NPASS Compound

Structure

NPC240372 OpenBabel07101718242D 34 37 0 0 1 0 0 0 0 0999 V2000 7.5032 0.6498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6996 0.1066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7961 1.3569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 0.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.0981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2321 0.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3660 2.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 3.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8301 1.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2321 2.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -0.4019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 4.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 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 5 2 0 0 0 0 5 24 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 10 16 1 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 24 1 0 0 0 0 12 27 1 0 0 0 0 13 26 1 0 0 0 0 13 33 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 25 1 1 0 0 0 16 28 1 6 0 0 0 17 12 1 6 0 0 0 17 20 1 0 0 0 0 17 34 1 0 0 0 0 18 25 1 1 0 0 0 18 26 1 0 0 0 0 19 26 1 1 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 22 1 0 0 0 0 21 31 1 1 0 0 0 22 23 1 0 0 0 0 22 32 1 6 0 0 0 23 33 1 6 0 0 0 23 34 1 0 0 0 0 24 2 1 1 0 0 0 25 3 1 1 0 0 0 26 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.29
Volume:	489.075
LogP:	1.324
LogD:	0.985
LogS:	-3.066
# Rotatable Bonds:	5
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.318
Synthetic Accessibility Score:	5.205
Fsp3:	0.846
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.452
MDCK Permeability:	6.598179879802046e-06
Pgp-inhibitor:	0.281
Pgp-substrate:	0.962
Human Intestinal Absorption (HIA):	0.853
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	75.90850067138672%
Volume Distribution (VD):	0.911
Pgp-substrate:	14.243668556213379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.504
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.478
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.508
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	1.066
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.633
Maximum Recommended Daily Dose:	0.684
Skin Sensitization:	0.316
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.049
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC240372

Natural Product ID:	NPC240372
*Common Name:**	Virescenoside O
IUPAC Name:	(2R,3S,4R,5S,6R)-2-[[(1S,2S,4aR,4bR,7R,9R,10aR)-7-ethenyl-2,9-dihydroxy-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-1-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	virescenoside O
Standard InCHIKey:	GOZZSRDPICPZST-RXLIATGPSA-N
Standard InCHI:	InChI=1S/C26H42O8/c1-5-24(2)8-6-15-14(11-24)16(28)10-18-25(15,3)9-7-19(29)26(18,4)13-33-23-22(32)21(31)20(30)17(12-27)34-23/h5,11,15-23,27-32H,1,6-10,12-13H2,2-4H3/t15-,16+,17+,18+,19-,20+,21+,22-,23+,24-,25+,26+/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@H]2C(=C1)[C@@H](C[C@@H]1[C@]2(C)CC[C@@H]([C@]1(C)CO[C@H]1[C@H]([C@@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465082
PubChem CID:	21672034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal 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
NPO32826	acremonium striatisporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[12027733]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20000.0	nM	PMID[480015]

☑ 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 NPC240372 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	239
0.1-0.2	1615
0.2-0.3	4836
0.3-0.4	10935
0.4-0.5	11839
0.5-0.6	6415
0.6-0.7	4460
0.7-0.8	2093
0.8-0.85	201
0.85-0.9	46
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC90583
0.9451	High Similarity	NPC477927
0.9451	High Similarity	NPC72817
0.9451	High Similarity	NPC305160
0.9362	High Similarity	NPC64348
0.9271	High Similarity	NPC162354
0.9175	High Similarity	NPC75608
0.9072	High Similarity	NPC473123
0.9072	High Similarity	NPC473124
0.9053	High Similarity	NPC477928
0.9022	High Similarity	NPC302584
0.898	High Similarity	NPC470768
0.898	High Similarity	NPC203354
0.898	High Similarity	NPC473127
0.898	High Similarity	NPC110656
0.8889	High Similarity	NPC472899
0.8889	High Similarity	NPC470767
0.8889	High Similarity	NPC472898
0.8889	High Similarity	NPC470763
0.8889	High Similarity	NPC472900
0.8878	High Similarity	NPC99627
0.8878	High Similarity	NPC473129
0.8878	High Similarity	NPC473198
0.8866	High Similarity	NPC117714
0.8866	High Similarity	NPC263756
0.8866	High Similarity	NPC470434
0.88	High Similarity	NPC281939
0.88	High Similarity	NPC33053
0.88	High Similarity	NPC231340
0.8788	High Similarity	NPC54521
0.8788	High Similarity	NPC93352
0.8788	High Similarity	NPC109792
0.8788	High Similarity	NPC57065
0.8776	High Similarity	NPC213674
0.8776	High Similarity	NPC256133
0.8776	High Similarity	NPC470571
0.8776	High Similarity	NPC30289
0.8776	High Similarity	NPC76497
0.8763	High Similarity	NPC7341
0.8763	High Similarity	NPC473200
0.8763	High Similarity	NPC469942
0.8738	High Similarity	NPC473567
0.8738	High Similarity	NPC216595
0.8725	High Similarity	NPC65155
0.8725	High Similarity	NPC103627
0.8725	High Similarity	NPC191439
0.8725	High Similarity	NPC170974
0.8723	High Similarity	NPC67398
0.8723	High Similarity	NPC474792
0.8723	High Similarity	NPC91654
0.8713	High Similarity	NPC38376
0.8713	High Similarity	NPC472896
0.8713	High Similarity	NPC472897
0.8713	High Similarity	NPC80210
0.8687	High Similarity	NPC123796
0.8673	High Similarity	NPC47566
0.8673	High Similarity	NPC88000
0.8673	High Similarity	NPC309425
0.8673	High Similarity	NPC4831
0.8673	High Similarity	NPC160734
0.8673	High Similarity	NPC129372
0.8673	High Similarity	NPC285231
0.8673	High Similarity	NPC472023
0.8673	High Similarity	NPC21568
0.866	High Similarity	NPC234287
0.866	High Similarity	NPC158088
0.866	High Similarity	NPC280825
0.8646	High Similarity	NPC207617
0.8632	High Similarity	NPC211238
0.8627	High Similarity	NPC473318
0.8627	High Similarity	NPC195116
0.8627	High Similarity	NPC250089
0.8627	High Similarity	NPC14630
0.8627	High Similarity	NPC28844
0.8627	High Similarity	NPC221110
0.8627	High Similarity	NPC180459
0.8627	High Similarity	NPC473328
0.8627	High Similarity	NPC157530
0.8627	High Similarity	NPC285253
0.8614	High Similarity	NPC257964
0.8602	High Similarity	NPC477917
0.8602	High Similarity	NPC473058
0.86	High Similarity	NPC473734
0.86	High Similarity	NPC471434
0.86	High Similarity	NPC148603
0.86	High Similarity	NPC470885
0.86	High Similarity	NPC187400
0.86	High Similarity	NPC221562
0.86	High Similarity	NPC173583
0.86	High Similarity	NPC471435
0.86	High Similarity	NPC230948
0.8586	High Similarity	NPC272015
0.8586	High Similarity	NPC312553
0.8586	High Similarity	NPC136816
0.8586	High Similarity	NPC288694
0.8586	High Similarity	NPC159036
0.8558	High Similarity	NPC231797
0.8557	High Similarity	NPC243728
0.8557	High Similarity	NPC473890
0.8529	High Similarity	NPC235824
0.8529	High Similarity	NPC126147
0.8515	High Similarity	NPC242748
0.8515	High Similarity	NPC470512
0.8515	High Similarity	NPC138057
0.8515	High Similarity	NPC173859
0.8511	High Similarity	NPC474249
0.8511	High Similarity	NPC261990
0.8511	High Similarity	NPC159876
0.85	High Similarity	NPC8039
0.85	High Similarity	NPC157659
0.85	High Similarity	NPC120123
0.85	High Similarity	NPC245280
0.85	High Similarity	NPC189852
0.85	High Similarity	NPC155010
0.85	High Similarity	NPC211879
0.85	High Similarity	NPC16573
0.85	High Similarity	NPC213190
0.85	High Similarity	NPC473020
0.85	High Similarity	NPC114874
0.85	High Similarity	NPC286969
0.85	High Similarity	NPC472252
0.85	High Similarity	NPC131479
0.85	High Similarity	NPC16520
0.85	High Similarity	NPC31907
0.8485	Intermediate Similarity	NPC267510
0.8485	Intermediate Similarity	NPC280991
0.8476	Intermediate Similarity	NPC473159
0.8476	Intermediate Similarity	NPC307642
0.8469	Intermediate Similarity	NPC5358
0.8469	Intermediate Similarity	NPC216260
0.8469	Intermediate Similarity	NPC312325
0.8469	Intermediate Similarity	NPC476895
0.8462	Intermediate Similarity	NPC110494
0.8462	Intermediate Similarity	NPC65034
0.8462	Intermediate Similarity	NPC157474
0.8462	Intermediate Similarity	NPC208189
0.8447	Intermediate Similarity	NPC472901
0.8438	Intermediate Similarity	NPC96736
0.8438	Intermediate Similarity	NPC178949
0.8431	Intermediate Similarity	NPC78034
0.8431	Intermediate Similarity	NPC476594
0.8431	Intermediate Similarity	NPC190395
0.8431	Intermediate Similarity	NPC472390
0.8421	Intermediate Similarity	NPC289361
0.8416	Intermediate Similarity	NPC475365
0.8416	Intermediate Similarity	NPC165033
0.8416	Intermediate Similarity	NPC312774
0.8416	Intermediate Similarity	NPC273879
0.84	Intermediate Similarity	NPC154452
0.84	Intermediate Similarity	NPC214277
0.84	Intermediate Similarity	NPC150463
0.8384	Intermediate Similarity	NPC282669
0.8384	Intermediate Similarity	NPC473790
0.8384	Intermediate Similarity	NPC91497
0.8381	Intermediate Similarity	NPC476305
0.8381	Intermediate Similarity	NPC477050
0.8381	Intermediate Similarity	NPC473125
0.8367	Intermediate Similarity	NPC239547
0.8367	Intermediate Similarity	NPC125551
0.8367	Intermediate Similarity	NPC476893
0.8367	Intermediate Similarity	NPC309503
0.8367	Intermediate Similarity	NPC155319
0.8367	Intermediate Similarity	NPC91197
0.8367	Intermediate Similarity	NPC96597
0.8365	Intermediate Similarity	NPC472717
0.8365	Intermediate Similarity	NPC141433
0.8351	Intermediate Similarity	NPC100892
0.8351	Intermediate Similarity	NPC477969
0.8351	Intermediate Similarity	NPC135224
0.8351	Intermediate Similarity	NPC477970
0.8351	Intermediate Similarity	NPC476894
0.8333	Intermediate Similarity	NPC309448
0.8333	Intermediate Similarity	NPC26798
0.8333	Intermediate Similarity	NPC473923
0.8333	Intermediate Similarity	NPC160816
0.8333	Intermediate Similarity	NPC208477
0.8333	Intermediate Similarity	NPC194842
0.8333	Intermediate Similarity	NPC473476
0.8333	Intermediate Similarity	NPC69737
0.8333	Intermediate Similarity	NPC208594
0.8333	Intermediate Similarity	NPC269627
0.8333	Intermediate Similarity	NPC127801
0.8333	Intermediate Similarity	NPC152584
0.8333	Intermediate Similarity	NPC473199
0.8318	Intermediate Similarity	NPC146652
0.8302	Intermediate Similarity	NPC49413
0.8302	Intermediate Similarity	NPC40133
0.8302	Intermediate Similarity	NPC44298
0.8302	Intermediate Similarity	NPC473128
0.8302	Intermediate Similarity	NPC290608
0.83	Intermediate Similarity	NPC21064
0.83	Intermediate Similarity	NPC476896
0.83	Intermediate Similarity	NPC121072
0.8286	Intermediate Similarity	NPC472715
0.8286	Intermediate Similarity	NPC473021
0.8286	Intermediate Similarity	NPC472987
0.8269	Intermediate Similarity	NPC204407
0.8269	Intermediate Similarity	NPC167383
0.8269	Intermediate Similarity	NPC57362
0.8269	Intermediate Similarity	NPC237503

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 NPC240372 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1829
0.2-0.3	3923
0.3-0.4	2082
0.4-0.5	712
0.5-0.6	273
0.6-0.7	107
0.7-0.8	22
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7838	Intermediate Similarity	NPD7328	Approved
0.7838	Intermediate Similarity	NPD7327	Approved
0.783	Intermediate Similarity	NPD6686	Approved
0.7788	Intermediate Similarity	NPD7503	Approved
0.7768	Intermediate Similarity	NPD7516	Approved
0.7757	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6412	Phase 2
0.7699	Intermediate Similarity	NPD8377	Approved
0.7699	Intermediate Similarity	NPD8294	Approved
0.7632	Intermediate Similarity	NPD8379	Approved
0.7632	Intermediate Similarity	NPD8033	Approved
0.7632	Intermediate Similarity	NPD8335	Approved
0.7632	Intermediate Similarity	NPD8296	Approved
0.7632	Intermediate Similarity	NPD8378	Approved
0.7632	Intermediate Similarity	NPD8380	Approved
0.7373	Intermediate Similarity	NPD7507	Approved
0.735	Intermediate Similarity	NPD8328	Phase 3
0.734	Intermediate Similarity	NPD7645	Phase 2
0.7281	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7319	Approved
0.7168	Intermediate Similarity	NPD8133	Approved
0.71	Intermediate Similarity	NPD7524	Approved
0.7034	Intermediate Similarity	NPD8515	Approved
0.7034	Intermediate Similarity	NPD8516	Approved
0.7034	Intermediate Similarity	NPD8517	Approved
0.7034	Intermediate Similarity	NPD8513	Phase 3
0.7009	Intermediate Similarity	NPD7640	Approved
0.7009	Intermediate Similarity	NPD7639	Approved
0.6975	Remote Similarity	NPD6370	Approved
0.697	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5344	Discontinued
0.6923	Remote Similarity	NPD8171	Discontinued
0.6916	Remote Similarity	NPD7638	Approved
0.6916	Remote Similarity	NPD4225	Approved
0.6907	Remote Similarity	NPD7525	Registered
0.6869	Remote Similarity	NPD6695	Phase 3
0.6829	Remote Similarity	NPD7736	Approved
0.6807	Remote Similarity	NPD6054	Approved
0.6737	Remote Similarity	NPD8264	Approved
0.6696	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6067	Discontinued
0.6638	Remote Similarity	NPD6882	Approved
0.6633	Remote Similarity	NPD6929	Approved
0.6614	Remote Similarity	NPD8449	Approved
0.6613	Remote Similarity	NPD8293	Discontinued
0.6612	Remote Similarity	NPD6015	Approved
0.6612	Remote Similarity	NPD6016	Approved
0.6606	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7750	Discontinued
0.6602	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7492	Approved
0.6579	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3168	Discontinued
0.6566	Remote Similarity	NPD7514	Phase 3
0.6566	Remote Similarity	NPD7332	Phase 2
0.6566	Remote Similarity	NPD6931	Approved
0.6566	Remote Similarity	NPD6930	Phase 2
0.6562	Remote Similarity	NPD6942	Approved
0.6562	Remote Similarity	NPD8450	Suspended
0.6562	Remote Similarity	NPD7339	Approved
0.6557	Remote Similarity	NPD5988	Approved
0.6555	Remote Similarity	NPD6009	Approved
0.6545	Remote Similarity	NPD6648	Approved
0.6542	Remote Similarity	NPD7748	Approved
0.6532	Remote Similarity	NPD6616	Approved
0.6531	Remote Similarity	NPD7145	Approved
0.6529	Remote Similarity	NPD6319	Approved
0.6514	Remote Similarity	NPD7902	Approved
0.6509	Remote Similarity	NPD7515	Phase 2
0.6509	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD6902	Approved
0.6496	Remote Similarity	NPD8297	Approved
0.6495	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7078	Approved
0.6471	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD1810	Approved
0.6458	Remote Similarity	NPD1811	Approved
0.6449	Remote Similarity	NPD5779	Approved
0.6449	Remote Similarity	NPD5778	Approved
0.6441	Remote Similarity	NPD4632	Approved
0.6429	Remote Similarity	NPD7632	Discontinued
0.6429	Remote Similarity	NPD5776	Phase 2
0.6429	Remote Similarity	NPD6925	Approved
0.6415	Remote Similarity	NPD6698	Approved
0.6415	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7838	Discovery
0.6415	Remote Similarity	NPD46	Approved
0.64	Remote Similarity	NPD6928	Phase 2
0.6356	Remote Similarity	NPD6430	Approved
0.6356	Remote Similarity	NPD6429	Approved
0.6355	Remote Similarity	NPD7087	Discontinued
0.6355	Remote Similarity	NPD7983	Approved
0.6355	Remote Similarity	NPD6411	Approved
0.6349	Remote Similarity	NPD8074	Phase 3
0.6327	Remote Similarity	NPD6933	Approved
0.6316	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6399	Phase 3
0.6293	Remote Similarity	NPD6881	Approved
0.6293	Remote Similarity	NPD6899	Approved
0.6283	Remote Similarity	NPD5211	Phase 2
0.6271	Remote Similarity	NPD6650	Approved
0.6271	Remote Similarity	NPD6649	Approved
0.6263	Remote Similarity	NPD6932	Approved
0.6261	Remote Similarity	NPD6402	Approved
0.6261	Remote Similarity	NPD5739	Approved
0.6261	Remote Similarity	NPD7128	Approved
0.6261	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD6893	Approved
0.6239	Remote Similarity	NPD7900	Approved
0.6239	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7625	Phase 1
0.6207	Remote Similarity	NPD5697	Approved
0.6207	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6079	Approved
0.62	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4159	Approved
0.619	Remote Similarity	NPD3618	Phase 1
0.6186	Remote Similarity	NPD7290	Approved
0.6186	Remote Similarity	NPD6883	Approved
0.6186	Remote Similarity	NPD7102	Approved
0.6186	Remote Similarity	NPD4634	Approved
0.6176	Remote Similarity	NPD6898	Phase 1
0.6174	Remote Similarity	NPD5141	Approved
0.6172	Remote Similarity	NPD6033	Approved
0.6168	Remote Similarity	NPD6101	Approved
0.6168	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5328	Approved
0.616	Remote Similarity	NPD5126	Approved
0.616	Remote Similarity	NPD5125	Phase 3
0.6154	Remote Similarity	NPD4786	Approved
0.6154	Remote Similarity	NPD7320	Approved
0.6146	Remote Similarity	NPD2686	Approved
0.6146	Remote Similarity	NPD2687	Approved
0.6146	Remote Similarity	NPD2254	Approved
0.6134	Remote Similarity	NPD6617	Approved
0.6134	Remote Similarity	NPD8130	Phase 1
0.6134	Remote Similarity	NPD6847	Approved
0.6134	Remote Similarity	NPD6869	Approved
0.6122	Remote Similarity	NPD6924	Approved
0.6122	Remote Similarity	NPD6926	Approved
0.6121	Remote Similarity	NPD5357	Phase 1
0.6121	Remote Similarity	NPD6640	Phase 3
0.6117	Remote Similarity	NPD3667	Approved
0.6111	Remote Similarity	NPD7604	Phase 2
0.6106	Remote Similarity	NPD5286	Approved
0.6106	Remote Similarity	NPD5285	Approved
0.6106	Remote Similarity	NPD4696	Approved
0.6102	Remote Similarity	NPD6012	Approved
0.6102	Remote Similarity	NPD6013	Approved
0.6102	Remote Similarity	NPD6014	Approved
0.6082	Remote Similarity	NPD7150	Approved
0.6082	Remote Similarity	NPD7152	Approved
0.6082	Remote Similarity	NPD7151	Approved
0.608	Remote Similarity	NPD6921	Approved
0.608	Remote Similarity	NPD5983	Phase 2
0.6078	Remote Similarity	NPD7509	Discontinued
0.6071	Remote Similarity	NPD4755	Approved
0.6068	Remote Similarity	NPD5701	Approved
0.6058	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3669	Approved
0.6055	Remote Similarity	NPD8035	Phase 2
0.6055	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD6051	Approved
0.6017	Remote Similarity	NPD6011	Approved
0.6016	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD4202	Approved
0.5982	Remote Similarity	NPD5221	Approved
0.5982	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7839	Suspended
0.5982	Remote Similarity	NPD5222	Approved
0.5981	Remote Similarity	NPD3573	Approved
0.598	Remote Similarity	NPD6683	Phase 2
0.5979	Remote Similarity	NPD7143	Approved
0.5979	Remote Similarity	NPD7144	Approved
0.5978	Remote Similarity	NPD368	Approved
0.5965	Remote Similarity	NPD4700	Approved
0.5963	Remote Similarity	NPD7136	Phase 2
0.596	Remote Similarity	NPD4785	Approved
0.596	Remote Similarity	NPD4784	Approved
0.5948	Remote Similarity	NPD5175	Approved
0.5948	Remote Similarity	NPD5174	Approved
0.5943	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD8342	Approved
0.5938	Remote Similarity	NPD8340	Approved
0.5938	Remote Similarity	NPD8341	Approved
0.5938	Remote Similarity	NPD8299	Approved
0.5929	Remote Similarity	NPD6674	Discontinued
0.5929	Remote Similarity	NPD6084	Phase 2
0.5929	Remote Similarity	NPD5173	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