NPASS Compound

Structure

NPC476174 OpenBabel07101718192D 34 38 0 0 1 0 0 0 0 0999 V2000 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8973 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 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 -2.6831 -0.3090 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9192 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 -3.2500 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5591 6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2719 5.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 1 1 1 0 0 0 18 21 1 0 0 0 0 19 25 1 0 0 0 0 20 31 1 0 0 0 0 21 27 1 6 0 0 0 22 26 1 0 0 0 0 22 29 1 6 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	511.905
LogP:	4.424
LogD:	4.038
LogS:	-4.511
# Rotatable Bonds:	6
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.469
Synthetic Accessibility Score:	5.514
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.409
MDCK Permeability:	1.452193555451231e-05
Pgp-inhibitor:	0.213
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.663
Plasma Protein Binding (PPB):	91.5311050415039%
Volume Distribution (VD):	0.89
Pgp-substrate:	3.465693473815918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.563
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.917
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.414
CYP3A4-inhibitor:	0.461
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	5.583
Half-life (T1/2):	0.707

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.342
Drug-inuced Liver Injury (DILI):	0.201
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.255
Maximum Recommended Daily Dose:	0.448
Skin Sensitization:	0.661
Carcinogencity:	0.488
Eye Corrosion:	0.016
Eye Irritation:	0.052
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC476174

Natural Product ID:	NPC476174
*Common Name:**	WQMAGDSBYCIARL-VXEOXPBSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WQMAGDSBYCIARL-VXEOXPBSSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-18(15-20(31)16-19(2)25(33)34)21-9-11-28(6)23-8-7-22-26(3,4)24(32)10-12-29(22)17-30(23,29)14-13-27(21,28)5/h16,18,20-23,31H,7-15,17H2,1-6H3,(H,33,34)/b19-16+/t18-,20?,21-,22+,23+,27-,28+,29-,30+/m1/s1
SMILES:	C[C@H](CC(/C=C(C)/C(=O)O)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)C(=O)CC[C@]54C[C@@]35CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550926
PubChem CID:	45271778
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757720]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593279]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	China	n.a.	PMID[19278239]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	Ywar Taw village, Shan State of Myanmar	2006-Dec	PMID[19572611]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO41067	Trigona minor	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28783356]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	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
Others	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	=	50.0	uM	PMID[507877]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	28.0	uM	PMID[507877]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	16.8	uM	PMID[507879]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	PC50	=	32.3	uM	PMID[507878]

☑ 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 NPC476174 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	184
0.1-0.2	1111
0.2-0.3	4811
0.3-0.4	13317
0.4-0.5	8550
0.5-0.6	6339
0.6-0.7	5615
0.7-0.8	2503
0.8-0.85	209
0.85-0.9	40
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC29152
0.956	High Similarity	NPC156546
0.9121	High Similarity	NPC476304
0.9101	High Similarity	NPC117122
0.9091	High Similarity	NPC186975
0.9091	High Similarity	NPC70661
0.9032	High Similarity	NPC472941
0.9032	High Similarity	NPC456
0.9022	High Similarity	NPC476186
0.9011	High Similarity	NPC476187
0.9011	High Similarity	NPC74296
0.9011	High Similarity	NPC470113
0.9011	High Similarity	NPC23217
0.9011	High Similarity	NPC110923
0.9	High Similarity	NPC66344
0.8989	High Similarity	NPC236618
0.8977	High Similarity	NPC60350
0.8864	High Similarity	NPC178025
0.8864	High Similarity	NPC194937
0.8864	High Similarity	NPC181743
0.8864	High Similarity	NPC476038
0.8864	High Similarity	NPC16287
0.8842	High Similarity	NPC166745
0.8842	High Similarity	NPC235464
0.8842	High Similarity	NPC197386
0.8842	High Similarity	NPC98868
0.883	High Similarity	NPC250757
0.883	High Similarity	NPC195366
0.883	High Similarity	NPC301534
0.883	High Similarity	NPC114743
0.8804	High Similarity	NPC473998
0.8791	High Similarity	NPC214387
0.8791	High Similarity	NPC473999
0.8791	High Similarity	NPC262043
0.8791	High Similarity	NPC309603
0.8778	High Similarity	NPC136948
0.8764	High Similarity	NPC471224
0.8764	High Similarity	NPC283733
0.875	High Similarity	NPC470074
0.875	High Similarity	NPC287833
0.8737	High Similarity	NPC253826
0.8723	High Similarity	NPC293052
0.8723	High Similarity	NPC173875
0.8723	High Similarity	NPC469995
0.8723	High Similarity	NPC174948
0.8723	High Similarity	NPC318282
0.871	High Similarity	NPC474736
0.8696	High Similarity	NPC477149
0.8696	High Similarity	NPC48010
0.8696	High Similarity	NPC477147
0.8681	High Similarity	NPC472870
0.8667	High Similarity	NPC472869
0.866	High Similarity	NPC472924
0.8652	High Similarity	NPC85774
0.8652	High Similarity	NPC214043
0.8652	High Similarity	NPC248758
0.8652	High Similarity	NPC472864
0.8652	High Similarity	NPC164577
0.8652	High Similarity	NPC19849
0.8652	High Similarity	NPC165064
0.8636	High Similarity	NPC477858
0.8632	High Similarity	NPC328371
0.8617	High Similarity	NPC8993
0.8602	High Similarity	NPC475806
0.8602	High Similarity	NPC473986
0.8602	High Similarity	NPC474018
0.8587	High Similarity	NPC262858
0.8587	High Similarity	NPC472240
0.8587	High Similarity	NPC146554
0.8587	High Similarity	NPC281524
0.8571	High Similarity	NPC93778
0.8571	High Similarity	NPC96496
0.8571	High Similarity	NPC476293
0.8571	High Similarity	NPC293753
0.8557	High Similarity	NPC201406
0.8557	High Similarity	NPC51370
0.8557	High Similarity	NPC476274
0.8556	High Similarity	NPC29447
0.8556	High Similarity	NPC474083
0.8542	High Similarity	NPC107243
0.8542	High Similarity	NPC108078
0.8542	High Similarity	NPC475894
0.8542	High Similarity	NPC320306
0.8539	High Similarity	NPC215893
0.8539	High Similarity	NPC97913
0.8526	High Similarity	NPC33473
0.8511	High Similarity	NPC472930
0.8511	High Similarity	NPC12722
0.85	High Similarity	NPC189863
0.8495	Intermediate Similarity	NPC126993
0.8485	Intermediate Similarity	NPC112009
0.8485	Intermediate Similarity	NPC476237
0.8485	Intermediate Similarity	NPC312900
0.8478	Intermediate Similarity	NPC104560
0.8469	Intermediate Similarity	NPC118174
0.8469	Intermediate Similarity	NPC476240
0.8469	Intermediate Similarity	NPC476223
0.8469	Intermediate Similarity	NPC99411
0.8469	Intermediate Similarity	NPC224720
0.8469	Intermediate Similarity	NPC282524
0.8462	Intermediate Similarity	NPC155011
0.8462	Intermediate Similarity	NPC322159
0.8462	Intermediate Similarity	NPC474732
0.8462	Intermediate Similarity	NPC474778
0.8462	Intermediate Similarity	NPC31564
0.8462	Intermediate Similarity	NPC475007
0.8462	Intermediate Similarity	NPC469994
0.8462	Intermediate Similarity	NPC145879
0.8462	Intermediate Similarity	NPC474733
0.8454	Intermediate Similarity	NPC57079
0.8454	Intermediate Similarity	NPC471717
0.8454	Intermediate Similarity	NPC108368
0.8444	Intermediate Similarity	NPC473246
0.8444	Intermediate Similarity	NPC472865
0.8427	Intermediate Similarity	NPC472239
0.8427	Intermediate Similarity	NPC320514
0.8421	Intermediate Similarity	NPC124207
0.8421	Intermediate Similarity	NPC184870
0.8421	Intermediate Similarity	NPC469406
0.8421	Intermediate Similarity	NPC299100
0.8404	Intermediate Similarity	NPC204341
0.8404	Intermediate Similarity	NPC272746
0.8404	Intermediate Similarity	NPC154101
0.84	Intermediate Similarity	NPC235889
0.8387	Intermediate Similarity	NPC310236
0.8387	Intermediate Similarity	NPC31985
0.8387	Intermediate Similarity	NPC2983
0.8387	Intermediate Similarity	NPC475921
0.8387	Intermediate Similarity	NPC477943
0.8387	Intermediate Similarity	NPC1015
0.8387	Intermediate Similarity	NPC474704
0.8387	Intermediate Similarity	NPC477973
0.8387	Intermediate Similarity	NPC123912
0.8387	Intermediate Similarity	NPC128496
0.8384	Intermediate Similarity	NPC136289
0.8384	Intermediate Similarity	NPC204450
0.8384	Intermediate Similarity	NPC234892
0.8384	Intermediate Similarity	NPC195290
0.837	Intermediate Similarity	NPC317590
0.837	Intermediate Similarity	NPC475740
0.837	Intermediate Similarity	NPC474684
0.837	Intermediate Similarity	NPC58063
0.837	Intermediate Similarity	NPC142361
0.837	Intermediate Similarity	NPC128644
0.8367	Intermediate Similarity	NPC327431
0.8367	Intermediate Similarity	NPC471041
0.8367	Intermediate Similarity	NPC266955
0.8352	Intermediate Similarity	NPC76518
0.8352	Intermediate Similarity	NPC269638
0.8352	Intermediate Similarity	NPC469948
0.8351	Intermediate Similarity	NPC57416
0.8333	Intermediate Similarity	NPC139459
0.8333	Intermediate Similarity	NPC84383
0.8333	Intermediate Similarity	NPC271195
0.8333	Intermediate Similarity	NPC37646
0.8333	Intermediate Similarity	NPC472740
0.8333	Intermediate Similarity	NPC472932
0.8333	Intermediate Similarity	NPC180950
0.8317	Intermediate Similarity	NPC181265
0.8316	Intermediate Similarity	NPC109305
0.8316	Intermediate Similarity	NPC243866
0.8316	Intermediate Similarity	NPC214697
0.8316	Intermediate Similarity	NPC472871
0.8316	Intermediate Similarity	NPC69454
0.8316	Intermediate Similarity	NPC38232
0.8315	Intermediate Similarity	NPC147066
0.8315	Intermediate Similarity	NPC278459
0.8315	Intermediate Similarity	NPC477372
0.83	Intermediate Similarity	NPC180204
0.83	Intermediate Similarity	NPC236390
0.8298	Intermediate Similarity	NPC85173
0.8298	Intermediate Similarity	NPC320026
0.8298	Intermediate Similarity	NPC469400
0.8298	Intermediate Similarity	NPC472866
0.8295	Intermediate Similarity	NPC158846
0.8283	Intermediate Similarity	NPC115899
0.8283	Intermediate Similarity	NPC302537
0.8283	Intermediate Similarity	NPC163372
0.8283	Intermediate Similarity	NPC81530
0.828	Intermediate Similarity	NPC193843
0.828	Intermediate Similarity	NPC249889
0.828	Intermediate Similarity	NPC16377
0.8265	Intermediate Similarity	NPC194196
0.8265	Intermediate Similarity	NPC114274
0.8265	Intermediate Similarity	NPC103051
0.8265	Intermediate Similarity	NPC478056
0.8247	Intermediate Similarity	NPC40765
0.8247	Intermediate Similarity	NPC3772
0.8247	Intermediate Similarity	NPC249954
0.8247	Intermediate Similarity	NPC155676
0.8247	Intermediate Similarity	NPC7124
0.8247	Intermediate Similarity	NPC235053
0.8247	Intermediate Similarity	NPC471039
0.8247	Intermediate Similarity	NPC471463
0.8247	Intermediate Similarity	NPC243525
0.8247	Intermediate Similarity	NPC327788
0.8242	Intermediate Similarity	NPC237712
0.8242	Intermediate Similarity	NPC161423
0.8242	Intermediate Similarity	NPC58841
0.8242	Intermediate Similarity	NPC227064

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 NPC476174 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1377
0.2-0.3	3793
0.3-0.4	2659
0.4-0.5	664
0.5-0.6	178
0.6-0.7	182
0.7-0.8	143
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8242	Intermediate Similarity	NPD3133	Approved
0.8242	Intermediate Similarity	NPD4786	Approved
0.8242	Intermediate Similarity	NPD3665	Phase 1
0.8242	Intermediate Similarity	NPD3666	Approved
0.8211	Intermediate Similarity	NPD6079	Approved
0.8211	Intermediate Similarity	NPD7515	Phase 2
0.8191	Intermediate Similarity	NPD5328	Approved
0.8182	Intermediate Similarity	NPD7640	Approved
0.8182	Intermediate Similarity	NPD7639	Approved
0.8163	Intermediate Similarity	NPD6083	Phase 2
0.8163	Intermediate Similarity	NPD6084	Phase 2
0.8125	Intermediate Similarity	NPD6399	Phase 3
0.8085	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD6672	Approved
0.8085	Intermediate Similarity	NPD5737	Approved
0.8081	Intermediate Similarity	NPD7638	Approved
0.8065	Intermediate Similarity	NPD7334	Approved
0.8065	Intermediate Similarity	NPD6684	Approved
0.8065	Intermediate Similarity	NPD3618	Phase 1
0.8065	Intermediate Similarity	NPD7521	Approved
0.8065	Intermediate Similarity	NPD6409	Approved
0.8065	Intermediate Similarity	NPD7146	Approved
0.8065	Intermediate Similarity	NPD5330	Approved
0.8022	Intermediate Similarity	NPD3667	Approved
0.8	Intermediate Similarity	NPD4753	Phase 2
0.7978	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4788	Approved
0.7895	Intermediate Similarity	NPD6903	Approved
0.789	Intermediate Similarity	NPD7115	Discovery
0.7879	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5222	Approved
0.7879	Intermediate Similarity	NPD5221	Approved
0.7872	Intermediate Similarity	NPD5279	Phase 3
0.7857	Intermediate Similarity	NPD7748	Approved
0.7843	Intermediate Similarity	NPD5211	Phase 2
0.7826	Intermediate Similarity	NPD4223	Phase 3
0.7826	Intermediate Similarity	NPD4221	Approved
0.781	Intermediate Similarity	NPD6881	Approved
0.781	Intermediate Similarity	NPD6899	Approved
0.78	Intermediate Similarity	NPD5173	Approved
0.7788	Intermediate Similarity	NPD7128	Approved
0.7788	Intermediate Similarity	NPD5739	Approved
0.7788	Intermediate Similarity	NPD6675	Approved
0.7788	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5210	Approved
0.7778	Intermediate Similarity	NPD5695	Phase 3
0.7778	Intermediate Similarity	NPD4629	Approved
0.7766	Intermediate Similarity	NPD5329	Approved
0.7755	Intermediate Similarity	NPD4202	Approved
0.7723	Intermediate Similarity	NPD5696	Approved
0.7714	Intermediate Similarity	NPD5697	Approved
0.77	Intermediate Similarity	NPD4697	Phase 3
0.7692	Intermediate Similarity	NPD5141	Approved
0.7664	Intermediate Similarity	NPD7102	Approved
0.7664	Intermediate Similarity	NPD6883	Approved
0.7664	Intermediate Similarity	NPD7290	Approved
0.766	Intermediate Similarity	NPD4197	Approved
0.7653	Intermediate Similarity	NPD5281	Approved
0.7653	Intermediate Similarity	NPD5284	Approved
0.7647	Intermediate Similarity	NPD5286	Approved
0.7647	Intermediate Similarity	NPD4696	Approved
0.7647	Intermediate Similarity	NPD5285	Approved
0.7642	Intermediate Similarity	NPD7320	Approved
0.7642	Intermediate Similarity	NPD6011	Approved
0.7634	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6904	Approved
0.7629	Intermediate Similarity	NPD6673	Approved
0.7629	Intermediate Similarity	NPD6080	Approved
0.7624	Intermediate Similarity	NPD7902	Approved
0.7624	Intermediate Similarity	NPD4755	Approved
0.7593	Intermediate Similarity	NPD6649	Approved
0.7593	Intermediate Similarity	NPD6617	Approved
0.7593	Intermediate Similarity	NPD8130	Phase 1
0.7593	Intermediate Similarity	NPD6847	Approved
0.7593	Intermediate Similarity	NPD6650	Approved
0.7593	Intermediate Similarity	NPD6869	Approved
0.7579	Intermediate Similarity	NPD5363	Approved
0.7573	Intermediate Similarity	NPD5223	Approved
0.757	Intermediate Similarity	NPD6372	Approved
0.757	Intermediate Similarity	NPD6373	Approved
0.757	Intermediate Similarity	NPD6014	Approved
0.757	Intermediate Similarity	NPD6012	Approved
0.757	Intermediate Similarity	NPD6013	Approved
0.7551	Intermediate Similarity	NPD5785	Approved
0.7547	Intermediate Similarity	NPD5701	Approved
0.7523	Intermediate Similarity	NPD6882	Approved
0.7523	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD4623	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD7632	Discontinued
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD4519	Discontinued
0.75	Intermediate Similarity	NPD5224	Approved
0.7476	Intermediate Similarity	NPD4700	Approved
0.7476	Intermediate Similarity	NPD6404	Discontinued
0.7475	Intermediate Similarity	NPD5693	Phase 1
0.7475	Intermediate Similarity	NPD8035	Phase 2
0.7475	Intermediate Similarity	NPD8034	Phase 2
0.7474	Intermediate Similarity	NPD3668	Phase 3
0.7449	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5174	Approved
0.7429	Intermediate Similarity	NPD5175	Approved
0.7419	Intermediate Similarity	NPD7525	Registered
0.7419	Intermediate Similarity	NPD4695	Discontinued
0.7391	Intermediate Similarity	NPD3617	Approved
0.7368	Intermediate Similarity	NPD5362	Discontinued
0.7363	Intermediate Similarity	NPD6117	Approved
0.7347	Intermediate Similarity	NPD5208	Approved
0.7333	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7900	Approved
0.7327	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6001	Approved
0.7321	Intermediate Similarity	NPD6868	Approved
0.732	Intermediate Similarity	NPD6098	Approved
0.732	Intermediate Similarity	NPD5280	Approved
0.732	Intermediate Similarity	NPD4694	Approved
0.7315	Intermediate Similarity	NPD6686	Approved
0.7312	Intermediate Similarity	NPD4195	Approved
0.73	Intermediate Similarity	NPD6050	Approved
0.73	Intermediate Similarity	NPD7637	Suspended
0.7297	Intermediate Similarity	NPD4632	Approved
0.7283	Intermediate Similarity	NPD6116	Phase 1
0.7264	Intermediate Similarity	NPD4754	Approved
0.7263	Intermediate Similarity	NPD4269	Approved
0.7263	Intermediate Similarity	NPD4270	Approved
0.7253	Intermediate Similarity	NPD6942	Approved
0.7253	Intermediate Similarity	NPD7339	Approved
0.7222	Intermediate Similarity	NPD6412	Phase 2
0.7212	Intermediate Similarity	NPD4225	Approved
0.7204	Intermediate Similarity	NPD6697	Approved
0.7204	Intermediate Similarity	NPD6115	Approved
0.7204	Intermediate Similarity	NPD6114	Approved
0.7204	Intermediate Similarity	NPD6118	Approved
0.72	Intermediate Similarity	NPD5692	Phase 3
0.7193	Intermediate Similarity	NPD6335	Approved
0.7191	Intermediate Similarity	NPD4747	Approved
0.7191	Intermediate Similarity	NPD4691	Approved
0.7184	Intermediate Similarity	NPD7614	Phase 1
0.7179	Intermediate Similarity	NPD7604	Phase 2
0.7168	Intermediate Similarity	NPD6274	Approved
0.7156	Intermediate Similarity	NPD5168	Approved
0.7156	Intermediate Similarity	NPD4729	Approved
0.7156	Intermediate Similarity	NPD5128	Approved
0.7156	Intermediate Similarity	NPD4730	Approved
0.713	Intermediate Similarity	NPD7101	Approved
0.713	Intermediate Similarity	NPD6008	Approved
0.713	Intermediate Similarity	NPD4767	Approved
0.713	Intermediate Similarity	NPD4768	Approved
0.713	Intermediate Similarity	NPD7100	Approved
0.7129	Intermediate Similarity	NPD5694	Approved
0.7111	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6081	Approved
0.7111	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6009	Approved
0.7105	Intermediate Similarity	NPD6317	Approved
0.71	Intermediate Similarity	NPD6051	Approved
0.7079	Intermediate Similarity	NPD4137	Phase 3
0.7059	Intermediate Similarity	NPD5133	Approved
0.7053	Intermediate Similarity	NPD4252	Approved
0.7043	Intermediate Similarity	NPD6313	Approved
0.7043	Intermediate Similarity	NPD6314	Approved
0.7041	Intermediate Similarity	NPD1694	Approved
0.703	Intermediate Similarity	NPD5207	Approved
0.7027	Intermediate Similarity	NPD5135	Approved
0.7027	Intermediate Similarity	NPD5251	Approved
0.7027	Intermediate Similarity	NPD5169	Approved
0.7027	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5250	Approved
0.7027	Intermediate Similarity	NPD5249	Phase 3
0.7027	Intermediate Similarity	NPD4634	Approved
0.7027	Intermediate Similarity	NPD5248	Approved
0.7027	Intermediate Similarity	NPD5247	Approved
0.701	Intermediate Similarity	NPD5331	Approved
0.701	Intermediate Similarity	NPD5332	Approved
0.7	Intermediate Similarity	NPD4789	Approved
0.7	Intermediate Similarity	NPD4245	Approved
0.7	Intermediate Similarity	NPD4244	Approved
0.6989	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6902	Approved
0.6979	Remote Similarity	NPD4790	Discontinued
0.697	Remote Similarity	NPD5786	Approved
0.6964	Remote Similarity	NPD5127	Approved
0.6964	Remote Similarity	NPD5215	Approved
0.6964	Remote Similarity	NPD5216	Approved
0.6964	Remote Similarity	NPD5217	Approved
0.6957	Remote Similarity	NPD4058	Approved
0.6957	Remote Similarity	NPD6926	Approved
0.6957	Remote Similarity	NPD5733	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