NPASS Compound

Structure

NPC472235 OpenBabel07101719512D 45 52 0 0 1 0 0 0 0 0999 V2000 -4.4956 3.6413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4546 4.7713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0585 3.3025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0396 3.3025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8254 2.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5767 1.1685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2484 -0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2484 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3987 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7291 2.6188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3301 3.5151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5491 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 2.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7496 3.5498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2914 4.8628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5993 4.0403 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4417 4.3722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3987 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 1.9623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3987 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5491 2.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3953 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 2.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8497 2.4528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.9623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0205 4.2063 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6457 3.4125 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8497 0.4906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2484 2.4528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 2.9434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0518 5.7292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6994 2.9434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4196 5.1026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6215 3.3100 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 24 1 0 0 0 0 3 31 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 34 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 25 2 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 32 1 0 0 0 0 15 17 1 0 0 0 0 15 34 1 0 0 0 0 16 18 1 0 0 0 0 16 33 1 0 0 0 0 17 36 1 0 0 0 0 18 37 1 0 0 0 0 19 25 1 0 0 0 0 19 29 1 0 0 0 0 20 26 1 0 0 0 0 20 28 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 22 35 1 0 0 0 0 23 1 1 1 0 0 0 23 30 1 0 0 0 0 24 36 1 1 0 0 0 26 31 1 0 0 0 0 26 32 1 6 0 0 0 27 31 1 0 0 0 0 27 39 2 0 0 0 0 28 38 1 6 0 0 0 28 42 1 0 0 0 0 29 40 2 0 0 0 0 29 42 1 0 0 0 0 30 41 2 0 0 0 0 30 43 1 0 0 0 0 32 37 1 1 0 0 0 33 34 1 1 0 0 0 34 38 1 1 0 0 0 35 21 1 6 0 0 0 35 43 1 0 0 0 0 35 44 1 0 0 0 0 36 33 1 6 0 0 0 36 44 1 0 0 0 0 37 38 1 1 0 0 0 37 45 1 0 0 0 0 38 45 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.31
Volume:	520.929
LogP:	2.743
LogD:	2.786
LogS:	-4.743
# Rotatable Bonds:	0
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.471
Synthetic Accessibility Score:	6.474
Fsp3:	0.9
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:	-5.223
MDCK Permeability:	2.3522801711806096e-05
Pgp-inhibitor:	0.78
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.926
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.993
Plasma Protein Binding (PPB):	75.8896255493164%
Volume Distribution (VD):	1.027
Pgp-substrate:	20.3367862701416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.246
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.119
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	9.798
Half-life (T1/2):	0.568

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.321
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.299
Carcinogencity:	0.887
Eye Corrosion:	0.008
Eye Irritation:	0.104
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC472235

Natural Product ID:	NPC472235
*Common Name:**	KMYRSXWWSSXABO-WZACHXDTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KMYRSXWWSSXABO-WZACHXDTSA-N
Standard InCHI:	InChI=1S/C38H50O7/c1-23-21-35(43-30(23)41)22-24(2)36(44-35)17-15-34(7)33(36,6)16-18-37-32(5)14-13-27(39)31(3,4)26(32)20-28(38(34,37)45-37)42-29(40)19-25-11-9-8-10-12-25/h8-12,23-24,26,28H,13-22H2,1-7H3/t23-,24-,26+,28+,32+,33+,34-,35-,36-,37+,38+/m1/s1
SMILES:	CC1CC2(CC(C3(O2)CCC4(C3(CCC56C4(O5)C(CC7C6(CCC(=O)C7(C)C)C)OC(=O)CC8=CC=CC=C8)C)C)C)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3353852
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33399	abies faxoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25554367]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[448457]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	50000.0	nM	PMID[448457]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[448457]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[448457]

☑ 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 NPC472235 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	411
0.1-0.2	1373
0.2-0.3	2953
0.3-0.4	6738
0.4-0.5	13360
0.5-0.6	14547
0.6-0.7	2805
0.7-0.8	505
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472236
0.8217	Intermediate Similarity	NPC477491
0.8112	Intermediate Similarity	NPC471911
0.8112	Intermediate Similarity	NPC4242
0.8105	Intermediate Similarity	NPC471176
0.8063	Intermediate Similarity	NPC477488
0.8052	Intermediate Similarity	NPC154675
0.8027	Intermediate Similarity	NPC325078
0.8	Intermediate Similarity	NPC40138
0.7973	Intermediate Similarity	NPC471856
0.7973	Intermediate Similarity	NPC475135
0.7961	Intermediate Similarity	NPC475417
0.7961	Intermediate Similarity	NPC475561
0.7922	Intermediate Similarity	NPC472658
0.7922	Intermediate Similarity	NPC472657
0.7898	Intermediate Similarity	NPC326328
0.7898	Intermediate Similarity	NPC309991
0.7898	Intermediate Similarity	NPC323356
0.7898	Intermediate Similarity	NPC471138
0.7891	Intermediate Similarity	NPC475652
0.7891	Intermediate Similarity	NPC210591
0.7891	Intermediate Similarity	NPC214550
0.7862	Intermediate Similarity	NPC478073
0.7847	Intermediate Similarity	NPC475493
0.7843	Intermediate Similarity	NPC254558
0.7838	Intermediate Similarity	NPC473112
0.7838	Intermediate Similarity	NPC473758
0.7838	Intermediate Similarity	NPC48017
0.7838	Intermediate Similarity	NPC476094
0.7838	Intermediate Similarity	NPC473085
0.7838	Intermediate Similarity	NPC4341
0.7838	Intermediate Similarity	NPC184747
0.7838	Intermediate Similarity	NPC473440
0.7838	Intermediate Similarity	NPC473060
0.7838	Intermediate Similarity	NPC147880
0.7838	Intermediate Similarity	NPC473613
0.7838	Intermediate Similarity	NPC473109
0.7838	Intermediate Similarity	NPC211137
0.7838	Intermediate Similarity	NPC200592
0.7838	Intermediate Similarity	NPC43241
0.7838	Intermediate Similarity	NPC473081
0.7832	Intermediate Similarity	NPC3450
0.7832	Intermediate Similarity	NPC122504
0.7823	Intermediate Similarity	NPC283375
0.7823	Intermediate Similarity	NPC475373
0.7823	Intermediate Similarity	NPC183122
0.7821	Intermediate Similarity	NPC475638
0.7821	Intermediate Similarity	NPC290683
0.7821	Intermediate Similarity	NPC475548
0.7821	Intermediate Similarity	NPC326235
0.7821	Intermediate Similarity	NPC323001
0.7801	Intermediate Similarity	NPC473082
0.78	Intermediate Similarity	NPC131966
0.78	Intermediate Similarity	NPC191387
0.7799	Intermediate Similarity	NPC475536
0.7799	Intermediate Similarity	NPC165234
0.7799	Intermediate Similarity	NPC275477
0.7793	Intermediate Similarity	NPC159811
0.7785	Intermediate Similarity	NPC471862
0.7778	Intermediate Similarity	NPC472418
0.7771	Intermediate Similarity	NPC318447
0.7771	Intermediate Similarity	NPC322048
0.7764	Intermediate Similarity	NPC325732
0.7764	Intermediate Similarity	NPC324769
0.7764	Intermediate Similarity	NPC61891
0.775	Intermediate Similarity	NPC475300
0.775	Intermediate Similarity	NPC475437
0.775	Intermediate Similarity	NPC473797
0.775	Intermediate Similarity	NPC475505
0.775	Intermediate Similarity	NPC475464
0.775	Intermediate Similarity	NPC473641
0.7748	Intermediate Similarity	NPC470231
0.774	Intermediate Similarity	NPC474608
0.7733	Intermediate Similarity	NPC63737
0.7733	Intermediate Similarity	NPC140021
0.7722	Intermediate Similarity	NPC49297
0.7718	Intermediate Similarity	NPC79921
0.7718	Intermediate Similarity	NPC475400
0.7716	Intermediate Similarity	NPC471861
0.7707	Intermediate Similarity	NPC70344
0.7703	Intermediate Similarity	NPC184109
0.7697	Intermediate Similarity	NPC471100
0.7697	Intermediate Similarity	NPC471107
0.7692	Intermediate Similarity	NPC471135
0.7688	Intermediate Similarity	NPC43304
0.7688	Intermediate Similarity	NPC477188
0.7688	Intermediate Similarity	NPC477190
0.7687	Intermediate Similarity	NPC195647
0.7687	Intermediate Similarity	NPC66761
0.7687	Intermediate Similarity	NPC472577
0.7687	Intermediate Similarity	NPC17877
0.7687	Intermediate Similarity	NPC291638
0.7682	Intermediate Similarity	NPC473673
0.7682	Intermediate Similarity	NPC191082
0.7682	Intermediate Similarity	NPC270498
0.7682	Intermediate Similarity	NPC246480
0.7682	Intermediate Similarity	NPC147217
0.7682	Intermediate Similarity	NPC475429
0.7682	Intermediate Similarity	NPC177340
0.7682	Intermediate Similarity	NPC139067
0.7682	Intermediate Similarity	NPC477894
0.7658	Intermediate Similarity	NPC181924
0.7647	Intermediate Similarity	NPC474241
0.7643	Intermediate Similarity	NPC469456
0.7643	Intermediate Similarity	NPC282239
0.764	Intermediate Similarity	NPC66193
0.7632	Intermediate Similarity	NPC57628
0.7632	Intermediate Similarity	NPC95265
0.7632	Intermediate Similarity	NPC188865
0.7632	Intermediate Similarity	NPC471912
0.7632	Intermediate Similarity	NPC475122
0.7632	Intermediate Similarity	NPC25768
0.7632	Intermediate Similarity	NPC11685
0.7632	Intermediate Similarity	NPC472569
0.7632	Intermediate Similarity	NPC163719
0.7632	Intermediate Similarity	NPC125106
0.7632	Intermediate Similarity	NPC70716
0.7632	Intermediate Similarity	NPC472573
0.7632	Intermediate Similarity	NPC95810
0.7632	Intermediate Similarity	NPC476974
0.7632	Intermediate Similarity	NPC51314
0.7632	Intermediate Similarity	NPC67777
0.7632	Intermediate Similarity	NPC80895
0.7632	Intermediate Similarity	NPC472570
0.7628	Intermediate Similarity	NPC477905
0.7622	Intermediate Similarity	NPC473423
0.7613	Intermediate Similarity	NPC476173
0.7613	Intermediate Similarity	NPC112216
0.7613	Intermediate Similarity	NPC7095
0.761	Intermediate Similarity	NPC476784
0.7609	Intermediate Similarity	NPC473860
0.7606	Intermediate Similarity	NPC114927
0.7606	Intermediate Similarity	NPC473083
0.76	Intermediate Similarity	NPC477904
0.76	Intermediate Similarity	NPC183270
0.7595	Intermediate Similarity	NPC217091
0.7595	Intermediate Similarity	NPC106895
0.7593	Intermediate Similarity	NPC471134
0.759	Intermediate Similarity	NPC469421
0.7586	Intermediate Similarity	NPC147561
0.7584	Intermediate Similarity	NPC262324
0.7582	Intermediate Similarity	NPC177940
0.7582	Intermediate Similarity	NPC471104
0.7582	Intermediate Similarity	NPC171525
0.7582	Intermediate Similarity	NPC470157
0.7582	Intermediate Similarity	NPC472572
0.7582	Intermediate Similarity	NPC277053
0.7582	Intermediate Similarity	NPC174982
0.7582	Intermediate Similarity	NPC470159
0.7582	Intermediate Similarity	NPC70403
0.7582	Intermediate Similarity	NPC29704
0.7582	Intermediate Similarity	NPC184817
0.7582	Intermediate Similarity	NPC96903
0.7582	Intermediate Similarity	NPC472568
0.7582	Intermediate Similarity	NPC472575
0.7582	Intermediate Similarity	NPC476973
0.7582	Intermediate Similarity	NPC200471
0.7582	Intermediate Similarity	NPC472571
0.7582	Intermediate Similarity	NPC473088
0.7582	Intermediate Similarity	NPC301946
0.7582	Intermediate Similarity	NPC469349
0.7582	Intermediate Similarity	NPC158663
0.7578	Intermediate Similarity	NPC478124
0.7578	Intermediate Similarity	NPC55744
0.7569	Intermediate Similarity	NPC195224
0.7566	Intermediate Similarity	NPC163087
0.7566	Intermediate Similarity	NPC91703
0.7564	Intermediate Similarity	NPC478123
0.7564	Intermediate Similarity	NPC62792
0.7564	Intermediate Similarity	NPC51602
0.7561	Intermediate Similarity	NPC469420
0.7552	Intermediate Similarity	NPC473110
0.7552	Intermediate Similarity	NPC473111
0.7552	Intermediate Similarity	NPC470818
0.7551	Intermediate Similarity	NPC472656
0.755	Intermediate Similarity	NPC16912
0.7548	Intermediate Similarity	NPC250046
0.7548	Intermediate Similarity	NPC81698
0.7548	Intermediate Similarity	NPC473215
0.7548	Intermediate Similarity	NPC60509
0.7547	Intermediate Similarity	NPC469417
0.7547	Intermediate Similarity	NPC472393
0.7546	Intermediate Similarity	NPC473557
0.7546	Intermediate Similarity	NPC473468
0.7546	Intermediate Similarity	NPC475567
0.7534	Intermediate Similarity	NPC470278
0.7532	Intermediate Similarity	NPC475552
0.7532	Intermediate Similarity	NPC473611
0.7532	Intermediate Similarity	NPC34066
0.7532	Intermediate Similarity	NPC473602
0.7532	Intermediate Similarity	NPC478263
0.7531	Intermediate Similarity	NPC478125
0.7531	Intermediate Similarity	NPC322420
0.7516	Intermediate Similarity	NPC241951
0.7516	Intermediate Similarity	NPC470152
0.7516	Intermediate Similarity	NPC472548
0.7516	Intermediate Similarity	NPC475759
0.75	Intermediate Similarity	NPC329913
0.75	Intermediate Similarity	NPC198455
0.75	Intermediate Similarity	NPC165260

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 NPC472235 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	808
0.2-0.3	2071
0.3-0.4	3472
0.4-0.5	1780
0.5-0.6	617
0.6-0.7	66
0.7-0.8	4
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
0.7576	Intermediate Similarity	NPD7799	Discontinued
0.7426	Intermediate Similarity	NPD7094	Approved
0.7426	Intermediate Similarity	NPD6858	Approved
0.7355	Intermediate Similarity	NPD7236	Approved
0.7248	Intermediate Similarity	NPD7961	Discontinued
0.7125	Intermediate Similarity	NPD7239	Suspended
0.7083	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6008	Approved
0.6797	Remote Similarity	NPD6663	Approved
0.678	Remote Similarity	NPD8407	Phase 2
0.6779	Remote Similarity	NPD7736	Approved
0.6753	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6685	Approved
0.6726	Remote Similarity	NPD7057	Phase 3
0.6726	Remote Similarity	NPD4966	Approved
0.6726	Remote Similarity	NPD7058	Phase 2
0.6726	Remote Similarity	NPD4965	Approved
0.6726	Remote Similarity	NPD4967	Phase 2
0.6705	Remote Similarity	NPD8368	Discontinued
0.669	Remote Similarity	NPD7610	Discontinued
0.6689	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7798	Approved
0.6647	Remote Similarity	NPD6234	Discontinued
0.6645	Remote Similarity	NPD5736	Approved
0.6644	Remote Similarity	NPD7741	Discontinued
0.6611	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7685	Pre-registration
0.66	Remote Similarity	NPD7078	Approved
0.6577	Remote Similarity	NPD7492	Approved
0.6571	Remote Similarity	NPD7228	Approved
0.657	Remote Similarity	NPD7199	Phase 2
0.657	Remote Similarity	NPD8127	Discontinued
0.6548	Remote Similarity	NPD37	Approved
0.6538	Remote Similarity	NPD8361	Approved
0.6538	Remote Similarity	NPD8435	Approved
0.6538	Remote Similarity	NPD8360	Approved
0.6536	Remote Similarity	NPD7084	Phase 3
0.6534	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6616	Approved
0.6531	Remote Similarity	NPD6054	Approved
0.6527	Remote Similarity	NPD7028	Phase 2
0.6522	Remote Similarity	NPD5765	Approved
0.6494	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.649	Remote Similarity	NPD8293	Discontinued
0.6483	Remote Similarity	NPD2629	Approved
0.6483	Remote Similarity	NPD4766	Approved
0.6478	Remote Similarity	NPD7305	Phase 1
0.6443	Remote Similarity	NPD6370	Approved
0.6429	Remote Similarity	NPD8434	Phase 2
0.6425	Remote Similarity	NPD7240	Approved
0.6424	Remote Similarity	NPD7507	Approved
0.6419	Remote Similarity	NPD6059	Approved
0.6412	Remote Similarity	NPD5760	Phase 2
0.6412	Remote Similarity	NPD5761	Phase 2
0.6405	Remote Similarity	NPD7319	Approved
0.6402	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6912	Phase 3
0.6387	Remote Similarity	NPD7497	Discontinued
0.6387	Remote Similarity	NPD7055	Discontinued
0.638	Remote Similarity	NPD8166	Discontinued
0.6376	Remote Similarity	NPD6016	Approved
0.6376	Remote Similarity	NPD6015	Approved
0.6369	Remote Similarity	NPD8032	Phase 2
0.6369	Remote Similarity	NPD7458	Discontinued
0.6343	Remote Similarity	NPD3787	Discontinued
0.6333	Remote Similarity	NPD5126	Approved
0.6333	Remote Similarity	NPD6765	Approved
0.6333	Remote Similarity	NPD5125	Phase 3
0.6333	Remote Similarity	NPD5988	Approved
0.6333	Remote Similarity	NPD6764	Approved
0.6327	Remote Similarity	NPD3317	Approved
0.6327	Remote Similarity	NPD6009	Approved
0.6325	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD1989	Approved
0.6309	Remote Similarity	NPD7009	Phase 2
0.629	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6273	Approved
0.6276	Remote Similarity	NPD8297	Approved
0.6276	Remote Similarity	NPD6882	Approved
0.6267	Remote Similarity	NPD3024	Approved
0.6267	Remote Similarity	NPD3025	Approved
0.6265	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8485	Approved
0.6242	Remote Similarity	NPD6065	Approved
0.6225	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD8455	Phase 2
0.6216	Remote Similarity	NPD4198	Discontinued
0.6209	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6005	Phase 3
0.6196	Remote Similarity	NPD6785	Approved
0.6196	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6002	Phase 3
0.6196	Remote Similarity	NPD6784	Approved
0.6196	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6004	Phase 3
0.6184	Remote Similarity	NPD3023	Approved
0.6184	Remote Similarity	NPD3026	Approved
0.6171	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD4234	Approved
0.6138	Remote Similarity	NPD2067	Discontinued
0.6138	Remote Similarity	NPD4233	Approved
0.6136	Remote Similarity	NPD5494	Approved
0.6133	Remote Similarity	NPD7516	Approved
0.6131	Remote Similarity	NPD1693	Approved
0.6131	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4632	Approved
0.612	Remote Similarity	NPD7962	Phase 2
0.6118	Remote Similarity	NPD3019	Approved
0.6111	Remote Similarity	NPD6899	Approved
0.6111	Remote Similarity	NPD7097	Phase 1
0.6111	Remote Similarity	NPD6881	Approved
0.6111	Remote Similarity	NPD7320	Approved
0.6098	Remote Similarity	NPD5763	Approved
0.6098	Remote Similarity	NPD5762	Approved
0.6096	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD6649	Approved
0.6096	Remote Similarity	NPD6650	Approved
0.6096	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD8130	Phase 1
0.6093	Remote Similarity	NPD6319	Approved
0.609	Remote Similarity	NPD3094	Phase 2
0.6087	Remote Similarity	NPD8312	Approved
0.6087	Remote Similarity	NPD8313	Approved
0.6084	Remote Similarity	NPD6402	Approved
0.6084	Remote Similarity	NPD5739	Approved
0.6084	Remote Similarity	NPD5048	Discontinued
0.6084	Remote Similarity	NPD7128	Approved
0.6084	Remote Similarity	NPD6675	Approved
0.6078	Remote Similarity	NPD7604	Phase 2
0.6078	Remote Similarity	NPD8328	Phase 3
0.6075	Remote Similarity	NPD8150	Discontinued
0.6071	Remote Similarity	NPD2066	Phase 3
0.6069	Remote Similarity	NPD6372	Approved
0.6069	Remote Similarity	NPD6373	Approved
0.6067	Remote Similarity	NPD7327	Approved
0.6067	Remote Similarity	NPD7328	Approved
0.6062	Remote Similarity	NPD3614	Approved
0.6062	Remote Similarity	NPD2566	Approved
0.6062	Remote Similarity	NPD4745	Approved
0.6062	Remote Similarity	NPD3088	Approved
0.6062	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD3089	Approved
0.6062	Remote Similarity	NPD7714	Approved
0.6062	Remote Similarity	NPD2574	Discontinued
0.6062	Remote Similarity	NPD2573	Approved
0.6062	Remote Similarity	NPD3615	Approved
0.6062	Remote Similarity	NPD2571	Approved
0.6062	Remote Similarity	NPD3616	Approved
0.6062	Remote Similarity	NPD7715	Approved
0.6062	Remote Similarity	NPD4746	Phase 3
0.6062	Remote Similarity	NPD3087	Approved
0.6062	Remote Similarity	NPD2570	Approved
0.6062	Remote Similarity	NPD3090	Approved
0.6059	Remote Similarity	NPD7606	Phase 3
0.6056	Remote Similarity	NPD7473	Discontinued
0.6053	Remote Similarity	NPD8379	Approved
0.6053	Remote Similarity	NPD8033	Approved
0.6053	Remote Similarity	NPD8378	Approved
0.6053	Remote Similarity	NPD8380	Approved
0.6053	Remote Similarity	NPD8335	Approved
0.6053	Remote Similarity	NPD8296	Approved
0.6051	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD7680	Approved
0.6051	Remote Similarity	NPD6085	Phase 2
0.605	Remote Similarity	NPD8462	Phase 1
0.6048	Remote Similarity	NPD6190	Approved
0.6042	Remote Similarity	NPD5697	Approved
0.6042	Remote Similarity	NPD6412	Phase 2
0.6039	Remote Similarity	NPD5618	Discontinued
0.6038	Remote Similarity	NPD7008	Discontinued
0.6037	Remote Similarity	NPD7137	Phase 2
0.6027	Remote Similarity	NPD6883	Approved
0.6027	Remote Similarity	NPD7102	Approved
0.6027	Remote Similarity	NPD7290	Approved
0.6026	Remote Similarity	NPD6033	Approved
0.6025	Remote Similarity	NPD4140	Approved
0.6022	Remote Similarity	NPD3751	Discontinued
0.602	Remote Similarity	NPD8320	Phase 1
0.602	Remote Similarity	NPD8319	Approved
0.6013	Remote Similarity	NPD2932	Approved
0.6	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD5844	Phase 1
0.5988	Remote Similarity	NPD7487	Discontinued
0.5988	Remote Similarity	NPD4628	Phase 3
0.5988	Remote Similarity	NPD4684	Phase 3
0.5988	Remote Similarity	NPD4686	Approved
0.5988	Remote Similarity	NPD4685	Phase 3
0.5987	Remote Similarity	NPD8377	Approved
0.5987	Remote Similarity	NPD4479	Discontinued
0.5987	Remote Similarity	NPD8294	Approved
0.5986	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD6617	Approved
0.5986	Remote Similarity	NPD6847	Approved
0.5986	Remote Similarity	NPD6869	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