NPASS Compound

Structure

NPC52475 OpenBabel07101718192D 26 29 0 0 0 0 0 0 0 0999 V2000 3.1277 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 4.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 2.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 4.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 14 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 11 1 0 0 0 0 7 17 2 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 12 19 2 0 0 0 0 13 18 2 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	351.11
Volume:	351.47
LogP:	2.909
LogD:	2.57
LogS:	-5.473
# Rotatable Bonds:	3
TPSA:	88.02
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.674
Synthetic Accessibility Score:	2.584
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.043
MDCK Permeability:	8.210716259782203e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.588
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.103
30% Bioavailability (F30%):	0.867

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	94.72606658935547%
Volume Distribution (VD):	0.945
Pgp-substrate:	5.7706217765808105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.888
CYP1A2-substrate:	0.91
CYP2C19-inhibitor:	0.296
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.422
CYP2C9-substrate:	0.783
CYP2D6-inhibitor:	0.287
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.694
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	8.454
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.138
Human Hepatotoxicity (H-HT):	0.387
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.567
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.583
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.366

Download Data

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

Natural Product: NPC52475

Natural Product ID:	NPC52475
*Common Name:**	Vitedoamine B
IUPAC Name:	7-hydroxy-9-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2,3-dihydrobenzo[f]isoindol-1-one
Synonyms:	vitedoamine B
Standard InCHIKey:	XMWQLKFMFCEWGA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H17NO5/c1-25-16-6-10(3-4-14(16)22)18-13-8-15(23)17(26-2)7-11(13)5-12-9-21-20(24)19(12)18/h3-8,22-23H,9H2,1-2H3,(H,21,24)
SMILES:	COc1cc2cc3CN=C(c3c(c2cc1O)c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079288
PubChem CID:	44478947
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001610] Arylnaphthalene lignans

*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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	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
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	870.0	nM	PMID[568107]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	56.18	%	PMID[568107]

☑ 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 NPC52475 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	276
0.1-0.2	1579
0.2-0.3	6804
0.3-0.4	11131
0.4-0.5	5336
0.5-0.6	10734
0.6-0.7	5393
0.7-0.8	1285
0.8-0.85	146
0.85-0.9	11
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC18614
0.8658	High Similarity	NPC5462
0.8531	High Similarity	NPC114102
0.8506	High Similarity	NPC275027
0.8506	High Similarity	NPC26601
0.8483	Intermediate Similarity	NPC218530
0.8481	Intermediate Similarity	NPC60186
0.8472	Intermediate Similarity	NPC130595
0.8472	Intermediate Similarity	NPC93882
0.8472	Intermediate Similarity	NPC214869
0.8462	Intermediate Similarity	NPC35961
0.8462	Intermediate Similarity	NPC195749
0.8462	Intermediate Similarity	NPC52029
0.8462	Intermediate Similarity	NPC186063
0.8414	Intermediate Similarity	NPC6854
0.8414	Intermediate Similarity	NPC285078
0.8414	Intermediate Similarity	NPC313737
0.8392	Intermediate Similarity	NPC155838
0.8385	Intermediate Similarity	NPC210140
0.8333	Intermediate Similarity	NPC222039
0.8333	Intermediate Similarity	NPC100478
0.8323	Intermediate Similarity	NPC127402
0.8323	Intermediate Similarity	NPC28425
0.8322	Intermediate Similarity	NPC251571
0.8313	Intermediate Similarity	NPC311936
0.8276	Intermediate Similarity	NPC255550
0.8276	Intermediate Similarity	NPC308885
0.8263	Intermediate Similarity	NPC119579
0.8261	Intermediate Similarity	NPC134858
0.8247	Intermediate Similarity	NPC428
0.8247	Intermediate Similarity	NPC135538
0.8247	Intermediate Similarity	NPC24233
0.8247	Intermediate Similarity	NPC147390
0.8247	Intermediate Similarity	NPC476571
0.8247	Intermediate Similarity	NPC246587
0.8232	Intermediate Similarity	NPC231371
0.8204	Intermediate Similarity	NPC192939
0.8204	Intermediate Similarity	NPC215747
0.8199	Intermediate Similarity	NPC233650
0.8194	Intermediate Similarity	NPC186898
0.8194	Intermediate Similarity	NPC153990
0.8188	Intermediate Similarity	NPC41473
0.8188	Intermediate Similarity	NPC312770
0.8188	Intermediate Similarity	NPC14600
0.8188	Intermediate Similarity	NPC204848
0.8188	Intermediate Similarity	NPC160607
0.8187	Intermediate Similarity	NPC166014
0.8187	Intermediate Similarity	NPC27410
0.8182	Intermediate Similarity	NPC253883
0.8182	Intermediate Similarity	NPC321505
0.8182	Intermediate Similarity	NPC90844
0.8182	Intermediate Similarity	NPC266705
0.8182	Intermediate Similarity	NPC29008
0.8182	Intermediate Similarity	NPC228771
0.8182	Intermediate Similarity	NPC95075
0.8182	Intermediate Similarity	NPC179825
0.8182	Intermediate Similarity	NPC191376
0.8165	Intermediate Similarity	NPC107602
0.8163	Intermediate Similarity	NPC228843
0.8144	Intermediate Similarity	NPC260118
0.8133	Intermediate Similarity	NPC299583
0.8125	Intermediate Similarity	NPC329837
0.8125	Intermediate Similarity	NPC301713
0.8086	Intermediate Similarity	NPC324144
0.8084	Intermediate Similarity	NPC265383
0.8077	Intermediate Similarity	NPC103379
0.8077	Intermediate Similarity	NPC219162
0.8077	Intermediate Similarity	NPC477565
0.807	Intermediate Similarity	NPC22928
0.8065	Intermediate Similarity	NPC144863
0.8056	Intermediate Similarity	NPC9067
0.8052	Intermediate Similarity	NPC185838
0.8049	Intermediate Similarity	NPC145832
0.8049	Intermediate Similarity	NPC306555
0.8049	Intermediate Similarity	NPC158376
0.8049	Intermediate Similarity	NPC81218
0.8049	Intermediate Similarity	NPC474931
0.8049	Intermediate Similarity	NPC12053
0.8049	Intermediate Similarity	NPC150879
0.8049	Intermediate Similarity	NPC117188
0.8049	Intermediate Similarity	NPC205421
0.8038	Intermediate Similarity	NPC133011
0.8038	Intermediate Similarity	NPC82285
0.8037	Intermediate Similarity	NPC13504
0.8037	Intermediate Similarity	NPC136508
0.8037	Intermediate Similarity	NPC477563
0.8037	Intermediate Similarity	NPC253043
0.8037	Intermediate Similarity	NPC169743
0.8037	Intermediate Similarity	NPC96603
0.8037	Intermediate Similarity	NPC78222
0.8037	Intermediate Similarity	NPC196447
0.8037	Intermediate Similarity	NPC306843
0.8037	Intermediate Similarity	NPC212794
0.8035	Intermediate Similarity	NPC294244
0.8025	Intermediate Similarity	NPC220858
0.8025	Intermediate Similarity	NPC97221
0.8025	Intermediate Similarity	NPC88249
0.8025	Intermediate Similarity	NPC151895
0.8025	Intermediate Similarity	NPC192768
0.8014	Intermediate Similarity	NPC307050
0.8014	Intermediate Similarity	NPC277458
0.8013	Intermediate Similarity	NPC471032
0.8013	Intermediate Similarity	NPC470935
0.8013	Intermediate Similarity	NPC130941
0.8013	Intermediate Similarity	NPC296898
0.8012	Intermediate Similarity	NPC219170
0.8012	Intermediate Similarity	NPC180253
0.7988	Intermediate Similarity	NPC35627
0.7988	Intermediate Similarity	NPC476573
0.7988	Intermediate Similarity	NPC68328
0.7988	Intermediate Similarity	NPC81247
0.7988	Intermediate Similarity	NPC90984
0.7975	Intermediate Similarity	NPC76213
0.7975	Intermediate Similarity	NPC277669
0.7972	Intermediate Similarity	NPC471314
0.7972	Intermediate Similarity	NPC471315
0.7964	Intermediate Similarity	NPC474051
0.7962	Intermediate Similarity	NPC92541
0.7962	Intermediate Similarity	NPC77359
0.7961	Intermediate Similarity	NPC220344
0.7961	Intermediate Similarity	NPC132804
0.7961	Intermediate Similarity	NPC243996
0.7961	Intermediate Similarity	NPC275061
0.7949	Intermediate Similarity	NPC476151
0.7937	Intermediate Similarity	NPC184026
0.7937	Intermediate Similarity	NPC278799
0.7937	Intermediate Similarity	NPC2413
0.7937	Intermediate Similarity	NPC193949
0.7937	Intermediate Similarity	NPC127674
0.7937	Intermediate Similarity	NPC204828
0.7937	Intermediate Similarity	NPC189266
0.7937	Intermediate Similarity	NPC276588
0.7937	Intermediate Similarity	NPC207757
0.7937	Intermediate Similarity	NPC54379
0.7937	Intermediate Similarity	NPC5238
0.7937	Intermediate Similarity	NPC469817
0.7937	Intermediate Similarity	NPC249797
0.7937	Intermediate Similarity	NPC39701
0.7937	Intermediate Similarity	NPC172765
0.7937	Intermediate Similarity	NPC295691
0.7937	Intermediate Similarity	NPC110416
0.7935	Intermediate Similarity	NPC145304
0.7933	Intermediate Similarity	NPC141023
0.7919	Intermediate Similarity	NPC227002
0.7908	Intermediate Similarity	NPC12668
0.7908	Intermediate Similarity	NPC308768
0.7895	Intermediate Similarity	NPC200935
0.7895	Intermediate Similarity	NPC230919
0.7895	Intermediate Similarity	NPC266453
0.7895	Intermediate Similarity	NPC56329
0.7895	Intermediate Similarity	NPC276060
0.7895	Intermediate Similarity	NPC242715
0.7895	Intermediate Similarity	NPC22902
0.7892	Intermediate Similarity	NPC66573
0.7887	Intermediate Similarity	NPC103916
0.7881	Intermediate Similarity	NPC301050
0.7881	Intermediate Similarity	NPC131204
0.7875	Intermediate Similarity	NPC477564
0.7875	Intermediate Similarity	NPC2295
0.7866	Intermediate Similarity	NPC1229
0.7857	Intermediate Similarity	NPC477020
0.7857	Intermediate Similarity	NPC66341
0.7857	Intermediate Similarity	NPC192135
0.7848	Intermediate Similarity	NPC207824
0.7848	Intermediate Similarity	NPC60538
0.7848	Intermediate Similarity	NPC211296
0.7847	Intermediate Similarity	NPC30462
0.7844	Intermediate Similarity	NPC26240
0.7844	Intermediate Similarity	NPC69712
0.7844	Intermediate Similarity	NPC477562
0.7843	Intermediate Similarity	NPC243759
0.7843	Intermediate Similarity	NPC218131
0.7843	Intermediate Similarity	NPC105847
0.784	Intermediate Similarity	NPC206736
0.784	Intermediate Similarity	NPC235628
0.784	Intermediate Similarity	NPC195766
0.7834	Intermediate Similarity	NPC16436
0.7831	Intermediate Similarity	NPC298979
0.7829	Intermediate Similarity	NPC193528
0.7829	Intermediate Similarity	NPC30632
0.7826	Intermediate Similarity	NPC76079
0.7826	Intermediate Similarity	NPC244112
0.7824	Intermediate Similarity	NPC114364
0.7824	Intermediate Similarity	NPC320223
0.7816	Intermediate Similarity	NPC296742
0.7816	Intermediate Similarity	NPC112676
0.7815	Intermediate Similarity	NPC471942
0.7811	Intermediate Similarity	NPC128560
0.7811	Intermediate Similarity	NPC229166
0.7811	Intermediate Similarity	NPC199465
0.7806	Intermediate Similarity	NPC183709
0.7806	Intermediate Similarity	NPC175838
0.78	Intermediate Similarity	NPC189482
0.78	Intermediate Similarity	NPC73656
0.7799	Intermediate Similarity	NPC274026
0.7798	Intermediate Similarity	NPC239775
0.7792	Intermediate Similarity	NPC474915
0.7792	Intermediate Similarity	NPC188163
0.7792	Intermediate Similarity	NPC328750
0.7792	Intermediate Similarity	NPC213206

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 NPC52475 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	797
0.2-0.3	898
0.3-0.4	2015
0.4-0.5	2612
0.5-0.6	1792
0.6-0.7	720
0.7-0.8	128
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8472	Intermediate Similarity	NPD2674	Phase 3
0.8276	Intermediate Similarity	NPD3145	Approved
0.8276	Intermediate Similarity	NPD3144	Approved
0.8042	Intermediate Similarity	NPD1669	Approved
0.8039	Intermediate Similarity	NPD6331	Phase 2
0.7975	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2161	Phase 2
0.7853	Intermediate Similarity	NPD7833	Phase 2
0.7853	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7831	Phase 2
0.7806	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4123	Phase 3
0.764	Intermediate Similarity	NPD4005	Discontinued
0.7597	Intermediate Similarity	NPD4108	Discontinued
0.7582	Intermediate Similarity	NPD4097	Suspended
0.7576	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3620	Phase 2
0.7566	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7153	Discontinued
0.7558	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5241	Discontinued
0.753	Intermediate Similarity	NPD4055	Discovery
0.75	Intermediate Similarity	NPD4584	Approved
0.7485	Intermediate Similarity	NPD4675	Approved
0.7485	Intermediate Similarity	NPD4678	Approved
0.7484	Intermediate Similarity	NPD3845	Phase 1
0.7483	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2898	Approved
0.7456	Intermediate Similarity	NPD4010	Discontinued
0.7455	Intermediate Similarity	NPD5929	Approved
0.7453	Intermediate Similarity	NPD4319	Phase 2
0.7451	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7438	Suspended
0.7439	Intermediate Similarity	NPD3796	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2421	Approved
0.7438	Intermediate Similarity	NPD4357	Discontinued
0.7438	Intermediate Similarity	NPD2420	Approved
0.7434	Intermediate Similarity	NPD5110	Phase 2
0.7434	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5111	Phase 2
0.7434	Intermediate Similarity	NPD5109	Approved
0.7389	Intermediate Similarity	NPD1375	Discontinued
0.7386	Intermediate Similarity	NPD7477	Discontinued
0.7384	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2922	Phase 1
0.7355	Intermediate Similarity	NPD2157	Approved
0.7346	Intermediate Similarity	NPD6090	Discontinued
0.7342	Intermediate Similarity	NPD7037	Approved
0.7312	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6030	Approved
0.7301	Intermediate Similarity	NPD6031	Approved
0.7296	Intermediate Similarity	NPD3060	Approved
0.7289	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8053	Approved
0.7288	Intermediate Similarity	NPD8054	Approved
0.7285	Intermediate Similarity	NPD6584	Phase 3
0.7273	Intermediate Similarity	NPD5617	Suspended
0.7273	Intermediate Similarity	NPD6502	Phase 2
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7267	Intermediate Similarity	NPD27	Approved
0.7267	Intermediate Similarity	NPD2489	Approved
0.7254	Intermediate Similarity	NPD228	Approved
0.7246	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1558	Phase 1
0.7225	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5604	Discontinued
0.7212	Intermediate Similarity	NPD4017	Approved
0.7212	Intermediate Similarity	NPD5811	Approved
0.7211	Intermediate Similarity	NPD4093	Discontinued
0.7209	Intermediate Similarity	NPD4083	Discontinued
0.7208	Intermediate Similarity	NPD5718	Phase 2
0.7202	Intermediate Similarity	NPD2563	Approved
0.7202	Intermediate Similarity	NPD2560	Approved
0.7197	Intermediate Similarity	NPD6896	Approved
0.7197	Intermediate Similarity	NPD6895	Approved
0.719	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5177	Phase 3
0.717	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2668	Approved
0.7162	Intermediate Similarity	NPD2667	Approved
0.7161	Intermediate Similarity	NPD4475	Approved
0.7161	Intermediate Similarity	NPD4474	Approved
0.716	Intermediate Similarity	NPD7773	Phase 2
0.7152	Intermediate Similarity	NPD2883	Discontinued
0.7151	Intermediate Similarity	NPD3051	Approved
0.7151	Intermediate Similarity	NPD6747	Phase 1
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2232	Approved
0.7133	Intermediate Similarity	NPD2233	Approved
0.7133	Intermediate Similarity	NPD2230	Approved
0.7126	Intermediate Similarity	NPD4773	Phase 2
0.7126	Intermediate Similarity	NPD2789	Approved
0.7126	Intermediate Similarity	NPD4772	Phase 2
0.7124	Intermediate Similarity	NPD1712	Approved
0.711	Intermediate Similarity	NPD2970	Approved
0.711	Intermediate Similarity	NPD2969	Approved
0.7108	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7802	Discontinued
0.7086	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6582	Phase 2
0.7086	Intermediate Similarity	NPD6583	Phase 3
0.7086	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7298	Approved
0.7083	Intermediate Similarity	NPD5720	Discontinued
0.7081	Intermediate Similarity	NPD4162	Approved
0.7073	Intermediate Similarity	NPD7020	Approved
0.7073	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7019	Approved
0.7072	Intermediate Similarity	NPD7906	Approved
0.7055	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6071	Discontinued
0.7045	Intermediate Similarity	NPD4873	Discontinued
0.7044	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2978	Approved
0.7041	Intermediate Similarity	NPD2977	Approved
0.7035	Intermediate Similarity	NPD4666	Phase 3
0.7032	Intermediate Similarity	NPD1024	Discontinued
0.703	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD52	Approved
0.703	Intermediate Similarity	NPD7526	Approved
0.7024	Intermediate Similarity	NPD3778	Approved
0.7019	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4060	Phase 1
0.7006	Intermediate Similarity	NPD3920	Phase 2
0.7006	Intermediate Similarity	NPD3109	Approved
0.7006	Intermediate Similarity	NPD3110	Approved
0.7	Intermediate Similarity	NPD5599	Discontinued
0.7	Intermediate Similarity	NPD5977	Approved
0.7	Intermediate Similarity	NPD5978	Approved
0.6993	Remote Similarity	NPD3021	Approved
0.6993	Remote Similarity	NPD3022	Approved
0.6988	Remote Similarity	NPD3640	Phase 3
0.6988	Remote Similarity	NPD3639	Approved
0.6988	Remote Similarity	NPD3641	Approved
0.6987	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1039	Discontinued
0.6978	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5709	Phase 3
0.6975	Remote Similarity	NPD4236	Phase 3
0.6975	Remote Similarity	NPD4237	Approved
0.697	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4739	Approved
0.6962	Remote Similarity	NPD3657	Discovery
0.6944	Remote Similarity	NPD7313	Approved
0.6944	Remote Similarity	NPD7312	Approved
0.6944	Remote Similarity	NPD7311	Approved
0.6944	Remote Similarity	NPD4577	Approved
0.6944	Remote Similarity	NPD7310	Approved
0.6944	Remote Similarity	NPD4578	Approved
0.6941	Remote Similarity	NPD5772	Approved
0.6941	Remote Similarity	NPD5773	Approved
0.6939	Remote Similarity	NPD709	Approved
0.6936	Remote Similarity	NPD6746	Phase 2
0.6933	Remote Similarity	NPD2286	Discontinued
0.6923	Remote Similarity	NPD6072	Discontinued
0.6923	Remote Similarity	NPD4663	Approved
0.6923	Remote Similarity	NPD4951	Discontinued
0.6919	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2808	Discontinued
0.691	Remote Similarity	NPD5557	Phase 1
0.6906	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7309	Approved
0.6901	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8251	Approved
0.6893	Remote Similarity	NPD8099	Discontinued
0.6893	Remote Similarity	NPD3909	Discontinued
0.6893	Remote Similarity	NPD8252	Approved
0.689	Remote Similarity	NPD3692	Discontinued
0.6889	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5976	Discontinued
0.6886	Remote Similarity	NPD2122	Discontinued
0.6886	Remote Similarity	NPD1914	Approved
0.6883	Remote Similarity	NPD3053	Approved
0.6883	Remote Similarity	NPD3055	Approved
0.6882	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1651	Approved
0.6867	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD3924	Approved
0.6865	Remote Similarity	NPD3923	Approved
0.6865	Remote Similarity	NPD3921	Approved
0.6865	Remote Similarity	NPD3922	Approved
0.686	Remote Similarity	NPD6788	Approved
0.6854	Remote Similarity	NPD8156	Discontinued
0.6852	Remote Similarity	NPD3656	Approved
0.6851	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7124	Phase 2

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