NPASS Natural Product

Natural Product: NPC329790

Natural Product ID:	NPC329790
Common Name:	Mayamycin
IUPAC Name:	1,6,8-trihydroxy-5-[(2R,4R,5S,6R)-5-(hydroxymethyl)-6-methyl-4-(methylamino)oxan-2-yl]-3-methylbenzo[a]anthracene-7,12-dione
Synonyms:	Mayamycin
Molecular Formula:	C27H27NO7
Standard InCHIKey:	AQNPJKKYGQVMOS-BMHLXIAXSA-N
Standard InCHI:	InChI=1S/C27H27NO7/c1-11-7-14-20(18(31)8-11)23-24(26(33)21-13(25(23)32)5-4-6-17(21)30)27(34)22(14)19-9-16(28-3)15(10-29)12(2)35-19/h4-8,12,15-16,19,28-31,34H,9-10H2,1-3H3/t12-,15+,16-,19-/m1/s1
Canonical SMILES:	OC[C@@H]1[C@H](NC)C[C@@H](O[C@@H]1C)c1c(O)c2C(=O)c3c(O)cccc3C(=O)c2c2c1cc(C)cc2O
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
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria				PMID[20545334]

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Biological Activity

Activity Type	# Activity
IC50	19

Activity Type	# Activity
Cell Line	2
Organism	11
Others	6

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	300	nM	18280170
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	1250	nM	23368966
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	2500	nM	18698753
NPT167	Organism	Propionibacterium acnes	Propionibacterium acnes	IC50	=	31200	nM	10.1007/s00044-011-9693-2
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IC50	=	310	nM	22037378
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IC50	=	2500	nM	10.1007/s00044-011-9693-2
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IC50	=	2500	nM	22809409
NPT2	Others	Unspecified		IC50	=	330	nM	26042639
NPT2	Others	Unspecified		IC50	=	200	nM	23398362
NPT2	Others	Unspecified		IC50	=	150	nM	18676881

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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 NPC329790 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	195
0.1-0.2	966
0.2-0.3	2254
0.3-0.4	6214
0.4-0.5	6947
0.5-0.6	5645
0.6-0.7	6796
0.7-0.8	1856
0.8-0.85	16
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
0.7529	Intermediate Similarity	NPC13715
0.7529	Intermediate Similarity	NPC49282
0.7529	Intermediate Similarity	NPC471683
0.7538	Intermediate Similarity	NPC83019
0.754	Intermediate Similarity	NPC327005

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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 NPC329790 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	625
0.2-0.3	1044
0.3-0.4	2004
0.4-0.5	2744
0.5-0.6	1734
0.6-0.7	725
0.7-0.8	108
0.8-0.85	21
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
0.6828	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3450	Approved
0.6829	Remote Similarity	NPD3452	Approved
0.6833	Remote Similarity	NPD6666	Approved
0.6833	Remote Similarity	NPD6667	Approved

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Structure

NPC329790 OpenBabel07101718292D 35 39 0 0 1 0 0 0 0 0999 V2000 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 -0.8660 3.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 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 -0.8660 1.5000 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 -2.5981 -1.5000 0.0000 C 0 0 2 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 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 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 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 1.7321 2.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 1.7321 -1.0000 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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 28 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 13 1 0 0 0 0 6 17 2 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 18 2 0 0 0 0 9 16 1 0 0 0 0 9 19 1 0 0 0 0 10 29 1 0 0 0 0 12 2 1 1 0 0 0 12 15 1 0 0 0 0 12 35 1 0 0 0 0 13 21 2 0 0 0 0 13 25 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 16 28 1 1 0 0 0 17 21 1 0 0 0 0 17 30 1 0 0 0 0 18 20 1 0 0 0 0 18 31 1 0 0 0 0 19 22 1 1 0 0 0 19 35 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 25 32 2 0 0 0 0 26 33 2 0 0 0 0 27 34 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	49799274
ChEMBL	CHEMBL1173035
ZINC

Physicochemical Properties

Molecular Weight:	477.18
ALogP:	-2.8814
MLogP:	3.55
XLogP:	1.654
# Rotatable Bonds:	10
Polar Surface Area:	136.32
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	35

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