NPASS Natural Product

Natural Product: NPC263507

Natural Product ID:	NPC263507
Common Name:	Cryptophycin A
IUPAC Name:	(3S,6R,10R,13E,16S)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[(1S)-1-[(2R,3R)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone
Synonyms:
Molecular Formula:	C35H43ClN2O8
Standard InCHIKey:	PSNOPSMXOBPNNV-VVCTWANISA-N
Standard InCHI:	InChI=1S/C35H43ClN2O8/c1-20(2)16-29-35(42)44-27(22(4)31-32(46-31)24-10-7-6-8-11-24)12-9-13-30(39)38-26(33(40)37-19-21(3)34(41)45-29)18-23-14-15-28(43-5)25(36)17-23/h6-11,13-15,17,20-22,26-27,29,31-32H,12,16,18-19H2,1-5H3,(H,37,40)(H,38,39)/b13-9+/t21-,22+,26-,27+,29+,31-,32-/m1/s1
Canonical SMILES:	COc1ccc(cc1Cl)C[C@H]1N=C(O)/C=C/C[C@H](OC(=O)[C@@H](OC(=O)[C@@H](CN=C1O)C)CC(C)C)[C@@H]([C@H]1O[C@@H]1c1ccccc1)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	BGC0000975 ;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10879	Lasius meridionalis	Species	Formicidae	Eukaryota	UNPD*
NPO12744	Ajuga nipponensis	Species	Lamiaceae	Eukaryota	UNPD*
NPO1537	Vaccinium arctostaphylos	Species	Ericaceae	Eukaryota	UNPD*
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	UNPD*
NPO19541	Smilax moranensis	Species	Smilacaceae	Eukaryota	UNPD*
NPO1969	Streptomyces pilosus	Species	Streptomycetaceae	Bacteria	UNPD*
NPO19804	Lycopodium saururus	Species	Lycopodiaceae	Eukaryota	UNPD*
NPO23436	Cladrastis sikokiana	Species	Fabaceae	Eukaryota	UNPD*
NPO28833	Eleutherococcus sieboldianus	Species	Araliaceae	Eukaryota	UNPD*
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
ED50	5
IC50	18

Activity Type	# Activity
Cell Line	18
Individual Protein	1
Organism	1
Others	2
Protein Complex	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.0092	nM	9090872
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	0.002	nM	10.1016/0960-894X(96)00182-5
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	0.0092	nM	9090872
NPT2	Others	Unspecified		ED50	=	1.00E-06	nM	9873466
NPT2	Others	Unspecified		IC50	=	3400	nM	15214797
NPT3027	Cell Line	MCF7S	Homo sapiens	IC50	=	0.003	nM	12639575
NPT319	Cell Line	B16	Mus musculus	ED50	=	1.3	nM	9873466
NPT319	Cell Line	B16	Mus musculus	IC50	=	0.03	nM	10.1016/0960-894X(96)00182-5
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	ED50	=	0.018	nM	14736249
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	IC50	=	0.013	nM	12639575

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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 NPC263507 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	158
0.1-0.2	884
0.2-0.3	2970
0.3-0.4	8893
0.4-0.5	4736
0.5-0.6	12106
0.6-0.7	1100
0.7-0.8	31
0.8-0.85	0
0.85-0.9	1
0.9-0.95	3
0.95-1	7

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Similarity Score	Similarity Level	Natural Product ID
0.6519	Remote Similarity	NPC143892
0.6519	Remote Similarity	NPC476744
0.6519	Remote Similarity	NPC283081
0.6519	Remote Similarity	NPC299090
0.6519	Remote Similarity	NPC153644

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 NPC263507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	123
0.1-0.2	543
0.2-0.3	1004
0.3-0.4	2149
0.4-0.5	2651
0.5-0.6	2191
0.6-0.7	478
0.7-0.8	20
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6307	Remote Similarity	NPD3052	Approved
0.6307	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7495	Discontinued
0.631	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD3655	Clinical (unspecified phase)

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Structure

CID263507 OpenBabel06191716062D 46 49 0 0 1 0 0 0 0 0999 V2000 1.2149 4.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5135 3.9196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2088 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3834 -2.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2747 -4.1779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8379 -2.7693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9033 -1.7714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9411 -3.2116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0137 -2.0137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0719 -1.2158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1096 -2.6560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0898 -1.6310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0137 -2.0137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6702 -1.8939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9917 -2.8408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4488 2.4794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3103 -1.3371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0081 -0.1951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9375 2.6310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3834 3.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0137 3.0137 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4488 -1.4794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3296 -1.1420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1750 -1.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6318 -2.2840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0273 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3827 -0.9239 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9724 -3.0359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3827 1.9239 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9375 -1.6310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3457 -1.0372 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3435 -1.1026 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0273 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0137 3.0137 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 -8.6126 -2.4791 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.6447 1.9239 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6447 -0.9239 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.4931 -2.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0081 1.1951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8186 3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9808 1.1951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2939 -3.9828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0898 2.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9012 -0.2057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 5 43 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 9 13 2 0 0 0 0 10 24 2 0 0 0 0 11 24 1 0 0 0 0 12 27 1 0 0 0 0 13 30 1 0 0 0 0 14 15 2 0 0 0 0 14 23 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 37 1 0 0 0 0 21 3 1 1 0 0 0 21 34 1 0 0 0 0 22 4 1 1 0 0 0 25 28 2 0 0 0 0 25 36 1 0 0 0 0 26 18 1 6 0 0 0 26 33 1 0 0 0 0 26 38 1 0 0 0 0 27 22 1 6 0 0 0 27 44 1 0 0 0 0 28 43 1 0 0 0 0 29 16 1 1 0 0 0 29 35 1 0 0 0 0 29 45 1 0 0 0 0 30 38 2 3 0 0 0 30 39 1 0 0 0 0 31 22 1 1 0 0 0 31 32 1 0 0 0 0 31 46 1 0 0 0 0 32 24 1 6 0 0 0 32 46 1 0 0 0 0 33 37 2 3 0 0 0 33 40 1 0 0 0 0 34 41 2 0 0 0 0 34 45 1 0 0 0 0 35 42 2 0 0 0 0 35 44 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	6438401
ChEMBL	CHEMBL441018
ZINC

Physicochemical Properties

Molecular Weight:	654.27
ALogP:	1.4508
MLogP:	4.1
XLogP:	7.185
# Rotatable Bonds:	16
Polar Surface Area:	139.54
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	46

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