NPASS Natural Product

Natural Product: NPC473225

Natural Product ID:	NPC473225
Common Name:	Hydroxyhopanone
IUPAC Name:	(3S,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-2,3,3a,4,5,6,7,7a,10,11,11b,12,13,13a-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
Synonyms:	Hydroxyhopanone
Molecular Formula:	C30H50O2
Standard InCHIKey:	NVNUNRUPWXZKAL-RVUONTCYSA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-25(2)21-13-18-30(8)23(28(21,6)16-14-24(25)31)10-9-22-27(5)15-11-19(26(3,4)32)20(27)12-17-29(22,30)7/h19-23,32H,9-18H2,1-8H3/t19-,20?,21-,22+,23+,27-,28-,29+,30+/m0/s1
Canonical SMILES:	O=C1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CCC1[C@]2(C)CC[C@@H]1C(O)(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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	Floral spikes			PMID[17346076]

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Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	4
Organism	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000	nM	15497933
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	IC50	=	5	ug/ml	26358281
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	7	ug/ml	10.6019/CHEMBL1201861
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	77100	nM	10514334
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000	nM	25581396
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100000	nM	18809939

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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 NPC473225 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	155
0.1-0.2	1985
0.2-0.3	10680
0.3-0.4	7932
0.4-0.5	4496
0.5-0.6	3550
0.6-0.7	1685
0.7-0.8	303
0.8-0.85	74
0.85-0.9	28
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.747	Intermediate Similarity	NPC474719
0.75	Intermediate Similarity	NPC20466
0.75	Intermediate Similarity	NPC478228
0.7531	Intermediate Similarity	NPC264317
0.7531	Intermediate Similarity	NPC294438

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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 NPC473225 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	3180
0.2-0.3	3987
0.3-0.4	1098
0.4-0.5	284
0.5-0.6	222
0.6-0.7	101
0.7-0.8	30
0.8-0.85	5
0.85-0.9	9
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5714	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6869	Approved
0.5714	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD6649	Approved

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Structure

NPC473225 OpenBabel07101719252D 32 36 0 0 1 0 0 0 0 0999 V2000 3.0143 0.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5008 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5516 -3.6372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8285 -2.9861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1321 0.4024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0251 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4532 -0.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4532 -1.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5279 -1.4595 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6852 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5279 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7539 -2.6855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 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 3.3705 2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7056 -2.8878 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 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 27 1 0 0 0 0 21 25 1 0 0 0 0 21 28 1 6 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 31 2 0 0 0 0 26 32 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	44421644
ChEMBL	CHEMBL374628
ZINC

Physicochemical Properties

Molecular Weight:	442.38
ALogP:	2.7023
MLogP:	4.54
XLogP:	9.934
# Rotatable Bonds:	10
Polar Surface Area:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	32

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