NPASS Natural Product

Natural Product: NPC152808

Natural Product ID:	NPC152808
Common Name:	(20S)-5-Ergostene-3Beta,7Alpha,16Beta,20-Tetrol
IUPAC Name:	(3S,7S,8S,9S,10R,13S,14S,16S,17R)-17-[(2S,5R)-2-hydroxy-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7,16-triol
Synonyms:
Molecular Formula:	C28H48O4
Standard InCHIKey:	NAPNLPVMHUZNFG-BHTYWNIDSA-N
Standard InCHI:	InChI=1S/C28H48O4/c1-16(2)17(3)7-12-28(6,32)25-23(31)15-21-24-20(9-11-27(21,25)5)26(4)10-8-19(29)13-18(26)14-22(24)30/h14,16-17,19-25,29-32H,7-13,15H2,1-6H3/t17-,19+,20+,21+,22-,23+,24-,25+,26+,27+,28+/m1/s1
Canonical SMILES:	O[C@H]1CC[C@]2(C(=C[C@H]([C@@H]3[C@@H]2CC[C@]2([C@H]3C[C@@H]([C@@H]2[C@](CC[C@H](C(C)C)C)(O)C)O)C)O)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
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruits	Wanyuan County, Sichuan Province, China	2007-OCT	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruit			PMID[20961091]

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Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	9.4	ug/ml	20961091
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	47.4	ug/ml	20961091

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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 NPC152808 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	117
0.1-0.2	927
0.2-0.3	3170
0.3-0.4	8591
0.4-0.5	8365
0.5-0.6	4126
0.6-0.7	3827
0.7-0.8	1473
0.8-0.85	183
0.85-0.9	80
0.9-0.95	28
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.8214	Intermediate Similarity	NPC472463
0.8214	Intermediate Similarity	NPC24504
0.8222	Intermediate Similarity	NPC107189
0.8222	Intermediate Similarity	NPC320026
0.8235	Intermediate Similarity	NPC157655

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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 NPC152808 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	1328
0.2-0.3	3957
0.3-0.4	2490
0.4-0.5	759
0.5-0.6	173
0.6-0.7	217
0.7-0.8	77
0.8-0.85	18
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
0.6633	Remote Similarity	NPD6080	Approved
0.6633	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD4790	Discontinued

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Structure

CID152808 OpenBabel06191715522D 32 35 0 0 1 0 0 0 0 0999 V2000 -2.7256 0.3001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4034 0.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2004 -1.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5332 0.4515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2412 -2.3511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5226 -1.6373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2209 1.4618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6888 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3770 0.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7344 -1.0650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3771 2.9243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6889 2.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5137 -0.2721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4122 -1.2408 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5332 2.4368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2209 2.4368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6888 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 2.4369 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 1.4619 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5332 1.4619 0.0000 C 0 0 2 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 -0.8447 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0960 2.9419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0306 2.9421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5628 -0.5049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2725 -2.2496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 12 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 17 3 1 1 0 0 0 18 26 1 0 0 0 0 19 29 1 1 0 0 0 20 24 1 0 0 0 0 20 26 1 1 0 0 0 21 24 1 0 0 0 0 21 27 1 1 0 0 0 22 24 1 0 0 0 0 22 30 1 6 0 0 0 23 25 1 0 0 0 0 23 31 1 1 0 0 0 25 27 1 0 0 0 0 25 28 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44191679
ChEMBL	CHEMBL1641928
ZINC

Physicochemical Properties

Molecular Weight:	448.36
ALogP:	0.1977
MLogP:	4.1
XLogP:	6.008
# Rotatable Bonds:	15
Polar Surface Area:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	32

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