NPASS Compound

Structure

NPC27942 OpenBabel07101718332D 33 36 0 0 1 0 0 0 0 0999 V2000 -1.7321 -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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -3.4641 3.0000 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 -6.0622 0.5000 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 -0.8660 3.5000 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 -3.4641 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 -6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 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 0.8660 -2.5000 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 -1.0000 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 0.8660 1.5000 0.0000 O 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 13 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 23 1 0 0 0 0 11 31 1 0 0 0 0 12 16 2 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 25 2 0 0 0 0 14 32 1 0 0 0 0 15 16 1 0 0 0 0 15 32 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 1 0 0 0 18 20 1 0 0 0 0 18 27 1 6 0 0 0 19 22 1 0 0 0 0 19 28 1 6 0 0 0 20 21 1 1 0 0 0 20 33 1 0 0 0 0 21 29 2 0 0 0 0 21 30 1 0 0 0 0 22 31 1 1 0 0 0 22 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.1
Volume:	427.807
LogP:	1.822
LogD:	1.544
LogS:	-4.108
# Rotatable Bonds:	5
TPSA:	176.12
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.337
Synthetic Accessibility Score:	3.914
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-6.05
MDCK Permeability:	2.205755481554661e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.823
Human Intestinal Absorption (HIA):	0.287
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	88.83203887939453%
Volume Distribution (VD):	0.935
Pgp-substrate:	12.353164672851562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.385
CYP1A2-substrate:	0.3
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.764
CYP2D6-inhibitor:	0.155
CYP2D6-substrate:	0.305
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	3.879
Half-life (T1/2):	0.668

ADMET: Toxicity

hERG Blockers:	0.173
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.593
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.187
Carcinogencity:	0.16
Eye Corrosion:	0.003
Eye Irritation:	0.062
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC27942

Natural Product ID:	NPC27942
*Common Name:**	Apigenin-7-O-Beta-D-Glucuronide Methyl Ester
IUPAC Name:	methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylate
Synonyms:
Standard InCHIKey:	XXKIWCKZQFBXIR-SXFAUFNYSA-N
Standard InCHI:	InChI=1S/C22H20O11/c1-30-21(29)20-18(27)17(26)19(28)22(33-20)31-11-6-12(24)16-13(25)8-14(32-15(16)7-11)9-2-4-10(23)5-3-9/h2-8,17-20,22-24,26-28H,1H3/t17-,18-,19+,20-,22+/m0/s1
SMILES:	COC(=O)[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc(c3c(=O)cc(c4ccc(cc4)O)oc3c2)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464868
PubChem CID:	13844658
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0002934] Flavonoid O-glucuronides [CHEMONTID:0003534] Flavonoid-7-O-glucuronides

*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
NPO4380	Erigeron annuus	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[18298080]
NPO12423	Onopordum alexandrinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31199638]
NPO4380	Erigeron annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12423	Onopordum alexandrinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4380	Erigeron annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12423	Onopordum alexandrinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4380	Erigeron annuus	Species	Asteraceae	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	4

Activity Type	# Activity
Individual Protein	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	9020.0	nM	PMID[476269]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	IC50	>	50000.0	nM	PMID[476270]
NPT1799	Organism	Leishmania	Leishmania	IC50	>	50000.0	nM	PMID[476270]
NPT1235	Organism	Bacteria	Bacteria	IC50	>	50000.0	nM	PMID[476270]

☑ 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 NPC27942 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	375
0.1-0.2	1650
0.2-0.3	3912
0.3-0.4	8719
0.4-0.5	9401
0.5-0.6	4827
0.6-0.7	5664
0.7-0.8	4889
0.8-0.85	2209
0.85-0.9	603
0.9-0.95	377
0.95-1	71

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC259957
0.9935	High Similarity	NPC282169
0.9935	High Similarity	NPC48093
0.9935	High Similarity	NPC216496
0.9935	High Similarity	NPC85707
0.9935	High Similarity	NPC224530
0.9935	High Similarity	NPC129217
0.9935	High Similarity	NPC159579
0.9806	High Similarity	NPC121703
0.9804	High Similarity	NPC111929
0.9804	High Similarity	NPC104677
0.9804	High Similarity	NPC41121
0.9804	High Similarity	NPC320283
0.9804	High Similarity	NPC472459
0.9744	High Similarity	NPC72016
0.9739	High Similarity	NPC77672
0.9739	High Similarity	NPC108831
0.9739	High Similarity	NPC182634
0.9739	High Similarity	NPC54802
0.9739	High Similarity	NPC133671
0.9739	High Similarity	NPC78263
0.9739	High Similarity	NPC135391
0.9739	High Similarity	NPC197304
0.9682	High Similarity	NPC64425
0.9677	High Similarity	NPC473438
0.9677	High Similarity	NPC276377
0.9677	High Similarity	NPC476215
0.9677	High Similarity	NPC249281
0.9677	High Similarity	NPC265885
0.9677	High Similarity	NPC163242
0.9677	High Similarity	NPC246943
0.9677	High Similarity	NPC116458
0.9677	High Similarity	NPC139320
0.9677	High Similarity	NPC253788
0.9677	High Similarity	NPC181465
0.9677	High Similarity	NPC215710
0.9677	High Similarity	NPC173582
0.9673	High Similarity	NPC323593
0.9673	High Similarity	NPC203500
0.9673	High Similarity	NPC307938
0.9618	High Similarity	NPC139060
0.9618	High Similarity	NPC19240
0.9618	High Similarity	NPC205824
0.9618	High Similarity	NPC85751
0.9618	High Similarity	NPC129264
0.9615	High Similarity	NPC150164
0.9615	High Similarity	NPC240306
0.9613	High Similarity	NPC304741
0.9613	High Similarity	NPC153342
0.9613	High Similarity	NPC470405
0.9613	High Similarity	NPC471079
0.9613	High Similarity	NPC187379
0.961	High Similarity	NPC6985
0.9608	High Similarity	NPC95090
0.9608	High Similarity	NPC27408
0.9563	High Similarity	NPC175107
0.9563	High Similarity	NPC190003
0.9554	High Similarity	NPC66087
0.9554	High Similarity	NPC80068
0.9554	High Similarity	NPC278419
0.9554	High Similarity	NPC179198
0.9551	High Similarity	NPC470125
0.9551	High Similarity	NPC170052
0.9551	High Similarity	NPC135846
0.9551	High Similarity	NPC64305
0.9551	High Similarity	NPC101636
0.9551	High Similarity	NPC297987
0.9545	High Similarity	NPC127406
0.9542	High Similarity	NPC83283
0.9542	High Similarity	NPC39360
0.9542	High Similarity	NPC29763
0.9542	High Similarity	NPC143851
0.9542	High Similarity	NPC210003
0.9503	High Similarity	NPC4390
0.95	High Similarity	NPC20505
0.95	High Similarity	NPC209550
0.95	High Similarity	NPC235260
0.95	High Similarity	NPC155763
0.95	High Similarity	NPC138990
0.95	High Similarity	NPC116864
0.95	High Similarity	NPC175429
0.95	High Similarity	NPC277532
0.95	High Similarity	NPC244776
0.949	High Similarity	NPC131745
0.949	High Similarity	NPC298171
0.9487	High Similarity	NPC136761
0.9484	High Similarity	NPC44931
0.9484	High Similarity	NPC473512
0.9484	High Similarity	NPC288084
0.9484	High Similarity	NPC129827
0.9484	High Similarity	NPC43638
0.9484	High Similarity	NPC65003
0.9484	High Similarity	NPC60966
0.9444	High Similarity	NPC264735
0.9441	High Similarity	NPC221288
0.9441	High Similarity	NPC474522
0.9441	High Similarity	NPC153755
0.9441	High Similarity	NPC217822
0.9441	High Similarity	NPC11847
0.9441	High Similarity	NPC101399
0.9437	High Similarity	NPC138927
0.9434	High Similarity	NPC32641
0.9434	High Similarity	NPC221342
0.9434	High Similarity	NPC256188
0.9434	High Similarity	NPC203145
0.9434	High Similarity	NPC142142
0.9434	High Similarity	NPC12013
0.9434	High Similarity	NPC11432
0.9434	High Similarity	NPC477613
0.9434	High Similarity	NPC186816
0.9434	High Similarity	NPC189564
0.9434	High Similarity	NPC476470
0.943	High Similarity	NPC183672
0.9427	High Similarity	NPC472994
0.9427	High Similarity	NPC477629
0.9427	High Similarity	NPC195685
0.9427	High Similarity	NPC270675
0.9427	High Similarity	NPC477628
0.9427	High Similarity	NPC210961
0.9423	High Similarity	NPC43761
0.9423	High Similarity	NPC138811
0.9423	High Similarity	NPC22062
0.9423	High Similarity	NPC73511
0.9423	High Similarity	NPC473634
0.9419	High Similarity	NPC206378
0.9416	High Similarity	NPC106625
0.9387	High Similarity	NPC472385
0.9387	High Similarity	NPC198324
0.9379	High Similarity	NPC470712
0.9379	High Similarity	NPC188815
0.9379	High Similarity	NPC96605
0.9379	High Similarity	NPC218161
0.9379	High Similarity	NPC469344
0.9379	High Similarity	NPC280642
0.9379	High Similarity	NPC164704
0.9375	High Similarity	NPC317489
0.9375	High Similarity	NPC52550
0.9375	High Similarity	NPC173637
0.9375	High Similarity	NPC84362
0.9375	High Similarity	NPC127546
0.9375	High Similarity	NPC223424
0.9371	High Similarity	NPC287889
0.9371	High Similarity	NPC76831
0.9371	High Similarity	NPC135358
0.9371	High Similarity	NPC292929
0.9371	High Similarity	NPC289667
0.9367	High Similarity	NPC259834
0.9363	High Similarity	NPC473623
0.9359	High Similarity	NPC161749
0.9359	High Similarity	NPC122809
0.9359	High Similarity	NPC197896
0.9359	High Similarity	NPC313163
0.9359	High Similarity	NPC258035
0.9359	High Similarity	NPC156457
0.9355	High Similarity	NPC473241
0.9355	High Similarity	NPC26195
0.9355	High Similarity	NPC169248
0.9355	High Similarity	NPC39351
0.9355	High Similarity	NPC72649
0.9355	High Similarity	NPC97052
0.9355	High Similarity	NPC99233
0.9351	High Similarity	NPC259182
0.9351	High Similarity	NPC259767
0.9351	High Similarity	NPC88484
0.9351	High Similarity	NPC121001
0.9346	High Similarity	NPC191154
0.9329	High Similarity	NPC35167
0.9325	High Similarity	NPC237435
0.9325	High Similarity	NPC135277
0.9325	High Similarity	NPC477848
0.9325	High Similarity	NPC49344
0.9325	High Similarity	NPC101191
0.9325	High Similarity	NPC253685
0.9325	High Similarity	NPC210094
0.9325	High Similarity	NPC115760
0.9325	High Similarity	NPC43211
0.9321	High Similarity	NPC470715
0.9321	High Similarity	NPC470716
0.9321	High Similarity	NPC470714
0.9317	High Similarity	NPC5319
0.9317	High Similarity	NPC219904
0.9317	High Similarity	NPC225434
0.9317	High Similarity	NPC120099
0.9317	High Similarity	NPC223747
0.9317	High Similarity	NPC203050
0.9313	High Similarity	NPC56077
0.9313	High Similarity	NPC145038
0.9313	High Similarity	NPC253662
0.9313	High Similarity	NPC276222
0.9313	High Similarity	NPC262222
0.9313	High Similarity	NPC113968
0.9313	High Similarity	NPC68592
0.9313	High Similarity	NPC118284
0.9313	High Similarity	NPC179950
0.9313	High Similarity	NPC135599
0.9313	High Similarity	NPC88789
0.9313	High Similarity	NPC277174
0.9313	High Similarity	NPC73855
0.9313	High Similarity	NPC328940
0.9313	High Similarity	NPC274618

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 NPC27942 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	907
0.2-0.3	1824
0.3-0.4	2639
0.4-0.5	1958
0.5-0.6	996
0.6-0.7	300
0.7-0.8	131
0.8-0.85	31
0.85-0.9	18
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9359	High Similarity	NPD4381	Clinical (unspecified phase)
0.9325	High Similarity	NPD4338	Clinical (unspecified phase)
0.9317	High Similarity	NPD7804	Clinical (unspecified phase)
0.9202	High Similarity	NPD6797	Phase 2
0.9146	High Similarity	NPD7251	Discontinued
0.9091	High Similarity	NPD7808	Phase 3
0.8994	High Similarity	NPD7075	Discontinued
0.8981	High Similarity	NPD6801	Discontinued
0.8963	High Similarity	NPD7054	Approved
0.8909	High Similarity	NPD7472	Approved
0.8903	High Similarity	NPD5403	Approved
0.8831	High Similarity	NPD6799	Approved
0.8805	High Similarity	NPD7096	Clinical (unspecified phase)
0.8795	High Similarity	NPD7074	Phase 3
0.8788	High Similarity	NPD3818	Discontinued
0.8774	High Similarity	NPD5401	Approved
0.875	High Similarity	NPD3817	Phase 2
0.875	High Similarity	NPD5402	Approved
0.8734	High Similarity	NPD4380	Phase 2
0.8554	High Similarity	NPD6168	Clinical (unspecified phase)
0.8554	High Similarity	NPD6167	Clinical (unspecified phase)
0.8554	High Similarity	NPD6166	Phase 2
0.8535	High Similarity	NPD4378	Clinical (unspecified phase)
0.85	High Similarity	NPD6599	Discontinued
0.8471	Intermediate Similarity	NPD6559	Discontinued
0.8447	Intermediate Similarity	NPD7411	Suspended
0.8442	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD1934	Approved
0.8387	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD3882	Suspended
0.8354	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2801	Approved
0.825	Intermediate Similarity	NPD1512	Approved
0.8198	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD2796	Approved
0.8125	Intermediate Similarity	NPD1511	Approved
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8077	Intermediate Similarity	NPD1510	Phase 2
0.8023	Intermediate Similarity	NPD3751	Discontinued
0.8012	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3787	Discontinued
0.7967	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD8312	Approved
0.7955	Intermediate Similarity	NPD8313	Approved
0.7937	Intermediate Similarity	NPD3750	Approved
0.7935	Intermediate Similarity	NPD1240	Approved
0.7922	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD7435	Discontinued
0.787	Intermediate Similarity	NPD3749	Approved
0.7836	Intermediate Similarity	NPD6959	Discontinued
0.7834	Intermediate Similarity	NPD1607	Approved
0.7826	Intermediate Similarity	NPD4628	Phase 3
0.7818	Intermediate Similarity	NPD1653	Approved
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7768	Phase 2
0.7799	Intermediate Similarity	NPD1551	Phase 2
0.7798	Intermediate Similarity	NPD8455	Phase 2
0.7791	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD5494	Approved
0.7778	Intermediate Similarity	NPD7584	Approved
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.7764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7473	Discontinued
0.7746	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6780	Approved
0.7742	Intermediate Similarity	NPD6782	Approved
0.7742	Intermediate Similarity	NPD6776	Approved
0.7742	Intermediate Similarity	NPD6778	Approved
0.7742	Intermediate Similarity	NPD6781	Approved
0.7742	Intermediate Similarity	NPD6777	Approved
0.7742	Intermediate Similarity	NPD6779	Approved
0.774	Intermediate Similarity	NPD7685	Pre-registration
0.7701	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.7692	Intermediate Similarity	NPD6798	Discontinued
0.7658	Intermediate Similarity	NPD1933	Approved
0.7656	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD7874	Approved
0.7651	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD920	Approved
0.7643	Intermediate Similarity	NPD6233	Phase 2
0.763	Intermediate Similarity	NPD7199	Phase 2
0.7625	Intermediate Similarity	NPD7033	Discontinued
0.7625	Intermediate Similarity	NPD3748	Approved
0.7616	Intermediate Similarity	NPD919	Approved
0.7614	Intermediate Similarity	NPD7228	Approved
0.7604	Intermediate Similarity	NPD8151	Discontinued
0.7584	Intermediate Similarity	NPD5953	Discontinued
0.7571	Intermediate Similarity	NPD7286	Phase 2
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6832	Phase 2
0.7561	Intermediate Similarity	NPD6190	Approved
0.7552	Intermediate Similarity	NPD7585	Approved
0.7546	Intermediate Similarity	NPD1652	Phase 2
0.753	Intermediate Similarity	NPD2532	Approved
0.753	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2533	Approved
0.753	Intermediate Similarity	NPD2534	Approved
0.7529	Intermediate Similarity	NPD37	Approved
0.7526	Intermediate Similarity	NPD7696	Phase 3
0.7526	Intermediate Similarity	NPD7697	Approved
0.7526	Intermediate Similarity	NPD7783	Phase 2
0.7526	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7698	Approved
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD7583	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4965	Approved
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD8320	Phase 1
0.7487	Intermediate Similarity	NPD8319	Approved
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7484	Intermediate Similarity	NPD1203	Approved
0.7473	Intermediate Similarity	NPD6535	Approved
0.7473	Intermediate Similarity	NPD6534	Approved
0.7469	Intermediate Similarity	NPD2935	Discontinued
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7461	Intermediate Similarity	NPD7701	Phase 2
0.7456	Intermediate Similarity	NPD7458	Discontinued
0.7451	Intermediate Similarity	NPD1091	Approved
0.7446	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2800	Approved
0.7439	Intermediate Similarity	NPD1243	Approved
0.7438	Intermediate Similarity	NPD5124	Phase 1
0.7438	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6355	Discontinued
0.7432	Intermediate Similarity	NPD8434	Phase 2
0.7429	Intermediate Similarity	NPD1247	Approved
0.7423	Intermediate Similarity	NPD7266	Discontinued
0.741	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3268	Approved
0.7354	Intermediate Similarity	NPD7700	Phase 2
0.7354	Intermediate Similarity	NPD7699	Phase 2
0.7353	Intermediate Similarity	NPD3226	Approved
0.7347	Intermediate Similarity	NPD7801	Approved
0.7345	Intermediate Similarity	NPD3926	Phase 2
0.7338	Intermediate Similarity	NPD422	Phase 1
0.7337	Intermediate Similarity	NPD8150	Discontinued
0.7329	Intermediate Similarity	NPD230	Phase 1
0.7321	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4062	Phase 3
0.7308	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3225	Approved
0.7292	Intermediate Similarity	NPD6823	Phase 2
0.729	Intermediate Similarity	NPD9717	Approved
0.7287	Intermediate Similarity	NPD4363	Phase 3
0.7287	Intermediate Similarity	NPD4360	Phase 2
0.7284	Intermediate Similarity	NPD6651	Approved
0.7277	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2797	Approved
0.7253	Intermediate Similarity	NPD7240	Approved
0.7246	Intermediate Similarity	NPD2354	Approved
0.7246	Intermediate Similarity	NPD3887	Approved
0.7239	Intermediate Similarity	NPD7097	Phase 1
0.7233	Intermediate Similarity	NPD4908	Phase 1
0.7226	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4340	Discontinued
0.7222	Intermediate Similarity	NPD447	Suspended
0.7215	Intermediate Similarity	NPD2798	Approved
0.7212	Intermediate Similarity	NPD2346	Discontinued
0.7212	Intermediate Similarity	NPD2344	Approved
0.719	Intermediate Similarity	NPD1548	Phase 1
0.716	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6844	Discontinued
0.7117	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5711	Approved
0.7095	Intermediate Similarity	NPD5710	Approved
0.7091	Intermediate Similarity	NPD4308	Phase 3
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD9545	Approved
0.7076	Intermediate Similarity	NPD5049	Phase 3
0.7055	Intermediate Similarity	NPD4060	Phase 1
0.7053	Intermediate Similarity	NPD6213	Phase 3
0.7053	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6212	Phase 3
0.7052	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6100	Approved
0.7048	Intermediate Similarity	NPD6099	Approved
0.7045	Intermediate Similarity	NPD4288	Approved
0.7044	Intermediate Similarity	NPD3267	Approved
0.7044	Intermediate Similarity	NPD3266	Approved
0.7041	Intermediate Similarity	NPD2309	Approved
0.7019	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD2403	Approved
0.7006	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1610	Phase 2
0.7006	Intermediate Similarity	NPD2353	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