NPASS Compound

Structure

NPC475937 OpenBabel07101719132D 31 34 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 -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 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 0.1073 4.3007 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 -0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 24 1 0 0 0 0 11 16 1 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 26 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 15 25 1 6 0 0 0 17 19 1 0 0 0 0 17 25 1 6 0 0 0 18 23 1 1 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 6 0 0 0 20 23 1 0 0 0 0 20 27 2 0 0 0 0 21 28 2 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 23 29 1 1 0 0 0 24 31 1 6 0 0 0 25 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.25
Volume:	448.926
LogP:	3.471
LogD:	2.537
LogS:	-4.069
# Rotatable Bonds:	5
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	5.104
Fsp3:	0.76
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:	-4.702
MDCK Permeability:	1.4582330550183542e-05
Pgp-inhibitor:	0.9
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.855
Plasma Protein Binding (PPB):	63.36322784423828%
Volume Distribution (VD):	0.952
Pgp-substrate:	41.46609115600586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.761
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.45
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	3.714
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.466
Human Hepatotoxicity (H-HT):	0.73
Drug-inuced Liver Injury (DILI):	0.425
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.711
Carcinogencity:	0.17
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC475937

Natural Product ID:	NPC475937
*Common Name:**	UTWPUNYNNNYPEZ-ABNKIXKLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UTWPUNYNNNYPEZ-ABNKIXKLSA-N
Standard InCHI:	InChI=1S/C25H36O6/c1-7-13(2)21(28)31-24-10-15(4)25(30)17(19(24)22(24,5)6)9-16(12-26)11-23(29)18(25)8-14(3)20(23)27/h8-9,13,15,17-19,26,29-30H,7,10-12H2,1-6H3/t13?,15-,17+,18-,19-,23-,24+,25-/m1/s1
SMILES:	CCC(C)C(=O)OC12CC(C3(C(C1C2(C)C)C=C(CC4(C3C=C(C4=O)C)O)CO)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518887
PubChem CID:	168766
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
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	Leaves	Langevin, La Reunion, France	2009-Nov	PMID[25946116]
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
EC50	5
Others	10

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	6
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Inhibition	<	40.0	%	PMID[449865]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	<	40.0	%	PMID[449865]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	<	40.0	%	PMID[449865]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	289000.0	nM	PMID[449865]
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	116000.0	nM	PMID[449865]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.83	nmol	PMID[449864]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.2	/nmol	PMID[449864]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	129.0	nM	PMID[449865]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	56.0	nM	PMID[449865]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	899.0	n.a.	PMID[449865]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	2056.0	n.a.	PMID[449865]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	1200.0	nM	PMID[449865]
NPT338	Organism	Sindbis virus	Sindbis virus	EC50	>	289000.0	nM	PMID[449865]
NPT856	Organism	Semliki forest virus	Semliki forest virus	EC50	>	289000.0	nM	PMID[449865]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	240.0	n.a.	PMID[449865]

☑ 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 NPC475937 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	221
0.1-0.2	1382
0.2-0.3	4522
0.3-0.4	8017
0.4-0.5	13617
0.5-0.6	7588
0.6-0.7	5909
0.7-0.8	1294
0.8-0.85	37
0.85-0.9	31
0.9-0.95	51
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC158523
0.9902	High Similarity	NPC153036
0.9808	High Similarity	NPC71889
0.9714	High Similarity	NPC474872
0.9615	High Similarity	NPC474871
0.9615	High Similarity	NPC260786
0.9615	High Similarity	NPC96739
0.9615	High Similarity	NPC174471
0.9533	High Similarity	NPC153651
0.9524	High Similarity	NPC475391
0.9524	High Similarity	NPC89227
0.9524	High Similarity	NPC265499
0.9524	High Similarity	NPC170212
0.9524	High Similarity	NPC101825
0.9524	High Similarity	NPC215643
0.9524	High Similarity	NPC151216
0.9524	High Similarity	NPC17138
0.9524	High Similarity	NPC221511
0.9444	High Similarity	NPC471125
0.9444	High Similarity	NPC472397
0.9444	High Similarity	NPC472760
0.9444	High Similarity	NPC472758
0.9444	High Similarity	NPC171905
0.9434	High Similarity	NPC474937
0.9434	High Similarity	NPC477091
0.9358	High Similarity	NPC275696
0.9358	High Similarity	NPC5989
0.9358	High Similarity	NPC471108
0.9358	High Similarity	NPC255081
0.9358	High Similarity	NPC22628
0.9358	High Similarity	NPC180640
0.9358	High Similarity	NPC5991
0.9352	High Similarity	NPC156252
0.9273	High Similarity	NPC471128
0.9273	High Similarity	NPC471126
0.9273	High Similarity	NPC157252
0.9273	High Similarity	NPC145182
0.9273	High Similarity	NPC185876
0.9273	High Similarity	NPC19336
0.9252	High Similarity	NPC472757
0.9189	High Similarity	NPC472401
0.9189	High Similarity	NPC52839
0.9167	High Similarity	NPC472400
0.9107	High Similarity	NPC19464
0.9083	High Similarity	NPC471127
0.9083	High Similarity	NPC234858
0.9083	High Similarity	NPC154363
0.9027	High Similarity	NPC472399
0.9	High Similarity	NPC10721
0.8947	High Similarity	NPC145238
0.8938	High Similarity	NPC257017
0.8938	High Similarity	NPC162009
0.8879	High Similarity	NPC163004
0.8839	High Similarity	NPC236918
0.8839	High Similarity	NPC156745
0.8761	High Similarity	NPC475885
0.8761	High Similarity	NPC472759
0.8761	High Similarity	NPC329080
0.875	High Similarity	NPC146280
0.875	High Similarity	NPC124676
0.8707	High Similarity	NPC222307
0.8559	High Similarity	NPC270109
0.8403	Intermediate Similarity	NPC236999
0.8305	Intermediate Similarity	NPC473919
0.8305	Intermediate Similarity	NPC473709
0.8302	Intermediate Similarity	NPC470074
0.8226	Intermediate Similarity	NPC243902
0.822	Intermediate Similarity	NPC473802
0.8167	Intermediate Similarity	NPC471940
0.8142	Intermediate Similarity	NPC71348
0.8136	Intermediate Similarity	NPC222688
0.8108	Intermediate Similarity	NPC322903
0.8087	Intermediate Similarity	NPC179626
0.8087	Intermediate Similarity	NPC270958
0.8083	Intermediate Similarity	NPC471939
0.8073	Intermediate Similarity	NPC478057
0.807	Intermediate Similarity	NPC202889
0.807	Intermediate Similarity	NPC474271
0.8049	Intermediate Similarity	NPC189393
0.8049	Intermediate Similarity	NPC90814
0.8036	Intermediate Similarity	NPC273433
0.8034	Intermediate Similarity	NPC472667
0.8034	Intermediate Similarity	NPC472933
0.8	Intermediate Similarity	NPC72255
0.7984	Intermediate Similarity	NPC476111
0.7982	Intermediate Similarity	NPC136289
0.7982	Intermediate Similarity	NPC118405
0.7982	Intermediate Similarity	NPC162973
0.7982	Intermediate Similarity	NPC476081
0.7965	Intermediate Similarity	NPC257240
0.7965	Intermediate Similarity	NPC5103
0.7963	Intermediate Similarity	NPC476274
0.7963	Intermediate Similarity	NPC474718
0.7963	Intermediate Similarity	NPC306856
0.7949	Intermediate Similarity	NPC118638
0.7946	Intermediate Similarity	NPC476479
0.7931	Intermediate Similarity	NPC148458
0.7913	Intermediate Similarity	NPC472926
0.7913	Intermediate Similarity	NPC25909
0.7913	Intermediate Similarity	NPC469454
0.7913	Intermediate Similarity	NPC469463
0.7913	Intermediate Similarity	NPC469496
0.7913	Intermediate Similarity	NPC962
0.7895	Intermediate Similarity	NPC118860
0.7895	Intermediate Similarity	NPC317107
0.7895	Intermediate Similarity	NPC214797
0.7895	Intermediate Similarity	NPC231589
0.789	Intermediate Similarity	NPC471412
0.789	Intermediate Similarity	NPC115862
0.789	Intermediate Similarity	NPC81530
0.789	Intermediate Similarity	NPC476223
0.789	Intermediate Similarity	NPC224720
0.789	Intermediate Similarity	NPC476240
0.7876	Intermediate Similarity	NPC241927
0.7876	Intermediate Similarity	NPC258543
0.7869	Intermediate Similarity	NPC473253
0.7863	Intermediate Similarity	NPC472927
0.7863	Intermediate Similarity	NPC471854
0.7863	Intermediate Similarity	NPC472934
0.7857	Intermediate Similarity	NPC472925
0.7857	Intermediate Similarity	NPC67321
0.7857	Intermediate Similarity	NPC187435
0.784	Intermediate Similarity	NPC469674
0.784	Intermediate Similarity	NPC469673
0.7838	Intermediate Similarity	NPC118911
0.783	Intermediate Similarity	NPC181393
0.783	Intermediate Similarity	NPC217624
0.7826	Intermediate Similarity	NPC76550
0.7826	Intermediate Similarity	NPC123855
0.7826	Intermediate Similarity	NPC234042
0.7826	Intermediate Similarity	NPC152117
0.7826	Intermediate Similarity	NPC472002
0.7826	Intermediate Similarity	NPC170487
0.7826	Intermediate Similarity	NPC317687
0.7823	Intermediate Similarity	NPC196921
0.7823	Intermediate Similarity	NPC220757
0.7818	Intermediate Similarity	NPC475038
0.7818	Intermediate Similarity	NPC119601
0.7818	Intermediate Similarity	NPC470840
0.7818	Intermediate Similarity	NPC109195
0.7818	Intermediate Similarity	NPC22388
0.7818	Intermediate Similarity	NPC308726
0.7815	Intermediate Similarity	NPC109973
0.7815	Intermediate Similarity	NPC143755
0.7807	Intermediate Similarity	NPC477103
0.7807	Intermediate Similarity	NPC473036
0.7807	Intermediate Similarity	NPC272898
0.7798	Intermediate Similarity	NPC47024
0.7798	Intermediate Similarity	NPC327431
0.7798	Intermediate Similarity	NPC471041
0.7798	Intermediate Similarity	NPC472972
0.7798	Intermediate Similarity	NPC471413
0.7797	Intermediate Similarity	NPC251310
0.7788	Intermediate Similarity	NPC189075
0.7788	Intermediate Similarity	NPC29827
0.7788	Intermediate Similarity	NPC102843
0.7788	Intermediate Similarity	NPC275539
0.7787	Intermediate Similarity	NPC15095
0.7778	Intermediate Similarity	NPC176840
0.7778	Intermediate Similarity	NPC49492
0.7778	Intermediate Similarity	NPC266728
0.7778	Intermediate Similarity	NPC170131
0.7778	Intermediate Similarity	NPC476823
0.7769	Intermediate Similarity	NPC469789
0.7768	Intermediate Similarity	NPC179891
0.7768	Intermediate Similarity	NPC472645
0.7768	Intermediate Similarity	NPC257353
0.7768	Intermediate Similarity	NPC60315
0.776	Intermediate Similarity	NPC475139
0.776	Intermediate Similarity	NPC34963
0.776	Intermediate Similarity	NPC180902
0.7759	Intermediate Similarity	NPC108721
0.7759	Intermediate Similarity	NPC73300
0.7759	Intermediate Similarity	NPC159333
0.7759	Intermediate Similarity	NPC317210
0.7759	Intermediate Similarity	NPC194100
0.7759	Intermediate Similarity	NPC46269
0.7759	Intermediate Similarity	NPC250109
0.7759	Intermediate Similarity	NPC106395
0.7757	Intermediate Similarity	NPC134067
0.775	Intermediate Similarity	NPC310511
0.775	Intermediate Similarity	NPC67569
0.7748	Intermediate Similarity	NPC247957
0.7748	Intermediate Similarity	NPC476237
0.7748	Intermediate Similarity	NPC120321
0.7748	Intermediate Similarity	NPC475623
0.7748	Intermediate Similarity	NPC475334
0.7748	Intermediate Similarity	NPC249187
0.7748	Intermediate Similarity	NPC473694
0.7748	Intermediate Similarity	NPC95899
0.7742	Intermediate Similarity	NPC470880
0.7742	Intermediate Similarity	NPC35109
0.7742	Intermediate Similarity	NPC221414
0.7739	Intermediate Similarity	NPC473921
0.7739	Intermediate Similarity	NPC304180
0.7739	Intermediate Similarity	NPC179798
0.7739	Intermediate Similarity	NPC475668
0.7739	Intermediate Similarity	NPC475480
0.7739	Intermediate Similarity	NPC472928
0.7736	Intermediate Similarity	NPC477435

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 NPC475937 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1809
0.2-0.3	3735
0.3-0.4	2187
0.4-0.5	810
0.5-0.6	221
0.6-0.7	166
0.7-0.8	33
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
0.7788	Intermediate Similarity	NPD6899	Approved
0.7788	Intermediate Similarity	NPD6881	Approved
0.7768	Intermediate Similarity	NPD5739	Approved
0.7768	Intermediate Similarity	NPD6675	Approved
0.7768	Intermediate Similarity	NPD7128	Approved
0.7768	Intermediate Similarity	NPD6402	Approved
0.7739	Intermediate Similarity	NPD6649	Approved
0.7739	Intermediate Similarity	NPD6650	Approved
0.7719	Intermediate Similarity	NPD6372	Approved
0.7719	Intermediate Similarity	NPD6373	Approved
0.7699	Intermediate Similarity	NPD5697	Approved
0.7652	Intermediate Similarity	NPD7102	Approved
0.7652	Intermediate Similarity	NPD6883	Approved
0.7652	Intermediate Similarity	NPD7290	Approved
0.7632	Intermediate Similarity	NPD7320	Approved
0.7586	Intermediate Similarity	NPD6847	Approved
0.7586	Intermediate Similarity	NPD6869	Approved
0.7586	Intermediate Similarity	NPD8130	Phase 1
0.7586	Intermediate Similarity	NPD6617	Approved
0.7565	Intermediate Similarity	NPD6012	Approved
0.7565	Intermediate Similarity	NPD6013	Approved
0.7565	Intermediate Similarity	NPD6014	Approved
0.7544	Intermediate Similarity	NPD5701	Approved
0.7521	Intermediate Similarity	NPD8297	Approved
0.7521	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.748	Intermediate Similarity	NPD7604	Phase 2
0.7478	Intermediate Similarity	NPD6011	Approved
0.7477	Intermediate Similarity	NPD7639	Approved
0.7477	Intermediate Similarity	NPD7640	Approved
0.7458	Intermediate Similarity	NPD4632	Approved
0.7456	Intermediate Similarity	NPD6008	Approved
0.7455	Intermediate Similarity	NPD6083	Phase 2
0.7455	Intermediate Similarity	NPD6084	Phase 2
0.7417	Intermediate Similarity	NPD7115	Discovery
0.7387	Intermediate Similarity	NPD7638	Approved
0.7377	Intermediate Similarity	NPD6319	Approved
0.7368	Intermediate Similarity	NPD5141	Approved
0.7321	Intermediate Similarity	NPD5286	Approved
0.7321	Intermediate Similarity	NPD4696	Approved
0.7321	Intermediate Similarity	NPD5285	Approved
0.7297	Intermediate Similarity	NPD4755	Approved
0.7288	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7492	Approved
0.7273	Intermediate Similarity	NPD6009	Approved
0.7273	Intermediate Similarity	NPD5695	Phase 3
0.7238	Intermediate Similarity	NPD1696	Phase 3
0.7236	Intermediate Similarity	NPD6054	Approved
0.7232	Intermediate Similarity	NPD5696	Approved
0.7222	Intermediate Similarity	NPD6616	Approved
0.7193	Intermediate Similarity	NPD5224	Approved
0.7193	Intermediate Similarity	NPD5225	Approved
0.7193	Intermediate Similarity	NPD4633	Approved
0.7193	Intermediate Similarity	NPD5226	Approved
0.719	Intermediate Similarity	NPD6274	Approved
0.7177	Intermediate Similarity	NPD5983	Phase 2
0.7168	Intermediate Similarity	NPD4700	Approved
0.7165	Intermediate Similarity	NPD7078	Approved
0.7154	Intermediate Similarity	NPD7100	Approved
0.7154	Intermediate Similarity	NPD7101	Approved
0.713	Intermediate Similarity	NPD5174	Approved
0.713	Intermediate Similarity	NPD5175	Approved
0.712	Intermediate Similarity	NPD6370	Approved
0.7119	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7736	Approved
0.7105	Intermediate Similarity	NPD5223	Approved
0.7105	Intermediate Similarity	NPD5344	Discontinued
0.7097	Intermediate Similarity	NPD6059	Approved
0.7094	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6399	Phase 3
0.7087	Intermediate Similarity	NPD6336	Discontinued
0.7083	Intermediate Similarity	NPD6053	Discontinued
0.708	Intermediate Similarity	NPD4225	Approved
0.7073	Intermediate Similarity	NPD6335	Approved
0.7059	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4634	Approved
0.704	Intermediate Similarity	NPD6016	Approved
0.704	Intermediate Similarity	NPD6015	Approved
0.7034	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8293	Discontinued
0.7027	Intermediate Similarity	NPD5282	Discontinued
0.6992	Remote Similarity	NPD6317	Approved
0.6991	Remote Similarity	NPD7902	Approved
0.6984	Remote Similarity	NPD5988	Approved
0.6972	Remote Similarity	NPD4753	Phase 2
0.6964	Remote Similarity	NPD5210	Approved
0.6964	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4629	Approved
0.6953	Remote Similarity	NPD7507	Approved
0.6935	Remote Similarity	NPD6313	Approved
0.6935	Remote Similarity	NPD6314	Approved
0.6905	Remote Similarity	NPD6909	Approved
0.6905	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6908	Approved
0.6903	Remote Similarity	NPD5221	Approved
0.6903	Remote Similarity	NPD5222	Approved
0.6903	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4697	Phase 3
0.6897	Remote Similarity	NPD7632	Discontinued
0.6891	Remote Similarity	NPD5128	Approved
0.6891	Remote Similarity	NPD6686	Approved
0.6891	Remote Similarity	NPD4730	Approved
0.6891	Remote Similarity	NPD4729	Approved
0.6881	Remote Similarity	NPD6672	Approved
0.6881	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD7748	Approved
0.687	Remote Similarity	NPD6648	Approved
0.6864	Remote Similarity	NPD4767	Approved
0.6864	Remote Similarity	NPD4768	Approved
0.6847	Remote Similarity	NPD7515	Phase 2
0.6847	Remote Similarity	NPD6079	Approved
0.6842	Remote Similarity	NPD5173	Approved
0.6838	Remote Similarity	NPD4754	Approved
0.6818	Remote Similarity	NPD6673	Approved
0.6818	Remote Similarity	NPD5328	Approved
0.6818	Remote Similarity	NPD1695	Approved
0.6818	Remote Similarity	NPD6904	Approved
0.6818	Remote Similarity	NPD6080	Approved
0.6807	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8328	Phase 3
0.6794	Remote Similarity	NPD7319	Approved
0.6786	Remote Similarity	NPD4202	Approved
0.6786	Remote Similarity	NPD5779	Approved
0.6786	Remote Similarity	NPD5778	Approved
0.6777	Remote Similarity	NPD5247	Approved
0.6777	Remote Similarity	NPD5250	Approved
0.6777	Remote Similarity	NPD5248	Approved
0.6777	Remote Similarity	NPD5251	Approved
0.6777	Remote Similarity	NPD5249	Phase 3
0.6774	Remote Similarity	NPD6868	Approved
0.6757	Remote Similarity	NPD46	Approved
0.6757	Remote Similarity	NPD6698	Approved
0.6757	Remote Similarity	NPD5785	Approved
0.6726	Remote Similarity	NPD7900	Approved
0.6726	Remote Similarity	NPD6001	Approved
0.6726	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5215	Approved
0.6721	Remote Similarity	NPD5216	Approved
0.6721	Remote Similarity	NPD5217	Approved
0.6697	Remote Similarity	NPD3618	Phase 1
0.6696	Remote Similarity	NPD6050	Approved
0.6696	Remote Similarity	NPD5281	Approved
0.6696	Remote Similarity	NPD5284	Approved
0.6696	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6639	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5135	Approved
0.6639	Remote Similarity	NPD5169	Approved
0.6636	Remote Similarity	NPD3573	Approved
0.6636	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7516	Approved
0.6607	Remote Similarity	NPD5692	Phase 3
0.6606	Remote Similarity	NPD5329	Approved
0.6606	Remote Similarity	NPD5363	Approved
0.6606	Remote Similarity	NPD1694	Approved
0.6591	Remote Similarity	NPD6033	Approved
0.6585	Remote Similarity	NPD5127	Approved
0.6574	Remote Similarity	NPD7154	Phase 3
0.6574	Remote Similarity	NPD5362	Discontinued
0.6549	Remote Similarity	NPD8034	Phase 2
0.6549	Remote Similarity	NPD7637	Suspended
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	NPD6684	Approved
0.6545	Remote Similarity	NPD7521	Approved
0.6545	Remote Similarity	NPD5690	Phase 2
0.6545	Remote Similarity	NPD7334	Approved
0.6545	Remote Similarity	NPD5330	Approved
0.6545	Remote Similarity	NPD6409	Approved
0.6514	Remote Similarity	NPD4786	Approved
0.6514	Remote Similarity	NPD4197	Approved
0.6512	Remote Similarity	NPD8033	Approved
0.6457	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4695	Discontinued
0.6444	Remote Similarity	NPD7260	Phase 2
0.6434	Remote Similarity	NPD8377	Approved
0.6434	Remote Similarity	NPD8294	Approved
0.6429	Remote Similarity	NPD5167	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6903	Approved
0.6423	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5959	Approved
0.6404	Remote Similarity	NPD6411	Approved
0.6404	Remote Similarity	NPD7983	Approved
0.6396	Remote Similarity	NPD4519	Discontinued
0.6396	Remote Similarity	NPD5280	Approved
0.6396	Remote Similarity	NPD5279	Phase 3
0.6396	Remote Similarity	NPD4623	Approved
0.6396	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5786	Approved
0.6396	Remote Similarity	NPD4694	Approved
0.6385	Remote Similarity	NPD8378	Approved
0.6385	Remote Similarity	NPD8296	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