NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	170.09
Volume:	170.842
LogP:	0.895
LogD:	1.822
LogS:	-1.237
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	4.076
Fsp3:	0.889
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:	-4.631
MDCK Permeability:	0.00012008934572804719
Pgp-inhibitor:	0.001
Pgp-substrate:	0.393
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.837
Plasma Protein Binding (PPB):	44.69877624511719%
Volume Distribution (VD):	0.474
Pgp-substrate:	54.68761444091797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.15
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.142
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.32

ADMET: Excretion

Clearance (CL):	10.76
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.451
Drug-inuced Liver Injury (DILI):	0.372
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.126
Skin Sensitization:	0.444
Carcinogencity:	0.36
Eye Corrosion:	0.864
Eye Irritation:	0.867
Respiratory Toxicity:	0.257

Download Data

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

Natural Product: NPC475062

Natural Product ID:	NPC475062
*Common Name:**	Isoboonein
IUPAC Name:	(4aR,6S,7R,7aR)-6-hydroxy-7-methyl-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one
Synonyms:	Isoboonein
Standard InCHIKey:	DPDXVBIWZBJGSX-NGJRWZKOSA-N
Standard InCHI:	InChI=1S/C9H14O3/c1-5-7-4-12-9(11)3-6(7)2-8(5)10/h5-8,10H,2-4H2,1H3/t5-,6-,7+,8+/m1/s1
SMILES:	O=C1OC[C@@H]2[C@@H](C1)C[C@@H]([C@@H]2C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495275
PubChem CID:	44566204
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
NPO13392	Caiophora coronata	Species	Loasaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695811]
NPO13392	Caiophora coronata	Species	Loasaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[551565]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	128.0	ug.mL-1	PMID[551565]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	128.0	ug.mL-1	PMID[551565]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[551565]

☑ 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 NPC475062 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	294
0.1-0.2	3189
0.2-0.3	11132
0.3-0.4	12949
0.4-0.5	7268
0.5-0.6	6389
0.6-0.7	1410
0.7-0.8	59
0.8-0.85	1
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9104	High Similarity	NPC98711
0.9014	High Similarity	NPC214030
0.9014	High Similarity	NPC83108
0.875	High Similarity	NPC70996
0.8333	Intermediate Similarity	NPC477867
0.8082	Intermediate Similarity	NPC215030
0.8	Intermediate Similarity	NPC470657
0.7901	Intermediate Similarity	NPC31349
0.7639	Intermediate Similarity	NPC319007
0.7625	Intermediate Similarity	NPC157328
0.7619	Intermediate Similarity	NPC77756
0.7619	Intermediate Similarity	NPC246173
0.7531	Intermediate Similarity	NPC291310
0.7407	Intermediate Similarity	NPC111409
0.7326	Intermediate Similarity	NPC52756
0.7326	Intermediate Similarity	NPC474065
0.7308	Intermediate Similarity	NPC474003
0.7294	Intermediate Similarity	NPC200580
0.7284	Intermediate Similarity	NPC212340
0.7273	Intermediate Similarity	NPC179922
0.7273	Intermediate Similarity	NPC155441
0.7262	Intermediate Similarity	NPC239938
0.726	Intermediate Similarity	NPC286842
0.725	Intermediate Similarity	NPC258965
0.725	Intermediate Similarity	NPC156658
0.7241	Intermediate Similarity	NPC476189
0.7229	Intermediate Similarity	NPC473350
0.7215	Intermediate Similarity	NPC470014
0.7183	Intermediate Similarity	NPC235788
0.7176	Intermediate Similarity	NPC470009
0.7176	Intermediate Similarity	NPC203170
0.716	Intermediate Similarity	NPC126248
0.7159	Intermediate Similarity	NPC470423
0.7159	Intermediate Similarity	NPC470424
0.7143	Intermediate Similarity	NPC472272
0.7111	Intermediate Similarity	NPC471241
0.7089	Intermediate Similarity	NPC474404
0.7067	Intermediate Similarity	NPC28526
0.7051	Intermediate Similarity	NPC68565
0.7051	Intermediate Similarity	NPC35871
0.7045	Intermediate Similarity	NPC161035
0.7037	Intermediate Similarity	NPC477851
0.7033	Intermediate Similarity	NPC253995
0.6988	Remote Similarity	NPC15091
0.6988	Remote Similarity	NPC128246
0.6986	Remote Similarity	NPC157518
0.6962	Remote Similarity	NPC474020
0.6951	Remote Similarity	NPC191711
0.6914	Remote Similarity	NPC472310
0.6914	Remote Similarity	NPC201276
0.6914	Remote Similarity	NPC80891
0.6905	Remote Similarity	NPC473336
0.6905	Remote Similarity	NPC471044
0.6897	Remote Similarity	NPC215556
0.6889	Remote Similarity	NPC215570
0.6889	Remote Similarity	NPC305808
0.6889	Remote Similarity	NPC37408
0.6883	Remote Similarity	NPC96322
0.6882	Remote Similarity	NPC3488
0.6882	Remote Similarity	NPC259654
0.6882	Remote Similarity	NPC287539
0.6882	Remote Similarity	NPC298266
0.6875	Remote Similarity	NPC169389
0.6867	Remote Similarity	NPC242771
0.6867	Remote Similarity	NPC311642
0.6867	Remote Similarity	NPC100366
0.6867	Remote Similarity	NPC164289
0.6835	Remote Similarity	NPC132064
0.6835	Remote Similarity	NPC471491
0.6829	Remote Similarity	NPC51507
0.6824	Remote Similarity	NPC204105
0.6824	Remote Similarity	NPC284534
0.6824	Remote Similarity	NPC300082
0.6824	Remote Similarity	NPC476715
0.6818	Remote Similarity	NPC216284
0.6813	Remote Similarity	NPC193785
0.6809	Remote Similarity	NPC177013
0.6809	Remote Similarity	NPC35185
0.6809	Remote Similarity	NPC470172
0.6809	Remote Similarity	NPC474730
0.6809	Remote Similarity	NPC4899
0.6806	Remote Similarity	NPC469923
0.6795	Remote Similarity	NPC51249
0.6795	Remote Similarity	NPC470660
0.6795	Remote Similarity	NPC473699
0.6795	Remote Similarity	NPC475232
0.6795	Remote Similarity	NPC474100
0.6795	Remote Similarity	NPC473775
0.6795	Remote Similarity	NPC470659
0.6795	Remote Similarity	NPC475260
0.679	Remote Similarity	NPC185465
0.679	Remote Similarity	NPC171426
0.679	Remote Similarity	NPC80089
0.679	Remote Similarity	NPC34046
0.679	Remote Similarity	NPC199965
0.679	Remote Similarity	NPC471045
0.679	Remote Similarity	NPC224802
0.679	Remote Similarity	NPC475616
0.679	Remote Similarity	NPC324700
0.679	Remote Similarity	NPC476732
0.6786	Remote Similarity	NPC472847
0.6786	Remote Similarity	NPC474266
0.6786	Remote Similarity	NPC259173
0.6782	Remote Similarity	NPC191221
0.6782	Remote Similarity	NPC178875
0.6782	Remote Similarity	NPC79549
0.6765	Remote Similarity	NPC319589
0.6761	Remote Similarity	NPC469924
0.6761	Remote Similarity	NPC475821
0.6753	Remote Similarity	NPC477929
0.6747	Remote Similarity	NPC254123
0.6747	Remote Similarity	NPC475743
0.6744	Remote Similarity	NPC56593
0.6739	Remote Similarity	NPC261372
0.6739	Remote Similarity	NPC263674
0.6739	Remote Similarity	NPC472273
0.6739	Remote Similarity	NPC58267
0.6737	Remote Similarity	NPC473406
0.6737	Remote Similarity	NPC37240
0.6737	Remote Similarity	NPC471253
0.6714	Remote Similarity	NPC119425
0.6712	Remote Similarity	NPC474552
0.6711	Remote Similarity	NPC82315
0.6709	Remote Similarity	NPC167702
0.6709	Remote Similarity	NPC280026
0.6707	Remote Similarity	NPC320144
0.6707	Remote Similarity	NPC476176
0.6706	Remote Similarity	NPC194859
0.6706	Remote Similarity	NPC477434
0.6706	Remote Similarity	NPC224386
0.6705	Remote Similarity	NPC155935
0.6703	Remote Similarity	NPC62407
0.6703	Remote Similarity	NPC163228
0.6703	Remote Similarity	NPC470191
0.6703	Remote Similarity	NPC287354
0.6702	Remote Similarity	NPC39683
0.6667	Remote Similarity	NPC477935
0.6667	Remote Similarity	NPC289486
0.6667	Remote Similarity	NPC61107
0.6667	Remote Similarity	NPC121121
0.6667	Remote Similarity	NPC314364
0.6667	Remote Similarity	NPC311102
0.6667	Remote Similarity	NPC66145
0.6667	Remote Similarity	NPC88469
0.6667	Remote Similarity	NPC200237
0.6667	Remote Similarity	NPC469940
0.6667	Remote Similarity	NPC473899
0.6667	Remote Similarity	NPC180199
0.6667	Remote Similarity	NPC477919
0.6667	Remote Similarity	NPC24556
0.6667	Remote Similarity	NPC211087
0.6667	Remote Similarity	NPC143250
0.6667	Remote Similarity	NPC207010
0.6667	Remote Similarity	NPC148740
0.6667	Remote Similarity	NPC270270
0.6667	Remote Similarity	NPC118601
0.6667	Remote Similarity	NPC317913
0.6667	Remote Similarity	NPC472237
0.6667	Remote Similarity	NPC475849
0.6667	Remote Similarity	NPC472238
0.6667	Remote Similarity	NPC470243
0.6667	Remote Similarity	NPC102156
0.6632	Remote Similarity	NPC244969
0.6632	Remote Similarity	NPC213528
0.663	Remote Similarity	NPC116683
0.663	Remote Similarity	NPC91771
0.663	Remote Similarity	NPC476728
0.663	Remote Similarity	NPC142529
0.663	Remote Similarity	NPC126156
0.663	Remote Similarity	NPC42042
0.6629	Remote Similarity	NPC54065
0.6629	Remote Similarity	NPC35809
0.6629	Remote Similarity	NPC297474
0.6628	Remote Similarity	NPC477205
0.6627	Remote Similarity	NPC125366
0.6627	Remote Similarity	NPC472853
0.6627	Remote Similarity	NPC1882
0.6627	Remote Similarity	NPC474714
0.6625	Remote Similarity	NPC472311
0.6625	Remote Similarity	NPC159789
0.6625	Remote Similarity	NPC217725
0.6625	Remote Similarity	NPC212733
0.6623	Remote Similarity	NPC252032
0.6623	Remote Similarity	NPC469941
0.6623	Remote Similarity	NPC319671
0.6623	Remote Similarity	NPC324607
0.6623	Remote Similarity	NPC321732
0.6623	Remote Similarity	NPC476734
0.6622	Remote Similarity	NPC314103
0.6598	Remote Similarity	NPC170432
0.6598	Remote Similarity	NPC127235
0.6596	Remote Similarity	NPC471381
0.6596	Remote Similarity	NPC218383
0.6593	Remote Similarity	NPC90453
0.6591	Remote Similarity	NPC226491
0.6591	Remote Similarity	NPC217983
0.6591	Remote Similarity	NPC207114
0.6591	Remote Similarity	NPC236459
0.6591	Remote Similarity	NPC477614
0.6588	Remote Similarity	NPC29342

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 NPC475062 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	3566
0.2-0.3	3444
0.3-0.4	969
0.4-0.5	410
0.5-0.6	318
0.6-0.7	44
0.7-0.8	4
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
0.7761	Intermediate Similarity	NPD3198	Approved
0.75	Intermediate Similarity	NPD3702	Approved
0.7436	Intermediate Similarity	NPD4238	Approved
0.7436	Intermediate Similarity	NPD4802	Phase 2
0.6867	Remote Similarity	NPD6435	Approved
0.679	Remote Similarity	NPD6697	Approved
0.679	Remote Similarity	NPD6114	Approved
0.679	Remote Similarity	NPD6118	Approved
0.679	Remote Similarity	NPD6115	Approved
0.6709	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6627	Remote Similarity	NPD5368	Approved
0.6625	Remote Similarity	NPD3703	Phase 2
0.6623	Remote Similarity	NPD3698	Phase 2
0.6622	Remote Similarity	NPD7909	Approved
0.6543	Remote Similarity	NPD6117	Approved
0.6538	Remote Similarity	NPD4245	Approved
0.6538	Remote Similarity	NPD4244	Approved
0.6533	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD1700	Approved
0.6327	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD634	Phase 3
0.6286	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD615	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6928	Phase 2
0.6234	Remote Similarity	NPD4224	Phase 2
0.6207	Remote Similarity	NPD5362	Discontinued
0.6203	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5786	Approved
0.618	Remote Similarity	NPD4249	Approved
0.6163	Remote Similarity	NPD5369	Approved
0.6125	Remote Similarity	NPD4789	Approved
0.6111	Remote Similarity	NPD4251	Approved
0.6111	Remote Similarity	NPD4250	Approved
0.6058	Remote Similarity	NPD6053	Discontinued
0.6049	Remote Similarity	NPD6081	Approved
0.6047	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD1780	Approved
0.5977	Remote Similarity	NPD1779	Approved
0.5941	Remote Similarity	NPD6402	Approved
0.5941	Remote Similarity	NPD6675	Approved
0.5941	Remote Similarity	NPD5739	Approved
0.5941	Remote Similarity	NPD7128	Approved
0.5909	Remote Similarity	NPD4270	Approved
0.5909	Remote Similarity	NPD4269	Approved
0.5909	Remote Similarity	NPD7345	Approved
0.5897	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5701	Approved
0.5882	Remote Similarity	NPD5697	Approved
0.5875	Remote Similarity	NPD229	Approved
0.5862	Remote Similarity	NPD4820	Approved
0.5862	Remote Similarity	NPD4821	Approved
0.5862	Remote Similarity	NPD4819	Approved
0.5862	Remote Similarity	NPD4822	Approved
0.5851	Remote Similarity	NPD8034	Phase 2
0.5851	Remote Similarity	NPD8035	Phase 2
0.5849	Remote Similarity	NPD4632	Approved
0.5833	Remote Similarity	NPD3730	Approved
0.5833	Remote Similarity	NPD3728	Approved
0.5825	Remote Similarity	NPD6011	Approved
0.5825	Remote Similarity	NPD6899	Approved
0.5825	Remote Similarity	NPD7320	Approved
0.5825	Remote Similarity	NPD6881	Approved
0.5823	Remote Similarity	NPD375	Phase 2
0.5814	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD4271	Approved
0.5814	Remote Similarity	NPD4268	Approved
0.5811	Remote Similarity	NPD8959	Approved
0.5806	Remote Similarity	NPD6101	Approved
0.5806	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD1695	Approved
0.5789	Remote Similarity	NPD5779	Approved
0.5789	Remote Similarity	NPD6399	Phase 3
0.5789	Remote Similarity	NPD5778	Approved
0.5784	Remote Similarity	NPD6008	Approved
0.5775	Remote Similarity	NPD3186	Phase 1
0.5769	Remote Similarity	NPD6012	Approved
0.5769	Remote Similarity	NPD6373	Approved
0.5769	Remote Similarity	NPD371	Approved
0.5769	Remote Similarity	NPD6014	Approved
0.5769	Remote Similarity	NPD6013	Approved
0.5769	Remote Similarity	NPD6372	Approved
0.5745	Remote Similarity	NPD46	Approved
0.5745	Remote Similarity	NPD6698	Approved
0.5728	Remote Similarity	NPD6412	Phase 2
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD7290	Approved
0.5714	Remote Similarity	NPD5363	Approved
0.5714	Remote Similarity	NPD6084	Phase 2
0.5714	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD6883	Approved
0.5688	Remote Similarity	NPD6009	Approved
0.5684	Remote Similarity	NPD7983	Approved
0.5684	Remote Similarity	NPD6411	Approved
0.5682	Remote Similarity	NPD4252	Approved
0.5679	Remote Similarity	NPD5360	Phase 3
0.5679	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD73	Approved
0.5676	Remote Similarity	NPD6319	Approved
0.5672	Remote Similarity	NPD2699	Approved
0.567	Remote Similarity	NPD5695	Phase 3
0.5667	Remote Similarity	NPD5331	Approved
0.5667	Remote Similarity	NPD4788	Approved
0.5667	Remote Similarity	NPD7154	Phase 3
0.5667	Remote Similarity	NPD5332	Approved
0.5667	Remote Similarity	NPD3669	Approved
0.5667	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6650	Approved
0.566	Remote Similarity	NPD6869	Approved
0.566	Remote Similarity	NPD6649	Approved
0.566	Remote Similarity	NPD6617	Approved
0.566	Remote Similarity	NPD6847	Approved
0.566	Remote Similarity	NPD8130	Phase 1
0.5657	Remote Similarity	NPD7638	Approved
0.5652	Remote Similarity	NPD6409	Approved
0.5652	Remote Similarity	NPD7146	Approved
0.5652	Remote Similarity	NPD6684	Approved
0.5652	Remote Similarity	NPD2266	Phase 2
0.5652	Remote Similarity	NPD5330	Approved
0.5652	Remote Similarity	NPD7521	Approved
0.5652	Remote Similarity	NPD7334	Approved
0.5644	Remote Similarity	NPD8139	Approved
0.5644	Remote Similarity	NPD8083	Approved
0.5644	Remote Similarity	NPD8086	Approved
0.5644	Remote Similarity	NPD8082	Approved
0.5644	Remote Similarity	NPD8085	Approved
0.5644	Remote Similarity	NPD8084	Approved
0.5644	Remote Similarity	NPD8138	Approved
0.5632	Remote Similarity	NPD3671	Phase 1
0.5625	Remote Similarity	NPD5983	Phase 2
0.5618	Remote Similarity	NPD4790	Discontinued
0.5607	Remote Similarity	NPD8297	Approved
0.5607	Remote Similarity	NPD6882	Approved
0.5604	Remote Similarity	NPD3133	Approved
0.5604	Remote Similarity	NPD3666	Approved
0.5604	Remote Similarity	NPD3665	Phase 1
0.56	Remote Similarity	NPD7640	Approved
0.56	Remote Similarity	NPD7639	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