NPASS Compound

Structure

NPC191439 OpenBabel07101718192D 47 52 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 3.5709 6.3985 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 -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 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 -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 3.9310 4.7043 0.0000 C 0 0 1 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 2 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 3.2619 5.4474 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 1 0 0 0 0 2 21 1 0 0 0 0 4 34 1 0 0 0 0 5 34 1 0 0 0 0 6 35 1 0 0 0 0 8 43 1 0 0 0 0 9 44 1 0 0 0 0 10 11 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 15 2 0 0 0 0 13 26 1 0 0 0 0 14 36 1 0 0 0 0 16 17 1 0 0 0 0 16 35 1 0 0 0 0 18 21 2 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 39 1 0 0 0 0 22 3 1 1 0 0 0 22 24 1 0 0 0 0 23 18 1 1 0 0 0 23 43 1 0 0 0 0 24 35 1 1 0 0 0 25 20 1 6 0 0 0 25 29 1 0 0 0 0 25 45 1 0 0 0 0 26 36 1 6 0 0 0 26 37 1 0 0 0 0 27 37 1 1 0 0 0 27 38 1 0 0 0 0 28 34 1 0 0 0 0 28 46 1 1 0 0 0 29 30 1 0 0 0 0 29 40 1 1 0 0 0 30 31 1 0 0 0 0 30 41 1 1 0 0 0 31 32 1 0 0 0 0 31 42 1 1 0 0 0 32 45 1 0 0 0 0 32 46 1 6 0 0 0 33 37 1 1 0 0 0 33 44 1 0 0 0 0 33 47 1 0 0 0 0 34 38 1 0 0 0 0 35 36 1 1 0 0 0 36 7 1 6 0 0 0 37 17 1 6 0 0 0 38 15 1 1 0 0 0 38 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	662.44
Volume:	688.304
LogP:	5.389
LogD:	4.349
LogS:	-5.046
# Rotatable Bonds:	9
TPSA:	127.07
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.259
Synthetic Accessibility Score:	7.125
Fsp3:	0.895
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:	-5.159
MDCK Permeability:	2.1150550310267136e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.598
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	84.33565521240234%
Volume Distribution (VD):	0.816
Pgp-substrate:	5.707756519317627%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.432
CYP3A4-substrate:	0.56

ADMET: Excretion

Clearance (CL):	1.759
Half-life (T1/2):	0.381

ADMET: Toxicity

hERG Blockers:	0.563
Human Hepatotoxicity (H-HT):	0.464
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.284
Maximum Recommended Daily Dose:	0.059
Skin Sensitization:	0.417
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC191439

Natural Product ID:	NPC191439
*Common Name:**	Charantoside Ii
IUPAC Name:	n.a.
Synonyms:	charantoside II
Standard InCHIKey:	YDOSNHSZOCLBFE-HGJRUNHKSA-N
Standard InCHI:	InChI=1S/C38H62O9/c1-21(2)18-23(43-8)19-22(3)24-12-14-36(7)26-13-15-38-27(37(26,33(44-9)47-38)17-16-35(24,36)6)10-11-28(34(38,4)5)46-32-31(42)30(41)29(40)25(20-39)45-32/h13,15,18,22-33,39-42H,10-12,14,16-17,19-20H2,1-9H3/t22-,23+,24-,25-,26+,27+,28+,29-,30-,31-,32+,33-,35-,36+,37+,38-/m1/s1
SMILES:	CO[C@H](C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2C=C[C@]2([C@H]3CC[C@@H](C2(C)C)O[C@@H]2O[C@H](CO)[C@H]([C@H]([C@H]2O)O)O)O[C@H]1OC)C)C)C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255021
PubChem CID:	23626168
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

*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[452863]
NPT2	Others	Unspecified		Inhibition	=	12.3	%	PMID[452863]
NPT2	Others	Unspecified		Inhibition	=	35.0	%	PMID[452863]
NPT2	Others	Unspecified		Inhibition	=	82.1	%	PMID[452863]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[452863]

☑ 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 NPC191439 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	270
0.1-0.2	1703
0.2-0.3	5238
0.3-0.4	12048
0.4-0.5	10033
0.5-0.6	6461
0.6-0.7	4313
0.7-0.8	2034
0.8-0.85	469
0.85-0.9	97
0.9-0.95	21
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC103627
1.0	High Similarity	NPC170974
0.9901	High Similarity	NPC473328
0.9901	High Similarity	NPC473318
0.9901	High Similarity	NPC28844
0.9806	High Similarity	NPC231797
0.9804	High Similarity	NPC65155
0.9709	High Similarity	NPC208189
0.9709	High Similarity	NPC65034
0.9515	High Similarity	NPC250089
0.9515	High Similarity	NPC157530
0.9515	High Similarity	NPC14630
0.951	High Similarity	NPC33053
0.9429	High Similarity	NPC473567
0.9429	High Similarity	NPC216595
0.9406	High Similarity	NPC471885
0.9406	High Similarity	NPC471888
0.9406	High Similarity	NPC471886
0.9406	High Similarity	NPC471887
0.9314	High Similarity	NPC93352
0.9307	High Similarity	NPC37207
0.9216	High Similarity	NPC213190
0.9208	High Similarity	NPC285231
0.9208	High Similarity	NPC21568
0.9151	High Similarity	NPC13190
0.9143	High Similarity	NPC472901
0.9135	High Similarity	NPC226642
0.9126	High Similarity	NPC75608
0.9118	High Similarity	NPC300399
0.9118	High Similarity	NPC471482
0.9065	High Similarity	NPC475354
0.9065	High Similarity	NPC112274
0.9048	High Similarity	NPC80210
0.9048	High Similarity	NPC38376
0.9048	High Similarity	NPC235824
0.9038	High Similarity	NPC26798
0.9038	High Similarity	NPC472900
0.9038	High Similarity	NPC472898
0.9038	High Similarity	NPC472899
0.9029	High Similarity	NPC471450
0.902	High Similarity	NPC472023
0.902	High Similarity	NPC4831
0.902	High Similarity	NPC309425
0.902	High Similarity	NPC160734
0.902	High Similarity	NPC129372
0.902	High Similarity	NPC88000
0.902	High Similarity	NPC47566
0.901	High Similarity	NPC216260
0.901	High Similarity	NPC5358
0.8981	High Similarity	NPC51154
0.8972	High Similarity	NPC472987
0.8972	High Similarity	NPC473021
0.8962	High Similarity	NPC195116
0.8962	High Similarity	NPC285253
0.8962	High Similarity	NPC180459
0.8962	High Similarity	NPC221110
0.8962	High Similarity	NPC128133
0.8952	High Similarity	NPC231340
0.8942	High Similarity	NPC187400
0.8942	High Similarity	NPC221562
0.8942	High Similarity	NPC470885
0.8942	High Similarity	NPC475365
0.8938	High Similarity	NPC41129
0.8932	High Similarity	NPC471889
0.8932	High Similarity	NPC136816
0.8922	High Similarity	NPC7341
0.8922	High Similarity	NPC473200
0.8909	High Similarity	NPC100048
0.8909	High Similarity	NPC20979
0.8909	High Similarity	NPC476690
0.8899	High Similarity	NPC11548
0.8868	High Similarity	NPC476538
0.8868	High Similarity	NPC476540
0.8868	High Similarity	NPC476539
0.8868	High Similarity	NPC476541
0.8868	High Similarity	NPC472896
0.8868	High Similarity	NPC472897
0.8868	High Similarity	NPC220427
0.8846	High Similarity	NPC473123
0.8846	High Similarity	NPC120123
0.8846	High Similarity	NPC473020
0.8846	High Similarity	NPC131479
0.8846	High Similarity	NPC16520
0.8846	High Similarity	NPC473124
0.8846	High Similarity	NPC157659
0.8846	High Similarity	NPC8039
0.8846	High Similarity	NPC473198
0.8846	High Similarity	NPC211879
0.8846	High Similarity	NPC31907
0.8846	High Similarity	NPC472252
0.8846	High Similarity	NPC189852
0.8846	High Similarity	NPC245280
0.8846	High Similarity	NPC286969
0.8846	High Similarity	NPC114874
0.8846	High Similarity	NPC155010
0.8835	High Similarity	NPC470434
0.8829	High Similarity	NPC10366
0.8824	High Similarity	NPC280825
0.8824	High Similarity	NPC158088
0.8824	High Similarity	NPC234287
0.8818	High Similarity	NPC477030
0.8818	High Similarity	NPC477029
0.8807	High Similarity	NPC469348
0.8807	High Similarity	NPC469347
0.8796	High Similarity	NPC157474
0.8796	High Similarity	NPC110494
0.8796	High Similarity	NPC197231
0.8785	High Similarity	NPC477027
0.8785	High Similarity	NPC477026
0.8785	High Similarity	NPC476835
0.8785	High Similarity	NPC475670
0.8785	High Similarity	NPC306131
0.8785	High Similarity	NPC70204
0.8774	High Similarity	NPC190395
0.8762	High Similarity	NPC273879
0.8762	High Similarity	NPC85593
0.8762	High Similarity	NPC203354
0.8762	High Similarity	NPC165033
0.8762	High Similarity	NPC473127
0.8762	High Similarity	NPC31430
0.8762	High Similarity	NPC110656
0.875	High Similarity	NPC477071
0.875	High Similarity	NPC288694
0.875	High Similarity	NPC272015
0.875	High Similarity	NPC312553
0.875	High Similarity	NPC159036
0.8739	High Similarity	NPC34390
0.8739	High Similarity	NPC196429
0.8739	High Similarity	NPC77319
0.8739	High Similarity	NPC158344
0.8739	High Similarity	NPC471351
0.8739	High Similarity	NPC471353
0.8739	High Similarity	NPC87250
0.8739	High Similarity	NPC309034
0.8739	High Similarity	NPC471354
0.8739	High Similarity	NPC244402
0.8739	High Similarity	NPC471355
0.8739	High Similarity	NPC93883
0.8739	High Similarity	NPC157376
0.8739	High Similarity	NPC84987
0.8739	High Similarity	NPC99728
0.8739	High Similarity	NPC50305
0.8739	High Similarity	NPC474418
0.8739	High Similarity	NPC473852
0.8739	High Similarity	NPC243196
0.8739	High Similarity	NPC203862
0.8739	High Similarity	NPC27507
0.8739	High Similarity	NPC142066
0.8738	High Similarity	NPC324598
0.8738	High Similarity	NPC469942
0.8725	High Similarity	NPC243728
0.8725	High Similarity	NPC473890
0.8725	High Similarity	NPC240372
0.8716	High Similarity	NPC476305
0.8716	High Similarity	NPC42171
0.8716	High Similarity	NPC19888
0.8716	High Similarity	NPC473125
0.8716	High Similarity	NPC477050
0.8704	High Similarity	NPC141433
0.8704	High Similarity	NPC472717
0.8679	High Similarity	NPC69737
0.8679	High Similarity	NPC473923
0.8679	High Similarity	NPC473476
0.8679	High Similarity	NPC269627
0.8679	High Similarity	NPC181845
0.8679	High Similarity	NPC473199
0.8679	High Similarity	NPC242748
0.8679	High Similarity	NPC160816
0.8679	High Similarity	NPC152584
0.8679	High Similarity	NPC208477
0.8679	High Similarity	NPC127801
0.8679	High Similarity	NPC474015
0.8679	High Similarity	NPC208594
0.8679	High Similarity	NPC194842
0.8679	High Similarity	NPC309448
0.8673	High Similarity	NPC475629
0.8673	High Similarity	NPC475556
0.8667	High Similarity	NPC16573
0.8667	High Similarity	NPC475701
0.8661	High Similarity	NPC83287
0.8661	High Similarity	NPC45475
0.8661	High Similarity	NPC475403
0.8661	High Similarity	NPC160888
0.8654	High Similarity	NPC267510
0.8654	High Similarity	NPC176406
0.8649	High Similarity	NPC199428
0.8649	High Similarity	NPC99620
0.8649	High Similarity	NPC148965
0.8649	High Similarity	NPC193382
0.8649	High Similarity	NPC207637
0.8649	High Similarity	NPC5311
0.8649	High Similarity	NPC310341
0.8636	High Similarity	NPC44298
0.8636	High Similarity	NPC40133
0.8636	High Similarity	NPC290608
0.8636	High Similarity	NPC473128
0.8636	High Similarity	NPC476671
0.8636	High Similarity	NPC49413
0.8627	High Similarity	NPC98457
0.8627	High Similarity	NPC227583

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 NPC191439 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	1794
0.2-0.3	4178
0.3-0.4	1987
0.4-0.5	543
0.5-0.6	268
0.6-0.7	125
0.7-0.8	25
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8661	High Similarity	NPD7328	Approved
0.8661	High Similarity	NPD7327	Approved
0.8596	High Similarity	NPD8380	Approved
0.8596	High Similarity	NPD8378	Approved
0.8596	High Similarity	NPD8379	Approved
0.8596	High Similarity	NPD8335	Approved
0.8596	High Similarity	NPD8296	Approved
0.8584	High Similarity	NPD7516	Approved
0.8509	High Similarity	NPD8294	Approved
0.8509	High Similarity	NPD8377	Approved
0.8435	Intermediate Similarity	NPD8033	Approved
0.8276	Intermediate Similarity	NPD7503	Approved
0.8	Intermediate Similarity	NPD7507	Approved
0.7951	Intermediate Similarity	NPD7319	Approved
0.7672	Intermediate Similarity	NPD8133	Approved
0.7611	Intermediate Similarity	NPD6412	Phase 2
0.7544	Intermediate Similarity	NPD6686	Approved
0.7477	Intermediate Similarity	NPD8171	Discontinued
0.7459	Intermediate Similarity	NPD6370	Approved
0.744	Intermediate Similarity	NPD7736	Approved
0.7328	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6054	Approved
0.7236	Intermediate Similarity	NPD8515	Approved
0.7236	Intermediate Similarity	NPD8513	Phase 3
0.7236	Intermediate Similarity	NPD8517	Approved
0.7236	Intermediate Similarity	NPD8516	Approved
0.7222	Intermediate Similarity	NPD8293	Discontinued
0.717	Intermediate Similarity	NPD7524	Approved
0.7157	Intermediate Similarity	NPD7525	Registered
0.7154	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7097	Intermediate Similarity	NPD6015	Approved
0.7097	Intermediate Similarity	NPD6016	Approved
0.708	Intermediate Similarity	NPD7639	Approved
0.708	Intermediate Similarity	NPD7640	Approved
0.7077	Intermediate Similarity	NPD8449	Approved
0.7063	Intermediate Similarity	NPD7492	Approved
0.7049	Intermediate Similarity	NPD7115	Discovery
0.7048	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5988	Approved
0.7023	Intermediate Similarity	NPD8450	Suspended
0.7008	Intermediate Similarity	NPD6616	Approved
0.6984	Remote Similarity	NPD8328	Phase 3
0.6953	Remote Similarity	NPD7078	Approved
0.6952	Remote Similarity	NPD6695	Phase 3
0.6911	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8297	Approved
0.686	Remote Similarity	NPD6882	Approved
0.6852	Remote Similarity	NPD7750	Discontinued
0.685	Remote Similarity	NPD6067	Discontinued
0.6838	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6928	Phase 2
0.6786	Remote Similarity	NPD7625	Phase 1
0.6777	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6009	Approved
0.6746	Remote Similarity	NPD6319	Approved
0.6731	Remote Similarity	NPD7645	Phase 2
0.6724	Remote Similarity	NPD4159	Approved
0.6724	Remote Similarity	NPD5344	Discontinued
0.6697	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4225	Approved
0.6694	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6641	Remote Similarity	NPD6033	Approved
0.6577	Remote Similarity	NPD6051	Approved
0.6571	Remote Similarity	NPD6929	Approved
0.6565	Remote Similarity	NPD8074	Phase 3
0.6538	Remote Similarity	NPD6932	Approved
0.6529	Remote Similarity	NPD6899	Approved
0.6529	Remote Similarity	NPD7320	Approved
0.6529	Remote Similarity	NPD6881	Approved
0.6525	Remote Similarity	NPD7632	Discontinued
0.6509	Remote Similarity	NPD7332	Phase 2
0.6504	Remote Similarity	NPD6649	Approved
0.6504	Remote Similarity	NPD6650	Approved
0.6504	Remote Similarity	NPD8130	Phase 1
0.65	Remote Similarity	NPD6675	Approved
0.65	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD7128	Approved
0.6476	Remote Similarity	NPD7145	Approved
0.6475	Remote Similarity	NPD6372	Approved
0.6475	Remote Similarity	NPD6373	Approved
0.646	Remote Similarity	NPD7637	Suspended
0.646	Remote Similarity	NPD7087	Discontinued
0.6449	Remote Similarity	NPD6902	Approved
0.6446	Remote Similarity	NPD5697	Approved
0.6446	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6933	Approved
0.6442	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD4634	Approved
0.6423	Remote Similarity	NPD6883	Approved
0.6423	Remote Similarity	NPD7290	Approved
0.6423	Remote Similarity	NPD7102	Approved
0.641	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6399	Phase 3
0.6387	Remote Similarity	NPD5211	Phase 2
0.6381	Remote Similarity	NPD5776	Phase 2
0.6381	Remote Similarity	NPD6925	Approved
0.6371	Remote Similarity	NPD6869	Approved
0.6371	Remote Similarity	NPD6847	Approved
0.6371	Remote Similarity	NPD6617	Approved
0.6364	Remote Similarity	NPD6893	Approved
0.6364	Remote Similarity	NPD6008	Approved
0.6356	Remote Similarity	NPD5286	Approved
0.6356	Remote Similarity	NPD6648	Approved
0.6356	Remote Similarity	NPD5285	Approved
0.6356	Remote Similarity	NPD4696	Approved
0.6341	Remote Similarity	NPD6014	Approved
0.6341	Remote Similarity	NPD6013	Approved
0.6341	Remote Similarity	NPD6012	Approved
0.6336	Remote Similarity	NPD7604	Phase 2
0.6325	Remote Similarity	NPD4755	Approved
0.632	Remote Similarity	NPD6053	Discontinued
0.6316	Remote Similarity	NPD8034	Phase 2
0.6316	Remote Similarity	NPD6079	Approved
0.6316	Remote Similarity	NPD8035	Phase 2
0.6311	Remote Similarity	NPD5701	Approved
0.6308	Remote Similarity	NPD5983	Phase 2
0.6296	Remote Similarity	NPD5956	Approved
0.6283	Remote Similarity	NPD5328	Approved
0.6281	Remote Similarity	NPD5141	Approved
0.6273	Remote Similarity	NPD4786	Approved
0.6262	Remote Similarity	NPD6683	Phase 2
0.6261	Remote Similarity	NPD4202	Approved
0.626	Remote Similarity	NPD6011	Approved
0.626	Remote Similarity	NPD5126	Approved
0.626	Remote Similarity	NPD5125	Phase 3
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD4785	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD4784	Approved
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD6924	Approved
0.625	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD6926	Approved
0.6241	Remote Similarity	NPD6336	Discontinued
0.6231	Remote Similarity	NPD7741	Discontinued
0.623	Remote Similarity	NPD6640	Phase 3
0.6228	Remote Similarity	NPD3168	Discontinued
0.6228	Remote Similarity	NPD7838	Discovery
0.6218	Remote Similarity	NPD4700	Approved
0.6214	Remote Similarity	NPD4243	Approved
0.6207	Remote Similarity	NPD7748	Approved
0.6198	Remote Similarity	NPD5174	Approved
0.6198	Remote Similarity	NPD5175	Approved
0.6186	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD6084	Phase 2
0.6186	Remote Similarity	NPD7902	Approved
0.6183	Remote Similarity	NPD6921	Approved
0.6176	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD5223	Approved
0.6161	Remote Similarity	NPD3618	Phase 1
0.6154	Remote Similarity	NPD7991	Discontinued
0.6147	Remote Similarity	NPD6898	Phase 1
0.6129	Remote Similarity	NPD4729	Approved
0.6129	Remote Similarity	NPD4730	Approved
0.6126	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD7799	Discontinued
0.6111	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5222	Approved
0.6102	Remote Similarity	NPD5221	Approved
0.6098	Remote Similarity	NPD4767	Approved
0.6098	Remote Similarity	NPD4768	Approved
0.6095	Remote Similarity	NPD1811	Approved
0.6095	Remote Similarity	NPD1810	Approved
0.6091	Remote Similarity	NPD3667	Approved
0.6087	Remote Similarity	NPD46	Approved
0.6087	Remote Similarity	NPD6698	Approved
0.6071	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7151	Approved
0.6058	Remote Similarity	NPD7152	Approved
0.6058	Remote Similarity	NPD7150	Approved
0.6055	Remote Similarity	NPD7509	Discontinued
0.6055	Remote Similarity	NPD4748	Discontinued
0.605	Remote Similarity	NPD5173	Approved
0.6048	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD8264	Approved
0.6034	Remote Similarity	NPD7515	Phase 2
0.6032	Remote Similarity	NPD5247	Approved
0.6032	Remote Similarity	NPD5251	Approved
0.6032	Remote Similarity	NPD5248	Approved
0.6032	Remote Similarity	NPD5250	Approved
0.6032	Remote Similarity	NPD5249	Phase 3
0.6031	Remote Similarity	NPD7100	Approved
0.6031	Remote Similarity	NPD7101	Approved
0.6019	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4753	Phase 2
0.5971	Remote Similarity	NPD8338	Approved
0.5966	Remote Similarity	NPD4697	Phase 3
0.5963	Remote Similarity	NPD4195	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