NPASS Compound

Structure

CID237667 OpenBabel06191716042D 29 30 0 0 0 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -1.7321 -3.0000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 -4.3301 0.5000 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 -6.0622 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 13 1 0 0 0 0 9 17 2 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 19 2 0 0 0 0 14 24 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 18 23 2 0 0 0 0 19 21 1 0 0 0 0 20 26 1 0 0 0 0 21 22 2 0 0 0 0 22 25 1 0 0 0 0 23 27 1 0 0 0 0 24 25 2 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.23
Volume:	437.912
LogP:	6.691
LogD:	4.093
LogS:	-3.123
# Rotatable Bonds:	8
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.341
Synthetic Accessibility Score:	2.967
Fsp3:	0.36
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.091
MDCK Permeability:	2.1083589672343805e-05
Pgp-inhibitor:	0.211
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	98.91864013671875%
Volume Distribution (VD):	4.805
Pgp-substrate:	1.947370171546936%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.193
CYP2C19-inhibitor:	0.915
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.676
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.947
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.299
CYP3A4-substrate:	0.118

ADMET: Excretion

Clearance (CL):	18.047
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.709
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.151
Maximum Recommended Daily Dose:	0.216
Skin Sensitization:	0.962
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.89
Respiratory Toxicity:	0.213

Download Data

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

Natural Product: NPC237667

Natural Product ID:	NPC237667
*Common Name:**	Kazinol F
IUPAC Name:	5-[3-(2,4-dihydroxyphenyl)propyl]-3,4-bis(3-methylbut-2-enyl)benzene-1,2-diol
Synonyms:	Kazinol F
Standard InCHIKey:	PNQQDEFGJPUAGZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H32O4/c1-16(2)8-12-21-19(7-5-6-18-10-11-20(26)15-23(18)27)14-24(28)25(29)22(21)13-9-17(3)4/h8-11,14-15,26-29H,5-7,12-13H2,1-4H3
SMILES:	CC(=CCc1c(CCCc2ccc(cc2O)O)cc(c(c1CC=C(C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457677
PubChem CID:	184311
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[11575957]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19046886]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20493686]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917310]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	3
IC50	2
Ki	3

Activity Type	# Activity
Cell Line	3
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[548085]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[548085]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[548085]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	960.0	nM	PMID[548086]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	180.8	nM	PMID[548086]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	410.0	nM	PMID[548086]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	1700.0	nM	PMID[548086]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	770.0	nM	PMID[548086]

☑ 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 NPC237667 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	365
0.1-0.2	1737
0.2-0.3	4875
0.3-0.4	13449
0.4-0.5	5356
0.5-0.6	5150
0.6-0.7	8271
0.7-0.8	2938
0.8-0.85	438
0.85-0.9	95
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC53567
0.9737	High Similarity	NPC217174
0.9569	High Similarity	NPC24125
0.9561	High Similarity	NPC277588
0.9487	High Similarity	NPC39029
0.9412	High Similarity	NPC224342
0.9397	High Similarity	NPC191866
0.931	High Similarity	NPC144343
0.9298	High Similarity	NPC107240
0.9217	High Similarity	NPC472893
0.9194	High Similarity	NPC15543
0.9153	High Similarity	NPC472071
0.9123	High Similarity	NPC43525
0.9048	High Similarity	NPC474453
0.9035	High Similarity	NPC4493
0.9035	High Similarity	NPC225679
0.9035	High Similarity	NPC165770
0.9035	High Similarity	NPC268032
0.9035	High Similarity	NPC476632
0.8992	High Similarity	NPC475245
0.8898	High Similarity	NPC470760
0.8879	High Similarity	NPC263753
0.8879	High Similarity	NPC117846
0.8833	High Similarity	NPC223451
0.8814	High Similarity	NPC115808
0.881	High Similarity	NPC126836
0.8793	High Similarity	NPC166995
0.8772	High Similarity	NPC34864
0.8772	High Similarity	NPC114392
0.8772	High Similarity	NPC105727
0.8772	High Similarity	NPC63698
0.8772	High Similarity	NPC61885
0.8772	High Similarity	NPC58427
0.875	High Similarity	NPC176893
0.872	High Similarity	NPC252131
0.8696	High Similarity	NPC254833
0.8696	High Similarity	NPC202647
0.8696	High Similarity	NPC228343
0.8684	High Similarity	NPC176527
0.8651	High Similarity	NPC28765
0.8636	High Similarity	NPC234568
0.8636	High Similarity	NPC198038
0.8632	High Similarity	NPC471179
0.8626	High Similarity	NPC242715
0.8626	High Similarity	NPC56329
0.8621	High Similarity	NPC224870
0.8615	High Similarity	NPC69029
0.8615	High Similarity	NPC108198
0.8615	High Similarity	NPC200557
0.8615	High Similarity	NPC294884
0.8615	High Similarity	NPC10314
0.8615	High Similarity	NPC313081
0.8615	High Similarity	NPC158142
0.8615	High Similarity	NPC241241
0.8609	High Similarity	NPC233835
0.8605	High Similarity	NPC32778
0.8596	High Similarity	NPC39097
0.8596	High Similarity	NPC39664
0.8596	High Similarity	NPC118286
0.8596	High Similarity	NPC109691
0.8596	High Similarity	NPC470700
0.8596	High Similarity	NPC302681
0.8583	High Similarity	NPC16030
0.8571	High Similarity	NPC324112
0.8571	High Similarity	NPC246620
0.8571	High Similarity	NPC282000
0.8571	High Similarity	NPC74817
0.8571	High Similarity	NPC246760
0.8571	High Similarity	NPC159968
0.8571	High Similarity	NPC82679
0.8571	High Similarity	NPC293054
0.8571	High Similarity	NPC169474
0.8571	High Similarity	NPC84999
0.8571	High Similarity	NPC124452
0.8571	High Similarity	NPC236791
0.8571	High Similarity	NPC474486
0.8561	High Similarity	NPC32630
0.8561	High Similarity	NPC220344
0.8561	High Similarity	NPC243996
0.8561	High Similarity	NPC132804
0.8561	High Similarity	NPC275061
0.856	High Similarity	NPC33654
0.8559	High Similarity	NPC23804
0.8559	High Similarity	NPC471485
0.855	High Similarity	NPC202846
0.855	High Similarity	NPC143139
0.855	High Similarity	NPC30632
0.8548	High Similarity	NPC136319
0.8547	High Similarity	NPC224527
0.8538	High Similarity	NPC209199
0.8538	High Similarity	NPC125649
0.8534	High Similarity	NPC33728
0.8534	High Similarity	NPC19808
0.8522	High Similarity	NPC54844
0.8509	High Similarity	NPC292452
0.8509	High Similarity	NPC134829
0.8509	High Similarity	NPC246056
0.8509	High Similarity	NPC474839
0.8504	High Similarity	NPC154866
0.8496	Intermediate Similarity	NPC12668
0.8496	Intermediate Similarity	NPC308768
0.8492	Intermediate Similarity	NPC223136
0.8492	Intermediate Similarity	NPC103823
0.8492	Intermediate Similarity	NPC214406
0.8492	Intermediate Similarity	NPC44748
0.8492	Intermediate Similarity	NPC18924
0.8492	Intermediate Similarity	NPC28730
0.8492	Intermediate Similarity	NPC78974
0.8487	Intermediate Similarity	NPC120280
0.8485	Intermediate Similarity	NPC266453
0.8485	Intermediate Similarity	NPC200935
0.8485	Intermediate Similarity	NPC230919
0.8485	Intermediate Similarity	NPC35550
0.8485	Intermediate Similarity	NPC22902
0.8473	Intermediate Similarity	NPC256262
0.8468	Intermediate Similarity	NPC471794
0.845	Intermediate Similarity	NPC232275
0.8448	Intermediate Similarity	NPC174981
0.8444	Intermediate Similarity	NPC474104
0.8443	Intermediate Similarity	NPC151197
0.8438	Intermediate Similarity	NPC212015
0.8435	Intermediate Similarity	NPC248904
0.8433	Intermediate Similarity	NPC71046
0.8433	Intermediate Similarity	NPC265075
0.8425	Intermediate Similarity	NPC266555
0.8425	Intermediate Similarity	NPC127587
0.8421	Intermediate Similarity	NPC184613
0.8421	Intermediate Similarity	NPC218131
0.8421	Intermediate Similarity	NPC30506
0.8421	Intermediate Similarity	NPC102216
0.8421	Intermediate Similarity	NPC471511
0.8421	Intermediate Similarity	NPC243759
0.8421	Intermediate Similarity	NPC29868
0.8421	Intermediate Similarity	NPC212942
0.8421	Intermediate Similarity	NPC119860
0.8421	Intermediate Similarity	NPC241891
0.8421	Intermediate Similarity	NPC105847
0.8421	Intermediate Similarity	NPC79622
0.8413	Intermediate Similarity	NPC208950
0.8413	Intermediate Similarity	NPC82483
0.8413	Intermediate Similarity	NPC105925
0.8413	Intermediate Similarity	NPC233410
0.8413	Intermediate Similarity	NPC472093
0.8413	Intermediate Similarity	NPC251855
0.8413	Intermediate Similarity	NPC117214
0.8413	Intermediate Similarity	NPC298757
0.8413	Intermediate Similarity	NPC203133
0.8413	Intermediate Similarity	NPC116907
0.8413	Intermediate Similarity	NPC193544
0.8413	Intermediate Similarity	NPC17943
0.8413	Intermediate Similarity	NPC265483
0.8413	Intermediate Similarity	NPC221077
0.8413	Intermediate Similarity	NPC234400
0.8413	Intermediate Similarity	NPC105031
0.8413	Intermediate Similarity	NPC57490
0.8413	Intermediate Similarity	NPC475169
0.8413	Intermediate Similarity	NPC60885
0.8413	Intermediate Similarity	NPC299584
0.8409	Intermediate Similarity	NPC234952
0.8403	Intermediate Similarity	NPC317869
0.84	Intermediate Similarity	NPC228922
0.84	Intermediate Similarity	NPC84086
0.84	Intermediate Similarity	NPC121115
0.84	Intermediate Similarity	NPC197757
0.8397	Intermediate Similarity	NPC7515
0.8397	Intermediate Similarity	NPC469659
0.8397	Intermediate Similarity	NPC160697
0.8397	Intermediate Similarity	NPC289258
0.8397	Intermediate Similarity	NPC206737
0.8397	Intermediate Similarity	NPC56764
0.8397	Intermediate Similarity	NPC188378
0.8397	Intermediate Similarity	NPC276026
0.8397	Intermediate Similarity	NPC555
0.839	Intermediate Similarity	NPC179002
0.839	Intermediate Similarity	NPC151537
0.839	Intermediate Similarity	NPC187583
0.839	Intermediate Similarity	NPC95716
0.839	Intermediate Similarity	NPC257430
0.8387	Intermediate Similarity	NPC476633
0.8385	Intermediate Similarity	NPC6451
0.8385	Intermediate Similarity	NPC14224
0.8385	Intermediate Similarity	NPC161958
0.8382	Intermediate Similarity	NPC473845
0.8382	Intermediate Similarity	NPC50250
0.8372	Intermediate Similarity	NPC311680
0.8372	Intermediate Similarity	NPC51840
0.8372	Intermediate Similarity	NPC299221
0.8372	Intermediate Similarity	NPC234488
0.837	Intermediate Similarity	NPC183709
0.837	Intermediate Similarity	NPC175838
0.8362	Intermediate Similarity	NPC158253
0.8362	Intermediate Similarity	NPC232523
0.8362	Intermediate Similarity	NPC204901
0.8361	Intermediate Similarity	NPC206
0.8358	Intermediate Similarity	NPC472090
0.8358	Intermediate Similarity	NPC472903
0.8358	Intermediate Similarity	NPC472092
0.8358	Intermediate Similarity	NPC472091
0.8348	Intermediate Similarity	NPC239291
0.8347	Intermediate Similarity	NPC261973

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 NPC237667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	992
0.2-0.3	1498
0.3-0.4	3056
0.4-0.5	1706
0.5-0.6	1029
0.6-0.7	439
0.7-0.8	76
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD3021	Approved
0.8696	High Similarity	NPD3022	Approved
0.8246	Intermediate Similarity	NPD940	Approved
0.8246	Intermediate Similarity	NPD846	Approved
0.822	Intermediate Similarity	NPD4750	Phase 3
0.8158	Intermediate Similarity	NPD1242	Phase 1
0.8154	Intermediate Similarity	NPD3027	Phase 3
0.8077	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD7635	Approved
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD3020	Approved
0.7879	Intermediate Similarity	NPD4625	Phase 3
0.7836	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD943	Approved
0.7836	Intermediate Similarity	NPD1613	Approved
0.7807	Intermediate Similarity	NPD2859	Approved
0.7807	Intermediate Similarity	NPD2860	Approved
0.775	Intermediate Similarity	NPD2342	Discontinued
0.7719	Intermediate Similarity	NPD2933	Approved
0.7719	Intermediate Similarity	NPD2934	Approved
0.7692	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3094	Phase 2
0.7538	Intermediate Similarity	NPD3092	Approved
0.7537	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD1809	Phase 2
0.75	Intermediate Similarity	NPD844	Approved
0.7482	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD845	Approved
0.7463	Intermediate Similarity	NPD3018	Phase 2
0.7445	Intermediate Similarity	NPD4060	Phase 1
0.7436	Intermediate Similarity	NPD288	Approved
0.7414	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1610	Phase 2
0.7395	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5283	Phase 1
0.7376	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD3091	Approved
0.736	Intermediate Similarity	NPD228	Approved
0.7344	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7390	Discontinued
0.7308	Intermediate Similarity	NPD4093	Discontinued
0.7299	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4749	Approved
0.7293	Intermediate Similarity	NPD2983	Phase 2
0.7293	Intermediate Similarity	NPD2982	Phase 2
0.728	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD3019	Approved
0.7252	Intermediate Similarity	NPD4059	Approved
0.7252	Intermediate Similarity	NPD2932	Approved
0.7252	Intermediate Similarity	NPD2286	Discontinued
0.7239	Intermediate Similarity	NPD5310	Approved
0.7239	Intermediate Similarity	NPD5311	Approved
0.7231	Intermediate Similarity	NPD1548	Phase 1
0.7222	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD2981	Phase 2
0.7194	Intermediate Similarity	NPD3620	Phase 2
0.7194	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD9094	Approved
0.7192	Intermediate Similarity	NPD2421	Approved
0.7192	Intermediate Similarity	NPD2420	Approved
0.7188	Intermediate Similarity	NPD497	Approved
0.7185	Intermediate Similarity	NPD3055	Approved
0.7185	Intermediate Similarity	NPD3053	Approved
0.7183	Intermediate Similarity	NPD5408	Approved
0.7183	Intermediate Similarity	NPD5404	Approved
0.7183	Intermediate Similarity	NPD5406	Approved
0.7183	Intermediate Similarity	NPD5405	Approved
0.7174	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD9377	Approved
0.7165	Intermediate Similarity	NPD9379	Approved
0.7164	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7133	Intermediate Similarity	NPD7266	Discontinued
0.7122	Intermediate Similarity	NPD6405	Approved
0.7122	Intermediate Similarity	NPD6407	Approved
0.7121	Intermediate Similarity	NPD4626	Approved
0.7121	Intermediate Similarity	NPD4589	Approved
0.7121	Intermediate Similarity	NPD3095	Discontinued
0.7115	Intermediate Similarity	NPD6232	Discontinued
0.7109	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD498	Approved
0.7109	Intermediate Similarity	NPD495	Approved
0.7109	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD496	Approved
0.7099	Intermediate Similarity	NPD5303	Approved
0.7099	Intermediate Similarity	NPD5304	Approved
0.7092	Intermediate Similarity	NPD5314	Approved
0.709	Intermediate Similarity	NPD9269	Phase 2
0.7089	Intermediate Similarity	NPD7473	Discontinued
0.7075	Intermediate Similarity	NPD1511	Approved
0.7071	Intermediate Similarity	NPD3061	Approved
0.7071	Intermediate Similarity	NPD3062	Approved
0.7071	Intermediate Similarity	NPD3059	Approved
0.7063	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1792	Phase 2
0.7059	Intermediate Similarity	NPD1470	Approved
0.7039	Intermediate Similarity	NPD1934	Approved
0.7039	Intermediate Similarity	NPD37	Approved
0.7027	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6671	Approved
0.6993	Remote Similarity	NPD2801	Approved
0.6992	Remote Similarity	NPD1751	Approved
0.6992	Remote Similarity	NPD9384	Approved
0.6992	Remote Similarity	NPD9381	Approved
0.6986	Remote Similarity	NPD8166	Discontinued
0.6985	Remote Similarity	NPD6696	Suspended
0.698	Remote Similarity	NPD1512	Approved
0.6977	Remote Similarity	NPD2229	Approved
0.6977	Remote Similarity	NPD2228	Approved
0.6977	Remote Similarity	NPD2234	Approved
0.6972	Remote Similarity	NPD2568	Approved
0.6972	Remote Similarity	NPD4097	Suspended
0.697	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3028	Approved
0.6957	Remote Similarity	NPD5736	Approved
0.6957	Remote Similarity	NPD2861	Phase 2
0.695	Remote Similarity	NPD1555	Discontinued
0.6944	Remote Similarity	NPD6099	Approved
0.6944	Remote Similarity	NPD6100	Approved
0.6937	Remote Similarity	NPD7228	Approved
0.693	Remote Similarity	NPD111	Approved
0.6929	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6674	Discontinued
0.6912	Remote Similarity	NPD9622	Approved
0.6903	Remote Similarity	NPD4967	Phase 2
0.6903	Remote Similarity	NPD4965	Approved
0.6903	Remote Similarity	NPD4966	Approved
0.6903	Remote Similarity	NPD3882	Suspended
0.6901	Remote Similarity	NPD230	Phase 1
0.6897	Remote Similarity	NPD3540	Phase 1
0.6892	Remote Similarity	NPD3845	Phase 1
0.6889	Remote Similarity	NPD422	Phase 1
0.6883	Remote Similarity	NPD7819	Suspended
0.6871	Remote Similarity	NPD3750	Approved
0.6861	Remote Similarity	NPD8651	Approved
0.6846	Remote Similarity	NPD7041	Phase 2
0.6846	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4005	Discontinued
0.6842	Remote Similarity	NPD7330	Discontinued
0.6838	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7199	Phase 2
0.6831	Remote Similarity	NPD1558	Phase 1
0.6828	Remote Similarity	NPD3539	Phase 1
0.6828	Remote Similarity	NPD2935	Discontinued
0.6825	Remote Similarity	NPD1444	Approved
0.6825	Remote Similarity	NPD1445	Approved
0.6815	Remote Similarity	NPD3026	Approved
0.6815	Remote Similarity	NPD3023	Approved
0.6812	Remote Similarity	NPD1164	Approved
0.68	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD9268	Approved
0.6791	Remote Similarity	NPD1651	Approved
0.6791	Remote Similarity	NPD3024	Approved
0.6791	Remote Similarity	NPD5691	Approved
0.6791	Remote Similarity	NPD3025	Approved
0.679	Remote Similarity	NPD5844	Phase 1
0.6788	Remote Similarity	NPD1669	Approved
0.6783	Remote Similarity	NPD5735	Approved
0.6781	Remote Similarity	NPD5762	Approved
0.6781	Remote Similarity	NPD5763	Approved
0.6779	Remote Similarity	NPD7124	Phase 2
0.6779	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1465	Phase 2
0.6765	Remote Similarity	NPD3705	Approved
0.6763	Remote Similarity	NPD2194	Approved
0.6763	Remote Similarity	NPD258	Approved
0.6763	Remote Similarity	NPD2195	Approved
0.6763	Remote Similarity	NPD9620	Approved
0.6763	Remote Similarity	NPD9619	Approved
0.6763	Remote Similarity	NPD9621	Approved
0.6763	Remote Similarity	NPD257	Approved
0.6761	Remote Similarity	NPD6663	Approved
0.6759	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3892	Phase 2
0.6752	Remote Similarity	NPD4055	Discovery
0.675	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8053	Approved
0.6747	Remote Similarity	NPD8054	Approved
0.6742	Remote Similarity	NPD709	Approved
0.6742	Remote Similarity	NPD7157	Approved
0.6741	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1283	Approved
0.6739	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5155	Approved
0.6738	Remote Similarity	NPD7095	Approved
0.6738	Remote Similarity	NPD5156	Approved
0.6735	Remote Similarity	NPD970	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3635	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