NPASS Natural Product

Natural Product: NPC474456

Natural Product ID:	NPC474456
Common Name:	(1S,3Ar,3A1R,4S,6S,6As,9As)-6-(2-Isothiocyanato-2-Methylpropyl)-1,4-Dimethyl-7-Methylenedodecahydro-1H-Phenalene-1-Carbonitrile
IUPAC Name:	(1S,3aR,4S,6S,6aS,9aS,9bR)-6-(2-isothiocyanato-2-methylpropyl)-1,4-dimethyl-7-methylidene-3,3a,4,5,6,6a,8,9,9a,9b-decahydro-2H-phenalene-1-carbonitrile
Synonyms:
Molecular Formula:	C22H32N2S
Standard InCHIKey:	UAMLJAIZEUCBHU-UGLWPLIBSA-N
Standard InCHI:	InChI=1S/C22H32N2S/c1-14-6-7-18-20-17(8-9-22(18,5)12-23)15(2)10-16(19(14)20)11-21(3,4)24-13-25/h15-20H,1,6-11H2,2-5H3/t15-,16-,17+,18-,19-,20+,22+/m0/s1
Canonical SMILES:	S=C=NC(C[C@@H]1C[C@H](C)[C@@H]2[C@H]3[C@H]1C(=C)CC[C@@H]3[C@@](CC2)(C)C#N)(C)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
NPO30160	Cymbastela hooperi	Species	Axinellidae	Eukaryota				PMID[8759172]

Biological Activity

Activity Type	# Activity
IC50	3
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio IC50	>	42.6		DrugMatrix in vivo data: Pathology
NPT2	Others	Unspecified		Ratio IC50	>	183		7932574
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.47	ug/ml	PubChem BioAssay data set
NPT91	Cell Line	KB	Homo sapiens	IC50	>	20	ug/ml	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.109	ug/ml	17844994

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 NPC474456 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	136
0.1-0.2	5240
0.2-0.3	16330
0.3-0.4	7039
0.4-0.5	1923
0.5-0.6	166
0.6-0.7	30
0.7-0.8	20
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8413	Intermediate Similarity	NPC28755
0.8413	Intermediate Similarity	NPC152211
0.8095	Intermediate Similarity	NPC173815
0.8033	Intermediate Similarity	NPC474416
0.803	Intermediate Similarity	NPC475755
0.7969	Intermediate Similarity	NPC324944
0.7857	Intermediate Similarity	NPC184919
0.7727	Intermediate Similarity	NPC311809
0.7656	Intermediate Similarity	NPC318036
0.7541	Intermediate Similarity	NPC476681
0.7538	Intermediate Similarity	NPC474457
0.7313	Intermediate Similarity	NPC474420
0.7313	Intermediate Similarity	NPC474454
0.7313	Intermediate Similarity	NPC474455
0.7273	Intermediate Similarity	NPC475696
0.7273	Intermediate Similarity	NPC474528
0.7273	Intermediate Similarity	NPC474415
0.7246	Intermediate Similarity	NPC145715
0.7246	Intermediate Similarity	NPC474435
0.7246	Intermediate Similarity	NPC474027
0.7206	Intermediate Similarity	NPC317778
0.7143	Intermediate Similarity	NPC473959
0.7123	Intermediate Similarity	NPC138409
0.7083	Intermediate Similarity	NPC476135
0.7059	Intermediate Similarity	NPC475716
0.6944	Remote Similarity	NPC37792
0.6901	Remote Similarity	NPC476682
0.6795	Remote Similarity	NPC476308
0.6757	Remote Similarity	NPC476288
0.6711	Remote Similarity	NPC476329
0.6625	Remote Similarity	NPC79704
0.6571	Remote Similarity	NPC472827
0.6567	Remote Similarity	NPC476683
0.6528	Remote Similarity	NPC474086
0.6515	Remote Similarity	NPC212905
0.6494	Remote Similarity	NPC265789
0.6494	Remote Similarity	NPC21773
0.6418	Remote Similarity	NPC127944
0.6418	Remote Similarity	NPC475272
0.6393	Remote Similarity	NPC193180
0.6389	Remote Similarity	NPC219621
0.6329	Remote Similarity	NPC476904
0.6308	Remote Similarity	NPC22765
0.6286	Remote Similarity	NPC470370
0.6286	Remote Similarity	NPC470369
0.6232	Remote Similarity	NPC469770
0.623	Remote Similarity	NPC103290
0.6212	Remote Similarity	NPC472829
0.6176	Remote Similarity	NPC476679
0.6173	Remote Similarity	NPC7214
0.6145	Remote Similarity	NPC211322
0.6118	Remote Similarity	NPC283277
0.6061	Remote Similarity	NPC17518
0.6026	Remote Similarity	NPC472831
0.6023	Remote Similarity	NPC474458
0.5909	Remote Similarity	NPC152684
0.5909	Remote Similarity	NPC124851
0.5909	Remote Similarity	NPC24733
0.589	Remote Similarity	NPC21781
0.5882	Remote Similarity	NPC250632
0.5882	Remote Similarity	NPC12035
0.5873	Remote Similarity	NPC190232
0.5873	Remote Similarity	NPC105246
0.5867	Remote Similarity	NPC89921
0.5867	Remote Similarity	NPC474596
0.5854	Remote Similarity	NPC125828
0.5843	Remote Similarity	NPC56107
0.5843	Remote Similarity	NPC166458
0.5814	Remote Similarity	NPC118329
0.5814	Remote Similarity	NPC475724
0.5814	Remote Similarity	NPC152039
0.5814	Remote Similarity	NPC329782
0.5814	Remote Similarity	NPC257962
0.5775	Remote Similarity	NPC123194
0.5747	Remote Similarity	NPC472312
0.5747	Remote Similarity	NPC215474
0.5714	Remote Similarity	NPC475812
0.5714	Remote Similarity	NPC472828
0.5682	Remote Similarity	NPC171639
0.5667	Remote Similarity	NPC157479
0.5632	Remote Similarity	NPC474122
0.5625	Remote Similarity	NPC245223
0.5625	Remote Similarity	NPC124384
0.5618	Remote Similarity	NPC477289
0.5606	Remote Similarity	NPC86683
0.5604	Remote Similarity	NPC43308

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	1836
0.2-0.3	5464
0.3-0.4	1458
0.4-0.5	249
0.5-0.6	22
0.6-0.7	0
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
0.5949	Remote Similarity	NPD6939	Phase 2
0.5949	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.57	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD873	Approved
0.5692	Remote Similarity	NPD871	Approved
0.5679	Remote Similarity	NPD5365	Phase 2
0.5632	Remote Similarity	NPD8028	Phase 2

Structure

NPC474456 OpenBabel07101719252D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4763 1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6926 3.7947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3161 3.0129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 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 -0.8660 -1.5000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4763 1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2474 4.2180 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 0.6945 1.2515 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6945 1.2515 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3273 2.8638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1340 -3.2321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3964 3.2292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0983 5.2068 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 12 23 3 0 0 0 0 13 24 2 0 0 0 0 13 25 2 0 0 0 0 15 2 1 6 0 0 0 15 17 1 0 0 0 0 16 11 1 6 0 0 0 16 19 1 0 0 0 0 17 8 1 1 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 1 0 0 0 19 14 1 1 0 0 0 19 20 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44566849
ChEMBL	CHEMBL469285
ZINC

Physicochemical Properties

Molecular Weight:	356.23
ALogP:	1.7597
MLogP:	3.55
XLogP:	7.198
# Rotatable Bonds:	7
Polar Surface Area:	68.24
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	25

Download Data

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Structure MOL file
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