NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	292.2
Volume:	327.153
LogP:	3.879
LogD:	2.627
LogS:	-3.842
# Rotatable Bonds:	11
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	2.813
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.979
MDCK Permeability:	3.0989038350526243e-05
Pgp-inhibitor:	0.113
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.098
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	97.29517364501953%
Volume Distribution (VD):	0.448
Pgp-substrate:	0.5602635145187378%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.728
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.184
CYP2D6-substrate:	0.481
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	2.495
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.315
Skin Sensitization:	0.801
Carcinogencity:	0.509
Eye Corrosion:	0.005
Eye Irritation:	0.06
Respiratory Toxicity:	0.304

Download Data

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

Natural Product: NPC476614

Natural Product ID:	NPC476614
*Common Name:**	12-Oxophytodienoic acid
IUPAC Name:	8-[4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoic acid
Synonyms:	Cis-12-Oxophytodienoic Acid
Standard InCHIKey:	PMTMAFAPLCGXGK-CLTKARDFSA-N
Standard InCHI:	InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-
SMILES:	CC/C=C\CC1C(C=CC1=O)CCCCCCCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10334541
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3130	Organism	Lepidium sativum	Lepidium sativum	Inhibition	=	50	%	PMID[15844959]

☑ 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 NPC476614 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	171
0.1-0.2	1301
0.2-0.3	8150
0.3-0.4	16296
0.4-0.5	8455
0.5-0.6	5772
0.6-0.7	2206
0.7-0.8	317
0.8-0.85	18
0.85-0.9	8
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC174560
0.875	High Similarity	NPC192006
0.875	High Similarity	NPC125312
0.8696	High Similarity	NPC29328
0.8676	High Similarity	NPC67608
0.8438	Intermediate Similarity	NPC106851
0.8438	Intermediate Similarity	NPC274927
0.8429	Intermediate Similarity	NPC288667
0.8382	Intermediate Similarity	NPC60120
0.8382	Intermediate Similarity	NPC476626
0.8333	Intermediate Similarity	NPC322457
0.8308	Intermediate Similarity	NPC235242
0.8308	Intermediate Similarity	NPC174447
0.8308	Intermediate Similarity	NPC122521
0.8308	Intermediate Similarity	NPC251042
0.8286	Intermediate Similarity	NPC318766
0.8235	Intermediate Similarity	NPC197089
0.8182	Intermediate Similarity	NPC40082
0.8169	Intermediate Similarity	NPC67076
0.8169	Intermediate Similarity	NPC319163
0.8108	Intermediate Similarity	NPC472014
0.8088	Intermediate Similarity	NPC474329
0.8088	Intermediate Similarity	NPC474304
0.8	Intermediate Similarity	NPC169095
0.8	Intermediate Similarity	NPC74410
0.7975	Intermediate Similarity	NPC125290
0.7973	Intermediate Similarity	NPC180886
0.7973	Intermediate Similarity	NPC279537
0.7971	Intermediate Similarity	NPC142423
0.7971	Intermediate Similarity	NPC308294
0.7969	Intermediate Similarity	NPC477201
0.7895	Intermediate Similarity	NPC164308
0.7895	Intermediate Similarity	NPC476624
0.7895	Intermediate Similarity	NPC472013
0.7887	Intermediate Similarity	NPC469914
0.7867	Intermediate Similarity	NPC165711
0.7867	Intermediate Similarity	NPC97377
0.7838	Intermediate Similarity	NPC251435
0.7821	Intermediate Similarity	NPC238991
0.7821	Intermediate Similarity	NPC302661
0.7808	Intermediate Similarity	NPC472956
0.7808	Intermediate Similarity	NPC321017
0.7778	Intermediate Similarity	NPC36061
0.7778	Intermediate Similarity	NPC294548
0.7778	Intermediate Similarity	NPC67183
0.7778	Intermediate Similarity	NPC1813
0.7778	Intermediate Similarity	NPC139029
0.7763	Intermediate Similarity	NPC476627
0.775	Intermediate Similarity	NPC29447
0.7733	Intermediate Similarity	NPC266159
0.7733	Intermediate Similarity	NPC472967
0.7733	Intermediate Similarity	NPC473223
0.7727	Intermediate Similarity	NPC329819
0.7722	Intermediate Similarity	NPC65350
0.7714	Intermediate Similarity	NPC154728
0.7714	Intermediate Similarity	NPC126899
0.7714	Intermediate Similarity	NPC304665
0.7703	Intermediate Similarity	NPC55527
0.7692	Intermediate Similarity	NPC325031
0.7692	Intermediate Similarity	NPC325977
0.7692	Intermediate Similarity	NPC278459
0.7692	Intermediate Similarity	NPC90055
0.7692	Intermediate Similarity	NPC477372
0.7681	Intermediate Similarity	NPC234767
0.7662	Intermediate Similarity	NPC469617
0.7662	Intermediate Similarity	NPC113363
0.7656	Intermediate Similarity	NPC424
0.7656	Intermediate Similarity	NPC25417
0.7656	Intermediate Similarity	NPC88966
0.7656	Intermediate Similarity	NPC6095
0.7656	Intermediate Similarity	NPC261831
0.7656	Intermediate Similarity	NPC32467
0.7656	Intermediate Similarity	NPC87564
0.7656	Intermediate Similarity	NPC290563
0.7656	Intermediate Similarity	NPC85813
0.7656	Intermediate Similarity	NPC281972
0.7656	Intermediate Similarity	NPC154245
0.7619	Intermediate Similarity	NPC281245
0.76	Intermediate Similarity	NPC201027
0.76	Intermediate Similarity	NPC244166
0.76	Intermediate Similarity	NPC474011
0.7595	Intermediate Similarity	NPC320514
0.7576	Intermediate Similarity	NPC281230
0.7576	Intermediate Similarity	NPC192843
0.7568	Intermediate Similarity	NPC35656
0.7568	Intermediate Similarity	NPC300940
0.7564	Intermediate Similarity	NPC26139
0.7534	Intermediate Similarity	NPC18543
0.7532	Intermediate Similarity	NPC19443
0.7532	Intermediate Similarity	NPC198240
0.7532	Intermediate Similarity	NPC59436
0.7532	Intermediate Similarity	NPC128276
0.7531	Intermediate Similarity	NPC476628
0.7531	Intermediate Similarity	NPC474537
0.7531	Intermediate Similarity	NPC142649
0.75	Intermediate Similarity	NPC229252
0.75	Intermediate Similarity	NPC321062
0.75	Intermediate Similarity	NPC49019
0.75	Intermediate Similarity	NPC469646
0.75	Intermediate Similarity	NPC474141
0.75	Intermediate Similarity	NPC102197
0.75	Intermediate Similarity	NPC143857
0.75	Intermediate Similarity	NPC40353
0.75	Intermediate Similarity	NPC70387
0.75	Intermediate Similarity	NPC266119
0.75	Intermediate Similarity	NPC476629
0.7468	Intermediate Similarity	NPC47031
0.7468	Intermediate Similarity	NPC471898
0.7467	Intermediate Similarity	NPC227396
0.7467	Intermediate Similarity	NPC476046
0.7467	Intermediate Similarity	NPC237591
0.7467	Intermediate Similarity	NPC183503
0.7467	Intermediate Similarity	NPC283908
0.7467	Intermediate Similarity	NPC241854
0.7467	Intermediate Similarity	NPC161923
0.7467	Intermediate Similarity	NPC3753
0.7467	Intermediate Similarity	NPC251970
0.7467	Intermediate Similarity	NPC472966
0.7467	Intermediate Similarity	NPC7382
0.7467	Intermediate Similarity	NPC103958
0.7465	Intermediate Similarity	NPC166791
0.7465	Intermediate Similarity	NPC322035
0.7465	Intermediate Similarity	NPC100719
0.7463	Intermediate Similarity	NPC34416
0.746	Intermediate Similarity	NPC48162
0.7439	Intermediate Similarity	NPC6247
0.7439	Intermediate Similarity	NPC472869
0.7436	Intermediate Similarity	NPC477371
0.7432	Intermediate Similarity	NPC160817
0.7432	Intermediate Similarity	NPC469737
0.7424	Intermediate Similarity	NPC18951
0.7424	Intermediate Similarity	NPC179764
0.7424	Intermediate Similarity	NPC187777
0.7407	Intermediate Similarity	NPC248758
0.7407	Intermediate Similarity	NPC19849
0.7407	Intermediate Similarity	NPC472865
0.7407	Intermediate Similarity	NPC472864
0.7407	Intermediate Similarity	NPC165287
0.7403	Intermediate Similarity	NPC276769
0.7403	Intermediate Similarity	NPC195785
0.7403	Intermediate Similarity	NPC61952
0.7403	Intermediate Similarity	NPC57744
0.7403	Intermediate Similarity	NPC15975
0.7397	Intermediate Similarity	NPC199557
0.7397	Intermediate Similarity	NPC143396
0.7397	Intermediate Similarity	NPC296522
0.7397	Intermediate Similarity	NPC144511
0.7397	Intermediate Similarity	NPC265574
0.7397	Intermediate Similarity	NPC250928
0.7397	Intermediate Similarity	NPC10758
0.7391	Intermediate Similarity	NPC97322
0.7385	Intermediate Similarity	NPC322461
0.7381	Intermediate Similarity	NPC52198
0.7381	Intermediate Similarity	NPC117405
0.7381	Intermediate Similarity	NPC262043
0.7375	Intermediate Similarity	NPC7414
0.7375	Intermediate Similarity	NPC85772
0.7368	Intermediate Similarity	NPC68624
0.7368	Intermediate Similarity	NPC476346
0.7368	Intermediate Similarity	NPC279666
0.7368	Intermediate Similarity	NPC329852
0.7368	Intermediate Similarity	NPC472327
0.7368	Intermediate Similarity	NPC476795
0.7368	Intermediate Similarity	NPC77501
0.7368	Intermediate Similarity	NPC192540
0.7368	Intermediate Similarity	NPC476844
0.7361	Intermediate Similarity	NPC278895
0.7353	Intermediate Similarity	NPC329550
0.7353	Intermediate Similarity	NPC259261
0.7344	Intermediate Similarity	NPC92114
0.7342	Intermediate Similarity	NPC476809
0.7342	Intermediate Similarity	NPC271104
0.7333	Intermediate Similarity	NPC472813
0.7333	Intermediate Similarity	NPC275098
0.7333	Intermediate Similarity	NPC470237
0.7324	Intermediate Similarity	NPC61473
0.7317	Intermediate Similarity	NPC28887
0.7317	Intermediate Similarity	NPC261380
0.7313	Intermediate Similarity	NPC225929
0.7308	Intermediate Similarity	NPC189485
0.7308	Intermediate Similarity	NPC471409
0.7308	Intermediate Similarity	NPC218817
0.7308	Intermediate Similarity	NPC275494
0.7308	Intermediate Similarity	NPC267231
0.7308	Intermediate Similarity	NPC179028
0.7308	Intermediate Similarity	NPC475994
0.7308	Intermediate Similarity	NPC93763
0.7308	Intermediate Similarity	NPC11796
0.7308	Intermediate Similarity	NPC108816
0.7302	Intermediate Similarity	NPC224227
0.7297	Intermediate Similarity	NPC280256
0.7286	Intermediate Similarity	NPC477707
0.7286	Intermediate Similarity	NPC477830
0.7284	Intermediate Similarity	NPC39588
0.7284	Intermediate Similarity	NPC52609
0.7284	Intermediate Similarity	NPC470015
0.7284	Intermediate Similarity	NPC1761
0.7284	Intermediate Similarity	NPC105803
0.7284	Intermediate Similarity	NPC168188
0.7284	Intermediate Similarity	NPC470165

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 NPC476614 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	2116
0.2-0.3	3966
0.3-0.4	1969
0.4-0.5	572
0.5-0.6	270
0.6-0.7	94
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
0.7778	Intermediate Similarity	NPD3172	Approved
0.775	Intermediate Similarity	NPD5363	Approved
0.7714	Intermediate Similarity	NPD7331	Phase 2
0.7656	Intermediate Similarity	NPD3194	Approved
0.7656	Intermediate Similarity	NPD4266	Approved
0.7656	Intermediate Similarity	NPD3196	Approved
0.7656	Intermediate Similarity	NPD3195	Phase 2
0.7564	Intermediate Similarity	NPD5368	Approved
0.7532	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5369	Approved
0.7375	Intermediate Similarity	NPD4269	Approved
0.7375	Intermediate Similarity	NPD4270	Approved
0.7375	Intermediate Similarity	NPD6435	Approved
0.7324	Intermediate Similarity	NPD7341	Phase 2
0.7294	Intermediate Similarity	NPD5785	Approved
0.7284	Intermediate Similarity	NPD5362	Discontinued
0.7188	Intermediate Similarity	NPD29	Approved
0.7188	Intermediate Similarity	NPD28	Approved
0.7143	Intermediate Similarity	NPD3173	Approved
0.7125	Intermediate Similarity	NPD4252	Approved
0.7125	Intermediate Similarity	NPD4695	Discontinued
0.7073	Intermediate Similarity	NPD7154	Phase 3
0.7042	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5690	Phase 2
0.7024	Intermediate Similarity	NPD4519	Discontinued
0.7024	Intermediate Similarity	NPD5786	Approved
0.7024	Intermediate Similarity	NPD4623	Approved
0.7011	Intermediate Similarity	NPD5284	Approved
0.7011	Intermediate Similarity	NPD5281	Approved
0.6984	Remote Similarity	NPD622	Approved
0.6966	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4223	Phase 3
0.6951	Remote Similarity	NPD4221	Approved
0.6944	Remote Similarity	NPD3197	Phase 1
0.6914	Remote Similarity	NPD4820	Approved
0.6914	Remote Similarity	NPD4822	Approved
0.6914	Remote Similarity	NPD4819	Approved
0.6914	Remote Similarity	NPD4821	Approved
0.6875	Remote Similarity	NPD4268	Approved
0.6875	Remote Similarity	NPD4271	Approved
0.6829	Remote Similarity	NPD857	Phase 3
0.6786	Remote Similarity	NPD3133	Approved
0.6786	Remote Similarity	NPD3665	Phase 1
0.6786	Remote Similarity	NPD3666	Approved
0.6786	Remote Similarity	NPD4197	Approved
0.675	Remote Similarity	NPD4756	Discovery
0.6747	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5209	Approved
0.6744	Remote Similarity	NPD3573	Approved
0.6707	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5329	Approved
0.6706	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD4222	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD634	Phase 3
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD3174	Discontinued
0.6667	Remote Similarity	NPD4518	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6629	Remote Similarity	NPD6079	Approved
0.6629	Remote Similarity	NPD7515	Phase 2
0.6628	Remote Similarity	NPD6684	Approved
0.6628	Remote Similarity	NPD5280	Approved
0.6628	Remote Similarity	NPD3618	Phase 1
0.6628	Remote Similarity	NPD5205	Approved
0.6628	Remote Similarity	NPD4689	Approved
0.6628	Remote Similarity	NPD6409	Approved
0.6628	Remote Similarity	NPD7334	Approved
0.6628	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7521	Approved
0.6628	Remote Similarity	NPD4693	Phase 3
0.6628	Remote Similarity	NPD7146	Approved
0.6628	Remote Similarity	NPD4690	Approved
0.6628	Remote Similarity	NPD5279	Phase 3
0.6628	Remote Similarity	NPD4688	Approved
0.6628	Remote Similarity	NPD4138	Approved
0.6628	Remote Similarity	NPD4694	Approved
0.6628	Remote Similarity	NPD5330	Approved
0.6627	Remote Similarity	NPD4790	Discontinued
0.6623	Remote Similarity	NPD4691	Approved
0.6593	Remote Similarity	NPD5695	Phase 3
0.6591	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4195	Approved
0.6582	Remote Similarity	NPD4058	Approved
0.6548	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3667	Approved
0.6533	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5207	Approved
0.6494	Remote Similarity	NPD4137	Phase 3
0.6489	Remote Similarity	NPD2066	Phase 3
0.6484	Remote Similarity	NPD7748	Approved
0.6484	Remote Similarity	NPD5282	Discontinued
0.6477	Remote Similarity	NPD5208	Approved
0.6477	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6672	Approved
0.6477	Remote Similarity	NPD5737	Approved
0.6477	Remote Similarity	NPD6903	Approved
0.6463	Remote Similarity	NPD3732	Approved
0.6452	Remote Similarity	NPD6084	Phase 2
0.6452	Remote Similarity	NPD6083	Phase 2
0.6444	Remote Similarity	NPD5694	Approved
0.6413	Remote Similarity	NPD5210	Approved
0.6413	Remote Similarity	NPD4629	Approved
0.641	Remote Similarity	NPD4747	Approved
0.6406	Remote Similarity	NPD39	Approved
0.6404	Remote Similarity	NPD6101	Approved
0.6404	Remote Similarity	NPD5328	Approved
0.6404	Remote Similarity	NPD6904	Approved
0.6404	Remote Similarity	NPD4753	Phase 2
0.6404	Remote Similarity	NPD6673	Approved
0.6404	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6080	Approved
0.6395	Remote Similarity	NPD4786	Approved
0.6389	Remote Similarity	NPD3198	Approved
0.6383	Remote Similarity	NPD5696	Approved
0.6377	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD4687	Approved
0.6374	Remote Similarity	NPD6399	Phase 3
0.6344	Remote Similarity	NPD7614	Phase 1
0.6344	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD5222	Approved
0.6344	Remote Similarity	NPD5221	Approved
0.6333	Remote Similarity	NPD46	Approved
0.6333	Remote Similarity	NPD4096	Approved
0.6333	Remote Similarity	NPD6698	Approved
0.6333	Remote Similarity	NPD5692	Phase 3
0.6329	Remote Similarity	NPD5276	Approved
0.6324	Remote Similarity	NPD3186	Phase 1
0.6301	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8039	Approved
0.6277	Remote Similarity	NPD7902	Approved
0.6277	Remote Similarity	NPD5173	Approved
0.6264	Remote Similarity	NPD6411	Approved
0.6264	Remote Similarity	NPD5693	Phase 1
0.6264	Remote Similarity	NPD6050	Approved
0.6263	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD6098	Approved
0.625	Remote Similarity	NPD4249	Approved
0.6237	Remote Similarity	NPD1693	Approved
0.6222	Remote Similarity	NPD5370	Suspended
0.6222	Remote Similarity	NPD1695	Approved
0.6216	Remote Similarity	NPD4194	Approved
0.6216	Remote Similarity	NPD4193	Approved
0.6216	Remote Similarity	NPD4192	Approved
0.6216	Remote Similarity	NPD4191	Approved
0.62	Remote Similarity	NPD6011	Approved
0.62	Remote Similarity	NPD6881	Approved
0.62	Remote Similarity	NPD6899	Approved
0.6196	Remote Similarity	NPD5778	Approved
0.6196	Remote Similarity	NPD5779	Approved
0.6196	Remote Similarity	NPD4202	Approved
0.6184	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4250	Approved
0.618	Remote Similarity	NPD4251	Approved
0.6173	Remote Similarity	NPD5733	Approved
0.6146	Remote Similarity	NPD5286	Approved
0.6146	Remote Similarity	NPD5285	Approved
0.6146	Remote Similarity	NPD4696	Approved
0.6146	Remote Similarity	NPD6404	Discontinued
0.6139	Remote Similarity	NPD6012	Approved
0.6139	Remote Similarity	NPD6014	Approved
0.6139	Remote Similarity	NPD6013	Approved
0.6136	Remote Similarity	NPD1696	Phase 3
0.6136	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6001	Approved
0.6122	Remote Similarity	NPD1929	Approved
0.6122	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD1930	Approved
0.6122	Remote Similarity	NPD6647	Phase 2
0.6118	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD3704	Approved
0.6104	Remote Similarity	NPD4224	Phase 2
0.61	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD5326	Phase 3
0.6092	Remote Similarity	NPD4788	Approved
0.6087	Remote Similarity	NPD7983	Approved
0.6087	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5223	Approved
0.6078	Remote Similarity	NPD6371	Approved
0.6078	Remote Similarity	NPD7290	Approved
0.6078	Remote Similarity	NPD7102	Approved
0.6078	Remote Similarity	NPD6883	Approved
0.6064	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4139	Approved
0.6047	Remote Similarity	NPD4692	Approved
0.6044	Remote Similarity	NPD5346	Phase 2
0.6044	Remote Similarity	NPD5347	Phase 2
0.6027	Remote Similarity	NPD287	Approved
0.6023	Remote Similarity	NPD3668	Phase 3
0.6023	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5133	Approved
0.602	Remote Similarity	NPD5211	Phase 2
0.602	Remote Similarity	NPD5224	Approved
0.602	Remote Similarity	NPD4633	Approved
0.602	Remote Similarity	NPD5225	Approved
0.602	Remote Similarity	NPD5226	Approved
0.602	Remote Similarity	NPD5091	Approved
0.6019	Remote Similarity	NPD6650	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