NPASS Compound

Structure

NPC108955 OpenBabel07101718192D 24 26 0 0 1 0 0 0 0 0999 V2000 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 16 1 0 0 0 0 11 17 2 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 1 0 0 0 15 19 1 0 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 1 0 0 0 18 21 1 0 0 0 0 19 24 2 0 0 0 0 20 3 1 1 0 0 0 21 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.2
Volume:	359.291
LogP:	3.846
LogD:	3.31
LogS:	-4.384
# Rotatable Bonds:	2
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	4.391
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.68
MDCK Permeability:	2.7598927772487514e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	96.48685455322266%
Volume Distribution (VD):	1.739
Pgp-substrate:	4.635190486907959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.655
CYP1A2-substrate:	0.59
CYP2C19-inhibitor:	0.707
CYP2C19-substrate:	0.664
CYP2C9-inhibitor:	0.566
CYP2C9-substrate:	0.18
CYP2D6-inhibitor:	0.877
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.79
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	2.527
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.829
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.805
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.95
Carcinogencity:	0.851
Eye Corrosion:	0.357
Eye Irritation:	0.379
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC108955

Natural Product ID:	NPC108955
*Common Name:**	3'-Hydroxyavarone
IUPAC Name:	2-[[(1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]-6-hydroxycyclohexa-2,5-diene-1,4-dione
Synonyms:	3'-Hydroxyavarone
Standard InCHIKey:	RQEBMLJSOUMSIH-FEHMIHBQSA-N
Standard InCHI:	InChI=1S/C21H28O3/c1-13-6-5-7-18-20(13,3)9-8-14(2)21(18,4)12-15-10-16(22)11-17(23)19(15)24/h6,10-11,14,18,23H,5,7-9,12H2,1-4H3/t14-,18+,20+,21+/m0/s1
SMILES:	O=C1C=C(O)C(=O)C(=C1)C[C@]1(C)[C@@H](C)CC[C@]2([C@H]1CCC=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517338
PubChem CID:	452329
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO33143	Dysidea cinerea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1710654]
NPO33143	Dysidea cinerea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[31532203]

☑ 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
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.6	ug.mL-1	PMID[515514]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	12.5	ug.mL-1	PMID[515514]

☑ 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 NPC108955 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	175
0.1-0.2	1236
0.2-0.3	5515
0.3-0.4	14817
0.4-0.5	10207
0.5-0.6	6484
0.6-0.7	3206
0.7-0.8	941
0.8-0.85	79
0.85-0.9	23
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC55869
0.9459	High Similarity	NPC92080
0.9367	High Similarity	NPC263997
0.9367	High Similarity	NPC8518
0.9367	High Similarity	NPC132228
0.9351	High Similarity	NPC225515
0.9342	High Similarity	NPC27817
0.9231	High Similarity	NPC103486
0.9211	High Similarity	NPC30321
0.9211	High Similarity	NPC189485
0.92	High Similarity	NPC1254
0.9125	High Similarity	NPC241512
0.9125	High Similarity	NPC6185
0.9114	High Similarity	NPC53733
0.9114	High Similarity	NPC105803
0.9103	High Similarity	NPC474085
0.8947	High Similarity	NPC110725
0.8889	High Similarity	NPC33663
0.8889	High Similarity	NPC474680
0.8734	High Similarity	NPC2482
0.8734	High Similarity	NPC476809
0.8718	High Similarity	NPC74410
0.8718	High Similarity	NPC476808
0.8701	High Similarity	NPC470525
0.8659	High Similarity	NPC133652
0.8659	High Similarity	NPC469993
0.8625	High Similarity	NPC278459
0.8625	High Similarity	NPC99308
0.8625	High Similarity	NPC121984
0.8625	High Similarity	NPC116797
0.8608	High Similarity	NPC192329
0.859	High Similarity	NPC165711
0.8571	High Similarity	NPC175079
0.8554	High Similarity	NPC94666
0.8537	High Similarity	NPC237712
0.8537	High Similarity	NPC144258
0.8506	High Similarity	NPC23170
0.85	High Similarity	NPC18955
0.8481	Intermediate Similarity	NPC471409
0.8481	Intermediate Similarity	NPC275494
0.8471	Intermediate Similarity	NPC65615
0.8471	Intermediate Similarity	NPC68148
0.8471	Intermediate Similarity	NPC112454
0.8462	Intermediate Similarity	NPC180886
0.8434	Intermediate Similarity	NPC474537
0.8434	Intermediate Similarity	NPC32037
0.8415	Intermediate Similarity	NPC49019
0.8409	Intermediate Similarity	NPC147232
0.8395	Intermediate Similarity	NPC44963
0.8395	Intermediate Similarity	NPC472684
0.8395	Intermediate Similarity	NPC473217
0.8395	Intermediate Similarity	NPC471898
0.8391	Intermediate Similarity	NPC263780
0.8375	Intermediate Similarity	NPC472490
0.8372	Intermediate Similarity	NPC475823
0.8372	Intermediate Similarity	NPC474209
0.8354	Intermediate Similarity	NPC266193
0.8354	Intermediate Similarity	NPC257666
0.8354	Intermediate Similarity	NPC97377
0.8353	Intermediate Similarity	NPC58271
0.8333	Intermediate Similarity	NPC472974
0.8333	Intermediate Similarity	NPC327115
0.8313	Intermediate Similarity	NPC473246
0.8293	Intermediate Similarity	NPC238991
0.8293	Intermediate Similarity	NPC260956
0.8293	Intermediate Similarity	NPC302661
0.8293	Intermediate Similarity	NPC193347
0.8276	Intermediate Similarity	NPC174167
0.8276	Intermediate Similarity	NPC470036
0.8276	Intermediate Similarity	NPC99380
0.8272	Intermediate Similarity	NPC26139
0.8272	Intermediate Similarity	NPC469637
0.8272	Intermediate Similarity	NPC287063
0.8272	Intermediate Similarity	NPC472478
0.8267	Intermediate Similarity	NPC188292
0.8267	Intermediate Similarity	NPC260474
0.8256	Intermediate Similarity	NPC474918
0.825	Intermediate Similarity	NPC62336
0.825	Intermediate Similarity	NPC207772
0.8235	Intermediate Similarity	NPC470523
0.8235	Intermediate Similarity	NPC220930
0.8235	Intermediate Similarity	NPC272039
0.8228	Intermediate Similarity	NPC26504
0.8228	Intermediate Similarity	NPC309399
0.8228	Intermediate Similarity	NPC76966
0.8228	Intermediate Similarity	NPC186554
0.8228	Intermediate Similarity	NPC69143
0.8228	Intermediate Similarity	NPC263582
0.8214	Intermediate Similarity	NPC29447
0.8214	Intermediate Similarity	NPC469948
0.8193	Intermediate Similarity	NPC470015
0.8193	Intermediate Similarity	NPC168188
0.8193	Intermediate Similarity	NPC102197
0.8182	Intermediate Similarity	NPC211230
0.8171	Intermediate Similarity	NPC38350
0.8171	Intermediate Similarity	NPC477372
0.8171	Intermediate Similarity	NPC470034
0.8171	Intermediate Similarity	NPC475863
0.8171	Intermediate Similarity	NPC189237
0.8171	Intermediate Similarity	NPC201912
0.8161	Intermediate Similarity	NPC129913
0.8158	Intermediate Similarity	NPC474060
0.8148	Intermediate Similarity	NPC170394
0.8148	Intermediate Similarity	NPC476177
0.814	Intermediate Similarity	NPC471722
0.814	Intermediate Similarity	NPC307298
0.814	Intermediate Similarity	NPC470524
0.814	Intermediate Similarity	NPC72397
0.8125	Intermediate Similarity	NPC197659
0.8125	Intermediate Similarity	NPC472300
0.8125	Intermediate Similarity	NPC476811
0.8118	Intermediate Similarity	NPC474733
0.8118	Intermediate Similarity	NPC222613
0.8118	Intermediate Similarity	NPC145879
0.8118	Intermediate Similarity	NPC20688
0.8118	Intermediate Similarity	NPC118648
0.8118	Intermediate Similarity	NPC474732
0.8118	Intermediate Similarity	NPC475022
0.8118	Intermediate Similarity	NPC31564
0.8118	Intermediate Similarity	NPC51014
0.8118	Intermediate Similarity	NPC474778
0.8101	Intermediate Similarity	NPC192540
0.8101	Intermediate Similarity	NPC476795
0.8101	Intermediate Similarity	NPC279666
0.8095	Intermediate Similarity	NPC85774
0.8095	Intermediate Similarity	NPC161423
0.8095	Intermediate Similarity	NPC227064
0.8095	Intermediate Similarity	NPC96095
0.8095	Intermediate Similarity	NPC58841
0.8095	Intermediate Similarity	NPC476412
0.8095	Intermediate Similarity	NPC321187
0.8095	Intermediate Similarity	NPC329043
0.8095	Intermediate Similarity	NPC214043
0.8095	Intermediate Similarity	NPC53385
0.809	Intermediate Similarity	NPC474882
0.809	Intermediate Similarity	NPC474328
0.8072	Intermediate Similarity	NPC151519
0.8072	Intermediate Similarity	NPC320514
0.8072	Intermediate Similarity	NPC48362
0.8072	Intermediate Similarity	NPC69101
0.8072	Intermediate Similarity	NPC251779
0.8072	Intermediate Similarity	NPC310989
0.8068	Intermediate Similarity	NPC26865
0.8046	Intermediate Similarity	NPC477973
0.8046	Intermediate Similarity	NPC326627
0.8046	Intermediate Similarity	NPC310010
0.8046	Intermediate Similarity	NPC119416
0.8026	Intermediate Similarity	NPC310992
0.8026	Intermediate Similarity	NPC87141
0.8025	Intermediate Similarity	NPC475994
0.8023	Intermediate Similarity	NPC475740
0.8023	Intermediate Similarity	NPC136548
0.8023	Intermediate Similarity	NPC58063
0.8023	Intermediate Similarity	NPC93778
0.8	Intermediate Similarity	NPC476426
0.8	Intermediate Similarity	NPC33881
0.8	Intermediate Similarity	NPC777
0.8	Intermediate Similarity	NPC255174
0.8	Intermediate Similarity	NPC311702
0.8	Intermediate Similarity	NPC472305
0.8	Intermediate Similarity	NPC94531
0.8	Intermediate Similarity	NPC123319
0.7978	Intermediate Similarity	NPC134826
0.7978	Intermediate Similarity	NPC250575
0.7976	Intermediate Similarity	NPC291999
0.7976	Intermediate Similarity	NPC83569
0.7976	Intermediate Similarity	NPC307258
0.7976	Intermediate Similarity	NPC309309
0.7976	Intermediate Similarity	NPC69279
0.7975	Intermediate Similarity	NPC283908
0.7975	Intermediate Similarity	NPC251970
0.7975	Intermediate Similarity	NPC103958
0.7975	Intermediate Similarity	NPC476046
0.7975	Intermediate Similarity	NPC241854
0.7975	Intermediate Similarity	NPC147438
0.7975	Intermediate Similarity	NPC183503
0.7975	Intermediate Similarity	NPC161923
0.7975	Intermediate Similarity	NPC301065
0.7955	Intermediate Similarity	NPC191684
0.7955	Intermediate Similarity	NPC223093
0.7955	Intermediate Similarity	NPC38952
0.7955	Intermediate Similarity	NPC113393
0.7952	Intermediate Similarity	NPC149237
0.7952	Intermediate Similarity	NPC267691
0.7952	Intermediate Similarity	NPC475833
0.7952	Intermediate Similarity	NPC162632
0.7952	Intermediate Similarity	NPC3915
0.7952	Intermediate Similarity	NPC226068
0.7952	Intermediate Similarity	NPC274050
0.7952	Intermediate Similarity	NPC263272
0.7952	Intermediate Similarity	NPC90055
0.7952	Intermediate Similarity	NPC14151
0.7952	Intermediate Similarity	NPC6663
0.7952	Intermediate Similarity	NPC147066
0.7949	Intermediate Similarity	NPC84790
0.7949	Intermediate Similarity	NPC160817
0.7935	Intermediate Similarity	NPC147954
0.7931	Intermediate Similarity	NPC206060
0.7931	Intermediate Similarity	NPC48107
0.7931	Intermediate Similarity	NPC53454

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 NPC108955 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1656
0.2-0.3	3970
0.3-0.4	2329
0.4-0.5	602
0.5-0.6	211
0.6-0.7	117
0.7-0.8	79
0.8-0.85	8
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9474	High Similarity	NPD4695	Discontinued
0.878	High Similarity	NPD5690	Phase 2
0.8718	High Similarity	NPD3617	Approved
0.8554	High Similarity	NPD5280	Approved
0.8554	High Similarity	NPD4694	Approved
0.8537	High Similarity	NPD4197	Approved
0.8471	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD5329	Approved
0.8333	Intermediate Similarity	NPD5279	Phase 3
0.8293	Intermediate Similarity	NPD4223	Phase 3
0.8293	Intermediate Similarity	NPD4221	Approved
0.8095	Intermediate Similarity	NPD3133	Approved
0.8095	Intermediate Similarity	NPD3665	Phase 1
0.8095	Intermediate Similarity	NPD3666	Approved
0.8072	Intermediate Similarity	NPD3667	Approved
0.8046	Intermediate Similarity	NPD4753	Phase 2
0.7907	Intermediate Similarity	NPD4138	Approved
0.7907	Intermediate Similarity	NPD5205	Approved
0.7907	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4519	Discontinued
0.7907	Intermediate Similarity	NPD4689	Approved
0.7907	Intermediate Similarity	NPD4623	Approved
0.7907	Intermediate Similarity	NPD3618	Phase 1
0.7907	Intermediate Similarity	NPD4688	Approved
0.7907	Intermediate Similarity	NPD4690	Approved
0.7907	Intermediate Similarity	NPD4693	Phase 3
0.7882	Intermediate Similarity	NPD4786	Approved
0.7821	Intermediate Similarity	NPD4691	Approved
0.7802	Intermediate Similarity	NPD5210	Approved
0.7802	Intermediate Similarity	NPD4629	Approved
0.7802	Intermediate Similarity	NPD5695	Phase 3
0.7778	Intermediate Similarity	NPD5133	Approved
0.7717	Intermediate Similarity	NPD5222	Approved
0.7717	Intermediate Similarity	NPD5221	Approved
0.7717	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4195	Approved
0.7692	Intermediate Similarity	NPD4137	Phase 3
0.7667	Intermediate Similarity	NPD5284	Approved
0.7667	Intermediate Similarity	NPD6079	Approved
0.7667	Intermediate Similarity	NPD5281	Approved
0.764	Intermediate Similarity	NPD5328	Approved
0.7634	Intermediate Similarity	NPD5173	Approved
0.76	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4747	Approved
0.7556	Intermediate Similarity	NPD4096	Approved
0.7556	Intermediate Similarity	NPD5692	Phase 3
0.7531	Intermediate Similarity	NPD4058	Approved
0.7531	Intermediate Similarity	NPD5733	Approved
0.7531	Intermediate Similarity	NPD4687	Approved
0.7529	Intermediate Similarity	NPD4692	Approved
0.7529	Intermediate Similarity	NPD4139	Approved
0.7528	Intermediate Similarity	NPD6672	Approved
0.7528	Intermediate Similarity	NPD5737	Approved
0.7528	Intermediate Similarity	NPD4518	Approved
0.7527	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD5276	Approved
0.7474	Intermediate Similarity	NPD5285	Approved
0.7474	Intermediate Similarity	NPD5286	Approved
0.7474	Intermediate Similarity	NPD4696	Approved
0.7473	Intermediate Similarity	NPD7515	Phase 2
0.7473	Intermediate Similarity	NPD5694	Approved
0.7473	Intermediate Similarity	NPD6050	Approved
0.7471	Intermediate Similarity	NPD3668	Phase 3
0.7447	Intermediate Similarity	NPD6084	Phase 2
0.7447	Intermediate Similarity	NPD6083	Phase 2
0.7447	Intermediate Similarity	NPD4755	Approved
0.7444	Intermediate Similarity	NPD6673	Approved
0.7444	Intermediate Similarity	NPD6080	Approved
0.7444	Intermediate Similarity	NPD6904	Approved
0.7416	Intermediate Similarity	NPD3573	Approved
0.7396	Intermediate Similarity	NPD5223	Approved
0.7391	Intermediate Similarity	NPD4202	Approved
0.7368	Intermediate Similarity	NPD5696	Approved
0.7356	Intermediate Similarity	NPD4788	Approved
0.734	Intermediate Similarity	NPD7614	Phase 1
0.732	Intermediate Similarity	NPD5224	Approved
0.732	Intermediate Similarity	NPD5225	Approved
0.732	Intermediate Similarity	NPD5226	Approved
0.732	Intermediate Similarity	NPD4633	Approved
0.732	Intermediate Similarity	NPD5091	Approved
0.732	Intermediate Similarity	NPD5211	Phase 2
0.7312	Intermediate Similarity	NPD7748	Approved
0.7308	Intermediate Similarity	NPD7331	Phase 2
0.7303	Intermediate Similarity	NPD5330	Approved
0.7303	Intermediate Similarity	NPD7521	Approved
0.7303	Intermediate Similarity	NPD7334	Approved
0.7303	Intermediate Similarity	NPD6098	Approved
0.7303	Intermediate Similarity	NPD6409	Approved
0.7303	Intermediate Similarity	NPD6684	Approved
0.7303	Intermediate Similarity	NPD7146	Approved
0.7292	Intermediate Similarity	NPD4700	Approved
0.7283	Intermediate Similarity	NPD5693	Phase 1
0.7245	Intermediate Similarity	NPD5175	Approved
0.7245	Intermediate Similarity	NPD5174	Approved
0.7209	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6399	Phase 3
0.7179	Intermediate Similarity	NPD7341	Phase 2
0.7174	Intermediate Similarity	NPD5207	Approved
0.7172	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD5208	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7902	Approved
0.7071	Intermediate Similarity	NPD4754	Approved
0.7053	Intermediate Similarity	NPD5654	Approved
0.703	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD1696	Phase 3
0.6966	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6011	Approved
0.6961	Remote Similarity	NPD4729	Approved
0.6961	Remote Similarity	NPD4730	Approved
0.6961	Remote Similarity	NPD5168	Approved
0.6961	Remote Similarity	NPD5128	Approved
0.6961	Remote Similarity	NPD6899	Approved
0.6961	Remote Similarity	NPD6881	Approved
0.6941	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6404	Discontinued
0.6932	Remote Similarity	NPD8028	Phase 2
0.6931	Remote Similarity	NPD4768	Approved
0.6931	Remote Similarity	NPD5739	Approved
0.6931	Remote Similarity	NPD6675	Approved
0.6931	Remote Similarity	NPD6402	Approved
0.6931	Remote Similarity	NPD7128	Approved
0.6931	Remote Similarity	NPD4767	Approved
0.6907	Remote Similarity	NPD5959	Approved
0.6905	Remote Similarity	NPD4784	Approved
0.6905	Remote Similarity	NPD4785	Approved
0.6893	Remote Similarity	NPD6014	Approved
0.6893	Remote Similarity	NPD6012	Approved
0.6893	Remote Similarity	NPD6013	Approved
0.6875	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4243	Approved
0.6863	Remote Similarity	NPD5701	Approved
0.6854	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD287	Approved
0.6827	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5251	Approved
0.6827	Remote Similarity	NPD5169	Approved
0.6827	Remote Similarity	NPD5250	Approved
0.6827	Remote Similarity	NPD5249	Phase 3
0.6827	Remote Similarity	NPD7290	Approved
0.6827	Remote Similarity	NPD4634	Approved
0.6827	Remote Similarity	NPD6883	Approved
0.6827	Remote Similarity	NPD7102	Approved
0.6827	Remote Similarity	NPD5248	Approved
0.6827	Remote Similarity	NPD5247	Approved
0.6827	Remote Similarity	NPD5135	Approved
0.6824	Remote Similarity	NPD6942	Approved
0.6824	Remote Similarity	NPD7339	Approved
0.6804	Remote Similarity	NPD7732	Phase 3
0.6796	Remote Similarity	NPD7320	Approved
0.6771	Remote Similarity	NPD6001	Approved
0.6771	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7900	Approved
0.6771	Remote Similarity	NPD5282	Discontinued
0.6762	Remote Similarity	NPD6869	Approved
0.6762	Remote Similarity	NPD6649	Approved
0.6762	Remote Similarity	NPD6847	Approved
0.6762	Remote Similarity	NPD8130	Phase 1
0.6762	Remote Similarity	NPD6650	Approved
0.6762	Remote Similarity	NPD6617	Approved
0.6762	Remote Similarity	NPD5215	Approved
0.6762	Remote Similarity	NPD5216	Approved
0.6762	Remote Similarity	NPD5127	Approved
0.6762	Remote Similarity	NPD5217	Approved
0.6737	Remote Similarity	NPD6411	Approved
0.6731	Remote Similarity	NPD6372	Approved
0.6731	Remote Similarity	NPD6373	Approved
0.6701	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6882	Approved
0.6698	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD3704	Approved
0.6667	Remote Similarity	NPD4756	Discovery
0.6636	Remote Similarity	NPD4632	Approved
0.663	Remote Similarity	NPD1694	Approved
0.6628	Remote Similarity	NPD5275	Approved
0.6628	Remote Similarity	NPD4190	Phase 3
0.6604	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5167	Approved
0.6548	Remote Similarity	NPD4789	Approved
0.6538	Remote Similarity	NPD6412	Phase 2
0.6538	Remote Similarity	NPD6614	Approved
0.6526	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6101	Approved
0.6517	Remote Similarity	NPD7645	Phase 2
0.6514	Remote Similarity	NPD6274	Approved
0.6514	Remote Similarity	NPD6868	Approved
0.6463	Remote Similarity	NPD4224	Phase 2
0.6455	Remote Similarity	NPD6009	Approved
0.6455	Remote Similarity	NPD6317	Approved
0.6452	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6335	Approved
0.6396	Remote Similarity	NPD6313	Approved
0.6396	Remote Similarity	NPD6314	Approved
0.6341	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7101	Approved
0.6339	Remote Similarity	NPD4522	Approved
0.6339	Remote Similarity	NPD7100	Approved
0.6337	Remote Similarity	NPD7638	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