NPASS Compound

Structure

NPC30462 OpenBabel07101719512D 23 25 0 0 1 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 -3.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 -4.3301 -1.5000 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 -0.0000 -3.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 1 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 -0.0000 -2.0000 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 -0.8660 -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 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 13 2 1 6 0 0 0 13 20 1 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.16
Volume:	336.722
LogP:	4.294
LogD:	3.766
LogS:	-4.782
# Rotatable Bonds:	3
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.901
Synthetic Accessibility Score:	3.167
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.931
MDCK Permeability:	1.728399729472585e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.043
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	97.56754302978516%
Volume Distribution (VD):	1.823
Pgp-substrate:	2.043712615966797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.294
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.829
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.855
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.314
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.8
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	11.966
Half-life (T1/2):	0.35

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.845
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.252
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.731
Carcinogencity:	0.131
Eye Corrosion:	0.004
Eye Irritation:	0.32
Respiratory Toxicity:	0.704

Download Data

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

Natural Product: NPC30462

Natural Product ID:	NPC30462
*Common Name:**	Pycnanthulignene A
IUPAC Name:	4-[(1S,2R)-6,7-dimethoxy-2,3-dimethyl-1,2-dihydronaphthalen-1-yl]phenol
Synonyms:
Standard InCHIKey:	HCDYEUTVLWYHQC-RBZFPXEDSA-N
Standard InCHI:	InChI=1S/C20H22O3/c1-12-9-15-10-18(22-3)19(23-4)11-17(15)20(13(12)2)14-5-7-16(21)8-6-14/h5-11,13,20-21H,1-4H3/t13-,20-/m0/s1
SMILES:	CC1=Cc2cc(c(cc2[C@@H]([C@H]1C)c1ccc(cc1)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087927
PubChem CID:	46186375
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO15668	Pycnanthus angolensis	Species	Myristicaceae	Eukaryota	roots	n.a.	n.a.	PMID[20055477]
NPO15668	Pycnanthus angolensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21495101]
NPO15668	Pycnanthus angolensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	9
Others	9

Activity Type	# Activity
Organism	18

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4737	Organism	Microsporum audouinii	Microsporum audouinii	MMC	=	78.12	ug ml-1	PMID[463374]
NPT20	Organism	Candida albicans	Candida albicans	MMC	=	39.06	ug ml-1	PMID[463374]
NPT2897	Organism	Citrobacter freundii	Citrobacter freundii	MMC	=	78.12	ug ml-1	PMID[463374]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MMC	=	39.06	ug ml-1	PMID[463374]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MMC	>	78.12	ug ml-1	PMID[463374]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MMC	>	78.12	ug ml-1	PMID[463374]
NPT3152	Organism	Shigella dysenteriae	Shigella dysenteriae	MMC	=	78.1	ug ml-1	PMID[463374]
NPT19	Organism	Escherichia coli	Escherichia coli	MMC	=	39.1	ug ml-1	PMID[463374]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MMC	=	19.53	ug ml-1	PMID[463374]
NPT4737	Organism	Microsporum audouinii	Microsporum audouinii	MIC	=	39.06	ug.mL-1	PMID[463374]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	19.53	ug.mL-1	PMID[463374]
NPT2897	Organism	Citrobacter freundii	Citrobacter freundii	MIC	=	39.06	ug.mL-1	PMID[463374]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	19.53	ug.mL-1	PMID[463374]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	78.12	ug.mL-1	PMID[463374]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	78.12	ug.mL-1	PMID[463374]
NPT3152	Organism	Shigella dysenteriae	Shigella dysenteriae	MIC	=	39.1	ug.mL-1	PMID[463374]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	19.5	ug.mL-1	PMID[463374]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	9.76	ug.mL-1	PMID[463374]

☑ 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 NPC30462 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	336
0.1-0.2	1719
0.2-0.3	4196
0.3-0.4	13184
0.4-0.5	5070
0.5-0.6	5541
0.6-0.7	8553
0.7-0.8	3194
0.8-0.85	707
0.85-0.9	164
0.9-0.95	28
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9746	High Similarity	NPC9067
0.958	High Similarity	NPC228771
0.958	High Similarity	NPC29008
0.958	High Similarity	NPC266705
0.9344	High Similarity	NPC307050
0.9344	High Similarity	NPC277458
0.9316	High Similarity	NPC310338
0.9316	High Similarity	NPC281298
0.9237	High Similarity	NPC242885
0.9237	High Similarity	NPC232316
0.9237	High Similarity	NPC95614
0.9237	High Similarity	NPC56214
0.9237	High Similarity	NPC227217
0.9237	High Similarity	NPC117780
0.9237	High Similarity	NPC165133
0.9138	High Similarity	NPC47194
0.9083	High Similarity	NPC160380
0.9083	High Similarity	NPC38996
0.9068	High Similarity	NPC470626
0.9068	High Similarity	NPC474040
0.9048	High Similarity	NPC227002
0.9008	High Similarity	NPC85488
0.8983	High Similarity	NPC293619
0.8966	High Similarity	NPC165106
0.8934	High Similarity	NPC280704
0.8934	High Similarity	NPC31344
0.8934	High Similarity	NPC317769
0.8934	High Similarity	NPC249788
0.8917	High Similarity	NPC103916
0.8906	High Similarity	NPC311256
0.8906	High Similarity	NPC209199
0.8906	High Similarity	NPC471942
0.8898	High Similarity	NPC14224
0.8898	High Similarity	NPC161958
0.888	High Similarity	NPC201069
0.8843	High Similarity	NPC207613
0.8837	High Similarity	NPC313081
0.8814	High Similarity	NPC473264
0.8814	High Similarity	NPC475815
0.88	High Similarity	NPC106511
0.879	High Similarity	NPC148627
0.879	High Similarity	NPC17348
0.877	High Similarity	NPC324571
0.877	High Similarity	NPC54872
0.877	High Similarity	NPC470212
0.877	High Similarity	NPC312675
0.877	High Similarity	NPC473853
0.877	High Similarity	NPC113865
0.877	High Similarity	NPC262156
0.877	High Similarity	NPC184651
0.877	High Similarity	NPC343720
0.875	High Similarity	NPC474214
0.875	High Similarity	NPC321502
0.875	High Similarity	NPC189482
0.875	High Similarity	NPC228843
0.8739	High Similarity	NPC9341
0.8739	High Similarity	NPC81067
0.873	High Similarity	NPC23012
0.872	High Similarity	NPC274356
0.8696	High Similarity	NPC75440
0.8696	High Similarity	NPC201959
0.8692	High Similarity	NPC200557
0.8692	High Similarity	NPC294884
0.8692	High Similarity	NPC69029
0.8692	High Similarity	NPC108198
0.8692	High Similarity	NPC158142
0.8692	High Similarity	NPC10314
0.8689	High Similarity	NPC129176
0.8678	High Similarity	NPC474320
0.8667	High Similarity	NPC86947
0.8667	High Similarity	NPC164386
0.8651	High Similarity	NPC177167
0.8651	High Similarity	NPC118533
0.8651	High Similarity	NPC165045
0.8651	High Similarity	NPC127587
0.8651	High Similarity	NPC5428
0.8651	High Similarity	NPC21563
0.8647	High Similarity	NPC78987
0.8647	High Similarity	NPC82336
0.8636	High Similarity	NPC184613
0.8632	High Similarity	NPC8547
0.8632	High Similarity	NPC173746
0.8632	High Similarity	NPC156840
0.8632	High Similarity	NPC257124
0.8629	High Similarity	NPC282496
0.8629	High Similarity	NPC233526
0.8629	High Similarity	NPC471693
0.8626	High Similarity	NPC143139
0.8626	High Similarity	NPC202846
0.8626	High Similarity	NPC205442
0.8618	High Similarity	NPC290451
0.8618	High Similarity	NPC127389
0.8615	High Similarity	NPC141023
0.8615	High Similarity	NPC125649
0.8594	High Similarity	NPC126836
0.8583	High Similarity	NPC184733
0.8583	High Similarity	NPC11258
0.8583	High Similarity	NPC128208
0.8583	High Similarity	NPC129570
0.8583	High Similarity	NPC282703
0.8583	High Similarity	NPC45774
0.8583	High Similarity	NPC21867
0.8571	High Similarity	NPC304630
0.8571	High Similarity	NPC76451
0.8571	High Similarity	NPC17837
0.8561	High Similarity	NPC242715
0.8561	High Similarity	NPC56329
0.8561	High Similarity	NPC266006
0.855	High Similarity	NPC252343
0.855	High Similarity	NPC241241
0.8548	High Similarity	NPC41562
0.8548	High Similarity	NPC152946
0.8547	High Similarity	NPC137685
0.8538	High Similarity	NPC227719
0.8534	High Similarity	NPC11554
0.8525	High Similarity	NPC24474
0.8525	High Similarity	NPC311595
0.8522	High Similarity	NPC113457
0.8516	High Similarity	NPC190144
0.8516	High Similarity	NPC475875
0.8507	High Similarity	NPC29599
0.8504	High Similarity	NPC100129
0.8496	Intermediate Similarity	NPC29868
0.8496	Intermediate Similarity	NPC275061
0.8496	Intermediate Similarity	NPC6300
0.8496	Intermediate Similarity	NPC212942
0.8496	Intermediate Similarity	NPC114171
0.8496	Intermediate Similarity	NPC230124
0.8496	Intermediate Similarity	NPC132804
0.8496	Intermediate Similarity	NPC79622
0.8496	Intermediate Similarity	NPC220344
0.8496	Intermediate Similarity	NPC243996
0.8492	Intermediate Similarity	NPC251855
0.8492	Intermediate Similarity	NPC208950
0.8492	Intermediate Similarity	NPC472093
0.8492	Intermediate Similarity	NPC257589
0.8492	Intermediate Similarity	NPC203133
0.8492	Intermediate Similarity	NPC193544
0.8492	Intermediate Similarity	NPC116907
0.8492	Intermediate Similarity	NPC117214
0.8492	Intermediate Similarity	NPC76119
0.8492	Intermediate Similarity	NPC53305
0.8492	Intermediate Similarity	NPC221077
0.8492	Intermediate Similarity	NPC4286
0.8492	Intermediate Similarity	NPC57490
0.8492	Intermediate Similarity	NPC475169
0.8492	Intermediate Similarity	NPC17943
0.8492	Intermediate Similarity	NPC298757
0.8492	Intermediate Similarity	NPC105925
0.8492	Intermediate Similarity	NPC233410
0.8487	Intermediate Similarity	NPC141003
0.8487	Intermediate Similarity	NPC35344
0.8485	Intermediate Similarity	NPC30632
0.848	Intermediate Similarity	NPC228922
0.848	Intermediate Similarity	NPC197757
0.8473	Intermediate Similarity	NPC160697
0.8462	Intermediate Similarity	NPC36108
0.8462	Intermediate Similarity	NPC73656
0.8462	Intermediate Similarity	NPC7097
0.8462	Intermediate Similarity	NPC246358
0.8462	Intermediate Similarity	NPC233731
0.8455	Intermediate Similarity	NPC344161
0.8455	Intermediate Similarity	NPC474565
0.845	Intermediate Similarity	NPC187998
0.845	Intermediate Similarity	NPC275950
0.845	Intermediate Similarity	NPC181079
0.845	Intermediate Similarity	NPC64201
0.845	Intermediate Similarity	NPC42300
0.845	Intermediate Similarity	NPC77040
0.845	Intermediate Similarity	NPC192687
0.845	Intermediate Similarity	NPC174495
0.845	Intermediate Similarity	NPC92164
0.845	Intermediate Similarity	NPC145305
0.845	Intermediate Similarity	NPC173308
0.845	Intermediate Similarity	NPC224157
0.845	Intermediate Similarity	NPC257582
0.845	Intermediate Similarity	NPC241522
0.845	Intermediate Similarity	NPC242807
0.845	Intermediate Similarity	NPC143483
0.845	Intermediate Similarity	NPC153739
0.8438	Intermediate Similarity	NPC472968
0.8438	Intermediate Similarity	NPC245826
0.8438	Intermediate Similarity	NPC470084
0.8438	Intermediate Similarity	NPC252307
0.8438	Intermediate Similarity	NPC474178
0.8433	Intermediate Similarity	NPC308768
0.8433	Intermediate Similarity	NPC12668
0.843	Intermediate Similarity	NPC312105
0.8425	Intermediate Similarity	NPC92207
0.8425	Intermediate Similarity	NPC206882
0.8425	Intermediate Similarity	NPC127937
0.8425	Intermediate Similarity	NPC223953
0.8425	Intermediate Similarity	NPC170485
0.8421	Intermediate Similarity	NPC266453
0.8421	Intermediate Similarity	NPC200935
0.8421	Intermediate Similarity	NPC22902
0.8421	Intermediate Similarity	NPC230919
0.8413	Intermediate Similarity	NPC206487
0.8413	Intermediate Similarity	NPC114901
0.8413	Intermediate Similarity	NPC5796

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 NPC30462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	1020
0.2-0.3	1311
0.3-0.4	2699
0.4-0.5	1868
0.5-0.6	1030
0.6-0.7	684
0.7-0.8	198
0.8-0.85	14
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8966	High Similarity	NPD5283	Phase 1
0.875	High Similarity	NPD3619	Clinical (unspecified phase)
0.875	High Similarity	NPD3620	Phase 2
0.8632	High Similarity	NPD228	Approved
0.848	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD3022	Approved
0.8305	Intermediate Similarity	NPD3021	Approved
0.8231	Intermediate Similarity	NPD3027	Phase 3
0.8189	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4060	Phase 1
0.814	Intermediate Similarity	NPD4624	Approved
0.803	Intermediate Similarity	NPD5110	Phase 2
0.803	Intermediate Similarity	NPD5109	Approved
0.803	Intermediate Similarity	NPD5111	Phase 2
0.8016	Intermediate Similarity	NPD4626	Approved
0.8	Intermediate Similarity	NPD3020	Approved
0.7985	Intermediate Similarity	NPD3657	Discovery
0.7984	Intermediate Similarity	NPD1283	Approved
0.7937	Intermediate Similarity	NPD1651	Approved
0.792	Intermediate Similarity	NPD5536	Phase 2
0.7907	Intermediate Similarity	NPD5327	Phase 3
0.7857	Intermediate Similarity	NPD3091	Approved
0.7852	Intermediate Similarity	NPD5735	Approved
0.782	Intermediate Similarity	NPD4625	Phase 3
0.7803	Intermediate Similarity	NPD2861	Phase 2
0.7795	Intermediate Similarity	NPD1357	Approved
0.7794	Intermediate Similarity	NPD4097	Suspended
0.7786	Intermediate Similarity	NPD6331	Phase 2
0.7778	Intermediate Similarity	NPD4140	Approved
0.7769	Intermediate Similarity	NPD2684	Approved
0.7769	Intermediate Similarity	NPD1669	Approved
0.7752	Intermediate Similarity	NPD3705	Approved
0.7752	Intermediate Similarity	NPD1281	Approved
0.7752	Intermediate Similarity	NPD3092	Approved
0.7744	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD2860	Approved
0.7739	Intermediate Similarity	NPD2859	Approved
0.7734	Intermediate Similarity	NPD2932	Approved
0.773	Intermediate Similarity	NPD5241	Discontinued
0.7727	Intermediate Similarity	NPD6584	Phase 3
0.7705	Intermediate Similarity	NPD5451	Approved
0.7692	Intermediate Similarity	NPD2230	Approved
0.7692	Intermediate Similarity	NPD2232	Approved
0.7692	Intermediate Similarity	NPD2233	Approved
0.7669	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD6353	Approved
0.7664	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7635	Approved
0.7656	Intermediate Similarity	NPD5691	Approved
0.7652	Intermediate Similarity	NPD2933	Approved
0.7652	Intermediate Similarity	NPD2934	Approved
0.7647	Intermediate Similarity	NPD1613	Approved
0.7647	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7037	Approved
0.7639	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD2983	Phase 2
0.7634	Intermediate Similarity	NPD4749	Approved
0.7634	Intermediate Similarity	NPD2982	Phase 2
0.763	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6671	Approved
0.7619	Intermediate Similarity	NPD7157	Approved
0.7615	Intermediate Similarity	NPD1610	Phase 2
0.7612	Intermediate Similarity	NPD4908	Phase 1
0.76	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7833	Phase 2
0.76	Intermediate Similarity	NPD7831	Phase 2
0.7597	Intermediate Similarity	NPD2667	Approved
0.7597	Intermediate Similarity	NPD2668	Approved
0.7597	Intermediate Similarity	NPD3019	Approved
0.7597	Intermediate Similarity	NPD4059	Approved
0.7594	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6674	Discontinued
0.7574	Intermediate Similarity	NPD2674	Phase 3
0.7568	Intermediate Similarity	NPD37	Approved
0.7557	Intermediate Similarity	NPD2981	Phase 2
0.7556	Intermediate Similarity	NPD7095	Approved
0.7554	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7028	Phase 2
0.7541	Intermediate Similarity	NPD2342	Discontinued
0.7537	Intermediate Similarity	NPD3018	Phase 2
0.7535	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4110	Phase 3
0.752	Intermediate Similarity	NPD7843	Approved
0.7519	Intermediate Similarity	NPD3094	Phase 2
0.7519	Intermediate Similarity	NPD4093	Discontinued
0.7518	Intermediate Similarity	NPD1558	Phase 1
0.7518	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3145	Approved
0.75	Intermediate Similarity	NPD6582	Phase 2
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3144	Approved
0.75	Intermediate Similarity	NPD6583	Phase 3
0.75	Intermediate Similarity	NPD5718	Phase 2
0.75	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD6896	Approved
0.7482	Intermediate Similarity	NPD6895	Approved
0.7481	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD709	Approved
0.7465	Intermediate Similarity	NPD5177	Phase 3
0.7465	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD3060	Approved
0.7462	Intermediate Similarity	NPD6516	Phase 2
0.7462	Intermediate Similarity	NPD3095	Discontinued
0.7462	Intermediate Similarity	NPD5846	Approved
0.7459	Intermediate Similarity	NPD968	Approved
0.7434	Intermediate Similarity	NPD6234	Discontinued
0.7429	Intermediate Similarity	NPD4108	Discontinued
0.7422	Intermediate Similarity	NPD7340	Approved
0.7417	Intermediate Similarity	NPD4965	Approved
0.7417	Intermediate Similarity	NPD4967	Phase 2
0.7417	Intermediate Similarity	NPD4966	Approved
0.7413	Intermediate Similarity	NPD8166	Discontinued
0.7413	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5736	Approved
0.7394	Intermediate Similarity	NPD2808	Discontinued
0.7391	Intermediate Similarity	NPD2979	Phase 3
0.7381	Intermediate Similarity	NPD5535	Approved
0.7379	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7041	Phase 2
0.7376	Intermediate Similarity	NPD2161	Phase 2
0.7376	Intermediate Similarity	NPD2438	Suspended
0.7373	Intermediate Similarity	NPD288	Approved
0.735	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD9296	Approved
0.7328	Intermediate Similarity	NPD2286	Discontinued
0.7324	Intermediate Similarity	NPD5763	Approved
0.7324	Intermediate Similarity	NPD5762	Approved
0.7324	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD1398	Phase 1
0.7319	Intermediate Similarity	NPD8032	Phase 2
0.7313	Intermediate Similarity	NPD2922	Phase 1
0.7313	Intermediate Similarity	NPD8651	Approved
0.7313	Intermediate Similarity	NPD6696	Suspended
0.7308	Intermediate Similarity	NPD2489	Approved
0.7308	Intermediate Similarity	NPD27	Approved
0.7308	Intermediate Similarity	NPD1548	Phase 1
0.7299	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7003	Approved
0.729	Intermediate Similarity	NPD6232	Discontinued
0.7288	Intermediate Similarity	NPD844	Approved
0.728	Intermediate Similarity	NPD4750	Phase 3
0.7279	Intermediate Similarity	NPD9494	Approved
0.7273	Intermediate Similarity	NPD3847	Discontinued
0.7266	Intermediate Similarity	NPD3110	Approved
0.7266	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3109	Approved
0.7266	Intermediate Similarity	NPD2238	Phase 2
0.7261	Intermediate Similarity	NPD7473	Discontinued
0.7248	Intermediate Similarity	NPD4005	Discontinued
0.7246	Intermediate Similarity	NPD1039	Discontinued
0.7244	Intermediate Similarity	NPD2969	Approved
0.7244	Intermediate Similarity	NPD2970	Approved
0.7218	Intermediate Similarity	NPD1611	Approved
0.7214	Intermediate Similarity	NPD6355	Discontinued
0.7211	Intermediate Similarity	NPD4584	Approved
0.7197	Intermediate Similarity	NPD1751	Approved
0.7194	Intermediate Similarity	NPD6663	Approved
0.7185	Intermediate Similarity	NPD1876	Approved
0.7171	Intermediate Similarity	NPD5929	Approved
0.7164	Intermediate Similarity	NPD2231	Phase 2
0.7164	Intermediate Similarity	NPD1840	Phase 2
0.7164	Intermediate Similarity	NPD2235	Phase 2
0.7164	Intermediate Similarity	NPD1608	Approved
0.7163	Intermediate Similarity	NPD2157	Approved
0.7162	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD1792	Phase 2
0.7133	Intermediate Similarity	NPD2531	Phase 2
0.7133	Intermediate Similarity	NPD2935	Discontinued
0.7132	Intermediate Similarity	NPD2797	Approved
0.7122	Intermediate Similarity	NPD6798	Discontinued
0.7122	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3444	Approved
0.7121	Intermediate Similarity	NPD3445	Approved
0.7121	Intermediate Similarity	NPD3443	Approved
0.7121	Intermediate Similarity	NPD5585	Approved
0.712	Intermediate Similarity	NPD290	Approved
0.7119	Intermediate Similarity	NPD845	Approved
0.7113	Intermediate Similarity	NPD4536	Approved
0.7113	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4538	Approved
0.7109	Intermediate Similarity	NPD821	Approved
0.7107	Intermediate Similarity	NPD7228	Approved
0.7103	Intermediate Similarity	NPD4236	Phase 3
0.7103	Intermediate Similarity	NPD4237	Approved
0.7103	Intermediate Similarity	NPD4162	Approved
0.7095	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6387	Discontinued
0.7075	Intermediate Similarity	NPD7124	Phase 2
0.7071	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3051	Approved
0.7054	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2234	Approved
0.7054	Intermediate Similarity	NPD2229	Approved
0.7054	Intermediate Similarity	NPD2228	Approved
0.7051	Intermediate Similarity	NPD7201	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