NPASS Natural Product

Natural Product: NPC313911

Natural Product ID:	NPC313911
Common Name:	Daryamide B
IUPAC Name:	(2E,4E)-N-[3-(3-amino-3-oxopropyl)-3-hydroxy-6-oxocyclohexa-1,4-dien-1-yl]-7-methylocta-2,4-dienamide
Synonyms:
Molecular Formula:	C18H24N2O4
Standard InCHIKey:	MEGDALVBZDBGAT-BDWKERMESA-N
Standard InCHI:	InChI=1S/C18H24N2O4/c1-13(2)6-4-3-5-7-17(23)20-14-12-18(24,10-8-15(14)21)11-9-16(19)22/h3-5,7-8,10,12-13,24H,6,9,11H2,1-2H3,(H2,19,22)(H,20,23)/b4-3+,7-5+
Canonical SMILES:	CC(C/C=C/C=C/C(=NC1=CC(O)(CCC(=N)O)C=CC1=O)O)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32837	streptomyces strain cnq-085	Species	Streptomycetaceae	Bacteria				PMID[17190455]
NPO31965	Streptomyces cnq-085	Species	Streptomycetaceae	Bacteria				StreptomeDB*

Biological Activity

Activity Type	# Activity
IC50	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	9.99	ug/ml	17190455
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	125	ug/ml	17190455

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 NPC313911 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	37
0.1-0.2	271
0.2-0.3	9163
0.3-0.4	16057
0.4-0.5	4896
0.5-0.6	413
0.6-0.7	46
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC314854
0.7582	Intermediate Similarity	NPC116930
0.75	Intermediate Similarity	NPC472614
0.73	Intermediate Similarity	NPC133729
0.7125	Intermediate Similarity	NPC471022
0.7097	Intermediate Similarity	NPC472613
0.68	Remote Similarity	NPC245650
0.6667	Remote Similarity	NPC170375
0.6598	Remote Similarity	NPC205546
0.6598	Remote Similarity	NPC233273
0.6598	Remote Similarity	NPC189764
0.6598	Remote Similarity	NPC50902
0.6591	Remote Similarity	NPC471597
0.6582	Remote Similarity	NPC77891
0.6538	Remote Similarity	NPC6795
0.6514	Remote Similarity	NPC316325
0.6436	Remote Similarity	NPC313234
0.6375	Remote Similarity	NPC471023
0.6364	Remote Similarity	NPC271621
0.6364	Remote Similarity	NPC59751
0.6364	Remote Similarity	NPC27413
0.6346	Remote Similarity	NPC472615
0.625	Remote Similarity	NPC82674
0.625	Remote Similarity	NPC472616
0.619	Remote Similarity	NPC472433
0.6184	Remote Similarity	NPC184014
0.6184	Remote Similarity	NPC132669
0.6184	Remote Similarity	NPC44193
0.6184	Remote Similarity	NPC246519
0.6184	Remote Similarity	NPC14234
0.6184	Remote Similarity	NPC269800
0.6182	Remote Similarity	NPC471645
0.6173	Remote Similarity	NPC247769
0.6145	Remote Similarity	NPC187315
0.6129	Remote Similarity	NPC471595
0.6126	Remote Similarity	NPC7905
0.6126	Remote Similarity	NPC315652
0.6104	Remote Similarity	NPC471992
0.6092	Remote Similarity	NPC314678
0.6091	Remote Similarity	NPC5485
0.6053	Remote Similarity	NPC473808
0.6053	Remote Similarity	NPC303672
0.6049	Remote Similarity	NPC273614
0.6027	Remote Similarity	NPC91044
0.6026	Remote Similarity	NPC4881
0.6	Remote Similarity	NPC145032
0.6	Remote Similarity	NPC304223
0.6	Remote Similarity	NPC267340
0.6	Remote Similarity	NPC312826
0.6	Remote Similarity	NPC243539
0.6	Remote Similarity	NPC54542
0.6	Remote Similarity	NPC315915
0.5977	Remote Similarity	NPC95863
0.5934	Remote Similarity	NPC55732
0.5921	Remote Similarity	NPC195986
0.5909	Remote Similarity	NPC153660
0.5904	Remote Similarity	NPC253468
0.5904	Remote Similarity	NPC235311
0.5897	Remote Similarity	NPC471991
0.5897	Remote Similarity	NPC297020
0.5897	Remote Similarity	NPC273023
0.5882	Remote Similarity	NPC473249
0.5872	Remote Similarity	NPC175585
0.587	Remote Similarity	NPC157173
0.5867	Remote Similarity	NPC307435
0.5867	Remote Similarity	NPC267692
0.5862	Remote Similarity	NPC203819
0.5844	Remote Similarity	NPC119655
0.5843	Remote Similarity	NPC122244
0.5825	Remote Similarity	NPC265662
0.5823	Remote Similarity	NPC477049
0.5823	Remote Similarity	NPC306420
0.5823	Remote Similarity	NPC24216
0.5823	Remote Similarity	NPC261158
0.5823	Remote Similarity	NPC104138
0.581	Remote Similarity	NPC175531
0.5802	Remote Similarity	NPC150505
0.5802	Remote Similarity	NPC74617
0.5794	Remote Similarity	NPC469958
0.5769	Remote Similarity	NPC56028
0.5769	Remote Similarity	NPC163912
0.5769	Remote Similarity	NPC167759
0.5769	Remote Similarity	NPC305288
0.5769	Remote Similarity	NPC474127
0.5765	Remote Similarity	NPC129995
0.5765	Remote Similarity	NPC315141
0.575	Remote Similarity	NPC268185
0.5739	Remote Similarity	NPC296361
0.573	Remote Similarity	NPC12815
0.573	Remote Similarity	NPC215745
0.573	Remote Similarity	NPC238948
0.5729	Remote Similarity	NPC161670
0.5714	Remote Similarity	NPC263266
0.5698	Remote Similarity	NPC106613
0.5684	Remote Similarity	NPC39966
0.5684	Remote Similarity	NPC224072
0.5682	Remote Similarity	NPC4706
0.5679	Remote Similarity	NPC325734
0.5663	Remote Similarity	NPC269737
0.5663	Remote Similarity	NPC64985
0.5657	Remote Similarity	NPC320057
0.5657	Remote Similarity	NPC316186
0.5647	Remote Similarity	NPC477525
0.5632	Remote Similarity	NPC117804
0.5618	Remote Similarity	NPC316185
0.5607	Remote Similarity	NPC469598
0.5604	Remote Similarity	NPC166018
0.5604	Remote Similarity	NPC169056
0.5604	Remote Similarity	NPC225665

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC313911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	56
0.1-0.2	182
0.2-0.3	3453
0.3-0.4	4723
0.4-0.5	690
0.5-0.6	49
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6667	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7500	Approved
0.6392	Remote Similarity	NPD2252	Approved
0.6392	Remote Similarity	NPD2251	Approved
0.614	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7623	Phase 3
0.5904	Remote Similarity	NPD1984	Approved
0.5882	Remote Similarity	NPD7746	Phase 1
0.5882	Remote Similarity	NPD3709	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7747	Phase 1
0.5859	Remote Similarity	NPD6094	Approved
0.5859	Remote Similarity	NPD6095	Approved
0.5789	Remote Similarity	NPD7505	Discontinued
0.5769	Remote Similarity	NPD9652	Approved

Structure

CID313911 OpenBabel06191716122D 24 24 0 0 1 0 0 0 0 0999 V2000 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 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 6.0000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -1.8660 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 -2.7321 -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 2.5981 6.5000 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 -4.2321 -1.8660 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 -1.7321 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 -2.7321 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 -2.2321 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 20 2 3 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	16099484
ChEMBL	CHEMBL464104
ZINC

Physicochemical Properties

Molecular Weight:	332.17
ALogP:	0.9645
MLogP:	2.78
XLogP:	2.969
# Rotatable Bonds:	13
Polar Surface Area:	113.97
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	24

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