NPASS Natural Product

Natural Product: NPC264245

Natural Product ID:	NPC264245
Common Name:	Cholesta-5,23(E)-Dien-3Beta,25-Diol
IUPAC Name:	(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Molecular Formula:	C27H44O2
Standard InCHIKey:	CRBBVTAXSNJDMS-HUYSPLOCSA-N
Standard InCHI:	InChI=1S/C27H44O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h6,8,14,18,20-24,28-29H,7,9-13,15-17H2,1-5H3/b14-6+/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
Canonical SMILES:	O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](C/C=C/C(O)(C)C)C)C)C1)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
NPO25032	Haliclona oculata	Species	Chalinidae	Eukaryota				UNPD*
NPO33302	galaxaura marginata	Species	Galaxauraceae	Eukaryota				PMID[8984148]

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Biological Activity

Activity Type	# Activity
ED50	4

Activity Type	# Activity
Cell Line	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.6	ug/ml	8984148
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.15	ug/ml	8984148
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.08	ug/ml	8984148
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.61	ug/ml	8984148

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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 NPC264245 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	103
0.1-0.2	822
0.2-0.3	3123
0.3-0.4	9710
0.4-0.5	7584
0.5-0.6	4528
0.6-0.7	3393
0.7-0.8	1236
0.8-0.85	222
0.85-0.9	87
0.9-0.95	66
0.95-1	15

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Similarity Score	Similarity Level	Natural Product ID
0.8415	Intermediate Similarity	NPC248886
0.8415	Intermediate Similarity	NPC201852
0.8421	Intermediate Similarity	NPC145498
0.8427	Intermediate Similarity	NPC288970
0.8434	Intermediate Similarity	NPC59453

Showing 1 to 5 of 200 entries

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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 NPC264245 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	129
0.1-0.2	1154
0.2-0.3	3846
0.3-0.4	2629
0.4-0.5	882
0.5-0.6	203
0.6-0.7	216
0.7-0.8	68
0.8-0.85	25
0.85-0.9	7
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6512	Remote Similarity	NPD4732	Discontinued
0.6517	Remote Similarity	NPD4268	Approved
0.6517	Remote Similarity	NPD4271	Approved
0.6526	Remote Similarity	NPD4518	Approved
0.6531	Remote Similarity	NPD7748	Approved

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Structure

CID264245 OpenBabel06191716062D 29 32 0 0 1 0 0 0 0 0999 V2000 -2.8066 3.7112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3567 6.1648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4583 5.1959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5343 2.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7443 3.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3479 3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 -1.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6888 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2220 1.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2217 0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8450 1.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1720 4.7026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6896 1.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3790 2.9229 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6882 -0.9747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6891 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3787 1.9488 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5338 0.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8447 0.4873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5685 5.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5340 1.4614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5544 -1.4744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9961 6.3807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 7 1 0 0 0 0 6 14 2 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 1 1 1 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 20 28 1 6 0 0 0 21 9 1 1 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 6 0 0 0 23 27 1 6 0 0 0 24 26 1 6 0 0 0 25 29 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	6440210
ChEMBL	CHEMBL462741
ZINC

Physicochemical Properties

Molecular Weight:	400.33
ALogP:	1.4227
MLogP:	4.21
XLogP:	7.996
# Rotatable Bonds:	11
Polar Surface Area:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	29

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