NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.08
Volume:	212.184
LogP:	3.43
LogD:	3.068
LogS:	-3.485
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.764
Synthetic Accessibility Score:	2.416
Fsp3:	0.25
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:	-4.657
MDCK Permeability:	2.6955616704071872e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.39

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.337
Plasma Protein Binding (PPB):	91.47789764404297%
Volume Distribution (VD):	0.373
Pgp-substrate:	5.396440505981445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.304
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.14
CYP2C9-substrate:	0.207
CYP2D6-inhibitor:	0.185
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	2.704
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.796
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.286
Carcinogencity:	0.524
Eye Corrosion:	0.004
Eye Irritation:	0.83
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC2401

Natural Product ID:	NPC2401
*Common Name:**	2,2-Dimethylchromene-6-Carboxylic Acid
IUPAC Name:	2,2-dimethylchromene-6-carboxylic acid
Synonyms:
Standard InCHIKey:	AXICIBPYBONRSP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H12O3/c1-12(2)6-5-8-7-9(11(13)14)3-4-10(8)15-12/h3-7H,1-2H3,(H,13,14)
SMILES:	OC(=O)c1ccc2c(c1)C=CC(O2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469159
PubChem CID:	5319235
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-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
NPO33179	piper sp.	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568762]
NPO1451	Aspergillus duricaulis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26517152]
NPO8059	Piper aduncum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158163]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[8588862]
NPO8059	Piper aduncum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8059	Piper aduncum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8059	Piper aduncum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1451	Aspergillus duricaulis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8059	Piper aduncum	Species	Piperaceae	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	1
IC50	1
Others	9

Activity Type	# Activity
Individual Protein	2
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	Activity	=	5.0	ug	PMID[529864]
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	Activity	=	5.0	ug	PMID[529864]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	2.5	%	PMID[529865]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	1.3	%	PMID[529865]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	0.0	%	PMID[529865]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	EC50	=	251500.0	nM	PMID[529866]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	IC50	>	300000.0	nM	PMID[529866]

☑ 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 NPC2401 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	318
0.1-0.2	1661
0.2-0.3	4375
0.3-0.4	10130
0.4-0.5	7796
0.5-0.6	3986
0.6-0.7	8171
0.7-0.8	5498
0.8-0.85	702
0.85-0.9	45
0.9-0.95	9
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC109778
0.9677	High Similarity	NPC327457
0.9677	High Similarity	NPC86774
0.959	High Similarity	NPC165556
0.928	High Similarity	NPC37512
0.9187	High Similarity	NPC291189
0.9187	High Similarity	NPC69403
0.9127	High Similarity	NPC121104
0.904	High Similarity	NPC221798
0.9023	High Similarity	NPC473988
0.9016	High Similarity	NPC61779
0.9	High Similarity	NPC66158
0.8939	High Similarity	NPC151113
0.8898	High Similarity	NPC475236
0.8889	High Similarity	NPC184219
0.8889	High Similarity	NPC184053
0.888	High Similarity	NPC67300
0.8837	High Similarity	NPC473019
0.8832	High Similarity	NPC113397
0.8806	High Similarity	NPC332594
0.8689	High Similarity	NPC220540
0.8667	High Similarity	NPC221046
0.8657	High Similarity	NPC163029
0.8647	High Similarity	NPC93756
0.8647	High Similarity	NPC108113
0.8633	High Similarity	NPC469953
0.8629	High Similarity	NPC27633
0.8629	High Similarity	NPC94298
0.8618	High Similarity	NPC131192
0.8615	High Similarity	NPC2596
0.8613	High Similarity	NPC475680
0.8613	High Similarity	NPC305355
0.8603	High Similarity	NPC470669
0.8603	High Similarity	NPC470668
0.8594	High Similarity	NPC89630
0.8582	High Similarity	NPC61499
0.8582	High Similarity	NPC125920
0.8571	High Similarity	NPC229646
0.8551	High Similarity	NPC147688
0.8551	High Similarity	NPC156590
0.8551	High Similarity	NPC118840
0.8551	High Similarity	NPC205006
0.8551	High Similarity	NPC103362
0.8551	High Similarity	NPC64908
0.855	High Similarity	NPC939
0.8548	High Similarity	NPC183154
0.8548	High Similarity	NPC263754
0.854	High Similarity	NPC473076
0.854	High Similarity	NPC23257
0.8538	High Similarity	NPC22783
0.8529	High Similarity	NPC253616
0.8529	High Similarity	NPC62735
0.8527	High Similarity	NPC244495
0.8527	High Similarity	NPC93219
0.8519	High Similarity	NPC60667
0.8511	High Similarity	NPC180477
0.8511	High Similarity	NPC66991
0.8496	Intermediate Similarity	NPC302844
0.8489	Intermediate Similarity	NPC11561
0.8489	Intermediate Similarity	NPC226636
0.8489	Intermediate Similarity	NPC36181
0.8485	Intermediate Similarity	NPC42292
0.8485	Intermediate Similarity	NPC307732
0.848	Intermediate Similarity	NPC273282
0.848	Intermediate Similarity	NPC474890
0.848	Intermediate Similarity	NPC161943
0.8478	Intermediate Similarity	NPC172986
0.8478	Intermediate Similarity	NPC235239
0.8478	Intermediate Similarity	NPC270883
0.8478	Intermediate Similarity	NPC261227
0.8478	Intermediate Similarity	NPC150522
0.8478	Intermediate Similarity	NPC471587
0.8478	Intermediate Similarity	NPC221173
0.8473	Intermediate Similarity	NPC125887
0.8473	Intermediate Similarity	NPC473744
0.8468	Intermediate Similarity	NPC470860
0.8467	Intermediate Similarity	NPC201395
0.8467	Intermediate Similarity	NPC36414
0.8467	Intermediate Similarity	NPC131130
0.8467	Intermediate Similarity	NPC71903
0.8462	Intermediate Similarity	NPC237868
0.8456	Intermediate Similarity	NPC174999
0.8456	Intermediate Similarity	NPC268081
0.8451	Intermediate Similarity	NPC37139
0.8451	Intermediate Similarity	NPC211811
0.844	Intermediate Similarity	NPC154217
0.844	Intermediate Similarity	NPC286038
0.844	Intermediate Similarity	NPC57470
0.8438	Intermediate Similarity	NPC311219
0.8429	Intermediate Similarity	NPC87609
0.8429	Intermediate Similarity	NPC94794
0.8429	Intermediate Similarity	NPC196459
0.8429	Intermediate Similarity	NPC470296
0.8429	Intermediate Similarity	NPC188632
0.8429	Intermediate Similarity	NPC112791
0.8429	Intermediate Similarity	NPC38219
0.8421	Intermediate Similarity	NPC104854
0.8421	Intermediate Similarity	NPC270369
0.8421	Intermediate Similarity	NPC473777
0.8421	Intermediate Similarity	NPC5515
0.8417	Intermediate Similarity	NPC110969
0.8417	Intermediate Similarity	NPC470555
0.8409	Intermediate Similarity	NPC66246
0.8409	Intermediate Similarity	NPC170546
0.8406	Intermediate Similarity	NPC301217
0.8406	Intermediate Similarity	NPC18260
0.8406	Intermediate Similarity	NPC472343
0.8406	Intermediate Similarity	NPC220062
0.8406	Intermediate Similarity	NPC183642
0.8406	Intermediate Similarity	NPC55018
0.8406	Intermediate Similarity	NPC170812
0.8406	Intermediate Similarity	NPC254994
0.8406	Intermediate Similarity	NPC303633
0.8406	Intermediate Similarity	NPC78913
0.8406	Intermediate Similarity	NPC216978
0.8406	Intermediate Similarity	NPC96565
0.8406	Intermediate Similarity	NPC310370
0.8397	Intermediate Similarity	NPC243688
0.8394	Intermediate Similarity	NPC138047
0.8394	Intermediate Similarity	NPC131782
0.8394	Intermediate Similarity	NPC228661
0.8394	Intermediate Similarity	NPC474624
0.8382	Intermediate Similarity	NPC101752
0.838	Intermediate Similarity	NPC129650
0.838	Intermediate Similarity	NPC140120
0.838	Intermediate Similarity	NPC297886
0.838	Intermediate Similarity	NPC249942
0.8372	Intermediate Similarity	NPC141252
0.8372	Intermediate Similarity	NPC11799
0.837	Intermediate Similarity	NPC27643
0.837	Intermediate Similarity	NPC57601
0.8369	Intermediate Similarity	NPC196137
0.8369	Intermediate Similarity	NPC178627
0.8369	Intermediate Similarity	NPC311741
0.8369	Intermediate Similarity	NPC469935
0.8369	Intermediate Similarity	NPC234629
0.8369	Intermediate Similarity	NPC1886
0.8358	Intermediate Similarity	NPC475589
0.8358	Intermediate Similarity	NPC470859
0.8358	Intermediate Similarity	NPC31872
0.8358	Intermediate Similarity	NPC473584
0.8358	Intermediate Similarity	NPC175159
0.8357	Intermediate Similarity	NPC299080
0.8357	Intermediate Similarity	NPC214236
0.8357	Intermediate Similarity	NPC144499
0.8357	Intermediate Similarity	NPC162476
0.8357	Intermediate Similarity	NPC78803
0.8357	Intermediate Similarity	NPC293852
0.8357	Intermediate Similarity	NPC217083
0.8357	Intermediate Similarity	NPC59739
0.8357	Intermediate Similarity	NPC62840
0.8346	Intermediate Similarity	NPC183348
0.8346	Intermediate Similarity	NPC474874
0.8346	Intermediate Similarity	NPC282230
0.8345	Intermediate Similarity	NPC307990
0.8345	Intermediate Similarity	NPC69769
0.8345	Intermediate Similarity	NPC241100
0.8345	Intermediate Similarity	NPC16455
0.8345	Intermediate Similarity	NPC159275
0.8333	Intermediate Similarity	NPC199458
0.8333	Intermediate Similarity	NPC470671
0.8333	Intermediate Similarity	NPC180351
0.8333	Intermediate Similarity	NPC474504
0.8333	Intermediate Similarity	NPC185066
0.8333	Intermediate Similarity	NPC219584
0.8333	Intermediate Similarity	NPC183639
0.8333	Intermediate Similarity	NPC470083
0.8333	Intermediate Similarity	NPC470672
0.8333	Intermediate Similarity	NPC474487
0.8333	Intermediate Similarity	NPC151973
0.8333	Intermediate Similarity	NPC293453
0.8333	Intermediate Similarity	NPC158866
0.8322	Intermediate Similarity	NPC469933
0.8322	Intermediate Similarity	NPC208303
0.8322	Intermediate Similarity	NPC161864
0.8321	Intermediate Similarity	NPC472516
0.832	Intermediate Similarity	NPC83718
0.831	Intermediate Similarity	NPC181388
0.831	Intermediate Similarity	NPC470322
0.8309	Intermediate Similarity	NPC172262
0.8306	Intermediate Similarity	NPC161696
0.8298	Intermediate Similarity	NPC255133
0.8298	Intermediate Similarity	NPC295696
0.8298	Intermediate Similarity	NPC166138
0.8298	Intermediate Similarity	NPC213900
0.8298	Intermediate Similarity	NPC18585
0.8298	Intermediate Similarity	NPC242100
0.8298	Intermediate Similarity	NPC106985
0.8298	Intermediate Similarity	NPC219915
0.8296	Intermediate Similarity	NPC55147
0.8296	Intermediate Similarity	NPC287533
0.8296	Intermediate Similarity	NPC25937
0.8296	Intermediate Similarity	NPC10971
0.8295	Intermediate Similarity	NPC13007
0.8295	Intermediate Similarity	NPC257188
0.8286	Intermediate Similarity	NPC3188
0.8286	Intermediate Similarity	NPC254010
0.8286	Intermediate Similarity	NPC229916
0.8286	Intermediate Similarity	NPC282300
0.8284	Intermediate Similarity	NPC196979

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 NPC2401 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	988
0.2-0.3	1503
0.3-0.4	2554
0.4-0.5	1865
0.5-0.6	1265
0.6-0.7	490
0.7-0.8	172
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8815	High Similarity	NPD7421	Clinical (unspecified phase)
0.8629	High Similarity	NPD9545	Approved
0.8438	Intermediate Similarity	NPD9717	Approved
0.8295	Intermediate Similarity	NPD1608	Approved
0.8273	Intermediate Similarity	NPD1243	Approved
0.8248	Intermediate Similarity	NPD2799	Discontinued
0.8244	Intermediate Similarity	NPD1203	Approved
0.8239	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1240	Approved
0.8217	Intermediate Similarity	NPD422	Phase 1
0.8214	Intermediate Similarity	NPD3750	Approved
0.8214	Intermediate Similarity	NPD4628	Phase 3
0.8209	Intermediate Similarity	NPD2313	Discontinued
0.8151	Intermediate Similarity	NPD7411	Suspended
0.8116	Intermediate Similarity	NPD4308	Phase 3
0.8112	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD2797	Approved
0.8102	Intermediate Similarity	NPD1607	Approved
0.8074	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1549	Phase 2
0.8071	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD17	Approved
0.8033	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD3225	Approved
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1510	Phase 2
0.7986	Intermediate Similarity	NPD3748	Approved
0.7973	Intermediate Similarity	NPD6801	Discontinued
0.7972	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3268	Approved
0.7937	Intermediate Similarity	NPD1241	Discontinued
0.7929	Intermediate Similarity	NPD1551	Phase 2
0.7929	Intermediate Similarity	NPD2796	Approved
0.7929	Intermediate Similarity	NPD2935	Discontinued
0.7919	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7819	Suspended
0.7917	Intermediate Similarity	NPD6799	Approved
0.7891	Intermediate Similarity	NPD3226	Approved
0.7891	Intermediate Similarity	NPD9493	Approved
0.7881	Intermediate Similarity	NPD7075	Discontinued
0.7877	Intermediate Similarity	NPD920	Approved
0.7872	Intermediate Similarity	NPD2344	Approved
0.7869	Intermediate Similarity	NPD9697	Approved
0.7862	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7033	Discontinued
0.7826	Intermediate Similarity	NPD4307	Phase 2
0.781	Intermediate Similarity	NPD411	Approved
0.781	Intermediate Similarity	NPD3764	Approved
0.781	Intermediate Similarity	NPD1296	Phase 2
0.7786	Intermediate Similarity	NPD1778	Approved
0.7778	Intermediate Similarity	NPD2354	Approved
0.777	Intermediate Similarity	NPD447	Suspended
0.7746	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2346	Discontinued
0.7744	Intermediate Similarity	NPD1481	Phase 2
0.7718	Intermediate Similarity	NPD6599	Discontinued
0.7708	Intermediate Similarity	NPD7003	Approved
0.7708	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD3267	Approved
0.7704	Intermediate Similarity	NPD3266	Approved
0.7697	Intermediate Similarity	NPD7768	Phase 2
0.7687	Intermediate Similarity	NPD5049	Phase 3
0.7671	Intermediate Similarity	NPD1511	Approved
0.7669	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1535	Discovery
0.7664	Intermediate Similarity	NPD6832	Phase 2
0.7655	Intermediate Similarity	NPD2309	Approved
0.7647	Intermediate Similarity	NPD1019	Discontinued
0.7647	Intermediate Similarity	NPD2798	Approved
0.7647	Intermediate Similarity	NPD3749	Approved
0.7643	Intermediate Similarity	NPD5124	Phase 1
0.7643	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD2800	Approved
0.7634	Intermediate Similarity	NPD1894	Discontinued
0.763	Intermediate Similarity	NPD1283	Approved
0.7622	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2353	Approved
0.7612	Intermediate Similarity	NPD3972	Approved
0.76	Intermediate Similarity	NPD4380	Phase 2
0.7586	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1512	Approved
0.7566	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6798	Discontinued
0.7552	Intermediate Similarity	NPD4476	Approved
0.7552	Intermediate Similarity	NPD4477	Approved
0.7533	Intermediate Similarity	NPD7458	Discontinued
0.7519	Intermediate Similarity	NPD4626	Approved
0.7518	Intermediate Similarity	NPD230	Phase 1
0.7516	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.7484	Intermediate Similarity	NPD919	Approved
0.7468	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD9494	Approved
0.746	Intermediate Similarity	NPD9263	Approved
0.746	Intermediate Similarity	NPD9267	Approved
0.746	Intermediate Similarity	NPD9264	Approved
0.7445	Intermediate Similarity	NPD1164	Approved
0.7444	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5844	Phase 1
0.7432	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3887	Approved
0.741	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1281	Approved
0.7403	Intermediate Similarity	NPD3817	Phase 2
0.7403	Intermediate Similarity	NPD4288	Approved
0.7402	Intermediate Similarity	NPD9266	Approved
0.7402	Intermediate Similarity	NPD74	Approved
0.74	Intermediate Similarity	NPD5403	Approved
0.7394	Intermediate Similarity	NPD6355	Discontinued
0.7394	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD1934	Approved
0.7383	Intermediate Similarity	NPD5401	Approved
0.7381	Intermediate Similarity	NPD3134	Approved
0.7379	Intermediate Similarity	NPD6002	Phase 3
0.7379	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6005	Phase 3
0.7379	Intermediate Similarity	NPD6004	Phase 3
0.7379	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1548	Phase 1
0.7346	Intermediate Similarity	NPD5953	Discontinued
0.7343	Intermediate Similarity	NPD6651	Approved
0.7338	Intermediate Similarity	NPD1465	Phase 2
0.7338	Intermediate Similarity	NPD2801	Approved
0.7333	Intermediate Similarity	NPD6273	Approved
0.7329	Intermediate Similarity	NPD7286	Phase 2
0.7324	Intermediate Similarity	NPD3140	Approved
0.7324	Intermediate Similarity	NPD3142	Approved
0.7323	Intermediate Similarity	NPD1358	Approved
0.7313	Intermediate Similarity	NPD5691	Approved
0.731	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD6100	Approved
0.7308	Intermediate Similarity	NPD5535	Approved
0.7303	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7177	Discontinued
0.7248	Intermediate Similarity	NPD7440	Discontinued
0.7246	Intermediate Similarity	NPD1876	Approved
0.7244	Intermediate Similarity	NPD3882	Suspended
0.7233	Intermediate Similarity	NPD6232	Discontinued
0.7231	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2186	Approved
0.7214	Intermediate Similarity	NPD454	Approved
0.7208	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3847	Discontinued
0.7206	Intermediate Similarity	NPD3496	Discontinued
0.7203	Intermediate Similarity	NPD4060	Phase 1
0.7163	Intermediate Similarity	NPD2614	Approved
0.7153	Intermediate Similarity	NPD1610	Phase 2
0.7143	Intermediate Similarity	NPD9261	Approved
0.7143	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6671	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD6585	Discontinued
0.7133	Intermediate Similarity	NPD6666	Approved
0.7133	Intermediate Similarity	NPD6233	Phase 2
0.7133	Intermediate Similarity	NPD6667	Approved
0.7133	Intermediate Similarity	NPD4062	Phase 3
0.7113	Intermediate Similarity	NPD7095	Approved
0.7099	Intermediate Similarity	NPD7473	Discontinued
0.7071	Intermediate Similarity	NPD987	Approved
0.707	Intermediate Similarity	NPD2296	Approved
0.707	Intermediate Similarity	NPD5402	Approved
0.7068	Intermediate Similarity	NPD9281	Approved
0.7068	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6959	Discontinued
0.7063	Intermediate Similarity	NPD1247	Approved
0.7059	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD1651	Approved
0.7059	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3818	Discontinued
0.7055	Intermediate Similarity	NPD7097	Phase 1
0.7055	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD290	Approved
0.7051	Intermediate Similarity	NPD7577	Discontinued
0.7047	Intermediate Similarity	NPD1652	Phase 2
0.704	Intermediate Similarity	NPD1238	Approved
0.7034	Intermediate Similarity	NPD1184	Approved
0.7034	Intermediate Similarity	NPD4340	Discontinued
0.7029	Intermediate Similarity	NPD1201	Approved
0.7029	Intermediate Similarity	NPD1611	Approved
0.702	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8032	Phase 2
0.7007	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8455	Phase 2
0.7	Intermediate Similarity	NPD5494	Approved
0.7	Intermediate Similarity	NPD2684	Approved
0.7	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4625	Phase 3
0.6988	Remote Similarity	NPD6559	Discontinued
0.6987	Remote Similarity	NPD5889	Approved
0.6987	Remote Similarity	NPD5890	Approved
0.698	Remote Similarity	NPD2424	Discontinued

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