NPASS Natural Product

Natural Product: NPC87351

Natural Product ID:	NPC87351
Common Name:	2-Deoxycucurbitacin D
IUPAC Name:	(8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:	2-Deoxycucurbitacin D
Molecular Formula:	C30H44O6
Standard InCHIKey:	KMFVVUWIGLRRLZ-NTLQYXAJSA-N
Standard InCHI:	InChI=1S/C30H44O6/c1-25(2,35)14-13-22(33)30(8,36)24-19(31)15-27(5)20-11-9-17-18(10-12-21(32)26(17,3)4)29(20,7)23(34)16-28(24,27)6/h9,13-14,18-20,24,31,35-36H,10-12,15-16H2,1-8H3/b14-13+/t18-,19-,20+,24+,27+,28-,29+,30+/m1/s1
Canonical SMILES:	O[C@@H]1C[C@@]2([C@]([C@H]1[C@](C(=O)/C=C/C(O)(C)C)(O)C)(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1CCC(=O)C2(C)C)C)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10443	Sloanea zuliaensis	Species	Elaeocarpaceae	Eukaryota				PMID[14640532]

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Biological Activity

Activity Type	# Activity
GI50	3

Activity Type	# Activity
Cell Line	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	210	nM	8350085
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	32	nM	9392880
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	41	nM	15620251

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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 NPC87351 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	140
0.1-0.2	778
0.2-0.3	2764
0.3-0.4	6207
0.4-0.5	9559
0.5-0.6	4959
0.6-0.7	4350
0.7-0.8	1837
0.8-0.85	207
0.85-0.9	82
0.9-0.95	3
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.8211	Intermediate Similarity	NPC476426
0.8218	Intermediate Similarity	NPC18319
0.8218	Intermediate Similarity	NPC474938
0.8218	Intermediate Similarity	NPC126815
0.8218	Intermediate Similarity	NPC474785

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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 NPC87351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1188
0.2-0.3	3513
0.3-0.4	2827
0.4-0.5	928
0.5-0.6	201
0.6-0.7	170
0.7-0.8	107
0.8-0.85	63
0.85-0.9	17
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6931	Remote Similarity	NPD6695	Phase 3
0.697	Remote Similarity	NPD4822	Approved
0.697	Remote Similarity	NPD4819	Approved
0.697	Remote Similarity	NPD4820	Approved
0.697	Remote Similarity	NPD7514	Phase 3

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Structure

NPC87351 OpenBabel07101718332D 36 39 0 0 1 0 0 0 0 0999 V2000 -2.9855 -2.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2424 -3.3087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0032 -1.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 -1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0563 -2.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0345 -2.3305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -2.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3435 -1.3795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2111 -0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 15 27 1 0 0 0 0 16 23 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 29 1 6 0 0 0 19 24 1 0 0 0 0 19 31 1 1 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 26 1 0 0 0 0 21 32 2 0 0 0 0 22 30 1 0 0 0 0 22 33 2 0 0 0 0 23 29 1 0 0 0 0 23 34 2 0 0 0 0 24 28 1 6 0 0 0 24 30 1 0 0 0 0 25 35 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 6 0 0 0 30 36 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	21597452
ChEMBL	CHEMBL493647
ZINC

Physicochemical Properties

Molecular Weight:	500.31
ALogP:	1.044
MLogP:	4.1
XLogP:	2.32
# Rotatable Bonds:	15
Polar Surface Area:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	36

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