27-,28-,29+,30?,31?,32?,33+,34?,35?,36?,37?,39-,40-,41-,42+/m0/s1
InChIKey	NFTYYFXBCRCCED-BGTKKIAKSA-N
Formula	C₄₂H₆₂O₁₂
HBA	12
HBD	3
MW	758.95
Rotatable Bonds	9
TPSA	159.44
LogP	4.73
Number Rings	7
Number Aromatic Rings	1
Heavy Atom Count	54
Formal Charge	0
Fraction CSP3	0.81
Exact Mass	758.42
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Caralluma retrospiciens	Apocynaceae	Plantae	197251

Showing of synonyms

Halim AF and Khalil AT. (1996). Pregnane glycosides from Caralluma retrospiciens. Phytochemistry,1996,42(4),1135-1139. [View] [PubMed]

Pubchem: 163013411

Nmrshiftdb2: 70105657

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CCC5C4CCC(C5)OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 758.95 g/mol

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CCC5C4CCC(C5)OC6CCCCO6

Level: 2

Mol. Weight: 758.95 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC(OC5)CCC5OC6CCCCO6

Level: 2

Mol. Weight: 758.95 g/mol

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CC4C3CCC5C4CCCC5

Level: 1

Mol. Weight: 758.95 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 758.95 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 758.95 g/mol

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 758.95 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 758.95 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 758.95 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.3
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 12.410
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2307.02

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.640
Plasma Protein Binding: 91.32
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: 3.970
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -58.380
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.770
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.260
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: Toxic
T. Pyriformis: -4189592.920
Rat (Acute): 5.080
Rat (Chronic Oral): 2.560
Fathead Minnow: 5294.450
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 468584.080
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 4.470
Log(P): 4.36
Log S: -5.06
Log(Vapor Pressure): -15347.25
Melting Point: 182.98
pKa Acid: -67.41
pKa Basic: 3.85

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.8401
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.8401
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8332
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8332
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8195
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8195
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8034
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8034
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7992
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7992
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7752
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7752
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7721
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7721
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7633
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7633
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7531
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7531
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7487
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7487
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7416
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7416
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7405
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7405
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7330
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7330
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7278
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7278
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7229
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7229
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7184
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7184
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7158
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7158
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7149
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7149
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7094
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7094
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7050
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7050
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7034
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7034
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7013
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7013

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