NPASS Compound

Structure

CID260786 OpenBabel06191716062D 34 37 0 0 1 0 0 0 0 0999 V2000 -1.7917 -3.9736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 -2.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2521 1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 -0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1764 2.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7767 -2.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4921 0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 -2.4868 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3011 1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5278 3.5283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4452 3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9921 2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 2.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7468 0.9740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5143 3.6921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5799 3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 2.9158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3265 1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1073 4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 24 1 0 0 0 0 7 24 1 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 20 1 0 0 0 0 10 18 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 26 1 0 0 0 0 12 18 1 0 0 0 0 12 25 1 0 0 0 0 13 18 1 0 0 0 0 13 33 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 16 27 1 6 0 0 0 17 28 2 0 0 0 0 17 33 1 0 0 0 0 19 21 1 0 0 0 0 19 27 1 6 0 0 0 20 25 1 1 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 26 1 6 0 0 0 22 25 1 0 0 0 0 22 29 2 0 0 0 0 23 30 2 0 0 0 0 23 34 1 0 0 0 0 24 26 1 0 0 0 0 25 31 1 1 0 0 0 26 34 1 6 0 0 0 27 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.26
Volume:	489.672
LogP:	3.896
LogD:	2.656
LogS:	-4.356
# Rotatable Bonds:	7
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	5.084
Fsp3:	0.741
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:	-4.84
MDCK Permeability:	1.9881166736013256e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.617

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.88
Plasma Protein Binding (PPB):	64.09917449951172%
Volume Distribution (VD):	1.273
Pgp-substrate:	42.31254577636719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.318
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.251
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.589
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	3.468
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.441
Human Hepatotoxicity (H-HT):	0.807
Drug-inuced Liver Injury (DILI):	0.722
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.43
Carcinogencity:	0.275
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC260786

Natural Product ID:	NPC260786
*Common Name:**	QOSLYAARSBMQOF-NBJLYKDOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QOSLYAARSBMQOF-NBJLYKDOSA-N
Standard InCHI:	InChI=1S/C27H38O7/c1-8-14(2)23(30)34-26-11-16(4)27(32)19(21(26)24(26,6)7)10-18(13-33-17(5)28)12-25(31)20(27)9-15(3)22(25)29/h9-10,14,16,19-21,31-32H,8,11-13H2,1-7H3/t14?,16-,19+,20-,21-,25-,26+,27-/m1/s1
SMILES:	CCC(C)C(=O)O[C@@]12C[C@@H](C)[C@]3([C@@H](C=C(C[C@]4([C@H]3C=C(C)C4=O)O)COC(=O)C)[C@@H]1C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520853
PubChem CID:	198036
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

*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
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18714.1	Rauvolfia verticillata var. hainanensis	Varieties	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18714.1	Rauvolfia verticillata var. hainanensis	Varieties	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11281	Euphorbia fortissima	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11281	Euphorbia fortissima	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25960	Euphorbia triangularis	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
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.5	nmol	PMID[468962]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.7	/nmol	PMID[468962]

☑ 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 NPC260786 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	224
0.1-0.2	1414
0.2-0.3	4418
0.3-0.4	7841
0.4-0.5	13862
0.5-0.6	7788
0.6-0.7	5697
0.7-0.8	1300
0.8-0.85	44
0.85-0.9	49
0.9-0.95	33
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474871
1.0	High Similarity	NPC96739
1.0	High Similarity	NPC174471
0.9903	High Similarity	NPC17138
0.9903	High Similarity	NPC221511
0.9903	High Similarity	NPC215643
0.9903	High Similarity	NPC170212
0.9903	High Similarity	NPC475391
0.9903	High Similarity	NPC265499
0.9903	High Similarity	NPC89227
0.9903	High Similarity	NPC151216
0.9903	High Similarity	NPC101825
0.9808	High Similarity	NPC474937
0.9808	High Similarity	NPC71889
0.9714	High Similarity	NPC474872
0.9615	High Similarity	NPC158523
0.9615	High Similarity	NPC475937
0.9519	High Similarity	NPC153036
0.9444	High Similarity	NPC472760
0.9358	High Similarity	NPC180640
0.9273	High Similarity	NPC471126
0.9273	High Similarity	NPC471128
0.9273	High Similarity	NPC157252
0.9273	High Similarity	NPC145182
0.9273	High Similarity	NPC19336
0.9273	High Similarity	NPC185876
0.9189	High Similarity	NPC52839
0.9174	High Similarity	NPC153651
0.9107	High Similarity	NPC162009
0.9107	High Similarity	NPC257017
0.9091	High Similarity	NPC472397
0.9091	High Similarity	NPC472758
0.9091	High Similarity	NPC471125
0.9091	High Similarity	NPC171905
0.9083	High Similarity	NPC471127
0.9083	High Similarity	NPC234858
0.9083	High Similarity	NPC154363
0.9074	High Similarity	NPC477091
0.9027	High Similarity	NPC472399
0.9009	High Similarity	NPC5991
0.9009	High Similarity	NPC22628
0.9009	High Similarity	NPC5989
0.9009	High Similarity	NPC471108
0.9009	High Similarity	NPC255081
0.9009	High Similarity	NPC275696
0.9	High Similarity	NPC156252
0.9	High Similarity	NPC10721
0.8947	High Similarity	NPC145238
0.8919	High Similarity	NPC146280
0.8919	High Similarity	NPC124676
0.8899	High Similarity	NPC472757
0.887	High Similarity	NPC222307
0.885	High Similarity	NPC472401
0.8839	High Similarity	NPC236918
0.8839	High Similarity	NPC156745
0.8818	High Similarity	NPC472400
0.8772	High Similarity	NPC19464
0.8761	High Similarity	NPC475885
0.8761	High Similarity	NPC472759
0.8761	High Similarity	NPC329080
0.8718	High Similarity	NPC270109
0.8559	High Similarity	NPC236999
0.8532	High Similarity	NPC163004
0.8376	Intermediate Similarity	NPC473802
0.8348	Intermediate Similarity	NPC472667
0.8318	Intermediate Similarity	NPC162973
0.8305	Intermediate Similarity	NPC473919
0.8305	Intermediate Similarity	NPC473709
0.8235	Intermediate Similarity	NPC471939
0.8167	Intermediate Similarity	NPC471940
0.8148	Intermediate Similarity	NPC476081
0.8131	Intermediate Similarity	NPC471413
0.8125	Intermediate Similarity	NPC477103
0.812	Intermediate Similarity	NPC143755
0.8108	Intermediate Similarity	NPC476479
0.8108	Intermediate Similarity	NPC322903
0.807	Intermediate Similarity	NPC159333
0.8056	Intermediate Similarity	NPC471412
0.8051	Intermediate Similarity	NPC310511
0.8036	Intermediate Similarity	NPC273433
0.8036	Intermediate Similarity	NPC477102
0.8019	Intermediate Similarity	NPC29952
0.7984	Intermediate Similarity	NPC476111
0.7982	Intermediate Similarity	NPC71348
0.7965	Intermediate Similarity	NPC257240
0.7965	Intermediate Similarity	NPC5103
0.7963	Intermediate Similarity	NPC474718
0.7963	Intermediate Similarity	NPC470074
0.7963	Intermediate Similarity	NPC47024
0.7949	Intermediate Similarity	NPC475372
0.7946	Intermediate Similarity	NPC275539
0.7946	Intermediate Similarity	NPC189075
0.7937	Intermediate Similarity	NPC243902
0.7934	Intermediate Similarity	NPC15095
0.7931	Intermediate Similarity	NPC270958
0.7931	Intermediate Similarity	NPC148458
0.7931	Intermediate Similarity	NPC470793
0.7931	Intermediate Similarity	NPC176840
0.7931	Intermediate Similarity	NPC270478
0.7928	Intermediate Similarity	NPC472645
0.7913	Intermediate Similarity	NPC25909
0.7913	Intermediate Similarity	NPC469454
0.7913	Intermediate Similarity	NPC469496
0.7913	Intermediate Similarity	NPC469463
0.7913	Intermediate Similarity	NPC477126
0.7913	Intermediate Similarity	NPC202889
0.7909	Intermediate Similarity	NPC120321
0.7903	Intermediate Similarity	NPC34963
0.7903	Intermediate Similarity	NPC475139
0.7903	Intermediate Similarity	NPC180902
0.7895	Intermediate Similarity	NPC317107
0.7895	Intermediate Similarity	NPC304180
0.7895	Intermediate Similarity	NPC179798
0.7886	Intermediate Similarity	NPC221414
0.7886	Intermediate Similarity	NPC35109
0.7881	Intermediate Similarity	NPC312536
0.7876	Intermediate Similarity	NPC471934
0.787	Intermediate Similarity	NPC222011
0.787	Intermediate Similarity	NPC216478
0.7863	Intermediate Similarity	NPC239273
0.7863	Intermediate Similarity	NPC475323
0.7863	Intermediate Similarity	NPC473656
0.7857	Intermediate Similarity	NPC67321
0.7857	Intermediate Similarity	NPC187435
0.7857	Intermediate Similarity	NPC110496
0.785	Intermediate Similarity	NPC473964
0.7845	Intermediate Similarity	NPC238667
0.784	Intermediate Similarity	NPC58029
0.784	Intermediate Similarity	NPC469674
0.784	Intermediate Similarity	NPC469673
0.7838	Intermediate Similarity	NPC118911
0.7833	Intermediate Similarity	NPC222688
0.7826	Intermediate Similarity	NPC475524
0.7826	Intermediate Similarity	NPC4573
0.7826	Intermediate Similarity	NPC269530
0.7826	Intermediate Similarity	NPC76550
0.7826	Intermediate Similarity	NPC100267
0.7826	Intermediate Similarity	NPC123855
0.7826	Intermediate Similarity	NPC470063
0.7826	Intermediate Similarity	NPC277769
0.7826	Intermediate Similarity	NPC317687
0.7823	Intermediate Similarity	NPC241935
0.7823	Intermediate Similarity	NPC279478
0.7823	Intermediate Similarity	NPC220757
0.7823	Intermediate Similarity	NPC196921
0.7818	Intermediate Similarity	NPC475038
0.7818	Intermediate Similarity	NPC109195
0.7818	Intermediate Similarity	NPC22388
0.7818	Intermediate Similarity	NPC474709
0.7815	Intermediate Similarity	NPC4548
0.7807	Intermediate Similarity	NPC475563
0.7807	Intermediate Similarity	NPC475134
0.7807	Intermediate Similarity	NPC253906
0.7798	Intermediate Similarity	NPC476303
0.7798	Intermediate Similarity	NPC469551
0.7797	Intermediate Similarity	NPC257457
0.7797	Intermediate Similarity	NPC311554
0.7797	Intermediate Similarity	NPC118638
0.7797	Intermediate Similarity	NPC470420
0.7797	Intermediate Similarity	NPC153440
0.7788	Intermediate Similarity	NPC29827
0.7788	Intermediate Similarity	NPC94377
0.7787	Intermediate Similarity	NPC217901
0.7787	Intermediate Similarity	NPC63186
0.7778	Intermediate Similarity	NPC473548
0.7778	Intermediate Similarity	NPC473963
0.7778	Intermediate Similarity	NPC190286
0.7778	Intermediate Similarity	NPC100017
0.7778	Intermediate Similarity	NPC471136
0.7778	Intermediate Similarity	NPC475154
0.7778	Intermediate Similarity	NPC223356
0.7778	Intermediate Similarity	NPC69385
0.7778	Intermediate Similarity	NPC471137
0.7778	Intermediate Similarity	NPC476823
0.7778	Intermediate Similarity	NPC475500
0.7778	Intermediate Similarity	NPC182266
0.7778	Intermediate Similarity	NPC179626
0.7769	Intermediate Similarity	NPC204812
0.7769	Intermediate Similarity	NPC469789
0.7768	Intermediate Similarity	NPC179891
0.7768	Intermediate Similarity	NPC469607
0.7768	Intermediate Similarity	NPC477125
0.7768	Intermediate Similarity	NPC34768
0.7768	Intermediate Similarity	NPC1679
0.776	Intermediate Similarity	NPC189393
0.776	Intermediate Similarity	NPC90814
0.7759	Intermediate Similarity	NPC471204
0.7759	Intermediate Similarity	NPC474271
0.7759	Intermediate Similarity	NPC56448
0.7759	Intermediate Similarity	NPC46269
0.7759	Intermediate Similarity	NPC106395
0.775	Intermediate Similarity	NPC67569
0.7748	Intermediate Similarity	NPC478057
0.7748	Intermediate Similarity	NPC176883
0.7748	Intermediate Similarity	NPC254202
0.7748	Intermediate Similarity	NPC476237
0.7742	Intermediate Similarity	NPC162495
0.7739	Intermediate Similarity	NPC118860
0.7739	Intermediate Similarity	NPC473921
0.7739	Intermediate Similarity	NPC231589

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 NPC260786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1811
0.2-0.3	3657
0.3-0.4	2224
0.4-0.5	850
0.5-0.6	229
0.6-0.7	170
0.7-0.8	18
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
0.7965	Intermediate Similarity	NPD6371	Approved
0.7632	Intermediate Similarity	NPD6881	Approved
0.7632	Intermediate Similarity	NPD6899	Approved
0.7611	Intermediate Similarity	NPD6675	Approved
0.7611	Intermediate Similarity	NPD6402	Approved
0.7611	Intermediate Similarity	NPD7128	Approved
0.7611	Intermediate Similarity	NPD5739	Approved
0.7586	Intermediate Similarity	NPD6649	Approved
0.7586	Intermediate Similarity	NPD6650	Approved
0.7565	Intermediate Similarity	NPD6373	Approved
0.7565	Intermediate Similarity	NPD6372	Approved
0.7545	Intermediate Similarity	NPD7638	Approved
0.7544	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.7478	Intermediate Similarity	NPD7320	Approved
0.7477	Intermediate Similarity	NPD7639	Approved
0.7477	Intermediate Similarity	NPD7640	Approved
0.7456	Intermediate Similarity	NPD6008	Approved
0.7436	Intermediate Similarity	NPD6847	Approved
0.7436	Intermediate Similarity	NPD8130	Phase 1
0.7436	Intermediate Similarity	NPD6869	Approved
0.7436	Intermediate Similarity	NPD6617	Approved
0.7417	Intermediate Similarity	NPD7115	Discovery
0.7414	Intermediate Similarity	NPD6012	Approved
0.7414	Intermediate Similarity	NPD6013	Approved
0.7414	Intermediate Similarity	NPD6014	Approved
0.7391	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5701	Approved
0.7373	Intermediate Similarity	NPD8297	Approved
0.7373	Intermediate Similarity	NPD6882	Approved
0.735	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7604	Phase 2
0.7328	Intermediate Similarity	NPD6011	Approved
0.7311	Intermediate Similarity	NPD4632	Approved
0.7297	Intermediate Similarity	NPD6083	Phase 2
0.7297	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD5695	Phase 3
0.7265	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6319	Approved
0.7232	Intermediate Similarity	NPD5696	Approved
0.7227	Intermediate Similarity	NPD6053	Discontinued
0.7193	Intermediate Similarity	NPD5211	Phase 2
0.7179	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5286	Approved
0.7168	Intermediate Similarity	NPD5285	Approved
0.7168	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6009	Approved
0.713	Intermediate Similarity	NPD1695	Approved
0.7117	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5344	Discontinued
0.7097	Intermediate Similarity	NPD6054	Approved
0.7094	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6399	Phase 3
0.7087	Intermediate Similarity	NPD6616	Approved
0.7087	Intermediate Similarity	NPD7507	Approved
0.708	Intermediate Similarity	NPD4225	Approved
0.7069	Intermediate Similarity	NPD5141	Approved
0.7049	Intermediate Similarity	NPD6274	Approved
0.7043	Intermediate Similarity	NPD5224	Approved
0.7043	Intermediate Similarity	NPD5225	Approved
0.7043	Intermediate Similarity	NPD4633	Approved
0.7043	Intermediate Similarity	NPD5226	Approved
0.704	Intermediate Similarity	NPD5983	Phase 2
0.7034	Intermediate Similarity	NPD6686	Approved
0.7031	Intermediate Similarity	NPD7078	Approved
0.7027	Intermediate Similarity	NPD5282	Discontinued
0.7018	Intermediate Similarity	NPD4700	Approved
0.7018	Intermediate Similarity	NPD6648	Approved
0.7016	Intermediate Similarity	NPD7101	Approved
0.7016	Intermediate Similarity	NPD7100	Approved
0.7	Intermediate Similarity	NPD5693	Phase 1
0.6991	Remote Similarity	NPD7902	Approved
0.6984	Remote Similarity	NPD6370	Approved
0.6983	Remote Similarity	NPD5175	Approved
0.6983	Remote Similarity	NPD5174	Approved
0.6977	Remote Similarity	NPD7736	Approved
0.696	Remote Similarity	NPD6059	Approved
0.6957	Remote Similarity	NPD5223	Approved
0.6953	Remote Similarity	NPD6336	Discontinued
0.6952	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6335	Approved
0.6923	Remote Similarity	NPD7319	Approved
0.6917	Remote Similarity	NPD4634	Approved
0.6916	Remote Similarity	NPD1694	Approved
0.6916	Remote Similarity	NPD1696	Phase 3
0.6909	Remote Similarity	NPD6698	Approved
0.6909	Remote Similarity	NPD46	Approved
0.6905	Remote Similarity	NPD6015	Approved
0.6905	Remote Similarity	NPD6016	Approved
0.6899	Remote Similarity	NPD8293	Discontinued
0.6897	Remote Similarity	NPD7632	Discontinued
0.6881	Remote Similarity	NPD6672	Approved
0.6881	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD7748	Approved
0.6855	Remote Similarity	NPD6317	Approved
0.685	Remote Similarity	NPD5988	Approved
0.6818	Remote Similarity	NPD6080	Approved
0.6818	Remote Similarity	NPD6673	Approved
0.6818	Remote Similarity	NPD4753	Phase 2
0.6818	Remote Similarity	NPD6904	Approved
0.6814	Remote Similarity	NPD5210	Approved
0.6814	Remote Similarity	NPD4629	Approved
0.68	Remote Similarity	NPD6313	Approved
0.68	Remote Similarity	NPD7328	Approved
0.68	Remote Similarity	NPD7327	Approved
0.68	Remote Similarity	NPD6314	Approved
0.6772	Remote Similarity	NPD6908	Approved
0.6772	Remote Similarity	NPD6909	Approved
0.6772	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5785	Approved
0.6754	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5221	Approved
0.6754	Remote Similarity	NPD5222	Approved
0.6754	Remote Similarity	NPD4697	Phase 3
0.675	Remote Similarity	NPD4729	Approved
0.675	Remote Similarity	NPD5128	Approved
0.675	Remote Similarity	NPD4730	Approved
0.6746	Remote Similarity	NPD7516	Approved
0.6726	Remote Similarity	NPD7900	Approved
0.6726	Remote Similarity	NPD6001	Approved
0.6726	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4768	Approved
0.6723	Remote Similarity	NPD4767	Approved
0.6696	Remote Similarity	NPD6050	Approved
0.6696	Remote Similarity	NPD5281	Approved
0.6696	Remote Similarity	NPD5284	Approved
0.6696	Remote Similarity	NPD5173	Approved
0.6696	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD6079	Approved
0.6695	Remote Similarity	NPD4754	Approved
0.6692	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6641	Remote Similarity	NPD8033	Approved
0.664	Remote Similarity	NPD6868	Approved
0.6639	Remote Similarity	NPD5251	Approved
0.6639	Remote Similarity	NPD5248	Approved
0.6639	Remote Similarity	NPD5247	Approved
0.6639	Remote Similarity	NPD5249	Phase 3
0.6639	Remote Similarity	NPD5250	Approved
0.6637	Remote Similarity	NPD4202	Approved
0.6636	Remote Similarity	NPD3573	Approved
0.6607	Remote Similarity	NPD5692	Phase 3
0.6606	Remote Similarity	NPD5329	Approved
0.6585	Remote Similarity	NPD5217	Approved
0.6585	Remote Similarity	NPD5216	Approved
0.6585	Remote Similarity	NPD5215	Approved
0.6562	Remote Similarity	NPD8294	Approved
0.6562	Remote Similarity	NPD8377	Approved
0.6549	Remote Similarity	NPD8034	Phase 2
0.6549	Remote Similarity	NPD5694	Approved
0.6549	Remote Similarity	NPD8035	Phase 2
0.6545	Remote Similarity	NPD6098	Approved
0.6545	Remote Similarity	NPD7146	Approved
0.6545	Remote Similarity	NPD7521	Approved
0.6545	Remote Similarity	NPD5690	Phase 2
0.6545	Remote Similarity	NPD3618	Phase 1
0.6545	Remote Similarity	NPD7334	Approved
0.6545	Remote Similarity	NPD6409	Approved
0.6545	Remote Similarity	NPD6684	Approved
0.6545	Remote Similarity	NPD5330	Approved
0.6529	Remote Similarity	NPD6412	Phase 2
0.6514	Remote Similarity	NPD4197	Approved
0.6512	Remote Similarity	NPD8380	Approved
0.6512	Remote Similarity	NPD6921	Approved
0.6512	Remote Similarity	NPD8379	Approved
0.6512	Remote Similarity	NPD8296	Approved
0.6512	Remote Similarity	NPD8335	Approved
0.6512	Remote Similarity	NPD8378	Approved
0.6512	Remote Similarity	NPD7503	Approved
0.6504	Remote Similarity	NPD5169	Approved
0.6504	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5135	Approved
0.6491	Remote Similarity	NPD5778	Approved
0.6491	Remote Similarity	NPD5779	Approved
0.648	Remote Similarity	NPD8133	Approved
0.6466	Remote Similarity	NPD6033	Approved
0.646	Remote Similarity	NPD7838	Discovery
0.6455	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5127	Approved
0.6449	Remote Similarity	NPD4695	Discontinued
0.6429	Remote Similarity	NPD6903	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5959	Approved
0.6397	Remote Similarity	NPD6845	Suspended
0.6396	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5280	Approved
0.6396	Remote Similarity	NPD4694	Approved
0.6372	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4786	Approved
0.633	Remote Similarity	NPD5209	Approved
0.633	Remote Similarity	NPD4221	Approved
0.633	Remote Similarity	NPD4223	Phase 3
0.6328	Remote Similarity	NPD8295	Clinical (unspecified phase)

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