NPASS Compound

Structure

NPC474937 OpenBabel07101718232D 41 44 0 0 1 0 0 0 0 0999 V2000 -6.0540 0.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5604 -2.5386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3371 -0.4352 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 -1.2305 5.4007 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 -5.1806 1.0776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 -3.0256 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 -1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3222 0.5647 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8285 -2.5127 0.0000 C 0 0 0 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 -0.2440 5.2369 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 -3.4488 1.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 -1.5128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 1 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 0.3911 6.0093 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 -3.4338 2.0516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 -1.0258 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 -2.5903 0.5388 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 29 1 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 19 2 0 0 0 0 11 24 1 0 0 0 0 12 22 2 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 31 1 0 0 0 0 14 22 1 0 0 0 0 14 30 1 0 0 0 0 15 22 1 0 0 0 0 15 39 1 0 0 0 0 16 29 1 0 0 0 0 16 40 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 26 1 0 0 0 0 20 32 1 6 0 0 0 21 33 2 0 0 0 0 21 39 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 6 0 0 0 24 30 1 1 0 0 0 24 32 1 0 0 0 0 25 29 1 1 0 0 0 25 31 1 0 0 0 0 26 30 1 0 0 0 0 26 34 2 0 0 0 0 27 35 2 0 0 0 0 27 40 1 0 0 0 0 28 36 2 0 0 0 0 28 41 1 0 0 0 0 29 31 1 6 0 0 0 30 37 1 1 0 0 0 31 41 1 6 0 0 0 32 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.3
Volume:	588.459
LogP:	3.843
LogD:	2.592
LogS:	-4.568
# Rotatable Bonds:	11
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.193
Synthetic Accessibility Score:	5.445
Fsp3:	0.688
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:	-4.967
MDCK Permeability:	1.371204143651994e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.132
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.935
Plasma Protein Binding (PPB):	67.6153793334961%
Volume Distribution (VD):	1.514
Pgp-substrate:	28.00963592529297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.576
CYP2C19-inhibitor:	0.745
CYP2C19-substrate:	0.657
CYP2C9-inhibitor:	0.77
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.922
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	3.806
Half-life (T1/2):	0.236

ADMET: Toxicity

hERG Blockers:	0.45
Human Hepatotoxicity (H-HT):	0.881
Drug-inuced Liver Injury (DILI):	0.638
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.865
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.525
Carcinogencity:	0.29
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC474937

Natural Product ID:	NPC474937
*Common Name:**	YIFUIDOIBAUFGE-NUGUXYSKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YIFUIDOIBAUFGE-NUGUXYSKSA-N
Standard InCHI:	InChI=1S/C32H44O9/c1-9-17(3)27(35)40-16-29(8)25-23-12-22(15-39-21(7)33)14-30(37)24(11-19(5)26(30)34)32(23,38)20(6)13-31(25,29)41-28(36)18(4)10-2/h10-12,17,20,23-25,37-38H,9,13-16H2,1-8H3/b18-10-/t17?,20-,23+,24-,25-,29-,30-,31+,32-/m1/s1
SMILES:	CCC(C)C(=O)OCC1(C2C1(CC(C3(C2C=C(CC4(C3C=C(C4=O)C)O)COC(=O)C)O)C)OC(=O)C(=CC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488754
PubChem CID:	44559777
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
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]
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	=	2.4	nmol	PMID[497097]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.4	/nmol	PMID[497097]

☑ 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 NPC474937 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	233
0.1-0.2	1447
0.2-0.3	4497
0.3-0.4	7966
0.4-0.5	13840
0.5-0.6	7656
0.6-0.7	5686
0.7-0.8	1223
0.8-0.85	40
0.85-0.9	38
0.9-0.95	48
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC215643
0.9904	High Similarity	NPC17138
0.9904	High Similarity	NPC170212
0.9904	High Similarity	NPC475391
0.9904	High Similarity	NPC265499
0.9904	High Similarity	NPC89227
0.9904	High Similarity	NPC221511
0.9904	High Similarity	NPC151216
0.9904	High Similarity	NPC101825
0.9808	High Similarity	NPC260786
0.9808	High Similarity	NPC474871
0.9808	High Similarity	NPC174471
0.9808	High Similarity	NPC96739
0.9717	High Similarity	NPC474872
0.9623	High Similarity	NPC71889
0.9541	High Similarity	NPC180640
0.9455	High Similarity	NPC185876
0.9455	High Similarity	NPC19336
0.945	High Similarity	NPC472760
0.9434	High Similarity	NPC475937
0.9434	High Similarity	NPC158523
0.9369	High Similarity	NPC52839
0.9358	High Similarity	NPC153651
0.934	High Similarity	NPC153036
0.9286	High Similarity	NPC162009
0.9286	High Similarity	NPC257017
0.9279	High Similarity	NPC471128
0.9279	High Similarity	NPC471126
0.9279	High Similarity	NPC157252
0.9279	High Similarity	NPC145182
0.9189	High Similarity	NPC22628
0.9189	High Similarity	NPC471108
0.9189	High Similarity	NPC275696
0.9189	High Similarity	NPC5991
0.9189	High Similarity	NPC255081
0.9189	High Similarity	NPC5989
0.9123	High Similarity	NPC145238
0.9099	High Similarity	NPC472397
0.9099	High Similarity	NPC472758
0.9099	High Similarity	NPC171905
0.9099	High Similarity	NPC471125
0.9083	High Similarity	NPC477091
0.9035	High Similarity	NPC472399
0.9009	High Similarity	NPC10721
0.8947	High Similarity	NPC19464
0.8929	High Similarity	NPC124676
0.8929	High Similarity	NPC146280
0.8919	High Similarity	NPC471127
0.8919	High Similarity	NPC234858
0.8919	High Similarity	NPC154363
0.8879	High Similarity	NPC222307
0.886	High Similarity	NPC472401
0.8839	High Similarity	NPC156252
0.8772	High Similarity	NPC472759
0.8772	High Similarity	NPC329080
0.8739	High Similarity	NPC472757
0.8729	High Similarity	NPC236999
0.8729	High Similarity	NPC270109
0.8684	High Similarity	NPC236918
0.8684	High Similarity	NPC156745
0.8661	High Similarity	NPC472400
0.8609	High Similarity	NPC475885
0.8547	High Similarity	NPC473802
0.8475	Intermediate Similarity	NPC473919
0.8475	Intermediate Similarity	NPC473709
0.8403	Intermediate Similarity	NPC471939
0.8378	Intermediate Similarity	NPC163004
0.8362	Intermediate Similarity	NPC472667
0.8333	Intermediate Similarity	NPC471940
0.8165	Intermediate Similarity	NPC162973
0.8142	Intermediate Similarity	NPC477103
0.8136	Intermediate Similarity	NPC143755
0.8125	Intermediate Similarity	NPC476479
0.8103	Intermediate Similarity	NPC148458
0.8103	Intermediate Similarity	NPC270958
0.8099	Intermediate Similarity	NPC15095
0.8087	Intermediate Similarity	NPC202889
0.8087	Intermediate Similarity	NPC159333
0.8067	Intermediate Similarity	NPC310511
0.8065	Intermediate Similarity	NPC34963
0.8065	Intermediate Similarity	NPC180902
0.8065	Intermediate Similarity	NPC475139
0.8053	Intermediate Similarity	NPC273433
0.8053	Intermediate Similarity	NPC477102
0.8049	Intermediate Similarity	NPC35109
0.8034	Intermediate Similarity	NPC239273
0.8018	Intermediate Similarity	NPC118911
0.8	Intermediate Similarity	NPC476081
0.8	Intermediate Similarity	NPC71348
0.8	Intermediate Similarity	NPC100267
0.8	Intermediate Similarity	NPC58029
0.8	Intermediate Similarity	NPC469674
0.8	Intermediate Similarity	NPC475524
0.8	Intermediate Similarity	NPC469673
0.7984	Intermediate Similarity	NPC279478
0.7984	Intermediate Similarity	NPC241935
0.7984	Intermediate Similarity	NPC220757
0.7984	Intermediate Similarity	NPC196921
0.7982	Intermediate Similarity	NPC471413
0.7982	Intermediate Similarity	NPC475134
0.7982	Intermediate Similarity	NPC475563
0.7966	Intermediate Similarity	NPC311554
0.7966	Intermediate Similarity	NPC257457
0.7966	Intermediate Similarity	NPC118638
0.7965	Intermediate Similarity	NPC322903
0.7953	Intermediate Similarity	NPC243902
0.7949	Intermediate Similarity	NPC470793
0.7937	Intermediate Similarity	NPC473548
0.7937	Intermediate Similarity	NPC223356
0.7937	Intermediate Similarity	NPC475154
0.7937	Intermediate Similarity	NPC471137
0.7937	Intermediate Similarity	NPC476823
0.7937	Intermediate Similarity	NPC100017
0.7937	Intermediate Similarity	NPC471136
0.7937	Intermediate Similarity	NPC182266
0.7937	Intermediate Similarity	NPC475500
0.7931	Intermediate Similarity	NPC25909
0.7931	Intermediate Similarity	NPC477126
0.7913	Intermediate Similarity	NPC475480
0.7913	Intermediate Similarity	NPC473921
0.7913	Intermediate Similarity	NPC475668
0.7909	Intermediate Similarity	NPC471412
0.7903	Intermediate Similarity	NPC221414
0.7903	Intermediate Similarity	NPC162495
0.7899	Intermediate Similarity	NPC472933
0.7895	Intermediate Similarity	NPC471934
0.789	Intermediate Similarity	NPC72647
0.789	Intermediate Similarity	NPC107806
0.7886	Intermediate Similarity	NPC475273
0.7886	Intermediate Similarity	NPC168849
0.787	Intermediate Similarity	NPC29952
0.7857	Intermediate Similarity	NPC476111
0.7857	Intermediate Similarity	NPC474550
0.7857	Intermediate Similarity	NPC475585
0.7857	Intermediate Similarity	NPC473577
0.7851	Intermediate Similarity	NPC222688
0.7845	Intermediate Similarity	NPC317687
0.7845	Intermediate Similarity	NPC470063
0.7845	Intermediate Similarity	NPC221144
0.7845	Intermediate Similarity	NPC170487
0.7845	Intermediate Similarity	NPC471933
0.7838	Intermediate Similarity	NPC475038
0.7838	Intermediate Similarity	NPC109195
0.7838	Intermediate Similarity	NPC474709
0.7833	Intermediate Similarity	NPC17938
0.7833	Intermediate Similarity	NPC4548
0.7826	Intermediate Similarity	NPC5103
0.7826	Intermediate Similarity	NPC257240
0.7818	Intermediate Similarity	NPC470074
0.7818	Intermediate Similarity	NPC474718
0.7818	Intermediate Similarity	NPC47024
0.7815	Intermediate Similarity	NPC475372
0.7815	Intermediate Similarity	NPC470420
0.7812	Intermediate Similarity	NPC68282
0.7807	Intermediate Similarity	NPC189075
0.7807	Intermediate Similarity	NPC275539
0.7807	Intermediate Similarity	NPC94377
0.7805	Intermediate Similarity	NPC473635
0.7805	Intermediate Similarity	NPC217901
0.7805	Intermediate Similarity	NPC63186
0.7798	Intermediate Similarity	NPC100912
0.7798	Intermediate Similarity	NPC311241
0.7798	Intermediate Similarity	NPC475446
0.7798	Intermediate Similarity	NPC285513
0.7797	Intermediate Similarity	NPC270478
0.7797	Intermediate Similarity	NPC176840
0.7788	Intermediate Similarity	NPC472645
0.7788	Intermediate Similarity	NPC475290
0.7778	Intermediate Similarity	NPC471855
0.7778	Intermediate Similarity	NPC471204
0.7778	Intermediate Similarity	NPC473485
0.7778	Intermediate Similarity	NPC474508
0.7778	Intermediate Similarity	NPC469454
0.7778	Intermediate Similarity	NPC472926
0.7778	Intermediate Similarity	NPC469496
0.7778	Intermediate Similarity	NPC469463
0.7768	Intermediate Similarity	NPC120321
0.776	Intermediate Similarity	NPC471407
0.7759	Intermediate Similarity	NPC304180
0.7759	Intermediate Similarity	NPC179798
0.7759	Intermediate Similarity	NPC231589
0.7759	Intermediate Similarity	NPC214797
0.7759	Intermediate Similarity	NPC287311
0.7759	Intermediate Similarity	NPC118860
0.7759	Intermediate Similarity	NPC317107
0.775	Intermediate Similarity	NPC476529
0.775	Intermediate Similarity	NPC5292
0.775	Intermediate Similarity	NPC469380
0.775	Intermediate Similarity	NPC312536
0.775	Intermediate Similarity	NPC470186
0.775	Intermediate Similarity	NPC475775
0.7742	Intermediate Similarity	NPC298841
0.7739	Intermediate Similarity	NPC42662
0.7739	Intermediate Similarity	NPC304495
0.7739	Intermediate Similarity	NPC258543
0.7739	Intermediate Similarity	NPC241927
0.7731	Intermediate Similarity	NPC36754
0.7731	Intermediate Similarity	NPC473656
0.7731	Intermediate Similarity	NPC472934
0.7731	Intermediate Similarity	NPC471854

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 NPC474937 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1856
0.2-0.3	3694
0.3-0.4	2171
0.4-0.5	830
0.5-0.6	219
0.6-0.7	166
0.7-0.8	12
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
0.7826	Intermediate Similarity	NPD6371	Approved
0.7607	Intermediate Similarity	NPD6650	Approved
0.7607	Intermediate Similarity	NPD6649	Approved
0.7586	Intermediate Similarity	NPD6372	Approved
0.7586	Intermediate Similarity	NPD6373	Approved
0.7565	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.7478	Intermediate Similarity	NPD5739	Approved
0.7478	Intermediate Similarity	NPD6675	Approved
0.7478	Intermediate Similarity	NPD7128	Approved
0.7478	Intermediate Similarity	NPD6402	Approved
0.7458	Intermediate Similarity	NPD8130	Phase 1
0.7414	Intermediate Similarity	NPD5697	Approved
0.7411	Intermediate Similarity	NPD7638	Approved
0.7395	Intermediate Similarity	NPD6882	Approved
0.7373	Intermediate Similarity	NPD7290	Approved
0.7373	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD7102	Approved
0.7373	Intermediate Similarity	NPD6883	Approved
0.735	Intermediate Similarity	NPD7320	Approved
0.7345	Intermediate Similarity	NPD7639	Approved
0.7345	Intermediate Similarity	NPD7640	Approved
0.7328	Intermediate Similarity	NPD6008	Approved
0.7311	Intermediate Similarity	NPD6847	Approved
0.7311	Intermediate Similarity	NPD6617	Approved
0.7311	Intermediate Similarity	NPD6869	Approved
0.7295	Intermediate Similarity	NPD7115	Discovery
0.7288	Intermediate Similarity	NPD6013	Approved
0.7288	Intermediate Similarity	NPD6014	Approved
0.7288	Intermediate Similarity	NPD6012	Approved
0.7265	Intermediate Similarity	NPD5701	Approved
0.7258	Intermediate Similarity	NPD6319	Approved
0.7222	Intermediate Similarity	NPD7604	Phase 2
0.7203	Intermediate Similarity	NPD6011	Approved
0.719	Intermediate Similarity	NPD4632	Approved
0.7168	Intermediate Similarity	NPD6084	Phase 2
0.7168	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7507	Approved
0.7107	Intermediate Similarity	NPD6053	Discontinued
0.7105	Intermediate Similarity	NPD5696	Approved
0.7069	Intermediate Similarity	NPD5211	Phase 2
0.7059	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6686	Approved
0.7043	Intermediate Similarity	NPD5286	Approved
0.7043	Intermediate Similarity	NPD5285	Approved
0.7043	Intermediate Similarity	NPD4696	Approved
0.7031	Intermediate Similarity	NPD7492	Approved
0.7025	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4755	Approved
0.7018	Intermediate Similarity	NPD7902	Approved
0.7016	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD1695	Approved
0.7	Intermediate Similarity	NPD7736	Approved
0.6991	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6054	Approved
0.6983	Remote Similarity	NPD5344	Discontinued
0.6977	Remote Similarity	NPD6616	Approved
0.6964	Remote Similarity	NPD6399	Phase 3
0.6957	Remote Similarity	NPD4225	Approved
0.6949	Remote Similarity	NPD5141	Approved
0.6947	Remote Similarity	NPD7319	Approved
0.6937	Remote Similarity	NPD46	Approved
0.6937	Remote Similarity	NPD6698	Approved
0.6935	Remote Similarity	NPD6274	Approved
0.6929	Remote Similarity	NPD5983	Phase 2
0.6923	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD4633	Approved
0.6923	Remote Similarity	NPD5226	Approved
0.6923	Remote Similarity	NPD7078	Approved
0.6923	Remote Similarity	NPD8293	Discontinued
0.6923	Remote Similarity	NPD5224	Approved
0.6905	Remote Similarity	NPD7100	Approved
0.6905	Remote Similarity	NPD7101	Approved
0.6903	Remote Similarity	NPD5282	Discontinued
0.6903	Remote Similarity	NPD7748	Approved
0.6897	Remote Similarity	NPD4700	Approved
0.6897	Remote Similarity	NPD6648	Approved
0.6875	Remote Similarity	NPD6370	Approved
0.6875	Remote Similarity	NPD5693	Phase 1
0.6864	Remote Similarity	NPD5174	Approved
0.6864	Remote Similarity	NPD5175	Approved
0.685	Remote Similarity	NPD6059	Approved
0.6846	Remote Similarity	NPD6336	Discontinued
0.6838	Remote Similarity	NPD5223	Approved
0.6825	Remote Similarity	NPD6335	Approved
0.6825	Remote Similarity	NPD7327	Approved
0.6825	Remote Similarity	NPD7328	Approved
0.6822	Remote Similarity	NPD8328	Phase 3
0.6822	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4634	Approved
0.6797	Remote Similarity	NPD6016	Approved
0.6797	Remote Similarity	NPD8033	Approved
0.6797	Remote Similarity	NPD6015	Approved
0.6789	Remote Similarity	NPD1694	Approved
0.6789	Remote Similarity	NPD1696	Phase 3
0.678	Remote Similarity	NPD7632	Discontinued
0.6777	Remote Similarity	NPD4730	Approved
0.6777	Remote Similarity	NPD4729	Approved
0.6772	Remote Similarity	NPD7516	Approved
0.6757	Remote Similarity	NPD6672	Approved
0.6757	Remote Similarity	NPD5737	Approved
0.6754	Remote Similarity	NPD7900	Approved
0.6754	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4767	Approved
0.675	Remote Similarity	NPD4768	Approved
0.6746	Remote Similarity	NPD6317	Approved
0.6744	Remote Similarity	NPD5988	Approved
0.6719	Remote Similarity	NPD8377	Approved
0.6719	Remote Similarity	NPD8294	Approved
0.6716	Remote Similarity	NPD7260	Phase 2
0.6696	Remote Similarity	NPD6673	Approved
0.6696	Remote Similarity	NPD5210	Approved
0.6696	Remote Similarity	NPD4629	Approved
0.6696	Remote Similarity	NPD6080	Approved
0.6696	Remote Similarity	NPD6904	Approved
0.6696	Remote Similarity	NPD4753	Phase 2
0.6693	Remote Similarity	NPD6314	Approved
0.6693	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.664	Remote Similarity	NPD8133	Approved
0.6639	Remote Similarity	NPD5128	Approved
0.6638	Remote Similarity	NPD5221	Approved
0.6638	Remote Similarity	NPD5222	Approved
0.6638	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4697	Phase 3
0.6637	Remote Similarity	NPD5785	Approved
0.6637	Remote Similarity	NPD7838	Discovery
0.6609	Remote Similarity	NPD6001	Approved
0.6583	Remote Similarity	NPD4754	Approved
0.6581	Remote Similarity	NPD5173	Approved
0.6579	Remote Similarity	NPD6079	Approved
0.6579	Remote Similarity	NPD5281	Approved
0.6579	Remote Similarity	NPD8034	Phase 2
0.6579	Remote Similarity	NPD6050	Approved
0.6579	Remote Similarity	NPD8035	Phase 2
0.6579	Remote Similarity	NPD7515	Phase 2
0.6579	Remote Similarity	NPD5284	Approved
0.6549	Remote Similarity	NPD5328	Approved
0.6538	Remote Similarity	NPD7503	Approved
0.6538	Remote Similarity	NPD6921	Approved
0.6535	Remote Similarity	NPD6868	Approved
0.6522	Remote Similarity	NPD4202	Approved
0.6518	Remote Similarity	NPD3573	Approved
0.6491	Remote Similarity	NPD5692	Phase 3
0.6486	Remote Similarity	NPD5329	Approved
0.6484	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5216	Approved
0.648	Remote Similarity	NPD5217	Approved
0.648	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5215	Approved
0.6452	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5694	Approved
0.6429	Remote Similarity	NPD6098	Approved
0.6429	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD5690	Phase 2
0.6429	Remote Similarity	NPD7146	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6423	Remote Similarity	NPD6412	Phase 2
0.6423	Remote Similarity	NPD6845	Suspended
0.6412	Remote Similarity	NPD8517	Approved
0.6412	Remote Similarity	NPD8513	Phase 3
0.6412	Remote Similarity	NPD8515	Approved
0.6412	Remote Similarity	NPD8516	Approved
0.64	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5135	Approved
0.64	Remote Similarity	NPD5169	Approved
0.6396	Remote Similarity	NPD4197	Approved
0.6387	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5778	Approved
0.6379	Remote Similarity	NPD5779	Approved
0.637	Remote Similarity	NPD6033	Approved
0.6349	Remote Similarity	NPD5127	Approved
0.6339	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4695	Discontinued
0.6316	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5959	Approved
0.6293	Remote Similarity	NPD7983	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