NPASS Compound

Structure

NPC1913 OpenBabel07101719242D 35 37 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 -1.5000 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 1.7321 -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 -1.7321 0.0000 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 0.8660 -2.5000 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 -4.3301 -2.5000 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 1.7321 -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 2 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -3.4641 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 2 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 7 2 0 0 0 0 2 9 1 0 0 0 0 3 7 1 0 0 0 0 3 10 2 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 33 1 0 0 0 0 7 20 1 0 0 0 0 8 19 1 0 0 0 0 9 14 2 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 10 23 1 0 0 0 0 11 15 2 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 34 1 0 0 0 0 13 6 1 6 0 0 0 13 16 1 0 0 0 0 13 35 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 1 0 0 0 17 18 1 0 0 0 0 17 28 1 6 0 0 0 18 21 1 0 0 0 0 18 29 1 1 0 0 0 19 30 2 0 0 0 0 19 32 1 0 0 0 0 20 31 2 0 0 0 0 20 33 1 0 0 0 0 21 34 1 6 0 0 0 21 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.1
Volume:	448.074
LogP:	0.623
LogD:	0.369
LogS:	-2.496
# Rotatable Bonds:	8
TPSA:	232.9
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.177
Synthetic Accessibility Score:	3.976
Fsp3:	0.333
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.677
MDCK Permeability:	2.666651562321931e-05
Pgp-inhibitor:	0.05
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.88
20% Bioavailability (F20%):	0.29
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	90.50621795654297%
Volume Distribution (VD):	0.466
Pgp-substrate:	14.151597023010254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.167
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.147
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	7.735
Half-life (T1/2):	0.971

ADMET: Toxicity

hERG Blockers:	0.339
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.946
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.88
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC1913

Natural Product ID:	NPC1913
*Common Name:**	Methyl Gallate 3-O-Beta-D-(6'-O-Galloyl)-Glucopyranoside
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-(2,3-dihydroxy-5-methoxycarbonylphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	VIUNGBRQZJFLQR-GUFUGUNKSA-N
Standard InCHI:	InChI=1S/C21H22O14/c1-32-19(30)8-4-11(24)15(26)12(5-8)34-21-18(29)17(28)16(27)13(35-21)6-33-20(31)7-2-9(22)14(25)10(23)3-7/h2-5,13,16-18,21-29H,6H2,1H3/t13-,16-,17+,18-,21-/m1/s1
SMILES:	COC(=O)c1cc(O[C@@H]2O[C@H](COC(=O)c3cc(O)c(c(c3)O)O)[C@H]([C@@H]([C@H]2O)O)O)c(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485256
PubChem CID:	10097402
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	stems	n.a.	n.a.	PMID[12350169]
NPO12848	Carpinus cordata	Species	Betulaceae	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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	4.9	ug.mL-1	PMID[548215]

☑ 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 NPC1913 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	348
0.1-0.2	1572
0.2-0.3	3942
0.3-0.4	8738
0.4-0.5	9342
0.5-0.6	4181
0.6-0.7	5310
0.7-0.8	6743
0.8-0.85	1866
0.85-0.9	545
0.9-0.95	83
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC289811
0.9933	High Similarity	NPC160780
0.9868	High Similarity	NPC203020
0.9868	High Similarity	NPC166277
0.9868	High Similarity	NPC119125
0.9868	High Similarity	NPC239966
0.9803	High Similarity	NPC472859
0.9803	High Similarity	NPC25389
0.9803	High Similarity	NPC311803
0.9739	High Similarity	NPC33298
0.9739	High Similarity	NPC285108
0.9735	High Similarity	NPC472860
0.9732	High Similarity	NPC310661
0.9732	High Similarity	NPC105827
0.9671	High Similarity	NPC74319
0.9671	High Similarity	NPC287872
0.9667	High Similarity	NPC327032
0.9667	High Similarity	NPC194095
0.9667	High Similarity	NPC191046
0.9608	High Similarity	NPC289346
0.9539	High Similarity	NPC471405
0.9533	High Similarity	NPC134905
0.9533	High Similarity	NPC36130
0.949	High Similarity	NPC116745
0.9484	High Similarity	NPC90905
0.9484	High Similarity	NPC4013
0.9484	High Similarity	NPC41009
0.9477	High Similarity	NPC133984
0.9474	High Similarity	NPC10205
0.9463	High Similarity	NPC92117
0.943	High Similarity	NPC658
0.943	High Similarity	NPC197708
0.9404	High Similarity	NPC75695
0.9396	High Similarity	NPC120621
0.9396	High Similarity	NPC248257
0.9359	High Similarity	NPC148273
0.9342	High Similarity	NPC157898
0.9342	High Similarity	NPC137813
0.9338	High Similarity	NPC140151
0.9333	High Similarity	NPC111785
0.9313	High Similarity	NPC5786
0.9313	High Similarity	NPC102851
0.9299	High Similarity	NPC88043
0.9272	High Similarity	NPC473091
0.9255	High Similarity	NPC172033
0.9255	High Similarity	NPC175230
0.9255	High Similarity	NPC163165
0.9255	High Similarity	NPC88560
0.925	High Similarity	NPC149011
0.925	High Similarity	NPC204937
0.9241	High Similarity	NPC165720
0.9226	High Similarity	NPC226759
0.9216	High Similarity	NPC44260
0.9216	High Similarity	NPC205037
0.9216	High Similarity	NPC61152
0.9216	High Similarity	NPC3746
0.9216	High Similarity	NPC16024
0.9205	High Similarity	NPC476394
0.9205	High Similarity	NPC98809
0.9198	High Similarity	NPC169645
0.9198	High Similarity	NPC84482
0.9195	High Similarity	NPC108455
0.9193	High Similarity	NPC172807
0.9193	High Similarity	NPC211594
0.9193	High Similarity	NPC254540
0.9187	High Similarity	NPC229687
0.9187	High Similarity	NPC149300
0.9187	High Similarity	NPC198125
0.9187	High Similarity	NPC95421
0.9177	High Similarity	NPC284960
0.9177	High Similarity	NPC222936
0.9172	High Similarity	NPC217950
0.9167	High Similarity	NPC87317
0.9145	High Similarity	NPC205054
0.9141	High Similarity	NPC67629
0.9141	High Similarity	NPC79736
0.9139	High Similarity	NPC472969
0.9136	High Similarity	NPC46640
0.9136	High Similarity	NPC472993
0.9136	High Similarity	NPC263119
0.9136	High Similarity	NPC34436
0.9136	High Similarity	NPC4390
0.9136	High Similarity	NPC166674
0.9136	High Similarity	NPC219600
0.913	High Similarity	NPC212748
0.913	High Similarity	NPC224462
0.9128	High Similarity	NPC226738
0.9128	High Similarity	NPC229036
0.9128	High Similarity	NPC121573
0.9128	High Similarity	NPC22176
0.9128	High Similarity	NPC190587
0.9125	High Similarity	NPC45400
0.9125	High Similarity	NPC229729
0.9119	High Similarity	NPC311830
0.9119	High Similarity	NPC475738
0.9119	High Similarity	NPC22832
0.9114	High Similarity	NPC127782
0.9114	High Similarity	NPC300537
0.9114	High Similarity	NPC473043
0.9108	High Similarity	NPC53889
0.9097	High Similarity	NPC145425
0.9085	High Similarity	NPC267549
0.908	High Similarity	NPC477848
0.9079	High Similarity	NPC75945
0.9079	High Similarity	NPC106138
0.9074	High Similarity	NPC472386
0.9074	High Similarity	NPC205076
0.9074	High Similarity	NPC190003
0.9074	High Similarity	NPC307518
0.9074	High Similarity	NPC175107
0.9074	High Similarity	NPC48773
0.9074	High Similarity	NPC153755
0.9068	High Similarity	NPC45638
0.9068	High Similarity	NPC105025
0.9068	High Similarity	NPC93337
0.9068	High Similarity	NPC469931
0.9068	High Similarity	NPC475942
0.9068	High Similarity	NPC183036
0.9068	High Similarity	NPC58053
0.9068	High Similarity	NPC186807
0.9068	High Similarity	NPC201292
0.9068	High Similarity	NPC226294
0.9068	High Similarity	NPC138927
0.9062	High Similarity	NPC5778
0.9062	High Similarity	NPC236934
0.9057	High Similarity	NPC191306
0.9057	High Similarity	NPC19709
0.9057	High Similarity	NPC270335
0.9057	High Similarity	NPC168822
0.9057	High Similarity	NPC88023
0.9057	High Similarity	NPC309025
0.9057	High Similarity	NPC94777
0.9057	High Similarity	NPC243930
0.9057	High Similarity	NPC121290
0.9038	High Similarity	NPC291948
0.9038	High Similarity	NPC88803
0.9038	High Similarity	NPC250436
0.9038	High Similarity	NPC104983
0.9038	High Similarity	NPC300845
0.9024	High Similarity	NPC472385
0.9024	High Similarity	NPC198324
0.9024	High Similarity	NPC472991
0.9024	High Similarity	NPC473713
0.9024	High Similarity	NPC211532
0.9024	High Similarity	NPC472992
0.9024	High Similarity	NPC297574
0.9024	High Similarity	NPC233994
0.9018	High Similarity	NPC473550
0.9013	High Similarity	NPC478237
0.9012	High Similarity	NPC72249
0.9012	High Similarity	NPC206123
0.9012	High Similarity	NPC44558
0.9012	High Similarity	NPC20505
0.9012	High Similarity	NPC231194
0.9012	High Similarity	NPC116864
0.9012	High Similarity	NPC22195
0.9012	High Similarity	NPC471416
0.9012	High Similarity	NPC51326
0.9012	High Similarity	NPC181778
0.9012	High Similarity	NPC155763
0.9012	High Similarity	NPC183357
0.9012	High Similarity	NPC34287
0.9012	High Similarity	NPC105511
0.9012	High Similarity	NPC21190
0.9012	High Similarity	NPC235260
0.9012	High Similarity	NPC244776
0.9012	High Similarity	NPC474434
0.9006	High Similarity	NPC226304
0.9006	High Similarity	NPC58716
0.9006	High Similarity	NPC265530
0.9006	High Similarity	NPC325555
0.9006	High Similarity	NPC45618
0.9006	High Similarity	NPC477502
0.9006	High Similarity	NPC473818
0.9006	High Similarity	NPC146792
0.9	High Similarity	NPC134975
0.8994	High Similarity	NPC77660
0.8994	High Similarity	NPC189142
0.8987	High Similarity	NPC476373
0.8987	High Similarity	NPC24164
0.8987	High Similarity	NPC110349
0.8987	High Similarity	NPC24627
0.8981	High Similarity	NPC38779
0.8981	High Similarity	NPC160512
0.8981	High Similarity	NPC156818
0.8981	High Similarity	NPC68324
0.8981	High Similarity	NPC289322
0.8981	High Similarity	NPC172419
0.8981	High Similarity	NPC238419
0.8981	High Similarity	NPC114179
0.8974	High Similarity	NPC172920
0.8974	High Similarity	NPC156624
0.897	High Similarity	NPC258044
0.897	High Similarity	NPC267680
0.897	High Similarity	NPC217387
0.897	High Similarity	NPC293626
0.897	High Similarity	NPC217520
0.897	High Similarity	NPC476621
0.897	High Similarity	NPC196127
0.897	High Similarity	NPC472387

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 NPC1913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	898
0.2-0.3	1934
0.3-0.4	2609
0.4-0.5	1874
0.5-0.6	948
0.6-0.7	433
0.7-0.8	122
0.8-0.85	25
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9038	High Similarity	NPD4868	Clinical (unspecified phase)
0.9006	High Similarity	NPD3818	Discontinued
0.8963	High Similarity	NPD4338	Clinical (unspecified phase)
0.8951	High Similarity	NPD7054	Approved
0.8896	High Similarity	NPD7472	Approved
0.8896	High Similarity	NPD7074	Phase 3
0.8727	High Similarity	NPD6797	Phase 2
0.8675	High Similarity	NPD7251	Discontinued
0.8625	High Similarity	NPD4381	Clinical (unspecified phase)
0.8623	High Similarity	NPD7808	Phase 3
0.8608	High Similarity	NPD1934	Approved
0.859	High Similarity	NPD1653	Approved
0.8563	High Similarity	NPD7685	Pre-registration
0.8503	High Similarity	NPD7993	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD230	Phase 1
0.8438	Intermediate Similarity	NPD2801	Approved
0.8438	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD1465	Phase 2
0.8424	Intermediate Similarity	NPD6166	Phase 2
0.8424	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD3817	Phase 2
0.8344	Intermediate Similarity	NPD6234	Discontinued
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8323	Intermediate Similarity	NPD7228	Approved
0.8274	Intermediate Similarity	NPD5844	Phase 1
0.8261	Intermediate Similarity	NPD37	Approved
0.8235	Intermediate Similarity	NPD6559	Discontinued
0.8221	Intermediate Similarity	NPD4966	Approved
0.8221	Intermediate Similarity	NPD4965	Approved
0.8221	Intermediate Similarity	NPD4967	Phase 2
0.8205	Intermediate Similarity	NPD6190	Approved
0.8182	Intermediate Similarity	NPD7266	Discontinued
0.8171	Intermediate Similarity	NPD7075	Discontinued
0.8166	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7199	Phase 2
0.8101	Intermediate Similarity	NPD1511	Approved
0.8101	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.8025	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD1512	Approved
0.7988	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6232	Discontinued
0.7943	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5402	Approved
0.7929	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6801	Discontinued
0.7879	Intermediate Similarity	NPD7819	Suspended
0.7875	Intermediate Similarity	NPD6799	Approved
0.7857	Intermediate Similarity	NPD5494	Approved
0.7836	Intermediate Similarity	NPD7473	Discontinued
0.7831	Intermediate Similarity	NPD5353	Approved
0.7829	Intermediate Similarity	NPD3027	Phase 3
0.7816	Intermediate Similarity	NPD7240	Approved
0.7792	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1613	Approved
0.7785	Intermediate Similarity	NPD1549	Phase 2
0.7758	Intermediate Similarity	NPD7411	Suspended
0.7742	Intermediate Similarity	NPD1933	Approved
0.773	Intermediate Similarity	NPD5403	Approved
0.7722	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD9269	Phase 2
0.7697	Intermediate Similarity	NPD9494	Approved
0.7662	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD447	Suspended
0.7627	Intermediate Similarity	NPD8312	Approved
0.7627	Intermediate Similarity	NPD8313	Approved
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5401	Approved
0.7607	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6599	Discontinued
0.7586	Intermediate Similarity	NPD3751	Discontinued
0.7582	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3750	Approved
0.7562	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD8455	Phase 2
0.7547	Intermediate Similarity	NPD2796	Approved
0.7547	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5242	Approved
0.75	Intermediate Similarity	NPD6959	Discontinued
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7484	Intermediate Similarity	NPD1510	Phase 2
0.7473	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3787	Discontinued
0.745	Intermediate Similarity	NPD9268	Approved
0.744	Intermediate Similarity	NPD6386	Approved
0.744	Intermediate Similarity	NPD6385	Approved
0.7434	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2533	Approved
0.7394	Intermediate Similarity	NPD2532	Approved
0.7394	Intermediate Similarity	NPD2534	Approved
0.7389	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD919	Approved
0.7368	Intermediate Similarity	NPD7768	Phase 2
0.7362	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7585	Approved
0.7342	Intermediate Similarity	NPD1240	Approved
0.7342	Intermediate Similarity	NPD943	Approved
0.7329	Intermediate Similarity	NPD2935	Discontinued
0.7326	Intermediate Similarity	NPD3749	Approved
0.7318	Intermediate Similarity	NPD7038	Approved
0.7318	Intermediate Similarity	NPD7039	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7316	Intermediate Similarity	NPD7680	Approved
0.7314	Intermediate Similarity	NPD3926	Phase 2
0.7303	Intermediate Similarity	NPD1091	Approved
0.7292	Intermediate Similarity	NPD7583	Approved
0.7289	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD9545	Approved
0.7267	Intermediate Similarity	NPD3748	Approved
0.725	Intermediate Similarity	NPD1607	Approved
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7213	Intermediate Similarity	NPD8434	Phase 2
0.7202	Intermediate Similarity	NPD7584	Approved
0.72	Intermediate Similarity	NPD8127	Discontinued
0.72	Intermediate Similarity	NPD1247	Approved
0.7195	Intermediate Similarity	NPD1652	Phase 2
0.7195	Intermediate Similarity	NPD6674	Discontinued
0.7167	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD1608	Approved
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4357	Discontinued
0.7118	Intermediate Similarity	NPD3455	Phase 2
0.7118	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3226	Approved
0.7117	Intermediate Similarity	NPD6100	Approved
0.7117	Intermediate Similarity	NPD6099	Approved
0.7115	Intermediate Similarity	NPD1203	Approved
0.7107	Intermediate Similarity	NPD6798	Discontinued
0.7101	Intermediate Similarity	NPD920	Approved
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6832	Phase 2
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7286	Phase 2
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7048	Intermediate Similarity	NPD4110	Phase 3
0.7048	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7696	Phase 3
0.7047	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD7697	Approved
0.7041	Intermediate Similarity	NPD6273	Approved
0.7029	Intermediate Similarity	NPD6971	Discontinued
0.701	Intermediate Similarity	NPD7870	Phase 2
0.701	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3764	Approved
0.6995	Remote Similarity	NPD6823	Phase 2
0.6994	Remote Similarity	NPD7097	Phase 1
0.699	Remote Similarity	NPD7701	Phase 2
0.6989	Remote Similarity	NPD6842	Approved
0.6989	Remote Similarity	NPD6843	Phase 3
0.6989	Remote Similarity	NPD6841	Approved
0.6988	Remote Similarity	NPD2800	Approved
0.6988	Remote Similarity	NPD1243	Approved
0.6987	Remote Similarity	NPD2983	Phase 2
0.6987	Remote Similarity	NPD2982	Phase 2
0.6984	Remote Similarity	NPD6535	Approved
0.6984	Remote Similarity	NPD6534	Approved
0.6982	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4908	Phase 1
0.6975	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5124	Phase 1
0.6975	Remote Similarity	NPD6355	Discontinued
0.6974	Remote Similarity	NPD5536	Phase 2
0.697	Remote Similarity	NPD2346	Discontinued
0.6968	Remote Similarity	NPD422	Phase 1
0.6968	Remote Similarity	NPD3705	Approved
0.6966	Remote Similarity	NPD5710	Approved
0.6966	Remote Similarity	NPD7229	Phase 3
0.6966	Remote Similarity	NPD5711	Approved
0.6957	Remote Similarity	NPD4062	Phase 3
0.6951	Remote Similarity	NPD2799	Discontinued
0.6951	Remote Similarity	NPD4308	Phase 3
0.6951	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD17	Approved
0.6943	Remote Similarity	NPD3225	Approved
0.6935	Remote Similarity	NPD8150	Discontinued
0.6923	Remote Similarity	NPD2981	Phase 2
0.6923	Remote Similarity	NPD8319	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