NPASS Natural Product

Natural Product: NPC663

Natural Product ID:	NPC663
Common Name:	17-Epi-17-Hydroxyazadiradione
IUPAC Name:	[(5R,7R,8R,9R,10R,13R,17R)-17-(furan-3-yl)-17-hydroxy-4,4,8,10,13-pentamethyl-3,16-dioxo-5,6,7,9,11,12-hexahydrocyclopenta[a]phenanthren-7-yl] acetate
Synonyms:
Molecular Formula:	C28H34O6
Standard InCHIKey:	QXKHBVSTPRHRQV-CMBOGFGBSA-N
Standard InCHI:	InChI=1S/C28H34O6/c1-16(29)34-23-14-19-24(2,3)21(30)8-10-25(19,4)18-7-11-26(5)20(27(18,23)6)13-22(31)28(26,32)17-9-12-33-15-17/h8-10,12-13,15,18-19,23,32H,7,11,14H2,1-6H3/t18-,19+,23-,25-,26-,27-,28-/m1/s1
Canonical SMILES:	CC(=O)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@]1(C)C1=CC(=O)[C@]([C@@]1(CC3)C)(O)c1ccoc1)(C)C=CC(=O)C2(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
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds			PMID[21381696]

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Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	3
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	20000	nM	21381696
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	20000	nM	21381696
NPT2	Others	Unspecified		IC50	=	19100	nM	21381696
NPT2	Others	Unspecified		IC50	>	20000	nM	21381696
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000	nM	21381696

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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 NPC663 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	264
0.1-0.2	1090
0.2-0.3	2128
0.3-0.4	3728
0.4-0.5	7126
0.5-0.6	7649
0.6-0.7	6735
0.7-0.8	1805
0.8-0.85	162
0.85-0.9	171
0.9-0.95	30
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.85	High Similarity	NPC470996
0.85	High Similarity	NPC472672
0.8503	High Similarity	NPC82602
0.8506	High Similarity	NPC205765
0.8509	High Similarity	NPC472785

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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 NPC663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	922
0.2-0.3	2018
0.3-0.4	2614
0.4-0.5	2000
0.5-0.6	967
0.6-0.7	332
0.7-0.8	34
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6398	Remote Similarity	NPD7315	Approved
0.6398	Remote Similarity	NPD17	Approved
0.64	Remote Similarity	NPD3887	Approved
0.6402	Remote Similarity	NPD1876	Approved
0.6404	Remote Similarity	NPD8320	Phase 1

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Structure

CID663 OpenBabel06191715322D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.7919 1.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9388 -1.4443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9389 -2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5013 -2.4549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0306 -0.9924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5319 0.5224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6883 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2196 -3.4109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7694 -0.1854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3758 -2.9241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 -1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3420 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 1.4608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2202 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8437 -1.4603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3494 1.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8434 -0.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5319 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2202 -1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6878 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0637 -2.9236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3760 -0.0004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0640 -1.9494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3761 -1.9498 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8441 -0.4874 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5319 -0.4877 0.0000 C 0 0 1 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 -4.8803 0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9324 -3.4252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8680 1.4754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7699 -1.7609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3760 0.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 7 11 1 0 0 0 0 7 18 1 0 0 0 0 8 10 2 0 0 0 0 8 21 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 33 1 0 0 0 0 13 20 2 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 33 1 0 0 0 0 16 29 2 0 0 0 0 16 34 1 0 0 0 0 17 28 1 0 0 0 0 18 25 1 6 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 19 25 1 6 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 28 1 0 0 0 0 22 31 2 0 0 0 0 23 27 1 1 0 0 0 23 34 1 0 0 0 0 25 4 1 6 0 0 0 26 28 1 6 0 0 0 27 6 1 6 0 0 0 28 32 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	52951894
ChEMBL	CHEMBL1774393
ZINC

Physicochemical Properties

Molecular Weight:	466.24
ALogP:	1.0107
MLogP:	3.88
XLogP:	2.32
# Rotatable Bonds:	10
Polar Surface Area:	93.81
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	34

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