NPASS Natural Product

Natural Product: NPC192192

Natural Product ID:	NPC192192
Common Name:	Hopane-6Beta,11Alpha,22,27-Tetraol
IUPAC Name:	(3S,3aS,5aS,5bR,7R,7aS,11aS,11bR,12R,13aR,13bS)-5a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5b,8,8,11a,13b-pentamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysene-7,12-diol
Synonyms:	Hopane-6Beta,11Alpha,22,27-Tetraol
Molecular Formula:	C30H52O4
Standard InCHIKey:	JRAYNDRWHLVRPV-ZEZQLZSKSA-N
Standard InCHI:	InChI=1S/C30H52O4/c1-25(2)11-8-12-28(6)23(25)21(33)16-29(7)24(28)20(32)15-22-27(5)13-9-18(26(3,4)34)19(27)10-14-30(22,29)17-31/h18-24,31-34H,8-17H2,1-7H3/t18-,19-,20+,21+,22+,23-,24+,27-,28-,29+,30-/m0/s1
Canonical SMILES:	OC[C@@]12CC[C@@H]3[C@]([C@H]1C[C@H]([C@H]1[C@@]2(C)C[C@@H](O)[C@@H]2[C@]1(C)CCCC2(C)C)O)(C)CC[C@@H]3C(O)(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
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	Eukaryota	mycelium			PMID[21473608]
NPO32716	conoideocrella tenuis bcc 18627	Species	Clavicipitaceae	Eukaryota				PMID[21473608]

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Biological Activity

Activity Type	# Activity
IC50	6
MIC	1

Activity Type	# Activity
Cell Line	4
Organism	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	52000	nM	21473608
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	47000	nM	21473608
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	14000	nM	21473608
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	9800	nM	21473608
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	47000	nM	21473608
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15000	nM	21473608
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5600	nM	21473608

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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 NPC192192 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	194
0.1-0.2	2357
0.2-0.3	9003
0.3-0.4	9672
0.4-0.5	3543
0.5-0.6	3427
0.6-0.7	1937
0.7-0.8	580
0.8-0.85	99
0.85-0.9	60
0.9-0.95	12
0.95-1	5

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Similarity Score	Similarity Level	Natural Product ID
0.7945	Intermediate Similarity	NPC473552
0.7945	Intermediate Similarity	NPC111234
0.7945	Intermediate Similarity	NPC324984
0.7945	Intermediate Similarity	NPC320549
0.7945	Intermediate Similarity	NPC323900

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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 NPC192192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	3616
0.2-0.3	3611
0.3-0.4	1087
0.4-0.5	254
0.5-0.6	216
0.6-0.7	80
0.7-0.8	23
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.56	Remote Similarity	NPD5290	Discontinued
0.5604	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD3669	Approved
0.5607	Remote Similarity	NPD6649	Approved
0.5607	Remote Similarity	NPD6869	Approved

Showing 1 to 5 of 198 entries

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Structure

CID192192 OpenBabel06191715572D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.2823 1.9015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7887 1.0476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8609 -3.2454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4193 -2.4759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6482 0.9803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8002 2.3933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8241 -0.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4731 3.3294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2961 -0.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8246 -1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2966 2.8533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6490 2.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2958 0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8238 1.4278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6472 -0.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4731 -1.4263 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6488 -0.9507 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0005 1.9034 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4717 0.4752 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8241 0.4761 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4720 1.4269 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8246 1.4273 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2961 1.9020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4737 -2.3770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6485 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6484 1.9030 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8244 0.4756 0.0000 C 0 0 1 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 -1.9408 -1.8562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 2.8784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3160 -0.0125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6054 -2.7642 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 7 29 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 25 1 0 0 0 0 12 28 1 0 0 0 0 13 27 1 0 0 0 0 14 30 1 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 16 29 1 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 27 1 6 0 0 0 20 24 1 0 0 0 0 20 32 1 6 0 0 0 21 23 1 0 0 0 0 21 33 1 1 0 0 0 22 27 1 6 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 28 1 1 0 0 0 24 28 1 1 0 0 0 24 29 1 0 0 0 0 26 34 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 17 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	52951633
ChEMBL	CHEMBL1774509
ZINC

Physicochemical Properties

Molecular Weight:	476.39
ALogP:	0.0824
MLogP:	4.32
XLogP:	7.113
# Rotatable Bonds:	13
Polar Surface Area:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	34

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