NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.08
Volume:	250.242
LogP:	3.285
LogD:	3.124
LogS:	-3.044
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.805
Synthetic Accessibility Score:	2.573
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.692
MDCK Permeability:	2.1667996406904422e-05
Pgp-inhibitor:	0.226
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.111
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	86.01386260986328%
Volume Distribution (VD):	1.39
Pgp-substrate:	13.205477714538574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.904
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.758
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.907
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.733
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	12.466
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.349
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.18
AMES Toxicity:	0.409
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.892
Carcinogencity:	0.631
Eye Corrosion:	0.003
Eye Irritation:	0.826
Respiratory Toxicity:	0.356

Download Data

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

Natural Product: NPC74821

Natural Product ID:	NPC74821
*Common Name:**	Idronoxil
IUPAC Name:	3-(4-hydroxyphenyl)-2H-chromen-7-ol
Synonyms:	Idronoxil; NV-06
Standard InCHIKey:	ZZUBHVMHNVYXRR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-8,16-17H,9H2
SMILES:	c1cc(ccc1C1=Cc2ccc(cc2OC1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1957038
PubChem CID:	219100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0004154] Hydroxyisoflavonoids

*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
NPO24045	Lespedeza homoloba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24045	Lespedeza homoloba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24045	Lespedeza homoloba	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
GI50	7
IC50	4
Others	10
Potency	1

Activity Type	# Activity
Cell Line	5
Individual Protein	1
NON-MOLECULAR	7
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3031	Individual Protein	Estrogen receptor alpha	Rattus norvegicus	IC50	=	660.69	nM	PMID[527982]
NPT171	Cell Line	MRC5	Homo sapiens	GI50	=	109000.0	nM	PMID[527983]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	62900.0	nM	PMID[527983]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	33000.0	nM	PMID[527986]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	31300.0	nM	PMID[527987]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	108500.0	nM	PMID[527987]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	54.0	%	PMID[527983]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	18.0	%	PMID[527983]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	80.0	%	PMID[527983]
NPT27	Others	Unspecified		RatioGI50	=	13.6	n.a.	PMID[527983]
NPT27	Others	Unspecified		RatioGI50	=	1.7	n.a.	PMID[527983]
NPT27	Others	Unspecified		RatioGI50	=	26.4	n.a.	PMID[527983]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	8000.0	nM	PMID[527983]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4100.0	nM	PMID[527983]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	16774.4	nM	PMID[527984]
NPT35	Others	n.a.		LogD7.4	n.a.	3.8	n.a.	PMID[527985]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9900.0	nM	PMID[527986]
NPT2	Others	Unspecified		GI50	=	4500.0	nM	PMID[527987]
NPT2	Others	Unspecified		Selectivity ratio	=	3.5	n.a.	PMID[527987]
NPT2	Others	Unspecified		Selectivity ratio	=	24.1	n.a.	PMID[527987]
NPT2	Others	Unspecified		GI50	>	100000.0	nM	PMID[527987]
NPT2	Others	Unspecified		Selectivity ratio	<	1.0	n.a.	PMID[527987]

☑ 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 NPC74821 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	441
0.1-0.2	1930
0.2-0.3	6235
0.3-0.4	13186
0.4-0.5	3517
0.5-0.6	4913
0.6-0.7	7577
0.7-0.8	4048
0.8-0.85	597
0.85-0.9	195
0.9-0.95	45
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.991	High Similarity	NPC295259
0.9646	High Similarity	NPC258979
0.9646	High Similarity	NPC8283
0.9646	High Similarity	NPC93398
0.9478	High Similarity	NPC54972
0.9478	High Similarity	NPC193364
0.9397	High Similarity	NPC100099
0.9397	High Similarity	NPC36016
0.9316	High Similarity	NPC76465
0.9316	High Similarity	NPC38761
0.9237	High Similarity	NPC197351
0.9237	High Similarity	NPC106914
0.9237	High Similarity	NPC86502
0.9237	High Similarity	NPC246648
0.9237	High Similarity	NPC134195
0.9204	High Similarity	NPC185541
0.9204	High Similarity	NPC464
0.9167	High Similarity	NPC149796
0.916	High Similarity	NPC167571
0.916	High Similarity	NPC188022
0.916	High Similarity	NPC17809
0.916	High Similarity	NPC285040
0.916	High Similarity	NPC278552
0.916	High Similarity	NPC102540
0.916	High Similarity	NPC103420
0.916	High Similarity	NPC207179
0.9145	High Similarity	NPC97432
0.9145	High Similarity	NPC190454
0.9123	High Similarity	NPC85292
0.9123	High Similarity	NPC54507
0.9123	High Similarity	NPC229147
0.9083	High Similarity	NPC26879
0.9083	High Similarity	NPC283049
0.9083	High Similarity	NPC276212
0.9083	High Similarity	NPC471215
0.9083	High Similarity	NPC262573
0.9083	High Similarity	NPC50315
0.9083	High Similarity	NPC230479
0.9076	High Similarity	NPC270030
0.9016	High Similarity	NPC134360
0.9	High Similarity	NPC168259
0.8966	High Similarity	NPC131118
0.8957	High Similarity	NPC203113
0.8943	High Similarity	NPC91291
0.8934	High Similarity	NPC222572
0.8934	High Similarity	NPC39064
0.8934	High Similarity	NPC47283
0.8934	High Similarity	NPC87224
0.8934	High Similarity	NPC38664
0.8934	High Similarity	NPC274717
0.8934	High Similarity	NPC53986
0.8929	High Similarity	NPC106141
0.8917	High Similarity	NPC159132
0.8889	High Similarity	NPC172253
0.8889	High Similarity	NPC59561
0.8871	High Similarity	NPC164804
0.8871	High Similarity	NPC118683
0.8871	High Similarity	NPC211413
0.8871	High Similarity	NPC293203
0.8871	High Similarity	NPC244888
0.8871	High Similarity	NPC68205
0.8862	High Similarity	NPC93962
0.8852	High Similarity	NPC46978
0.8824	High Similarity	NPC52247
0.8793	High Similarity	NPC141090
0.8793	High Similarity	NPC150624
0.8772	High Similarity	NPC280606
0.875	High Similarity	NPC74137
0.8739	High Similarity	NPC102639
0.873	High Similarity	NPC168059
0.873	High Similarity	NPC77196
0.873	High Similarity	NPC229442
0.873	High Similarity	NPC92805
0.872	High Similarity	NPC150011
0.872	High Similarity	NPC118114
0.872	High Similarity	NPC268917
0.872	High Similarity	NPC280653
0.872	High Similarity	NPC129106
0.872	High Similarity	NPC12875
0.872	High Similarity	NPC129784
0.872	High Similarity	NPC196765
0.872	High Similarity	NPC207892
0.872	High Similarity	NPC236014
0.872	High Similarity	NPC228369
0.872	High Similarity	NPC17343
0.872	High Similarity	NPC162801
0.872	High Similarity	NPC476166
0.872	High Similarity	NPC103799
0.872	High Similarity	NPC164574
0.872	High Similarity	NPC300875
0.872	High Similarity	NPC206224
0.8718	High Similarity	NPC33270
0.8718	High Similarity	NPC69261
0.8718	High Similarity	NPC244816
0.8718	High Similarity	NPC474933
0.8718	High Similarity	NPC50521
0.8718	High Similarity	NPC195466
0.8718	High Similarity	NPC221549
0.8707	High Similarity	NPC808
0.8684	High Similarity	NPC296920
0.8684	High Similarity	NPC90520
0.8684	High Similarity	NPC255068
0.8678	High Similarity	NPC474160
0.8667	High Similarity	NPC187868
0.8667	High Similarity	NPC212965
0.8667	High Similarity	NPC476633
0.8661	High Similarity	NPC115335
0.8661	High Similarity	NPC225696
0.8661	High Similarity	NPC106215
0.8661	High Similarity	NPC97834
0.8661	High Similarity	NPC198154
0.8661	High Similarity	NPC296915
0.8661	High Similarity	NPC223008
0.8655	High Similarity	NPC247553
0.8651	High Similarity	NPC126029
0.8651	High Similarity	NPC13005
0.8651	High Similarity	NPC78770
0.8651	High Similarity	NPC261619
0.8651	High Similarity	NPC219876
0.8651	High Similarity	NPC185604
0.8651	High Similarity	NPC61477
0.8651	High Similarity	NPC15658
0.8649	High Similarity	NPC8302
0.864	High Similarity	NPC32463
0.864	High Similarity	NPC470225
0.864	High Similarity	NPC27187
0.8629	High Similarity	NPC46274
0.8629	High Similarity	NPC226331
0.8621	High Similarity	NPC22610
0.8621	High Similarity	NPC276737
0.8621	High Similarity	NPC180508
0.8621	High Similarity	NPC228287
0.8621	High Similarity	NPC161696
0.8607	High Similarity	NPC228503
0.8607	High Similarity	NPC138248
0.8596	High Similarity	NPC94045
0.8595	High Similarity	NPC120638
0.8583	High Similarity	NPC215037
0.8583	High Similarity	NPC85435
0.8583	High Similarity	NPC302107
0.8583	High Similarity	NPC218753
0.8583	High Similarity	NPC11060
0.8571	High Similarity	NPC42760
0.8571	High Similarity	NPC137294
0.8571	High Similarity	NPC268266
0.8571	High Similarity	NPC220825
0.8571	High Similarity	NPC181497
0.8571	High Similarity	NPC184302
0.8571	High Similarity	NPC268342
0.8571	High Similarity	NPC85895
0.8571	High Similarity	NPC271945
0.8571	High Similarity	NPC250727
0.8548	High Similarity	NPC250432
0.8548	High Similarity	NPC5447
0.8547	High Similarity	NPC53906
0.8547	High Similarity	NPC167934
0.8537	High Similarity	NPC244495
0.8537	High Similarity	NPC105718
0.8537	High Similarity	NPC476254
0.8537	High Similarity	NPC113495
0.8537	High Similarity	NPC93219
0.8537	High Similarity	NPC278955
0.8537	High Similarity	NPC131397
0.8527	High Similarity	NPC20829
0.8527	High Similarity	NPC262585
0.8527	High Similarity	NPC18189
0.8525	High Similarity	NPC315807
0.8516	High Similarity	NPC117048
0.8516	High Similarity	NPC473107
0.8516	High Similarity	NPC124085
0.8516	High Similarity	NPC476615
0.8516	High Similarity	NPC476616
0.8516	High Similarity	NPC317380
0.8516	High Similarity	NPC476617
0.8509	High Similarity	NPC265211
0.8509	High Similarity	NPC306045
0.8504	High Similarity	NPC86655
0.8504	High Similarity	NPC113006
0.8504	High Similarity	NPC202762
0.8504	High Similarity	NPC307289
0.8492	Intermediate Similarity	NPC474481
0.8487	Intermediate Similarity	NPC190514
0.8487	Intermediate Similarity	NPC96705
0.8468	Intermediate Similarity	NPC170485
0.8455	Intermediate Similarity	NPC256015
0.8455	Intermediate Similarity	NPC228972
0.8455	Intermediate Similarity	NPC294156
0.8455	Intermediate Similarity	NPC122792
0.845	Intermediate Similarity	NPC151224
0.845	Intermediate Similarity	NPC474206
0.845	Intermediate Similarity	NPC195022
0.845	Intermediate Similarity	NPC470356
0.845	Intermediate Similarity	NPC473413
0.845	Intermediate Similarity	NPC125579
0.845	Intermediate Similarity	NPC112246
0.845	Intermediate Similarity	NPC15109
0.845	Intermediate Similarity	NPC121812
0.845	Intermediate Similarity	NPC164787
0.845	Intermediate Similarity	NPC61946
0.845	Intermediate Similarity	NPC94750

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 NPC74821 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	1009
0.2-0.3	1710
0.3-0.4	2694
0.4-0.5	1587
0.5-0.6	1007
0.6-0.7	596
0.7-0.8	127
0.8-0.85	11
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1548	Phase 1
0.9478	High Similarity	NPD1610	Phase 2
0.8934	High Similarity	NPD4908	Phase 1
0.8824	High Similarity	NPD422	Phase 1
0.879	High Similarity	NPD4907	Clinical (unspecified phase)
0.8651	High Similarity	NPD1612	Clinical (unspecified phase)
0.8651	High Similarity	NPD1613	Approved
0.8629	High Similarity	NPD1529	Clinical (unspecified phase)
0.8548	High Similarity	NPD1530	Clinical (unspecified phase)
0.8407	Intermediate Similarity	NPD968	Approved
0.8346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8268	Intermediate Similarity	NPD4625	Phase 3
0.8258	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD2861	Phase 2
0.8226	Intermediate Similarity	NPD4749	Approved
0.8195	Intermediate Similarity	NPD1549	Phase 2
0.8106	Intermediate Similarity	NPD1510	Phase 2
0.8062	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD940	Approved
0.8053	Intermediate Similarity	NPD846	Approved
0.8029	Intermediate Similarity	NPD7212	Phase 2
0.8029	Intermediate Similarity	NPD7213	Phase 3
0.8017	Intermediate Similarity	NPD290	Approved
0.7984	Intermediate Similarity	NPD3027	Phase 3
0.7971	Intermediate Similarity	NPD7447	Phase 1
0.7965	Intermediate Similarity	NPD1242	Phase 1
0.7941	Intermediate Similarity	NPD3750	Approved
0.7939	Intermediate Similarity	NPD1240	Approved
0.792	Intermediate Similarity	NPD1091	Approved
0.7879	Intermediate Similarity	NPD5124	Phase 1
0.7879	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD3225	Approved
0.7842	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1607	Approved
0.7797	Intermediate Similarity	NPD2684	Approved
0.7795	Intermediate Similarity	NPD6582	Phase 2
0.7795	Intermediate Similarity	NPD6583	Phase 3
0.7778	Intermediate Similarity	NPD2796	Approved
0.7778	Intermediate Similarity	NPD1551	Phase 2
0.777	Intermediate Similarity	NPD1511	Approved
0.7737	Intermediate Similarity	NPD1652	Phase 2
0.7686	Intermediate Similarity	NPD821	Approved
0.7674	Intermediate Similarity	NPD2797	Approved
0.766	Intermediate Similarity	NPD1512	Approved
0.7642	Intermediate Similarity	NPD6671	Approved
0.7634	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6516	Phase 2
0.7619	Intermediate Similarity	NPD5846	Approved
0.7615	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD6584	Phase 3
0.76	Intermediate Similarity	NPD1894	Discontinued
0.7589	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7033	Discontinued
0.7574	Intermediate Similarity	NPD3748	Approved
0.7557	Intermediate Similarity	NPD3018	Phase 2
0.7541	Intermediate Similarity	NPD7843	Approved
0.7541	Intermediate Similarity	NPD5535	Approved
0.7522	Intermediate Similarity	NPD2933	Approved
0.7522	Intermediate Similarity	NPD2934	Approved
0.7519	Intermediate Similarity	NPD1296	Phase 2
0.7518	Intermediate Similarity	NPD6099	Approved
0.7518	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD1535	Discovery
0.7481	Intermediate Similarity	NPD4340	Discontinued
0.7466	Intermediate Similarity	NPD1934	Approved
0.7462	Intermediate Similarity	NPD8651	Approved
0.7459	Intermediate Similarity	NPD228	Approved
0.7456	Intermediate Similarity	NPD2860	Approved
0.7456	Intermediate Similarity	NPD2859	Approved
0.7448	Intermediate Similarity	NPD4380	Phase 2
0.7442	Intermediate Similarity	NPD1481	Phase 2
0.7438	Intermediate Similarity	NPD5451	Approved
0.7431	Intermediate Similarity	NPD1653	Approved
0.7429	Intermediate Similarity	NPD7466	Approved
0.7429	Intermediate Similarity	NPD3892	Phase 2
0.7415	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2801	Approved
0.741	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4060	Phase 1
0.7405	Intermediate Similarity	NPD1203	Approved
0.7397	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7411	Suspended
0.7395	Intermediate Similarity	NPD9697	Approved
0.7394	Intermediate Similarity	NPD6799	Approved
0.7388	Intermediate Similarity	NPD6798	Discontinued
0.7388	Intermediate Similarity	NPD3268	Approved
0.7385	Intermediate Similarity	NPD2983	Phase 2
0.7385	Intermediate Similarity	NPD2982	Phase 2
0.7385	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5403	Approved
0.736	Intermediate Similarity	NPD7157	Approved
0.736	Intermediate Similarity	NPD2557	Approved
0.7357	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1778	Approved
0.7343	Intermediate Similarity	NPD5401	Approved
0.7339	Intermediate Similarity	NPD1241	Discontinued
0.7323	Intermediate Similarity	NPD1182	Approved
0.7323	Intermediate Similarity	NPD6581	Approved
0.7323	Intermediate Similarity	NPD6580	Approved
0.7315	Intermediate Similarity	NPD7768	Phase 2
0.7308	Intermediate Similarity	NPD2981	Phase 2
0.7308	Intermediate Similarity	NPD1608	Approved
0.7302	Intermediate Similarity	NPD3596	Phase 2
0.7299	Intermediate Similarity	NPD3054	Approved
0.7299	Intermediate Similarity	NPD3052	Approved
0.7295	Intermediate Similarity	NPD4750	Phase 3
0.7279	Intermediate Similarity	NPD1558	Phase 1
0.7267	Intermediate Similarity	NPD7075	Discontinued
0.7266	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD3020	Approved
0.7246	Intermediate Similarity	NPD4536	Approved
0.7246	Intermediate Similarity	NPD2200	Suspended
0.7246	Intermediate Similarity	NPD4538	Approved
0.7246	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6801	Discontinued
0.7218	Intermediate Similarity	NPD3690	Phase 2
0.7218	Intermediate Similarity	NPD3691	Phase 2
0.7206	Intermediate Similarity	NPD6233	Phase 2
0.72	Intermediate Similarity	NPD3882	Suspended
0.72	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5960	Phase 3
0.7194	Intermediate Similarity	NPD5588	Approved
0.7183	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7819	Suspended
0.7176	Intermediate Similarity	NPD2235	Phase 2
0.7176	Intermediate Similarity	NPD2231	Phase 2
0.7176	Intermediate Similarity	NPD1840	Phase 2
0.7164	Intermediate Similarity	NPD4993	Discontinued
0.7154	Intermediate Similarity	NPD3496	Discontinued
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3817	Phase 2
0.7132	Intermediate Similarity	NPD3444	Approved
0.7132	Intermediate Similarity	NPD3049	Approved
0.7132	Intermediate Similarity	NPD3443	Approved
0.7132	Intermediate Similarity	NPD3445	Approved
0.7105	Intermediate Similarity	NPD9365	Approved
0.7103	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6355	Discontinued
0.7095	Intermediate Similarity	NPD6599	Discontinued
0.7087	Intermediate Similarity	NPD709	Approved
0.7083	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6666	Approved
0.7083	Intermediate Similarity	NPD6667	Approved
0.708	Intermediate Similarity	NPD7477	Discontinued
0.7077	Intermediate Similarity	NPD17	Approved
0.7077	Intermediate Similarity	NPD2556	Approved
0.7077	Intermediate Similarity	NPD2554	Approved
0.7071	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4308	Phase 3
0.7068	Intermediate Similarity	NPD6696	Suspended
0.7063	Intermediate Similarity	NPD5283	Phase 1
0.7059	Intermediate Similarity	NPD6179	Discontinued
0.7059	Intermediate Similarity	NPD5163	Phase 2
0.7054	Intermediate Similarity	NPD9545	Approved
0.705	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3134	Approved
0.7045	Intermediate Similarity	NPD9717	Approved
0.7039	Intermediate Similarity	NPD3749	Approved
0.7029	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2238	Phase 2
0.7027	Intermediate Similarity	NPD111	Approved
0.7023	Intermediate Similarity	NPD3847	Discontinued
0.702	Intermediate Similarity	NPD4288	Approved
0.702	Intermediate Similarity	NPD5402	Approved
0.7007	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6382	Discontinued
0.6993	Remote Similarity	NPD1243	Approved
0.6992	Remote Similarity	NPD5327	Phase 3
0.6992	Remote Similarity	NPD6540	Phase 3
0.6992	Remote Similarity	NPD3685	Discontinued
0.6992	Remote Similarity	NPD6542	Approved
0.6992	Remote Similarity	NPD6543	Approved
0.6992	Remote Similarity	NPD1358	Approved
0.6992	Remote Similarity	NPD6539	Approved
0.6987	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6166	Phase 2
0.6987	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6832	Phase 2
0.698	Remote Similarity	NPD4678	Approved
0.698	Remote Similarity	NPD4675	Approved
0.6978	Remote Similarity	NPD5735	Approved
0.6972	Remote Similarity	NPD3540	Phase 1
0.6966	Remote Similarity	NPD5058	Phase 3
0.6966	Remote Similarity	NPD6815	Approved
0.6962	Remote Similarity	NPD7054	Approved
0.6962	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4062	Phase 3

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