NPASS Natural Product

Natural Product: NPC23593

Natural Product ID:	NPC23593
Common Name:	Methyl (1R,2R,3S,3Ar,8Bs)-3A-(1,3-Benzodioxol-5-Yl)-1,8B-Dihydroxy-6,8-Dimethoxy-3-Phenyl-2,3-Dihydro-1H-Cyclopenta[B][1]Benzofuran-2-Carboxylate
IUPAC Name:	methyl (1R,2R,3S,3aR,8bS)-3a-(1,3-benzodioxol-5-yl)-1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
Synonyms:
Molecular Formula:	C28H26O9
Standard InCHIKey:	SAGBWAVFZFVBBQ-GWNOIRNCSA-N
Standard InCHI:	InChI=1S/C28H26O9/c1-32-17-12-20(33-2)24-21(13-17)37-28(16-9-10-18-19(11-16)36-14-35-18)23(15-7-5-4-6-8-15)22(26(30)34-3)25(29)27(24,28)31/h4-13,22-23,25,29,31H,14H2,1-3H3/t22-,23-,25-,27+,28+/m1/s1
Canonical SMILES:	COC(=O)[C@@H]1[C@@H](c2ccccc2)[C@]2([C@]([C@@H]1O)(O)c1c(O2)cc(cc1OC)OC)c1ccc2c(c1)OCO2
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO13294	Pinus yunnanensis	Species	Pinaceae	Eukaryota	UNPD*
NPO18130.1	Erophaca baetica subsp. baetica	Subspecies	Fabaceae	Eukaryota	UNPD*
NPO18179	Leucopaxillus amarus	Species	Tricholomataceae	Eukaryota	UNPD*
NPO19682	Duguetia chrysocarpa	Species	Annonaceae	Eukaryota	UNPD*
NPO20222	Franseria ambrosioides	NA	NA	NA	UNPD*
NPO20667	Cereus queretaroensis	Species	Sagartiidae	Eukaryota	UNPD*
NPO21152	Senecio asper	Species	Asteraceae	Eukaryota	UNPD*
NPO21632	Chlorobium phaeovibrioides	Species	Chlorobiaceae	Bacteria	UNPD*
NPO22318	Sechium edule	Species	Cucurbitaceae	Eukaryota	UNPD*
NPO23092	Ammodendron karelinii	Species	Fabaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
ED50	3
GI50	60

Activity Type	# Activity
Cell Line	61
Individual Protein	1
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	GI50		5	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		5	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		6.295	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		5	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.002	nM	23301897
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		5.395	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		20.7	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		5	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50		8.147	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		ED50	>	0.05	nM	23301897

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Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC23593 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	1159
0.2-0.3	2385
0.3-0.4	4780
0.4-0.5	7149
0.5-0.6	4623
0.6-0.7	4273
0.7-0.8	5730
0.8-0.85	437
0.85-0.9	30
0.9-0.95	11
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.8161	Intermediate Similarity	NPC55121
0.8161	Intermediate Similarity	NPC285108
0.8161	Intermediate Similarity	NPC33298
0.8161	Intermediate Similarity	NPC127782
0.8161	Intermediate Similarity	NPC476011

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Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC23593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	843
0.2-0.3	1820
0.3-0.4	2599
0.4-0.5	2015
0.5-0.6	999
0.6-0.7	449
0.7-0.8	108
0.8-0.85	5
0.85-0.9	5
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6647	Remote Similarity	NPD3018	Phase 2
0.6649	Remote Similarity	NPD5953	Discontinued
0.665	Remote Similarity	NPD7497	Discontinued
0.665	Remote Similarity	NPD7698	Approved
0.665	Remote Similarity	NPD7696	Phase 3

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Structure

CID23593 OpenBabel06191715352D 37 42 0 0 1 0 0 0 0 0999 V2000 0.7849 -3.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2703 -0.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0918 4.7053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1152 4.0383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2335 4.3803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2598 3.1038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4966 3.7878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5228 2.5113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5966 1.6674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5323 1.4685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2521 0.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4854 -1.4127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8475 -1.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6017 -0.7816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6412 2.8533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9566 0.9566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6698 -1.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8279 0.5588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1878 -0.1521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4787 -0.4670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8409 -0.4786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8156 2.3920 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.9134 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6565 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6565 1.9134 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8094 3.3376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6565 0.9566 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9566 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5015 2.4048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5990 3.8578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6339 0.9566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6770 -2.9256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3709 0.0564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0360 3.7613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7017 0.1697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1235 0.0468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 33 1 0 0 0 0 3 34 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 21 2 0 0 0 0 14 35 1 0 0 0 0 14 36 1 0 0 0 0 15 23 1 0 0 0 0 17 32 1 0 0 0 0 18 19 2 0 0 0 0 18 35 1 0 0 0 0 19 36 1 0 0 0 0 20 24 2 0 0 0 0 20 33 1 0 0 0 0 21 24 1 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 22 26 1 1 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 25 27 1 1 0 0 0 25 29 1 0 0 0 0 26 30 2 0 0 0 0 26 34 1 0 0 0 0 27 28 1 6 0 0 0 27 31 1 0 0 0 0 28 16 1 6 0 0 0 28 37 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	390507
ChEMBL	CHEMBL1986494
ZINC

Physicochemical Properties

Molecular Weight:	506.16
ALogP:	-2.3656
MLogP:	3.55
XLogP:	4.879
# Rotatable Bonds:	11
Polar Surface Area:	112.91
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	37

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