NPASS Compound

Structure

NPC475196 OpenBabel07101719122D 64 68 0 0 1 0 0 0 0 0999 V2000 9.8483 -12.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4993 -4.7489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3055 -13.4001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9933 -4.1403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5777 -0.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0306 -13.2448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8611 -4.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1391 -10.5286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3611 -5.7022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2657 -11.0155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0633 -8.8861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1091 -10.3316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2287 -8.3352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2745 -9.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9458 -9.5474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5302 -4.0930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9375 -5.2281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2398 -6.2425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8380 -10.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4438 -2.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4761 -6.5562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7739 -7.4520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0122 -5.6074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1232 -12.8245 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.9335 -5.1385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0035 -9.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6889 -7.0771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3343 -8.7825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7324 -9.9879 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.9234 -7.4506 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.3098 -2.9998 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.3392 -5.4943 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.5326 -10.3354 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.0336 -11.8285 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.0353 -11.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0824 -6.1634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8635 -11.0785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0991 -11.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4234 -9.0368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0872 -8.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3098 -3.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9116 -5.3464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4084 -8.0369 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3080 -10.8056 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.8745 -7.1416 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.0050 -11.5914 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 13.1758 -2.4998 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.9530 -9.4280 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.4438 -4.4998 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4998 -8.2316 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 6.8274 -12.7468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0334 -5.8544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4986 -11.8509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6121 -12.2907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0871 -8.4221 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1758 -4.4998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2630 -4.4102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1758 -1.4998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1758 -0.4998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.1758 -1.4998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4438 -1.4998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7850 -5.8334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6412 -8.4319 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 13.1758 -1.4998 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 61 1 0 0 0 0 6 24 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 32 1 0 0 0 0 10 33 1 0 0 0 0 11 13 1 0 0 0 0 11 26 2 0 0 0 0 12 14 2 0 0 0 0 12 26 1 0 0 0 0 13 28 2 0 0 0 0 14 28 1 0 0 0 0 15 48 1 0 0 0 0 16 49 1 0 0 0 0 17 23 1 0 0 0 0 17 25 2 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 26 1 0 0 0 0 19 29 1 0 0 0 0 20 31 1 0 0 0 0 20 61 1 0 0 0 0 21 30 1 0 0 0 0 21 62 1 0 0 0 0 22 27 2 0 0 0 0 22 63 1 0 0 0 0 24 34 1 0 0 0 0 25 42 1 0 0 0 0 27 43 1 0 0 0 0 28 50 1 0 0 0 0 29 39 1 0 0 0 0 29 44 1 0 0 0 0 30 40 1 0 0 0 0 30 45 1 0 0 0 0 31 41 1 0 0 0 0 31 47 1 0 0 0 0 32 36 1 0 0 0 0 32 49 1 0 0 0 0 33 37 1 0 0 0 0 33 48 1 0 0 0 0 34 35 1 0 0 0 0 34 46 1 0 0 0 0 35 38 1 0 0 0 0 35 51 2 0 0 0 0 36 45 2 0 0 0 0 36 52 1 0 0 0 0 37 46 2 0 0 0 0 37 53 1 0 0 0 0 38 44 1 0 0 0 0 38 54 2 0 0 0 0 39 43 2 0 0 0 0 39 63 1 0 0 0 0 40 48 1 0 0 0 0 40 55 2 0 0 0 0 41 49 1 0 0 0 0 41 56 2 0 0 0 0 42 57 2 0 0 0 0 42 62 1 0 0 0 0 47 64 1 0 0 0 0 58 64 1 0 0 0 0 59 64 2 0 0 0 0 60 64 2 0 0 0 0 M CHG 1 50 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	928.32
Volume:	882.245
LogP:	0.803
LogD:	1.268
LogS:	-2.698
# Rotatable Bonds:	13
TPSA:	282.87
# H-Bond Aceptor:	20
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.118
Synthetic Accessibility Score:	6.701
Fsp3:	0.524
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.563
MDCK Permeability:	9.546498404233716e-06
Pgp-inhibitor:	0.933
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.937
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	90.23863983154297%
Volume Distribution (VD):	0.296
Pgp-substrate:	16.495290756225586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.196
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.645
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.546
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	2.123
Half-life (T1/2):	0.289

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.209
Carcinogencity:	0.14
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.16

Download Data

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

Natural Product: NPC475196

Natural Product ID:	NPC475196
*Common Name:**	Scleritodermin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MJCWFUMOVWRXTI-OEYAGHNCSA-M
Standard InCHI:	InChI=1S/C42H55N7O13S2.Na/c1-6-24(3)34-35(51)38(54)44-29(19-26-11-13-28(50)14-12-26)39-43-27(22-63-39)18-23(2)17-25(4)42(57)62-21-30(40(55)48-15-8-10-33(48)37(53)46-34)45-36(52)32-9-7-16-49(32)41(56)31(20-61-5)47-64(58,59)60;/h11-14,17-18,22,24,29-34,47,50H,6-10,15-16,19-21H2,1-5H3,(H,44,54)(H,45,52)(H,46,53)(H,58,59,60);/q;+1/p-1/b23-18+,25-17-;/t24-,29+,30+,31-,32+,33+,34+;/m1./s1
SMILES:	CCC(C)C1C(=O)C(=O)NC(C2=NC(=CS2)C=C(C=C(C(=O)OCC(C(=O)N3CCCC3C(=O)N1)NC(=O)C4CCCN4C(=O)C(COC)NS(=O)(=O)[O-])C)C)CC5=CC=C(C=C5)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500748
PubChem CID:	23675067
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO8885	Scleritoderma nodosum	Species	Scleritodermidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043437]
NPO8885	Scleritoderma nodosum	Species	Scleritodermidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
IC50	4
Others	3

Activity Type	# Activity
Cell Line	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	1900.0	nM	PMID[495451]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	5600.0	nM	PMID[495451]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	940.0	nM	PMID[495451]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	670.0	nM	PMID[495451]
NPT393	Cell Line	HCT-116	Homo sapiens	Ratio IC50	=	2.9	n.a.	PMID[495451]
NPT179	Cell Line	A2780	Homo sapiens	FC	=	5.5	n.a.	PMID[495451]
NPT2	Others	Unspecified		Inhibition	=	50.0	%	PMID[495451]

☑ 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 NPC475196 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	308
0.1-0.2	2530
0.2-0.3	11977
0.3-0.4	14068
0.4-0.5	10788
0.5-0.6	2611
0.6-0.7	396
0.7-0.8	15
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8224	Intermediate Similarity	NPC14877
0.8224	Intermediate Similarity	NPC475350
0.8224	Intermediate Similarity	NPC145178
0.8111	Intermediate Similarity	NPC251036
0.7661	Intermediate Similarity	NPC75498
0.7606	Intermediate Similarity	NPC165538
0.7594	Intermediate Similarity	NPC329961
0.7594	Intermediate Similarity	NPC122427
0.7545	Intermediate Similarity	NPC257511
0.7406	Intermediate Similarity	NPC96016
0.7136	Intermediate Similarity	NPC239660
0.7136	Intermediate Similarity	NPC106235
0.6971	Remote Similarity	NPC469858
0.6941	Remote Similarity	NPC329731
0.6941	Remote Similarity	NPC4910
0.6914	Remote Similarity	NPC315061
0.6906	Remote Similarity	NPC184933
0.6906	Remote Similarity	NPC59827
0.6903	Remote Similarity	NPC315411
0.6891	Remote Similarity	NPC478141
0.687	Remote Similarity	NPC314254
0.687	Remote Similarity	NPC313966
0.6814	Remote Similarity	NPC477527
0.6806	Remote Similarity	NPC161242
0.6772	Remote Similarity	NPC153400
0.6759	Remote Similarity	NPC478030
0.6743	Remote Similarity	NPC25316
0.6743	Remote Similarity	NPC263485
0.6743	Remote Similarity	NPC229160
0.6732	Remote Similarity	NPC313587
0.6732	Remote Similarity	NPC315893
0.6732	Remote Similarity	NPC316110
0.6728	Remote Similarity	NPC475534
0.6728	Remote Similarity	NPC476080
0.6697	Remote Similarity	NPC475330
0.6682	Remote Similarity	NPC24990
0.6682	Remote Similarity	NPC161143
0.6667	Remote Similarity	NPC174652
0.6667	Remote Similarity	NPC319232
0.6667	Remote Similarity	NPC24370
0.6651	Remote Similarity	NPC476103
0.664	Remote Similarity	NPC284888
0.6628	Remote Similarity	NPC75609
0.6628	Remote Similarity	NPC140284
0.6626	Remote Similarity	NPC14288
0.6622	Remote Similarity	NPC477526
0.6622	Remote Similarity	NPC299806
0.662	Remote Similarity	NPC472923
0.6611	Remote Similarity	NPC79386
0.6608	Remote Similarity	NPC477638
0.6608	Remote Similarity	NPC477632
0.6604	Remote Similarity	NPC241794
0.6579	Remote Similarity	NPC329295
0.6573	Remote Similarity	NPC323752
0.6571	Remote Similarity	NPC304307
0.6571	Remote Similarity	NPC124920
0.6571	Remote Similarity	NPC34580
0.6571	Remote Similarity	NPC118559
0.6545	Remote Similarity	NPC100547
0.654	Remote Similarity	NPC323336
0.654	Remote Similarity	NPC326349
0.6538	Remote Similarity	NPC246303
0.6532	Remote Similarity	NPC470112
0.6532	Remote Similarity	NPC477516
0.6532	Remote Similarity	NPC167763
0.6532	Remote Similarity	NPC470903
0.6528	Remote Similarity	NPC470900
0.6528	Remote Similarity	NPC129486
0.6528	Remote Similarity	NPC315388
0.6518	Remote Similarity	NPC223409
0.6518	Remote Similarity	NPC95240
0.6518	Remote Similarity	NPC322135
0.6516	Remote Similarity	NPC153554
0.6514	Remote Similarity	NPC475532
0.6507	Remote Similarity	NPC5194
0.6507	Remote Similarity	NPC261934
0.6506	Remote Similarity	NPC323198
0.6504	Remote Similarity	NPC261251
0.6504	Remote Similarity	NPC477636
0.6502	Remote Similarity	NPC471050
0.6502	Remote Similarity	NPC471048
0.6502	Remote Similarity	NPC471049
0.6498	Remote Similarity	NPC475123
0.6498	Remote Similarity	NPC475204
0.6484	Remote Similarity	NPC136797
0.6484	Remote Similarity	NPC165285
0.6483	Remote Similarity	NPC478005
0.6478	Remote Similarity	NPC194740
0.6471	Remote Similarity	NPC194671
0.6471	Remote Similarity	NPC269750
0.6466	Remote Similarity	NPC328924
0.6466	Remote Similarity	NPC54803
0.6466	Remote Similarity	NPC321592
0.6463	Remote Similarity	NPC214142
0.6447	Remote Similarity	NPC477631
0.6445	Remote Similarity	NPC469903
0.6437	Remote Similarity	NPC323244
0.6436	Remote Similarity	NPC197881
0.6435	Remote Similarity	NPC477639
0.6429	Remote Similarity	NPC56685
0.6429	Remote Similarity	NPC262166
0.6429	Remote Similarity	NPC28945
0.642	Remote Similarity	NPC475609
0.6419	Remote Similarity	NPC328763
0.6414	Remote Similarity	NPC33064
0.6414	Remote Similarity	NPC245055
0.6414	Remote Similarity	NPC325976
0.6413	Remote Similarity	NPC477637
0.6409	Remote Similarity	NPC279871
0.6409	Remote Similarity	NPC17698
0.6409	Remote Similarity	NPC158277
0.6409	Remote Similarity	NPC181081
0.6409	Remote Similarity	NPC471165
0.6406	Remote Similarity	NPC302597
0.6402	Remote Similarity	NPC469901
0.6396	Remote Similarity	NPC475421
0.6391	Remote Similarity	NPC314056
0.6389	Remote Similarity	NPC63931
0.6379	Remote Similarity	NPC49195
0.6379	Remote Similarity	NPC303658
0.6376	Remote Similarity	NPC115282
0.6375	Remote Similarity	NPC220852
0.6371	Remote Similarity	NPC477630
0.6371	Remote Similarity	NPC477635
0.6364	Remote Similarity	NPC184680
0.6364	Remote Similarity	NPC137627
0.636	Remote Similarity	NPC60516
0.636	Remote Similarity	NPC163961
0.636	Remote Similarity	NPC473305
0.6359	Remote Similarity	NPC61004
0.6359	Remote Similarity	NPC254700
0.6352	Remote Similarity	NPC315804
0.6352	Remote Similarity	NPC313804
0.6351	Remote Similarity	NPC202198
0.6348	Remote Similarity	NPC302715
0.6347	Remote Similarity	NPC471568
0.6347	Remote Similarity	NPC478011
0.6347	Remote Similarity	NPC46009
0.6347	Remote Similarity	NPC473693
0.6339	Remote Similarity	NPC82472
0.6339	Remote Similarity	NPC470785
0.6335	Remote Similarity	NPC317362
0.6335	Remote Similarity	NPC317725
0.6335	Remote Similarity	NPC26108
0.6335	Remote Similarity	NPC318930
0.6335	Remote Similarity	NPC326407
0.6333	Remote Similarity	NPC473491
0.633	Remote Similarity	NPC141957
0.6329	Remote Similarity	NPC316008
0.6329	Remote Similarity	NPC313867
0.6327	Remote Similarity	NPC478007
0.6326	Remote Similarity	NPC469902
0.6324	Remote Similarity	NPC314176
0.6324	Remote Similarity	NPC272549
0.632	Remote Similarity	NPC478013
0.632	Remote Similarity	NPC326363
0.6318	Remote Similarity	NPC89831
0.6316	Remote Similarity	NPC102959
0.6314	Remote Similarity	NPC477588
0.6314	Remote Similarity	NPC477586
0.6314	Remote Similarity	NPC477585
0.6314	Remote Similarity	NPC477590
0.6309	Remote Similarity	NPC323662
0.6301	Remote Similarity	NPC473000
0.6299	Remote Similarity	NPC285343
0.6298	Remote Similarity	NPC314358
0.6298	Remote Similarity	NPC314882
0.6295	Remote Similarity	NPC472999
0.6291	Remote Similarity	NPC244509
0.629	Remote Similarity	NPC306804
0.629	Remote Similarity	NPC248670
0.6288	Remote Similarity	NPC240130
0.6288	Remote Similarity	NPC61332
0.6288	Remote Similarity	NPC470901
0.6288	Remote Similarity	NPC216507
0.6287	Remote Similarity	NPC321939
0.628	Remote Similarity	NPC315283
0.628	Remote Similarity	NPC314388
0.6279	Remote Similarity	NPC244336
0.6279	Remote Similarity	NPC469898
0.6275	Remote Similarity	NPC478029
0.6275	Remote Similarity	NPC478008
0.6275	Remote Similarity	NPC470784
0.6273	Remote Similarity	NPC40234
0.6272	Remote Similarity	NPC94862
0.6261	Remote Similarity	NPC476227
0.625	Remote Similarity	NPC469243
0.6244	Remote Similarity	NPC328494
0.6239	Remote Similarity	NPC477550
0.6239	Remote Similarity	NPC477552
0.6235	Remote Similarity	NPC477589
0.6235	Remote Similarity	NPC477587
0.6233	Remote Similarity	NPC469900
0.6233	Remote Similarity	NPC50016
0.6227	Remote Similarity	NPC478012
0.6227	Remote Similarity	NPC186617
0.6222	Remote Similarity	NPC249662
0.6216	Remote Similarity	NPC273755
0.6215	Remote Similarity	NPC473580
0.6211	Remote Similarity	NPC294951

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 NPC475196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	538
0.2-0.3	970
0.3-0.4	1967
0.4-0.5	3827
0.5-0.6	1550
0.6-0.7	125
0.7-0.8	1
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
0.7256	Intermediate Similarity	NPD6632	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8339	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8284	Discontinued
0.6894	Remote Similarity	NPD6627	Discontinued
0.6852	Remote Similarity	NPD2957	Phase 2
0.6762	Remote Similarity	NPD7806	Phase 2
0.6758	Remote Similarity	NPD8255	Phase 2
0.6729	Remote Similarity	NPD4652	Approved
0.6723	Remote Similarity	NPD6187	Approved
0.6695	Remote Similarity	NPD6189	Approved
0.6695	Remote Similarity	NPD6188	Approved
0.6682	Remote Similarity	NPD2097	Approved
0.6638	Remote Similarity	NPD2853	Approved
0.662	Remote Similarity	NPD2098	Approved
0.6614	Remote Similarity	NPD3328	Phase 2
0.6603	Remote Similarity	NPD4884	Discovery
0.6598	Remote Similarity	NPD7711	Discontinued
0.6571	Remote Similarity	NPD8292	Phase 2
0.6556	Remote Similarity	NPD8107	Approved
0.6549	Remote Similarity	NPD6205	Discontinued
0.6543	Remote Similarity	NPD8108	Approved
0.6528	Remote Similarity	NPD2889	Approved
0.6528	Remote Similarity	NPD2890	Approved
0.6528	Remote Similarity	NPD2888	Approved
0.6528	Remote Similarity	NPD2017	Approved
0.6516	Remote Similarity	NPD6173	Approved
0.6513	Remote Similarity	NPD7605	Discovery
0.6511	Remote Similarity	NPD3350	Approved
0.6496	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD3351	Approved
0.6477	Remote Similarity	NPD8253	Phase 3
0.6476	Remote Similarity	NPD5077	Approved
0.6476	Remote Similarity	NPD5076	Approved
0.6473	Remote Similarity	NPD1976	Approved
0.6471	Remote Similarity	NPD3878	Approved
0.6462	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3879	Approved
0.6434	Remote Similarity	NPD6475	Phase 2
0.6389	Remote Similarity	NPD7853	Phase 2
0.6388	Remote Similarity	NPD5852	Approved
0.6388	Remote Similarity	NPD5851	Approved
0.6384	Remote Similarity	NPD7977	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5817	Discontinued
0.6371	Remote Similarity	NPD8071	Approved
0.6364	Remote Similarity	NPD5191	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD8260	Approved
0.6344	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6253	Approved
0.6323	Remote Similarity	NPD5484	Approved
0.6323	Remote Similarity	NPD5485	Approved
0.6316	Remote Similarity	NPD5461	Discontinued
0.6314	Remote Similarity	NPD2893	Phase 3
0.6298	Remote Similarity	NPD6256	Approved
0.6298	Remote Similarity	NPD6255	Approved
0.6298	Remote Similarity	NPD6254	Approved
0.6287	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD8303	Discontinued
0.6275	Remote Similarity	NPD8356	Approved
0.627	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD2891	Approved
0.6261	Remote Similarity	NPD6659	Phase 2
0.6261	Remote Similarity	NPD6505	Approved
0.6261	Remote Similarity	NPD6504	Approved
0.6256	Remote Similarity	NPD6092	Discontinued
0.6255	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3307	Approved
0.6218	Remote Similarity	NPD8272	Phase 2
0.6215	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7470	Discontinued
0.6198	Remote Similarity	NPD5857	Phase 3
0.6198	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD8489	Phase 1
0.6194	Remote Similarity	NPD7180	Phase 3
0.6194	Remote Similarity	NPD3308	Approved
0.6192	Remote Similarity	NPD4904	Approved
0.619	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD4557	Approved
0.6175	Remote Similarity	NPD8430	Approved
0.6173	Remote Similarity	NPD5452	Phase 2
0.6172	Remote Similarity	NPD5265	Approved
0.6172	Remote Similarity	NPD5264	Approved
0.6169	Remote Similarity	NPD3270	Approved
0.6164	Remote Similarity	NPD3479	Discontinued
0.6163	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7681	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6303	Approved
0.6154	Remote Similarity	NPD6304	Approved
0.6154	Remote Similarity	NPD7967	Discontinued
0.6151	Remote Similarity	NPD4906	Approved
0.6151	Remote Similarity	NPD4438	Approved
0.6151	Remote Similarity	NPD4903	Approved
0.6151	Remote Similarity	NPD4905	Approved
0.615	Remote Similarity	NPD6390	Discontinued
0.615	Remote Similarity	NPD5638	Approved
0.615	Remote Similarity	NPD7303	Discontinued
0.6147	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD1986	Approved
0.6145	Remote Similarity	NPD3271	Approved
0.6145	Remote Similarity	NPD3275	Approved
0.6137	Remote Similarity	NPD3958	Approved
0.6132	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.613	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.613	Remote Similarity	NPD6891	Phase 2
0.613	Remote Similarity	NPD8359	Phase 2
0.6122	Remote Similarity	NPD4679	Discontinued
0.6121	Remote Similarity	NPD5994	Discontinued
0.6118	Remote Similarity	NPD7896	Approved
0.6111	Remote Similarity	NPD7994	Phase 2
0.6109	Remote Similarity	NPD6324	Phase 1
0.6109	Remote Similarity	NPD6888	Discontinued
0.6109	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD6349	Phase 1
0.6098	Remote Similarity	NPD7496	Phase 2
0.6098	Remote Similarity	NPD5323	Approved
0.6094	Remote Similarity	NPD3074	Discontinued
0.6093	Remote Similarity	NPD4646	Approved
0.6093	Remote Similarity	NPD4648	Approved
0.6093	Remote Similarity	NPD4647	Approved
0.6091	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD3659	Discontinued
0.6084	Remote Similarity	NPD4887	Discontinued
0.6081	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD7484	Phase 3
0.6081	Remote Similarity	NPD7485	Phase 3
0.6078	Remote Similarity	NPD5113	Approved
0.6078	Remote Similarity	NPD7031	Phase 1
0.6078	Remote Similarity	NPD5112	Approved
0.6078	Remote Similarity	NPD7664	Discontinued
0.6078	Remote Similarity	NPD5114	Approved
0.6077	Remote Similarity	NPD8117	Approved
0.6077	Remote Similarity	NPD8116	Phase 3
0.6071	Remote Similarity	NPD7928	Approved
0.6071	Remote Similarity	NPD7929	Approved
0.6067	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7316	Discontinued
0.6062	Remote Similarity	NPD8016	Phase 3
0.6062	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4434	Approved
0.6061	Remote Similarity	NPD1987	Approved
0.6061	Remote Similarity	NPD1985	Approved
0.6057	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD7970	Approved
0.6057	Remote Similarity	NPD4897	Phase 2
0.6057	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4368	Phase 2
0.604	Remote Similarity	NPD6796	Discontinued
0.6036	Remote Similarity	NPD7553	Discontinued
0.6036	Remote Similarity	NPD8459	Approved
0.6036	Remote Similarity	NPD8460	Approved
0.6035	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4435	Approved
0.6031	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD4741	Phase 3
0.6025	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD4742	Phase 3
0.6024	Remote Similarity	NPD6369	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6347	Phase 2
0.6009	Remote Similarity	NPD2516	Approved
0.6008	Remote Similarity	NPD3263	Phase 3
0.6007	Remote Similarity	NPD7544	Discontinued
0.6007	Remote Similarity	NPD6023	Discontinued
0.6	Remote Similarity	NPD5229	Approved
0.6	Remote Similarity	NPD2088	Approved
0.6	Remote Similarity	NPD2087	Approved
0.6	Remote Similarity	NPD5230	Approved
0.6	Remote Similarity	NPD5299	Approved
0.6	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.5993	Remote Similarity	NPD8463	Approved
0.5993	Remote Similarity	NPD7655	Discontinued
0.5992	Remote Similarity	NPD4130	Phase 3
0.5991	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD4086	Phase 1
0.5982	Remote Similarity	NPD2517	Approved
0.5981	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD2016	Approved
0.5981	Remote Similarity	NPD2013	Approved
0.5981	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD2014	Approved
0.5977	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7688	Phase 1
0.5976	Remote Similarity	NPD4439	Discontinued
0.5976	Remote Similarity	NPD5866	Approved
0.5975	Remote Similarity	NPD3802	Phase 3
0.5972	Remote Similarity	NPD6681	Discovery
0.5964	Remote Similarity	NPD7133	Discontinued
0.596	Remote Similarity	NPD6974	Phase 3
0.5957	Remote Similarity	NPD1745	Approved
0.5955	Remote Similarity	NPD4567	Approved
0.5955	Remote Similarity	NPD4566	Approved
0.5953	Remote Similarity	NPD7796	Approved
0.5953	Remote Similarity	NPD4928	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