NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	198.13
Volume:	211.354
LogP:	1.257
LogD:	1.143
LogS:	-2.316
# Rotatable Bonds:	2
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	3.922
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.504
MDCK Permeability:	2.1680729332729243e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	63.359920501708984%
Volume Distribution (VD):	0.348
Pgp-substrate:	59.84490966796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.334
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.497
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.282
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	8.411
Half-life (T1/2):	0.562

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.343
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.163
Carcinogencity:	0.064
Eye Corrosion:	0.209
Eye Irritation:	0.75
Respiratory Toxicity:	0.482

Download Data

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

Natural Product: NPC173321

Natural Product ID:	NPC173321
*Common Name:**	(R)-6-Hydroxy-3-(2-Hydroxy-Ethyl)-2,4,4-Trimethyl-Cyclohex-2-Enone
IUPAC Name:	(6R)-6-hydroxy-3-(2-hydroxyethyl)-2,4,4-trimethylcyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	QIOYKXMTBUDZHZ-SECBINFHSA-N
Standard InCHI:	InChI=1S/C11H18O3/c1-7-8(4-5-12)11(2,3)6-9(13)10(7)14/h9,12-13H,4-6H2,1-3H3/t9-/m1/s1
SMILES:	OCCC1=C(C)C(=O)[C@@H](CC1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL87256
PubChem CID:	10397832
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
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11551759]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21214467]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	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	6
Others	1

Activity Type	# Activity
Cell Line	6
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	47.0	ug ml-1	PMID[537418]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	46.0	ug ml-1	PMID[537418]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	52.0	ug ml-1	PMID[537418]
NPT376	Cell Line	A498	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[537418]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[537418]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[537418]
NPT140	Organism	Artemia	Artemia	LC50	=	4.9	ug.mL-1	PMID[537418]

☑ 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 NPC173321 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	173
0.1-0.2	1701
0.2-0.3	8194
0.3-0.4	16740
0.4-0.5	8272
0.5-0.6	5756
0.6-0.7	1630
0.7-0.8	216
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8514	High Similarity	NPC178852
0.8406	Intermediate Similarity	NPC96962
0.8333	Intermediate Similarity	NPC261316
0.8333	Intermediate Similarity	NPC49737
0.8286	Intermediate Similarity	NPC45264
0.8158	Intermediate Similarity	NPC281138
0.8133	Intermediate Similarity	NPC197659
0.8108	Intermediate Similarity	NPC114236
0.8052	Intermediate Similarity	NPC74086
0.8026	Intermediate Similarity	NPC475994
0.8	Intermediate Similarity	NPC36350
0.8	Intermediate Similarity	NPC470525
0.7975	Intermediate Similarity	NPC251475
0.7975	Intermediate Similarity	NPC169941
0.7973	Intermediate Similarity	NPC470299
0.7949	Intermediate Similarity	NPC136150
0.7945	Intermediate Similarity	NPC84790
0.7927	Intermediate Similarity	NPC230387
0.7922	Intermediate Similarity	NPC308038
0.7901	Intermediate Similarity	NPC94666
0.7895	Intermediate Similarity	NPC211279
0.7875	Intermediate Similarity	NPC40687
0.7857	Intermediate Similarity	NPC474329
0.7857	Intermediate Similarity	NPC474304
0.7848	Intermediate Similarity	NPC93590
0.7848	Intermediate Similarity	NPC48362
0.7821	Intermediate Similarity	NPC172013
0.7792	Intermediate Similarity	NPC476808
0.7792	Intermediate Similarity	NPC321180
0.7778	Intermediate Similarity	NPC79573
0.7778	Intermediate Similarity	NPC15807
0.7778	Intermediate Similarity	NPC477452
0.7778	Intermediate Similarity	NPC197823
0.7778	Intermediate Similarity	NPC32037
0.7763	Intermediate Similarity	NPC263582
0.7763	Intermediate Similarity	NPC92080
0.775	Intermediate Similarity	NPC64600
0.7711	Intermediate Similarity	NPC475001
0.7711	Intermediate Similarity	NPC185059
0.7692	Intermediate Similarity	NPC246458
0.7692	Intermediate Similarity	NPC229204
0.7671	Intermediate Similarity	NPC250928
0.7671	Intermediate Similarity	NPC10758
0.7647	Intermediate Similarity	NPC99380
0.7632	Intermediate Similarity	NPC175079
0.7625	Intermediate Similarity	NPC103486
0.76	Intermediate Similarity	NPC247586
0.76	Intermediate Similarity	NPC186042
0.7595	Intermediate Similarity	NPC2482
0.759	Intermediate Similarity	NPC109900
0.759	Intermediate Similarity	NPC272039
0.759	Intermediate Similarity	NPC220930
0.7571	Intermediate Similarity	NPC83200
0.7564	Intermediate Similarity	NPC231739
0.7564	Intermediate Similarity	NPC30321
0.7564	Intermediate Similarity	NPC62336
0.7561	Intermediate Similarity	NPC470574
0.7558	Intermediate Similarity	NPC477436
0.7558	Intermediate Similarity	NPC477435
0.7532	Intermediate Similarity	NPC250621
0.7531	Intermediate Similarity	NPC110150
0.7531	Intermediate Similarity	NPC66764
0.75	Intermediate Similarity	NPC215050
0.75	Intermediate Similarity	NPC471722
0.75	Intermediate Similarity	NPC473420
0.75	Intermediate Similarity	NPC121984
0.75	Intermediate Similarity	NPC470298
0.75	Intermediate Similarity	NPC14151
0.7471	Intermediate Similarity	NPC474328
0.7471	Intermediate Similarity	NPC196485
0.7471	Intermediate Similarity	NPC245972
0.7471	Intermediate Similarity	NPC23170
0.747	Intermediate Similarity	NPC183736
0.747	Intermediate Similarity	NPC472986
0.747	Intermediate Similarity	NPC327115
0.747	Intermediate Similarity	NPC222613
0.747	Intermediate Similarity	NPC474778
0.747	Intermediate Similarity	NPC472974
0.747	Intermediate Similarity	NPC472985
0.747	Intermediate Similarity	NPC145879
0.747	Intermediate Similarity	NPC72133
0.747	Intermediate Similarity	NPC475022
0.747	Intermediate Similarity	NPC31564
0.747	Intermediate Similarity	NPC232156
0.747	Intermediate Similarity	NPC20688
0.747	Intermediate Similarity	NPC474732
0.747	Intermediate Similarity	NPC474733
0.747	Intermediate Similarity	NPC118648
0.747	Intermediate Similarity	NPC202394
0.747	Intermediate Similarity	NPC51014
0.747	Intermediate Similarity	NPC158393
0.7468	Intermediate Similarity	NPC19900
0.7468	Intermediate Similarity	NPC475681
0.7467	Intermediate Similarity	NPC144627
0.7442	Intermediate Similarity	NPC185936
0.7442	Intermediate Similarity	NPC248913
0.7442	Intermediate Similarity	NPC168027
0.7439	Intermediate Similarity	NPC60951
0.7439	Intermediate Similarity	NPC237712
0.7436	Intermediate Similarity	NPC266193
0.7436	Intermediate Similarity	NPC203403
0.7436	Intermediate Similarity	NPC257666
0.7436	Intermediate Similarity	NPC74995
0.7412	Intermediate Similarity	NPC250592
0.7412	Intermediate Similarity	NPC119416
0.7412	Intermediate Similarity	NPC77263
0.7412	Intermediate Similarity	NPC473100
0.7407	Intermediate Similarity	NPC158411
0.7407	Intermediate Similarity	NPC73882
0.7407	Intermediate Similarity	NPC38796
0.7407	Intermediate Similarity	NPC151519
0.7403	Intermediate Similarity	NPC474011
0.7386	Intermediate Similarity	NPC477438
0.7386	Intermediate Similarity	NPC477437
0.7381	Intermediate Similarity	NPC58063
0.7381	Intermediate Similarity	NPC475740
0.7375	Intermediate Similarity	NPC471514
0.7375	Intermediate Similarity	NPC104120
0.7375	Intermediate Similarity	NPC157895
0.7375	Intermediate Similarity	NPC45495
0.7375	Intermediate Similarity	NPC108955
0.7375	Intermediate Similarity	NPC148685
0.7361	Intermediate Similarity	NPC287339
0.7361	Intermediate Similarity	NPC61473
0.7356	Intermediate Similarity	NPC211230
0.7356	Intermediate Similarity	NPC109414
0.7356	Intermediate Similarity	NPC12722
0.7349	Intermediate Similarity	NPC179006
0.7349	Intermediate Similarity	NPC474853
0.7349	Intermediate Similarity	NPC187529
0.7342	Intermediate Similarity	NPC478122
0.7326	Intermediate Similarity	NPC475823
0.7326	Intermediate Similarity	NPC474209
0.7326	Intermediate Similarity	NPC473099
0.7324	Intermediate Similarity	NPC143168
0.7324	Intermediate Similarity	NPC477830
0.7324	Intermediate Similarity	NPC53109
0.7317	Intermediate Similarity	NPC62214
0.7317	Intermediate Similarity	NPC278648
0.7317	Intermediate Similarity	NPC105173
0.7317	Intermediate Similarity	NPC476082
0.7308	Intermediate Similarity	NPC477708
0.7308	Intermediate Similarity	NPC469646
0.7303	Intermediate Similarity	NPC305483
0.7303	Intermediate Similarity	NPC94337
0.7303	Intermediate Similarity	NPC96859
0.7303	Intermediate Similarity	NPC328162
0.7294	Intermediate Similarity	NPC131470
0.7294	Intermediate Similarity	NPC473229
0.7294	Intermediate Similarity	NPC53454
0.7294	Intermediate Similarity	NPC472802
0.7294	Intermediate Similarity	NPC328539
0.7294	Intermediate Similarity	NPC143767
0.7294	Intermediate Similarity	NPC307298
0.7294	Intermediate Similarity	NPC158778
0.7294	Intermediate Similarity	NPC206060
0.7294	Intermediate Similarity	NPC474677
0.7284	Intermediate Similarity	NPC55869
0.7284	Intermediate Similarity	NPC116797
0.7284	Intermediate Similarity	NPC328264
0.7284	Intermediate Similarity	NPC225515
0.7273	Intermediate Similarity	NPC217624
0.7273	Intermediate Similarity	NPC181393
0.7273	Intermediate Similarity	NPC212812
0.7273	Intermediate Similarity	NPC477439
0.7262	Intermediate Similarity	NPC179591
0.7262	Intermediate Similarity	NPC471737
0.7262	Intermediate Similarity	NPC229717
0.7262	Intermediate Similarity	NPC56588
0.725	Intermediate Similarity	NPC472490
0.725	Intermediate Similarity	NPC7232
0.725	Intermediate Similarity	NPC152061
0.725	Intermediate Similarity	NPC192329
0.7241	Intermediate Similarity	NPC73457
0.7241	Intermediate Similarity	NPC111883
0.7241	Intermediate Similarity	NPC116726
0.7241	Intermediate Similarity	NPC155304
0.7229	Intermediate Similarity	NPC321187
0.7229	Intermediate Similarity	NPC470812
0.7229	Intermediate Similarity	NPC85774
0.7229	Intermediate Similarity	NPC221758
0.7229	Intermediate Similarity	NPC472326
0.7229	Intermediate Similarity	NPC329043
0.7229	Intermediate Similarity	NPC58841
0.7229	Intermediate Similarity	NPC161423
0.7229	Intermediate Similarity	NPC214043
0.7229	Intermediate Similarity	NPC227064
0.7229	Intermediate Similarity	NPC59453
0.7229	Intermediate Similarity	NPC473246
0.7229	Intermediate Similarity	NPC180834
0.7222	Intermediate Similarity	NPC7029
0.7222	Intermediate Similarity	NPC43747
0.7222	Intermediate Similarity	NPC471815
0.7222	Intermediate Similarity	NPC471916
0.7215	Intermediate Similarity	NPC325946
0.7215	Intermediate Similarity	NPC471061
0.7215	Intermediate Similarity	NPC86917
0.7215	Intermediate Similarity	NPC82666
0.7215	Intermediate Similarity	NPC276769
0.7209	Intermediate Similarity	NPC76879

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 NPC173321 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	2434
0.2-0.3	3958
0.3-0.4	1838
0.4-0.5	405
0.5-0.6	266
0.6-0.7	58
0.7-0.8	5
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8052	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3704	Approved
0.7561	Intermediate Similarity	NPD1696	Phase 3
0.747	Intermediate Similarity	NPD5279	Phase 3
0.747	Intermediate Similarity	NPD3618	Phase 1
0.7407	Intermediate Similarity	NPD3667	Approved
0.7375	Intermediate Similarity	NPD4695	Discontinued
0.7361	Intermediate Similarity	NPD7341	Phase 2
0.7342	Intermediate Similarity	NPD3617	Approved
0.7324	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7331	Phase 2
0.7229	Intermediate Similarity	NPD4786	Approved
0.7229	Intermediate Similarity	NPD3665	Phase 1
0.7229	Intermediate Similarity	NPD3666	Approved
0.7229	Intermediate Similarity	NPD3133	Approved
0.7209	Intermediate Similarity	NPD5328	Approved
0.7111	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5222	Approved
0.7111	Intermediate Similarity	NPD5221	Approved
0.7111	Intermediate Similarity	NPD4697	Phase 3
0.7045	Intermediate Similarity	NPD7515	Phase 2
0.7045	Intermediate Similarity	NPD6079	Approved
0.7033	Intermediate Similarity	NPD5173	Approved
0.7033	Intermediate Similarity	NPD4755	Approved
0.7011	Intermediate Similarity	NPD4753	Phase 2
0.6966	Remote Similarity	NPD4202	Approved
0.6882	Remote Similarity	NPD4700	Approved
0.6882	Remote Similarity	NPD4696	Approved
0.6882	Remote Similarity	NPD5286	Approved
0.6882	Remote Similarity	NPD5285	Approved
0.6824	Remote Similarity	NPD4197	Approved
0.6812	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5223	Approved
0.6744	Remote Similarity	NPD5329	Approved
0.6737	Remote Similarity	NPD5211	Phase 2
0.6737	Remote Similarity	NPD5226	Approved
0.6737	Remote Similarity	NPD5225	Approved
0.6737	Remote Similarity	NPD4633	Approved
0.6737	Remote Similarity	NPD5224	Approved
0.6703	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.663	Remote Similarity	NPD4629	Approved
0.663	Remote Similarity	NPD5210	Approved
0.6629	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3668	Phase 3
0.6598	Remote Similarity	NPD5141	Approved
0.6588	Remote Similarity	NPD4221	Approved
0.6588	Remote Similarity	NPD4223	Phase 3
0.6579	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6402	Approved
0.6531	Remote Similarity	NPD4768	Approved
0.6531	Remote Similarity	NPD5739	Approved
0.6531	Remote Similarity	NPD7128	Approved
0.6531	Remote Similarity	NPD4767	Approved
0.6531	Remote Similarity	NPD6675	Approved
0.6522	Remote Similarity	NPD5282	Discontinued
0.6489	Remote Similarity	NPD6084	Phase 2
0.6489	Remote Similarity	NPD6083	Phase 2
0.6489	Remote Similarity	NPD7902	Approved
0.6484	Remote Similarity	NPD6411	Approved
0.6477	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5697	Approved
0.6465	Remote Similarity	NPD5701	Approved
0.6452	Remote Similarity	NPD5695	Phase 3
0.6413	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD5168	Approved
0.64	Remote Similarity	NPD4729	Approved
0.64	Remote Similarity	NPD5128	Approved
0.64	Remote Similarity	NPD6011	Approved
0.64	Remote Similarity	NPD4730	Approved
0.64	Remote Similarity	NPD6881	Approved
0.64	Remote Similarity	NPD6899	Approved
0.64	Remote Similarity	NPD7320	Approved
0.6386	Remote Similarity	NPD4756	Discovery
0.6364	Remote Similarity	NPD1694	Approved
0.6341	Remote Similarity	NPD8264	Approved
0.6337	Remote Similarity	NPD6012	Approved
0.6337	Remote Similarity	NPD6014	Approved
0.6337	Remote Similarity	NPD6373	Approved
0.6337	Remote Similarity	NPD6013	Approved
0.6337	Remote Similarity	NPD6372	Approved
0.6333	Remote Similarity	NPD4518	Approved
0.6333	Remote Similarity	NPD5737	Approved
0.6333	Remote Similarity	NPD6672	Approved
0.6329	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3197	Phase 1
0.631	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4623	Approved
0.6292	Remote Similarity	NPD4689	Approved
0.6292	Remote Similarity	NPD4519	Discontinued
0.6292	Remote Similarity	NPD7146	Approved
0.6292	Remote Similarity	NPD6409	Approved
0.6292	Remote Similarity	NPD4688	Approved
0.6292	Remote Similarity	NPD6684	Approved
0.6292	Remote Similarity	NPD5205	Approved
0.6292	Remote Similarity	NPD5330	Approved
0.6292	Remote Similarity	NPD4138	Approved
0.6292	Remote Similarity	NPD7334	Approved
0.6292	Remote Similarity	NPD4690	Approved
0.6292	Remote Similarity	NPD4693	Phase 3
0.6292	Remote Similarity	NPD7521	Approved
0.6279	Remote Similarity	NPD4139	Approved
0.6279	Remote Similarity	NPD4692	Approved
0.6275	Remote Similarity	NPD5169	Approved
0.6275	Remote Similarity	NPD5247	Approved
0.6275	Remote Similarity	NPD5250	Approved
0.6275	Remote Similarity	NPD5251	Approved
0.6275	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5248	Approved
0.6275	Remote Similarity	NPD5249	Phase 3
0.6275	Remote Similarity	NPD7102	Approved
0.6275	Remote Similarity	NPD4634	Approved
0.6275	Remote Similarity	NPD5135	Approved
0.6275	Remote Similarity	NPD7290	Approved
0.6275	Remote Similarity	NPD6883	Approved
0.6265	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5696	Approved
0.6237	Remote Similarity	NPD5133	Approved
0.6214	Remote Similarity	NPD6649	Approved
0.6214	Remote Similarity	NPD6869	Approved
0.6214	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6847	Approved
0.6214	Remote Similarity	NPD6650	Approved
0.6214	Remote Similarity	NPD5215	Approved
0.6214	Remote Similarity	NPD6617	Approved
0.6214	Remote Similarity	NPD8130	Phase 1
0.6214	Remote Similarity	NPD5216	Approved
0.6214	Remote Similarity	NPD5217	Approved
0.6214	Remote Similarity	NPD5127	Approved
0.6197	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5785	Approved
0.618	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5363	Approved
0.6173	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7900	Approved
0.617	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4748	Discontinued
0.6154	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6882	Approved
0.6145	Remote Similarity	NPD8039	Approved
0.6145	Remote Similarity	NPD7339	Approved
0.6145	Remote Similarity	NPD6942	Approved
0.6136	Remote Similarity	NPD4788	Approved
0.6125	Remote Similarity	NPD4137	Phase 3
0.6105	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4632	Approved
0.6092	Remote Similarity	NPD5369	Approved
0.6081	Remote Similarity	NPD287	Approved
0.6064	Remote Similarity	NPD5778	Approved
0.6064	Remote Similarity	NPD5779	Approved
0.6049	Remote Similarity	NPD4747	Approved
0.6049	Remote Similarity	NPD4691	Approved
0.6049	Remote Similarity	NPD4789	Approved
0.6047	Remote Similarity	NPD7645	Phase 2
0.6044	Remote Similarity	NPD3573	Approved
0.6038	Remote Similarity	NPD5167	Approved
0.6026	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD6924	Approved
0.6024	Remote Similarity	NPD6926	Approved
0.6023	Remote Similarity	NPD4269	Approved
0.6023	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4270	Approved
0.6022	Remote Similarity	NPD4096	Approved
0.6022	Remote Similarity	NPD46	Approved
0.6022	Remote Similarity	NPD6698	Approved
0.5981	Remote Similarity	NPD6868	Approved
0.5981	Remote Similarity	NPD6274	Approved
0.5977	Remote Similarity	NPD5368	Approved
0.5976	Remote Similarity	NPD7150	Approved
0.5976	Remote Similarity	NPD5276	Approved
0.5976	Remote Similarity	NPD7151	Approved
0.5976	Remote Similarity	NPD7152	Approved
0.5957	Remote Similarity	NPD5281	Approved
0.5957	Remote Similarity	NPD5284	Approved
0.5955	Remote Similarity	NPD7154	Phase 3
0.5955	Remote Similarity	NPD5362	Discontinued
0.5955	Remote Similarity	NPD6110	Phase 1
0.5952	Remote Similarity	NPD3703	Phase 2
0.5926	Remote Similarity	NPD6009	Approved
0.5926	Remote Similarity	NPD6317	Approved
0.5926	Remote Similarity	NPD6922	Approved
0.5926	Remote Similarity	NPD3698	Phase 2
0.5926	Remote Similarity	NPD6923	Approved
0.5918	Remote Similarity	NPD4225	Approved
0.5918	Remote Similarity	NPD7638	Approved
0.5914	Remote Similarity	NPD6080	Approved
0.5914	Remote Similarity	NPD6673	Approved
0.5914	Remote Similarity	NPD6904	Approved
0.5889	Remote Similarity	NPD6400	Clinical (unspecified phase)

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