NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.12
Volume:	234.803
LogP:	0.659
LogD:	0.022
LogS:	-0.84
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.534
Synthetic Accessibility Score:	4.289
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.482
MDCK Permeability:	0.0001119328589993529
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.856
Plasma Protein Binding (PPB):	25.481950759887695%
Volume Distribution (VD):	0.346
Pgp-substrate:	57.75965881347656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.232
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.609
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	5.363
Half-life (T1/2):	0.648

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.139
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.11
Carcinogencity:	0.654
Eye Corrosion:	0.304
Eye Irritation:	0.889
Respiratory Toxicity:	0.671

Download Data

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

Natural Product: NPC82666

Natural Product ID:	NPC82666
*Common Name:**	(4S,6R)-4,6-Dihydroxy-3-[(E)-3-Hydroxy-3-Methylbut-1-Enyl]-4-Methylcyclohex-2-En-1-One
IUPAC Name:	(4S,6R)-4,6-dihydroxy-3-[(E)-3-hydroxy-3-methylbut-1-enyl]-4-methylcyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	CGPARFHPJHOJGS-PRANIUCASA-N
Standard InCHI:	InChI=1S/C12H18O4/c1-11(2,15)5-4-8-6-9(13)10(14)7-12(8,3)16/h4-6,10,14-16H,7H2,1-3H3/b5-4+/t10-,12+/m1/s1
SMILES:	CC(C)(/C=C/C1=CC(=O)[C@@H](C[C@]1(C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463361
PubChem CID:	11736278
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO32566	periploca aphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869229]
NPO32566	periploca aphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387640]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	150100.0	nM	PMID[544741]

☑ 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 NPC82666 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	159
0.1-0.2	1109
0.2-0.3	6461
0.3-0.4	16094
0.4-0.5	11818
0.5-0.6	5508
0.6-0.7	1387
0.7-0.8	139
0.8-0.85	13
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC97173
0.84	Intermediate Similarity	NPC323437
0.84	Intermediate Similarity	NPC29542
0.84	Intermediate Similarity	NPC201562
0.8293	Intermediate Similarity	NPC187529
0.8289	Intermediate Similarity	NPC122244
0.8133	Intermediate Similarity	NPC107848
0.8101	Intermediate Similarity	NPC231739
0.7973	Intermediate Similarity	NPC269985
0.7949	Intermediate Similarity	NPC166018
0.7949	Intermediate Similarity	NPC225665
0.7949	Intermediate Similarity	NPC169056
0.7922	Intermediate Similarity	NPC153660
0.7901	Intermediate Similarity	NPC74086
0.7875	Intermediate Similarity	NPC478122
0.7831	Intermediate Similarity	NPC477784
0.7831	Intermediate Similarity	NPC477786
0.7831	Intermediate Similarity	NPC477785
0.7765	Intermediate Similarity	NPC196381
0.7763	Intermediate Similarity	NPC136473
0.7733	Intermediate Similarity	NPC106613
0.7692	Intermediate Similarity	NPC186042
0.7683	Intermediate Similarity	NPC160582
0.7561	Intermediate Similarity	NPC19900
0.7556	Intermediate Similarity	NPC217624
0.7556	Intermediate Similarity	NPC78159
0.7556	Intermediate Similarity	NPC181393
0.7534	Intermediate Similarity	NPC269737
0.7528	Intermediate Similarity	NPC142838
0.7528	Intermediate Similarity	NPC32552
0.7473	Intermediate Similarity	NPC476245
0.7439	Intermediate Similarity	NPC248624
0.7416	Intermediate Similarity	NPC477684
0.7381	Intermediate Similarity	NPC275766
0.7381	Intermediate Similarity	NPC67254
0.7381	Intermediate Similarity	NPC470298
0.7375	Intermediate Similarity	NPC215050
0.7342	Intermediate Similarity	NPC95863
0.7317	Intermediate Similarity	NPC471061
0.7294	Intermediate Similarity	NPC38796
0.7294	Intermediate Similarity	NPC158411
0.7292	Intermediate Similarity	NPC104161
0.7292	Intermediate Similarity	NPC469980
0.7292	Intermediate Similarity	NPC118902
0.7241	Intermediate Similarity	NPC15807
0.7241	Intermediate Similarity	NPC32037
0.7229	Intermediate Similarity	NPC475994
0.7222	Intermediate Similarity	NPC134321
0.7222	Intermediate Similarity	NPC131864
0.7215	Intermediate Similarity	NPC173321
0.7209	Intermediate Similarity	NPC251475
0.7209	Intermediate Similarity	NPC169941
0.7195	Intermediate Similarity	NPC7629
0.7195	Intermediate Similarity	NPC151622
0.7191	Intermediate Similarity	NPC229612
0.7191	Intermediate Similarity	NPC7280
0.7179	Intermediate Similarity	NPC45264
0.7179	Intermediate Similarity	NPC117804
0.7174	Intermediate Similarity	NPC474690
0.7172	Intermediate Similarity	NPC264819
0.7159	Intermediate Similarity	NPC94666
0.7159	Intermediate Similarity	NPC472974
0.7143	Intermediate Similarity	NPC472072
0.7143	Intermediate Similarity	NPC116726
0.7143	Intermediate Similarity	NPC281138
0.7143	Intermediate Similarity	NPC475441
0.7128	Intermediate Similarity	NPC474785
0.7128	Intermediate Similarity	NPC474938
0.7126	Intermediate Similarity	NPC40687
0.7126	Intermediate Similarity	NPC31086
0.7126	Intermediate Similarity	NPC295799
0.7113	Intermediate Similarity	NPC247957
0.7113	Intermediate Similarity	NPC249187
0.7111	Intermediate Similarity	NPC474918
0.7111	Intermediate Similarity	NPC473100
0.7108	Intermediate Similarity	NPC473536
0.7097	Intermediate Similarity	NPC180950
0.7097	Intermediate Similarity	NPC272617
0.7093	Intermediate Similarity	NPC279186
0.7089	Intermediate Similarity	NPC236208
0.7083	Intermediate Similarity	NPC224172
0.7079	Intermediate Similarity	NPC472007
0.7079	Intermediate Similarity	NPC23622
0.7071	Intermediate Similarity	NPC266514
0.7059	Intermediate Similarity	NPC470947
0.7059	Intermediate Similarity	NPC172013
0.7059	Intermediate Similarity	NPC470945
0.7059	Intermediate Similarity	NPC470946
0.7037	Intermediate Similarity	NPC12815
0.7037	Intermediate Similarity	NPC215745
0.7037	Intermediate Similarity	NPC238948
0.7033	Intermediate Similarity	NPC473099
0.7033	Intermediate Similarity	NPC19771
0.7033	Intermediate Similarity	NPC128672
0.7011	Intermediate Similarity	NPC16488
0.7	Intermediate Similarity	NPC327106
0.6989	Remote Similarity	NPC196227
0.6989	Remote Similarity	NPC299100
0.6988	Remote Similarity	NPC474197
0.6988	Remote Similarity	NPC477708
0.6979	Remote Similarity	NPC185253
0.6979	Remote Similarity	NPC215253
0.6977	Remote Similarity	NPC474980
0.6974	Remote Similarity	NPC190049
0.697	Remote Similarity	NPC257353
0.6966	Remote Similarity	NPC472009
0.6966	Remote Similarity	NPC203795
0.6966	Remote Similarity	NPC315395
0.6966	Remote Similarity	NPC316426
0.6966	Remote Similarity	NPC183736
0.6962	Remote Similarity	NPC309466
0.6957	Remote Similarity	NPC472978
0.6951	Remote Similarity	NPC227396
0.6947	Remote Similarity	NPC474194
0.6947	Remote Similarity	NPC161147
0.6941	Remote Similarity	NPC308038
0.6941	Remote Similarity	NPC475210
0.6939	Remote Similarity	NPC473624
0.6932	Remote Similarity	NPC302360
0.6923	Remote Similarity	NPC137163
0.6923	Remote Similarity	NPC36668
0.6923	Remote Similarity	NPC118011
0.6914	Remote Similarity	NPC126061
0.6914	Remote Similarity	NPC474884
0.6914	Remote Similarity	NPC67076
0.6914	Remote Similarity	NPC319163
0.6914	Remote Similarity	NPC84790
0.6907	Remote Similarity	NPC112613
0.6907	Remote Similarity	NPC469851
0.6907	Remote Similarity	NPC470184
0.6907	Remote Similarity	NPC207885
0.6905	Remote Similarity	NPC203403
0.6905	Remote Similarity	NPC86917
0.6905	Remote Similarity	NPC34110
0.6905	Remote Similarity	NPC272267
0.6905	Remote Similarity	NPC476007
0.69	Remote Similarity	NPC185
0.6897	Remote Similarity	NPC253364
0.6897	Remote Similarity	NPC93590
0.6889	Remote Similarity	NPC287079
0.6883	Remote Similarity	NPC150162
0.6875	Remote Similarity	NPC166770
0.6875	Remote Similarity	NPC143396
0.6875	Remote Similarity	NPC474060
0.6869	Remote Similarity	NPC72255
0.6867	Remote Similarity	NPC474885
0.686	Remote Similarity	NPC471514
0.6854	Remote Similarity	NPC255174
0.6854	Remote Similarity	NPC79573
0.6848	Remote Similarity	NPC471399
0.6842	Remote Similarity	NPC64985
0.6837	Remote Similarity	NPC87351
0.6837	Remote Similarity	NPC39996
0.6835	Remote Similarity	NPC96962
0.6824	Remote Similarity	NPC321180
0.6818	Remote Similarity	NPC57370
0.6818	Remote Similarity	NPC64600
0.6818	Remote Similarity	NPC66764
0.6818	Remote Similarity	NPC110150
0.6813	Remote Similarity	NPC472008
0.6809	Remote Similarity	NPC472977
0.6809	Remote Similarity	NPC472976
0.6809	Remote Similarity	NPC474882
0.68	Remote Similarity	NPC85529
0.68	Remote Similarity	NPC469852
0.68	Remote Similarity	NPC32006
0.679	Remote Similarity	NPC203819
0.679	Remote Similarity	NPC318766
0.679	Remote Similarity	NPC286154
0.6786	Remote Similarity	NPC16279
0.6786	Remote Similarity	NPC205615
0.6786	Remote Similarity	NPC472305
0.6786	Remote Similarity	NPC263582
0.6786	Remote Similarity	NPC250621
0.6786	Remote Similarity	NPC4492
0.6786	Remote Similarity	NPC51391
0.6786	Remote Similarity	NPC256640
0.6782	Remote Similarity	NPC6663
0.6782	Remote Similarity	NPC101012
0.6782	Remote Similarity	NPC112868
0.6778	Remote Similarity	NPC472985
0.6778	Remote Similarity	NPC472986
0.6778	Remote Similarity	NPC476043
0.6778	Remote Similarity	NPC202394
0.6774	Remote Similarity	NPC172101
0.6771	Remote Similarity	NPC471916
0.6771	Remote Similarity	NPC471694
0.6771	Remote Similarity	NPC134083
0.6771	Remote Similarity	NPC208094
0.6768	Remote Similarity	NPC297281
0.6768	Remote Similarity	NPC311612
0.6768	Remote Similarity	NPC473144
0.6768	Remote Similarity	NPC475050
0.6768	Remote Similarity	NPC111323
0.6765	Remote Similarity	NPC214644
0.6757	Remote Similarity	NPC268185
0.6757	Remote Similarity	NPC71755
0.6747	Remote Similarity	NPC476590
0.6747	Remote Similarity	NPC476649
0.6747	Remote Similarity	NPC114727

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 NPC82666 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1536
0.2-0.3	4122
0.3-0.4	2447
0.4-0.5	632
0.5-0.6	223
0.6-0.7	42
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7901	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1696	Phase 3
0.6905	Remote Similarity	NPD4756	Discovery
0.6818	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD5211	Phase 2
0.6623	Remote Similarity	NPD368	Approved
0.6593	Remote Similarity	NPD5279	Phase 3
0.6538	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5141	Approved
0.6526	Remote Similarity	NPD5778	Approved
0.6526	Remote Similarity	NPD5779	Approved
0.65	Remote Similarity	NPD3704	Approved
0.65	Remote Similarity	NPD7331	Phase 2
0.6494	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5363	Approved
0.6477	Remote Similarity	NPD4252	Approved
0.6471	Remote Similarity	NPD8264	Approved
0.6465	Remote Similarity	NPD5285	Approved
0.6465	Remote Similarity	NPD4696	Approved
0.6465	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD4755	Approved
0.6429	Remote Similarity	NPD4732	Discontinued
0.642	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3618	Phase 1
0.6392	Remote Similarity	NPD5210	Approved
0.6392	Remote Similarity	NPD4629	Approved
0.6383	Remote Similarity	NPD4753	Phase 2
0.6337	Remote Similarity	NPD5224	Approved
0.6337	Remote Similarity	NPD5226	Approved
0.6337	Remote Similarity	NPD4633	Approved
0.6337	Remote Similarity	NPD5225	Approved
0.6333	Remote Similarity	NPD4270	Approved
0.6333	Remote Similarity	NPD4269	Approved
0.6327	Remote Similarity	NPD4697	Phase 3
0.6327	Remote Similarity	NPD5221	Approved
0.6327	Remote Similarity	NPD5222	Approved
0.6327	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4700	Approved
0.6292	Remote Similarity	NPD4695	Discontinued
0.6292	Remote Similarity	NPD4819	Approved
0.6292	Remote Similarity	NPD4822	Approved
0.6292	Remote Similarity	NPD4821	Approved
0.6292	Remote Similarity	NPD4820	Approved
0.6289	Remote Similarity	NPD5282	Discontinued
0.6275	Remote Similarity	NPD5174	Approved
0.6275	Remote Similarity	NPD5175	Approved
0.6264	Remote Similarity	NPD7154	Phase 3
0.6263	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4271	Approved
0.625	Remote Similarity	NPD4268	Approved
0.6238	Remote Similarity	NPD5223	Approved
0.6211	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6101	Approved
0.6203	Remote Similarity	NPD4194	Approved
0.6203	Remote Similarity	NPD4192	Approved
0.6203	Remote Similarity	NPD4193	Approved
0.6203	Remote Similarity	NPD4191	Approved
0.6196	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4219	Approved
0.6154	Remote Similarity	NPD3667	Approved
0.6146	Remote Similarity	NPD5785	Approved
0.6111	Remote Similarity	NPD7514	Phase 3
0.6111	Remote Similarity	NPD7332	Phase 2
0.6111	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5697	Approved
0.6087	Remote Similarity	NPD5362	Discontinued
0.6082	Remote Similarity	NPD7637	Suspended
0.6082	Remote Similarity	NPD6411	Approved
0.6082	Remote Similarity	NPD7983	Approved
0.6082	Remote Similarity	NPD6079	Approved
0.6082	Remote Similarity	NPD7515	Phase 2
0.6067	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4519	Discontinued
0.6064	Remote Similarity	NPD4694	Approved
0.6064	Remote Similarity	NPD4623	Approved
0.6064	Remote Similarity	NPD5786	Approved
0.6064	Remote Similarity	NPD5280	Approved
0.6053	Remote Similarity	NPD342	Phase 1
0.6044	Remote Similarity	NPD5369	Approved
0.6042	Remote Similarity	NPD5328	Approved
0.604	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4225	Approved
0.6038	Remote Similarity	NPD4729	Approved
0.6038	Remote Similarity	NPD6881	Approved
0.6038	Remote Similarity	NPD4730	Approved
0.6038	Remote Similarity	NPD6899	Approved
0.6036	Remote Similarity	NPD7115	Discovery
0.6022	Remote Similarity	NPD3665	Phase 1
0.6022	Remote Similarity	NPD3666	Approved
0.6022	Remote Similarity	NPD3133	Approved
0.6022	Remote Similarity	NPD4786	Approved
0.602	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD6650	Approved
0.6019	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD6402	Approved
0.5981	Remote Similarity	NPD6014	Approved
0.5981	Remote Similarity	NPD6012	Approved
0.5981	Remote Similarity	NPD6372	Approved
0.5981	Remote Similarity	NPD6013	Approved
0.5981	Remote Similarity	NPD6373	Approved
0.5979	Remote Similarity	NPD6698	Approved
0.5979	Remote Similarity	NPD46	Approved
0.5976	Remote Similarity	NPD7341	Phase 2
0.5962	Remote Similarity	NPD4754	Approved
0.5943	Remote Similarity	NPD5701	Approved
0.5941	Remote Similarity	NPD6084	Phase 2
0.5941	Remote Similarity	NPD6083	Phase 2
0.5938	Remote Similarity	NPD4518	Approved
0.5926	Remote Similarity	NPD7290	Approved
0.5926	Remote Similarity	NPD5248	Approved
0.5926	Remote Similarity	NPD5247	Approved
0.5926	Remote Similarity	NPD5249	Phase 3
0.5926	Remote Similarity	NPD4634	Approved
0.5926	Remote Similarity	NPD6883	Approved
0.5926	Remote Similarity	NPD7102	Approved
0.5926	Remote Similarity	NPD5250	Approved
0.5926	Remote Similarity	NPD5251	Approved
0.5918	Remote Similarity	NPD5284	Approved
0.5918	Remote Similarity	NPD5281	Approved
0.5918	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5331	Approved
0.5914	Remote Similarity	NPD5332	Approved
0.5909	Remote Similarity	NPD8039	Approved
0.59	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5695	Phase 3
0.5897	Remote Similarity	NPD8779	Phase 3
0.5895	Remote Similarity	NPD5690	Phase 2
0.5889	Remote Similarity	NPD7145	Approved
0.5888	Remote Similarity	NPD7320	Approved
0.5888	Remote Similarity	NPD6011	Approved
0.5888	Remote Similarity	NPD5128	Approved
0.5882	Remote Similarity	NPD5696	Approved
0.5876	Remote Similarity	NPD5370	Suspended
0.5876	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6847	Approved
0.5872	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5217	Approved
0.5872	Remote Similarity	NPD8130	Phase 1
0.5872	Remote Similarity	NPD5215	Approved
0.5872	Remote Similarity	NPD6869	Approved
0.5872	Remote Similarity	NPD5216	Approved
0.5872	Remote Similarity	NPD6617	Approved
0.587	Remote Similarity	NPD6902	Approved
0.587	Remote Similarity	NPD4790	Discontinued
0.5854	Remote Similarity	NPD3197	Phase 1
0.5851	Remote Similarity	NPD4197	Approved
0.5844	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6648	Approved
0.5818	Remote Similarity	NPD6882	Approved
0.5818	Remote Similarity	NPD8297	Approved
0.5816	Remote Similarity	NPD7838	Discovery
0.5806	Remote Similarity	NPD5209	Approved
0.58	Remote Similarity	NPD7748	Approved
0.5789	Remote Similarity	NPD5329	Approved
0.5789	Remote Similarity	NPD1694	Approved
0.5784	Remote Similarity	NPD7902	Approved
0.578	Remote Similarity	NPD5135	Approved
0.578	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5169	Approved
0.5778	Remote Similarity	NPD5776	Phase 2
0.5778	Remote Similarity	NPD6932	Approved
0.5778	Remote Similarity	NPD6925	Approved
0.5769	Remote Similarity	NPD5344	Discontinued
0.5761	Remote Similarity	NPD6930	Phase 2
0.5761	Remote Similarity	NPD5368	Approved
0.5761	Remote Similarity	NPD6931	Approved
0.5755	Remote Similarity	NPD1237	Approved
0.5747	Remote Similarity	NPD7150	Approved
0.5747	Remote Similarity	NPD7151	Approved
0.5747	Remote Similarity	NPD7152	Approved
0.5745	Remote Similarity	NPD6695	Phase 3
0.5741	Remote Similarity	NPD5168	Approved
0.5729	Remote Similarity	NPD4249	Approved
0.5729	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD5127	Approved
0.5727	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.57	Remote Similarity	NPD6399	Phase 3
0.5699	Remote Similarity	NPD6898	Phase 1
0.5684	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD3668	Phase 3
0.5673	Remote Similarity	NPD7639	Approved
0.5673	Remote Similarity	NPD7640	Approved
0.567	Remote Similarity	NPD4251	Approved
0.567	Remote Similarity	NPD4250	Approved
0.566	Remote Similarity	NPD6647	Phase 2
0.5652	Remote Similarity	NPD6929	Approved
0.5638	Remote Similarity	NPD4221	Approved
0.5638	Remote Similarity	NPD6435	Approved
0.5638	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD4223	Phase 3
0.5632	Remote Similarity	NPD7144	Approved
0.5632	Remote Similarity	NPD7143	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