NPASS Compound

Structure

NPC471590 OpenBabel07101719512D 26 28 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 -6.0622 -3.5000 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 4.3301 -0.5000 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 -5.1962 -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 2.5981 -1.5000 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 -2.5981 -3.5000 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 1.7321 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 -3.4641 -3.0000 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 -3.4641 -2.0000 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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 15 23 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 21 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 21 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	368.962
LogP:	4.168
LogD:	4.015
LogS:	-5.726
# Rotatable Bonds:	7
TPSA:	57.9
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	2.114
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.801
MDCK Permeability:	3.881731390720233e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.394

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	99.12947845458984%
Volume Distribution (VD):	0.913
Pgp-substrate:	1.75153648853302%

ADMET: Metabolism

CYP1A2-inhibitor:	0.589
CYP1A2-substrate:	0.672
CYP2C19-inhibitor:	0.667
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.85
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.192
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.277
CYP3A4-substrate:	0.448

ADMET: Excretion

Clearance (CL):	2.233
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.164
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.881
AMES Toxicity:	0.244
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.062
Skin Sensitization:	0.058
Carcinogencity:	0.512
Eye Corrosion:	0.003
Eye Irritation:	0.486
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC471590

Natural Product ID:	NPC471590
*Common Name:**	3-(3,4-Diethoxyphenyl)-7-Ethoxychromen-4-One
IUPAC Name:	3-(3,4-diethoxyphenyl)-7-ethoxychromen-4-one
Synonyms:
Standard InCHIKey:	CYGZSNBBBWDCLM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-4-23-15-8-9-16-19(12-15)26-13-17(21(16)22)14-7-10-18(24-5-2)20(11-14)25-6-3/h7-13H,4-6H2,1-3H3
SMILES:	CCOc1ccc2c(c1)occ(c2=O)c1ccc(c(c1)OCC)OCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL268502
PubChem CID:	12016832
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*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
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(79)80020-5]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[10328294]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	18.0	ug.mL-1	PMID[538256]

☑ 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 NPC471590 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	500
0.1-0.2	1884
0.2-0.3	4818
0.3-0.4	11919
0.4-0.5	5710
0.5-0.6	3934
0.6-0.7	5549
0.7-0.8	4952
0.8-0.85	2218
0.85-0.9	1027
0.9-0.95	164
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9784	High Similarity	NPC293201
0.9784	High Similarity	NPC113089
0.9783	High Similarity	NPC185607
0.9716	High Similarity	NPC470511
0.9714	High Similarity	NPC136278
0.9712	High Similarity	NPC9966
0.9712	High Similarity	NPC70853
0.965	High Similarity	NPC5840
0.965	High Similarity	NPC189270
0.964	High Similarity	NPC29536
0.9577	High Similarity	NPC299923
0.9577	High Similarity	NPC205522
0.9571	High Similarity	NPC476054
0.9517	High Similarity	NPC68882
0.9517	High Similarity	NPC40033
0.951	High Similarity	NPC476342
0.951	High Similarity	NPC63256
0.951	High Similarity	NPC10304
0.9507	High Similarity	NPC195919
0.9507	High Similarity	NPC14958
0.9507	High Similarity	NPC215932
0.9507	High Similarity	NPC120924
0.9507	High Similarity	NPC110639
0.9507	High Similarity	NPC40818
0.9507	High Similarity	NPC106461
0.9507	High Similarity	NPC216314
0.9507	High Similarity	NPC310259
0.9493	High Similarity	NPC44573
0.9452	High Similarity	NPC186507
0.9444	High Similarity	NPC238366
0.9441	High Similarity	NPC85233
0.9441	High Similarity	NPC474999
0.942	High Similarity	NPC254741
0.9375	High Similarity	NPC195202
0.9375	High Similarity	NPC261548
0.9371	High Similarity	NPC283002
0.9371	High Similarity	NPC231013
0.9371	High Similarity	NPC302408
0.9371	High Similarity	NPC12377
0.9366	High Similarity	NPC182842
0.9366	High Similarity	NPC23955
0.9324	High Similarity	NPC474983
0.932	High Similarity	NPC472408
0.932	High Similarity	NPC128961
0.932	High Similarity	NPC280937
0.9315	High Similarity	NPC308451
0.931	High Similarity	NPC474648
0.931	High Similarity	NPC69752
0.9306	High Similarity	NPC33265
0.9306	High Similarity	NPC62536
0.9306	High Similarity	NPC117463
0.9306	High Similarity	NPC12200
0.9301	High Similarity	NPC165512
0.9262	High Similarity	NPC78071
0.9262	High Similarity	NPC19097
0.9257	High Similarity	NPC31018
0.9257	High Similarity	NPC234255
0.9257	High Similarity	NPC255807
0.9252	High Similarity	NPC477231
0.9252	High Similarity	NPC39732
0.9252	High Similarity	NPC166201
0.9252	High Similarity	NPC472912
0.9252	High Similarity	NPC257648
0.9252	High Similarity	NPC60972
0.9247	High Similarity	NPC166753
0.9247	High Similarity	NPC259058
0.9247	High Similarity	NPC50728
0.9247	High Similarity	NPC201547
0.9247	High Similarity	NPC338131
0.9241	High Similarity	NPC203747
0.9241	High Similarity	NPC80710
0.9241	High Similarity	NPC183236
0.9241	High Similarity	NPC254702
0.9241	High Similarity	NPC194653
0.9241	High Similarity	NPC139364
0.9225	High Similarity	NPC124467
0.9225	High Similarity	NPC214919
0.9209	High Similarity	NPC77955
0.9203	High Similarity	NPC223354
0.9203	High Similarity	NPC292998
0.92	High Similarity	NPC184755
0.92	High Similarity	NPC74178
0.92	High Similarity	NPC113055
0.92	High Similarity	NPC187792
0.9195	High Similarity	NPC180340
0.9195	High Similarity	NPC472455
0.9189	High Similarity	NPC472915
0.9189	High Similarity	NPC18727
0.9189	High Similarity	NPC469550
0.9184	High Similarity	NPC262623
0.9184	High Similarity	NPC236769
0.9184	High Similarity	NPC256406
0.9184	High Similarity	NPC31363
0.9184	High Similarity	NPC208043
0.9184	High Similarity	NPC474170
0.9184	High Similarity	NPC474388
0.9184	High Similarity	NPC472535
0.9184	High Similarity	NPC226973
0.9178	High Similarity	NPC287101
0.9178	High Similarity	NPC223579
0.9178	High Similarity	NPC181250
0.9178	High Similarity	NPC264550
0.9178	High Similarity	NPC40290
0.9178	High Similarity	NPC264289
0.9178	High Similarity	NPC159103
0.9178	High Similarity	NPC195763
0.9178	High Similarity	NPC328119
0.9178	High Similarity	NPC48479
0.9178	High Similarity	NPC52005
0.9178	High Similarity	NPC183950
0.9178	High Similarity	NPC142876
0.9178	High Similarity	NPC333691
0.9178	High Similarity	NPC139293
0.9178	High Similarity	NPC177298
0.9178	High Similarity	NPC200060
0.9178	High Similarity	NPC137062
0.9178	High Similarity	NPC69430
0.9161	High Similarity	NPC119663
0.9155	High Similarity	NPC171094
0.9155	High Similarity	NPC58229
0.9139	High Similarity	NPC474960
0.9137	High Similarity	NPC125269
0.9133	High Similarity	NPC476981
0.9133	High Similarity	NPC129684
0.9133	High Similarity	NPC52889
0.9133	High Similarity	NPC67876
0.9133	High Similarity	NPC310206
0.9133	High Similarity	NPC299520
0.9133	High Similarity	NPC284820
0.9133	High Similarity	NPC181960
0.9133	High Similarity	NPC473272
0.9133	High Similarity	NPC291508
0.913	High Similarity	NPC182428
0.913	High Similarity	NPC473655
0.913	High Similarity	NPC101294
0.9128	High Similarity	NPC37392
0.9128	High Similarity	NPC226025
0.9128	High Similarity	NPC152951
0.9128	High Similarity	NPC117992
0.9128	High Similarity	NPC256612
0.9128	High Similarity	NPC472280
0.9128	High Similarity	NPC230149
0.9128	High Similarity	NPC472909
0.9128	High Similarity	NPC471746
0.9128	High Similarity	NPC57674
0.9128	High Similarity	NPC168247
0.9128	High Similarity	NPC284353
0.9128	High Similarity	NPC213622
0.9128	High Similarity	NPC20830
0.9122	High Similarity	NPC471982
0.9122	High Similarity	NPC474993
0.9122	High Similarity	NPC134677
0.9122	High Similarity	NPC55205
0.9122	High Similarity	NPC219582
0.9122	High Similarity	NPC260979
0.9122	High Similarity	NPC236637
0.9122	High Similarity	NPC302950
0.9122	High Similarity	NPC237994
0.9116	High Similarity	NPC239363
0.9116	High Similarity	NPC177839
0.9116	High Similarity	NPC156953
0.9116	High Similarity	NPC219330
0.9116	High Similarity	NPC29231
0.9116	High Similarity	NPC306821
0.911	High Similarity	NPC120464
0.9091	High Similarity	NPC28326
0.9085	High Similarity	NPC136095
0.9079	High Similarity	NPC165549
0.9079	High Similarity	NPC34376
0.9073	High Similarity	NPC204879
0.9071	High Similarity	NPC99854
0.9067	High Similarity	NPC303255
0.9067	High Similarity	NPC35038
0.9067	High Similarity	NPC282307
0.9067	High Similarity	NPC155063
0.9067	High Similarity	NPC278778
0.9067	High Similarity	NPC472916
0.9067	High Similarity	NPC170026
0.9067	High Similarity	NPC291878
0.9067	High Similarity	NPC265511
0.9067	High Similarity	NPC195796
0.906	High Similarity	NPC78326
0.906	High Similarity	NPC183878
0.906	High Similarity	NPC86485
0.906	High Similarity	NPC47781
0.906	High Similarity	NPC160951
0.906	High Similarity	NPC124714
0.906	High Similarity	NPC33051
0.906	High Similarity	NPC279930
0.906	High Similarity	NPC49402
0.906	High Similarity	NPC273462
0.906	High Similarity	NPC473664
0.906	High Similarity	NPC255350
0.906	High Similarity	NPC176775
0.906	High Similarity	NPC236223
0.906	High Similarity	NPC270620
0.906	High Similarity	NPC145379
0.906	High Similarity	NPC22519
0.906	High Similarity	NPC179126
0.906	High Similarity	NPC274327

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 NPC471590 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	436
0.1-0.2	998
0.2-0.3	1699
0.3-0.4	2699
0.4-0.5	1791
0.5-0.6	946
0.6-0.7	417
0.7-0.8	111
0.8-0.85	38
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9281	High Similarity	NPD2796	Approved
0.9128	High Similarity	NPD3817	Phase 2
0.9122	High Similarity	NPD1934	Approved
0.906	High Similarity	NPD2801	Approved
0.9013	High Similarity	NPD5494	Approved
0.894	High Similarity	NPD3882	Suspended
0.8933	High Similarity	NPD2393	Clinical (unspecified phase)
0.8836	High Similarity	NPD1511	Approved
0.8716	High Similarity	NPD1512	Approved
0.8707	High Similarity	NPD6799	Approved
0.8701	High Similarity	NPD919	Approved
0.8671	High Similarity	NPD3818	Discontinued
0.8671	High Similarity	NPD1510	Phase 2
0.8662	High Similarity	NPD6166	Phase 2
0.8662	High Similarity	NPD6167	Clinical (unspecified phase)
0.8662	High Similarity	NPD6168	Clinical (unspecified phase)
0.8649	High Similarity	NPD4378	Clinical (unspecified phase)
0.8621	High Similarity	NPD1549	Phase 2
0.8599	High Similarity	NPD3926	Phase 2
0.859	High Similarity	NPD1247	Approved
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8562	High Similarity	NPD7819	Suspended
0.8552	High Similarity	NPD1550	Clinical (unspecified phase)
0.8552	High Similarity	NPD1552	Clinical (unspecified phase)
0.8533	High Similarity	NPD6980	Clinical (unspecified phase)
0.85	High Similarity	NPD7054	Approved
0.8497	Intermediate Similarity	NPD6801	Discontinued
0.8487	Intermediate Similarity	NPD4380	Phase 2
0.8487	Intermediate Similarity	NPD6599	Discontinued
0.8447	Intermediate Similarity	NPD7472	Approved
0.8447	Intermediate Similarity	NPD7074	Phase 3
0.84	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7075	Discontinued
0.8392	Intermediate Similarity	NPD1240	Approved
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD7411	Suspended
0.8293	Intermediate Similarity	NPD7808	Phase 3
0.8288	Intermediate Similarity	NPD3748	Approved
0.8282	Intermediate Similarity	NPD6797	Phase 2
0.8276	Intermediate Similarity	NPD1607	Approved
0.8232	Intermediate Similarity	NPD7251	Discontinued
0.8207	Intermediate Similarity	NPD1933	Approved
0.8188	Intermediate Similarity	NPD1243	Approved
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8182	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD920	Approved
0.817	Intermediate Similarity	NPD5403	Approved
0.816	Intermediate Similarity	NPD5844	Phase 1
0.8158	Intermediate Similarity	NPD5401	Approved
0.8153	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD5402	Approved
0.8148	Intermediate Similarity	NPD7473	Discontinued
0.8146	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD943	Approved
0.8013	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD6832	Phase 2
0.7947	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6959	Discontinued
0.7875	Intermediate Similarity	NPD7768	Phase 2
0.7867	Intermediate Similarity	NPD1551	Phase 2
0.7866	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1465	Phase 2
0.7844	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD447	Suspended
0.7838	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5242	Approved
0.7798	Intermediate Similarity	NPD6559	Discontinued
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.777	Intermediate Similarity	NPD5536	Phase 2
0.7748	Intermediate Similarity	NPD2935	Discontinued
0.7742	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD2798	Approved
0.7716	Intermediate Similarity	NPD3749	Approved
0.7697	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2799	Discontinued
0.7662	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1613	Approved
0.7635	Intermediate Similarity	NPD2313	Discontinued
0.7625	Intermediate Similarity	NPD6385	Approved
0.7625	Intermediate Similarity	NPD6386	Approved
0.7619	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD230	Phase 1
0.7598	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2654	Approved
0.7597	Intermediate Similarity	NPD2800	Approved
0.7593	Intermediate Similarity	NPD5353	Approved
0.7582	Intermediate Similarity	NPD2344	Approved
0.758	Intermediate Similarity	NPD2532	Approved
0.758	Intermediate Similarity	NPD2533	Approved
0.758	Intermediate Similarity	NPD2534	Approved
0.7569	Intermediate Similarity	NPD3972	Approved
0.7568	Intermediate Similarity	NPD3027	Phase 3
0.7551	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3018	Phase 2
0.7546	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3266	Approved
0.7534	Intermediate Similarity	NPD3267	Approved
0.7533	Intermediate Similarity	NPD4307	Phase 2
0.7529	Intermediate Similarity	NPD5953	Discontinued
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.7483	Intermediate Similarity	NPD17	Approved
0.7482	Intermediate Similarity	NPD1241	Discontinued
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7451	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7033	Discontinued
0.7448	Intermediate Similarity	NPD2981	Phase 2
0.744	Intermediate Similarity	NPD2403	Approved
0.7434	Intermediate Similarity	NPD6651	Approved
0.7432	Intermediate Similarity	NPD9494	Approved
0.7415	Intermediate Similarity	NPD1203	Approved
0.7412	Intermediate Similarity	NPD7286	Phase 2
0.74	Intermediate Similarity	NPD1296	Phase 2
0.74	Intermediate Similarity	NPD3268	Approved
0.7397	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2982	Phase 2
0.7397	Intermediate Similarity	NPD2983	Phase 2
0.7389	Intermediate Similarity	NPD3887	Approved
0.7389	Intermediate Similarity	NPD2309	Approved
0.7383	Intermediate Similarity	NPD4908	Phase 1
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7362	Intermediate Similarity	NPD37	Approved
0.7357	Intermediate Similarity	NPD5283	Phase 1
0.7355	Intermediate Similarity	NPD1471	Phase 3
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7343	Intermediate Similarity	NPD1548	Phase 1
0.7338	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4308	Phase 3
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD4966	Approved
0.7329	Intermediate Similarity	NPD1608	Approved
0.7329	Intermediate Similarity	NPD9717	Approved
0.7329	Intermediate Similarity	NPD1653	Approved
0.7325	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3787	Discontinued
0.7301	Intermediate Similarity	NPD5889	Approved
0.7301	Intermediate Similarity	NPD5890	Approved
0.7297	Intermediate Similarity	NPD2797	Approved
0.7288	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD4288	Approved
0.726	Intermediate Similarity	NPD1610	Phase 2
0.7256	Intermediate Similarity	NPD6844	Discontinued
0.7256	Intermediate Similarity	NPD6279	Approved
0.7256	Intermediate Similarity	NPD6280	Approved
0.725	Intermediate Similarity	NPD4661	Approved
0.725	Intermediate Similarity	NPD4662	Approved
0.725	Intermediate Similarity	NPD3146	Approved
0.725	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6234	Discontinued
0.7244	Intermediate Similarity	NPD2353	Approved
0.7244	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1876	Approved
0.719	Intermediate Similarity	NPD3142	Approved
0.719	Intermediate Similarity	NPD3140	Approved
0.7188	Intermediate Similarity	NPD7390	Discontinued
0.7188	Intermediate Similarity	NPD4357	Discontinued
0.7178	Intermediate Similarity	NPD7458	Discontinued
0.7171	Intermediate Similarity	NPD411	Approved
0.717	Intermediate Similarity	NPD6190	Approved
0.7169	Intermediate Similarity	NPD5978	Approved
0.7169	Intermediate Similarity	NPD5977	Approved
0.7151	Intermediate Similarity	NPD2163	Approved
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD6585	Discontinued
0.7127	Intermediate Similarity	NPD4360	Phase 2
0.7127	Intermediate Similarity	NPD4363	Phase 3
0.7119	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6808	Phase 2
0.7118	Intermediate Similarity	NPD7229	Phase 3
0.7114	Intermediate Similarity	NPD3225	Approved
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4110	Phase 3
0.7107	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD4361	Phase 2
0.7088	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7685	Pre-registration
0.7086	Intermediate Similarity	NPD6104	Discontinued
0.7083	Intermediate Similarity	NPD6971	Discontinued
0.7079	Intermediate Similarity	NPD8434	Phase 2
0.7073	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3539	Phase 1

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