NPASS Natural Product

Natural Product: NPC229166

Natural Product ID:	NPC229166
Common Name:	Cassythicine
IUPAC Name:
Synonyms:	Cassythicine; N-Methylactinodaphnine
Molecular Formula:	C19H19NO4
Standard InCHIKey:	MPWZJVCAMFAIGV-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-20-4-3-10-7-16-19(24-9-23-16)18-12-8-15(22-2)14(21)6-11(12)5-13(20)17(10)18/h6-8,13,21H,3-5,9H2,1-2H3/t13-/m0/s1
Canonical SMILES:	COc1cc2c(cc1O)C[C@H]1c3c2c2OCOc2cc3CCN1C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10161	Macaranga pleiostemona	Species	Euphorbiaceae	Eukaryota	UNPD*
NPO11706	Gordonia terrae	Species	Gordoniaceae	Bacteria	UNPD*
NPO11817	Seiridium cardinale	Species	Sporocadaceae	Eukaryota	UNPD*
NPO1187	Baccharis scandens	Species	Asteraceae	Eukaryota	UNPD*
NPO11948	Ferulago sylvatica	Species	Apiaceae	Eukaryota	UNPD*
NPO12080	Metrodorea flavida	Species	Rutaceae	Eukaryota	UNPD*
NPO12193	Metadina trichotoma	Species	Rubiaceae	Eukaryota	UNPD*
NPO12316	Pterospermum lanceolatum	Species	Malvaceae	Eukaryota	UNPD*
NPO13118	Paeonia officinalis	Species	Paeoniaceae	Eukaryota	UNPD*
NPO15978	Nalanthamala diospyri	Species	Nectriaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
ED50	14
Others	19

Activity Type	# Activity
Cell Line	8
Organism	2
Others	20
Tissue	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	9.8	ug/ml	8254346
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	8.9	ug/ml	8254346
NPT168	Cell Line	P388	Mus musculus	ED50	>	5	ug/ml	8254346
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	112.9	%	9214740
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	225	%	9214740
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	98.9	%	9214740
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	47000	nM	9584402
NPT2	Others	Unspecified		Activity	=	0	%	9677264
NPT2	Others	Unspecified		Activity	=	68.1	%	9677264
NPT2	Others	Unspecified		Activity	=	0	%	9214740

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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 NPC229166 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	245
0.1-0.2	1181
0.2-0.3	3663
0.3-0.4	8182
0.4-0.5	4361
0.5-0.6	7747
0.6-0.7	4529
0.7-0.8	621
0.8-0.85	189
0.85-0.9	93
0.9-0.95	53
0.95-1	25

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Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC119649
0.8333	Intermediate Similarity	NPC235143
0.8343	Intermediate Similarity	NPC474745
0.8343	Intermediate Similarity	NPC220961
0.8344	Intermediate Similarity	NPC219162

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 NPC229166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	694
0.2-0.3	940
0.3-0.4	2028
0.4-0.5	2656
0.5-0.6	1827
0.6-0.7	677
0.7-0.8	140
0.8-0.85	20
0.85-0.9	2
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.689	Remote Similarity	NPD4111	Phase 1
0.689	Remote Similarity	NPD4665	Approved
0.689	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1914	Approved
0.6895	Remote Similarity	NPD7549	Discontinued

Showing 1 to 5 of 200 entries

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Structure

CID229166 OpenBabel06191716022D 24 28 0 0 1 0 0 0 0 0999 V2000 2.5935 4.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8440 -1.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1978 3.6777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9956 4.1374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6067 2.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4162 0.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6075 2.2829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8137 -0.0402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9166 -0.0963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1931 2.7474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6027 1.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8014 0.8921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8038 2.7505 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4285 -0.0189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6273 -0.4957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6066 1.3624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9913 2.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9985 1.3557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1916 0.9015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7938 3.6766 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2363 -0.4711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6395 -1.4213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2915 0.7457 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 20 1 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 3 10 1 0 0 0 0 4 20 1 0 0 0 0 5 11 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 12 18 1 0 0 0 0 13 5 1 1 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	442194
ChEMBL	CHEMBL464528
ZINC

Physicochemical Properties

Molecular Weight:	325.13
ALogP:	-0.4201
MLogP:	3
XLogP:	1.645
# Rotatable Bonds:	4
Polar Surface Area:	51.16
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	24

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