NPASS Compound

Structure

NPC473318 OpenBabel07101718302D 47 52 0 0 1 0 0 0 0 0999 V2000 5.2693 3.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0103 6.8414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2672 6.1723 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 6.5054 7.0222 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 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 4.9092 4.9122 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 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 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 3 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 -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 6.1964 6.0712 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 2 33 1 0 0 0 0 3 33 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 16 2 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 17 1 0 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 15 25 1 0 0 0 0 16 33 1 0 0 0 0 17 36 1 0 0 0 0 19 20 1 0 0 0 0 19 35 1 0 0 0 0 21 39 1 0 0 0 0 22 1 1 1 0 0 0 22 23 1 0 0 0 0 23 35 1 1 0 0 0 24 21 1 6 0 0 0 24 28 1 0 0 0 0 24 45 1 0 0 0 0 25 36 1 6 0 0 0 25 37 1 0 0 0 0 26 37 1 1 0 0 0 26 38 1 0 0 0 0 27 34 1 0 0 0 0 27 46 1 1 0 0 0 28 29 1 0 0 0 0 28 40 1 1 0 0 0 29 30 1 0 0 0 0 29 41 1 1 0 0 0 30 31 1 0 0 0 0 30 42 1 1 0 0 0 31 45 1 0 0 0 0 31 46 1 6 0 0 0 32 37 1 0 0 0 0 32 43 1 0 0 0 0 32 47 1 0 0 0 0 33 44 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 20 1 6 0 0 0 38 18 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:	5.119
LogD:	4.253
LogS:	-5.047
# 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:	7.108
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:	-4.933
MDCK Permeability:	2.795458749460522e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.232
Human Intestinal Absorption (HIA):	0.091
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.514

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	95.09984588623047%
Volume Distribution (VD):	0.795
Pgp-substrate:	5.907383918762207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.513
CYP3A4-substrate:	0.457

ADMET: Excretion

Clearance (CL):	1.928
Half-life (T1/2):	0.393

ADMET: Toxicity

hERG Blockers:	0.253
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.306
Skin Sensitization:	0.574
Carcinogencity:	0.121
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC473318

Natural Product ID:	NPC473318
*Common Name:**	Goyaglycoside D
IUPAC Name:	n.a.
Synonyms:	Goyaglycoside D
Standard InCHIKey:	JYKQEJLWLRMCRC-MTTTWNDTSA-N
Standard InCHI:	InChI=1S/C38H62O9/c1-22(11-10-16-33(2,3)44-9)23-14-17-36(7)25-15-18-38-26(37(25,32(43-8)47-38)20-19-35(23,36)6)12-13-27(34(38,4)5)46-31-30(42)29(41)28(40)24(21-39)45-31/h10,15-16,18,22-32,39-42H,11-14,17,19-21H2,1-9H3/b16-10+/t22-,23-,24-,25+,26+,27+,28-,29-,30-,31+,32?,35-,36+,37+,38-/m1/s1
SMILES:	COC1O[C@@]23[C@H]([C@]41CC[C@]1([C@@]([C@@H]4C=C2)(C)CC[C@@H]1[C@@H](C/C=C/C(OC)(C)C)C)C)CC[C@@H](C3(C)C)O[C@@H]1O[C@H](CO)[C@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399972
PubChem CID:	44445564
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[515128]
NPT2	Others	Unspecified		Inhibition	=	11.2	%	PMID[515128]
NPT2	Others	Unspecified		Inhibition	=	34.2	%	PMID[515128]
NPT2	Others	Unspecified		Inhibition	=	80.3	%	PMID[515128]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[515128]

☑ 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 NPC473318 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	263
0.1-0.2	1797
0.2-0.3	5431
0.3-0.4	12372
0.4-0.5	9890
0.5-0.6	6404
0.6-0.7	4050
0.7-0.8	1947
0.8-0.85	436
0.85-0.9	79
0.9-0.95	18
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473328
1.0	High Similarity	NPC28844
0.9901	High Similarity	NPC170974
0.9901	High Similarity	NPC65155
0.9901	High Similarity	NPC103627
0.9901	High Similarity	NPC191439
0.9709	High Similarity	NPC231797
0.9612	High Similarity	NPC208189
0.9612	High Similarity	NPC65034
0.9417	High Similarity	NPC250089
0.9417	High Similarity	NPC14630
0.9417	High Similarity	NPC157530
0.9412	High Similarity	NPC33053
0.94	High Similarity	NPC37207
0.9333	High Similarity	NPC216595
0.9333	High Similarity	NPC473567
0.9307	High Similarity	NPC471886
0.9307	High Similarity	NPC471888
0.9307	High Similarity	NPC471887
0.9307	High Similarity	NPC471885
0.9216	High Similarity	NPC93352
0.9208	High Similarity	NPC300399
0.9208	High Similarity	NPC471482
0.9151	High Similarity	NPC475354
0.9135	High Similarity	NPC80210
0.9135	High Similarity	NPC38376
0.9135	High Similarity	NPC235824
0.9118	High Similarity	NPC213190
0.9109	High Similarity	NPC285231
0.9109	High Similarity	NPC21568
0.9057	High Similarity	NPC13190
0.9048	High Similarity	NPC195116
0.9048	High Similarity	NPC221110
0.9048	High Similarity	NPC180459
0.9048	High Similarity	NPC285253
0.9048	High Similarity	NPC472901
0.9038	High Similarity	NPC226642
0.9029	High Similarity	NPC75608
0.9029	High Similarity	NPC475365
0.8972	High Similarity	NPC112274
0.8952	High Similarity	NPC472897
0.8952	High Similarity	NPC472896
0.8942	High Similarity	NPC472899
0.8942	High Similarity	NPC26798
0.8942	High Similarity	NPC472900
0.8942	High Similarity	NPC472898
0.8932	High Similarity	NPC471450
0.8922	High Similarity	NPC309425
0.8922	High Similarity	NPC4831
0.8922	High Similarity	NPC472023
0.8922	High Similarity	NPC160734
0.8922	High Similarity	NPC129372
0.8922	High Similarity	NPC47566
0.8922	High Similarity	NPC88000
0.8911	High Similarity	NPC5358
0.8911	High Similarity	NPC216260
0.8889	High Similarity	NPC51154
0.8879	High Similarity	NPC110494
0.8879	High Similarity	NPC157474
0.8879	High Similarity	NPC473021
0.8879	High Similarity	NPC472987
0.8868	High Similarity	NPC128133
0.8857	High Similarity	NPC231340
0.885	High Similarity	NPC41129
0.8846	High Similarity	NPC470885
0.8846	High Similarity	NPC187400
0.8846	High Similarity	NPC221562
0.8835	High Similarity	NPC471889
0.8835	High Similarity	NPC136816
0.8824	High Similarity	NPC473200
0.8824	High Similarity	NPC7341
0.8818	High Similarity	NPC476690
0.8818	High Similarity	NPC100048
0.8818	High Similarity	NPC20979
0.8807	High Similarity	NPC11548
0.8796	High Similarity	NPC476305
0.8796	High Similarity	NPC473125
0.8785	High Similarity	NPC472717
0.8774	High Similarity	NPC476538
0.8774	High Similarity	NPC476540
0.8774	High Similarity	NPC476539
0.8774	High Similarity	NPC220427
0.8774	High Similarity	NPC476541
0.875	High Similarity	NPC131479
0.875	High Similarity	NPC120123
0.875	High Similarity	NPC472252
0.875	High Similarity	NPC114874
0.875	High Similarity	NPC245280
0.875	High Similarity	NPC189852
0.875	High Similarity	NPC473123
0.875	High Similarity	NPC155010
0.875	High Similarity	NPC157659
0.875	High Similarity	NPC211879
0.875	High Similarity	NPC473020
0.875	High Similarity	NPC31907
0.875	High Similarity	NPC473198
0.875	High Similarity	NPC286969
0.875	High Similarity	NPC8039
0.875	High Similarity	NPC16520
0.875	High Similarity	NPC473124
0.8739	High Similarity	NPC10366
0.8738	High Similarity	NPC470434
0.8727	High Similarity	NPC477030
0.8727	High Similarity	NPC477029
0.8725	High Similarity	NPC280825
0.8725	High Similarity	NPC234287
0.8725	High Similarity	NPC158088
0.8716	High Similarity	NPC469348
0.8716	High Similarity	NPC49413
0.8716	High Similarity	NPC44298
0.8716	High Similarity	NPC290608
0.8716	High Similarity	NPC473128
0.8716	High Similarity	NPC469347
0.8716	High Similarity	NPC40133
0.8704	High Similarity	NPC472715
0.8704	High Similarity	NPC197231
0.8692	High Similarity	NPC477026
0.8692	High Similarity	NPC70204
0.8692	High Similarity	NPC477027
0.8692	High Similarity	NPC306131
0.8692	High Similarity	NPC476835
0.8692	High Similarity	NPC475670
0.8679	High Similarity	NPC190395
0.8667	High Similarity	NPC85593
0.8667	High Similarity	NPC203354
0.8667	High Similarity	NPC312774
0.8667	High Similarity	NPC273879
0.8667	High Similarity	NPC31430
0.8667	High Similarity	NPC110656
0.8667	High Similarity	NPC165033
0.8667	High Similarity	NPC473127
0.8661	High Similarity	NPC477071
0.8654	High Similarity	NPC272015
0.8654	High Similarity	NPC288694
0.8654	High Similarity	NPC312553
0.8654	High Similarity	NPC159036
0.8649	High Similarity	NPC471354
0.8649	High Similarity	NPC244402
0.8649	High Similarity	NPC203862
0.8649	High Similarity	NPC34390
0.8649	High Similarity	NPC474418
0.8649	High Similarity	NPC84987
0.8649	High Similarity	NPC142066
0.8649	High Similarity	NPC196429
0.8649	High Similarity	NPC77319
0.8649	High Similarity	NPC471353
0.8649	High Similarity	NPC158344
0.8649	High Similarity	NPC471351
0.8649	High Similarity	NPC157376
0.8649	High Similarity	NPC471355
0.8649	High Similarity	NPC93883
0.8649	High Similarity	NPC473852
0.8649	High Similarity	NPC309034
0.8649	High Similarity	NPC99728
0.8649	High Similarity	NPC243196
0.8649	High Similarity	NPC50305
0.8649	High Similarity	NPC87250
0.8649	High Similarity	NPC27507
0.8641	High Similarity	NPC324598
0.8641	High Similarity	NPC469942
0.8627	High Similarity	NPC243728
0.8627	High Similarity	NPC473890
0.8627	High Similarity	NPC240372
0.8624	High Similarity	NPC477050
0.8624	High Similarity	NPC472716
0.8624	High Similarity	NPC19888
0.8624	High Similarity	NPC42171
0.8611	High Similarity	NPC141433
0.8585	High Similarity	NPC69737
0.8585	High Similarity	NPC208594
0.8585	High Similarity	NPC152584
0.8585	High Similarity	NPC473199
0.8585	High Similarity	NPC473476
0.8585	High Similarity	NPC269627
0.8585	High Similarity	NPC309448
0.8585	High Similarity	NPC181845
0.8585	High Similarity	NPC160816
0.8585	High Similarity	NPC208477
0.8585	High Similarity	NPC127801
0.8585	High Similarity	NPC242748
0.8585	High Similarity	NPC474015
0.8585	High Similarity	NPC194842
0.8585	High Similarity	NPC473923
0.8584	High Similarity	NPC475556
0.8584	High Similarity	NPC475629
0.8571	High Similarity	NPC16573
0.8571	High Similarity	NPC45475
0.8571	High Similarity	NPC160888
0.8571	High Similarity	NPC83287
0.8571	High Similarity	NPC475403
0.8571	High Similarity	NPC475701
0.8559	High Similarity	NPC5311
0.8559	High Similarity	NPC99620
0.8559	High Similarity	NPC199428
0.8559	High Similarity	NPC310341
0.8559	High Similarity	NPC148965
0.8559	High Similarity	NPC207637
0.8559	High Similarity	NPC193382
0.8558	High Similarity	NPC267510
0.8558	High Similarity	NPC176406

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 NPC473318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1935
0.2-0.3	4199
0.3-0.4	1870
0.4-0.5	524
0.5-0.6	267
0.6-0.7	116
0.7-0.8	22
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
0.8571	High Similarity	NPD7328	Approved
0.8571	High Similarity	NPD7327	Approved
0.8509	High Similarity	NPD8378	Approved
0.8509	High Similarity	NPD8380	Approved
0.8509	High Similarity	NPD8379	Approved
0.8509	High Similarity	NPD8296	Approved
0.8509	High Similarity	NPD8335	Approved
0.8496	Intermediate Similarity	NPD7516	Approved
0.8421	Intermediate Similarity	NPD8294	Approved
0.8421	Intermediate Similarity	NPD8377	Approved
0.8348	Intermediate Similarity	NPD8033	Approved
0.819	Intermediate Similarity	NPD7503	Approved
0.7917	Intermediate Similarity	NPD7507	Approved
0.7869	Intermediate Similarity	NPD7319	Approved
0.7586	Intermediate Similarity	NPD8133	Approved
0.7547	Intermediate Similarity	NPD8171	Discontinued
0.7522	Intermediate Similarity	NPD6412	Phase 2
0.7456	Intermediate Similarity	NPD6686	Approved
0.7377	Intermediate Similarity	NPD6370	Approved
0.736	Intermediate Similarity	NPD7736	Approved
0.7241	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6054	Approved
0.7154	Intermediate Similarity	NPD8516	Approved
0.7154	Intermediate Similarity	NPD8517	Approved
0.7154	Intermediate Similarity	NPD8515	Approved
0.7154	Intermediate Similarity	NPD8513	Phase 3
0.7143	Intermediate Similarity	NPD8293	Discontinued
0.7075	Intermediate Similarity	NPD7524	Approved
0.7073	Intermediate Similarity	NPD6059	Approved
0.7059	Intermediate Similarity	NPD7525	Registered
0.7054	Intermediate Similarity	NPD7638	Approved
0.7016	Intermediate Similarity	NPD6016	Approved
0.7016	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD8449	Approved
0.6991	Remote Similarity	NPD7640	Approved
0.6991	Remote Similarity	NPD7639	Approved
0.6984	Remote Similarity	NPD7492	Approved
0.6967	Remote Similarity	NPD7115	Discovery
0.696	Remote Similarity	NPD5988	Approved
0.6952	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8450	Suspended
0.6929	Remote Similarity	NPD6616	Approved
0.6905	Remote Similarity	NPD8328	Phase 3
0.6897	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6928	Phase 2
0.6875	Remote Similarity	NPD7078	Approved
0.6857	Remote Similarity	NPD6695	Phase 3
0.6829	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8297	Approved
0.6777	Remote Similarity	NPD6882	Approved
0.6772	Remote Similarity	NPD6067	Discontinued
0.6759	Remote Similarity	NPD7750	Discontinued
0.6723	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7625	Phase 1
0.6694	Remote Similarity	NPD6009	Approved
0.6694	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6319	Approved
0.6638	Remote Similarity	NPD4159	Approved
0.6638	Remote Similarity	NPD5344	Discontinued
0.6635	Remote Similarity	NPD7645	Phase 2
0.6612	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4225	Approved
0.6606	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4632	Approved
0.6571	Remote Similarity	NPD6930	Phase 2
0.6571	Remote Similarity	NPD7514	Phase 3
0.6571	Remote Similarity	NPD6931	Approved
0.6569	Remote Similarity	NPD6942	Approved
0.6569	Remote Similarity	NPD7339	Approved
0.6565	Remote Similarity	NPD6033	Approved
0.6489	Remote Similarity	NPD8074	Phase 3
0.6486	Remote Similarity	NPD6051	Approved
0.6476	Remote Similarity	NPD6929	Approved
0.6446	Remote Similarity	NPD7320	Approved
0.6446	Remote Similarity	NPD6881	Approved
0.6446	Remote Similarity	NPD6899	Approved
0.6442	Remote Similarity	NPD6932	Approved
0.6441	Remote Similarity	NPD7632	Discontinued
0.6423	Remote Similarity	NPD6649	Approved
0.6423	Remote Similarity	NPD8130	Phase 1
0.6423	Remote Similarity	NPD6650	Approved
0.6417	Remote Similarity	NPD5739	Approved
0.6417	Remote Similarity	NPD6675	Approved
0.6417	Remote Similarity	NPD6402	Approved
0.6417	Remote Similarity	NPD7128	Approved
0.6415	Remote Similarity	NPD7332	Phase 2
0.6393	Remote Similarity	NPD6373	Approved
0.6393	Remote Similarity	NPD6372	Approved
0.6381	Remote Similarity	NPD7145	Approved
0.6372	Remote Similarity	NPD7087	Discontinued
0.6372	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5697	Approved
0.6355	Remote Similarity	NPD6902	Approved
0.6346	Remote Similarity	NPD6933	Approved
0.6346	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7290	Approved
0.6341	Remote Similarity	NPD7102	Approved
0.6341	Remote Similarity	NPD6883	Approved
0.6341	Remote Similarity	NPD4634	Approved
0.6325	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6399	Phase 3
0.6303	Remote Similarity	NPD5211	Phase 2
0.629	Remote Similarity	NPD6847	Approved
0.629	Remote Similarity	NPD6617	Approved
0.629	Remote Similarity	NPD6869	Approved
0.6286	Remote Similarity	NPD5776	Phase 2
0.6286	Remote Similarity	NPD6925	Approved
0.6281	Remote Similarity	NPD6008	Approved
0.6273	Remote Similarity	NPD6893	Approved
0.6271	Remote Similarity	NPD6648	Approved
0.6271	Remote Similarity	NPD5286	Approved
0.6271	Remote Similarity	NPD5285	Approved
0.6271	Remote Similarity	NPD4696	Approved
0.626	Remote Similarity	NPD7604	Phase 2
0.626	Remote Similarity	NPD6012	Approved
0.626	Remote Similarity	NPD6014	Approved
0.626	Remote Similarity	NPD6013	Approved
0.624	Remote Similarity	NPD6053	Discontinued
0.6239	Remote Similarity	NPD4755	Approved
0.6238	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6921	Approved
0.6231	Remote Similarity	NPD5983	Phase 2
0.623	Remote Similarity	NPD5701	Approved
0.6228	Remote Similarity	NPD8035	Phase 2
0.6228	Remote Similarity	NPD8034	Phase 2
0.6228	Remote Similarity	NPD6079	Approved
0.6222	Remote Similarity	NPD5956	Approved
0.6207	Remote Similarity	NPD7991	Discontinued
0.6198	Remote Similarity	NPD5141	Approved
0.6195	Remote Similarity	NPD5328	Approved
0.6183	Remote Similarity	NPD5126	Approved
0.6183	Remote Similarity	NPD5125	Phase 3
0.6182	Remote Similarity	NPD4786	Approved
0.6179	Remote Similarity	NPD6011	Approved
0.6174	Remote Similarity	NPD4202	Approved
0.6168	Remote Similarity	NPD6683	Phase 2
0.6167	Remote Similarity	NPD5226	Approved
0.6167	Remote Similarity	NPD4633	Approved
0.6167	Remote Similarity	NPD5225	Approved
0.6167	Remote Similarity	NPD5224	Approved
0.6165	Remote Similarity	NPD6336	Discontinued
0.6154	Remote Similarity	NPD6924	Approved
0.6154	Remote Similarity	NPD6926	Approved
0.6154	Remote Similarity	NPD4784	Approved
0.6154	Remote Similarity	NPD7741	Discontinued
0.6154	Remote Similarity	NPD1810	Approved
0.6154	Remote Similarity	NPD4785	Approved
0.6154	Remote Similarity	NPD1811	Approved
0.6148	Remote Similarity	NPD6640	Phase 3
0.614	Remote Similarity	NPD3168	Discontinued
0.614	Remote Similarity	NPD7838	Discovery
0.6134	Remote Similarity	NPD4700	Approved
0.6121	Remote Similarity	NPD7748	Approved
0.6117	Remote Similarity	NPD4243	Approved
0.6116	Remote Similarity	NPD5174	Approved
0.6116	Remote Similarity	NPD5175	Approved
0.6102	Remote Similarity	NPD6084	Phase 2
0.6102	Remote Similarity	NPD6083	Phase 2
0.6102	Remote Similarity	NPD7902	Approved
0.6083	Remote Similarity	NPD5223	Approved
0.6071	Remote Similarity	NPD3618	Phase 1
0.6062	Remote Similarity	NPD7799	Discontinued
0.6055	Remote Similarity	NPD6898	Phase 1
0.6048	Remote Similarity	NPD4729	Approved
0.6048	Remote Similarity	NPD4730	Approved
0.6036	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5222	Approved
0.6017	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5221	Approved
0.6016	Remote Similarity	NPD4768	Approved
0.6016	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD6698	Approved
0.6	Remote Similarity	NPD46	Approved
0.5982	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD5173	Approved
0.5963	Remote Similarity	NPD4748	Discontinued
0.5963	Remote Similarity	NPD7509	Discontinued
0.5962	Remote Similarity	NPD7150	Approved
0.5962	Remote Similarity	NPD7152	Approved
0.5962	Remote Similarity	NPD7151	Approved
0.5954	Remote Similarity	NPD7101	Approved
0.5954	Remote Similarity	NPD7100	Approved
0.5952	Remote Similarity	NPD5250	Approved
0.5952	Remote Similarity	NPD5248	Approved
0.5952	Remote Similarity	NPD5249	Phase 3
0.5952	Remote Similarity	NPD5247	Approved
0.5952	Remote Similarity	NPD5251	Approved
0.5948	Remote Similarity	NPD7515	Phase 2
0.5943	Remote Similarity	NPD8264	Approved
0.5932	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD4753	Phase 2
0.5899	Remote Similarity	NPD8338	Approved
0.5882	Remote Similarity	NPD4697	Phase 3
0.5878	Remote Similarity	NPD6335	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