NPASS Compound

Structure

NPC475293 OpenBabel07101718222D 44 45 0 0 0 0 0 0 0 0999 V2000 3.0981 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -9.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -6.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -7.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -9.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -10.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3923 -5.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7583 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0263 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -4.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -6.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 10.8923 -4.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 13 1 0 0 0 0 2 4 2 0 0 0 0 2 14 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 7 1 0 0 0 0 5 25 1 0 0 0 0 6 8 1 0 0 0 0 6 26 1 0 0 0 0 7 41 1 0 0 0 0 8 42 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 27 2 0 0 0 0 18 22 1 0 0 0 0 18 28 2 0 0 0 0 19 39 1 0 0 0 0 20 40 1 0 0 0 0 21 25 2 0 0 0 0 21 29 1 0 0 0 0 22 26 2 0 0 0 0 22 30 1 0 0 0 0 27 31 1 0 0 0 0 28 32 1 0 0 0 0 33 43 1 0 0 0 0 34 43 2 0 0 0 0 35 43 2 0 0 0 0 36 44 1 0 0 0 0 37 44 2 0 0 0 0 38 44 2 0 0 0 0 39 43 1 0 0 0 0 40 44 1 0 0 0 0 41 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	821.86
Volume:	607.664
LogP:	0.273
LogD:	0.113
LogS:	-0.432
# Rotatable Bonds:	19
TPSA:	250.58
# H-Bond Aceptor:	16
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.034
Synthetic Accessibility Score:	3.567
Fsp3:	0.273
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.805
MDCK Permeability:	1.4392172488442156e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	101.61685180664062%
Volume Distribution (VD):	0.402
Pgp-substrate:	0.5804981589317322%

ADMET: Metabolism

CYP1A2-inhibitor:	0.148
CYP1A2-substrate:	0.019
CYP2C19-inhibitor:	0.321
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.837
CYP2C9-substrate:	0.988
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	1.661
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.804
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.373
Carcinogencity:	0.926
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.734

Download Data

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

Natural Product: NPC475293

Natural Product ID:	NPC475293
*Common Name:**	Psammaplin A Sulfate Diguanidium Salt
IUPAC Name:	[2-bromo-4-[(2E)-3-[2-[2-[[(2E)-3-(3-bromo-4-sulfooxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethylamino]-2-hydroxyimino-3-oxopropyl]phenyl] hydrogen sulfate;1,1-dimethylguanidine
Synonyms:	Psammaplin A Sulfate Diguanidium Salt
Standard InCHIKey:	DUXUTSRGERRXDR-NDFGGZAQSA-N
Standard InCHI:	InChI=1S/C22H24Br2N4O12S4.2C3H9N3/c23-15-9-13(1-3-19(15)39-43(33,34)35)11-17(27-31)21(29)25-5-7-41-42-8-6-26-22(30)18(28-32)12-14-2-4-20(16(24)10-14)40-44(36,37)38;21-6(2)3(4)5/h1-4,9-10,31-32H,5-8,11-12H2,(H,25,29)(H,26,30)(H,33,34,35)(H,36,37,38);21-2H3,(H3,4,5)/b27-17+,28-18+;;
SMILES:	CN(C(=N)N)C.CN(C(=N)N)C.O/N=C(/C(=NCCSSCCN=C(/C(=N/O)/Cc1ccc(c(c1)Br)OS(=O)(=O)O)O)O)Cc1ccc(c(c1)Br)OS(=O)(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503026
PubChem CID:	10441004
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000403] Organic sulfuric acids and derivatives [CHEMONTID:0004258] Arylsulfates [CHEMONTID:0002626] Phenylsulfates

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	Vanuatu islands	n.a.	PMID[10924170]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277766]
NPO33362	Poecillastra sp.	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17378533]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33362	Poecillastra sp.	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326327]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	=	12.27	ug.mL-1	PMID[518290]
NPT146	Cell Line	SK-OV-3	Homo sapiens	EC50	=	1.79	ug.mL-1	PMID[518290]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	EC50	=	4.48	ug.mL-1	PMID[518290]
NPT574	Cell Line	XF498	Homo sapiens	EC50	=	16.92	ug.mL-1	PMID[518290]
NPT148	Cell Line	HCT-15	Homo sapiens	EC50	=	43.17	ug.mL-1	PMID[518290]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC475293 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	264
0.1-0.2	2956
0.2-0.3	14145
0.3-0.4	10338
0.4-0.5	13070
0.5-0.6	1723
0.6-0.7	173
0.7-0.8	18
0.8-0.85	4
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC475132
0.9922	High Similarity	NPC474587
0.9466	High Similarity	NPC71888
0.9466	High Similarity	NPC120114
0.9323	High Similarity	NPC309667
0.8731	High Similarity	NPC474091
0.8676	High Similarity	NPC163810
0.8603	High Similarity	NPC166624
0.8582	High Similarity	NPC202776
0.854	High Similarity	NPC184465
0.8529	High Similarity	NPC475735
0.84	Intermediate Similarity	NPC123848
0.8146	Intermediate Similarity	NPC473738
0.8125	Intermediate Similarity	NPC474128
0.8041	Intermediate Similarity	NPC20755
0.8	Intermediate Similarity	NPC473724
0.7881	Intermediate Similarity	NPC475432
0.7817	Intermediate Similarity	NPC474753
0.7697	Intermediate Similarity	NPC258222
0.7671	Intermediate Similarity	NPC197045
0.7636	Intermediate Similarity	NPC152205
0.7636	Intermediate Similarity	NPC475283
0.75	Intermediate Similarity	NPC156311
0.7431	Intermediate Similarity	NPC99280
0.7349	Intermediate Similarity	NPC475615
0.7348	Intermediate Similarity	NPC471495
0.7244	Intermediate Similarity	NPC109968
0.7239	Intermediate Similarity	NPC473358
0.723	Intermediate Similarity	NPC303993
0.72	Intermediate Similarity	NPC213471
0.7151	Intermediate Similarity	NPC144823
0.7126	Intermediate Similarity	NPC225130
0.7122	Intermediate Similarity	NPC38458
0.7122	Intermediate Similarity	NPC311737
0.7089	Intermediate Similarity	NPC47672
0.7083	Intermediate Similarity	NPC469979
0.705	Intermediate Similarity	NPC82963
0.7041	Intermediate Similarity	NPC207819
0.7041	Intermediate Similarity	NPC298981
0.7041	Intermediate Similarity	NPC473462
0.7041	Intermediate Similarity	NPC110454
0.7041	Intermediate Similarity	NPC126128
0.7037	Intermediate Similarity	NPC54543
0.7	Intermediate Similarity	NPC290534
0.6982	Remote Similarity	NPC226001
0.6978	Remote Similarity	NPC317254
0.6968	Remote Similarity	NPC470472
0.6968	Remote Similarity	NPC78530
0.6963	Remote Similarity	NPC24101
0.6963	Remote Similarity	NPC96224
0.6959	Remote Similarity	NPC475396
0.6957	Remote Similarity	NPC233926
0.6957	Remote Similarity	NPC59387
0.6919	Remote Similarity	NPC74618
0.6919	Remote Similarity	NPC301941
0.6919	Remote Similarity	NPC214188
0.691	Remote Similarity	NPC469721
0.6859	Remote Similarity	NPC135349
0.6838	Remote Similarity	NPC153690
0.6833	Remote Similarity	NPC469731
0.6828	Remote Similarity	NPC296202
0.6815	Remote Similarity	NPC231705
0.68	Remote Similarity	NPC49172
0.6788	Remote Similarity	NPC258056
0.6786	Remote Similarity	NPC115803
0.6786	Remote Similarity	NPC118202
0.6783	Remote Similarity	NPC268572
0.6783	Remote Similarity	NPC283760
0.6783	Remote Similarity	NPC38483
0.6761	Remote Similarity	NPC473892
0.6761	Remote Similarity	NPC475658
0.6759	Remote Similarity	NPC7830
0.6753	Remote Similarity	NPC470470
0.6739	Remote Similarity	NPC471487
0.6739	Remote Similarity	NPC474149
0.6735	Remote Similarity	NPC213414
0.6732	Remote Similarity	NPC470471
0.6723	Remote Similarity	NPC141405
0.6723	Remote Similarity	NPC470951
0.6723	Remote Similarity	NPC473409
0.6723	Remote Similarity	NPC82741
0.6667	Remote Similarity	NPC471591
0.6667	Remote Similarity	NPC473372
0.6667	Remote Similarity	NPC94217
0.6646	Remote Similarity	NPC76412
0.6644	Remote Similarity	NPC136543
0.6642	Remote Similarity	NPC142297
0.662	Remote Similarity	NPC37302
0.6597	Remote Similarity	NPC122009
0.6596	Remote Similarity	NPC309808
0.6596	Remote Similarity	NPC471488
0.6593	Remote Similarity	NPC178902
0.6579	Remote Similarity	NPC275538
0.6579	Remote Similarity	NPC326966
0.6575	Remote Similarity	NPC471486
0.6556	Remote Similarity	NPC271808
0.6556	Remote Similarity	NPC325651
0.6554	Remote Similarity	NPC105999
0.6552	Remote Similarity	NPC43275
0.6541	Remote Similarity	NPC107619
0.6538	Remote Similarity	NPC224663
0.6528	Remote Similarity	NPC283468
0.6513	Remote Similarity	NPC474087
0.6513	Remote Similarity	NPC478071
0.6494	Remote Similarity	NPC267237
0.649	Remote Similarity	NPC78061
0.649	Remote Similarity	NPC159987
0.649	Remote Similarity	NPC122359
0.6479	Remote Similarity	NPC33244
0.6471	Remote Similarity	NPC11449
0.6467	Remote Similarity	NPC220311
0.6466	Remote Similarity	NPC33168
0.6463	Remote Similarity	NPC324702
0.6447	Remote Similarity	NPC150929
0.6439	Remote Similarity	NPC151715
0.6429	Remote Similarity	NPC244866
0.6391	Remote Similarity	NPC26244
0.6389	Remote Similarity	NPC303370
0.6385	Remote Similarity	NPC172128
0.637	Remote Similarity	NPC275104
0.6359	Remote Similarity	NPC80514
0.6358	Remote Similarity	NPC476249
0.6352	Remote Similarity	NPC168861
0.6351	Remote Similarity	NPC284078
0.6351	Remote Similarity	NPC83279
0.6343	Remote Similarity	NPC473388
0.6338	Remote Similarity	NPC166837
0.6329	Remote Similarity	NPC321285
0.6329	Remote Similarity	NPC214988
0.6309	Remote Similarity	NPC474862
0.6306	Remote Similarity	NPC6570
0.6306	Remote Similarity	NPC64205
0.6301	Remote Similarity	NPC323948
0.6299	Remote Similarity	NPC474614
0.6291	Remote Similarity	NPC62101
0.6291	Remote Similarity	NPC95733
0.6289	Remote Similarity	NPC476989
0.6288	Remote Similarity	NPC45040
0.6284	Remote Similarity	NPC263835
0.6284	Remote Similarity	NPC112823
0.6284	Remote Similarity	NPC41801
0.6284	Remote Similarity	NPC252817
0.6282	Remote Similarity	NPC300678
0.6282	Remote Similarity	NPC243404
0.6277	Remote Similarity	NPC91461
0.6277	Remote Similarity	NPC40258
0.6277	Remote Similarity	NPC7686
0.6267	Remote Similarity	NPC471315
0.6267	Remote Similarity	NPC471314
0.6258	Remote Similarity	NPC45191
0.6258	Remote Similarity	NPC114102
0.625	Remote Similarity	NPC83289
0.625	Remote Similarity	NPC132078
0.625	Remote Similarity	NPC189724
0.625	Remote Similarity	NPC78119
0.625	Remote Similarity	NPC51333
0.625	Remote Similarity	NPC110131
0.625	Remote Similarity	NPC29477
0.625	Remote Similarity	NPC76400
0.625	Remote Similarity	NPC212850
0.625	Remote Similarity	NPC216468
0.6243	Remote Similarity	NPC156055
0.6242	Remote Similarity	NPC86966
0.6226	Remote Similarity	NPC474673
0.6225	Remote Similarity	NPC211218
0.6222	Remote Similarity	NPC292730
0.6222	Remote Similarity	NPC82664
0.6222	Remote Similarity	NPC216520
0.6222	Remote Similarity	NPC132271
0.622	Remote Similarity	NPC296085
0.6218	Remote Similarity	NPC471953
0.6216	Remote Similarity	NPC319950
0.6216	Remote Similarity	NPC256369
0.6216	Remote Similarity	NPC65714
0.6209	Remote Similarity	NPC96275
0.6207	Remote Similarity	NPC142599
0.6204	Remote Similarity	NPC213730
0.62	Remote Similarity	NPC27581
0.6194	Remote Similarity	NPC128062
0.6194	Remote Similarity	NPC474536
0.619	Remote Similarity	NPC254088
0.6188	Remote Similarity	NPC197766
0.6188	Remote Similarity	NPC471236
0.6184	Remote Similarity	NPC272463
0.6174	Remote Similarity	NPC180207
0.6169	Remote Similarity	NPC186898
0.6169	Remote Similarity	NPC477839
0.6169	Remote Similarity	NPC13004
0.6169	Remote Similarity	NPC251571
0.6154	Remote Similarity	NPC323336
0.6154	Remote Similarity	NPC326349
0.6148	Remote Similarity	NPC274678
0.6143	Remote Similarity	NPC211551
0.6139	Remote Similarity	NPC163560
0.6139	Remote Similarity	NPC244890
0.6139	Remote Similarity	NPC471328
0.6136	Remote Similarity	NPC177420
0.6136	Remote Similarity	NPC280347
0.6131	Remote Similarity	NPC130193
0.6131	Remote Similarity	NPC92730

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	699
0.2-0.3	1226
0.3-0.4	3027
0.4-0.5	3342
0.5-0.6	691
0.6-0.7	23
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
0.6923	Remote Similarity	NPD3421	Phase 3
0.6863	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7451	Discontinued
0.6667	Remote Similarity	NPD475	Phase 2
0.6667	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1169	Approved
0.6463	Remote Similarity	NPD3143	Discontinued
0.6458	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7303	Discontinued
0.6439	Remote Similarity	NPD2933	Approved
0.6439	Remote Similarity	NPD2934	Approved
0.6405	Remote Similarity	NPD9718	Approved
0.6391	Remote Similarity	NPD2859	Approved
0.6391	Remote Similarity	NPD2860	Approved
0.6323	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2372	Approved
0.6294	Remote Similarity	NPD821	Approved
0.6289	Remote Similarity	NPD7450	Phase 2
0.625	Remote Similarity	NPD2228	Approved
0.625	Remote Similarity	NPD2234	Approved
0.625	Remote Similarity	NPD3020	Approved
0.625	Remote Similarity	NPD7438	Suspended
0.625	Remote Similarity	NPD2229	Approved
0.6242	Remote Similarity	NPD2184	Approved
0.6242	Remote Similarity	NPD2183	Approved
0.6226	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD3028	Approved
0.6194	Remote Similarity	NPD3136	Phase 2
0.6182	Remote Similarity	NPD4739	Approved
0.6176	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD5303	Approved
0.6149	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD5304	Approved
0.6118	Remote Similarity	NPD1669	Approved
0.6101	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD4480	Approved
0.6081	Remote Similarity	NPD6360	Discontinued
0.6081	Remote Similarity	NPD1758	Phase 1
0.6076	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD6346	Approved
0.6071	Remote Similarity	NPD9608	Approved
0.6071	Remote Similarity	NPD9610	Approved
0.6067	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD2561	Approved
0.6053	Remote Similarity	NPD2562	Approved
0.6049	Remote Similarity	NPD7978	Discontinued
0.6048	Remote Similarity	NPD6390	Discontinued
0.604	Remote Similarity	NPD1759	Phase 1
0.6037	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD4659	Approved
0.6013	Remote Similarity	NPD7477	Discontinued
0.6012	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4093	Discontinued
0.5988	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD5311	Approved
0.5974	Remote Similarity	NPD5310	Approved
0.5972	Remote Similarity	NPD1792	Phase 2
0.5972	Remote Similarity	NPD3021	Approved
0.5972	Remote Similarity	NPD3022	Approved
0.5963	Remote Similarity	NPD3555	Approved
0.5963	Remote Similarity	NPD3553	Approved
0.5963	Remote Similarity	NPD3552	Approved
0.5963	Remote Similarity	NPD3554	Approved
0.5962	Remote Similarity	NPD4993	Discontinued
0.596	Remote Similarity	NPD2667	Approved
0.596	Remote Similarity	NPD2668	Approved
0.5959	Remote Similarity	NPD2496	Approved
0.5959	Remote Similarity	NPD2497	Approved
0.5954	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD3070	Discontinued
0.5948	Remote Similarity	NPD6624	Discontinued
0.5935	Remote Similarity	NPD4103	Phase 2
0.5935	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD3053	Approved
0.5935	Remote Similarity	NPD3055	Approved
0.5935	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD159	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD682	Discontinued
0.5909	Remote Similarity	NPD6583	Phase 3
0.5909	Remote Similarity	NPD6582	Phase 2
0.5909	Remote Similarity	NPD3685	Discontinued
0.5875	Remote Similarity	NPD468	Phase 1
0.5874	Remote Similarity	NPD1445	Approved
0.5874	Remote Similarity	NPD1444	Approved
0.5871	Remote Similarity	NPD2922	Phase 1
0.5862	Remote Similarity	NPD7737	Approved
0.5862	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7738	Approved
0.5858	Remote Similarity	NPD4319	Phase 2
0.5857	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5111	Phase 2
0.5849	Remote Similarity	NPD5109	Approved
0.5849	Remote Similarity	NPD5110	Phase 2
0.5843	Remote Similarity	NPD3400	Discontinued
0.5839	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD8019	Approved
0.5833	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.5828	Remote Similarity	NPD4108	Discontinued
0.5828	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD9273	Approved
0.5817	Remote Similarity	NPD1983	Approved
0.5817	Remote Similarity	NPD1980	Approved
0.5817	Remote Similarity	NPD3847	Discontinued
0.5817	Remote Similarity	NPD1981	Approved
0.5813	Remote Similarity	NPD1423	Approved
0.5813	Remote Similarity	NPD2674	Phase 3
0.5813	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.58	Remote Similarity	NPD3596	Phase 2
0.5799	Remote Similarity	NPD3985	Discontinued
0.5796	Remote Similarity	NPD6584	Phase 3
0.5786	Remote Similarity	NPD1067	Discontinued
0.5783	Remote Similarity	NPD2460	Phase 3
0.5783	Remote Similarity	NPD2459	Approved
0.5783	Remote Similarity	NPD2458	Approved
0.5774	Remote Similarity	NPD7554	Discontinued
0.5771	Remote Similarity	NPD2097	Approved
0.5762	Remote Similarity	NPD317	Approved
0.5762	Remote Similarity	NPD318	Approved
0.5762	Remote Similarity	NPD16	Approved
0.5762	Remote Similarity	NPD856	Approved
0.5759	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.5759	Remote Similarity	NPD7828	Discontinued
0.5758	Remote Similarity	NPD1803	Phase 3
0.5758	Remote Similarity	NPD111	Approved
0.5752	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD3095	Discontinued
0.5752	Remote Similarity	NPD1751	Approved
0.5749	Remote Similarity	NPD6331	Phase 2
0.5749	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD7495	Discontinued
0.5745	Remote Similarity	NPD1242	Phase 1
0.5743	Remote Similarity	NPD9379	Approved
0.5743	Remote Similarity	NPD9377	Approved
0.5742	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.574	Remote Similarity	NPD6087	Phase 1
0.5734	Remote Similarity	NPD9244	Approved
0.5733	Remote Similarity	NPD709	Approved
0.5733	Remote Similarity	NPD6387	Discontinued
0.5732	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.5731	Remote Similarity	NPD7523	Phase 3
0.573	Remote Similarity	NPD2802	Phase 3
0.5724	Remote Similarity	NPD6580	Approved
0.5724	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD6581	Approved
0.5714	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6407	Approved
0.5714	Remote Similarity	NPD6405	Approved
0.5714	Remote Similarity	NPD5929	Approved
0.5714	Remote Similarity	NPD2586	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD2098	Approved
0.5706	Remote Similarity	NPD2874	Phase 2
0.5706	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD2568	Approved
0.5706	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD2157	Approved
0.5706	Remote Similarity	NPD5314	Approved
0.5704	Remote Similarity	NPD940	Approved
0.5704	Remote Similarity	NPD846	Approved
0.5698	Remote Similarity	NPD2781	Approved
0.5698	Remote Similarity	NPD2890	Approved
0.5698	Remote Similarity	NPD2888	Approved
0.5698	Remote Similarity	NPD2889	Approved
0.5698	Remote Similarity	NPD2017	Approved
0.5697	Remote Similarity	NPD1725	Approved
0.5695	Remote Similarity	NPD9568	Approved
0.5687	Remote Similarity	NPD5163	Phase 2
0.5687	Remote Similarity	NPD5156	Approved
0.5687	Remote Similarity	NPD5155	Approved
0.5687	Remote Similarity	NPD1024	Discontinued
0.5686	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD3062	Approved
0.5679	Remote Similarity	NPD1555	Discontinued
0.5679	Remote Similarity	NPD3061	Approved
0.5679	Remote Similarity	NPD3059	Approved
0.5677	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.5677	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD9538	Approved
0.5667	Remote Similarity	NPD7608	Discontinued
0.5667	Remote Similarity	NPD4652	Approved
0.5664	Remote Similarity	NPD4658	Approved
0.5664	Remote Similarity	NPD4656	Approved
0.566	Remote Similarity	NPD4212	Discontinued
0.566	Remote Similarity	NPD3635	Approved
0.566	Remote Similarity	NPD3636	Approved
0.566	Remote Similarity	NPD3637	Approved
0.566	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.566	Remote Similarity	NPD1712	Approved
0.5654	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3144	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data