NPASS Compound

Structure

NPC473231 OpenBabel07101718222D 44 49 0 0 1 0 0 0 0 0999 V2000 3.8708 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0749 4.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9279 3.5372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8790 3.8462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2728 1.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7728 2.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6199 0.2228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9582 1.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 1.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6492 2.6601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 2.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2891 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 0.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1388 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3546 1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3849 -0.2384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8708 0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3839 4.0270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2728 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1388 0.0865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0238 2.3328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0019 2.1249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2728 0.5865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6710 2.8681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2728 1.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3109 1.1738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 0.0865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6418 0.4307 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3360 0.0706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7369 0.5865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3620 3.8191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7340 -3.1348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4339 -0.5474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0048 0.5865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7147 3.2839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0703 -2.4962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 11 29 1 0 0 0 0 12 30 1 0 0 0 0 13 31 1 0 0 0 0 14 32 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 21 2 0 0 0 0 16 23 1 0 0 0 0 17 33 1 0 0 0 0 17 35 2 0 0 0 0 18 36 2 0 0 0 0 18 40 1 0 0 0 0 19 37 2 0 0 0 0 19 41 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 21 33 1 0 0 0 0 22 25 1 0 0 0 0 22 40 1 6 0 0 0 23 24 1 0 0 0 0 23 41 1 6 0 0 0 24 29 1 0 0 0 0 24 31 1 6 0 0 0 25 30 1 0 0 0 0 25 32 1 6 0 0 0 26 38 1 0 0 0 0 26 42 1 0 0 0 0 27 43 1 0 0 0 0 27 44 1 0 0 0 0 28 34 1 1 0 0 0 28 42 1 0 0 0 0 28 43 1 0 0 0 0 31 33 1 1 0 0 0 32 34 1 1 0 0 0 33 39 1 1 0 0 0 34 20 1 1 0 0 0 34 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.32
Volume:	620.001
LogP:	4.772
LogD:	3.427
LogS:	-4.797
# Rotatable Bonds:	6
TPSA:	137.82
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.27
Synthetic Accessibility Score:	6.363
Fsp3:	0.794
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.287
MDCK Permeability:	3.989713150076568e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	63.196449279785156%
Volume Distribution (VD):	2.076
Pgp-substrate:	30.990270614624023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.869
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.379
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.821

ADMET: Excretion

Clearance (CL):	2.256
Half-life (T1/2):	0.009

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.982
Rat Oral Acute Toxicity:	1.0
Maximum Recommended Daily Dose:	0.526
Skin Sensitization:	0.762
Carcinogencity:	0.985
Eye Corrosion:	0.012
Eye Irritation:	0.022
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC473231

Natural Product ID:	NPC473231
*Common Name:**	Capsicodendrin
IUPAC Name:	n.a.
Synonyms:	Capsicodendrin
Standard InCHIKey:	ASRYDWWUAZEWIH-QXSHUVCSSA-N
Standard InCHI:	InChI=1S/C34H48O10/c1-18(36)40-22-15-20-26(38)42-28-34(20,32(8)14-10-12-30(5,6)25(22)32)44-27(43-28)21-16-23(41-19(2)37)24-29(3,4)11-9-13-31(24,7)33(21,39)17-35/h15-17,22-28,38-39H,9-14H2,1-8H3/t22-,23-,24+,25+,26?,27?,28+,31+,32+,33-,34+/m1/s1
SMILES:	CC(=O)OC1C=C2C(OC3C2(C4(C1C(CCC4)(C)C)C)OC(O3)C5=CC(C6C(CCCC6(C5(C=O)O)C)(C)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376261
PubChem CID:	44419494
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic acids and derivatives

*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
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17286431]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18179176]
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	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	3
MIC	9
Others	2

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Organism	7
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT497	Individual Protein	Maltase-glucoamylase	Homo sapiens	Inhibition	=	89.4	%	PMID[496695]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	940.0	nM	PMID[496695]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	860.0	nM	PMID[496695]
NPT4951	Cell Line	E6SM	Homo sapiens	MIC	>=	1030.0	nM	PMID[496695]
NPT165	Cell Line	HeLa	Homo sapiens	MIC	=	5160.0	nM	PMID[496695]
NPT2	Others	Unspecified		IC50	=	1210.0	nM	PMID[496695]
NPT334	Organism	Vaccinia virus	Vaccinia virus	MIC	>	1030.0	nM	PMID[496695]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC	>	1030.0	nM	PMID[496695]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	MIC	>	1030.0	nM	PMID[496695]
NPT1766	Organism	Human herpesvirus 1 strain KOS	Human herpesvirus 1 strain KOS	MIC	>	1030.0	nM	PMID[496695]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	MIC	>	1030.0	nM	PMID[496695]
NPT335	Organism	Human coxsackievirus B4	Human coxsackievirus B4	MIC	>	1030.0	nM	PMID[496695]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC	>	1030.0	nM	PMID[496695]
NPT2	Others	Unspecified		Inhibition	=	83.7	%	PMID[496696]

☑ 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 NPC473231 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	243
0.1-0.2	1389
0.2-0.3	4415
0.3-0.4	9181
0.4-0.5	11856
0.5-0.6	7390
0.6-0.7	5917
0.7-0.8	2225
0.8-0.85	76
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9911	High Similarity	NPC473250
0.8571	High Similarity	NPC122971
0.8571	High Similarity	NPC477071
0.8537	High Similarity	NPC470780
0.8487	Intermediate Similarity	NPC45475
0.8475	Intermediate Similarity	NPC474046
0.8475	Intermediate Similarity	NPC470628
0.8475	Intermediate Similarity	NPC259306
0.8462	Intermediate Similarity	NPC293658
0.8462	Intermediate Similarity	NPC474410
0.8407	Intermediate Similarity	NPC258532
0.8403	Intermediate Similarity	NPC473590
0.8403	Intermediate Similarity	NPC23046
0.839	Intermediate Similarity	NPC181145
0.839	Intermediate Similarity	NPC469877
0.839	Intermediate Similarity	NPC470919
0.8376	Intermediate Similarity	NPC302146
0.8362	Intermediate Similarity	NPC83005
0.8333	Intermediate Similarity	NPC127609
0.8319	Intermediate Similarity	NPC474734
0.8305	Intermediate Similarity	NPC157441
0.8305	Intermediate Similarity	NPC75167
0.8305	Intermediate Similarity	NPC311592
0.8293	Intermediate Similarity	NPC41129
0.8268	Intermediate Similarity	NPC471855
0.8264	Intermediate Similarity	NPC475834
0.8264	Intermediate Similarity	NPC475775
0.8264	Intermediate Similarity	NPC474179
0.8264	Intermediate Similarity	NPC476529
0.825	Intermediate Similarity	NPC473968
0.824	Intermediate Similarity	NPC42399
0.8235	Intermediate Similarity	NPC472274
0.8226	Intermediate Similarity	NPC470922
0.822	Intermediate Similarity	NPC174836
0.822	Intermediate Similarity	NPC12046
0.822	Intermediate Similarity	NPC194951
0.8205	Intermediate Similarity	NPC5103
0.8203	Intermediate Similarity	NPC478151
0.8203	Intermediate Similarity	NPC88668
0.8197	Intermediate Similarity	NPC48692
0.8197	Intermediate Similarity	NPC109607
0.8197	Intermediate Similarity	NPC294112
0.8197	Intermediate Similarity	NPC107338
0.8189	Intermediate Similarity	NPC476074
0.8189	Intermediate Similarity	NPC213634
0.8189	Intermediate Similarity	NPC134914
0.8189	Intermediate Similarity	NPC329993
0.8189	Intermediate Similarity	NPC475377
0.8189	Intermediate Similarity	NPC264566
0.8189	Intermediate Similarity	NPC301639
0.8189	Intermediate Similarity	NPC45346
0.8189	Intermediate Similarity	NPC478064
0.8189	Intermediate Similarity	NPC478065
0.8189	Intermediate Similarity	NPC262796
0.8189	Intermediate Similarity	NPC172374
0.8189	Intermediate Similarity	NPC173435
0.8189	Intermediate Similarity	NPC475167
0.8182	Intermediate Similarity	NPC475913
0.8175	Intermediate Similarity	NPC470475
0.8175	Intermediate Similarity	NPC470476
0.816	Intermediate Similarity	NPC250556
0.816	Intermediate Similarity	NPC469750
0.8154	Intermediate Similarity	NPC251998
0.8151	Intermediate Similarity	NPC469463
0.8151	Intermediate Similarity	NPC56448
0.8151	Intermediate Similarity	NPC469496
0.8151	Intermediate Similarity	NPC469454
0.8145	Intermediate Similarity	NPC67251
0.8136	Intermediate Similarity	NPC475668
0.8136	Intermediate Similarity	NPC475480
0.8136	Intermediate Similarity	NPC473921
0.813	Intermediate Similarity	NPC31193
0.813	Intermediate Similarity	NPC75417
0.813	Intermediate Similarity	NPC202051
0.813	Intermediate Similarity	NPC242840
0.8125	Intermediate Similarity	NPC477195
0.8125	Intermediate Similarity	NPC478152
0.8125	Intermediate Similarity	NPC478150
0.8125	Intermediate Similarity	NPC478153
0.8125	Intermediate Similarity	NPC478154
0.812	Intermediate Similarity	NPC143706
0.812	Intermediate Similarity	NPC472534
0.811	Intermediate Similarity	NPC276838
0.811	Intermediate Similarity	NPC329986
0.811	Intermediate Similarity	NPC140092
0.811	Intermediate Similarity	NPC471407
0.811	Intermediate Similarity	NPC232785
0.811	Intermediate Similarity	NPC125077
0.811	Intermediate Similarity	NPC188234
0.811	Intermediate Similarity	NPC476851
0.8103	Intermediate Similarity	NPC293512
0.8099	Intermediate Similarity	NPC176513
0.8099	Intermediate Similarity	NPC470775
0.8095	Intermediate Similarity	NPC179412
0.8095	Intermediate Similarity	NPC298841
0.8095	Intermediate Similarity	NPC471356
0.8092	Intermediate Similarity	NPC596
0.8092	Intermediate Similarity	NPC295885
0.8092	Intermediate Similarity	NPC140045
0.8083	Intermediate Similarity	NPC475633
0.8083	Intermediate Similarity	NPC220293
0.808	Intermediate Similarity	NPC318135
0.808	Intermediate Similarity	NPC470477
0.8077	Intermediate Similarity	NPC262813
0.8067	Intermediate Similarity	NPC37739
0.8067	Intermediate Similarity	NPC130427
0.8067	Intermediate Similarity	NPC46388
0.8065	Intermediate Similarity	NPC107966
0.8065	Intermediate Similarity	NPC249848
0.8065	Intermediate Similarity	NPC40775
0.8065	Intermediate Similarity	NPC235438
0.8062	Intermediate Similarity	NPC477709
0.8062	Intermediate Similarity	NPC142756
0.8062	Intermediate Similarity	NPC476221
0.8062	Intermediate Similarity	NPC476779
0.8062	Intermediate Similarity	NPC104585
0.8062	Intermediate Similarity	NPC157817
0.8062	Intermediate Similarity	NPC225385
0.8062	Intermediate Similarity	NPC298783
0.8051	Intermediate Similarity	NPC475134
0.8051	Intermediate Similarity	NPC475563
0.8051	Intermediate Similarity	NPC235014
0.8051	Intermediate Similarity	NPC101450
0.8049	Intermediate Similarity	NPC471406
0.8047	Intermediate Similarity	NPC25998
0.8047	Intermediate Similarity	NPC16569
0.8047	Intermediate Similarity	NPC478155
0.8047	Intermediate Similarity	NPC159338
0.8047	Intermediate Similarity	NPC477197
0.8047	Intermediate Similarity	NPC476852
0.8047	Intermediate Similarity	NPC253456
0.8033	Intermediate Similarity	NPC286347
0.8033	Intermediate Similarity	NPC276758
0.8033	Intermediate Similarity	NPC470776
0.8033	Intermediate Similarity	NPC18233
0.8031	Intermediate Similarity	NPC329923
0.8031	Intermediate Similarity	NPC473620
0.8031	Intermediate Similarity	NPC477075
0.8031	Intermediate Similarity	NPC311534
0.8031	Intermediate Similarity	NPC475281
0.8031	Intermediate Similarity	NPC477078
0.8017	Intermediate Similarity	NPC235539
0.8017	Intermediate Similarity	NPC152199
0.8017	Intermediate Similarity	NPC134869
0.8016	Intermediate Similarity	NPC181999
0.8015	Intermediate Similarity	NPC471089
0.8015	Intermediate Similarity	NPC190065
0.8015	Intermediate Similarity	NPC141215
0.8	Intermediate Similarity	NPC189884
0.8	Intermediate Similarity	NPC44716
0.8	Intermediate Similarity	NPC477234
0.8	Intermediate Similarity	NPC138334
0.8	Intermediate Similarity	NPC476778
0.8	Intermediate Similarity	NPC47063
0.8	Intermediate Similarity	NPC269315
0.8	Intermediate Similarity	NPC30735
0.8	Intermediate Similarity	NPC271138
0.8	Intermediate Similarity	NPC478066
0.8	Intermediate Similarity	NPC51978
0.8	Intermediate Similarity	NPC2370
0.8	Intermediate Similarity	NPC281148
0.8	Intermediate Similarity	NPC25909
0.8	Intermediate Similarity	NPC204458
0.8	Intermediate Similarity	NPC476777
0.8	Intermediate Similarity	NPC235405
0.8	Intermediate Similarity	NPC27363
0.7984	Intermediate Similarity	NPC204731
0.7984	Intermediate Similarity	NPC42670
0.7984	Intermediate Similarity	NPC19124
0.7984	Intermediate Similarity	NPC93416
0.7983	Intermediate Similarity	NPC179798
0.7983	Intermediate Similarity	NPC304180
0.7983	Intermediate Similarity	NPC191763
0.7969	Intermediate Similarity	NPC9499
0.7969	Intermediate Similarity	NPC469752
0.7969	Intermediate Similarity	NPC471352
0.7969	Intermediate Similarity	NPC86159
0.7969	Intermediate Similarity	NPC470912
0.7969	Intermediate Similarity	NPC471360
0.7969	Intermediate Similarity	NPC70542
0.7969	Intermediate Similarity	NPC91
0.7969	Intermediate Similarity	NPC469751
0.7969	Intermediate Similarity	NPC470913
0.7969	Intermediate Similarity	NPC473593
0.7969	Intermediate Similarity	NPC471359
0.7969	Intermediate Similarity	NPC477077
0.7969	Intermediate Similarity	NPC251866
0.7969	Intermediate Similarity	NPC471358
0.7969	Intermediate Similarity	NPC180079
0.7969	Intermediate Similarity	NPC469755
0.7969	Intermediate Similarity	NPC284406
0.7969	Intermediate Similarity	NPC219085
0.7969	Intermediate Similarity	NPC6108
0.7969	Intermediate Similarity	NPC471361
0.7969	Intermediate Similarity	NPC477079
0.7969	Intermediate Similarity	NPC477076
0.7969	Intermediate Similarity	NPC17896
0.7969	Intermediate Similarity	NPC469754
0.7969	Intermediate Similarity	NPC89514
0.7969	Intermediate Similarity	NPC10823

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 NPC473231 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1619
0.2-0.3	3881
0.3-0.4	2314
0.4-0.5	619
0.5-0.6	292
0.6-0.7	186
0.7-0.8	30
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.816	Intermediate Similarity	NPD7507	Approved
0.7969	Intermediate Similarity	NPD7319	Approved
0.7881	Intermediate Similarity	NPD6686	Approved
0.784	Intermediate Similarity	NPD8517	Approved
0.784	Intermediate Similarity	NPD8516	Approved
0.784	Intermediate Similarity	NPD8513	Phase 3
0.784	Intermediate Similarity	NPD8515	Approved
0.7805	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD7736	Approved
0.7717	Intermediate Similarity	NPD8328	Phase 3
0.7686	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD8293	Discontinued
0.7667	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6370	Approved
0.7422	Intermediate Similarity	NPD8033	Approved
0.7419	Intermediate Similarity	NPD8133	Approved
0.7385	Intermediate Similarity	NPD7492	Approved
0.7355	Intermediate Similarity	NPD6412	Phase 2
0.7344	Intermediate Similarity	NPD8294	Approved
0.7344	Intermediate Similarity	NPD8377	Approved
0.7344	Intermediate Similarity	NPD6059	Approved
0.7344	Intermediate Similarity	NPD6054	Approved
0.7328	Intermediate Similarity	NPD6616	Approved
0.7323	Intermediate Similarity	NPD7327	Approved
0.7323	Intermediate Similarity	NPD7328	Approved
0.7287	Intermediate Similarity	NPD8296	Approved
0.7287	Intermediate Similarity	NPD8335	Approved
0.7287	Intermediate Similarity	NPD8380	Approved
0.7287	Intermediate Similarity	NPD8378	Approved
0.7287	Intermediate Similarity	NPD8379	Approved
0.7273	Intermediate Similarity	NPD7078	Approved
0.7266	Intermediate Similarity	NPD7516	Approved
0.72	Intermediate Similarity	NPD8297	Approved
0.72	Intermediate Similarity	NPD6882	Approved
0.7154	Intermediate Similarity	NPD6016	Approved
0.7154	Intermediate Similarity	NPD7503	Approved
0.7154	Intermediate Similarity	NPD6015	Approved
0.7154	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8074	Phase 3
0.7109	Intermediate Similarity	NPD7115	Discovery
0.7109	Intermediate Similarity	NPD6009	Approved
0.7099	Intermediate Similarity	NPD5988	Approved
0.7097	Intermediate Similarity	NPD6373	Approved
0.7097	Intermediate Similarity	NPD6372	Approved
0.704	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7320	Approved
0.7	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD7639	Approved
0.6992	Remote Similarity	NPD6675	Approved
0.6992	Remote Similarity	NPD5739	Approved
0.6992	Remote Similarity	NPD7128	Approved
0.6992	Remote Similarity	NPD6402	Approved
0.6984	Remote Similarity	NPD6650	Approved
0.6984	Remote Similarity	NPD6649	Approved
0.696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6319	Approved
0.6935	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6053	Discontinued
0.6917	Remote Similarity	NPD7638	Approved
0.6917	Remote Similarity	NPD4225	Approved
0.688	Remote Similarity	NPD6899	Approved
0.688	Remote Similarity	NPD6881	Approved
0.6875	Remote Similarity	NPD4632	Approved
0.6855	Remote Similarity	NPD6008	Approved
0.685	Remote Similarity	NPD8130	Phase 1
0.6838	Remote Similarity	NPD6033	Approved
0.6812	Remote Similarity	NPD7260	Phase 2
0.68	Remote Similarity	NPD5701	Approved
0.68	Remote Similarity	NPD5697	Approved
0.68	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5779	Approved
0.678	Remote Similarity	NPD6399	Phase 3
0.678	Remote Similarity	NPD5778	Approved
0.6777	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7290	Approved
0.6772	Remote Similarity	NPD6883	Approved
0.6772	Remote Similarity	NPD7102	Approved
0.6763	Remote Similarity	NPD6845	Suspended
0.6719	Remote Similarity	NPD6617	Approved
0.6719	Remote Similarity	NPD6847	Approved
0.6719	Remote Similarity	NPD6869	Approved
0.6695	Remote Similarity	NPD7983	Approved
0.6694	Remote Similarity	NPD7902	Approved
0.6694	Remote Similarity	NPD6084	Phase 2
0.6694	Remote Similarity	NPD6083	Phase 2
0.6693	Remote Similarity	NPD6013	Approved
0.6693	Remote Similarity	NPD6014	Approved
0.6693	Remote Similarity	NPD6012	Approved
0.6691	Remote Similarity	NPD8451	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6067	Discontinued
0.6642	Remote Similarity	NPD6921	Approved
0.6642	Remote Similarity	NPD8448	Approved
0.6642	Remote Similarity	NPD5983	Phase 2
0.6619	Remote Similarity	NPD8390	Approved
0.6619	Remote Similarity	NPD8392	Approved
0.6619	Remote Similarity	NPD8391	Approved
0.6618	Remote Similarity	NPD8299	Approved
0.6618	Remote Similarity	NPD8340	Approved
0.6618	Remote Similarity	NPD8341	Approved
0.6618	Remote Similarity	NPD8342	Approved
0.6614	Remote Similarity	NPD6011	Approved
0.6613	Remote Similarity	NPD5211	Phase 2
0.6612	Remote Similarity	NPD4697	Phase 3
0.661	Remote Similarity	NPD6698	Approved
0.661	Remote Similarity	NPD46	Approved
0.6589	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7748	Approved
0.6569	Remote Similarity	NPD6336	Discontinued
0.6557	Remote Similarity	NPD4755	Approved
0.6555	Remote Similarity	NPD6411	Approved
0.6529	Remote Similarity	NPD5695	Phase 3
0.6512	Remote Similarity	NPD6371	Approved
0.6508	Remote Similarity	NPD5141	Approved
0.6508	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5696	Approved
0.6503	Remote Similarity	NPD7799	Discontinued
0.648	Remote Similarity	NPD7632	Discontinued
0.6458	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4700	Approved
0.6452	Remote Similarity	NPD5286	Approved
0.6452	Remote Similarity	NPD4696	Approved
0.6452	Remote Similarity	NPD5285	Approved
0.6446	Remote Similarity	NPD7900	Approved
0.6446	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7515	Phase 2
0.6417	Remote Similarity	NPD8034	Phase 2
0.6417	Remote Similarity	NPD8035	Phase 2
0.6397	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6274	Approved
0.6387	Remote Similarity	NPD6101	Approved
0.6387	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD4634	Approved
0.6383	Remote Similarity	NPD5956	Approved
0.6379	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.637	Remote Similarity	NPD7101	Approved
0.637	Remote Similarity	NPD7100	Approved
0.6349	Remote Similarity	NPD5224	Approved
0.6349	Remote Similarity	NPD5225	Approved
0.6349	Remote Similarity	NPD5226	Approved
0.6349	Remote Similarity	NPD4633	Approved
0.6341	Remote Similarity	NPD7839	Suspended
0.6328	Remote Similarity	NPD4768	Approved
0.6328	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD5282	Discontinued
0.6304	Remote Similarity	NPD7642	Approved
0.6303	Remote Similarity	NPD6672	Approved
0.6303	Remote Similarity	NPD5737	Approved
0.6299	Remote Similarity	NPD5175	Approved
0.6299	Remote Similarity	NPD5174	Approved
0.6296	Remote Similarity	NPD6335	Approved
0.6281	Remote Similarity	NPD5693	Phase 1
0.6281	Remote Similarity	NPD7637	Suspended
0.6277	Remote Similarity	NPD6908	Approved
0.6277	Remote Similarity	NPD6909	Approved
0.627	Remote Similarity	NPD5344	Discontinued
0.627	Remote Similarity	NPD5223	Approved
0.626	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.6239	Remote Similarity	NPD4786	Approved
0.6231	Remote Similarity	NPD4730	Approved
0.6231	Remote Similarity	NPD4729	Approved
0.6222	Remote Similarity	NPD6317	Approved
0.621	Remote Similarity	NPD5222	Approved
0.621	Remote Similarity	NPD5221	Approved
0.621	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3667	Approved
0.6198	Remote Similarity	NPD7838	Discovery
0.6187	Remote Similarity	NPD7830	Approved
0.6187	Remote Similarity	NPD7122	Discontinued
0.6187	Remote Similarity	NPD7829	Approved
0.6186	Remote Similarity	NPD1694	Approved
0.6186	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6313	Approved
0.6176	Remote Similarity	NPD7641	Discontinued
0.6176	Remote Similarity	NPD6314	Approved
0.6172	Remote Similarity	NPD4754	Approved
0.6167	Remote Similarity	NPD6903	Approved
0.6167	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.616	Remote Similarity	NPD5173	Approved
0.6159	Remote Similarity	NPD8266	Approved
0.6159	Remote Similarity	NPD8267	Approved
0.6159	Remote Similarity	NPD8269	Approved
0.6159	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD8444	Approved
0.6159	Remote Similarity	NPD8268	Approved
0.6148	Remote Similarity	NPD6079	Approved
0.6148	Remote Similarity	NPD6868	Approved
0.6136	Remote Similarity	NPD5248	Approved
0.6136	Remote Similarity	NPD5250	Approved
0.6136	Remote Similarity	NPD5247	Approved
0.6136	Remote Similarity	NPD5249	Phase 3
0.6136	Remote Similarity	NPD5251	Approved
0.6134	Remote Similarity	NPD6684	Approved
0.6134	Remote Similarity	NPD7521	Approved
0.6134	Remote Similarity	NPD6098	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