NPASS Natural Product

Natural Product: NPC13715

Natural Product ID:	NPC13715
Common Name:	Rabelomycin
IUPAC Name:	(3R)-3,6,8-trihydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
Synonyms:	Rabelomycin
Molecular Formula:	C19H14O6
Standard InCHIKey:	JJOLHRYZQSDLSA-LJQANCHMSA-N
Standard InCHI:	InChI=1S/C19H14O6/c1-19(25)6-8-5-11(21)15-16(13(8)12(22)7-19)17(23)9-3-2-4-10(20)14(9)18(15)24/h2-5,20-21,25H,6-7H2,1H3/t19-/m1/s1
Canonical SMILES:	Oc1cc2C[C@@](C)(O)CC(=O)c2c2c1C(=O)c1c(C2=O)cccc1O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	BGC0000223 ;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10265.2	Streptomyces tsusimaensis mi310-38f7	Subspecies	Streptomycetaceae	Bacteria	StreptomeDB*
NPO12176	Streptomyces olivaceus	Species	Streptomycetaceae	Bacteria	StreptomeDB*
NPO12176.2	Streptomyces olivaceus atcc 21549	Subspecies	Streptomycetaceae	Bacteria	StreptomeDB*
NPO12176.3	Streptomyces olivaceus atcc 21569	Subspecies	Streptomycetaceae	Bacteria	StreptomeDB*
NPO24126	Streptomyces albus	Species	Streptomycetaceae	Bacteria	StreptomeDB*
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	StreptomeDB*
NPO32086	Streptomyces atcc 21569	Species	Streptomycetaceae	Bacteria	StreptomeDB*

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Biological Activity

Activity Type	# Activity
IC50	3
MIC	5

Activity Type	# Activity
Cell Line	3
Organism	5

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	=	8	ug/ml	23136829
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1	ug/ml	23136829
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	16	ug/ml	23136829
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	64	ug/ml	23136829
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	5540	nM	23136829
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	9910	nM	23136829
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16	ug/ml	23136829
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4280	nM	23136829

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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 NPC13715 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	271
0.1-0.2	1346
0.2-0.3	2237
0.3-0.4	5906
0.4-0.5	7603
0.5-0.6	4142
0.6-0.7	5330
0.7-0.8	3571
0.8-0.85	312
0.85-0.9	127
0.9-0.95	43
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.8406	Intermediate Similarity	NPC117609
0.8406	Intermediate Similarity	NPC259942
0.8409	Intermediate Similarity	NPC285829
0.8409	Intermediate Similarity	NPC206778
0.8414	Intermediate Similarity	NPC238629

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 NPC13715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	1002
0.2-0.3	1275
0.3-0.4	2667
0.4-0.5	2257
0.5-0.6	1141
0.6-0.7	414
0.7-0.8	84
0.8-0.85	4
0.85-0.9	6
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6689	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.669	Remote Similarity	NPD9281	Approved
0.6691	Remote Similarity	NPD4750	Phase 3
0.6691	Remote Similarity	NPD3022	Approved
0.6691	Remote Similarity	NPD3021	Approved

Showing 1 to 5 of 200 entries

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Structure

CID13715 OpenBabel06191715342D 25 28 0 0 1 0 0 0 0 0999 V2000 -3.7229 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2575 -0.3912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 19 1 0 0 0 0 7 12 1 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 22 2 0 0 0 0 13 16 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 17 23 2 0 0 0 0 18 24 2 0 0 0 0 19 1 1 1 0 0 0 19 25 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	443810
ChEMBL	CHEMBL2164969
ZINC

Physicochemical Properties

Molecular Weight:	338.08
ALogP:	-1.6617
MLogP:	2.89
XLogP:	0.218
# Rotatable Bonds:	4
Polar Surface Area:	111.9
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	25

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