NPASS Compound

Structure

NPC475452 OpenBabel07101718182D 43 47 0 0 1 0 0 0 0 0999 V2000 -0.7853 5.0418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2092 1.6324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5034 4.7903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8195 1.9673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7091 2.9402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8219 0.1450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4133 4.2905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2307 1.6684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9518 -0.0942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1038 -0.5838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9518 0.8849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2558 -0.0942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1038 1.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4078 1.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4078 2.3537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7012 0.8979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8620 0.3933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4050 3.5078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0015 3.3013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6692 2.7879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4742 3.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2558 0.8849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7046 2.6198 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1343 1.7761 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0239 2.7490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3779 4.4587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7102 0.8390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5598 2.8433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3043 1.8786 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2737 1.7405 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5269 3.5638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0757 0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9217 2.3582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8833 0.4225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1361 2.8433 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7146 5.3782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1682 -0.0264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5598 3.8224 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0223 4.4030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0059 3.7074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7317 0.8751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7119 2.3537 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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 21 1 0 0 0 0 4 33 1 0 0 0 0 5 33 1 0 0 0 0 7 26 1 0 0 0 0 8 27 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 22 2 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 17 34 1 0 0 0 0 18 21 2 0 0 0 0 19 23 1 0 0 0 0 19 35 1 0 0 0 0 20 40 1 0 0 0 0 21 31 1 0 0 0 0 23 20 1 1 0 0 0 23 30 1 0 0 0 0 24 16 1 1 0 0 0 24 25 1 0 0 0 0 24 33 1 0 0 0 0 25 18 1 1 0 0 0 25 33 1 0 0 0 0 26 36 2 0 0 0 0 26 40 1 0 0 0 0 27 37 2 0 0 0 0 27 41 1 0 0 0 0 28 38 2 0 0 0 0 28 42 1 0 0 0 0 29 30 1 0 0 0 0 29 32 1 0 0 0 0 29 35 1 1 0 0 0 30 41 1 1 0 0 0 31 35 1 0 0 0 0 31 39 2 0 0 0 0 32 34 1 6 0 0 0 32 43 1 0 0 0 0 34 6 1 6 0 0 0 34 43 1 0 0 0 0 35 42 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.3
Volume:	617.727
LogP:	5.191
LogD:	4.581
LogS:	-5.341
# Rotatable Bonds:	11
TPSA:	108.5
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.165
Synthetic Accessibility Score:	5.487
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:	-4.964
MDCK Permeability:	5.301346755004488e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.509
30% Bioavailability (F30%):	0.68

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	95.34857940673828%
Volume Distribution (VD):	1.321
Pgp-substrate:	3.5744194984436035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.591
CYP2C19-substrate:	0.078
CYP2C9-inhibitor:	0.869
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.716
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.728

ADMET: Excretion

Clearance (CL):	9.282
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.823
Human Hepatotoxicity (H-HT):	0.962
Drug-inuced Liver Injury (DILI):	0.815
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.582
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.968
Carcinogencity:	0.066
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.466

Download Data

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

Natural Product: NPC475452

Natural Product ID:	NPC475452
*Common Name:**	Latilagascene H
IUPAC Name:	n.a.
Synonyms:	Latilagascene H
Standard InCHIKey:	XAQUREKNYOFGSI-BNGAZFELSA-N
Standard InCHI:	InChI=1S/C35H44O8/c1-7-26(36)40-20-23-19-35(42-28(38)15-14-22-12-10-9-11-13-22)29(30(23)41-27(37)8-2)32-34(6,43-32)17-16-24-25(33(24,4)5)18-21(3)31(35)39/h9-15,18,23-25,29-30,32H,7-8,16-17,19-20H2,1-6H3/b15-14+,21-18+/t23-,24+,25-,29-,30+,32-,34-,35-/m1/s1
SMILES:	CCC(=O)O[C@H]1[C@@H](COC(=O)CC)C[C@]2([C@H]1[C@H]1O[C@]1(C)CC[C@H]1[C@@H](/C=C(/C2=O)C)C1(C)C)OC(=O)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505927
PubChem CID:	44588891
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18824363]
NPO15009	Euphorbia lagascae	Species	Euphorbiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[6736971]
NPO15009	Euphorbia lagascae	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	8

Activity Type	# Activity
Individual Protein	4
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	61.6	n.a.	PMID[453295]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	427.4	n.a.	PMID[453295]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	78.0	n.a.	PMID[453295]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	541.3	n.a.	PMID[453295]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ID50	=	25.3	ug ml-1	PMID[453295]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ID50	=	17.5	ug ml-1	PMID[453295]
NPT35	Others	n.a.		LogP	=	6.9	n.a.	PMID[453295]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	FICI	=	0.07	n.a.	PMID[453295]

☑ 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 NPC475452 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	320
0.1-0.2	1204
0.2-0.3	2573
0.3-0.4	7460
0.4-0.5	13504
0.5-0.6	14803
0.6-0.7	2504
0.7-0.8	207
0.8-0.85	64
0.85-0.9	43
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475671
0.9508	High Similarity	NPC8990
0.9431	High Similarity	NPC477369
0.9365	High Similarity	NPC3450
0.9365	High Similarity	NPC122504
0.9302	High Similarity	NPC270364
0.9286	High Similarity	NPC37968
0.928	High Similarity	NPC477357
0.9242	High Similarity	NPC473654
0.9104	High Similarity	NPC477094
0.9104	High Similarity	NPC477096
0.9091	High Similarity	NPC276652
0.907	High Similarity	NPC477360
0.9055	High Similarity	NPC477370
0.9048	High Similarity	NPC477363
0.9048	High Similarity	NPC477366
0.904	High Similarity	NPC477362
0.9008	High Similarity	NPC265459
0.9008	High Similarity	NPC290833
0.9008	High Similarity	NPC475262
0.8976	High Similarity	NPC477365
0.8939	High Similarity	NPC285221
0.8939	High Similarity	NPC477358
0.8939	High Similarity	NPC194769
0.8931	High Similarity	NPC472250
0.8915	High Similarity	NPC42234
0.8905	High Similarity	NPC477095
0.8872	High Similarity	NPC86772
0.8824	High Similarity	NPC82467
0.8806	High Similarity	NPC272523
0.8806	High Similarity	NPC325805
0.8788	High Similarity	NPC477359
0.8741	High Similarity	NPC251294
0.8741	High Similarity	NPC475660
0.8714	High Similarity	NPC477101
0.8714	High Similarity	NPC477099
0.8714	High Similarity	NPC477097
0.8676	High Similarity	NPC473497
0.8647	High Similarity	NPC477368
0.8582	High Similarity	NPC232888
0.8582	High Similarity	NPC477367
0.8582	High Similarity	NPC79699
0.8571	High Similarity	NPC477364
0.8551	High Similarity	NPC153214
0.8551	High Similarity	NPC45307
0.854	High Similarity	NPC474303
0.854	High Similarity	NPC475413
0.8531	High Similarity	NPC477098
0.8531	High Similarity	NPC477100
0.8485	Intermediate Similarity	NPC272946
0.8451	Intermediate Similarity	NPC125033
0.8451	Intermediate Similarity	NPC25484
0.8451	Intermediate Similarity	NPC232583
0.8429	Intermediate Similarity	NPC471162
0.8369	Intermediate Similarity	NPC170668
0.8346	Intermediate Similarity	NPC475508
0.831	Intermediate Similarity	NPC205389
0.8309	Intermediate Similarity	NPC472247
0.8273	Intermediate Similarity	NPC187566
0.8235	Intermediate Similarity	NPC153617
0.8235	Intermediate Similarity	NPC471911
0.8235	Intermediate Similarity	NPC4242
0.8222	Intermediate Similarity	NPC233860
0.8188	Intermediate Similarity	NPC184109
0.8162	Intermediate Similarity	NPC472248
0.8102	Intermediate Similarity	NPC134937
0.8102	Intermediate Similarity	NPC28836
0.8102	Intermediate Similarity	NPC324898
0.8102	Intermediate Similarity	NPC298547
0.8088	Intermediate Similarity	NPC239358
0.8043	Intermediate Similarity	NPC200154
0.8043	Intermediate Similarity	NPC279637
0.8043	Intermediate Similarity	NPC149401
0.8014	Intermediate Similarity	NPC242355
0.7986	Intermediate Similarity	NPC202729
0.7971	Intermediate Similarity	NPC311492
0.7956	Intermediate Similarity	NPC233692
0.7943	Intermediate Similarity	NPC473440
0.7929	Intermediate Similarity	NPC327511
0.7929	Intermediate Similarity	NPC205305
0.7929	Intermediate Similarity	NPC27721
0.7902	Intermediate Similarity	NPC131966
0.7902	Intermediate Similarity	NPC191387
0.7883	Intermediate Similarity	NPC472418
0.7872	Intermediate Similarity	NPC121268
0.7872	Intermediate Similarity	NPC53361
0.7872	Intermediate Similarity	NPC473301
0.7852	Intermediate Similarity	NPC473423
0.7832	Intermediate Similarity	NPC63737
0.7832	Intermediate Similarity	NPC475135
0.78	Intermediate Similarity	NPC70344
0.7724	Intermediate Similarity	NPC80895
0.7724	Intermediate Similarity	NPC471912
0.7717	Intermediate Similarity	NPC473522
0.7717	Intermediate Similarity	NPC475277
0.7717	Intermediate Similarity	NPC477093
0.7708	Intermediate Similarity	NPC183540
0.7671	Intermediate Similarity	NPC301946
0.7671	Intermediate Similarity	NPC277053
0.7664	Intermediate Similarity	NPC195224
0.7662	Intermediate Similarity	NPC55744
0.7638	Intermediate Similarity	NPC475495
0.763	Intermediate Similarity	NPC473881
0.763	Intermediate Similarity	NPC469742
0.7619	Intermediate Similarity	NPC475552
0.76	Intermediate Similarity	NPC469647
0.76	Intermediate Similarity	NPC470192
0.76	Intermediate Similarity	NPC469648
0.76	Intermediate Similarity	NPC138641
0.76	Intermediate Similarity	NPC283875
0.76	Intermediate Similarity	NPC22571
0.7591	Intermediate Similarity	NPC472706
0.7589	Intermediate Similarity	NPC322503
0.7589	Intermediate Similarity	NPC470143
0.7586	Intermediate Similarity	NPC140021
0.7551	Intermediate Similarity	NPC134131
0.7551	Intermediate Similarity	NPC25043
0.7551	Intermediate Similarity	NPC471107
0.7551	Intermediate Similarity	NPC471100
0.7548	Intermediate Similarity	NPC475536
0.7548	Intermediate Similarity	NPC165234
0.7534	Intermediate Similarity	NPC95449
0.7533	Intermediate Similarity	NPC472398
0.7518	Intermediate Similarity	NPC15850
0.7518	Intermediate Similarity	NPC476599
0.7518	Intermediate Similarity	NPC470818
0.7517	Intermediate Similarity	NPC473403
0.75	Intermediate Similarity	NPC471176
0.75	Intermediate Similarity	NPC475300
0.75	Intermediate Similarity	NPC469456
0.75	Intermediate Similarity	NPC473641
0.75	Intermediate Similarity	NPC472704
0.75	Intermediate Similarity	NPC475505
0.75	Intermediate Similarity	NPC475437
0.75	Intermediate Similarity	NPC475464
0.75	Intermediate Similarity	NPC473797
0.7483	Intermediate Similarity	NPC233581
0.7483	Intermediate Similarity	NPC145649
0.7482	Intermediate Similarity	NPC225103
0.7481	Intermediate Similarity	NPC475305
0.7467	Intermediate Similarity	NPC254558
0.7463	Intermediate Similarity	NPC473243
0.7451	Intermediate Similarity	NPC11410
0.7447	Intermediate Similarity	NPC469499
0.7447	Intermediate Similarity	NPC238370
0.7447	Intermediate Similarity	NPC209851
0.7445	Intermediate Similarity	NPC284022
0.7429	Intermediate Similarity	NPC473443
0.7429	Intermediate Similarity	NPC472388
0.7426	Intermediate Similarity	NPC472703
0.7424	Intermediate Similarity	NPC475401
0.7417	Intermediate Similarity	NPC51602
0.7415	Intermediate Similarity	NPC284957
0.7391	Intermediate Similarity	NPC473082
0.7386	Intermediate Similarity	NPC251139
0.7379	Intermediate Similarity	NPC170718
0.7376	Intermediate Similarity	NPC472361
0.7376	Intermediate Similarity	NPC470278
0.7368	Intermediate Similarity	NPC477092
0.7368	Intermediate Similarity	NPC94425
0.7365	Intermediate Similarity	NPC470231
0.7361	Intermediate Similarity	NPC52523
0.7361	Intermediate Similarity	NPC217673
0.7357	Intermediate Similarity	NPC237182
0.7357	Intermediate Similarity	NPC226101
0.7348	Intermediate Similarity	NPC476476
0.7347	Intermediate Similarity	NPC51181
0.7347	Intermediate Similarity	NPC472235
0.7347	Intermediate Similarity	NPC182869
0.7347	Intermediate Similarity	NPC472236
0.7329	Intermediate Similarity	NPC87934
0.7329	Intermediate Similarity	NPC162613
0.7324	Intermediate Similarity	NPC80599
0.7324	Intermediate Similarity	NPC475569
0.7324	Intermediate Similarity	NPC472394
0.7324	Intermediate Similarity	NPC475493
0.7319	Intermediate Similarity	NPC473083
0.7315	Intermediate Similarity	NPC127857
0.731	Intermediate Similarity	NPC475373
0.7305	Intermediate Similarity	NPC82712
0.7305	Intermediate Similarity	NPC147561
0.7303	Intermediate Similarity	NPC471103
0.7297	Intermediate Similarity	NPC477894
0.7296	Intermediate Similarity	NPC477491
0.7295	Intermediate Similarity	NPC477354
0.7286	Intermediate Similarity	NPC58061
0.7286	Intermediate Similarity	NPC472707
0.7286	Intermediate Similarity	NPC231627
0.728	Intermediate Similarity	NPC471757
0.728	Intermediate Similarity	NPC78127
0.7279	Intermediate Similarity	NPC266374
0.7273	Intermediate Similarity	NPC282239
0.7273	Intermediate Similarity	NPC323379
0.7273	Intermediate Similarity	NPC473611
0.7273	Intermediate Similarity	NPC472437
0.7273	Intermediate Similarity	NPC327204
0.7273	Intermediate Similarity	NPC21410
0.7273	Intermediate Similarity	NPC473670
0.726	Intermediate Similarity	NPC9905
0.7259	Intermediate Similarity	NPC472708

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 NPC475452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	815
0.2-0.3	1949
0.3-0.4	3288
0.4-0.5	1954
0.5-0.6	793
0.6-0.7	75
0.7-0.8	5
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
0.777	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7236	Approved
0.746	Intermediate Similarity	NPD6685	Approved
0.7422	Intermediate Similarity	NPD2067	Discontinued
0.7417	Intermediate Similarity	NPD7239	Suspended
0.7252	Intermediate Similarity	NPD6858	Approved
0.7252	Intermediate Similarity	NPD7094	Approved
0.7222	Intermediate Similarity	NPD5765	Approved
0.7176	Intermediate Similarity	NPD6912	Phase 3
0.7153	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7799	Discontinued
0.7092	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7961	Discontinued
0.6981	Remote Similarity	NPD7057	Phase 3
0.6981	Remote Similarity	NPD7058	Phase 2
0.697	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6647	Phase 2
0.6818	Remote Similarity	NPD2182	Approved
0.6809	Remote Similarity	NPD6637	Approved
0.6765	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6085	Phase 2
0.6691	Remote Similarity	NPD7741	Discontinued
0.6645	Remote Similarity	NPD6002	Phase 3
0.6645	Remote Similarity	NPD6005	Phase 3
0.6645	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6004	Phase 3
0.6645	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7055	Discontinued
0.6591	Remote Similarity	NPD5048	Discontinued
0.6579	Remote Similarity	NPD7137	Phase 2
0.655	Remote Similarity	NPD7685	Pre-registration
0.6522	Remote Similarity	NPD2629	Approved
0.6515	Remote Similarity	NPD5909	Discontinued
0.6515	Remote Similarity	NPD164	Approved
0.6513	Remote Similarity	NPD7305	Phase 1
0.648	Remote Similarity	NPD3672	Approved
0.648	Remote Similarity	NPD3673	Approved
0.6479	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4198	Discontinued
0.6474	Remote Similarity	NPD6190	Approved
0.6462	Remote Similarity	NPD7798	Approved
0.6457	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD8368	Discontinued
0.6437	Remote Similarity	NPD8407	Phase 2
0.6403	Remote Similarity	NPD4766	Approved
0.6389	Remote Similarity	NPD6287	Discontinued
0.635	Remote Similarity	NPD6649	Approved
0.635	Remote Similarity	NPD6650	Approved
0.6343	Remote Similarity	NPD6008	Approved
0.6336	Remote Similarity	NPD2066	Phase 3
0.6331	Remote Similarity	NPD6010	Discontinued
0.6327	Remote Similarity	NPD6362	Approved
0.6316	Remote Similarity	NPD6355	Discontinued
0.6307	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4628	Phase 3
0.6304	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8297	Approved
0.6296	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD6663	Approved
0.6287	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD1693	Approved
0.6277	Remote Similarity	NPD6371	Approved
0.6275	Remote Similarity	NPD6653	Approved
0.6273	Remote Similarity	NPD7606	Phase 3
0.6271	Remote Similarity	NPD8434	Phase 2
0.6267	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6764	Approved
0.6264	Remote Similarity	NPD6765	Approved
0.6258	Remote Similarity	NPD6599	Discontinued
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD6899	Approved
0.625	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7084	Phase 3
0.6242	Remote Similarity	NPD5760	Phase 2
0.6242	Remote Similarity	NPD5736	Approved
0.6242	Remote Similarity	NPD5761	Phase 2
0.6232	Remote Similarity	NPD8130	Phase 1
0.6231	Remote Similarity	NPD1989	Approved
0.6224	Remote Similarity	NPD9545	Approved
0.6224	Remote Similarity	NPD7009	Phase 2
0.6218	Remote Similarity	NPD5762	Approved
0.6218	Remote Similarity	NPD5763	Approved
0.6214	Remote Similarity	NPD2652	Approved
0.6214	Remote Similarity	NPD2650	Approved
0.6213	Remote Similarity	NPD8127	Discontinued
0.6212	Remote Similarity	NPD1238	Approved
0.6209	Remote Similarity	NPD4685	Phase 3
0.6209	Remote Similarity	NPD4684	Phase 3
0.6209	Remote Similarity	NPD4686	Approved
0.6204	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6372	Approved
0.6204	Remote Similarity	NPD6373	Approved
0.6201	Remote Similarity	NPD8435	Approved
0.6194	Remote Similarity	NPD1930	Approved
0.6194	Remote Similarity	NPD1929	Approved
0.6194	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD6882	Approved
0.6184	Remote Similarity	NPD8032	Phase 2
0.6181	Remote Similarity	NPD5585	Approved
0.6176	Remote Similarity	NPD5697	Approved
0.6174	Remote Similarity	NPD5647	Approved
0.6159	Remote Similarity	NPD7102	Approved
0.6159	Remote Similarity	NPD4234	Approved
0.6159	Remote Similarity	NPD4233	Approved
0.6159	Remote Similarity	NPD7290	Approved
0.6159	Remote Similarity	NPD6883	Approved
0.6154	Remote Similarity	NPD6065	Approved
0.6154	Remote Similarity	NPD7610	Discontinued
0.6149	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD5667	Approved
0.6145	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD1695	Approved
0.6138	Remote Similarity	NPD17	Approved
0.6136	Remote Similarity	NPD5926	Approved
0.6131	Remote Similarity	NPD7075	Discontinued
0.6127	Remote Similarity	NPD3317	Approved
0.6124	Remote Similarity	NPD6784	Approved
0.6124	Remote Similarity	NPD1088	Approved
0.6124	Remote Similarity	NPD6785	Approved
0.6118	Remote Similarity	NPD3764	Approved
0.6115	Remote Similarity	NPD6869	Approved
0.6115	Remote Similarity	NPD6617	Approved
0.6115	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD6847	Approved
0.6115	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1087	Approved
0.6111	Remote Similarity	NPD6319	Approved
0.6111	Remote Similarity	NPD6273	Approved
0.6111	Remote Similarity	NPD8360	Approved
0.6111	Remote Similarity	NPD1282	Approved
0.6111	Remote Similarity	NPD8361	Approved
0.6103	Remote Similarity	NPD6675	Approved
0.6103	Remote Similarity	NPD6402	Approved
0.6103	Remote Similarity	NPD7128	Approved
0.6103	Remote Similarity	NPD5739	Approved
0.6101	Remote Similarity	NPD2575	Approved
0.6101	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD8166	Discontinued
0.6096	Remote Similarity	NPD7604	Phase 2
0.6092	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.609	Remote Similarity	NPD7033	Discontinued
0.6087	Remote Similarity	NPD6799	Approved
0.6087	Remote Similarity	NPD7478	Approved
0.6087	Remote Similarity	NPD6012	Approved
0.6087	Remote Similarity	NPD6014	Approved
0.6087	Remote Similarity	NPD6013	Approved
0.6078	Remote Similarity	NPD3089	Approved
0.6078	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4746	Phase 3
0.6078	Remote Similarity	NPD2574	Discontinued
0.6078	Remote Similarity	NPD3614	Approved
0.6078	Remote Similarity	NPD3087	Approved
0.6078	Remote Similarity	NPD3616	Approved
0.6078	Remote Similarity	NPD2566	Approved
0.6078	Remote Similarity	NPD3088	Approved
0.6078	Remote Similarity	NPD2570	Approved
0.6078	Remote Similarity	NPD3090	Approved
0.6078	Remote Similarity	NPD2573	Approved
0.6078	Remote Similarity	NPD3615	Approved
0.6078	Remote Similarity	NPD4745	Approved
0.6078	Remote Similarity	NPD2571	Approved
0.6071	Remote Similarity	NPD6053	Discontinued
0.6062	Remote Similarity	NPD3887	Approved
0.6054	Remote Similarity	NPD4806	Approved
0.6054	Remote Similarity	NPD4807	Approved
0.6053	Remote Similarity	NPD7008	Discontinued
0.6048	Remote Similarity	NPD7819	Suspended
0.6047	Remote Similarity	NPD5694	Approved
0.6047	Remote Similarity	NPD6050	Approved
0.6047	Remote Similarity	NPD5693	Phase 1
0.6045	Remote Similarity	NPD7962	Phase 2
0.604	Remote Similarity	NPD1876	Approved
0.6029	Remote Similarity	NPD1237	Approved
0.6027	Remote Similarity	NPD5306	Approved
0.6027	Remote Similarity	NPD5305	Approved
0.6026	Remote Similarity	NPD3662	Phase 3
0.6026	Remote Similarity	NPD3664	Approved
0.6026	Remote Similarity	NPD3661	Approved
0.6026	Remote Similarity	NPD3663	Approved
0.6016	Remote Similarity	NPD5346	Phase 2
0.6016	Remote Similarity	NPD5347	Phase 2
0.6015	Remote Similarity	NPD9495	Approved
0.6014	Remote Similarity	NPD3972	Approved
0.6014	Remote Similarity	NPD6406	Approved
0.6014	Remote Similarity	NPD1608	Approved
0.6014	Remote Similarity	NPD7320	Approved
0.6014	Remote Similarity	NPD6011	Approved
0.6013	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8485	Approved
0.6	Remote Similarity	NPD8150	Discontinued
0.6	Remote Similarity	NPD3266	Approved
0.6	Remote Similarity	NPD230	Phase 1
0.6	Remote Similarity	NPD3267	Approved
0.6	Remote Similarity	NPD1932	Approved
0.5988	Remote Similarity	NPD6801	Discontinued
0.5987	Remote Similarity	NPD2613	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