NPASS Natural Product

Natural Product: NPC192456

Natural Product ID:	NPC192456
Common Name:	(3S,5S,8R,9S,10S,13S,14S,17R)-10,13-Dimethyl-17-[(1S)-1-[(3R)-3-Methyl-2,3,4,5-Tetrahydropyridin-6-Yl]Ethyl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-Tetradecahydro-1H-Cyclopenta[A]Phenanthren-3-Ol
IUPAC Name:	(3S,5S,8R,9S,10S,13S,14S,17R)-10,13-dimethyl-17-[(1S)-1-[(3R)-3-methyl-2,3,4,5-tetrahydropyridin-6-yl]ethyl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Molecular Formula:	C27H45NO
Standard InCHIKey:	MSKAAWFUKWQOQS-YNAJWQGRSA-N
Standard InCHI:	InChI=1S/C27H45NO/c1-17-5-10-25(28-16-17)18(2)22-8-9-23-21-7-6-19-15-20(29)11-13-26(19,3)24(21)12-14-27(22,23)4/h17-24,29H,5-16H2,1-4H3/t17-,18+,19+,20+,21+,22-,23+,24+,26+,27-/m1/s1
Canonical SMILES:	O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](C1=NC[C@@H](CC1)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
NPO23021	Solanum congestiflorum	Species	Solanaceae	Eukaryota				PMID[21905650]

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Biological Activity

Activity Type	# Activity
GI50	60

Activity Type	# Activity
Cell Line	60

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	GI50	3681.29	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	12971.79	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50	1364.58	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50	2454.71	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	30902.95	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	14125.38	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	2760.58	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	20137.24	nM	PubChem BioAssay data set
NPT306	Cell Line	PC-3	Homo sapiens	GI50	10092.53	nM	PubChem BioAssay data set
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	12735.03	nM	PubChem BioAssay data set

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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 NPC192456 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	66
0.1-0.2	1223
0.2-0.3	14683
0.3-0.4	7759
0.4-0.5	4688
0.5-0.6	1989
0.6-0.7	436
0.7-0.8	41
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.6437	Remote Similarity	NPC472503
0.6444	Remote Similarity	NPC472742
0.6444	Remote Similarity	NPC475727
0.6444	Remote Similarity	NPC49599
0.6444	Remote Similarity	NPC220379

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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 NPC192456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	83
0.1-0.2	1007
0.2-0.3	5305
0.3-0.4	2128
0.4-0.5	480
0.5-0.6	113
0.6-0.7	39
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5612	Remote Similarity	NPD4786	Approved
0.5625	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD8171	Discontinued
0.5632	Remote Similarity	NPD4224	Phase 2
0.5636	Remote Similarity	NPD8040	Discontinued

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Structure

CID192456 OpenBabel06191715582D 29 33 0 0 1 0 0 0 0 0999 V2000 -6.5169 -4.6198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6212 -0.5742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8759 0.5057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4110 -0.9586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3404 -2.9404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 -1.4639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3797 -2.9273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5351 -3.4149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7673 -2.1517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 1.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6899 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5351 -0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6901 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9742 -3.9330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9438 -3.8311 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2247 -1.4648 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8452 -0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8452 -1.4640 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3803 -1.9523 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6904 -1.9520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8452 -0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7977 -2.2536 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 -2.5351 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4012 -3.1442 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5559 1.4750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 10 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 19 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 1 1 6 0 0 0 18 2 1 1 0 0 0 18 22 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 6 0 0 0 20 29 1 6 0 0 0 21 7 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 28 2 0 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	258526
ChEMBL	CHEMBL1966977
ZINC

Physicochemical Properties

Molecular Weight:	399.35
ALogP:	1.0894
MLogP:	4.21
XLogP:	8.016
# Rotatable Bonds:	7
Polar Surface Area:	32.59
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	29

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