NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	273.096
LogP:	1.817
LogD:	1.646
LogS:	-3.444
# Rotatable Bonds:	1
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.807
Synthetic Accessibility Score:	3.498
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.788
MDCK Permeability:	1.94111871678615e-05
Pgp-inhibitor:	0.093
Pgp-substrate:	0.25
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	82.1537094116211%
Volume Distribution (VD):	1.167
Pgp-substrate:	18.481016159057617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.385
CYP1A2-substrate:	0.82
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.649
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.411
CYP2D6-inhibitor:	0.107
CYP2D6-substrate:	0.399
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	8.915
Half-life (T1/2):	0.309

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.369
Rat Oral Acute Toxicity:	0.472
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.1
Carcinogencity:	0.902
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.669

Download Data

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

Natural Product: NPC232246

Natural Product ID:	NPC232246
*Common Name:**	(-)-Trans-Methylkhellactone
IUPAC Name:	(9R,10S)-9-hydroxy-10-methoxy-8,8-dimethyl-9,10-dihydropyrano[2,3-f]chromen-2-one
Synonyms:
Standard InCHIKey:	MDDPVXHWOABQJQ-UONOGXRCSA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-15(2)14(17)13(18-3)11-9(20-15)6-4-8-5-7-10(16)19-12(8)11/h4-7,13-14,17H,1-3H3/t13-,14+/m0/s1
SMILES:	CO[C@H]1c2c(ccc3c2oc(=O)cc3)OC([C@@H]1O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463635
PubChem CID:	21679806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO32915	prionosciadium watsoni	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088423]

☑ 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
IC50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	108000.0	nM	PMID[543739]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	808000.0	nM	PMID[543739]

☑ 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 NPC232246 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	352
0.1-0.2	1559
0.2-0.3	3872
0.3-0.4	8586
0.4-0.5	9937
0.5-0.6	4064
0.6-0.7	5812
0.7-0.8	4864
0.8-0.85	2772
0.85-0.9	678
0.9-0.95	130
0.95-1	71

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC153818
0.9923	High Similarity	NPC188380
0.9923	High Similarity	NPC78746
0.9923	High Similarity	NPC224543
0.9848	High Similarity	NPC312881
0.9847	High Similarity	NPC294456
0.9847	High Similarity	NPC281014
0.9847	High Similarity	NPC184861
0.9847	High Similarity	NPC225106
0.9847	High Similarity	NPC212124
0.9774	High Similarity	NPC195357
0.9774	High Similarity	NPC152771
0.9774	High Similarity	NPC287286
0.9773	High Similarity	NPC279573
0.9769	High Similarity	NPC62366
0.9697	High Similarity	NPC155963
0.9695	High Similarity	NPC472525
0.9624	High Similarity	NPC151946
0.9624	High Similarity	NPC211110
0.9621	High Similarity	NPC26954
0.9621	High Similarity	NPC38099
0.9618	High Similarity	NPC224475
0.9618	High Similarity	NPC180716
0.9618	High Similarity	NPC50896
0.9618	High Similarity	NPC213173
0.9618	High Similarity	NPC204353
0.9618	High Similarity	NPC326600
0.9545	High Similarity	NPC33986
0.9542	High Similarity	NPC318400
0.9542	High Similarity	NPC296624
0.9542	High Similarity	NPC207002
0.9542	High Similarity	NPC133956
0.9542	High Similarity	NPC167111
0.9542	High Similarity	NPC471910
0.9489	High Similarity	NPC469701
0.9489	High Similarity	NPC85624
0.947	High Similarity	NPC127888
0.947	High Similarity	NPC267412
0.947	High Similarity	NPC164269
0.947	High Similarity	NPC98179
0.947	High Similarity	NPC74655
0.947	High Similarity	NPC100986
0.947	High Similarity	NPC253574
0.947	High Similarity	NPC287182
0.947	High Similarity	NPC47163
0.947	High Similarity	NPC18804
0.947	High Similarity	NPC84894
0.947	High Similarity	NPC166672
0.947	High Similarity	NPC319859
0.947	High Similarity	NPC260265
0.947	High Similarity	NPC195343
0.947	High Similarity	NPC198381
0.9398	High Similarity	NPC471909
0.9398	High Similarity	NPC472424
0.9398	High Similarity	NPC86892
0.9398	High Similarity	NPC471625
0.9398	High Similarity	NPC281241
0.9394	High Similarity	NPC31849
0.9389	High Similarity	NPC29734
0.9353	High Similarity	NPC87950
0.9353	High Similarity	NPC296377
0.9353	High Similarity	NPC471764
0.9328	High Similarity	NPC471630
0.9328	High Similarity	NPC128529
0.9328	High Similarity	NPC55615
0.9328	High Similarity	NPC177281
0.9328	High Similarity	NPC149320
0.9328	High Similarity	NPC476455
0.9328	High Similarity	NPC160727
0.9328	High Similarity	NPC283019
0.9318	High Similarity	NPC194277
0.9313	High Similarity	NPC113098
0.9308	High Similarity	NPC185066
0.9286	High Similarity	NPC169510
0.9275	High Similarity	NPC471824
0.9242	High Similarity	NPC272650
0.9242	High Similarity	NPC267336
0.9237	High Similarity	NPC168710
0.9179	High Similarity	NPC307412
0.9179	High Similarity	NPC55149
0.9173	High Similarity	NPC14248
0.9167	High Similarity	NPC80170
0.9154	High Similarity	NPC471826
0.9137	High Similarity	NPC471763
0.9111	High Similarity	NPC469675
0.9104	High Similarity	NPC222036
0.9104	High Similarity	NPC469449
0.9104	High Similarity	NPC7526
0.9104	High Similarity	NPC163557
0.9044	High Similarity	NPC103409
0.9021	High Similarity	NPC103116
0.9015	High Similarity	NPC199204
0.9	High Similarity	NPC111347
0.8978	High Similarity	NPC471069
0.8978	High Similarity	NPC471068
0.8963	High Similarity	NPC291551
0.8963	High Similarity	NPC205797
0.8963	High Similarity	NPC1220
0.8963	High Similarity	NPC469965
0.8963	High Similarity	NPC142563
0.8963	High Similarity	NPC241165
0.8963	High Similarity	NPC141822
0.8939	High Similarity	NPC121740
0.8939	High Similarity	NPC473993
0.8939	High Similarity	NPC258567
0.8939	High Similarity	NPC224774
0.8929	High Similarity	NPC183646
0.8929	High Similarity	NPC119640
0.8923	High Similarity	NPC472518
0.8921	High Similarity	NPC215512
0.8921	High Similarity	NPC279851
0.8921	High Similarity	NPC476442
0.8921	High Similarity	NPC472520
0.8921	High Similarity	NPC300611
0.8913	High Similarity	NPC47040
0.8913	High Similarity	NPC37428
0.8913	High Similarity	NPC278600
0.8913	High Similarity	NPC471071
0.8913	High Similarity	NPC144512
0.8913	High Similarity	NPC471072
0.8913	High Similarity	NPC35501
0.8913	High Similarity	NPC270256
0.8913	High Similarity	NPC137262
0.8913	High Similarity	NPC471070
0.8905	High Similarity	NPC283331
0.8897	High Similarity	NPC131950
0.8897	High Similarity	NPC470264
0.8873	High Similarity	NPC205361
0.8872	High Similarity	NPC469453
0.8865	High Similarity	NPC476457
0.8864	High Similarity	NPC188327
0.8864	High Similarity	NPC234109
0.8855	High Similarity	NPC201667
0.8855	High Similarity	NPC73413
0.8846	High Similarity	NPC96286
0.8846	High Similarity	NPC248429
0.8841	High Similarity	NPC131198
0.8815	High Similarity	NPC103799
0.8811	High Similarity	NPC476347
0.8811	High Similarity	NPC15577
0.8803	High Similarity	NPC226722
0.8797	High Similarity	NPC243688
0.8788	High Similarity	NPC244495
0.8788	High Similarity	NPC471828
0.8788	High Similarity	NPC471827
0.8788	High Similarity	NPC93219
0.8786	High Similarity	NPC138149
0.8779	High Similarity	NPC273772
0.8779	High Similarity	NPC290605
0.8779	High Similarity	NPC173350
0.8779	High Similarity	NPC154176
0.8779	High Similarity	NPC109675
0.875	High Similarity	NPC187398
0.875	High Similarity	NPC476348
0.8741	High Similarity	NPC32463
0.8731	High Similarity	NPC293642
0.8731	High Similarity	NPC472519
0.8731	High Similarity	NPC60704
0.8731	High Similarity	NPC139595
0.8723	High Similarity	NPC93640
0.8723	High Similarity	NPC20631
0.8712	High Similarity	NPC27671
0.8712	High Similarity	NPC291899
0.8707	High Similarity	NPC256141
0.8702	High Similarity	NPC257188
0.8702	High Similarity	NPC13007
0.8692	High Similarity	NPC163200
0.8686	High Similarity	NPC92805
0.8686	High Similarity	NPC469955
0.8686	High Similarity	NPC469952
0.8686	High Similarity	NPC2363
0.8671	High Similarity	NPC106126
0.8671	High Similarity	NPC475719
0.8671	High Similarity	NPC101255
0.8671	High Similarity	NPC108994
0.8671	High Similarity	NPC43716
0.8671	High Similarity	NPC295696
0.8662	High Similarity	NPC229916
0.8662	High Similarity	NPC236419
0.8662	High Similarity	NPC138212
0.8647	High Similarity	NPC232692
0.8647	High Similarity	NPC202594
0.8643	High Similarity	NPC164148
0.8643	High Similarity	NPC43500
0.8636	High Similarity	NPC50720
0.8633	High Similarity	NPC167517
0.8633	High Similarity	NPC262585
0.8633	High Similarity	NPC20829
0.8633	High Similarity	NPC18189
0.863	High Similarity	NPC294522
0.863	High Similarity	NPC21184
0.863	High Similarity	NPC120426
0.863	High Similarity	NPC205727
0.8626	High Similarity	NPC144418
0.8623	High Similarity	NPC117048
0.8623	High Similarity	NPC309953
0.8623	High Similarity	NPC124085
0.8621	High Similarity	NPC96294
0.8621	High Similarity	NPC93924
0.8613	High Similarity	NPC123954

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 NPC232246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	893
0.2-0.3	1827
0.3-0.4	2576
0.4-0.5	1945
0.5-0.6	1042
0.6-0.7	369
0.7-0.8	120
0.8-0.85	43
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8963	High Similarity	NPD5124	Phase 1
0.8963	High Similarity	NPD5123	Clinical (unspecified phase)
0.8921	High Similarity	NPD1652	Phase 2
0.8485	Intermediate Similarity	NPD422	Phase 1
0.8435	Intermediate Similarity	NPD1653	Approved
0.8278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1613	Approved
0.8214	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD7075	Discontinued
0.8092	Intermediate Similarity	NPD6801	Discontinued
0.8079	Intermediate Similarity	NPD4380	Phase 2
0.8071	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD2424	Discontinued
0.7943	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1610	Phase 2
0.7941	Intermediate Similarity	NPD1091	Approved
0.7929	Intermediate Similarity	NPD4908	Phase 1
0.7929	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD1548	Phase 1
0.7888	Intermediate Similarity	NPD5844	Phase 1
0.7885	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7819	Suspended
0.7806	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6799	Approved
0.7792	Intermediate Similarity	NPD7411	Suspended
0.777	Intermediate Similarity	NPD8651	Approved
0.7763	Intermediate Similarity	NPD5403	Approved
0.7748	Intermediate Similarity	NPD5401	Approved
0.7748	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3027	Phase 3
0.7718	Intermediate Similarity	NPD4628	Phase 3
0.7718	Intermediate Similarity	NPD3750	Approved
0.7708	Intermediate Similarity	NPD4060	Phase 1
0.7703	Intermediate Similarity	NPD1549	Phase 2
0.7692	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6798	Discontinued
0.7692	Intermediate Similarity	NPD1296	Phase 2
0.7687	Intermediate Similarity	NPD2796	Approved
0.7677	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4538	Approved
0.7671	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD7097	Phase 1
0.7671	Intermediate Similarity	NPD4536	Approved
0.7669	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD920	Approved
0.7643	Intermediate Similarity	NPD2415	Discontinued
0.7643	Intermediate Similarity	NPD5402	Approved
0.7643	Intermediate Similarity	NPD3817	Phase 2
0.7636	Intermediate Similarity	NPD6559	Discontinued
0.7635	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1934	Approved
0.7622	Intermediate Similarity	NPD4625	Phase 3
0.7619	Intermediate Similarity	NPD7033	Discontinued
0.7619	Intermediate Similarity	NPD3748	Approved
0.7616	Intermediate Similarity	NPD5058	Phase 3
0.7615	Intermediate Similarity	NPD1358	Approved
0.7615	Intermediate Similarity	NPD290	Approved
0.7613	Intermediate Similarity	NPD6599	Discontinued
0.7595	Intermediate Similarity	NPD7768	Phase 2
0.7589	Intermediate Similarity	NPD2797	Approved
0.758	Intermediate Similarity	NPD8455	Phase 2
0.7571	Intermediate Similarity	NPD4749	Approved
0.7557	Intermediate Similarity	NPD2684	Approved
0.7534	Intermediate Similarity	NPD4340	Discontinued
0.7534	Intermediate Similarity	NPD6355	Discontinued
0.7533	Intermediate Similarity	NPD1243	Approved
0.7518	Intermediate Similarity	NPD3225	Approved
0.7517	Intermediate Similarity	NPD5762	Approved
0.7517	Intermediate Similarity	NPD5763	Approved
0.7517	Intermediate Similarity	NPD6233	Phase 2
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD5960	Phase 3
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7549	Discontinued
0.7482	Intermediate Similarity	NPD3496	Discontinued
0.7468	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5691	Approved
0.7463	Intermediate Similarity	NPD5535	Approved
0.7463	Intermediate Similarity	NPD7843	Approved
0.7462	Intermediate Similarity	NPD9697	Approved
0.745	Intermediate Similarity	NPD1551	Phase 2
0.7448	Intermediate Similarity	NPD3268	Approved
0.7426	Intermediate Similarity	NPD7157	Approved
0.7421	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4626	Approved
0.7405	Intermediate Similarity	NPD4433	Discontinued
0.74	Intermediate Similarity	NPD7266	Discontinued
0.74	Intermediate Similarity	NPD6005	Phase 3
0.74	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6002	Phase 3
0.74	Intermediate Similarity	NPD6004	Phase 3
0.74	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3818	Discontinued
0.7391	Intermediate Similarity	NPD919	Approved
0.7383	Intermediate Similarity	NPD4308	Phase 3
0.7379	Intermediate Similarity	NPD7095	Approved
0.7378	Intermediate Similarity	NPD6166	Phase 2
0.7378	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2861	Phase 2
0.7358	Intermediate Similarity	NPD2801	Approved
0.7358	Intermediate Similarity	NPD1465	Phase 2
0.7351	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7054	Approved
0.7347	Intermediate Similarity	NPD4140	Approved
0.7346	Intermediate Similarity	NPD5494	Approved
0.7338	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD2935	Discontinued
0.7329	Intermediate Similarity	NPD2313	Discontinued
0.7325	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7472	Approved
0.7305	Intermediate Similarity	NPD7074	Phase 3
0.7303	Intermediate Similarity	NPD6674	Discontinued
0.7301	Intermediate Similarity	NPD7199	Phase 2
0.7296	Intermediate Similarity	NPD37	Approved
0.7286	Intermediate Similarity	NPD1778	Approved
0.7278	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3134	Approved
0.7273	Intermediate Similarity	NPD6667	Approved
0.7273	Intermediate Similarity	NPD6666	Approved
0.7267	Intermediate Similarity	NPD2799	Discontinued
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD6797	Phase 2
0.7254	Intermediate Similarity	NPD9717	Approved
0.7244	Intermediate Similarity	NPD1512	Approved
0.723	Intermediate Similarity	NPD4307	Phase 2
0.723	Intermediate Similarity	NPD1240	Approved
0.7226	Intermediate Similarity	NPD7212	Phase 2
0.7226	Intermediate Similarity	NPD7213	Phase 3
0.7222	Intermediate Similarity	NPD3749	Approved
0.7222	Intermediate Similarity	NPD3267	Approved
0.7222	Intermediate Similarity	NPD3266	Approved
0.7219	Intermediate Similarity	NPD7251	Discontinued
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7985	Registered
0.7195	Intermediate Similarity	NPD8127	Discontinued
0.7192	Intermediate Similarity	NPD6832	Phase 2
0.7183	Intermediate Similarity	NPD1611	Approved
0.7181	Intermediate Similarity	NPD447	Suspended
0.7181	Intermediate Similarity	NPD230	Phase 1
0.7179	Intermediate Similarity	NPD2534	Approved
0.7179	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD7447	Phase 1
0.7179	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2532	Approved
0.7178	Intermediate Similarity	NPD6234	Discontinued
0.7176	Intermediate Similarity	NPD7808	Phase 3
0.7174	Intermediate Similarity	NPD6671	Approved
0.7172	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4062	Phase 3
0.716	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4535	Phase 3
0.7133	Intermediate Similarity	NPD1607	Approved
0.7133	Intermediate Similarity	NPD6653	Approved
0.7108	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6100	Approved
0.7105	Intermediate Similarity	NPD6032	Approved
0.7105	Intermediate Similarity	NPD6099	Approved
0.7104	Intermediate Similarity	NPD7583	Approved
0.7103	Intermediate Similarity	NPD987	Approved
0.7103	Intermediate Similarity	NPD1203	Approved
0.7097	Intermediate Similarity	NPD6190	Approved
0.7095	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1048	Approved
0.7091	Intermediate Similarity	NPD6959	Discontinued
0.7083	Intermediate Similarity	NPD7228	Approved
0.7083	Intermediate Similarity	NPD3751	Discontinued
0.7065	Intermediate Similarity	NPD7585	Approved
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.7055	Intermediate Similarity	NPD3691	Phase 2
0.7055	Intermediate Similarity	NPD3690	Phase 2
0.7055	Intermediate Similarity	NPD1019	Discontinued
0.7048	Intermediate Similarity	NPD3787	Discontinued
0.7042	Intermediate Similarity	NPD5846	Approved
0.7042	Intermediate Similarity	NPD6516	Phase 2
0.7029	Intermediate Similarity	NPD1241	Discontinued
0.7025	Intermediate Similarity	NPD6273	Approved
0.7025	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5049	Phase 3
0.7024	Intermediate Similarity	NPD7473	Discontinued
0.7014	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD3018	Phase 2

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