NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	261.669
LogP:	2.453
LogD:	2.376
LogS:	-4.163
# Rotatable Bonds:	3
TPSA:	51.97
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.482
Synthetic Accessibility Score:	3.469
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	1.6992713426589034e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.251

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	82.92378997802734%
Volume Distribution (VD):	1.26
Pgp-substrate:	14.831121444702148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.68
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.422
CYP2C19-substrate:	0.602
CYP2C9-inhibitor:	0.237
CYP2C9-substrate:	0.334
CYP2D6-inhibitor:	0.675
CYP2D6-substrate:	0.773
CYP3A4-inhibitor:	0.324
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	8.374
Half-life (T1/2):	0.375

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.649
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.334
Skin Sensitization:	0.084
Carcinogencity:	0.907
Eye Corrosion:	0.004
Eye Irritation:	0.139
Respiratory Toxicity:	0.691

Download Data

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

Natural Product: NPC199204

Natural Product ID:	NPC199204
*Common Name:**	Phebalosin
IUPAC Name:	7-methoxy-8-[(2R,3R)-3-prop-1-en-2-yloxiran-2-yl]chromen-2-one
Synonyms:	Phebalosin
Standard InCHIKey:	YTDNHMHONBWCBV-UKRRQHHQSA-N
Standard InCHI:	InChI=1S/C15H14O4/c1-8(2)13-15(19-13)12-10(17-3)6-4-9-5-7-11(16)18-14(9)12/h4-7,13,15H,1H2,2-3H3/t13-,15-/m1/s1
SMILES:	COc1ccc2c(c1[C@H]1O[C@@H]1C(=C)C)oc(=O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486409
PubChem CID:	188300
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO5744	Galipea panamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20423106]
NPO26959	Micromelum minutum	Species	Rutaceae	Eukaryota	Barks	n.a.	n.a.	PMID[3754570]
NPO26959	Micromelum minutum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5744	Galipea panamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26959	Micromelum minutum	Species	Rutaceae	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
ED50	2
Others	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	CC50	=	20.7	ug.mL-1	PMID[516705]
NPT140	Organism	Artemia	Artemia	LC50	=	47.0	ppm	PMID[516704]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Activity	=	-70.0	%	PMID[516704]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[516704]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	27.0	ug ml-1	PMID[516704]
NPT2	Others	Unspecified		Selectivity Index	=	1.5	n.a.	PMID[516705]

☑ 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 NPC199204 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	436
0.1-0.2	1908
0.2-0.3	5086
0.3-0.4	10788
0.4-0.5	7319
0.5-0.6	4751
0.6-0.7	5801
0.7-0.8	5210
0.8-0.85	1043
0.85-0.9	231
0.9-0.95	120
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9837	High Similarity	NPC80170
0.9597	High Similarity	NPC168710
0.9512	High Similarity	NPC188327
0.9512	High Similarity	NPC234109
0.9453	High Similarity	NPC469675
0.9426	High Similarity	NPC472518
0.937	High Similarity	NPC194277
0.935	High Similarity	NPC201667
0.935	High Similarity	NPC73413
0.9344	High Similarity	NPC96286
0.9344	High Similarity	NPC248429
0.9297	High Similarity	NPC31849
0.9297	High Similarity	NPC163557
0.9297	High Similarity	NPC133956
0.9297	High Similarity	NPC296624
0.9297	High Similarity	NPC318400
0.9297	High Similarity	NPC471910
0.9297	High Similarity	NPC167111
0.9297	High Similarity	NPC207002
0.9274	High Similarity	NPC471828
0.9274	High Similarity	NPC471827
0.9268	High Similarity	NPC273772
0.9268	High Similarity	NPC109675
0.9262	High Similarity	NPC144418
0.9225	High Similarity	NPC326600
0.9225	High Similarity	NPC47163
0.9225	High Similarity	NPC62366
0.9225	High Similarity	NPC18804
0.9225	High Similarity	NPC84894
0.9225	High Similarity	NPC319859
0.9225	High Similarity	NPC166672
0.9225	High Similarity	NPC267412
0.9225	High Similarity	NPC260265
0.9225	High Similarity	NPC204353
0.9225	High Similarity	NPC74655
0.9225	High Similarity	NPC50896
0.9225	High Similarity	NPC55149
0.9225	High Similarity	NPC307412
0.9225	High Similarity	NPC164269
0.9225	High Similarity	NPC198381
0.9225	High Similarity	NPC195343
0.9225	High Similarity	NPC127888
0.9225	High Similarity	NPC100986
0.9225	High Similarity	NPC287182
0.9219	High Similarity	NPC14248
0.9206	High Similarity	NPC185066
0.9206	High Similarity	NPC472519
0.92	High Similarity	NPC471826
0.9194	High Similarity	NPC27671
0.9194	High Similarity	NPC111347
0.918	High Similarity	NPC163200
0.9174	High Similarity	NPC298796
0.9174	High Similarity	NPC281356
0.9154	High Similarity	NPC472424
0.9154	High Similarity	NPC86892
0.9154	High Similarity	NPC471625
0.9154	High Similarity	NPC471909
0.9154	High Similarity	NPC33986
0.9154	High Similarity	NPC281241
0.9147	High Similarity	NPC222036
0.9147	High Similarity	NPC7526
0.9113	High Similarity	NPC173350
0.9113	High Similarity	NPC154176
0.9113	High Similarity	NPC290605
0.9091	High Similarity	NPC96705
0.9091	High Similarity	NPC152306
0.9091	High Similarity	NPC265547
0.9084	High Similarity	NPC78746
0.9084	High Similarity	NPC160727
0.9084	High Similarity	NPC128529
0.9084	High Similarity	NPC177281
0.9084	High Similarity	NPC283019
0.9084	High Similarity	NPC149320
0.9084	High Similarity	NPC471630
0.9084	High Similarity	NPC55615
0.9084	High Similarity	NPC188380
0.9084	High Similarity	NPC38099
0.9084	High Similarity	NPC224543
0.9084	High Similarity	NPC26954
0.9084	High Similarity	NPC476455
0.9077	High Similarity	NPC224475
0.9077	High Similarity	NPC98179
0.9077	High Similarity	NPC180716
0.9077	High Similarity	NPC253574
0.9077	High Similarity	NPC213173
0.907	High Similarity	NPC19157
0.9032	High Similarity	NPC257188
0.9032	High Similarity	NPC13007
0.9024	High Similarity	NPC235190
0.9024	High Similarity	NPC180006
0.9015	High Similarity	NPC232246
0.9015	High Similarity	NPC153818
0.9015	High Similarity	NPC294456
0.9015	High Similarity	NPC281014
0.9015	High Similarity	NPC212124
0.9015	High Similarity	NPC225106
0.9015	High Similarity	NPC184861
0.9015	High Similarity	NPC155963
0.9008	High Similarity	NPC472525
0.8968	High Similarity	NPC93219
0.8968	High Similarity	NPC244495
0.8963	High Similarity	NPC119640
0.8963	High Similarity	NPC183646
0.896	High Similarity	NPC315807
0.8947	High Similarity	NPC279573
0.8947	High Similarity	NPC151946
0.8947	High Similarity	NPC211110
0.8939	High Similarity	NPC283331
0.8926	High Similarity	NPC128633
0.8923	High Similarity	NPC175159
0.8897	High Similarity	NPC476457
0.8889	High Similarity	NPC291899
0.8881	High Similarity	NPC312881
0.8855	High Similarity	NPC55147
0.8846	High Similarity	NPC472517
0.8832	High Similarity	NPC76657
0.8828	High Similarity	NPC258567
0.8828	High Similarity	NPC243688
0.8828	High Similarity	NPC121740
0.8828	High Similarity	NPC224774
0.8815	High Similarity	NPC287286
0.8815	High Similarity	NPC152771
0.8815	High Similarity	NPC195357
0.881	High Similarity	NPC50720
0.8779	High Similarity	NPC469956
0.8769	High Similarity	NPC113098
0.876	High Similarity	NPC139595
0.876	High Similarity	NPC60704
0.876	High Similarity	NPC469453
0.876	High Similarity	NPC293642
0.875	High Similarity	NPC101894
0.8731	High Similarity	NPC306365
0.8731	High Similarity	NPC14697
0.873	High Similarity	NPC150214
0.8712	High Similarity	NPC469952
0.8712	High Similarity	NPC54503
0.8712	High Similarity	NPC469955
0.8712	High Similarity	NPC472524
0.8702	High Similarity	NPC29734
0.8702	High Similarity	NPC267336
0.8702	High Similarity	NPC272650
0.8682	High Similarity	NPC289316
0.8667	High Similarity	NPC270256
0.8657	High Similarity	NPC167517
0.8651	High Similarity	NPC52247
0.8651	High Similarity	NPC187868
0.8647	High Similarity	NPC309953
0.8636	High Similarity	NPC137669
0.8636	High Similarity	NPC123954
0.8626	High Similarity	NPC244799
0.8626	High Similarity	NPC32463
0.8626	High Similarity	NPC240722
0.8626	High Similarity	NPC19242
0.8623	High Similarity	NPC471824
0.8615	High Similarity	NPC157212
0.8605	High Similarity	NPC163248
0.8593	High Similarity	NPC472516
0.8593	High Similarity	NPC131198
0.8582	High Similarity	NPC229128
0.8571	High Similarity	NPC472522
0.8571	High Similarity	NPC302107
0.8571	High Similarity	NPC241341
0.8571	High Similarity	NPC319378
0.8571	High Similarity	NPC233018
0.8571	High Similarity	NPC2363
0.8571	High Similarity	NPC36437
0.8571	High Similarity	NPC469449
0.8561	High Similarity	NPC250727
0.8561	High Similarity	NPC85624
0.8561	High Similarity	NPC469701
0.8551	High Similarity	NPC229916
0.855	High Similarity	NPC123127
0.855	High Similarity	NPC27239
0.854	High Similarity	NPC138149
0.854	High Similarity	NPC472523
0.8529	High Similarity	NPC307883
0.8527	High Similarity	NPC202594
0.8527	High Similarity	NPC168259
0.8527	High Similarity	NPC232692
0.8519	High Similarity	NPC104796
0.8516	High Similarity	NPC143725
0.8507	High Similarity	NPC131950
0.85	High Similarity	NPC205361
0.8496	Intermediate Similarity	NPC319969
0.8492	Intermediate Similarity	NPC473290
0.8492	Intermediate Similarity	NPC471504
0.8492	Intermediate Similarity	NPC247553
0.8489	Intermediate Similarity	NPC471763
0.8478	Intermediate Similarity	NPC93640
0.8478	Intermediate Similarity	NPC20631
0.8478	Intermediate Similarity	NPC470856
0.8467	Intermediate Similarity	NPC36414
0.8456	Intermediate Similarity	NPC471069
0.8456	Intermediate Similarity	NPC471068
0.8444	Intermediate Similarity	NPC234865
0.8444	Intermediate Similarity	NPC61499
0.844	Intermediate Similarity	NPC296377
0.844	Intermediate Similarity	NPC471764
0.844	Intermediate Similarity	NPC87950
0.8433	Intermediate Similarity	NPC205797

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 NPC199204 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	1013
0.2-0.3	1824
0.3-0.4	2741
0.4-0.5	1812
0.5-0.6	943
0.6-0.7	291
0.7-0.8	103
0.8-0.85	21
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8651	High Similarity	NPD422	Phase 1
0.8433	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8433	Intermediate Similarity	NPD5124	Phase 1
0.8333	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1296	Phase 2
0.8143	Intermediate Similarity	NPD1652	Phase 2
0.8125	Intermediate Similarity	NPD920	Approved
0.8017	Intermediate Similarity	NPD9697	Approved
0.8014	Intermediate Similarity	NPD1243	Approved
0.7986	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3748	Approved
0.7972	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2796	Approved
0.7907	Intermediate Similarity	NPD1548	Phase 1
0.7846	Intermediate Similarity	NPD5691	Approved
0.781	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD1610	Phase 2
0.7742	Intermediate Similarity	NPD1358	Approved
0.7717	Intermediate Similarity	NPD5535	Approved
0.7708	Intermediate Similarity	NPD3750	Approved
0.7703	Intermediate Similarity	NPD1653	Approved
0.7687	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1611	Approved
0.7664	Intermediate Similarity	NPD4908	Phase 1
0.7661	Intermediate Similarity	NPD3134	Approved
0.7619	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6801	Discontinued
0.7597	Intermediate Similarity	NPD919	Approved
0.7594	Intermediate Similarity	NPD3496	Discontinued
0.7574	Intermediate Similarity	NPD3267	Approved
0.7574	Intermediate Similarity	NPD3266	Approved
0.7571	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1613	Approved
0.7569	Intermediate Similarity	NPD1549	Phase 2
0.7566	Intermediate Similarity	NPD7819	Suspended
0.7552	Intermediate Similarity	NPD1551	Phase 2
0.7551	Intermediate Similarity	NPD6799	Approved
0.755	Intermediate Similarity	NPD7411	Suspended
0.755	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD6832	Phase 2
0.7532	Intermediate Similarity	NPD7075	Discontinued
0.7519	Intermediate Similarity	NPD1241	Discontinued
0.7519	Intermediate Similarity	NPD4626	Approved
0.7518	Intermediate Similarity	NPD1019	Discontinued
0.7517	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3225	Approved
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1510	Phase 2
0.7468	Intermediate Similarity	NPD7768	Phase 2
0.7466	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4307	Phase 2
0.7445	Intermediate Similarity	NPD2797	Approved
0.7417	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5401	Approved
0.7368	Intermediate Similarity	NPD4380	Phase 2
0.7368	Intermediate Similarity	NPD6599	Discontinued
0.7353	Intermediate Similarity	NPD9717	Approved
0.7347	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5844	Phase 1
0.7329	Intermediate Similarity	NPD2424	Discontinued
0.7324	Intermediate Similarity	NPD4060	Phase 1
0.7324	Intermediate Similarity	NPD1240	Approved
0.731	Intermediate Similarity	NPD2935	Discontinued
0.7305	Intermediate Similarity	NPD3268	Approved
0.7305	Intermediate Similarity	NPD2313	Discontinued
0.729	Intermediate Similarity	NPD3817	Phase 2
0.7285	Intermediate Similarity	NPD5403	Approved
0.7279	Intermediate Similarity	NPD1091	Approved
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6004	Phase 3
0.726	Intermediate Similarity	NPD6005	Phase 3
0.726	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6002	Phase 3
0.726	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD17	Approved
0.7259	Intermediate Similarity	NPD1778	Approved
0.7246	Intermediate Similarity	NPD8651	Approved
0.7244	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7033	Discontinued
0.7241	Intermediate Similarity	NPD4308	Phase 3
0.7241	Intermediate Similarity	NPD2799	Discontinued
0.7234	Intermediate Similarity	NPD3027	Phase 3
0.7234	Intermediate Similarity	NPD4625	Phase 3
0.723	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD1607	Approved
0.7219	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5494	Approved
0.7197	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1203	Approved
0.7188	Intermediate Similarity	NPD290	Approved
0.7185	Intermediate Similarity	NPD5585	Approved
0.7183	Intermediate Similarity	NPD6798	Discontinued
0.7183	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5402	Approved
0.7179	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4749	Approved
0.717	Intermediate Similarity	NPD1247	Approved
0.7161	Intermediate Similarity	NPD1934	Approved
0.7153	Intermediate Similarity	NPD4340	Discontinued
0.7153	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD2533	Approved
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6667	Approved
0.7133	Intermediate Similarity	NPD6666	Approved
0.7132	Intermediate Similarity	NPD2684	Approved
0.7101	Intermediate Similarity	NPD1608	Approved
0.7092	Intermediate Similarity	NPD2861	Phase 2
0.7086	Intermediate Similarity	NPD1511	Approved
0.7083	Intermediate Similarity	NPD4140	Approved
0.707	Intermediate Similarity	NPD4288	Approved
0.7063	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7097	Phase 1
0.7047	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2800	Approved
0.7045	Intermediate Similarity	NPD7843	Approved
0.7034	Intermediate Similarity	NPD447	Suspended
0.7034	Intermediate Similarity	NPD230	Phase 1
0.7029	Intermediate Similarity	NPD1281	Approved
0.7027	Intermediate Similarity	NPD5763	Approved
0.7027	Intermediate Similarity	NPD5762	Approved
0.7027	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7229	Phase 3
0.7015	Intermediate Similarity	NPD7157	Approved
0.7014	Intermediate Similarity	NPD6233	Phase 2
0.7012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1512	Approved
0.6988	Remote Similarity	NPD6559	Discontinued
0.6985	Remote Similarity	NPD9545	Approved
0.6985	Remote Similarity	NPD1894	Discontinued
0.6981	Remote Similarity	NPD3749	Approved
0.6974	Remote Similarity	NPD7213	Phase 3
0.6974	Remote Similarity	NPD7212	Phase 2
0.6974	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2237	Approved
0.6972	Remote Similarity	NPD3018	Phase 2
0.6968	Remote Similarity	NPD3226	Approved
0.6966	Remote Similarity	NPD2979	Phase 3
0.6959	Remote Similarity	NPD4477	Approved
0.6959	Remote Similarity	NPD4476	Approved
0.6948	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7549	Discontinued
0.6944	Remote Similarity	NPD411	Approved
0.6939	Remote Similarity	NPD4536	Approved
0.6939	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4538	Approved
0.6929	Remote Similarity	NPD4359	Approved
0.6929	Remote Similarity	NPD940	Approved
0.6929	Remote Similarity	NPD846	Approved
0.6928	Remote Similarity	NPD7447	Phase 1
0.6928	Remote Similarity	NPD5953	Discontinued
0.6918	Remote Similarity	NPD1933	Approved
0.6913	Remote Similarity	NPD2346	Discontinued
0.6912	Remote Similarity	NPD7644	Approved
0.6909	Remote Similarity	NPD7286	Phase 2
0.6906	Remote Similarity	NPD1535	Discovery
0.6901	Remote Similarity	NPD3690	Phase 2
0.6901	Remote Similarity	NPD3691	Phase 2
0.6899	Remote Similarity	NPD2801	Approved
0.6899	Remote Similarity	NPD8455	Phase 2
0.6899	Remote Similarity	NPD1465	Phase 2
0.6892	Remote Similarity	NPD5960	Phase 3
0.6889	Remote Similarity	NPD6671	Approved
0.6887	Remote Similarity	NPD7466	Approved
0.6879	Remote Similarity	NPD1283	Approved
0.6859	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2981	Phase 2
0.6857	Remote Similarity	NPD1481	Phase 2
0.6855	Remote Similarity	NPD2415	Discontinued
0.6852	Remote Similarity	NPD6959	Discontinued
0.6848	Remote Similarity	NPD3818	Discontinued
0.6846	Remote Similarity	NPD2438	Suspended
0.6846	Remote Similarity	NPD968	Approved
0.6846	Remote Similarity	NPD6032	Approved
0.6842	Remote Similarity	NPD1139	Approved
0.6842	Remote Similarity	NPD1137	Approved
0.6835	Remote Similarity	NPD37	Approved
0.6835	Remote Similarity	NPD3847	Discontinued
0.6831	Remote Similarity	NPD987	Approved
0.6828	Remote Similarity	NPD1048	Approved
0.6824	Remote Similarity	NPD2200	Suspended
0.6818	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4966	Approved
0.6813	Remote Similarity	NPD3882	Suspended
0.6813	Remote Similarity	NPD4967	Phase 2
0.6813	Remote Similarity	NPD4965	Approved
0.6812	Remote Similarity	NPD1651	Approved
0.681	Remote Similarity	NPD6232	Discontinued
0.6809	Remote Similarity	NPD2983	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