ANPDB

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Dipandensin A

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Cycloalkene
- Subclass: Seco-Cyclohexene Derivative

Canonical Smiles	CO[C@H]1[C@H](OC(=O)C)C(=CC2C1[C@@H]1C=C[C@]2([C@H]([C@@H]1OC)OC(=O)C)COC(=O)c1ccccc1)COC(=O)c1ccccc1
InChI	InChI=1S/C34H36O10/c1-20(35)43-28-24(18-41-32(37)22-11-7-5-8-12-22)17-26-27(30(28)40-4)25-15-16-34(26,31(29(25)39-3)44-21(2)36)19-42-33(38)23-13-9-6-10-14-23/h5-17,25-31H,18-19H2,1-4H3/t25-,26?,27?,28+,29+,30+,31-,34-/m0/s1
InChIKey	VROYBSLRJNHTIE-VVPMYEMNSA-N
Formula	C₃₄H₃₆O₁₀
HBA	10
HBD	0
MW	604.65
Rotatable Bonds	10
TPSA	123.66
LogP	3.95
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.41
Exact Mass	604.23
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Uvaria pandensis	Annonaceae	Plantae	673193

Showing of synonyms

Maeda G, Gilissen PJ, et al. (2021). Oxygenated Cyclohexene Derivatives from the Stem and Root Barks of Uvaria pandensis. Journal of natural products,2021, 84(12), 3080-3089. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC(=C2)CCC(C(C=C3)CC4)C2C34COC(=O)c5ccccc5

Level: 2

Mol. Weight: 604.65 g/mol

SMILES: c1ccccc1C(=O)OCC23C4C(C(C=C2)CC3)CCC=C4

Level: 1

Mol. Weight: 604.65 g/mol

SMILES: c1ccccc1C(=O)OCC(=C2)CCC3C(CC4)C=CC4C23

Level: 1

Mol. Weight: 604.65 g/mol

SMILES: C12C3C=CC(CC3)C2CCC=C1

Level: 0

Mol. Weight: 604.65 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 604.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.9
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.520
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 16.78

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 82.31
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Non-Inhibitor

Excretion

Clearance: 11.700
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.360
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.510
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.480
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: Safe
T. Pyriformis: -35767.210
Rat (Acute): 3.730
Rat (Chronic Oral): 3.060
Fathead Minnow: 65.290
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 528.120
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 4.060
Log(P): 5.15
Log S: -5.58
Log(Vapor Pressure): -25.84
Melting Point: 150.82
pKa Acid: 8.58
pKa Basic: 0.17

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9374
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9019
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8571
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8554
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8477
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8473
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8419
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.8329
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8291
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8155
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8148
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8097
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8040
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7990
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7839
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7831
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7792
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7762
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7704
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7689
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7682
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7638
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7584
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7577
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7546
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7545
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7533
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7528
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7514
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7509
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	3	0.7488
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7457
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7445
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7444
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7440
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7416
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7415
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7403
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7391
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7387
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7371
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7356
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7345
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7332
Pol protein	Q000H7	Q000H7_9HIV1	Human immunodeficiency virus 1	3	0.7330
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7323
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7315
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7305
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7300
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7269
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7257
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7239
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7236
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7232
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7230
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7229
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7221
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7220
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7215
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7201
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7181
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7161
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7155
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7148
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	4	0.7135
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7133
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7121
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7117
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7117
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7115
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7104
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7104
Nitric oxide synthase, inducible	P35228	NOS2_HUMAN	Homo sapiens	2	0.7090
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	2	0.7088
Beta-secretase 2	Q9Y5Z0	BACE2_HUMAN	Homo sapiens	2	0.7076
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7073
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7072
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7072
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7070
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7060
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	4	0.7053
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	2	0.7039
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7026
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7016
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7012
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7006
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7006

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