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Synagrantol A

Family: Plantae - Euphorbiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Phorbol-Type Diterpene Ester

Canonical Smiles	O=C(Cc1ccccc1)OCC1=CC2[C@H]3[C@@](C3(C)C)(OC(=O)C)[C@@H]([C@H]([C@@]2([C@@H]2[C@@](C1)(OC(=O)C)C(OC(=O)C)C(=C2)C)O)C)OC(=O)C
InChI	InChI=1S/C36H44O11/c1-19-14-28-34(46-23(5)39,31(19)44-21(3)37)17-26(18-43-29(41)16-25-12-10-9-11-13-25)15-27-30-33(7,8)36(30,47-24(6)40)32(45-22(4)38)20(2)35(27,28)42/h9-15,20,27-28,30-32,42H,16-18H2,1-8H3/t20-,27?,28+,30-,31?,32-,34-,35-,36-/m1/s1
InChIKey	JGPFYIOBZPVWHS-XAZVLMETSA-N
Formula	C₃₆H₄₄O₁₁
HBA	11
HBD	1
MW	652.74
Rotatable Bonds	8
TPSA	151.73
LogP	3.8
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	47
Formal Charge	0
Fraction CSP3	0.58
Exact Mass	652.29
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Synadenium grantii	Euphorbiaceae	Plantae	213049

Showing of synonyms

Hassan EM, Mohammed MMD, et al. (2012). Two new phorbol-type diterpene esters from Synadenium grantii Hook F. leaves. Records of Natural Products,2012,6(3),255-262. [View]

Pubchem: 162817252

No compound-protein relationship available.

SMILES: c1ccccc1CC(=O)OCC(=CC23)CC(CC=C4)C4C3CCC(C25)C5

Level: 1

Mol. Weight: 652.74 g/mol

SMILES: C12C(C1)CCC3C4C(CC=C4)CC=CC23

Level: 0

Mol. Weight: 652.74 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 652.74 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.91
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.56
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 29.2

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.57
Plasma Protein Binding: 91.64
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: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 11.81
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.15
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.7
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.44
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Toxic
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: -58343.33
Rat (Acute): 3.86
Rat (Chronic Oral): 2.61
Fathead Minnow: 92.01
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 2202.95
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 2.89
Log(P): 4.38
Log S: -5.17
Log(Vapor Pressure): -89.95
Melting Point: 183.77
pKa Acid: 6.91
pKa Basic: 1.43

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8705
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8705
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8634
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8634
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8614
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8614
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8571
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8571
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8374
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8374
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8168
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8168
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8013
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8013
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7927
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7927
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7915
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7915
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7895
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7895
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7873
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7873
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7731
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7731
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7690
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7690
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7473
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7473
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7460
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7460
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7460
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7460
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7445
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7445
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7439
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7439
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7415
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7415
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7387
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7387
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7372
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7372
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7351
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7351
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7327
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7327
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7246
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7246
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7246
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7246
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7245
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7245
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7239
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7239
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7226
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7226
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7208
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7208
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7195
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7195
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7184
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7184
Inosine-5'-monophosphate dehydrogenase	P50097	IMDH_TRIFO	Tritrichomonas foetus	2	0.7182
Inosine-5'-monophosphate dehydrogenase	P50097	IMDH_TRIFO	Tritrichomonas foetus	2	0.7182
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7173
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7173
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7166
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7166
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7149
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7149
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7144
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7144
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7097
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7097
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7084
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7084
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7080
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7080
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7075
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7075
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7075
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7075
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7067
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7067
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7056
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7056
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	2	0.7050
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	2	0.7050
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	2	0.7034
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	2	0.7034
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7030
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7030
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7028
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7028
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7027
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7027
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	2	0.7015
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	2	0.7015

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