NPASS Natural Product

Natural Product: NPC125771

Natural Product ID:	NPC125771
Common Name:	Reticulidin A
IUPAC Name:	(2R,3R,4aR,8aR)-3-chloro-7-[(E)-2-(dichloromethylideneamino)ethenyl]-4,4,8a-trimethyl-1,2,3,4a,5,6-hexahydronaphthalen-2-ol
Synonyms:
Molecular Formula:	C16H22Cl3NO
Standard InCHIKey:	UGFPVWDJDIORFX-OWXJXJPQSA-N
Standard InCHI:	InChI=1S/C16H22Cl3NO/c1-15(2)12-5-4-10(6-7-20-14(18)19)8-16(12,3)9-11(21)13(15)17/h6-8,11-13,21H,4-5,9H2,1-3H3/b7-6+/t11-,12+,13+,16+/m1/s1
Canonical SMILES:	O[C@@H]1C[C@]2(C)C=C(CC[C@H]2C([C@H]1Cl)(C)C)/C=C/N=C(Cl)Cl
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
NPO13092	Reticulidia fungia	Species	Phyllidiidae	Eukaryota				PMID[10514331]

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.41	ug/ml	PubChem BioAssay data set
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.59	ug/ml	PubChem BioAssay data set

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 NPC125771 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	56
0.1-0.2	723
0.2-0.3	5416
0.3-0.4	15239
0.4-0.5	6908
0.5-0.6	2320
0.6-0.7	224
0.7-0.8	2
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	NPC218902
0.7172	Intermediate Similarity	NPC76164
0.7172	Intermediate Similarity	NPC153699
0.6852	Remote Similarity	NPC269713
0.6702	Remote Similarity	NPC68443
0.6702	Remote Similarity	NPC182717
0.6667	Remote Similarity	NPC106432
0.663	Remote Similarity	NPC208999
0.6596	Remote Similarity	NPC110799
0.6531	Remote Similarity	NPC307965
0.6531	Remote Similarity	NPC76931
0.6531	Remote Similarity	NPC18603
0.6531	Remote Similarity	NPC205455
0.6531	Remote Similarity	NPC318136
0.6531	Remote Similarity	NPC186191
0.6526	Remote Similarity	NPC471799
0.6495	Remote Similarity	NPC470362
0.6495	Remote Similarity	NPC134330
0.6495	Remote Similarity	NPC129165
0.6495	Remote Similarity	NPC265588
0.6489	Remote Similarity	NPC145498
0.6489	Remote Similarity	NPC92801
0.6484	Remote Similarity	NPC475812
0.6458	Remote Similarity	NPC243342
0.6458	Remote Similarity	NPC91858
0.6458	Remote Similarity	NPC100334
0.6458	Remote Similarity	NPC471797
0.6458	Remote Similarity	NPC477138
0.6452	Remote Similarity	NPC32055
0.6452	Remote Similarity	NPC216460
0.6452	Remote Similarity	NPC96484
0.6429	Remote Similarity	NPC471798
0.6421	Remote Similarity	NPC164022
0.6421	Remote Similarity	NPC242001
0.6421	Remote Similarity	NPC167706
0.6417	Remote Similarity	NPC216335
0.6413	Remote Similarity	NPC149680
0.6392	Remote Similarity	NPC291503
0.6392	Remote Similarity	NPC257347
0.6392	Remote Similarity	NPC471723
0.6392	Remote Similarity	NPC141071
0.6389	Remote Similarity	NPC280710
0.6389	Remote Similarity	NPC243985
0.6383	Remote Similarity	NPC476431
0.6373	Remote Similarity	NPC237795
0.6373	Remote Similarity	NPC82538
0.6364	Remote Similarity	NPC72507
0.6356	Remote Similarity	NPC7797
0.6344	Remote Similarity	NPC197805
0.6327	Remote Similarity	NPC265328
0.6327	Remote Similarity	NPC253190
0.6327	Remote Similarity	NPC122418
0.6327	Remote Similarity	NPC202642
0.6327	Remote Similarity	NPC189883
0.6327	Remote Similarity	NPC30590
0.6327	Remote Similarity	NPC27765
0.6327	Remote Similarity	NPC113733
0.6327	Remote Similarity	NPC120098
0.6327	Remote Similarity	NPC290598
0.6327	Remote Similarity	NPC46160
0.6316	Remote Similarity	NPC34834
0.6311	Remote Similarity	NPC231310
0.6311	Remote Similarity	NPC238485
0.63	Remote Similarity	NPC31330
0.6275	Remote Similarity	NPC202389
0.6275	Remote Similarity	NPC201852
0.6263	Remote Similarity	NPC157996
0.6263	Remote Similarity	NPC90979
0.6263	Remote Similarity	NPC40394
0.6263	Remote Similarity	NPC214570
0.6263	Remote Similarity	NPC34177
0.6263	Remote Similarity	NPC472805
0.6263	Remote Similarity	NPC91594
0.6263	Remote Similarity	NPC101475
0.625	Remote Similarity	NPC109528
0.6237	Remote Similarity	NPC286669
0.6237	Remote Similarity	NPC222366
0.6237	Remote Similarity	NPC476039
0.6226	Remote Similarity	NPC34754
0.6224	Remote Similarity	NPC288035
0.6224	Remote Similarity	NPC69383
0.6224	Remote Similarity	NPC22105
0.6224	Remote Similarity	NPC230301
0.6224	Remote Similarity	NPC471468
0.6224	Remote Similarity	NPC134847
0.6224	Remote Similarity	NPC66566
0.6224	Remote Similarity	NPC477923
0.6224	Remote Similarity	NPC121744
0.6224	Remote Similarity	NPC28657
0.6224	Remote Similarity	NPC304309
0.6224	Remote Similarity	NPC162742
0.6224	Remote Similarity	NPC34700
0.6224	Remote Similarity	NPC138374
0.6224	Remote Similarity	NPC313179
0.6224	Remote Similarity	NPC118508
0.6224	Remote Similarity	NPC322353
0.6224	Remote Similarity	NPC136188
0.6224	Remote Similarity	NPC171148
0.6224	Remote Similarity	NPC285893
0.6216	Remote Similarity	NPC240650
0.6214	Remote Similarity	NPC474789
0.6214	Remote Similarity	NPC52108
0.6214	Remote Similarity	NPC470384
0.6211	Remote Similarity	NPC474248
0.6211	Remote Similarity	NPC471560
0.62	Remote Similarity	NPC196753
0.62	Remote Similarity	NPC83351
0.62	Remote Similarity	NPC98386
0.62	Remote Similarity	NPC300499
0.62	Remote Similarity	NPC253807
0.62	Remote Similarity	NPC275910
0.62	Remote Similarity	NPC474989
0.62	Remote Similarity	NPC167891
0.62	Remote Similarity	NPC22955
0.62	Remote Similarity	NPC99168
0.62	Remote Similarity	NPC470396
0.62	Remote Similarity	NPC158662
0.62	Remote Similarity	NPC230295
0.6196	Remote Similarity	NPC290367
0.6196	Remote Similarity	NPC225415
0.6186	Remote Similarity	NPC130665
0.6186	Remote Similarity	NPC474140
0.6182	Remote Similarity	NPC311164
0.6182	Remote Similarity	NPC272732
0.6176	Remote Similarity	NPC476646
0.6176	Remote Similarity	NPC6707
0.6162	Remote Similarity	NPC73875
0.6162	Remote Similarity	NPC300324
0.6162	Remote Similarity	NPC106364
0.6162	Remote Similarity	NPC274079
0.6162	Remote Similarity	NPC237460
0.6162	Remote Similarity	NPC107059
0.6162	Remote Similarity	NPC321381
0.6162	Remote Similarity	NPC477925
0.6162	Remote Similarity	NPC321016
0.6162	Remote Similarity	NPC96319
0.6162	Remote Similarity	NPC240604
0.6154	Remote Similarity	NPC474493
0.6139	Remote Similarity	NPC53744
0.6139	Remote Similarity	NPC30986
0.6139	Remote Similarity	NPC209430
0.6139	Remote Similarity	NPC291379
0.6139	Remote Similarity	NPC1319
0.6129	Remote Similarity	NPC163678
0.6126	Remote Similarity	NPC476903
0.6122	Remote Similarity	NPC469533
0.6122	Remote Similarity	NPC469593
0.6122	Remote Similarity	NPC201048
0.6122	Remote Similarity	NPC476366
0.6122	Remote Similarity	NPC469534
0.6122	Remote Similarity	NPC306727
0.6117	Remote Similarity	NPC87489
0.6117	Remote Similarity	NPC20853
0.6105	Remote Similarity	NPC471238
0.61	Remote Similarity	NPC34019
0.61	Remote Similarity	NPC130136
0.61	Remote Similarity	NPC477924
0.61	Remote Similarity	NPC470758
0.61	Remote Similarity	NPC470711
0.61	Remote Similarity	NPC155986
0.61	Remote Similarity	NPC318495
0.61	Remote Similarity	NPC198968
0.6091	Remote Similarity	NPC473314
0.6087	Remote Similarity	NPC45365
0.6087	Remote Similarity	NPC293299
0.6082	Remote Similarity	NPC242992
0.6082	Remote Similarity	NPC23954
0.6078	Remote Similarity	NPC209944
0.6078	Remote Similarity	NPC241290
0.6078	Remote Similarity	NPC295131
0.6078	Remote Similarity	NPC96362
0.6078	Remote Similarity	NPC164840
0.6078	Remote Similarity	NPC236112
0.6078	Remote Similarity	NPC287749
0.6078	Remote Similarity	NPC234193
0.6071	Remote Similarity	NPC140300
0.6068	Remote Similarity	NPC169375
0.6064	Remote Similarity	NPC202017
0.6064	Remote Similarity	NPC279434
0.6058	Remote Similarity	NPC97491
0.6058	Remote Similarity	NPC57370
0.6058	Remote Similarity	NPC273356
0.6058	Remote Similarity	NPC312480
0.6042	Remote Similarity	NPC9942
0.604	Remote Similarity	NPC138621
0.604	Remote Similarity	NPC65897
0.604	Remote Similarity	NPC302041
0.604	Remote Similarity	NPC473943
0.604	Remote Similarity	NPC167037
0.604	Remote Similarity	NPC285761
0.604	Remote Similarity	NPC6978
0.604	Remote Similarity	NPC87604
0.604	Remote Similarity	NPC11908
0.604	Remote Similarity	NPC312328
0.604	Remote Similarity	NPC244385
0.604	Remote Similarity	NPC474216
0.604	Remote Similarity	NPC477522
0.604	Remote Similarity	NPC476314
0.604	Remote Similarity	NPC85346
0.604	Remote Similarity	NPC274750

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC125771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	83
0.1-0.2	560
0.2-0.3	3493
0.3-0.4	3897
0.4-0.5	960
0.5-0.6	155
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
0.6387	Remote Similarity	NPD5167	Approved
0.6293	Remote Similarity	NPD5168	Approved
0.6224	Remote Similarity	NPD6942	Approved
0.6224	Remote Similarity	NPD7339	Approved
0.6224	Remote Similarity	NPD8264	Approved
0.6162	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7645	Phase 2
0.6134	Remote Similarity	NPD5215	Approved
0.6134	Remote Similarity	NPD5217	Approved
0.6134	Remote Similarity	NPD5216	Approved
0.6082	Remote Similarity	NPD7150	Approved
0.6082	Remote Similarity	NPD7152	Approved
0.6082	Remote Similarity	NPD7151	Approved
0.5979	Remote Similarity	NPD7143	Approved
0.5979	Remote Similarity	NPD7144	Approved
0.596	Remote Similarity	NPD6926	Approved
0.596	Remote Similarity	NPD6924	Approved
0.5935	Remote Similarity	NPD6868	Approved
0.5922	Remote Similarity	NPD7525	Registered
0.5876	Remote Similarity	NPD6922	Approved
0.5876	Remote Similarity	NPD6923	Approved
0.5842	Remote Similarity	NPD6933	Approved
0.581	Remote Similarity	NPD3667	Approved
0.5794	Remote Similarity	NPD7100	Approved
0.5794	Remote Similarity	NPD7101	Approved
0.5785	Remote Similarity	NPD5169	Approved
0.5769	Remote Similarity	NPD7509	Discontinued
0.5741	Remote Similarity	NPD3618	Phase 1
0.5738	Remote Similarity	NPD5127	Approved
0.5701	Remote Similarity	NPD4786	Approved
0.5673	Remote Similarity	NPD6929	Approved
0.5669	Remote Similarity	NPD4522	Approved
0.5644	Remote Similarity	NPD4784	Approved
0.5644	Remote Similarity	NPD4785	Approved
0.5631	Remote Similarity	NPD6932	Approved
0.5625	Remote Similarity	NPD6079	Approved
0.5619	Remote Similarity	NPD4748	Discontinued
0.5619	Remote Similarity	NPD6930	Phase 2
0.5619	Remote Similarity	NPD6931	Approved
0.56	Remote Similarity	NPD4243	Approved

Structure

NPC125771 OpenBabel07101719242D 21 22 0 0 1 0 0 0 0 0999 V2000 -0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9239 0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 0.0000 -2.0000 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 2 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 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 20 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 1 0 0 0 12 15 1 0 0 0 0 12 16 1 6 0 0 0 13 15 1 0 0 0 0 13 17 1 6 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 14 20 2 0 0 0 0 16 3 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	10337976
ChEMBL	CHEMBL479676
ZINC

Physicochemical Properties

Molecular Weight:	349.08
ALogP:	2.8073
MLogP:	2.67
XLogP:	4.234
# Rotatable Bonds:	9
Polar Surface Area:	32.59
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	21

Download Data

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Structure MOL file
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