NPASS Compound

Structure

CID12377 OpenBabel06191715342D 22 24 0 0 0 0 0 0 0 0999 V2000 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 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 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 -3.4641 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 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 -2.5981 3.5000 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 6 2 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 17 1 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	2.854
LogD:	2.749
LogS:	-3.693
# Rotatable Bonds:	3
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.804
Synthetic Accessibility Score:	2.05
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.666
MDCK Permeability:	3.099261084571481e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	92.9576187133789%
Volume Distribution (VD):	0.511
Pgp-substrate:	5.318198204040527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.88
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.553
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.851
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.863
CYP3A4-substrate:	0.346

ADMET: Excretion

Clearance (CL):	7.115
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.765
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.356
Skin Sensitization:	0.722
Carcinogencity:	0.315
Eye Corrosion:	0.005
Eye Irritation:	0.672
Respiratory Toxicity:	0.4

Download Data

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

Natural Product: NPC12377

Natural Product ID:	NPC12377
*Common Name:**	Cladrin
IUPAC Name:	3-(3,4-dimethoxyphenyl)-7-hydroxychromen-4-one
Synonyms:	Cladrin
Standard InCHIKey:	VFZIJLPRJAQGFO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-20-14-6-3-10(7-16(14)21-2)13-9-22-15-8-11(18)4-5-12(15)17(13)19/h3-9,18H,1-2H3
SMILES:	COc1ccc(cc1OC)c1coc2cc(ccc2c1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454746
PubChem CID:	5748605
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0002687] 4'-O-methylisoflavones

*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
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26690274]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25653	Spatholobus suberectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25653	Spatholobus suberectus	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
Others	16
Potency	23

Activity Type	# Activity
Individual Protein	18
Organism	8
Others	4
Tissue	7
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	25118.9	nM	PMID[549761]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[549761]
NPT537	Individual Protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	3548.1	nM	PMID[549761]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[549761]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	15848.9	nM	PMID[549761]
NPT538	Individual Protein	Niemann-Pick C1 protein	Homo sapiens	Potency	=	3162.3	nM	PMID[549761]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	10000.0	nM	PMID[549761]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[549761]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[549761]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[549761]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	19011.5	nM	PMID[549761]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[549761]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[549761]
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[549761]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[549761]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	FC	=	2.0	n.a.	PMID[549759]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	FC	=	10.5	n.a.	PMID[549759]
NPT2	Others	Unspecified		Ratio	=	2.53	n.a.	PMID[549760]
NPT2	Others	Unspecified		Potency	=	15848.9	nM	PMID[549761]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	13091.8	nM	PMID[549761]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8.3	nM	PMID[549761]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[549761]
NPT2	Others	Unspecified		Potency	n.a.	5623.4	nM	PMID[549761]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	MRT	=	10.8	hr	PMID[549762]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	AUC	=	608.7	ng.hr.mL-1	PMID[549762]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Cmax	=	0.0448	ug.mL-1	PMID[549762]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Tmax	=	0.5	hr	PMID[549762]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	T1/2	=	4.1	hr	PMID[549762]
NPT614	Tissue	Plasma	Rattus norvegicus	Stability	=	81.4	%	PMID[549762]
NPT614	Tissue	Plasma	Rattus norvegicus	Stability	=	84.5	%	PMID[549762]
NPT614	Tissue	Plasma	Rattus norvegicus	Stability	=	106.0	%	PMID[549762]
NPT614	Tissue	Plasma	Rattus norvegicus	Stability	=	88.2	%	PMID[549762]
NPT614	Tissue	Plasma	Rattus norvegicus	Stability	=	98.5	%	PMID[549762]
NPT614	Tissue	Plasma	Rattus norvegicus	Stability	=	93.6	%	PMID[549762]
NPT614	Tissue	Plasma	Rattus norvegicus	Drug recovery	=	83.5	%	PMID[549762]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	GI	=	14.0	%	PMID[549763]
NPT2	Others	Unspecified		Potency	n.a.	4466.8	nM	PMID[549761]

☑ 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 NPC12377 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	433
0.1-0.2	1886
0.2-0.3	4569
0.3-0.4	11448
0.4-0.5	6235
0.5-0.6	3678
0.6-0.7	5165
0.7-0.8	5015
0.8-0.85	2331
0.85-0.9	1348
0.9-0.95	522
0.95-1	67

Similarity Score	Similarity Level	Natural Product ID
0.9858	High Similarity	NPC80710
0.9858	High Similarity	NPC254702
0.9858	High Similarity	NPC203747
0.9858	High Similarity	NPC139364
0.9858	High Similarity	NPC194653
0.9789	High Similarity	NPC264289
0.9789	High Similarity	NPC139293
0.9789	High Similarity	NPC333691
0.9789	High Similarity	NPC264550
0.9789	High Similarity	NPC40290
0.9789	High Similarity	NPC69430
0.9789	High Similarity	NPC200060
0.9789	High Similarity	NPC142876
0.9789	High Similarity	NPC195763
0.972	High Similarity	NPC156953
0.9653	High Similarity	NPC256406
0.9653	High Similarity	NPC262623
0.9648	High Similarity	NPC125449
0.9648	High Similarity	NPC188074
0.9643	High Similarity	NPC119663
0.9586	High Similarity	NPC100971
0.9586	High Similarity	NPC245382
0.9586	High Similarity	NPC269451
0.9586	High Similarity	NPC100263
0.9586	High Similarity	NPC216769
0.9586	High Similarity	NPC181209
0.9586	High Similarity	NPC209487
0.9586	High Similarity	NPC474993
0.9586	High Similarity	NPC121522
0.9586	High Similarity	NPC131266
0.9586	High Similarity	NPC291802
0.9586	High Similarity	NPC35763
0.9583	High Similarity	NPC239363
0.9574	High Similarity	NPC242893
0.9574	High Similarity	NPC38065
0.9571	High Similarity	NPC185607
0.9521	High Similarity	NPC124714
0.9517	High Similarity	NPC45291
0.9517	High Similarity	NPC19980
0.9514	High Similarity	NPC38545
0.9514	High Similarity	NPC171916
0.951	High Similarity	NPC12200
0.9504	High Similarity	NPC254659
0.9456	High Similarity	NPC39184
0.9452	High Similarity	NPC104728
0.9452	High Similarity	NPC35544
0.9448	High Similarity	NPC10467
0.9448	High Similarity	NPC85131
0.9444	High Similarity	NPC195202
0.9444	High Similarity	NPC203077
0.9444	High Similarity	NPC166036
0.9444	High Similarity	NPC238279
0.9437	High Similarity	NPC142165
0.9433	High Similarity	NPC284556
0.9433	High Similarity	NPC301178
0.9424	High Similarity	NPC303644
0.9424	High Similarity	NPC116632
0.9424	High Similarity	NPC181124
0.9424	High Similarity	NPC162680
0.9424	High Similarity	NPC209560
0.9424	High Similarity	NPC7013
0.9424	High Similarity	NPC294409
0.9424	High Similarity	NPC212767
0.9388	High Similarity	NPC250557
0.9388	High Similarity	NPC469550
0.9388	High Similarity	NPC280937
0.9384	High Similarity	NPC31363
0.9384	High Similarity	NPC308451
0.9379	High Similarity	NPC183950
0.9379	High Similarity	NPC137062
0.9379	High Similarity	NPC159103
0.9379	High Similarity	NPC52005
0.9379	High Similarity	NPC287101
0.9379	High Similarity	NPC223579
0.9375	High Similarity	NPC33265
0.9375	High Similarity	NPC93034
0.9375	High Similarity	NPC62536
0.9375	High Similarity	NPC119660
0.9371	High Similarity	NPC471590
0.9366	High Similarity	NPC287722
0.9366	High Similarity	NPC476054
0.9366	High Similarity	NPC471417
0.9362	High Similarity	NPC110419
0.9357	High Similarity	NPC278323
0.9357	High Similarity	NPC279668
0.9357	High Similarity	NPC90665
0.9357	High Similarity	NPC12175
0.9357	High Similarity	NPC55162
0.9357	High Similarity	NPC309154
0.9353	High Similarity	NPC193792
0.9324	High Similarity	NPC31018
0.9324	High Similarity	NPC134287
0.9324	High Similarity	NPC130589
0.9324	High Similarity	NPC234255
0.9324	High Similarity	NPC255807
0.932	High Similarity	NPC324233
0.932	High Similarity	NPC302950
0.932	High Similarity	NPC323626
0.932	High Similarity	NPC257648
0.932	High Similarity	NPC219582
0.932	High Similarity	NPC39732
0.932	High Similarity	NPC55205
0.932	High Similarity	NPC236637
0.932	High Similarity	NPC472912
0.932	High Similarity	NPC260979
0.932	High Similarity	NPC60972
0.932	High Similarity	NPC477231
0.9315	High Similarity	NPC166753
0.9315	High Similarity	NPC338131
0.9315	High Similarity	NPC50728
0.9315	High Similarity	NPC29231
0.9315	High Similarity	NPC472279
0.9315	High Similarity	NPC306821
0.931	High Similarity	NPC218490
0.931	High Similarity	NPC287395
0.931	High Similarity	NPC183655
0.931	High Similarity	NPC120464
0.9306	High Similarity	NPC120924
0.9306	High Similarity	NPC216314
0.9306	High Similarity	NPC195919
0.9301	High Similarity	NPC207732
0.9296	High Similarity	NPC312256
0.9291	High Similarity	NPC295384
0.9286	High Similarity	NPC44573
0.9281	High Similarity	NPC234560
0.9281	High Similarity	NPC39426
0.9267	High Similarity	NPC215375
0.9267	High Similarity	NPC74178
0.9267	High Similarity	NPC184755
0.9267	High Similarity	NPC62518
0.9262	High Similarity	NPC472455
0.9257	High Similarity	NPC18727
0.9257	High Similarity	NPC472915
0.9252	High Similarity	NPC226973
0.9252	High Similarity	NPC149614
0.9252	High Similarity	NPC125062
0.9252	High Similarity	NPC208043
0.9252	High Similarity	NPC252933
0.9252	High Similarity	NPC54394
0.9252	High Similarity	NPC117579
0.9252	High Similarity	NPC236769
0.9252	High Similarity	NPC200740
0.9247	High Similarity	NPC105512
0.9247	High Similarity	NPC48479
0.9247	High Similarity	NPC328119
0.9247	High Similarity	NPC102003
0.9247	High Similarity	NPC177298
0.9247	High Similarity	NPC92722
0.9241	High Similarity	NPC474999
0.9241	High Similarity	NPC95864
0.9241	High Similarity	NPC108406
0.9241	High Similarity	NPC168803
0.9236	High Similarity	NPC157133
0.9225	High Similarity	NPC259166
0.9225	High Similarity	NPC144118
0.9225	High Similarity	NPC80962
0.9225	High Similarity	NPC326109
0.9225	High Similarity	NPC48624
0.9225	High Similarity	NPC101366
0.9225	High Similarity	NPC213659
0.9225	High Similarity	NPC215311
0.9225	High Similarity	NPC172250
0.9225	High Similarity	NPC204985
0.9225	High Similarity	NPC219917
0.9214	High Similarity	NPC235428
0.9214	High Similarity	NPC87545
0.9214	High Similarity	NPC473391
0.9214	High Similarity	NPC472364
0.9205	High Similarity	NPC474960
0.92	High Similarity	NPC291508
0.92	High Similarity	NPC284820
0.92	High Similarity	NPC181960
0.92	High Similarity	NPC210084
0.92	High Similarity	NPC476981
0.92	High Similarity	NPC167595
0.92	High Similarity	NPC52889
0.92	High Similarity	NPC473272
0.92	High Similarity	NPC299520
0.92	High Similarity	NPC129684
0.92	High Similarity	NPC99597
0.92	High Similarity	NPC67876
0.92	High Similarity	NPC52530
0.92	High Similarity	NPC78103
0.9195	High Similarity	NPC213622
0.9195	High Similarity	NPC57674
0.9195	High Similarity	NPC37392
0.9195	High Similarity	NPC20830
0.9195	High Similarity	NPC2928
0.9195	High Similarity	NPC230149
0.9195	High Similarity	NPC168247
0.9195	High Similarity	NPC117992
0.9195	High Similarity	NPC472280
0.9195	High Similarity	NPC472909
0.9195	High Similarity	NPC152951
0.9195	High Similarity	NPC256612
0.9195	High Similarity	NPC226025
0.9189	High Similarity	NPC82325
0.9189	High Similarity	NPC100887
0.9189	High Similarity	NPC120163
0.9189	High Similarity	NPC301323

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 NPC12377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	995
0.2-0.3	1691
0.3-0.4	2651
0.4-0.5	1799
0.5-0.6	1006
0.6-0.7	416
0.7-0.8	103
0.8-0.85	46
0.85-0.9	16
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.932	High Similarity	NPD1934	Approved
0.9281	High Similarity	NPD1510	Phase 2
0.9128	High Similarity	NPD2801	Approved
0.9034	High Similarity	NPD1511	Approved
0.9007	High Similarity	NPD3882	Suspended
0.9	High Similarity	NPD2393	Clinical (unspecified phase)
0.8993	High Similarity	NPD1240	Approved
0.8912	High Similarity	NPD1512	Approved
0.8865	High Similarity	NPD1607	Approved
0.8819	High Similarity	NPD1549	Phase 2
0.8816	High Similarity	NPD3817	Phase 2
0.88	High Similarity	NPD4380	Phase 2
0.875	High Similarity	NPD1550	Clinical (unspecified phase)
0.875	High Similarity	NPD1552	Clinical (unspecified phase)
0.8734	High Similarity	NPD3818	Discontinued
0.8726	High Similarity	NPD6166	Phase 2
0.8726	High Similarity	NPD6168	Clinical (unspecified phase)
0.8726	High Similarity	NPD6167	Clinical (unspecified phase)
0.8716	High Similarity	NPD4378	Clinical (unspecified phase)
0.8681	High Similarity	NPD2796	Approved
0.8599	High Similarity	NPD6232	Discontinued
0.8592	High Similarity	NPD943	Approved
0.8562	High Similarity	NPD7054	Approved
0.8553	High Similarity	NPD7473	Discontinued
0.8509	High Similarity	NPD7472	Approved
0.8509	High Similarity	NPD7074	Phase 3
0.8471	Intermediate Similarity	NPD5494	Approved
0.8467	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8462	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD6799	Approved
0.8397	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD7819	Suspended
0.8355	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7808	Phase 3
0.8344	Intermediate Similarity	NPD6797	Phase 2
0.8323	Intermediate Similarity	NPD6801	Discontinued
0.8293	Intermediate Similarity	NPD7251	Discontinued
0.8291	Intermediate Similarity	NPD919	Approved
0.8258	Intermediate Similarity	NPD7411	Suspended
0.8242	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD3750	Approved
0.82	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6599	Discontinued
0.8187	Intermediate Similarity	NPD1247	Approved
0.8176	Intermediate Similarity	NPD2935	Discontinued
0.811	Intermediate Similarity	NPD5844	Phase 1
0.8086	Intermediate Similarity	NPD3926	Phase 2
0.8054	Intermediate Similarity	NPD1551	Phase 2
0.8038	Intermediate Similarity	NPD1465	Phase 2
0.8027	Intermediate Similarity	NPD230	Phase 1
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7987	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD5401	Approved
0.7987	Intermediate Similarity	NPD5402	Approved
0.7986	Intermediate Similarity	NPD9494	Approved
0.7963	Intermediate Similarity	NPD6959	Discontinued
0.7937	Intermediate Similarity	NPD7768	Phase 2
0.7927	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD447	Suspended
0.7904	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD3749	Approved
0.7871	Intermediate Similarity	NPD2533	Approved
0.7871	Intermediate Similarity	NPD2534	Approved
0.7871	Intermediate Similarity	NPD2532	Approved
0.7867	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD3748	Approved
0.7857	Intermediate Similarity	NPD6559	Discontinued
0.7852	Intermediate Similarity	NPD6651	Approved
0.7838	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1613	Approved
0.7832	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD2798	Approved
0.7785	Intermediate Similarity	NPD1933	Approved
0.7778	Intermediate Similarity	NPD1243	Approved
0.7778	Intermediate Similarity	NPD2800	Approved
0.7771	Intermediate Similarity	NPD920	Approved
0.7763	Intermediate Similarity	NPD2344	Approved
0.7742	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7654	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD37	Approved
0.7636	Intermediate Similarity	NPD7199	Phase 2
0.7603	Intermediate Similarity	NPD1203	Approved
0.7602	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD5536	Phase 2
0.7588	Intermediate Similarity	NPD5953	Discontinued
0.7584	Intermediate Similarity	NPD2313	Discontinued
0.7582	Intermediate Similarity	NPD6100	Approved
0.7582	Intermediate Similarity	NPD6099	Approved
0.758	Intermediate Similarity	NPD7390	Discontinued
0.7569	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2309	Approved
0.7562	Intermediate Similarity	NPD3226	Approved
0.7545	Intermediate Similarity	NPD5242	Approved
0.7545	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1548	Phase 1
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD3018	Phase 2
0.7483	Intermediate Similarity	NPD1470	Approved
0.7471	Intermediate Similarity	NPD7286	Phase 2
0.7468	Intermediate Similarity	NPD4357	Discontinued
0.7453	Intermediate Similarity	NPD7458	Discontinued
0.7452	Intermediate Similarity	NPD6190	Approved
0.745	Intermediate Similarity	NPD6832	Phase 2
0.745	Intermediate Similarity	NPD4908	Phase 1
0.7448	Intermediate Similarity	NPD1201	Approved
0.7448	Intermediate Similarity	NPD1610	Phase 2
0.7436	Intermediate Similarity	NPD2654	Approved
0.7434	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2346	Discontinued
0.7413	Intermediate Similarity	NPD9545	Approved
0.7412	Intermediate Similarity	NPD3751	Discontinued
0.7403	Intermediate Similarity	NPD4308	Phase 3
0.7403	Intermediate Similarity	NPD7033	Discontinued
0.7397	Intermediate Similarity	NPD3972	Approved
0.7397	Intermediate Similarity	NPD9269	Phase 2
0.7397	Intermediate Similarity	NPD9717	Approved
0.7394	Intermediate Similarity	NPD9493	Approved
0.7391	Intermediate Similarity	NPD1653	Approved
0.7389	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6385	Approved
0.7362	Intermediate Similarity	NPD6386	Approved
0.7361	Intermediate Similarity	NPD9268	Approved
0.736	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3268	Approved
0.7351	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2983	Phase 2
0.7347	Intermediate Similarity	NPD2982	Phase 2
0.7341	Intermediate Similarity	NPD7685	Pre-registration
0.7333	Intermediate Similarity	NPD5353	Approved
0.7329	Intermediate Similarity	NPD422	Phase 1
0.7293	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1608	Approved
0.7279	Intermediate Similarity	NPD2981	Phase 2
0.7278	Intermediate Similarity	NPD5710	Approved
0.7278	Intermediate Similarity	NPD5711	Approved
0.7248	Intermediate Similarity	NPD2797	Approved
0.7244	Intermediate Similarity	NPD5404	Approved
0.7244	Intermediate Similarity	NPD5406	Approved
0.7244	Intermediate Similarity	NPD5408	Approved
0.7244	Intermediate Similarity	NPD5405	Approved
0.7237	Intermediate Similarity	NPD411	Approved
0.7237	Intermediate Similarity	NPD3764	Approved
0.7229	Intermediate Similarity	NPD4288	Approved
0.7209	Intermediate Similarity	NPD7228	Approved
0.7205	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5283	Phase 1
0.7182	Intermediate Similarity	NPD4360	Phase 2
0.7182	Intermediate Similarity	NPD4363	Phase 3
0.7181	Intermediate Similarity	NPD1876	Approved
0.7181	Intermediate Similarity	NPD3225	Approved
0.7176	Intermediate Similarity	NPD3787	Discontinued
0.7163	Intermediate Similarity	NPD228	Approved
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7133	Intermediate Similarity	NPD1164	Approved
0.7133	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD3267	Approved
0.7124	Intermediate Similarity	NPD6798	Discontinued
0.7108	Intermediate Similarity	NPD6844	Discontinued
0.7093	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6780	Approved
0.7081	Intermediate Similarity	NPD6776	Approved
0.7081	Intermediate Similarity	NPD6777	Approved
0.7081	Intermediate Similarity	NPD6778	Approved
0.7081	Intermediate Similarity	NPD6781	Approved
0.7081	Intermediate Similarity	NPD6779	Approved
0.7081	Intermediate Similarity	NPD6782	Approved
0.7075	Intermediate Similarity	NPD17	Approved
0.7063	Intermediate Similarity	NPD1241	Discontinued
0.7063	Intermediate Similarity	NPD7003	Approved
0.7062	Intermediate Similarity	NPD8312	Approved
0.7062	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD4625	Phase 3
0.7053	Intermediate Similarity	NPD8151	Discontinued
0.7039	Intermediate Similarity	NPD8150	Discontinued
0.7039	Intermediate Similarity	NPD8434	Phase 2
0.7037	Intermediate Similarity	NPD7584	Approved
0.7034	Intermediate Similarity	NPD405	Clinical (unspecified phase)

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