NPASS Compound

Structure

NPC470848 OpenBabel07101718322D 24 25 0 0 1 0 0 0 0 0999 V2000 5.1962 -3.0000 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 6.0622 -0.5000 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 5.1962 1.0000 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 1.7321 -2.0000 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 4.3301 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 2.5981 -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 5.1962 -2.0000 0.0000 C 0 0 3 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 0.8660 -1.5000 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 -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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 3 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 8 1 0 0 0 0 4 14 2 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 24 1 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.13
Volume:	342.927
LogP:	3.458
LogD:	3.447
LogS:	-3.213
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	2.727
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.824
MDCK Permeability:	1.667826290940866e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.708
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	98.5478286743164%
Volume Distribution (VD):	0.544
Pgp-substrate:	0.8471204042434692%

ADMET: Metabolism

CYP1A2-inhibitor:	0.858
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.902
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.785
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.94
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.433
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	16.309
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.953
Carcinogencity:	0.466
Eye Corrosion:	0.008
Eye Irritation:	0.497
Respiratory Toxicity:	0.24

Download Data

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

Natural Product: NPC470848

Natural Product ID:	NPC470848
*Common Name:**	1-Methyl-3-(4'-Hydroxyphenyl)-Propyl Caffeate
IUPAC Name:	4-(4-hydroxyphenyl)butan-2-yl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	SLQHWTMMMMIIMN-YRNVUSSQSA-N
Standard InCHI:	InChI=1S/C19H20O5/c1-13(2-3-14-4-8-16(20)9-5-14)24-19(23)11-7-15-6-10-17(21)18(22)12-15/h4-13,20-22H,2-3H2,1H3/b11-7+
SMILES:	CC(CCC1=CC=C(C=C1)O)OC(=O)C=CC2=CC(=C(C=C2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269338
PubChem CID:	11381853
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO32673	zuccagnia punctata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15161186]

☑ 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

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1276	Organism	Gibberella zeae	Gibberella zeae	MIC	>	50.0	ug.mL-1	PMID[564060]
NPT4304	Organism	Macrophomina phaseolina	Macrophomina phaseolina	MIC	>	50.0	ug.mL-1	PMID[564060]
NPT4635	Organism	Colletotrichum truncatum	Colletotrichum truncatum	MIC	>	50.0	ug.mL-1	PMID[564060]
NPT3685	Organism	Fusarium equiseti	Fusarium equiseti	MIC	>	50.0	ug.mL-1	PMID[564060]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	>	50.0	ug.mL-1	PMID[564060]
NPT4636	Organism	Diaporthe longicolla	Diaporthe longicolla	MIC	=	6.25	ug.mL-1	PMID[564060]

☑ 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 NPC470848 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	242
0.1-0.2	1246
0.2-0.3	3881
0.3-0.4	9533
0.4-0.5	9126
0.5-0.6	5269
0.6-0.7	9783
0.7-0.8	3187
0.8-0.85	319
0.85-0.9	78
0.9-0.95	26
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470849
0.9823	High Similarity	NPC141791
0.9823	High Similarity	NPC263386
0.9735	High Similarity	NPC309434
0.9569	High Similarity	NPC147654
0.9561	High Similarity	NPC275519
0.9561	High Similarity	NPC203124
0.9558	High Similarity	NPC281277
0.9474	High Similarity	NPC145023
0.9474	High Similarity	NPC200988
0.9474	High Similarity	NPC175799
0.9474	High Similarity	NPC610
0.9469	High Similarity	NPC233669
0.9391	High Similarity	NPC86198
0.9381	High Similarity	NPC33749
0.9381	High Similarity	NPC261453
0.9381	High Similarity	NPC328593
0.9333	High Similarity	NPC120225
0.9333	High Similarity	NPC213552
0.931	High Similarity	NPC470215
0.931	High Similarity	NPC70084
0.931	High Similarity	NPC470214
0.931	High Similarity	NPC109371
0.9298	High Similarity	NPC474967
0.9292	High Similarity	NPC95381
0.925	High Similarity	NPC289459
0.9167	High Similarity	NPC246704
0.9138	High Similarity	NPC65791
0.9115	High Similarity	NPC226250
0.9106	High Similarity	NPC83062
0.9043	High Similarity	NPC217472
0.9027	High Similarity	NPC183700
0.9016	High Similarity	NPC118584
0.9008	High Similarity	NPC60517
0.9008	High Similarity	NPC288945
0.9008	High Similarity	NPC20443
0.9008	High Similarity	NPC146886
0.8968	High Similarity	NPC168799
0.8968	High Similarity	NPC155209
0.896	High Similarity	NPC198388
0.8947	High Similarity	NPC297657
0.8934	High Similarity	NPC67951
0.8898	High Similarity	NPC135127
0.8898	High Similarity	NPC106406
0.8889	High Similarity	NPC5419
0.8889	High Similarity	NPC61
0.8889	High Similarity	NPC18074
0.8889	High Similarity	NPC25581
0.8871	High Similarity	NPC110313
0.887	High Similarity	NPC131530
0.8833	High Similarity	NPC204466
0.8814	High Similarity	NPC278652
0.881	High Similarity	NPC318799
0.88	High Similarity	NPC30174
0.8793	High Similarity	NPC264558
0.878	High Similarity	NPC197832
0.877	High Similarity	NPC306100
0.877	High Similarity	NPC285345
0.877	High Similarity	NPC212541
0.8761	High Similarity	NPC260952
0.876	High Similarity	NPC70752
0.876	High Similarity	NPC472271
0.875	High Similarity	NPC287597
0.875	High Similarity	NPC34293
0.875	High Similarity	NPC886
0.875	High Similarity	NPC202474
0.873	High Similarity	NPC329344
0.873	High Similarity	NPC237506
0.873	High Similarity	NPC32626
0.873	High Similarity	NPC217052
0.872	High Similarity	NPC478215
0.8699	High Similarity	NPC469568
0.8696	High Similarity	NPC226401
0.8696	High Similarity	NPC147634
0.8696	High Similarity	NPC174096
0.8696	High Similarity	NPC79793
0.8696	High Similarity	NPC120982
0.8692	High Similarity	NPC126206
0.8684	High Similarity	NPC206341
0.8678	High Similarity	NPC60962
0.8678	High Similarity	NPC224814
0.8678	High Similarity	NPC189844
0.8678	High Similarity	NPC109083
0.8678	High Similarity	NPC14007
0.8678	High Similarity	NPC269843
0.8673	High Similarity	NPC294902
0.8673	High Similarity	NPC1786
0.8673	High Similarity	NPC1075
0.8667	High Similarity	NPC241634
0.8629	High Similarity	NPC87113
0.8626	High Similarity	NPC476383
0.8626	High Similarity	NPC81515
0.8626	High Similarity	NPC197316
0.8626	High Similarity	NPC89105
0.8626	High Similarity	NPC68092
0.8626	High Similarity	NPC64141
0.8626	High Similarity	NPC472350
0.8621	High Similarity	NPC179002
0.8621	High Similarity	NPC187583
0.8621	High Similarity	NPC257430
0.8618	High Similarity	NPC224208
0.8618	High Similarity	NPC474275
0.8615	High Similarity	NPC471664
0.8615	High Similarity	NPC471665
0.8615	High Similarity	NPC154485
0.8615	High Similarity	NPC120852
0.8615	High Similarity	NPC476699
0.8615	High Similarity	NPC90431
0.8615	High Similarity	NPC471872
0.8609	High Similarity	NPC55617
0.8609	High Similarity	NPC62258
0.8595	High Similarity	NPC2058
0.8583	High Similarity	NPC70744
0.8583	High Similarity	NPC277460
0.8583	High Similarity	NPC137537
0.8583	High Similarity	NPC164706
0.8583	High Similarity	NPC272471
0.8583	High Similarity	NPC107588
0.8571	High Similarity	NPC277394
0.8571	High Similarity	NPC299252
0.8571	High Similarity	NPC61062
0.8561	High Similarity	NPC475530
0.8561	High Similarity	NPC473799
0.8561	High Similarity	NPC288452
0.8561	High Similarity	NPC289690
0.855	High Similarity	NPC260425
0.855	High Similarity	NPC67349
0.855	High Similarity	NPC78363
0.855	High Similarity	NPC279676
0.8548	High Similarity	NPC85565
0.8547	High Similarity	NPC51698
0.8537	High Similarity	NPC86900
0.8534	High Similarity	NPC63345
0.8527	High Similarity	NPC475468
0.8525	High Similarity	NPC207613
0.8525	High Similarity	NPC98305
0.8504	High Similarity	NPC477293
0.8504	High Similarity	NPC229784
0.8504	High Similarity	NPC477300
0.8504	High Similarity	NPC477294
0.8504	High Similarity	NPC241354
0.8496	Intermediate Similarity	NPC134405
0.8496	Intermediate Similarity	NPC476385
0.8496	Intermediate Similarity	NPC47471
0.8496	Intermediate Similarity	NPC476377
0.8492	Intermediate Similarity	NPC276466
0.8492	Intermediate Similarity	NPC5018
0.8492	Intermediate Similarity	NPC123722
0.8492	Intermediate Similarity	NPC151167
0.8492	Intermediate Similarity	NPC476873
0.8492	Intermediate Similarity	NPC123228
0.8485	Intermediate Similarity	NPC328273
0.8485	Intermediate Similarity	NPC205195
0.8485	Intermediate Similarity	NPC171134
0.8485	Intermediate Similarity	NPC321638
0.8485	Intermediate Similarity	NPC321184
0.8485	Intermediate Similarity	NPC284409
0.8485	Intermediate Similarity	NPC182249
0.848	Intermediate Similarity	NPC280767
0.8475	Intermediate Similarity	NPC148969
0.8468	Intermediate Similarity	NPC229084
0.8468	Intermediate Similarity	NPC160900
0.8468	Intermediate Similarity	NPC18984
0.8468	Intermediate Similarity	NPC106659
0.8462	Intermediate Similarity	NPC249791
0.8462	Intermediate Similarity	NPC139946
0.8462	Intermediate Similarity	NPC471110
0.8462	Intermediate Similarity	NPC67247
0.8462	Intermediate Similarity	NPC476387
0.8462	Intermediate Similarity	NPC237594
0.8462	Intermediate Similarity	NPC119060
0.8455	Intermediate Similarity	NPC113865
0.8455	Intermediate Similarity	NPC470212
0.8455	Intermediate Similarity	NPC324571
0.8455	Intermediate Similarity	NPC54872
0.8455	Intermediate Similarity	NPC312675
0.8455	Intermediate Similarity	NPC343720
0.8455	Intermediate Similarity	NPC473853
0.8455	Intermediate Similarity	NPC262156
0.8455	Intermediate Similarity	NPC184651
0.845	Intermediate Similarity	NPC473285
0.8448	Intermediate Similarity	NPC228343
0.8448	Intermediate Similarity	NPC254833
0.8448	Intermediate Similarity	NPC79543
0.8438	Intermediate Similarity	NPC285361
0.8433	Intermediate Similarity	NPC67467
0.8433	Intermediate Similarity	NPC140502
0.8433	Intermediate Similarity	NPC222433
0.8433	Intermediate Similarity	NPC265648
0.843	Intermediate Similarity	NPC470626
0.8425	Intermediate Similarity	NPC232880
0.8425	Intermediate Similarity	NPC46192
0.8421	Intermediate Similarity	NPC473591
0.8421	Intermediate Similarity	NPC179505
0.8421	Intermediate Similarity	NPC155192
0.8421	Intermediate Similarity	NPC471875
0.8421	Intermediate Similarity	NPC156709
0.8421	Intermediate Similarity	NPC271494
0.8421	Intermediate Similarity	NPC106055
0.8421	Intermediate Similarity	NPC110699

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 NPC470848 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	828
0.2-0.3	1517
0.3-0.4	2649
0.4-0.5	2007
0.5-0.6	1143
0.6-0.7	699
0.7-0.8	91
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8626	High Similarity	NPD7266	Discontinued
0.8468	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD3021	Approved
0.8448	Intermediate Similarity	NPD3022	Approved
0.8162	Intermediate Similarity	NPD8166	Discontinued
0.8102	Intermediate Similarity	NPD6190	Approved
0.8	Intermediate Similarity	NPD228	Approved
0.7958	Intermediate Similarity	NPD3455	Phase 2
0.7939	Intermediate Similarity	NPD3027	Phase 3
0.7903	Intermediate Similarity	NPD5536	Phase 2
0.7895	Intermediate Similarity	NPD4060	Phase 1
0.7836	Intermediate Similarity	NPD230	Phase 1
0.7815	Intermediate Similarity	NPD1358	Approved
0.7788	Intermediate Similarity	NPD2934	Approved
0.7788	Intermediate Similarity	NPD2933	Approved
0.7731	Intermediate Similarity	NPD3134	Approved
0.7724	Intermediate Similarity	NPD5283	Phase 1
0.7719	Intermediate Similarity	NPD2860	Approved
0.7719	Intermediate Similarity	NPD2859	Approved
0.7672	Intermediate Similarity	NPD3020	Approved
0.7656	Intermediate Similarity	NPD3496	Discontinued
0.763	Intermediate Similarity	NPD826	Approved
0.763	Intermediate Similarity	NPD825	Approved
0.7578	Intermediate Similarity	NPD4626	Approved
0.7559	Intermediate Similarity	NPD9545	Approved
0.7537	Intermediate Similarity	NPD7095	Approved
0.7519	Intermediate Similarity	NPD9494	Approved
0.7519	Intermediate Similarity	NPD5736	Approved
0.7518	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD5535	Approved
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.75	Intermediate Similarity	NPD5691	Approved
0.7483	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2935	Discontinued
0.7481	Intermediate Similarity	NPD6798	Discontinued
0.7445	Intermediate Similarity	NPD555	Phase 2
0.7445	Intermediate Similarity	NPD6355	Discontinued
0.7426	Intermediate Similarity	NPD4062	Phase 3
0.7426	Intermediate Similarity	NPD6233	Phase 2
0.74	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1653	Approved
0.7394	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4110	Phase 3
0.7385	Intermediate Similarity	NPD3847	Discontinued
0.7372	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3620	Phase 2
0.7364	Intermediate Similarity	NPD1357	Approved
0.7353	Intermediate Similarity	NPD3764	Approved
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD4340	Discontinued
0.7317	Intermediate Similarity	NPD2684	Approved
0.7313	Intermediate Similarity	NPD258	Approved
0.7313	Intermediate Similarity	NPD257	Approved
0.7305	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6663	Approved
0.7299	Intermediate Similarity	NPD259	Phase 1
0.7287	Intermediate Similarity	NPD1894	Discontinued
0.7273	Intermediate Similarity	NPD9269	Phase 2
0.7267	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD943	Approved
0.7246	Intermediate Similarity	NPD3062	Approved
0.7246	Intermediate Similarity	NPD3061	Approved
0.7246	Intermediate Similarity	NPD4140	Approved
0.7246	Intermediate Similarity	NPD3059	Approved
0.7239	Intermediate Similarity	NPD3053	Approved
0.7239	Intermediate Similarity	NPD3055	Approved
0.7231	Intermediate Similarity	NPD5585	Approved
0.7222	Intermediate Similarity	NPD7843	Approved
0.7222	Intermediate Similarity	NPD9379	Approved
0.7222	Intermediate Similarity	NPD9377	Approved
0.7218	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1934	Approved
0.7197	Intermediate Similarity	NPD422	Phase 1
0.7197	Intermediate Similarity	NPD3092	Approved
0.7197	Intermediate Similarity	NPD1535	Discovery
0.7188	Intermediate Similarity	NPD4198	Discontinued
0.7188	Intermediate Similarity	NPD7157	Approved
0.7185	Intermediate Similarity	NPD6584	Phase 3
0.7179	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD9381	Approved
0.7176	Intermediate Similarity	NPD9384	Approved
0.7171	Intermediate Similarity	NPD3882	Suspended
0.7167	Intermediate Similarity	NPD1242	Phase 1
0.7164	Intermediate Similarity	NPD1283	Approved
0.7164	Intermediate Similarity	NPD5311	Approved
0.7164	Intermediate Similarity	NPD5310	Approved
0.7154	Intermediate Similarity	NPD3091	Approved
0.7154	Intermediate Similarity	NPD968	Approved
0.7143	Intermediate Similarity	NPD5314	Approved
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD6653	Approved
0.7132	Intermediate Similarity	NPD9569	Approved
0.7132	Intermediate Similarity	NPD2861	Phase 2
0.7132	Intermediate Similarity	NPD9493	Approved
0.7122	Intermediate Similarity	NPD1558	Phase 1
0.7119	Intermediate Similarity	NPD844	Approved
0.7113	Intermediate Similarity	NPD6032	Approved
0.7111	Intermediate Similarity	NPD2797	Approved
0.7111	Intermediate Similarity	NPD3094	Phase 2
0.7109	Intermediate Similarity	NPD2629	Approved
0.7101	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD9622	Approved
0.7083	Intermediate Similarity	NPD3060	Approved
0.7083	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6234	Discontinued
0.7071	Intermediate Similarity	NPD447	Suspended
0.7068	Intermediate Similarity	NPD3705	Approved
0.7063	Intermediate Similarity	NPD5763	Approved
0.7063	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5762	Approved
0.7054	Intermediate Similarity	NPD6671	Approved
0.705	Intermediate Similarity	NPD2674	Phase 3
0.7045	Intermediate Similarity	NPD1778	Approved
0.7042	Intermediate Similarity	NPD2799	Discontinued
0.7039	Intermediate Similarity	NPD2801	Approved
0.7031	Intermediate Similarity	NPD1241	Discontinued
0.7029	Intermediate Similarity	NPD5163	Phase 2
0.7027	Intermediate Similarity	NPD6273	Approved
0.7025	Intermediate Similarity	NPD3028	Approved
0.7015	Intermediate Similarity	NPD1608	Approved
0.7014	Intermediate Similarity	NPD4534	Discontinued
0.7007	Intermediate Similarity	NPD1511	Approved
0.7	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2979	Phase 3
0.6993	Remote Similarity	NPD9570	Approved
0.6993	Remote Similarity	NPD3817	Phase 2
0.6993	Remote Similarity	NPD2438	Suspended
0.6991	Remote Similarity	NPD111	Approved
0.6985	Remote Similarity	NPD1203	Approved
0.6978	Remote Similarity	NPD3268	Approved
0.6972	Remote Similarity	NPD7097	Phase 1
0.697	Remote Similarity	NPD9268	Approved
0.6966	Remote Similarity	NPD4162	Approved
0.6963	Remote Similarity	NPD2983	Phase 2
0.6963	Remote Similarity	NPD6582	Phase 2
0.6963	Remote Similarity	NPD2982	Phase 2
0.6963	Remote Similarity	NPD6583	Phase 3
0.6963	Remote Similarity	NPD4359	Approved
0.696	Remote Similarity	NPD290	Approved
0.696	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3536	Discontinued
0.6957	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4908	Phase 1
0.6957	Remote Similarity	NPD6832	Phase 2
0.695	Remote Similarity	NPD274	Approved
0.695	Remote Similarity	NPD275	Approved
0.694	Remote Similarity	NPD1281	Approved
0.6935	Remote Similarity	NPD9697	Approved
0.6934	Remote Similarity	NPD9621	Approved
0.6934	Remote Similarity	NPD9620	Approved
0.6934	Remote Similarity	NPD9619	Approved
0.6933	Remote Similarity	NPD3686	Approved
0.6933	Remote Similarity	NPD3687	Approved
0.6929	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2932	Approved
0.6917	Remote Similarity	NPD5846	Approved
0.6917	Remote Similarity	NPD3095	Discontinued
0.6917	Remote Similarity	NPD6516	Phase 2
0.6917	Remote Similarity	NPD288	Approved
0.6917	Remote Similarity	NPD3019	Approved
0.6914	Remote Similarity	NPD7685	Pre-registration
0.6913	Remote Similarity	NPD1512	Approved
0.6912	Remote Similarity	NPD3225	Approved
0.6911	Remote Similarity	NPD6647	Phase 2
0.6908	Remote Similarity	NPD6385	Approved
0.6908	Remote Similarity	NPD6386	Approved
0.6906	Remote Similarity	NPD9536	Phase 1
0.6906	Remote Similarity	NPD9537	Phase 1
0.6903	Remote Similarity	NPD7075	Discontinued
0.6897	Remote Similarity	NPD5958	Discontinued
0.6894	Remote Similarity	NPD1548	Phase 1
0.6892	Remote Similarity	NPD6799	Approved
0.6892	Remote Similarity	NPD4357	Discontinued
0.6889	Remote Similarity	NPD2981	Phase 2
0.6889	Remote Similarity	NPD2235	Phase 2
0.6889	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2231	Phase 2
0.6885	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3018	Phase 2
0.6879	Remote Similarity	NPD8127	Discontinued
0.6875	Remote Similarity	NPD3818	Discontinued
0.6875	Remote Similarity	NPD969	Suspended
0.6867	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD37	Approved
0.6861	Remote Similarity	NPD1164	Approved
0.6857	Remote Similarity	NPD3144	Approved
0.6857	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD601	Approved
0.6857	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD597	Approved
0.6857	Remote Similarity	NPD598	Approved
0.6857	Remote Similarity	NPD3145	Approved
0.6855	Remote Similarity	NPD6166	Phase 2
0.6855	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5909	Discontinued
0.6853	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7993	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