NPASS Compound

Structure

NPC168050 OpenBabel07101718192D 23 25 0 0 0 0 0 0 0 0999 V2000 -1.1248 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 -0.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 11 2 0 0 0 0 8 12 2 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 12 23 1 0 0 0 0 13 14 2 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 15 20 2 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.12
Volume:	325.58
LogP:	3.016
LogD:	2.989
LogS:	-4.296
# Rotatable Bonds:	0
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	3.103
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.984
MDCK Permeability:	3.52472961822059e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.905
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	90.1239013671875%
Volume Distribution (VD):	1.135
Pgp-substrate:	6.5793023109436035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.89
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.876
CYP2C9-substrate:	0.698
CYP2D6-inhibitor:	0.417
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.353
CYP3A4-substrate:	0.9

ADMET: Excretion

Clearance (CL):	1.93
Half-life (T1/2):	0.41

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.847
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.311
Rat Oral Acute Toxicity:	0.708
Maximum Recommended Daily Dose:	0.696
Skin Sensitization:	0.875
Carcinogencity:	0.778
Eye Corrosion:	0.004
Eye Irritation:	0.328
Respiratory Toxicity:	0.846

Download Data

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

Natural Product: NPC168050

Natural Product ID:	NPC168050
*Common Name:**	Emorydone
IUPAC Name:	6-chromen-2-ylidene-2,2,4,4-tetramethylcyclohexane-1,3,5-trione
Synonyms:	Emorydone
Standard InCHIKey:	KJTSEOZFKJNYBZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O4/c1-18(2)15(20)14(16(21)19(3,4)17(18)22)13-10-9-11-7-5-6-8-12(11)23-13/h5-10H,1-4H3
SMILES:	CC1(C)C(=O)C(=C2C=Cc3ccccc3O2)C(=O)C(C)(C)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445520
PubChem CID:	10063979
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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
NPO26504	Psorothamnus junceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000028]
NPO26504	Psorothamnus junceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26504	Psorothamnus junceus	Species	Fabaceae	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
GI50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI50	=	3.0	ug.mL-1	PMID[510950]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	3.0	ug.mL-1	PMID[510950]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	4.0	ug.mL-1	PMID[510950]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	=	3.0	ug.mL-1	PMID[510950]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	=	1.0	ug.mL-1	PMID[510950]

☑ 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 NPC168050 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	356
0.1-0.2	1584
0.2-0.3	3839
0.3-0.4	11089
0.4-0.5	7958
0.5-0.6	6289
0.6-0.7	10006
0.7-0.8	1569
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.906	High Similarity	NPC43435
0.8504	High Similarity	NPC2989
0.843	Intermediate Similarity	NPC54243
0.8347	Intermediate Similarity	NPC32298
0.8347	Intermediate Similarity	NPC152159
0.832	Intermediate Similarity	NPC89630
0.8279	Intermediate Similarity	NPC35744
0.8211	Intermediate Similarity	NPC474874
0.8203	Intermediate Similarity	NPC125887
0.812	Intermediate Similarity	NPC21797
0.812	Intermediate Similarity	NPC194847
0.811	Intermediate Similarity	NPC2771
0.808	Intermediate Similarity	NPC314329
0.8047	Intermediate Similarity	NPC237868
0.8033	Intermediate Similarity	NPC33717
0.8031	Intermediate Similarity	NPC75432
0.8031	Intermediate Similarity	NPC56332
0.8017	Intermediate Similarity	NPC114144
0.8016	Intermediate Similarity	NPC49441
0.8	Intermediate Similarity	NPC307883
0.8	Intermediate Similarity	NPC238309
0.7984	Intermediate Similarity	NPC264976
0.7984	Intermediate Similarity	NPC298884
0.7984	Intermediate Similarity	NPC201284
0.7984	Intermediate Similarity	NPC41721
0.7967	Intermediate Similarity	NPC469954
0.7953	Intermediate Similarity	NPC93730
0.7951	Intermediate Similarity	NPC51345
0.7934	Intermediate Similarity	NPC90903
0.7929	Intermediate Similarity	NPC250331
0.7926	Intermediate Similarity	NPC471542
0.7926	Intermediate Similarity	NPC161196
0.7923	Intermediate Similarity	NPC157212
0.792	Intermediate Similarity	NPC193193
0.792	Intermediate Similarity	NPC246214
0.792	Intermediate Similarity	NPC31314
0.792	Intermediate Similarity	NPC470092
0.7917	Intermediate Similarity	NPC233238
0.7903	Intermediate Similarity	NPC293424
0.7899	Intermediate Similarity	NPC259554
0.7895	Intermediate Similarity	NPC473655
0.7895	Intermediate Similarity	NPC101294
0.7895	Intermediate Similarity	NPC287533
0.7891	Intermediate Similarity	NPC229113
0.7891	Intermediate Similarity	NPC193805
0.7886	Intermediate Similarity	NPC19290
0.7883	Intermediate Similarity	NPC155552
0.7879	Intermediate Similarity	NPC301717
0.7863	Intermediate Similarity	NPC139891
0.7857	Intermediate Similarity	NPC474261
0.7852	Intermediate Similarity	NPC46869
0.7846	Intermediate Similarity	NPC95034
0.7846	Intermediate Similarity	NPC142087
0.7846	Intermediate Similarity	NPC37512
0.7846	Intermediate Similarity	NPC161322
0.7845	Intermediate Similarity	NPC298224
0.7842	Intermediate Similarity	NPC251372
0.7836	Intermediate Similarity	NPC477210
0.7829	Intermediate Similarity	NPC165556
0.7829	Intermediate Similarity	NPC470858
0.7823	Intermediate Similarity	NPC263754
0.7823	Intermediate Similarity	NPC183154
0.7823	Intermediate Similarity	NPC45104
0.782	Intermediate Similarity	NPC278556
0.782	Intermediate Similarity	NPC119985
0.782	Intermediate Similarity	NPC280476
0.7812	Intermediate Similarity	NPC472888
0.7812	Intermediate Similarity	NPC11799
0.7812	Intermediate Similarity	NPC141252
0.781	Intermediate Similarity	NPC476191
0.781	Intermediate Similarity	NPC17848
0.7803	Intermediate Similarity	NPC475102
0.7803	Intermediate Similarity	NPC282230
0.7803	Intermediate Similarity	NPC183348
0.7803	Intermediate Similarity	NPC228184
0.7797	Intermediate Similarity	NPC326801
0.7794	Intermediate Similarity	NPC254741
0.7787	Intermediate Similarity	NPC279916
0.7786	Intermediate Similarity	NPC201419
0.7786	Intermediate Similarity	NPC11700
0.7778	Intermediate Similarity	NPC61499
0.7778	Intermediate Similarity	NPC229128
0.7778	Intermediate Similarity	NPC230951
0.7778	Intermediate Similarity	NPC66705
0.7778	Intermediate Similarity	NPC38209
0.777	Intermediate Similarity	NPC22467
0.7769	Intermediate Similarity	NPC474264
0.7761	Intermediate Similarity	NPC54503
0.7761	Intermediate Similarity	NPC55147
0.7754	Intermediate Similarity	NPC96565
0.7754	Intermediate Similarity	NPC303633
0.7754	Intermediate Similarity	NPC216978
0.7754	Intermediate Similarity	NPC220062
0.7754	Intermediate Similarity	NPC301217
0.7754	Intermediate Similarity	NPC55018
0.7752	Intermediate Similarity	NPC107846
0.775	Intermediate Similarity	NPC149545
0.7744	Intermediate Similarity	NPC164295
0.7744	Intermediate Similarity	NPC15083
0.7744	Intermediate Similarity	NPC239134
0.7744	Intermediate Similarity	NPC196979
0.7744	Intermediate Similarity	NPC470976
0.7744	Intermediate Similarity	NPC470977
0.7744	Intermediate Similarity	NPC137264
0.7737	Intermediate Similarity	NPC157855
0.7737	Intermediate Similarity	NPC259685
0.7734	Intermediate Similarity	NPC476332
0.7734	Intermediate Similarity	NPC473464
0.7727	Intermediate Similarity	NPC187907
0.7727	Intermediate Similarity	NPC473019
0.7727	Intermediate Similarity	NPC66246
0.7727	Intermediate Similarity	NPC170546
0.7721	Intermediate Similarity	NPC474610
0.7721	Intermediate Similarity	NPC99854
0.7712	Intermediate Similarity	NPC473393
0.771	Intermediate Similarity	NPC293387
0.771	Intermediate Similarity	NPC22783
0.7704	Intermediate Similarity	NPC292998
0.7698	Intermediate Similarity	NPC172986
0.7698	Intermediate Similarity	NPC235239
0.7698	Intermediate Similarity	NPC98748
0.7698	Intermediate Similarity	NPC241100
0.7698	Intermediate Similarity	NPC159275
0.7698	Intermediate Similarity	NPC234956
0.7698	Intermediate Similarity	NPC270883
0.7698	Intermediate Similarity	NPC261227
0.7698	Intermediate Similarity	NPC150522
0.7692	Intermediate Similarity	NPC88403
0.7692	Intermediate Similarity	NPC224657
0.7687	Intermediate Similarity	NPC284424
0.7687	Intermediate Similarity	NPC474340
0.7686	Intermediate Similarity	NPC473809
0.7681	Intermediate Similarity	NPC201395
0.7681	Intermediate Similarity	NPC473988
0.7681	Intermediate Similarity	NPC71903
0.7674	Intermediate Similarity	NPC315807
0.7674	Intermediate Similarity	NPC273772
0.7674	Intermediate Similarity	NPC109675
0.7669	Intermediate Similarity	NPC327457
0.7669	Intermediate Similarity	NPC115998
0.7669	Intermediate Similarity	NPC7569
0.7669	Intermediate Similarity	NPC86774
0.7669	Intermediate Similarity	NPC39753
0.7669	Intermediate Similarity	NPC146615
0.7664	Intermediate Similarity	NPC61546
0.7664	Intermediate Similarity	NPC72452
0.7664	Intermediate Similarity	NPC13408
0.766	Intermediate Similarity	NPC71739
0.7652	Intermediate Similarity	NPC2401
0.7652	Intermediate Similarity	NPC473907
0.7652	Intermediate Similarity	NPC475017
0.7652	Intermediate Similarity	NPC196034
0.7647	Intermediate Similarity	NPC298900
0.7647	Intermediate Similarity	NPC125269
0.7643	Intermediate Similarity	NPC103362
0.7643	Intermediate Similarity	NPC64908
0.7643	Intermediate Similarity	NPC282300
0.7643	Intermediate Similarity	NPC205006
0.7643	Intermediate Similarity	NPC147688
0.7643	Intermediate Similarity	NPC118840
0.7643	Intermediate Similarity	NPC110969
0.7643	Intermediate Similarity	NPC156590
0.7642	Intermediate Similarity	NPC53953
0.763	Intermediate Similarity	NPC470871
0.763	Intermediate Similarity	NPC229646
0.7627	Intermediate Similarity	NPC109637
0.7626	Intermediate Similarity	NPC310370
0.7626	Intermediate Similarity	NPC183642
0.7626	Intermediate Similarity	NPC11566
0.7626	Intermediate Similarity	NPC53181
0.7626	Intermediate Similarity	NPC78913
0.7626	Intermediate Similarity	NPC217186
0.7626	Intermediate Similarity	NPC18260
0.7626	Intermediate Similarity	NPC170812
0.7626	Intermediate Similarity	NPC473209
0.7623	Intermediate Similarity	NPC23332
0.7619	Intermediate Similarity	NPC243704
0.7619	Intermediate Similarity	NPC171023
0.7615	Intermediate Similarity	NPC201667
0.7615	Intermediate Similarity	NPC73413
0.7615	Intermediate Similarity	NPC27671
0.7612	Intermediate Similarity	NPC141549
0.7609	Intermediate Similarity	NPC253616
0.7609	Intermediate Similarity	NPC103001
0.7609	Intermediate Similarity	NPC265335
0.7607	Intermediate Similarity	NPC84325
0.76	Intermediate Similarity	NPC316062
0.76	Intermediate Similarity	NPC470860
0.7597	Intermediate Similarity	NPC311219
0.7594	Intermediate Similarity	NPC197425
0.7594	Intermediate Similarity	NPC473894
0.7594	Intermediate Similarity	NPC474289
0.7594	Intermediate Similarity	NPC206028
0.7591	Intermediate Similarity	NPC77955
0.7591	Intermediate Similarity	NPC104796
0.7591	Intermediate Similarity	NPC307401
0.7589	Intermediate Similarity	NPC217083
0.7589	Intermediate Similarity	NPC59739
0.7589	Intermediate Similarity	NPC11561
0.7589	Intermediate Similarity	NPC299080

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 NPC168050 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	988
0.2-0.3	1179
0.3-0.4	2619
0.4-0.5	2157
0.5-0.6	1281
0.6-0.7	515
0.7-0.8	80
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8699	High Similarity	NPD3267	Approved
0.8699	High Similarity	NPD3266	Approved
0.8504	High Similarity	NPD3268	Approved
0.8254	Intermediate Similarity	NPD2797	Approved
0.8083	Intermediate Similarity	NPD1241	Discontinued
0.808	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8016	Intermediate Similarity	NPD3972	Approved
0.7939	Intermediate Similarity	NPD2313	Discontinued
0.7907	Intermediate Similarity	NPD2798	Approved
0.7891	Intermediate Similarity	NPD3225	Approved
0.7883	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD9697	Approved
0.7851	Intermediate Similarity	NPD5535	Approved
0.782	Intermediate Similarity	NPD4307	Phase 2
0.7786	Intermediate Similarity	NPD6832	Phase 2
0.7744	Intermediate Similarity	NPD8032	Phase 2
0.7721	Intermediate Similarity	NPD2799	Discontinued
0.7698	Intermediate Similarity	NPD5585	Approved
0.7669	Intermediate Similarity	NPD6798	Discontinued
0.7664	Intermediate Similarity	NPD2796	Approved
0.7597	Intermediate Similarity	NPD9717	Approved
0.7591	Intermediate Similarity	NPD3748	Approved
0.7591	Intermediate Similarity	NPD4308	Phase 3
0.7559	Intermediate Similarity	NPD1651	Approved
0.7557	Intermediate Similarity	NPD1203	Approved
0.754	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD17	Approved
0.75	Intermediate Similarity	NPD1778	Approved
0.7483	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1471	Phase 3
0.7482	Intermediate Similarity	NPD2346	Discontinued
0.7481	Intermediate Similarity	NPD1876	Approved
0.7447	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3496	Discontinued
0.741	Intermediate Similarity	NPD6100	Approved
0.741	Intermediate Similarity	NPD6099	Approved
0.7407	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1296	Phase 2
0.7405	Intermediate Similarity	NPD4359	Approved
0.7372	Intermediate Similarity	NPD6355	Discontinued
0.7372	Intermediate Similarity	NPD4618	Approved
0.7372	Intermediate Similarity	NPD4622	Approved
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1019	Discontinued
0.7361	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2344	Approved
0.7355	Intermediate Similarity	NPD3134	Approved
0.7347	Intermediate Similarity	NPD6585	Discontinued
0.7344	Intermediate Similarity	NPD1894	Discontinued
0.7338	Intermediate Similarity	NPD7033	Discontinued
0.7333	Intermediate Similarity	NPD7095	Approved
0.7328	Intermediate Similarity	NPD1608	Approved
0.7324	Intermediate Similarity	NPD3750	Approved
0.7297	Intermediate Similarity	NPD5890	Approved
0.7297	Intermediate Similarity	NPD5889	Approved
0.7297	Intermediate Similarity	NPD7411	Suspended
0.7295	Intermediate Similarity	NPD1358	Approved
0.7287	Intermediate Similarity	NPD5691	Approved
0.7279	Intermediate Similarity	NPD3226	Approved
0.7266	Intermediate Similarity	NPD5689	Approved
0.7266	Intermediate Similarity	NPD5688	Approved
0.7252	Intermediate Similarity	NPD1535	Discovery
0.7252	Intermediate Similarity	NPD1611	Approved
0.7244	Intermediate Similarity	NPD6671	Approved
0.7244	Intermediate Similarity	NPD2557	Approved
0.7244	Intermediate Similarity	NPD7157	Approved
0.7236	Intermediate Similarity	NPD2684	Approved
0.7234	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6233	Phase 2
0.7203	Intermediate Similarity	NPD4628	Phase 3
0.7203	Intermediate Similarity	NPD7003	Approved
0.7197	Intermediate Similarity	NPD1481	Phase 2
0.7183	Intermediate Similarity	NPD1549	Phase 2
0.7177	Intermediate Similarity	NPD5451	Approved
0.7176	Intermediate Similarity	NPD3847	Discontinued
0.7174	Intermediate Similarity	NPD3142	Approved
0.7174	Intermediate Similarity	NPD3140	Approved
0.7163	Intermediate Similarity	NPD4476	Approved
0.7163	Intermediate Similarity	NPD2935	Discontinued
0.7163	Intermediate Similarity	NPD4477	Approved
0.7154	Intermediate Similarity	NPD3024	Approved
0.7154	Intermediate Similarity	NPD3025	Approved
0.7154	Intermediate Similarity	NPD290	Approved
0.7153	Intermediate Similarity	NPD2309	Approved
0.7152	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7143	Intermediate Similarity	NPD7843	Approved
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2614	Approved
0.7121	Intermediate Similarity	NPD1281	Approved
0.7121	Intermediate Similarity	NPD422	Phase 1
0.7114	Intermediate Similarity	NPD6599	Discontinued
0.7113	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2353	Approved
0.7109	Intermediate Similarity	NPD6387	Discontinued
0.7101	Intermediate Similarity	NPD4062	Phase 3
0.7099	Intermediate Similarity	NPD4626	Approved
0.7099	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1510	Phase 2
0.709	Intermediate Similarity	NPD8651	Approved
0.7075	Intermediate Similarity	NPD6273	Approved
0.7075	Intermediate Similarity	NPD5049	Phase 3
0.7073	Intermediate Similarity	NPD968	Approved
0.7063	Intermediate Similarity	NPD2897	Discontinued
0.7063	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2424	Discontinued
0.7055	Intermediate Similarity	NPD6799	Approved
0.705	Intermediate Similarity	NPD1240	Approved
0.705	Intermediate Similarity	NPD2979	Phase 3
0.7049	Intermediate Similarity	NPD5909	Discontinued
0.7047	Intermediate Similarity	NPD7458	Discontinued
0.7045	Intermediate Similarity	NPD3023	Approved
0.7045	Intermediate Similarity	NPD3026	Approved
0.7034	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3887	Approved
0.7029	Intermediate Similarity	NPD411	Approved
0.7027	Intermediate Similarity	NPD5403	Approved
0.7023	Intermediate Similarity	NPD3445	Approved
0.7023	Intermediate Similarity	NPD3049	Approved
0.7023	Intermediate Similarity	NPD3444	Approved
0.7023	Intermediate Similarity	NPD3443	Approved
0.7021	Intermediate Similarity	NPD7097	Phase 1
0.702	Intermediate Similarity	NPD6801	Discontinued
0.7014	Intermediate Similarity	NPD2800	Approved
0.7014	Intermediate Similarity	NPD1243	Approved
0.7007	Intermediate Similarity	NPD4661	Approved
0.7007	Intermediate Similarity	NPD4662	Approved
0.7007	Intermediate Similarity	NPD5401	Approved
0.7007	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD447	Suspended
0.6993	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4870	Approved
0.6974	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7819	Suspended
0.697	Remote Similarity	NPD3019	Approved
0.697	Remote Similarity	NPD2932	Approved
0.6966	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4110	Phase 3
0.6963	Remote Similarity	NPD1283	Approved
0.6953	Remote Similarity	NPD594	Approved
0.6953	Remote Similarity	NPD592	Approved
0.6953	Remote Similarity	NPD5283	Phase 1
0.695	Remote Similarity	NPD1607	Approved
0.6947	Remote Similarity	NPD2486	Discontinued
0.6947	Remote Similarity	NPD1548	Phase 1
0.6947	Remote Similarity	NPD6580	Approved
0.6947	Remote Similarity	NPD6581	Approved
0.6944	Remote Similarity	NPD4534	Discontinued
0.6939	Remote Similarity	NPD1511	Approved
0.6933	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4060	Phase 1
0.6929	Remote Similarity	NPD4140	Approved
0.6929	Remote Similarity	NPD1139	Approved
0.6929	Remote Similarity	NPD1137	Approved
0.6923	Remote Similarity	NPD1551	Phase 2
0.6923	Remote Similarity	NPD9493	Approved
0.6923	Remote Similarity	NPD3596	Phase 2
0.6918	Remote Similarity	NPD2354	Approved
0.6908	Remote Similarity	NPD6844	Discontinued
0.6906	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4380	Phase 2
0.6884	Remote Similarity	NPD4908	Phase 1
0.6879	Remote Similarity	NPD5124	Phase 1
0.6879	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1138	Approved
0.6875	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6002	Phase 3
0.6875	Remote Similarity	NPD6004	Phase 3
0.6875	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6005	Phase 3
0.6863	Remote Similarity	NPD2801	Approved
0.6861	Remote Similarity	NPD5647	Approved
0.6859	Remote Similarity	NPD3251	Approved
0.6846	Remote Similarity	NPD1512	Approved
0.6842	Remote Similarity	NPD5846	Approved
0.6842	Remote Similarity	NPD2556	Approved
0.6842	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6516	Phase 2
0.6842	Remote Similarity	NPD2554	Approved
0.6839	Remote Similarity	NPD7075	Discontinued
0.6835	Remote Similarity	NPD4625	Phase 3
0.6831	Remote Similarity	NPD6651	Approved
0.6828	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3817	Phase 2
0.6806	Remote Similarity	NPD2531	Phase 2
0.6806	Remote Similarity	NPD2438	Suspended
0.6806	Remote Similarity	NPD6032	Approved
0.68	Remote Similarity	NPD920	Approved
0.68	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1934	Approved
0.6797	Remote Similarity	NPD6280	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