NPASS Compound

Structure

NPC472271 OpenBabel07101718302D 23 24 0 0 0 0 0 0 0 0999 V2000 -4.3301 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 -5.1962 3.0000 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 -4.3301 3.5000 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 -1.7321 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 -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 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 -5.1962 -0.0000 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 -6.0622 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -6.9282 -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 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 11 1 0 0 0 0 2 5 2 0 0 0 0 2 12 1 0 0 0 0 3 6 1 0 0 0 0 3 11 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 23 1 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.11
Volume:	319.761
LogP:	2.172
LogD:	2.615
LogS:	-2.836
# Rotatable Bonds:	7
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	2.177
Fsp3:	0.235
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:	-4.891
MDCK Permeability:	1.5826319213374518e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.955
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	93.82096099853516%
Volume Distribution (VD):	0.667
Pgp-substrate:	4.208010673522949%

ADMET: Metabolism

CYP1A2-inhibitor:	0.875
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.798
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.806
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.756
CYP2D6-substrate:	0.773
CYP3A4-inhibitor:	0.714
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	23.28
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.721
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.956
Carcinogencity:	0.376
Eye Corrosion:	0.011
Eye Irritation:	0.933
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC472271

Natural Product ID:	NPC472271
*Common Name:**	3,4-Dihydroxyphenethyl 3-(3,4-Dihydroxyphenyl)Propanoate
IUPAC Name:	2-(3,4-dihydroxyphenyl)ethyl 3-(3,4-dihydroxyphenyl)propanoate
Synonyms:
Standard InCHIKey:	GQGAKMDGSLWLHO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O6/c18-13-4-1-11(9-15(13)20)3-6-17(22)23-8-7-12-2-5-14(19)16(21)10-12/h1-2,4-5,9-10,18-21H,3,6-8H2
SMILES:	C1=CC(=C(C=C1CCC(=O)OCCC2=CC(=C(C=C2)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357165
PubChem CID:	58446617
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000139] Tyrosols 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
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	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
EC50	1
IC50	2
Others	6

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT380	Cell Line	U-251	Homo sapiens	Activity	=	55.04	%	PMID[461189]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	55.47	%	PMID[461189]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	24290.0	nM	PMID[461189]
NPT76	Cell Line	C6	Rattus norvegicus	IC50	=	6160.0	nM	PMID[461189]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	EC50	=	14900.0	nM	PMID[461190]
NPT2	Others	Unspecified		Inhibition	<	10.0	%	PMID[461190]
NPT2	Others	Unspecified		Inhibition	=	21.0	%	PMID[461190]
NPT35	Others	n.a.		Inhibition	=	37.0	%	PMID[461190]
NPT35	Others	n.a.		Inhibition	=	49.0	%	PMID[461190]

☑ 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 NPC472271 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	275
0.1-0.2	1190
0.2-0.3	3332
0.3-0.4	8930
0.4-0.5	10356
0.5-0.6	4972
0.6-0.7	10006
0.7-0.8	3343
0.8-0.85	231
0.85-0.9	45
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC85565
0.9194	High Similarity	NPC198388
0.916	High Similarity	NPC322332
0.916	High Similarity	NPC147654
0.912	High Similarity	NPC25581
0.912	High Similarity	NPC61
0.912	High Similarity	NPC5419
0.912	High Similarity	NPC18074
0.9091	High Similarity	NPC288945
0.906	High Similarity	NPC610
0.906	High Similarity	NPC175799
0.906	High Similarity	NPC200988
0.906	High Similarity	NPC145023
0.9048	High Similarity	NPC155209
0.9048	High Similarity	NPC168799
0.9043	High Similarity	NPC148969
0.9043	High Similarity	NPC264558
0.904	High Similarity	NPC318799
0.8983	High Similarity	NPC86198
0.8983	High Similarity	NPC63126
0.8976	High Similarity	NPC106406
0.8947	High Similarity	NPC222084
0.8917	High Similarity	NPC98305
0.8908	High Similarity	NPC470215
0.8908	High Similarity	NPC141791
0.8908	High Similarity	NPC109371
0.8908	High Similarity	NPC470214
0.8908	High Similarity	NPC263386
0.8908	High Similarity	NPC70084
0.8906	High Similarity	NPC123988
0.8889	High Similarity	NPC4665
0.888	High Similarity	NPC241354
0.8833	High Similarity	NPC265454
0.8833	High Similarity	NPC34634
0.8828	High Similarity	NPC248150
0.8814	High Similarity	NPC277394
0.8814	High Similarity	NPC61062
0.8814	High Similarity	NPC299252
0.8769	High Similarity	NPC310252
0.8769	High Similarity	NPC308976
0.8769	High Similarity	NPC84789
0.8769	High Similarity	NPC302583
0.8769	High Similarity	NPC100558
0.876	High Similarity	NPC470849
0.876	High Similarity	NPC470848
0.871	High Similarity	NPC280767
0.8667	High Similarity	NPC275519
0.8636	High Similarity	NPC288452
0.8636	High Similarity	NPC289690
0.8618	High Similarity	NPC86900
0.8605	High Similarity	NPC471749
0.8583	High Similarity	NPC325295
0.8583	High Similarity	NPC76308
0.8583	High Similarity	NPC94810
0.8571	High Similarity	NPC38473
0.8571	High Similarity	NPC9218
0.8548	High Similarity	NPC212541
0.8538	High Similarity	NPC68779
0.8538	High Similarity	NPC5310
0.8538	High Similarity	NPC4982
0.8538	High Similarity	NPC300776
0.8538	High Similarity	NPC176814
0.8516	High Similarity	NPC285361
0.8512	High Similarity	NPC203124
0.8512	High Similarity	NPC309434
0.8507	High Similarity	NPC253722
0.8507	High Similarity	NPC31751
0.8507	High Similarity	NPC253481
0.8504	High Similarity	NPC167463
0.8496	Intermediate Similarity	NPC179505
0.8496	Intermediate Similarity	NPC156709
0.8487	Intermediate Similarity	NPC120280
0.8473	Intermediate Similarity	NPC158325
0.8473	Intermediate Similarity	NPC103398
0.8473	Intermediate Similarity	NPC180171
0.8462	Intermediate Similarity	NPC147634
0.8462	Intermediate Similarity	NPC226401
0.8462	Intermediate Similarity	NPC120982
0.8462	Intermediate Similarity	NPC79793
0.8462	Intermediate Similarity	NPC174096
0.8448	Intermediate Similarity	NPC31274
0.8444	Intermediate Similarity	NPC285550
0.8444	Intermediate Similarity	NPC106920
0.8444	Intermediate Similarity	NPC273657
0.8438	Intermediate Similarity	NPC64111
0.8438	Intermediate Similarity	NPC226855
0.8433	Intermediate Similarity	NPC100675
0.8425	Intermediate Similarity	NPC281020
0.8421	Intermediate Similarity	NPC37250
0.8421	Intermediate Similarity	NPC152942
0.8421	Intermediate Similarity	NPC278068
0.8421	Intermediate Similarity	NPC219428
0.8421	Intermediate Similarity	NPC302857
0.8421	Intermediate Similarity	NPC142703
0.8413	Intermediate Similarity	NPC53305
0.8413	Intermediate Similarity	NPC257589
0.8409	Intermediate Similarity	NPC90431
0.839	Intermediate Similarity	NPC179002
0.839	Intermediate Similarity	NPC187583
0.839	Intermediate Similarity	NPC297657
0.839	Intermediate Similarity	NPC257430
0.8387	Intermediate Similarity	NPC194416
0.8387	Intermediate Similarity	NPC177291
0.8382	Intermediate Similarity	NPC183824
0.8382	Intermediate Similarity	NPC470130
0.8382	Intermediate Similarity	NPC160378
0.8376	Intermediate Similarity	NPC62258
0.8376	Intermediate Similarity	NPC55617
0.837	Intermediate Similarity	NPC297517
0.837	Intermediate Similarity	NPC13818
0.837	Intermediate Similarity	NPC224389
0.837	Intermediate Similarity	NPC471027
0.837	Intermediate Similarity	NPC35702
0.837	Intermediate Similarity	NPC206095
0.837	Intermediate Similarity	NPC477335
0.8359	Intermediate Similarity	NPC226661
0.8359	Intermediate Similarity	NPC79332
0.8359	Intermediate Similarity	NPC46192
0.8358	Intermediate Similarity	NPC26241
0.8358	Intermediate Similarity	NPC474875
0.8358	Intermediate Similarity	NPC205751
0.8358	Intermediate Similarity	NPC476820
0.8358	Intermediate Similarity	NPC274891
0.8358	Intermediate Similarity	NPC191280
0.8358	Intermediate Similarity	NPC476819
0.8358	Intermediate Similarity	NPC303683
0.8358	Intermediate Similarity	NPC295492
0.8347	Intermediate Similarity	NPC128249
0.8347	Intermediate Similarity	NPC281277
0.8346	Intermediate Similarity	NPC213552
0.8346	Intermediate Similarity	NPC92207
0.8346	Intermediate Similarity	NPC67349
0.8346	Intermediate Similarity	NPC90128
0.8346	Intermediate Similarity	NPC118584
0.8346	Intermediate Similarity	NPC127937
0.8346	Intermediate Similarity	NPC303680
0.8346	Intermediate Similarity	NPC279676
0.8346	Intermediate Similarity	NPC84076
0.8346	Intermediate Similarity	NPC281780
0.8346	Intermediate Similarity	NPC120225
0.8333	Intermediate Similarity	NPC471927
0.8333	Intermediate Similarity	NPC328593
0.8333	Intermediate Similarity	NPC33749
0.8333	Intermediate Similarity	NPC113295
0.8333	Intermediate Similarity	NPC261453
0.8321	Intermediate Similarity	NPC223185
0.8321	Intermediate Similarity	NPC228940
0.8319	Intermediate Similarity	NPC51698
0.8309	Intermediate Similarity	NPC43158
0.8309	Intermediate Similarity	NPC319628
0.8309	Intermediate Similarity	NPC472016
0.8309	Intermediate Similarity	NPC220664
0.8309	Intermediate Similarity	NPC192831
0.8309	Intermediate Similarity	NPC37331
0.8309	Intermediate Similarity	NPC477697
0.8309	Intermediate Similarity	NPC277315
0.8309	Intermediate Similarity	NPC470811
0.8309	Intermediate Similarity	NPC258469
0.8309	Intermediate Similarity	NPC477696
0.8309	Intermediate Similarity	NPC284948
0.8309	Intermediate Similarity	NPC303090
0.8306	Intermediate Similarity	NPC294361
0.8306	Intermediate Similarity	NPC236520
0.8296	Intermediate Similarity	NPC477279
0.8295	Intermediate Similarity	NPC208536
0.8284	Intermediate Similarity	NPC284409
0.8281	Intermediate Similarity	NPC123722
0.8281	Intermediate Similarity	NPC276466
0.8281	Intermediate Similarity	NPC151167
0.8281	Intermediate Similarity	NPC123228
0.8281	Intermediate Similarity	NPC5018
0.8281	Intermediate Similarity	NPC158654
0.8279	Intermediate Similarity	NPC278652
0.8271	Intermediate Similarity	NPC156892
0.8268	Intermediate Similarity	NPC197832
0.8268	Intermediate Similarity	NPC3221
0.8268	Intermediate Similarity	NPC289459
0.8268	Intermediate Similarity	NPC67951
0.8264	Intermediate Similarity	NPC474967
0.8264	Intermediate Similarity	NPC233669
0.8261	Intermediate Similarity	NPC471511
0.8261	Intermediate Similarity	NPC12278
0.8258	Intermediate Similarity	NPC287597
0.8258	Intermediate Similarity	NPC34293
0.8258	Intermediate Similarity	NPC67247
0.8258	Intermediate Similarity	NPC886
0.8258	Intermediate Similarity	NPC135127
0.8254	Intermediate Similarity	NPC473451
0.8254	Intermediate Similarity	NPC285345
0.8254	Intermediate Similarity	NPC306100
0.825	Intermediate Similarity	NPC471485
0.825	Intermediate Similarity	NPC95381
0.8235	Intermediate Similarity	NPC477277
0.8235	Intermediate Similarity	NPC477278
0.8231	Intermediate Similarity	NPC275724
0.8231	Intermediate Similarity	NPC215941
0.8231	Intermediate Similarity	NPC123196
0.8231	Intermediate Similarity	NPC244246
0.8231	Intermediate Similarity	NPC311419
0.8231	Intermediate Similarity	NPC137427

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 NPC472271 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	795
0.2-0.3	1501
0.3-0.4	2758
0.4-0.5	1940
0.5-0.6	1236
0.6-0.7	574
0.7-0.8	102
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8309	Intermediate Similarity	NPD6190	Approved
0.822	Intermediate Similarity	NPD3021	Approved
0.822	Intermediate Similarity	NPD3022	Approved
0.8106	Intermediate Similarity	NPD826	Approved
0.8106	Intermediate Similarity	NPD825	Approved
0.8045	Intermediate Similarity	NPD230	Phase 1
0.8015	Intermediate Similarity	NPD7266	Discontinued
0.7971	Intermediate Similarity	NPD8166	Discontinued
0.791	Intermediate Similarity	NPD555	Phase 2
0.7829	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD257	Approved
0.7786	Intermediate Similarity	NPD258	Approved
0.7778	Intermediate Similarity	NPD9545	Approved
0.7761	Intermediate Similarity	NPD259	Phase 1
0.7752	Intermediate Similarity	NPD9269	Phase 2
0.7744	Intermediate Similarity	NPD3027	Phase 3
0.7727	Intermediate Similarity	NPD9569	Approved
0.7704	Intermediate Similarity	NPD943	Approved
0.7687	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD3764	Approved
0.7681	Intermediate Similarity	NPD9570	Approved
0.7655	Intermediate Similarity	NPD3455	Phase 2
0.7638	Intermediate Similarity	NPD1894	Discontinued
0.763	Intermediate Similarity	NPD6663	Approved
0.7615	Intermediate Similarity	NPD1608	Approved
0.7594	Intermediate Similarity	NPD5736	Approved
0.7589	Intermediate Similarity	NPD4628	Phase 3
0.7584	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD2934	Approved
0.7565	Intermediate Similarity	NPD2933	Approved
0.7556	Intermediate Similarity	NPD6798	Discontinued
0.7538	Intermediate Similarity	NPD1535	Discovery
0.7518	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD2859	Approved
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD2860	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD4062	Phase 3
0.7483	Intermediate Similarity	NPD6234	Discontinued
0.7481	Intermediate Similarity	NPD9537	Phase 1
0.7481	Intermediate Similarity	NPD9536	Phase 1
0.7481	Intermediate Similarity	NPD1481	Phase 2
0.7465	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4110	Phase 3
0.746	Intermediate Similarity	NPD2629	Approved
0.7459	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD3020	Approved
0.745	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4060	Phase 1
0.7445	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD1613	Approved
0.7442	Intermediate Similarity	NPD9268	Approved
0.7431	Intermediate Similarity	NPD1511	Approved
0.7407	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD1242	Phase 1
0.7391	Intermediate Similarity	NPD274	Approved
0.7391	Intermediate Similarity	NPD275	Approved
0.7385	Intermediate Similarity	NPD3019	Approved
0.7385	Intermediate Similarity	NPD2932	Approved
0.7385	Intermediate Similarity	NPD17	Approved
0.7383	Intermediate Similarity	NPD1934	Approved
0.7368	Intermediate Similarity	NPD1283	Approved
0.7353	Intermediate Similarity	NPD7095	Approved
0.7351	Intermediate Similarity	NPD3882	Suspended
0.7333	Intermediate Similarity	NPD9494	Approved
0.7333	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2801	Approved
0.7329	Intermediate Similarity	NPD1512	Approved
0.7328	Intermediate Similarity	NPD3847	Discontinued
0.7319	Intermediate Similarity	NPD3061	Approved
0.7319	Intermediate Similarity	NPD3059	Approved
0.7319	Intermediate Similarity	NPD3062	Approved
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7287	Intermediate Similarity	NPD5536	Phase 2
0.7285	Intermediate Similarity	NPD3817	Phase 2
0.728	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD37	Approved
0.726	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9384	Approved
0.7252	Intermediate Similarity	NPD1778	Approved
0.7252	Intermediate Similarity	NPD9381	Approved
0.7244	Intermediate Similarity	NPD5283	Phase 1
0.7237	Intermediate Similarity	NPD4967	Phase 2
0.7237	Intermediate Similarity	NPD4966	Approved
0.7237	Intermediate Similarity	NPD4965	Approved
0.7227	Intermediate Similarity	NPD9495	Approved
0.7214	Intermediate Similarity	NPD5314	Approved
0.7194	Intermediate Similarity	NPD2979	Phase 3
0.7183	Intermediate Similarity	NPD5408	Approved
0.7183	Intermediate Similarity	NPD5404	Approved
0.7183	Intermediate Similarity	NPD5406	Approved
0.7183	Intermediate Similarity	NPD5405	Approved
0.7176	Intermediate Similarity	NPD5585	Approved
0.7165	Intermediate Similarity	NPD9379	Approved
0.7165	Intermediate Similarity	NPD9377	Approved
0.7161	Intermediate Similarity	NPD7199	Phase 2
0.7154	Intermediate Similarity	NPD5048	Discontinued
0.7153	Intermediate Similarity	NPD2614	Approved
0.7152	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD4340	Discontinued
0.7132	Intermediate Similarity	NPD256	Approved
0.7132	Intermediate Similarity	NPD255	Approved
0.7113	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7033	Discontinued
0.7111	Intermediate Similarity	NPD5311	Approved
0.7111	Intermediate Similarity	NPD5310	Approved
0.7103	Intermediate Similarity	NPD3400	Discontinued
0.7103	Intermediate Similarity	NPD3750	Approved
0.7086	Intermediate Similarity	NPD6386	Approved
0.7086	Intermediate Similarity	NPD6385	Approved
0.7083	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5958	Discontinued
0.7083	Intermediate Similarity	NPD4534	Discontinued
0.708	Intermediate Similarity	NPD2861	Phase 2
0.7077	Intermediate Similarity	NPD9568	Approved
0.7075	Intermediate Similarity	NPD6799	Approved
0.7071	Intermediate Similarity	NPD1558	Phase 1
0.707	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1551	Phase 2
0.7063	Intermediate Similarity	NPD2438	Suspended
0.7059	Intermediate Similarity	NPD3053	Approved
0.7059	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD1470	Approved
0.7059	Intermediate Similarity	NPD1164	Approved
0.7059	Intermediate Similarity	NPD3055	Approved
0.7047	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1651	Approved
0.7044	Intermediate Similarity	NPD3818	Discontinued
0.7042	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD9622	Approved
0.7031	Intermediate Similarity	NPD5535	Approved
0.7027	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3146	Approved
0.7025	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6166	Phase 2
0.7025	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3705	Approved
0.7015	Intermediate Similarity	NPD3092	Approved
0.7006	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD7054	Approved
0.7	Intermediate Similarity	NPD1653	Approved
0.6993	Remote Similarity	NPD1510	Phase 2
0.6993	Remote Similarity	NPD1465	Phase 2
0.6985	Remote Similarity	NPD3225	Approved
0.6975	Remote Similarity	NPD7685	Pre-registration
0.6975	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6653	Approved
0.697	Remote Similarity	NPD1759	Phase 1
0.697	Remote Similarity	NPD1548	Phase 1
0.6968	Remote Similarity	NPD7075	Discontinued
0.6957	Remote Similarity	NPD7472	Approved
0.6957	Remote Similarity	NPD7074	Phase 3
0.6947	Remote Similarity	NPD9493	Approved
0.6944	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2531	Phase 2
0.6944	Remote Similarity	NPD4476	Approved
0.6944	Remote Similarity	NPD4477	Approved
0.694	Remote Similarity	NPD4136	Approved
0.694	Remote Similarity	NPD4135	Approved
0.694	Remote Similarity	NPD3026	Approved
0.694	Remote Similarity	NPD3023	Approved
0.694	Remote Similarity	NPD3496	Discontinued
0.694	Remote Similarity	NPD4106	Approved
0.6934	Remote Similarity	NPD3094	Phase 2
0.6934	Remote Similarity	NPD1203	Approved
0.6929	Remote Similarity	NPD3268	Approved
0.6918	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD844	Approved
0.6917	Remote Similarity	NPD3025	Approved
0.6917	Remote Similarity	NPD3024	Approved
0.6914	Remote Similarity	NPD6797	Phase 2
0.6912	Remote Similarity	NPD2983	Phase 2
0.6912	Remote Similarity	NPD2982	Phase 2
0.6912	Remote Similarity	NPD4359	Approved
0.6911	Remote Similarity	NPD940	Approved
0.6911	Remote Similarity	NPD846	Approved
0.6909	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4380	Phase 2
0.6906	Remote Similarity	NPD4908	Phase 1
0.6905	Remote Similarity	NPD1358	Approved
0.6901	Remote Similarity	NPD447	Suspended
0.6897	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1758	Phase 1
0.6894	Remote Similarity	NPD5844	Phase 1
0.6889	Remote Similarity	NPD422	Phase 1
0.6889	Remote Similarity	NPD1610	Phase 2
0.6887	Remote Similarity	NPD3687	Approved
0.6887	Remote Similarity	NPD3686	Approved
0.6885	Remote Similarity	NPD7798	Approved
0.6884	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9619	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