NPASS Natural Product

Natural Product: NPC474458

Natural Product ID:	NPC474458
Common Name:	(1S,3R,3Ar,3A1R,6As,7S,9Ar)-7-Isothiocyanato-1,7-Dimethyl-4-Methylene-3-(2-Methylprop-1-Enyl)Dodecahydro-1H-Phenalen-3A-Ol
IUPAC Name:	(1S,3R,3aR,6aS,7S,9aR,9bR)-7-isothiocyanato-1,7-dimethyl-4-methylidene-3-(2-methylprop-1-enyl)-1,2,3,5,6,6a,8,9,9a,9b-decahydrophenalen-3a-ol
Synonyms:
Molecular Formula:	C21H31NOS
Standard InCHIKey:	DLCCUDJOTKFLKO-GUVFGCBPSA-N
Standard InCHI:	InChI=1S/C21H31NOS/c1-13(2)10-16-11-14(3)17-8-9-20(5,22-12-24)18-7-6-15(4)21(16,23)19(17)18/h10,14,16-19,23H,4,6-9,11H2,1-3,5H3/t14-,16-,17+,18-,19+,20-,21+/m0/s1
Canonical SMILES:	S=C=N[C@@]1(C)CC[C@H]2[C@@H]3[C@@H]1CCC(=C)[C@@]3(O)[C@H](C[C@@H]2C)C=C(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	=	12		19113969
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.423	ug/ml	17844994
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.797	ug/ml	19053514
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5.3	ug/ml	22749189
NPT2	Others	Unspecified		Ratio IC50	=	6.6		19687244

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 NPC474458 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	62
0.1-0.2	699
0.2-0.3	3639
0.3-0.4	15706
0.4-0.5	7570
0.5-0.6	2830
0.6-0.7	375
0.7-0.8	6
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8452	Intermediate Similarity	NPC475724
0.8095	Intermediate Similarity	NPC79704
0.7229	Intermediate Similarity	NPC94192
0.7204	Intermediate Similarity	NPC470365
0.7176	Intermediate Similarity	NPC476329
0.7143	Intermediate Similarity	NPC184919
0.7045	Intermediate Similarity	NPC470749
0.7037	Intermediate Similarity	NPC145715
0.699	Remote Similarity	NPC90538
0.6966	Remote Similarity	NPC470711
0.6966	Remote Similarity	NPC470758
0.6951	Remote Similarity	NPC473959
0.6941	Remote Similarity	NPC138409
0.6914	Remote Similarity	NPC282694
0.6914	Remote Similarity	NPC79576
0.6914	Remote Similarity	NPC194208
0.6869	Remote Similarity	NPC473314
0.6863	Remote Similarity	NPC275686
0.6854	Remote Similarity	NPC476308
0.6818	Remote Similarity	NPC201048
0.6818	Remote Similarity	NPC476366
0.679	Remote Similarity	NPC317778
0.6744	Remote Similarity	NPC476431
0.6706	Remote Similarity	NPC476135
0.6705	Remote Similarity	NPC265485
0.6705	Remote Similarity	NPC220939
0.6698	Remote Similarity	NPC55462
0.6667	Remote Similarity	NPC265588
0.663	Remote Similarity	NPC291379
0.6629	Remote Similarity	NPC100334
0.6627	Remote Similarity	NPC174956
0.6606	Remote Similarity	NPC472359
0.6596	Remote Similarity	NPC218616
0.6596	Remote Similarity	NPC296701
0.6593	Remote Similarity	NPC91594
0.6591	Remote Similarity	NPC167706
0.6591	Remote Similarity	NPC23954
0.6588	Remote Similarity	NPC279434
0.6559	Remote Similarity	NPC295131
0.6559	Remote Similarity	NPC250632
0.6556	Remote Similarity	NPC32832
0.6535	Remote Similarity	NPC243985
0.6535	Remote Similarity	NPC280710
0.6522	Remote Similarity	NPC470396
0.6522	Remote Similarity	NPC285761
0.6522	Remote Similarity	NPC22955
0.6522	Remote Similarity	NPC11908
0.6522	Remote Similarity	NPC474989
0.6522	Remote Similarity	NPC99168
0.6517	Remote Similarity	NPC182717
0.6509	Remote Similarity	NPC293299
0.6509	Remote Similarity	NPC45365
0.6505	Remote Similarity	NPC240650
0.6489	Remote Similarity	NPC476646
0.6484	Remote Similarity	NPC30590
0.6484	Remote Similarity	NPC122418
0.6484	Remote Similarity	NPC106364
0.6484	Remote Similarity	NPC237460
0.6484	Remote Similarity	NPC120098
0.6484	Remote Similarity	NPC290598
0.6484	Remote Similarity	NPC27765
0.6484	Remote Similarity	NPC265328
0.6471	Remote Similarity	NPC64123
0.6463	Remote Similarity	NPC28755
0.6463	Remote Similarity	NPC152211
0.6452	Remote Similarity	NPC273410
0.6452	Remote Similarity	NPC53744
0.6452	Remote Similarity	NPC472463
0.6452	Remote Similarity	NPC170394
0.6452	Remote Similarity	NPC80530
0.6444	Remote Similarity	NPC22134
0.6444	Remote Similarity	NPC243342
0.6444	Remote Similarity	NPC477138
0.6429	Remote Similarity	NPC81615
0.6421	Remote Similarity	NPC49964
0.6415	Remote Similarity	NPC471083
0.6415	Remote Similarity	NPC247060
0.6415	Remote Similarity	NPC50815
0.6413	Remote Similarity	NPC472805
0.6413	Remote Similarity	NPC101475
0.6413	Remote Similarity	NPC157996
0.6413	Remote Similarity	NPC471798
0.6413	Remote Similarity	NPC40394
0.6413	Remote Similarity	NPC90979
0.6413	Remote Similarity	NPC34177
0.6413	Remote Similarity	NPC132542
0.6408	Remote Similarity	NPC476903
0.6404	Remote Similarity	NPC242992
0.6395	Remote Similarity	NPC202017
0.6386	Remote Similarity	NPC311809
0.6383	Remote Similarity	NPC241290
0.6383	Remote Similarity	NPC322313
0.6383	Remote Similarity	NPC96362
0.6383	Remote Similarity	NPC209944
0.6383	Remote Similarity	NPC236237
0.6383	Remote Similarity	NPC13554
0.6383	Remote Similarity	NPC164840
0.6383	Remote Similarity	NPC102253
0.6374	Remote Similarity	NPC477923
0.6374	Remote Similarity	NPC138374
0.6374	Remote Similarity	NPC34700
0.6374	Remote Similarity	NPC291503
0.6374	Remote Similarity	NPC66566
0.6373	Remote Similarity	NPC477290
0.6364	Remote Similarity	NPC34754
0.6355	Remote Similarity	NPC474583
0.6354	Remote Similarity	NPC82623
0.6344	Remote Similarity	NPC167037
0.6344	Remote Similarity	NPC65897
0.6344	Remote Similarity	NPC83351
0.6344	Remote Similarity	NPC244385
0.6344	Remote Similarity	NPC158662
0.6344	Remote Similarity	NPC167891
0.6344	Remote Similarity	NPC138621
0.6344	Remote Similarity	NPC474216
0.6344	Remote Similarity	NPC253807
0.6344	Remote Similarity	NPC196753
0.6344	Remote Similarity	NPC85346
0.6344	Remote Similarity	NPC300499
0.6344	Remote Similarity	NPC98386
0.6344	Remote Similarity	NPC476314
0.6344	Remote Similarity	NPC312328
0.6344	Remote Similarity	NPC302041
0.6344	Remote Similarity	NPC6978
0.6344	Remote Similarity	NPC230295
0.6341	Remote Similarity	NPC474769
0.6341	Remote Similarity	NPC189290
0.6333	Remote Similarity	NPC471799
0.6333	Remote Similarity	NPC474743
0.6327	Remote Similarity	NPC261266
0.6327	Remote Similarity	NPC6391
0.6322	Remote Similarity	NPC101307
0.6322	Remote Similarity	NPC88454
0.6322	Remote Similarity	NPC117607
0.6316	Remote Similarity	NPC264245
0.6316	Remote Similarity	NPC249423
0.6316	Remote Similarity	NPC473217
0.631	Remote Similarity	NPC41160
0.6304	Remote Similarity	NPC240604
0.6304	Remote Similarity	NPC253190
0.6304	Remote Similarity	NPC189883
0.6304	Remote Similarity	NPC300324
0.6296	Remote Similarity	NPC318036
0.6292	Remote Similarity	NPC475728
0.6292	Remote Similarity	NPC145498
0.6292	Remote Similarity	NPC92801
0.6289	Remote Similarity	NPC474493
0.6289	Remote Similarity	NPC205845
0.6279	Remote Similarity	NPC258595
0.6277	Remote Similarity	NPC30986
0.6277	Remote Similarity	NPC109546
0.6277	Remote Similarity	NPC28862
0.6277	Remote Similarity	NPC143182
0.6277	Remote Similarity	NPC209430
0.6277	Remote Similarity	NPC47982
0.6277	Remote Similarity	NPC81306
0.6277	Remote Similarity	NPC84694
0.6264	Remote Similarity	NPC471797
0.6264	Remote Similarity	NPC91858
0.6264	Remote Similarity	NPC469593
0.6264	Remote Similarity	NPC469533
0.6264	Remote Similarity	NPC476736
0.6264	Remote Similarity	NPC469534
0.6264	Remote Similarity	NPC306727
0.625	Remote Similarity	NPC304285
0.625	Remote Similarity	NPC2648
0.625	Remote Similarity	NPC155521
0.625	Remote Similarity	NPC248886
0.625	Remote Similarity	NPC276616
0.625	Remote Similarity	NPC96484
0.625	Remote Similarity	NPC2524
0.625	Remote Similarity	NPC87489
0.625	Remote Similarity	NPC208999
0.625	Remote Similarity	NPC101462
0.6237	Remote Similarity	NPC470751
0.6237	Remote Similarity	NPC477924
0.6237	Remote Similarity	NPC470750
0.6237	Remote Similarity	NPC155986
0.6237	Remote Similarity	NPC318495
0.6237	Remote Similarity	NPC198968
0.6224	Remote Similarity	NPC274448
0.6224	Remote Similarity	NPC75810
0.6224	Remote Similarity	NPC152684
0.6222	Remote Similarity	NPC110799
0.6222	Remote Similarity	NPC242001
0.6222	Remote Similarity	NPC477792
0.6222	Remote Similarity	NPC164022
0.622	Remote Similarity	NPC470370
0.622	Remote Similarity	NPC470369
0.6216	Remote Similarity	NPC274895
0.6211	Remote Similarity	NPC234193
0.6207	Remote Similarity	NPC37792
0.62	Remote Similarity	NPC67872
0.6196	Remote Similarity	NPC22105
0.6196	Remote Similarity	NPC162742
0.6196	Remote Similarity	NPC141071
0.6196	Remote Similarity	NPC288035
0.6196	Remote Similarity	NPC471723
0.6196	Remote Similarity	NPC230301
0.6196	Remote Similarity	NPC185536

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	642
0.2-0.3	3203
0.3-0.4	3896
0.4-0.5	1121
0.5-0.6	198
0.6-0.7	13
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
0.67	Remote Similarity	NPD5771	Approved
0.6383	Remote Similarity	NPD7525	Registered
0.6277	Remote Similarity	NPD7645	Phase 2
0.6264	Remote Similarity	NPD4784	Approved
0.6264	Remote Similarity	NPD4785	Approved
0.6222	Remote Similarity	NPD4243	Approved
0.6196	Remote Similarity	NPD6942	Approved
0.6196	Remote Similarity	NPD7339	Approved
0.6129	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4723	Approved
0.604	Remote Similarity	NPD4722	Approved
0.6022	Remote Similarity	NPD4190	Phase 3
0.6022	Remote Similarity	NPD5275	Approved
0.5941	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6404	Discontinued
0.5773	Remote Similarity	NPD4195	Approved
0.5758	Remote Similarity	NPD3667	Approved
0.5755	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD6926	Approved
0.5745	Remote Similarity	NPD6924	Approved
0.5714	Remote Similarity	NPD6930	Phase 2
0.5714	Remote Similarity	NPD6931	Approved
0.5686	Remote Similarity	NPD4623	Approved
0.5686	Remote Similarity	NPD4519	Discontinued
0.5686	Remote Similarity	NPD3618	Phase 1
0.5684	Remote Similarity	NPD8264	Approved
0.5644	Remote Similarity	NPD4786	Approved
0.5625	Remote Similarity	NPD6933	Approved
0.5625	Remote Similarity	NPD1346	Approved
0.5619	Remote Similarity	NPD3168	Discontinued
0.5612	Remote Similarity	NPD6929	Approved
0.56	Remote Similarity	NPD4223	Phase 3
0.56	Remote Similarity	NPD4221	Approved

Structure

NPC474458 OpenBabel07101719252D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.5981 -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 -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 1.6833 2.4006 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 -0.6945 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.5860 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 2.0487 3.3314 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 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 0 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 -0.8660 1.5000 0.0000 C 0 0 2 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 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6945 2.2515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0598 3.1824 0.0000 N 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 3.0375 3.4805 0.0000 S 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 4 15 2 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 22 2 0 0 0 0 12 24 2 0 0 0 0 14 3 1 6 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 21 1 1 0 0 0 17 8 1 1 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 19 21 1 6 0 0 0 20 5 1 1 0 0 0 20 22 1 0 0 0 0 21 23 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	10569552
ChEMBL	CHEMBL469287
ZINC

Physicochemical Properties

Molecular Weight:	345.21
ALogP:	1.8142
MLogP:	3.44
XLogP:	5.057
# Rotatable Bonds:	7
Polar Surface Area:	64.68
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	24

Download Data

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General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs