NPASS Compound

Structure

NPC231797 OpenBabel07101718322D 45 50 0 0 1 0 0 0 0 0999 V2000 -6.1964 -6.0712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5491 -6.6064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2693 -3.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9330 2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0670 2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6244 -2.6635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6244 0.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0670 -1.6160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9310 -4.7043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9092 -4.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6220 -3.7532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -0.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5699 -1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9821 -0.4410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 -1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6292 1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2182 -5.8632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2912 -3.0101 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9821 -2.0590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7631 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1651 -0.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4330 -0.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2990 0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7631 -0.2500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8971 -0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0311 -0.2500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0311 0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4330 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4330 1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 -1.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0311 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2990 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4330 0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4952 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6292 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8971 -1.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1651 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0670 -1.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8971 1.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1651 1.2500 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 21 2 0 0 0 0 2 21 1 0 0 0 0 4 33 1 0 0 0 0 5 33 1 0 0 0 0 6 34 1 0 0 0 0 8 42 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 25 1 0 0 0 0 16 35 1 0 0 0 0 18 19 1 0 0 0 0 18 34 1 0 0 0 0 20 38 1 0 0 0 0 22 3 1 1 0 0 0 22 23 1 0 0 0 0 23 34 1 1 0 0 0 24 20 1 6 0 0 0 24 28 1 0 0 0 0 24 43 1 0 0 0 0 25 35 1 6 0 0 0 25 36 1 0 0 0 0 26 36 1 1 0 0 0 26 37 1 0 0 0 0 27 33 1 0 0 0 0 27 44 1 1 0 0 0 28 29 1 0 0 0 0 28 39 1 1 0 0 0 29 30 1 0 0 0 0 29 40 1 6 0 0 0 30 31 1 0 0 0 0 30 41 1 1 0 0 0 31 43 1 0 0 0 0 31 44 1 6 0 0 0 32 36 1 1 0 0 0 32 42 1 0 0 0 0 32 45 1 0 0 0 0 33 37 1 0 0 0 0 34 35 1 1 0 0 0 35 7 1 6 0 0 0 36 19 1 6 0 0 0 37 17 1 1 0 0 0 37 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	630.41
Volume:	659.582
LogP:	4.878
LogD:	4.277
LogS:	-4.9
# Rotatable Bonds:	8
TPSA:	117.84
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.221
Synthetic Accessibility Score:	7.031
Fsp3:	0.838
Lipinski Rule-of-5:	Accepted
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:	-4.946
MDCK Permeability:	5.007524578104494e-06
Pgp-inhibitor:	0.094
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.571

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	90.61775207519531%
Volume Distribution (VD):	1.411
Pgp-substrate:	4.715393543243408%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.417
CYP3A4-inhibitor:	0.761
CYP3A4-substrate:	0.562

ADMET: Excretion

Clearance (CL):	1.39
Half-life (T1/2):	0.482

ADMET: Toxicity

hERG Blockers:	0.261
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.453
Skin Sensitization:	0.688
Carcinogencity:	0.195
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC231797

Natural Product ID:	NPC231797
*Common Name:**	Charantoside I
IUPAC Name:	n.a.
Synonyms:	charantoside I
Standard InCHIKey:	XTMJHIYXJLZGJC-CGLOHJMOSA-N
Standard InCHI:	InChI=1S/C37H58O8/c1-21(2)10-9-11-22(3)23-14-16-35(7)25-15-17-37-26(36(25,32(42-8)45-37)19-18-34(23,35)6)12-13-27(33(37,4)5)44-31-30(41)29(40)28(39)24(20-38)43-31/h9-10,15,17,22-32,38-41H,1,11-14,16,18-20H2,2-8H3/b10-9+/t22-,23-,24-,25+,26+,27+,28-,29+,30-,31+,32-,34-,35+,36+,37-/m1/s1
SMILES:	C=C(C)/C=C/C[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3C=C[C@@]45[C@@H](CC[C@@H](C4(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)[C@@]3(CC[C@]12C)[C@H](OC)O5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL411796
PubChem CID:	23626009
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17685651]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[18637688]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24836069]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621938]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Vines	n.a.	n.a.	PMID[32357011]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8182	Momordica charantia	Species	Cucurbitaceae	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	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[565937]
NPT2	Others	Unspecified		Inhibition	=	12.6	%	PMID[565937]
NPT2	Others	Unspecified		Inhibition	=	35.4	%	PMID[565937]
NPT2	Others	Unspecified		Inhibition	=	81.1	%	PMID[565937]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[565937]

☑ 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 NPC231797 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	278
0.1-0.2	1507
0.2-0.3	4954
0.3-0.4	11287
0.4-0.5	11054
0.5-0.6	6880
0.6-0.7	4347
0.7-0.8	1876
0.8-0.85	433
0.85-0.9	57
0.9-0.95	14
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC208189
0.9903	High Similarity	NPC65034
0.9806	High Similarity	NPC103627
0.9806	High Similarity	NPC191439
0.9806	High Similarity	NPC170974
0.9709	High Similarity	NPC473328
0.9709	High Similarity	NPC28844
0.9709	High Similarity	NPC473318
0.9615	High Similarity	NPC65155
0.9333	High Similarity	NPC14630
0.9333	High Similarity	NPC250089
0.9333	High Similarity	NPC157530
0.9327	High Similarity	NPC33053
0.9252	High Similarity	NPC216595
0.9252	High Similarity	NPC473567
0.9223	High Similarity	NPC471886
0.9223	High Similarity	NPC471888
0.9223	High Similarity	NPC471885
0.9223	High Similarity	NPC471450
0.9223	High Similarity	NPC471887
0.9135	High Similarity	NPC93352
0.9126	High Similarity	NPC471889
0.9126	High Similarity	NPC37207
0.9115	High Similarity	NPC41129
0.9038	High Similarity	NPC213190
0.9029	High Similarity	NPC21568
0.9029	High Similarity	NPC285231
0.8981	High Similarity	NPC13190
0.8972	High Similarity	NPC472901
0.8962	High Similarity	NPC226642
0.8952	High Similarity	NPC75608
0.8942	High Similarity	NPC471482
0.8942	High Similarity	NPC300399
0.8899	High Similarity	NPC112274
0.8899	High Similarity	NPC475354
0.8879	High Similarity	NPC80210
0.8879	High Similarity	NPC235824
0.8879	High Similarity	NPC38376
0.8868	High Similarity	NPC472899
0.8868	High Similarity	NPC26798
0.8868	High Similarity	NPC472900
0.8868	High Similarity	NPC472898
0.8846	High Similarity	NPC47566
0.8846	High Similarity	NPC4831
0.8846	High Similarity	NPC309425
0.8846	High Similarity	NPC129372
0.8846	High Similarity	NPC160734
0.8846	High Similarity	NPC88000
0.8846	High Similarity	NPC267510
0.8846	High Similarity	NPC472023
0.8835	High Similarity	NPC5358
0.8835	High Similarity	NPC216260
0.8818	High Similarity	NPC51154
0.8807	High Similarity	NPC473021
0.8807	High Similarity	NPC472987
0.8796	High Similarity	NPC285253
0.8796	High Similarity	NPC180459
0.8796	High Similarity	NPC128133
0.8796	High Similarity	NPC221110
0.8796	High Similarity	NPC195116
0.8785	High Similarity	NPC231340
0.8774	High Similarity	NPC475365
0.8774	High Similarity	NPC470885
0.8774	High Similarity	NPC221562
0.8774	High Similarity	NPC187400
0.8762	High Similarity	NPC136816
0.875	High Similarity	NPC100048
0.875	High Similarity	NPC473200
0.875	High Similarity	NPC7341
0.875	High Similarity	NPC20979
0.875	High Similarity	NPC476690
0.8739	High Similarity	NPC11548
0.8704	High Similarity	NPC476539
0.8704	High Similarity	NPC476540
0.8704	High Similarity	NPC472897
0.8704	High Similarity	NPC476541
0.8704	High Similarity	NPC220427
0.8704	High Similarity	NPC476538
0.8704	High Similarity	NPC472896
0.8679	High Similarity	NPC286969
0.8679	High Similarity	NPC131479
0.8679	High Similarity	NPC120123
0.8679	High Similarity	NPC114874
0.8679	High Similarity	NPC31907
0.8679	High Similarity	NPC155010
0.8679	High Similarity	NPC472252
0.8679	High Similarity	NPC473198
0.8679	High Similarity	NPC473124
0.8679	High Similarity	NPC473123
0.8679	High Similarity	NPC157659
0.8679	High Similarity	NPC8039
0.8679	High Similarity	NPC473020
0.8679	High Similarity	NPC245280
0.8679	High Similarity	NPC211879
0.8679	High Similarity	NPC16520
0.8679	High Similarity	NPC189852
0.8673	High Similarity	NPC10366
0.8667	High Similarity	NPC470434
0.8661	High Similarity	NPC477029
0.8661	High Similarity	NPC477030
0.8654	High Similarity	NPC234287
0.8654	High Similarity	NPC158088
0.8654	High Similarity	NPC280825
0.8649	High Similarity	NPC469348
0.8649	High Similarity	NPC469347
0.8636	High Similarity	NPC110494
0.8636	High Similarity	NPC197231
0.8636	High Similarity	NPC157474
0.8624	High Similarity	NPC306131
0.8624	High Similarity	NPC477026
0.8624	High Similarity	NPC476835
0.8624	High Similarity	NPC475670
0.8624	High Similarity	NPC70204
0.8624	High Similarity	NPC477027
0.8611	High Similarity	NPC190395
0.8598	High Similarity	NPC473127
0.8598	High Similarity	NPC31430
0.8598	High Similarity	NPC110656
0.8598	High Similarity	NPC203354
0.8598	High Similarity	NPC85593
0.8598	High Similarity	NPC165033
0.8598	High Similarity	NPC273879
0.8596	High Similarity	NPC477071
0.8585	High Similarity	NPC312553
0.8585	High Similarity	NPC22634
0.8585	High Similarity	NPC159036
0.8585	High Similarity	NPC288694
0.8585	High Similarity	NPC272015
0.8584	High Similarity	NPC474418
0.8584	High Similarity	NPC34390
0.8584	High Similarity	NPC196429
0.8584	High Similarity	NPC142066
0.8584	High Similarity	NPC50305
0.8584	High Similarity	NPC471355
0.8584	High Similarity	NPC471353
0.8584	High Similarity	NPC77319
0.8584	High Similarity	NPC471351
0.8584	High Similarity	NPC84987
0.8584	High Similarity	NPC93883
0.8584	High Similarity	NPC471354
0.8584	High Similarity	NPC27507
0.8584	High Similarity	NPC244402
0.8584	High Similarity	NPC243196
0.8584	High Similarity	NPC157376
0.8584	High Similarity	NPC99728
0.8584	High Similarity	NPC158344
0.8584	High Similarity	NPC87250
0.8584	High Similarity	NPC473852
0.8584	High Similarity	NPC309034
0.8584	High Similarity	NPC203862
0.8571	High Similarity	NPC324598
0.8571	High Similarity	NPC469942
0.8559	High Similarity	NPC476305
0.8559	High Similarity	NPC473125
0.8559	High Similarity	NPC42171
0.8559	High Similarity	NPC477050
0.8559	High Similarity	NPC19888
0.8558	High Similarity	NPC240372
0.8558	High Similarity	NPC243728
0.8558	High Similarity	NPC473890
0.8545	High Similarity	NPC472717
0.8545	High Similarity	NPC141433
0.8522	High Similarity	NPC475629
0.8522	High Similarity	NPC475556
0.8519	High Similarity	NPC473476
0.8519	High Similarity	NPC473923
0.8519	High Similarity	NPC269627
0.8519	High Similarity	NPC181845
0.8519	High Similarity	NPC160816
0.8519	High Similarity	NPC194842
0.8519	High Similarity	NPC208477
0.8519	High Similarity	NPC69737
0.8519	High Similarity	NPC242748
0.8519	High Similarity	NPC474015
0.8519	High Similarity	NPC473199
0.8519	High Similarity	NPC152584
0.8519	High Similarity	NPC208594
0.8519	High Similarity	NPC309448
0.8519	High Similarity	NPC127801
0.8509	High Similarity	NPC160888
0.8509	High Similarity	NPC83287
0.8509	High Similarity	NPC475403
0.8509	High Similarity	NPC45475
0.8505	High Similarity	NPC99627
0.8505	High Similarity	NPC16573
0.8505	High Similarity	NPC475701
0.8505	High Similarity	NPC473129
0.8496	Intermediate Similarity	NPC193382
0.8496	Intermediate Similarity	NPC199428
0.8496	Intermediate Similarity	NPC5311
0.8496	Intermediate Similarity	NPC310341
0.8496	Intermediate Similarity	NPC207637
0.8496	Intermediate Similarity	NPC148965
0.8496	Intermediate Similarity	NPC99620
0.8491	Intermediate Similarity	NPC176406
0.8482	Intermediate Similarity	NPC40133
0.8482	Intermediate Similarity	NPC476671
0.8482	Intermediate Similarity	NPC290608
0.8482	Intermediate Similarity	NPC473128
0.8482	Intermediate Similarity	NPC49413

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 NPC231797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1529
0.2-0.3	4149
0.3-0.4	2179
0.4-0.5	641
0.5-0.6	277
0.6-0.7	114
0.7-0.8	26
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8509	High Similarity	NPD7327	Approved
0.8509	High Similarity	NPD7328	Approved
0.8448	Intermediate Similarity	NPD8379	Approved
0.8448	Intermediate Similarity	NPD8296	Approved
0.8448	Intermediate Similarity	NPD8378	Approved
0.8448	Intermediate Similarity	NPD8335	Approved
0.8448	Intermediate Similarity	NPD7503	Approved
0.8448	Intermediate Similarity	NPD8380	Approved
0.8435	Intermediate Similarity	NPD7516	Approved
0.8362	Intermediate Similarity	NPD8377	Approved
0.8362	Intermediate Similarity	NPD8294	Approved
0.8291	Intermediate Similarity	NPD8033	Approved
0.7869	Intermediate Similarity	NPD7507	Approved
0.7823	Intermediate Similarity	NPD7319	Approved
0.7542	Intermediate Similarity	NPD8133	Approved
0.7478	Intermediate Similarity	NPD6412	Phase 2
0.7414	Intermediate Similarity	NPD6686	Approved
0.7398	Intermediate Similarity	NPD8517	Approved
0.7398	Intermediate Similarity	NPD8515	Approved
0.7398	Intermediate Similarity	NPD8513	Phase 3
0.7398	Intermediate Similarity	NPD8516	Approved
0.7358	Intermediate Similarity	NPD7524	Approved
0.7339	Intermediate Similarity	NPD8171	Discontinued
0.7339	Intermediate Similarity	NPD6370	Approved
0.7323	Intermediate Similarity	NPD7736	Approved
0.7238	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD6695	Phase 3
0.7109	Intermediate Similarity	NPD8293	Discontinued
0.704	Intermediate Similarity	NPD6059	Approved
0.7037	Intermediate Similarity	NPD7750	Discontinued
0.7019	Intermediate Similarity	NPD7525	Registered
0.7018	Intermediate Similarity	NPD7638	Approved
0.6984	Remote Similarity	NPD6015	Approved
0.6984	Remote Similarity	NPD6016	Approved
0.697	Remote Similarity	NPD8449	Approved
0.6957	Remote Similarity	NPD7639	Approved
0.6957	Remote Similarity	NPD7640	Approved
0.6953	Remote Similarity	NPD7492	Approved
0.6935	Remote Similarity	NPD7115	Discovery
0.6929	Remote Similarity	NPD5988	Approved
0.6917	Remote Similarity	NPD8450	Suspended
0.6899	Remote Similarity	NPD6616	Approved
0.6875	Remote Similarity	NPD8328	Phase 3
0.6857	Remote Similarity	NPD6930	Phase 2
0.6857	Remote Similarity	NPD7514	Phase 3
0.6857	Remote Similarity	NPD6931	Approved
0.6846	Remote Similarity	NPD7078	Approved
0.68	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6929	Approved
0.6748	Remote Similarity	NPD6882	Approved
0.6748	Remote Similarity	NPD8297	Approved
0.6744	Remote Similarity	NPD6067	Discontinued
0.6731	Remote Similarity	NPD6932	Approved
0.6723	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD8074	Phase 3
0.6698	Remote Similarity	NPD6928	Phase 2
0.6698	Remote Similarity	NPD7332	Phase 2
0.669	Remote Similarity	NPD7625	Phase 1
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6009	Approved
0.6641	Remote Similarity	NPD6319	Approved
0.6637	Remote Similarity	NPD7637	Suspended
0.6637	Remote Similarity	NPD7087	Discontinued
0.6636	Remote Similarity	NPD6902	Approved
0.6635	Remote Similarity	NPD6933	Approved
0.661	Remote Similarity	NPD5344	Discontinued
0.661	Remote Similarity	NPD4159	Approved
0.6604	Remote Similarity	NPD7645	Phase 2
0.6585	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4225	Approved
0.6577	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5776	Phase 2
0.6571	Remote Similarity	NPD6925	Approved
0.656	Remote Similarity	NPD4632	Approved
0.6557	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6893	Approved
0.6541	Remote Similarity	NPD6033	Approved
0.6538	Remote Similarity	NPD7339	Approved
0.6538	Remote Similarity	NPD6942	Approved
0.6525	Remote Similarity	NPD6648	Approved
0.646	Remote Similarity	NPD6051	Approved
0.6449	Remote Similarity	NPD6683	Phase 2
0.6442	Remote Similarity	NPD6926	Approved
0.6442	Remote Similarity	NPD6924	Approved
0.6423	Remote Similarity	NPD7320	Approved
0.6423	Remote Similarity	NPD6881	Approved
0.6423	Remote Similarity	NPD6899	Approved
0.6417	Remote Similarity	NPD7632	Discontinued
0.6412	Remote Similarity	NPD5126	Approved
0.6412	Remote Similarity	NPD5125	Phase 3
0.6404	Remote Similarity	NPD7838	Discovery
0.64	Remote Similarity	NPD6649	Approved
0.64	Remote Similarity	NPD8130	Phase 1
0.64	Remote Similarity	NPD6650	Approved
0.6393	Remote Similarity	NPD6402	Approved
0.6393	Remote Similarity	NPD6640	Phase 3
0.6393	Remote Similarity	NPD5739	Approved
0.6393	Remote Similarity	NPD6675	Approved
0.6393	Remote Similarity	NPD7128	Approved
0.6385	Remote Similarity	NPD7741	Discontinued
0.6371	Remote Similarity	NPD6373	Approved
0.6371	Remote Similarity	NPD6372	Approved
0.6341	Remote Similarity	NPD5697	Approved
0.6341	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6898	Phase 1
0.6321	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7290	Approved
0.632	Remote Similarity	NPD4634	Approved
0.632	Remote Similarity	NPD6883	Approved
0.632	Remote Similarity	NPD7102	Approved
0.6293	Remote Similarity	NPD6399	Phase 3
0.6281	Remote Similarity	NPD5211	Phase 2
0.627	Remote Similarity	NPD6617	Approved
0.627	Remote Similarity	NPD6847	Approved
0.627	Remote Similarity	NPD6869	Approved
0.626	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD7799	Discontinued
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD7152	Approved
0.625	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD7150	Approved
0.625	Remote Similarity	NPD7151	Approved
0.6241	Remote Similarity	NPD7604	Phase 2
0.624	Remote Similarity	NPD6012	Approved
0.624	Remote Similarity	NPD6014	Approved
0.624	Remote Similarity	NPD6013	Approved
0.6239	Remote Similarity	NPD7509	Discontinued
0.6226	Remote Similarity	NPD8264	Approved
0.622	Remote Similarity	NPD6053	Discontinued
0.6218	Remote Similarity	NPD4755	Approved
0.6212	Remote Similarity	NPD5983	Phase 2
0.621	Remote Similarity	NPD5701	Approved
0.6207	Remote Similarity	NPD6079	Approved
0.6207	Remote Similarity	NPD8035	Phase 2
0.6207	Remote Similarity	NPD8034	Phase 2
0.6204	Remote Similarity	NPD5956	Approved
0.6204	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5141	Approved
0.6174	Remote Similarity	NPD5328	Approved
0.6161	Remote Similarity	NPD4786	Approved
0.616	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD4202	Approved
0.6154	Remote Similarity	NPD7143	Approved
0.6154	Remote Similarity	NPD7144	Approved
0.6148	Remote Similarity	NPD5225	Approved
0.6148	Remote Similarity	NPD5226	Approved
0.6148	Remote Similarity	NPD4633	Approved
0.6148	Remote Similarity	NPD5224	Approved
0.6148	Remote Similarity	NPD6336	Discontinued
0.6132	Remote Similarity	NPD4784	Approved
0.6132	Remote Similarity	NPD4785	Approved
0.6121	Remote Similarity	NPD3168	Discontinued
0.6116	Remote Similarity	NPD4700	Approved
0.6102	Remote Similarity	NPD7748	Approved
0.6098	Remote Similarity	NPD5174	Approved
0.6098	Remote Similarity	NPD5175	Approved
0.6095	Remote Similarity	NPD4243	Approved
0.609	Remote Similarity	NPD6921	Approved
0.6083	Remote Similarity	NPD6084	Phase 2
0.6083	Remote Similarity	NPD6083	Phase 2
0.6083	Remote Similarity	NPD7902	Approved
0.6066	Remote Similarity	NPD5223	Approved
0.6058	Remote Similarity	NPD6922	Approved
0.6058	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6923	Approved
0.6053	Remote Similarity	NPD3618	Phase 1
0.605	Remote Similarity	NPD7991	Discontinued
0.6043	Remote Similarity	NPD7260	Phase 2
0.6032	Remote Similarity	NPD4729	Approved
0.6032	Remote Similarity	NPD4730	Approved
0.6018	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD5221	Approved
0.5983	Remote Similarity	NPD46	Approved
0.5983	Remote Similarity	NPD6698	Approved
0.5983	Remote Similarity	NPD7136	Phase 2
0.5982	Remote Similarity	NPD3667	Approved
0.5981	Remote Similarity	NPD1811	Approved
0.5981	Remote Similarity	NPD1810	Approved
0.5965	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.595	Remote Similarity	NPD5173	Approved
0.5946	Remote Similarity	NPD6674	Discontinued
0.5946	Remote Similarity	NPD4748	Discontinued
0.594	Remote Similarity	NPD7100	Approved
0.594	Remote Similarity	NPD7101	Approved
0.5938	Remote Similarity	NPD5247	Approved
0.5938	Remote Similarity	NPD5251	Approved
0.5938	Remote Similarity	NPD5249	Phase 3
0.5938	Remote Similarity	NPD5248	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