NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	198.09
Volume:	194.291
LogP:	0.935
LogD:	0.831
LogS:	-1.318
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.419
Synthetic Accessibility Score:	4.571
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.626
MDCK Permeability:	0.000803451519459486
Pgp-inhibitor:	0.0
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.154

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.883
Plasma Protein Binding (PPB):	25.59903335571289%
Volume Distribution (VD):	0.632
Pgp-substrate:	78.99628448486328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.246
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.53
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	8.709
Half-life (T1/2):	0.478

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.261
AMES Toxicity:	0.679
Rat Oral Acute Toxicity:	0.885
Maximum Recommended Daily Dose:	0.71
Skin Sensitization:	0.356
Carcinogencity:	0.921
Eye Corrosion:	0.576
Eye Irritation:	0.339
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC246173

Natural Product ID:	NPC246173
*Common Name:**	Jatamanin A
IUPAC Name:	(4aS,6S,7S,7aS)-6,7-dihydroxy-7-methyl-4-methylidene-4a,5,6,7a-tetrahydrocyclopenta[c]pyran-1-one
Synonyms:
Standard InCHIKey:	LDGOKVOMVZXPJV-IBCQBUCCSA-N
Standard InCHI:	InChI=1S/C10H14O4/c1-5-4-14-9(12)8-6(5)3-7(11)10(8,2)13/h6-8,11,13H,1,3-4H2,2H3/t6-,7+,8-,10-/m1/s1
SMILES:	C=C1COC(=O)[C@H]2[C@@H]1C[C@@H]([C@@]2(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094288
PubChem CID:	46211034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245261]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20151678]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23002924]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29799195]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	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
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[464085]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	27770.0	nM	PMID[464086]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[464085]

☑ 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 NPC246173 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	193
0.1-0.2	1510
0.2-0.3	5640
0.3-0.4	11184
0.4-0.5	11267
0.5-0.6	7160
0.6-0.7	4927
0.7-0.8	799
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC471381
0.8316	Intermediate Similarity	NPC471150
0.8316	Intermediate Similarity	NPC311904
0.8298	Intermediate Similarity	NPC472873
0.8235	Intermediate Similarity	NPC214030
0.8235	Intermediate Similarity	NPC83108
0.8152	Intermediate Similarity	NPC215556
0.8144	Intermediate Similarity	NPC186861
0.8119	Intermediate Similarity	NPC110701
0.81	Intermediate Similarity	NPC170432
0.8081	Intermediate Similarity	NPC37240
0.8065	Intermediate Similarity	NPC216284
0.8043	Intermediate Similarity	NPC79549
0.8021	Intermediate Similarity	NPC91771
0.8021	Intermediate Similarity	NPC142529
0.802	Intermediate Similarity	NPC197813
0.802	Intermediate Similarity	NPC80338
0.802	Intermediate Similarity	NPC148270
0.798	Intermediate Similarity	NPC177013
0.798	Intermediate Similarity	NPC35185
0.798	Intermediate Similarity	NPC474730
0.798	Intermediate Similarity	NPC4899
0.7979	Intermediate Similarity	NPC184063
0.7961	Intermediate Similarity	NPC193741
0.7938	Intermediate Similarity	NPC474313
0.7921	Intermediate Similarity	NPC44004
0.7921	Intermediate Similarity	NPC54737
0.7917	Intermediate Similarity	NPC163228
0.79	Intermediate Similarity	NPC475928
0.7895	Intermediate Similarity	NPC153590
0.7895	Intermediate Similarity	NPC200237
0.7895	Intermediate Similarity	NPC475788
0.7889	Intermediate Similarity	NPC111409
0.7879	Intermediate Similarity	NPC67296
0.7872	Intermediate Similarity	NPC19087
0.7857	Intermediate Similarity	NPC45125
0.7849	Intermediate Similarity	NPC178875
0.7835	Intermediate Similarity	NPC170527
0.7835	Intermediate Similarity	NPC476009
0.781	Intermediate Similarity	NPC475924
0.781	Intermediate Similarity	NPC475851
0.7789	Intermediate Similarity	NPC235051
0.7789	Intermediate Similarity	NPC155215
0.7778	Intermediate Similarity	NPC280963
0.7766	Intermediate Similarity	NPC38392
0.7766	Intermediate Similarity	NPC155935
0.7755	Intermediate Similarity	NPC236580
0.7755	Intermediate Similarity	NPC304445
0.7755	Intermediate Similarity	NPC181151
0.7745	Intermediate Similarity	NPC127235
0.7742	Intermediate Similarity	NPC118601
0.7742	Intermediate Similarity	NPC186148
0.7732	Intermediate Similarity	NPC52044
0.7732	Intermediate Similarity	NPC6765
0.7732	Intermediate Similarity	NPC475900
0.7732	Intermediate Similarity	NPC476053
0.7732	Intermediate Similarity	NPC93869
0.7723	Intermediate Similarity	NPC474775
0.7717	Intermediate Similarity	NPC284534
0.7717	Intermediate Similarity	NPC204105
0.7717	Intermediate Similarity	NPC300082
0.7708	Intermediate Similarity	NPC473263
0.7708	Intermediate Similarity	NPC258216
0.7708	Intermediate Similarity	NPC473273
0.7708	Intermediate Similarity	NPC473234
0.7708	Intermediate Similarity	NPC308656
0.7708	Intermediate Similarity	NPC60386
0.77	Intermediate Similarity	NPC3488
0.77	Intermediate Similarity	NPC287539
0.77	Intermediate Similarity	NPC39683
0.77	Intermediate Similarity	NPC471767
0.77	Intermediate Similarity	NPC150923
0.77	Intermediate Similarity	NPC171759
0.7692	Intermediate Similarity	NPC128246
0.7692	Intermediate Similarity	NPC139838
0.7692	Intermediate Similarity	NPC59489
0.7684	Intermediate Similarity	NPC54065
0.7684	Intermediate Similarity	NPC297474
0.7684	Intermediate Similarity	NPC35809
0.766	Intermediate Similarity	NPC217983
0.766	Intermediate Similarity	NPC202672
0.766	Intermediate Similarity	NPC58219
0.766	Intermediate Similarity	NPC177629
0.766	Intermediate Similarity	NPC207114
0.7653	Intermediate Similarity	NPC470883
0.7653	Intermediate Similarity	NPC76862
0.7653	Intermediate Similarity	NPC158416
0.7653	Intermediate Similarity	NPC39859
0.7642	Intermediate Similarity	NPC126691
0.7634	Intermediate Similarity	NPC309757
0.7634	Intermediate Similarity	NPC236692
0.7634	Intermediate Similarity	NPC475019
0.7634	Intermediate Similarity	NPC474949
0.7634	Intermediate Similarity	NPC187661
0.7634	Intermediate Similarity	NPC470242
0.7629	Intermediate Similarity	NPC473331
0.7629	Intermediate Similarity	NPC274588
0.7624	Intermediate Similarity	NPC106668
0.7624	Intermediate Similarity	NPC49393
0.7624	Intermediate Similarity	NPC250594
0.7624	Intermediate Similarity	NPC80144
0.7619	Intermediate Similarity	NPC41551
0.7619	Intermediate Similarity	NPC475062
0.7619	Intermediate Similarity	NPC50223
0.7609	Intermediate Similarity	NPC474780
0.7604	Intermediate Similarity	NPC293001
0.7604	Intermediate Similarity	NPC171360
0.7604	Intermediate Similarity	NPC191339
0.7604	Intermediate Similarity	NPC184463
0.7604	Intermediate Similarity	NPC329952
0.7604	Intermediate Similarity	NPC29821
0.7604	Intermediate Similarity	NPC133888
0.7604	Intermediate Similarity	NPC63193
0.7604	Intermediate Similarity	NPC35959
0.7604	Intermediate Similarity	NPC70251
0.7604	Intermediate Similarity	NPC475881
0.7604	Intermediate Similarity	NPC286341
0.7604	Intermediate Similarity	NPC57304
0.76	Intermediate Similarity	NPC70865
0.7596	Intermediate Similarity	NPC117604
0.7593	Intermediate Similarity	NPC277583
0.7579	Intermediate Similarity	NPC12872
0.7579	Intermediate Similarity	NPC92974
0.7579	Intermediate Similarity	NPC168679
0.7576	Intermediate Similarity	NPC58267
0.7576	Intermediate Similarity	NPC161493
0.7576	Intermediate Similarity	NPC261372
0.7576	Intermediate Similarity	NPC40812
0.7576	Intermediate Similarity	NPC263674
0.7576	Intermediate Similarity	NPC472290
0.7573	Intermediate Similarity	NPC474101
0.7573	Intermediate Similarity	NPC295366
0.7556	Intermediate Similarity	NPC156658
0.7556	Intermediate Similarity	NPC258965
0.7556	Intermediate Similarity	NPC476625
0.7553	Intermediate Similarity	NPC270270
0.7553	Intermediate Similarity	NPC190753
0.7551	Intermediate Similarity	NPC37408
0.7551	Intermediate Similarity	NPC67584
0.7551	Intermediate Similarity	NPC170120
0.7551	Intermediate Similarity	NPC213698
0.7549	Intermediate Similarity	NPC27687
0.7547	Intermediate Similarity	NPC94650
0.7527	Intermediate Similarity	NPC329749
0.7527	Intermediate Similarity	NPC47958
0.7527	Intermediate Similarity	NPC304509
0.7527	Intermediate Similarity	NPC149725
0.7526	Intermediate Similarity	NPC475912
0.7526	Intermediate Similarity	NPC212486
0.7525	Intermediate Similarity	NPC477950
0.75	Intermediate Similarity	NPC245665
0.75	Intermediate Similarity	NPC187761
0.75	Intermediate Similarity	NPC249171
0.75	Intermediate Similarity	NPC65359
0.75	Intermediate Similarity	NPC49833
0.75	Intermediate Similarity	NPC83895
0.75	Intermediate Similarity	NPC470188
0.7477	Intermediate Similarity	NPC40608
0.7476	Intermediate Similarity	NPC309190
0.7476	Intermediate Similarity	NPC100487
0.7475	Intermediate Similarity	NPC126156
0.7475	Intermediate Similarity	NPC213078
0.7475	Intermediate Similarity	NPC474297
0.7473	Intermediate Similarity	NPC126248
0.7455	Intermediate Similarity	NPC475401
0.7453	Intermediate Similarity	NPC124053
0.7451	Intermediate Similarity	NPC304163
0.7451	Intermediate Similarity	NPC170615
0.7451	Intermediate Similarity	NPC105725
0.7451	Intermediate Similarity	NPC474747
0.7451	Intermediate Similarity	NPC475986
0.7449	Intermediate Similarity	NPC190294
0.7449	Intermediate Similarity	NPC71589
0.7449	Intermediate Similarity	NPC127019
0.7447	Intermediate Similarity	NPC56593
0.7447	Intermediate Similarity	NPC476015
0.7447	Intermediate Similarity	NPC474762
0.7447	Intermediate Similarity	NPC304558
0.7429	Intermediate Similarity	NPC68248
0.7423	Intermediate Similarity	NPC469627
0.7423	Intermediate Similarity	NPC131209
0.7423	Intermediate Similarity	NPC12172
0.7423	Intermediate Similarity	NPC208886
0.7423	Intermediate Similarity	NPC30515
0.7423	Intermediate Similarity	NPC475925
0.7419	Intermediate Similarity	NPC194859
0.7419	Intermediate Similarity	NPC3464
0.7419	Intermediate Similarity	NPC475963
0.7419	Intermediate Similarity	NPC224386
0.7419	Intermediate Similarity	NPC151176
0.7412	Intermediate Similarity	NPC98711
0.7407	Intermediate Similarity	NPC9848
0.7407	Intermediate Similarity	NPC312017
0.7404	Intermediate Similarity	NPC243998
0.7404	Intermediate Similarity	NPC179891
0.74	Intermediate Similarity	NPC213947
0.74	Intermediate Similarity	NPC108475
0.74	Intermediate Similarity	NPC477949
0.74	Intermediate Similarity	NPC170143
0.7396	Intermediate Similarity	NPC307411

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 NPC246173 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	2188
0.2-0.3	3832
0.3-0.4	1917
0.4-0.5	557
0.5-0.6	318
0.6-0.7	146
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.717	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6371	Approved
0.7021	Intermediate Similarity	NPD6435	Approved
0.7	Intermediate Similarity	NPD6053	Discontinued
0.697	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD46	Approved
0.6944	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5369	Approved
0.6907	Remote Similarity	NPD5786	Approved
0.69	Remote Similarity	NPD7983	Approved
0.687	Remote Similarity	NPD6319	Approved
0.6869	Remote Similarity	NPD1695	Approved
0.6863	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7319	Approved
0.6809	Remote Similarity	NPD5368	Approved
0.6804	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8133	Approved
0.6723	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6634	Remote Similarity	NPD5785	Approved
0.6633	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5362	Discontinued
0.6596	Remote Similarity	NPD4802	Phase 2
0.6596	Remote Similarity	NPD4238	Approved
0.6566	Remote Similarity	NPD4249	Approved
0.6535	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6101	Approved
0.6525	Remote Similarity	NPD8516	Approved
0.6525	Remote Similarity	NPD8517	Approved
0.6525	Remote Similarity	NPD8515	Approved
0.6525	Remote Similarity	NPD8513	Phase 3
0.6518	Remote Similarity	NPD4634	Approved
0.6514	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4251	Approved
0.65	Remote Similarity	NPD4250	Approved
0.65	Remote Similarity	NPD7492	Approved
0.6491	Remote Similarity	NPD4632	Approved
0.6486	Remote Similarity	NPD6686	Approved
0.6465	Remote Similarity	NPD5363	Approved
0.646	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4819	Approved
0.6458	Remote Similarity	NPD4822	Approved
0.6458	Remote Similarity	NPD4821	Approved
0.6458	Remote Similarity	NPD4252	Approved
0.6458	Remote Similarity	NPD4820	Approved
0.6458	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6675	Approved
0.6455	Remote Similarity	NPD6402	Approved
0.6455	Remote Similarity	NPD5739	Approved
0.6455	Remote Similarity	NPD7128	Approved
0.6446	Remote Similarity	NPD6616	Approved
0.6442	Remote Similarity	NPD5282	Discontinued
0.6441	Remote Similarity	NPD6059	Approved
0.6441	Remote Similarity	NPD6054	Approved
0.6429	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD6373	Approved
0.6408	Remote Similarity	NPD6411	Approved
0.6396	Remote Similarity	NPD5697	Approved
0.6396	Remote Similarity	NPD5701	Approved
0.6396	Remote Similarity	NPD6412	Phase 2
0.6393	Remote Similarity	NPD7078	Approved
0.6393	Remote Similarity	NPD8293	Discontinued
0.6389	Remote Similarity	NPD1700	Approved
0.6387	Remote Similarity	NPD6016	Approved
0.6387	Remote Similarity	NPD6015	Approved
0.6355	Remote Similarity	NPD7638	Approved
0.6341	Remote Similarity	NPD7736	Approved
0.6339	Remote Similarity	NPD6881	Approved
0.6339	Remote Similarity	NPD6899	Approved
0.6339	Remote Similarity	NPD7320	Approved
0.6333	Remote Similarity	NPD6370	Approved
0.6333	Remote Similarity	NPD5988	Approved
0.6325	Remote Similarity	NPD7115	Discovery
0.6321	Remote Similarity	NPD7839	Suspended
0.6316	Remote Similarity	NPD6649	Approved
0.6316	Remote Similarity	NPD6650	Approved
0.6306	Remote Similarity	NPD6008	Approved
0.6296	Remote Similarity	NPD7639	Approved
0.6296	Remote Similarity	NPD7640	Approved
0.6283	Remote Similarity	NPD6014	Approved
0.6283	Remote Similarity	NPD6013	Approved
0.6283	Remote Similarity	NPD6012	Approved
0.6263	Remote Similarity	NPD7154	Phase 3
0.6262	Remote Similarity	NPD6083	Phase 2
0.6262	Remote Similarity	NPD6084	Phase 2
0.6261	Remote Similarity	NPD8297	Approved
0.626	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD4271	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD6921	Approved
0.625	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD8034	Phase 2
0.6228	Remote Similarity	NPD7102	Approved
0.6228	Remote Similarity	NPD7290	Approved
0.6228	Remote Similarity	NPD6883	Approved
0.6226	Remote Similarity	NPD5695	Phase 3
0.6204	Remote Similarity	NPD5696	Approved
0.6204	Remote Similarity	NPD4225	Approved
0.6195	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD6399	Phase 3
0.6186	Remote Similarity	NPD6009	Approved
0.6174	Remote Similarity	NPD6869	Approved
0.6174	Remote Similarity	NPD6847	Approved
0.6174	Remote Similarity	NPD6617	Approved
0.6174	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD7838	Discovery
0.614	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7327	Approved
0.6134	Remote Similarity	NPD7328	Approved
0.6121	Remote Similarity	NPD6882	Approved
0.6116	Remote Similarity	NPD5983	Phase 2
0.6111	Remote Similarity	NPD4755	Approved
0.6105	Remote Similarity	NPD3702	Approved
0.61	Remote Similarity	NPD5331	Approved
0.61	Remote Similarity	NPD5332	Approved
0.6083	Remote Similarity	NPD7516	Approved
0.6082	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4790	Discontinued
0.6055	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8451	Approved
0.6036	Remote Similarity	NPD5211	Phase 2
0.6034	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD8377	Approved
0.6033	Remote Similarity	NPD8294	Approved
0.6016	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD5285	Approved
0.5984	Remote Similarity	NPD8380	Approved
0.5984	Remote Similarity	NPD8269	Approved
0.5984	Remote Similarity	NPD7503	Approved
0.5984	Remote Similarity	NPD8379	Approved
0.5984	Remote Similarity	NPD8378	Approved
0.5984	Remote Similarity	NPD8268	Approved
0.5984	Remote Similarity	NPD8033	Approved
0.5984	Remote Similarity	NPD8296	Approved
0.5984	Remote Similarity	NPD8267	Approved
0.5984	Remote Similarity	NPD8335	Approved
0.5984	Remote Similarity	NPD8266	Approved
0.598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD3198	Approved
0.5966	Remote Similarity	NPD6274	Approved
0.5954	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6033	Approved
0.5948	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5344	Discontinued
0.5943	Remote Similarity	NPD5693	Phase 1
0.5943	Remote Similarity	NPD5284	Approved
0.5943	Remote Similarity	NPD5281	Approved
0.5941	Remote Similarity	NPD4788	Approved
0.5929	Remote Similarity	NPD5141	Approved
0.592	Remote Similarity	NPD6336	Discontinued
0.5917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4753	Phase 2
0.5893	Remote Similarity	NPD5224	Approved
0.5893	Remote Similarity	NPD4633	Approved
0.5893	Remote Similarity	NPD5225	Approved
0.5893	Remote Similarity	NPD5226	Approved
0.5893	Remote Similarity	NPD7632	Discontinued
0.5887	Remote Similarity	NPD7642	Approved
0.5887	Remote Similarity	NPD8328	Phase 3
0.5882	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7524	Approved
0.5859	Remote Similarity	NPD8390	Approved
0.5859	Remote Similarity	NPD8392	Approved
0.5859	Remote Similarity	NPD8391	Approved
0.5854	Remote Similarity	NPD8444	Approved
0.5841	Remote Similarity	NPD5175	Approved
0.5841	Remote Similarity	NPD5174	Approved
0.584	Remote Similarity	NPD8341	Approved
0.584	Remote Similarity	NPD8340	Approved
0.584	Remote Similarity	NPD8299	Approved
0.584	Remote Similarity	NPD8342	Approved
0.5826	Remote Similarity	NPD6685	Approved
0.582	Remote Similarity	NPD7100	Approved
0.582	Remote Similarity	NPD7101	Approved
0.582	Remote Similarity	NPD4522	Approved
0.5804	Remote Similarity	NPD5223	Approved
0.5794	Remote Similarity	NPD8273	Phase 1
0.5789	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6317	Approved
0.5784	Remote Similarity	NPD6695	Phase 3
0.578	Remote Similarity	NPD4629	Approved
0.578	Remote Similarity	NPD5210	Approved
0.5769	Remote Similarity	NPD7521	Approved
0.5769	Remote Similarity	NPD7334	Approved
0.5769	Remote Similarity	NPD6409	Approved
0.5769	Remote Similarity	NPD6684	Approved
0.5769	Remote Similarity	NPD5330	Approved
0.5769	Remote Similarity	NPD7146	Approved
0.576	Remote Similarity	NPD7829	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