NPASS Compound

Structure

NPC251294 OpenBabel07101719252D 47 51 0 0 1 0 0 0 0 0999 V2000 -4.0879 -2.6577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1213 -6.1070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3762 -5.2657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5024 -6.1166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5535 1.7304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2022 0.6703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8115 -0.0271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3485 -1.1026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8311 -2.7186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0291 -2.2556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8311 -3.6447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2270 -2.7186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0291 -4.1078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4385 -1.6960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2770 -2.4037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8697 -1.5443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0762 -4.2553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1951 -2.4113 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6918 -5.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3346 -4.3405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5439 -5.1915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6999 1.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2270 -3.6447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9859 -1.1285 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6230 -2.7186 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6982 -2.4785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4711 -2.9887 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1343 -1.4924 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8466 -2.8425 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4250 -4.1078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4002 -0.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9029 -0.2061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4750 -0.7950 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0310 -2.4037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9445 -1.5858 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4823 -6.1461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1151 -3.8419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3659 -4.7649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0380 1.9306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4250 -5.0339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8390 -0.0210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7143 -4.7378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5126 -3.9139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7635 -4.6929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6230 -3.6447 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4686 -0.4667 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 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 32 1 0 0 0 0 7 32 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 23 2 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 35 1 0 0 0 0 17 42 1 0 0 0 0 18 1 1 1 0 0 0 18 27 1 0 0 0 0 19 36 2 0 0 0 0 19 42 1 0 0 0 0 20 37 2 0 0 0 0 20 43 1 0 0 0 0 21 38 2 0 0 0 0 21 44 1 0 0 0 0 22 39 2 0 0 0 0 22 46 1 0 0 0 0 23 30 1 0 0 0 0 24 14 1 1 0 0 0 24 28 1 0 0 0 0 24 32 1 0 0 0 0 25 34 1 1 0 0 0 25 45 1 0 0 0 0 26 27 1 0 0 0 0 26 29 1 0 0 0 0 26 35 1 1 0 0 0 27 43 1 1 0 0 0 28 33 1 6 0 0 0 28 34 1 0 0 0 0 29 34 1 6 0 0 0 29 44 1 0 0 0 0 30 40 2 0 0 0 0 30 45 1 0 0 0 0 31 33 1 0 0 0 0 31 35 1 0 0 0 0 31 41 2 0 0 0 0 32 47 1 0 0 0 0 33 8 1 6 0 0 0 33 47 1 0 0 0 0 34 17 1 6 0 0 0 35 46 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.27
Volume:	650.252
LogP:	3.533
LogD:	2.038
LogS:	-4.232
# Rotatable Bonds:	12
TPSA:	157.8
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.24
Synthetic Accessibility Score:	5.425
Fsp3:	0.6
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:	-5.336
MDCK Permeability:	7.368509977823123e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.688
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.428
Plasma Protein Binding (PPB):	50.08479309082031%
Volume Distribution (VD):	1.867
Pgp-substrate:	21.4453182220459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.151
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.109
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.604

ADMET: Excretion

Clearance (CL):	3.858
Half-life (T1/2):	0.697

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.87
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.138
Carcinogencity:	0.046
Eye Corrosion:	0.004
Eye Irritation:	0.032
Respiratory Toxicity:	0.189

Download Data

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

Natural Product: NPC251294

Natural Product ID:	NPC251294
*Common Name:**	NCGTXICVVMZCBN-ZIFGLUNJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NCGTXICVVMZCBN-ZIFGLUNJSA-N
Standard InCHI:	InChI=1S/C35H42O12/c1-18-16-35(46-22(5)39)26(27(18)43-20(3)37)29(44-21(4)38)34(17-42-19(2)36)25(45-30(40)23-12-10-9-11-13-23)15-14-24-28(34)33(8,31(35)41)47-32(24,6)7/h9-15,18,24-29H,16-17H2,1-8H3/t18-,24-,25+,26+,27-,28-,29+,33-,34+,35+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)C)[C@H]([C@]1(COC(=O)C)[C@@H](C=C[C@H]3[C@H]1[C@@](C)(C2=O)OC3(C)C)OC(=O)c1ccccc1)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505401
PubChem CID:	10919402
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids 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
NPO23995	Euphorbia decipiens	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[12808253]
NPO23995	Euphorbia decipiens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510601]
NPO23995	Euphorbia decipiens	Species	Euphorbiaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	750.0	ug ml-1	PMID[575405]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	1090.0	ug ml-1	PMID[575405]

☑ 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 NPC251294 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	359
0.1-0.2	1303
0.2-0.3	2584
0.3-0.4	7110
0.4-0.5	12841
0.5-0.6	13939
0.6-0.7	3935
0.7-0.8	450
0.8-0.85	80
0.85-0.9	75
0.9-0.95	16
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9776	High Similarity	NPC153214
0.9481	High Similarity	NPC187566
0.9398	High Similarity	NPC475262
0.9398	High Similarity	NPC270364
0.9398	High Similarity	NPC290833
0.9398	High Similarity	NPC265459
0.9333	High Similarity	NPC276652
0.9328	High Similarity	NPC285221
0.9328	High Similarity	NPC194769
0.9323	High Similarity	NPC298547
0.9323	High Similarity	NPC134937
0.9323	High Similarity	NPC324898
0.9323	High Similarity	NPC472250
0.9265	High Similarity	NPC475660
0.9259	High Similarity	NPC86772
0.9254	High Similarity	NPC149401
0.9254	High Similarity	NPC279637
0.9197	High Similarity	NPC473654
0.9191	High Similarity	NPC325805
0.9191	High Similarity	NPC272523
0.9118	High Similarity	NPC327511
0.9118	High Similarity	NPC205305
0.9065	High Similarity	NPC82467
0.9058	High Similarity	NPC473497
0.9051	High Similarity	NPC53361
0.9051	High Similarity	NPC121268
0.9023	High Similarity	NPC42234
0.9023	High Similarity	NPC475508
0.9007	High Similarity	NPC170668
0.8971	High Similarity	NPC79699
0.8951	High Similarity	NPC125033
0.8929	High Similarity	NPC477096
0.8929	High Similarity	NPC477094
0.8929	High Similarity	NPC45307
0.8921	High Similarity	NPC474303
0.8921	High Similarity	NPC475413
0.8905	High Similarity	NPC477358
0.8889	High Similarity	NPC477360
0.8881	High Similarity	NPC272946
0.8873	High Similarity	NPC477095
0.8811	High Similarity	NPC205389
0.8759	High Similarity	NPC153617
0.8759	High Similarity	NPC477368
0.8741	High Similarity	NPC475671
0.8741	High Similarity	NPC475452
0.8696	High Similarity	NPC232888
0.8696	High Similarity	NPC477367
0.8696	High Similarity	NPC200154
0.8696	High Similarity	NPC472247
0.869	High Similarity	NPC232583
0.869	High Similarity	NPC25484
0.8686	High Similarity	NPC477364
0.8662	High Similarity	NPC191387
0.8662	High Similarity	NPC131966
0.8623	High Similarity	NPC477359
0.8613	High Similarity	NPC233860
0.8609	High Similarity	NPC55744
0.8571	High Similarity	NPC8990
0.8562	High Similarity	NPC477097
0.8562	High Similarity	NPC477101
0.8562	High Similarity	NPC477099
0.8551	High Similarity	NPC472248
0.8521	High Similarity	NPC242355
0.8514	High Similarity	NPC477098
0.8514	High Similarity	NPC477100
0.8507	High Similarity	NPC477369
0.8489	Intermediate Similarity	NPC28836
0.8478	Intermediate Similarity	NPC239358
0.8467	Intermediate Similarity	NPC122504
0.8467	Intermediate Similarity	NPC3450
0.8462	Intermediate Similarity	NPC475135
0.84	Intermediate Similarity	NPC70344
0.838	Intermediate Similarity	NPC473301
0.8369	Intermediate Similarity	NPC202729
0.8357	Intermediate Similarity	NPC311492
0.8345	Intermediate Similarity	NPC233692
0.831	Intermediate Similarity	NPC27721
0.8276	Intermediate Similarity	NPC95449
0.8231	Intermediate Similarity	NPC475552
0.8188	Intermediate Similarity	NPC477370
0.8175	Intermediate Similarity	NPC476599
0.8175	Intermediate Similarity	NPC477363
0.8175	Intermediate Similarity	NPC477366
0.8163	Intermediate Similarity	NPC471100
0.8163	Intermediate Similarity	NPC471107
0.8162	Intermediate Similarity	NPC477362
0.8129	Intermediate Similarity	NPC37968
0.8121	Intermediate Similarity	NPC473403
0.8116	Intermediate Similarity	NPC477365
0.8116	Intermediate Similarity	NPC477357
0.8082	Intermediate Similarity	NPC183540
0.8069	Intermediate Similarity	NPC162613
0.8069	Intermediate Similarity	NPC87934
0.8067	Intermediate Similarity	NPC254558
0.8056	Intermediate Similarity	NPC475373
0.8041	Intermediate Similarity	NPC134131
0.8041	Intermediate Similarity	NPC471162
0.8041	Intermediate Similarity	NPC25043
0.8014	Intermediate Similarity	NPC266374
0.8013	Intermediate Similarity	NPC51602
0.8013	Intermediate Similarity	NPC472398
0.8	Intermediate Similarity	NPC9905
0.8	Intermediate Similarity	NPC473243
0.7987	Intermediate Similarity	NPC240115
0.7986	Intermediate Similarity	NPC472706
0.7975	Intermediate Similarity	NPC324769
0.7975	Intermediate Similarity	NPC325732
0.7974	Intermediate Similarity	NPC469456
0.7973	Intermediate Similarity	NPC470231
0.7972	Intermediate Similarity	NPC471911
0.7972	Intermediate Similarity	NPC4242
0.7961	Intermediate Similarity	NPC283875
0.7961	Intermediate Similarity	NPC138641
0.7961	Intermediate Similarity	NPC469648
0.7961	Intermediate Similarity	NPC469647
0.7961	Intermediate Similarity	NPC22571
0.7959	Intermediate Similarity	NPC192658
0.7958	Intermediate Similarity	NPC472394
0.7958	Intermediate Similarity	NPC469499
0.7943	Intermediate Similarity	NPC147561
0.7917	Intermediate Similarity	NPC473399
0.7917	Intermediate Similarity	NPC473216
0.7914	Intermediate Similarity	NPC121272
0.7899	Intermediate Similarity	NPC472704
0.7895	Intermediate Similarity	NPC471103
0.7887	Intermediate Similarity	NPC470278
0.7877	Intermediate Similarity	NPC170718
0.7875	Intermediate Similarity	NPC40138
0.7867	Intermediate Similarity	NPC312393
0.7857	Intermediate Similarity	NPC282239
0.7857	Intermediate Similarity	NPC473670
0.7857	Intermediate Similarity	NPC21410
0.7857	Intermediate Similarity	NPC251139
0.7852	Intermediate Similarity	NPC34943
0.7843	Intermediate Similarity	NPC145649
0.7843	Intermediate Similarity	NPC233581
0.7838	Intermediate Similarity	NPC472546
0.7838	Intermediate Similarity	NPC182869
0.7838	Intermediate Similarity	NPC51181
0.7832	Intermediate Similarity	NPC475569
0.7826	Intermediate Similarity	NPC472703
0.7823	Intermediate Similarity	NPC183270
0.7823	Intermediate Similarity	NPC477904
0.7817	Intermediate Similarity	NPC82712
0.7812	Intermediate Similarity	NPC161151
0.781	Intermediate Similarity	NPC50872
0.7806	Intermediate Similarity	NPC106895
0.7806	Intermediate Similarity	NPC11410
0.7806	Intermediate Similarity	NPC217091
0.78	Intermediate Similarity	NPC127857
0.78	Intermediate Similarity	NPC125882
0.7793	Intermediate Similarity	NPC291638
0.7793	Intermediate Similarity	NPC472577
0.7793	Intermediate Similarity	NPC195647
0.7793	Intermediate Similarity	NPC17877
0.7793	Intermediate Similarity	NPC66761
0.7792	Intermediate Similarity	NPC471135
0.7785	Intermediate Similarity	NPC43304
0.7785	Intermediate Similarity	NPC477188
0.7785	Intermediate Similarity	NPC477190
0.7778	Intermediate Similarity	NPC101043
0.7778	Intermediate Similarity	NPC472656
0.7778	Intermediate Similarity	NPC161955
0.7778	Intermediate Similarity	NPC306799
0.7762	Intermediate Similarity	NPC72915
0.7756	Intermediate Similarity	NPC472393
0.7748	Intermediate Similarity	NPC209592
0.7748	Intermediate Similarity	NPC20255
0.7748	Intermediate Similarity	NPC478263
0.7748	Intermediate Similarity	NPC48599
0.7744	Intermediate Similarity	NPC307651
0.7742	Intermediate Similarity	NPC473611
0.7742	Intermediate Similarity	NPC472549
0.774	Intermediate Similarity	NPC217673
0.774	Intermediate Similarity	NPC52523
0.7736	Intermediate Similarity	NPC322420
0.7736	Intermediate Similarity	NPC66193
0.7724	Intermediate Similarity	NPC329913
0.7724	Intermediate Similarity	NPC203486
0.7724	Intermediate Similarity	NPC474608
0.7718	Intermediate Similarity	NPC63737
0.7712	Intermediate Similarity	NPC473214
0.7712	Intermediate Similarity	NPC7095
0.7712	Intermediate Similarity	NPC470245
0.7712	Intermediate Similarity	NPC112216
0.7708	Intermediate Similarity	NPC238370
0.7707	Intermediate Similarity	NPC471102
0.7703	Intermediate Similarity	NPC473081
0.7703	Intermediate Similarity	NPC473060
0.7703	Intermediate Similarity	NPC476094
0.7703	Intermediate Similarity	NPC473112
0.7703	Intermediate Similarity	NPC473085
0.7703	Intermediate Similarity	NPC147880
0.7703	Intermediate Similarity	NPC48017
0.7703	Intermediate Similarity	NPC473109
0.7703	Intermediate Similarity	NPC211137
0.7703	Intermediate Similarity	NPC473758
0.7703	Intermediate Similarity	NPC475400
0.7703	Intermediate Similarity	NPC184747
0.7703	Intermediate Similarity	NPC473613

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 NPC251294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	862
0.2-0.3	1715
0.3-0.4	3130
0.4-0.5	2150
0.5-0.6	885
0.6-0.7	110
0.7-0.8	10
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
0.8163	Intermediate Similarity	NPD7236	Approved
0.8013	Intermediate Similarity	NPD7239	Suspended
0.7888	Intermediate Similarity	NPD7799	Discontinued
0.773	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7058	Phase 2
0.7547	Intermediate Similarity	NPD7057	Phase 3
0.7534	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2182	Approved
0.7114	Intermediate Similarity	NPD7961	Discontinued
0.7113	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2067	Discontinued
0.7052	Intermediate Similarity	NPD8407	Phase 2
0.703	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6858	Approved
0.7029	Intermediate Similarity	NPD7094	Approved
0.6977	Remote Similarity	NPD6765	Approved
0.6977	Remote Similarity	NPD6764	Approved
0.6977	Remote Similarity	NPD8368	Discontinued
0.6963	Remote Similarity	NPD6685	Approved
0.6957	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.694	Remote Similarity	NPD164	Approved
0.6929	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6004	Phase 3
0.6903	Remote Similarity	NPD6005	Phase 3
0.6903	Remote Similarity	NPD6002	Phase 3
0.6897	Remote Similarity	NPD6287	Discontinued
0.689	Remote Similarity	NPD5761	Phase 2
0.689	Remote Similarity	NPD5760	Phase 2
0.6875	Remote Similarity	NPD8434	Phase 2
0.6867	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7741	Discontinued
0.6818	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6784	Approved
0.6818	Remote Similarity	NPD6785	Approved
0.6782	Remote Similarity	NPD7685	Pre-registration
0.678	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6085	Phase 2
0.6772	Remote Similarity	NPD4628	Phase 3
0.6767	Remote Similarity	NPD1238	Approved
0.6741	Remote Similarity	NPD5765	Approved
0.6739	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7137	Phase 2
0.6714	Remote Similarity	NPD6912	Phase 3
0.6711	Remote Similarity	NPD3764	Approved
0.6707	Remote Similarity	NPD6599	Discontinued
0.6704	Remote Similarity	NPD8435	Approved
0.669	Remote Similarity	NPD2629	Approved
0.6643	Remote Similarity	NPD4198	Discontinued
0.6621	Remote Similarity	NPD9545	Approved
0.6618	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD8360	Approved
0.6611	Remote Similarity	NPD8361	Approved
0.6609	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7055	Discontinued
0.6568	Remote Similarity	NPD7075	Discontinued
0.6564	Remote Similarity	NPD6273	Approved
0.6561	Remote Similarity	NPD7305	Phase 1
0.6543	Remote Similarity	NPD6799	Approved
0.6536	Remote Similarity	NPD7008	Discontinued
0.6533	Remote Similarity	NPD1876	Approved
0.6522	Remote Similarity	NPD3887	Approved
0.6522	Remote Similarity	NPD6190	Approved
0.651	Remote Similarity	NPD3972	Approved
0.651	Remote Similarity	NPD6637	Approved
0.65	Remote Similarity	NPD8150	Discontinued
0.6497	Remote Similarity	NPD2569	Approved
0.6497	Remote Similarity	NPD2567	Approved
0.6496	Remote Similarity	NPD6647	Phase 2
0.6488	Remote Similarity	NPD7819	Suspended
0.6486	Remote Similarity	NPD8485	Approved
0.6478	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6355	Discontinued
0.6471	Remote Similarity	NPD6832	Phase 2
0.6452	Remote Similarity	NPD7713	Phase 3
0.6452	Remote Similarity	NPD6663	Approved
0.6449	Remote Similarity	NPD1237	Approved
0.6446	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6801	Discontinued
0.6424	Remote Similarity	NPD5667	Approved
0.6424	Remote Similarity	NPD920	Approved
0.6424	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD17	Approved
0.6415	Remote Similarity	NPD2796	Approved
0.6402	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7009	Phase 2
0.6383	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6362	Approved
0.6377	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD1929	Approved
0.6377	Remote Similarity	NPD1930	Approved
0.6375	Remote Similarity	NPD5763	Approved
0.6375	Remote Similarity	NPD5762	Approved
0.6369	Remote Similarity	NPD230	Phase 1
0.6359	Remote Similarity	NPD8462	Phase 1
0.6358	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD8127	Discontinued
0.6357	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5402	Approved
0.6353	Remote Similarity	NPD3817	Phase 2
0.6352	Remote Similarity	NPD2799	Discontinued
0.6352	Remote Similarity	NPD3748	Approved
0.6346	Remote Similarity	NPD8032	Phase 2
0.6345	Remote Similarity	NPD5951	Approved
0.6345	Remote Similarity	NPD4766	Approved
0.6329	Remote Similarity	NPD6653	Approved
0.6325	Remote Similarity	NPD5403	Approved
0.6303	Remote Similarity	NPD2534	Approved
0.6303	Remote Similarity	NPD2533	Approved
0.6303	Remote Similarity	NPD2532	Approved
0.6303	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5401	Approved
0.6301	Remote Similarity	NPD5494	Approved
0.6299	Remote Similarity	NPD5736	Approved
0.6299	Remote Similarity	NPD3662	Phase 3
0.6299	Remote Similarity	NPD3663	Approved
0.6299	Remote Similarity	NPD3664	Approved
0.6299	Remote Similarity	NPD3661	Approved
0.6296	Remote Similarity	NPD2800	Approved
0.6294	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1608	Approved
0.6286	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5048	Discontinued
0.6277	Remote Similarity	NPD2066	Phase 3
0.6273	Remote Similarity	NPD1471	Phase 3
0.6273	Remote Similarity	NPD2353	Approved
0.6273	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD1202	Approved
0.6269	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD8166	Discontinued
0.6258	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.625	Remote Similarity	NPD969	Suspended
0.625	Remote Similarity	NPD7458	Discontinued
0.625	Remote Similarity	NPD7033	Discontinued
0.6243	Remote Similarity	NPD919	Approved
0.6234	Remote Similarity	NPD5647	Approved
0.6225	Remote Similarity	NPD4806	Approved
0.6225	Remote Similarity	NPD4807	Approved
0.6221	Remote Similarity	NPD3882	Suspended
0.6218	Remote Similarity	NPD6039	Approved
0.6216	Remote Similarity	NPD7610	Discontinued
0.6214	Remote Similarity	NPD5909	Discontinued
0.6213	Remote Similarity	NPD7028	Phase 2
0.6209	Remote Similarity	NPD2199	Approved
0.6209	Remote Similarity	NPD2198	Approved
0.6205	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5306	Approved
0.62	Remote Similarity	NPD5305	Approved
0.6198	Remote Similarity	NPD7497	Discontinued
0.6196	Remote Similarity	NPD1243	Approved
0.6182	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD6650	Approved
0.6181	Remote Similarity	NPD6649	Approved
0.6178	Remote Similarity	NPD2313	Discontinued
0.6178	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7411	Suspended
0.6176	Remote Similarity	NPD6385	Approved
0.6176	Remote Similarity	NPD6386	Approved
0.6176	Remote Similarity	NPD1989	Approved
0.617	Remote Similarity	NPD6008	Approved
0.6169	Remote Similarity	NPD3267	Approved
0.6169	Remote Similarity	NPD3266	Approved
0.6167	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD1241	Discontinued
0.6164	Remote Similarity	NPD6010	Discontinued
0.6163	Remote Similarity	NPD5353	Approved
0.6159	Remote Similarity	NPD7798	Approved
0.6159	Remote Similarity	NPD2575	Approved
0.6159	Remote Similarity	NPD3750	Approved
0.6158	Remote Similarity	NPD2403	Approved
0.6154	Remote Similarity	NPD3226	Approved
0.6149	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD8297	Approved
0.6138	Remote Similarity	NPD6053	Discontinued
0.6135	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD5585	Approved
0.6131	Remote Similarity	NPD7606	Phase 3
0.6129	Remote Similarity	NPD2798	Approved
0.6129	Remote Similarity	NPD2788	Approved
0.6127	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD6651	Approved
0.6121	Remote Similarity	NPD2354	Approved
0.6118	Remote Similarity	NPD4380	Phase 2
0.6107	Remote Similarity	NPD9257	Approved
0.6107	Remote Similarity	NPD9259	Approved
0.6105	Remote Similarity	NPD7460	Discontinued

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