NPASS Compound

Structure

CID72370 OpenBabel06191715412D 23 26 0 0 0 0 0 0 0 0999 V2000 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0468 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 4.3776 0.4067 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 5.0468 -2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -0.3364 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 6.0468 -2.0685 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -1.2024 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5468 -2.9345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -0.9945 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 19 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 16 2 0 0 0 0 9 12 1 0 0 0 0 9 18 2 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 17 2 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.1
Volume:	317.024
LogP:	5.308
LogD:	3.945
LogS:	-3.202
# Rotatable Bonds:	1
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.684
Synthetic Accessibility Score:	2.823
Fsp3:	0.158
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:	-4.793
MDCK Permeability:	1.43360739457421e-05
Pgp-inhibitor:	0.166
Pgp-substrate:	0.218
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.598

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	100.34707641601562%
Volume Distribution (VD):	0.895
Pgp-substrate:	0.9841521978378296%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.583
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.751
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.948
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.883
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	6.243
Half-life (T1/2):	0.301

ADMET: Toxicity

hERG Blockers:	0.3
Human Hepatotoxicity (H-HT):	0.474
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.13
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.925
Carcinogencity:	0.694
Eye Corrosion:	0.003
Eye Irritation:	0.738
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC72370

Natural Product ID:	NPC72370
*Common Name:**	Moracin D
IUPAC Name:	7-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethylchromen-5-ol
Synonyms:	Moracin D
Standard InCHIKey:	CHAAQDMHLLQJRO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O4/c1-19(2)6-5-14-15(21)7-12(9-18(14)23-19)16-8-11-3-4-13(20)10-17(11)22-16/h3-10,20-21H,1-2H3
SMILES:	CC1(C)C=Cc2c(cc(cc2O1)c1cc2ccc(cc2o1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463241
PubChem CID:	641378
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO28803	Artocarpus chama	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15165133]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO27320	Morus notabilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21737271]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27478	Geodia japonica	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27320	Morus notabilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27071	Spirastrella coccinea	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27589	Artemisia lehmanniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27280	Stachys spectabilis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27089	Nectandra glabrescens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27147	Habenaria repens	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28584	Euphorbia indica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29149	Zexmenia phyllocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28803	Artocarpus chama	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27368	Sinularia mayi	Species	Alcyoniidae	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	5
MIC	10
Others	2

Activity Type	# Activity
Cell Line	3
Individual Protein	3
Organism	4
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2788	Cell Line	3T3	Mus musculus	Inhibition	=	14.5	%	PMID[25461329]
NPT2954	Individual Protein	Glycerol-3-phosphate dehydrogenase [NAD+], cytoplasmic	Mus musculus	Inhibition	=	12.9	%	PMID[25461329]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	>	40.0	ug.mL-1	PMID[480092]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	12000.0	nM	PMID[480093]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	18000.0	nM	PMID[480093]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	100.0	ug.mL-1	PMID[480093]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[480093]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[480093]
NPT610	Others	Molecular identity unknown		MIC	=	7.0	ug.mL-1	PMID[480093]
NPT610	Others	Molecular identity unknown		MIC	=	28.0	ug.mL-1	PMID[480093]
NPT610	Others	Molecular identity unknown		MIC	=	112.0	ug.mL-1	PMID[480093]
NPT610	Others	Molecular identity unknown		MIC	=	56.0	ug.mL-1	PMID[480093]
NPT2955	Organism	Rosellinia necatrix	Rosellinia necatrix	MIC	<	3.5	ug.mL-1	PMID[480093]
NPT610	Others	Molecular identity unknown		MIC	=	14.0	ug.mL-1	PMID[480093]
NPT2	Others	Unspecified		IC50	=	2540.0	nM	PMID[480093]

☑ 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 NPC72370 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	427
0.1-0.2	1834
0.2-0.3	4255
0.3-0.4	11177
0.4-0.5	6887
0.5-0.6	3837
0.6-0.7	5693
0.7-0.8	4939
0.8-0.85	2267
0.85-0.9	1277
0.9-0.95	96
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC167576
0.973	High Similarity	NPC472462
0.9664	High Similarity	NPC99199
0.9536	High Similarity	NPC268360
0.9527	High Similarity	NPC78335
0.9527	High Similarity	NPC230713
0.947	High Similarity	NPC137100
0.9463	High Similarity	NPC193976
0.9463	High Similarity	NPC170169
0.9463	High Similarity	NPC23668
0.9459	High Similarity	NPC37208
0.9459	High Similarity	NPC221868
0.9459	High Similarity	NPC178202
0.9456	High Similarity	NPC17816
0.9452	High Similarity	NPC155144
0.9408	High Similarity	NPC96342
0.9408	High Similarity	NPC246647
0.9408	High Similarity	NPC164110
0.9408	High Similarity	NPC212967
0.94	High Similarity	NPC142308
0.94	High Similarity	NPC207624
0.9392	High Similarity	NPC272194
0.9355	High Similarity	NPC159508
0.9342	High Similarity	NPC180924
0.9338	High Similarity	NPC235333
0.9333	High Similarity	NPC58668
0.9333	High Similarity	NPC115324
0.9333	High Similarity	NPC106372
0.9329	High Similarity	NPC37226
0.9329	High Similarity	NPC226644
0.932	High Similarity	NPC98926
0.9281	High Similarity	NPC65504
0.9276	High Similarity	NPC297531
0.9276	High Similarity	NPC198490
0.9276	High Similarity	NPC148938
0.9276	High Similarity	NPC213936
0.9257	High Similarity	NPC210826
0.9257	High Similarity	NPC196114
0.9252	High Similarity	NPC302181
0.9221	High Similarity	NPC472877
0.9211	High Similarity	NPC183874
0.9211	High Similarity	NPC1477
0.9211	High Similarity	NPC213608
0.92	High Similarity	NPC474052
0.9195	High Similarity	NPC12148
0.9195	High Similarity	NPC130581
0.9189	High Similarity	NPC230943
0.9184	High Similarity	NPC53192
0.9184	High Similarity	NPC1534
0.9172	High Similarity	NPC169471
0.9145	High Similarity	NPC5871
0.9133	High Similarity	NPC135325
0.9128	High Similarity	NPC300267
0.9128	High Similarity	NPC51641
0.9122	High Similarity	NPC225884
0.9103	High Similarity	NPC45124
0.9103	High Similarity	NPC30655
0.9103	High Similarity	NPC74854
0.9079	High Similarity	NPC258249
0.9073	High Similarity	NPC39929
0.9073	High Similarity	NPC317492
0.9073	High Similarity	NPC10027
0.9073	High Similarity	NPC296030
0.9073	High Similarity	NPC269420
0.9073	High Similarity	NPC65775
0.906	High Similarity	NPC311741
0.906	High Similarity	NPC234629
0.9057	High Similarity	NPC253730
0.9057	High Similarity	NPC286230
0.9045	High Similarity	NPC219861
0.9045	High Similarity	NPC193998
0.9041	High Similarity	NPC112757
0.9038	High Similarity	NPC220582
0.9038	High Similarity	NPC304839
0.9032	High Similarity	NPC260902
0.9032	High Similarity	NPC296957
0.902	High Similarity	NPC142527
0.902	High Similarity	NPC45934
0.902	High Similarity	NPC67654
0.9013	High Similarity	NPC101957
0.9013	High Similarity	NPC120105
0.9013	High Similarity	NPC13282
0.9007	High Similarity	NPC186397
0.9007	High Similarity	NPC37135
0.9007	High Similarity	NPC168085
0.9	High Similarity	NPC99454
0.9	High Similarity	NPC130176
0.9	High Similarity	NPC469758
0.8993	High Similarity	NPC17262
0.8986	High Similarity	NPC118840
0.8986	High Similarity	NPC147688
0.8986	High Similarity	NPC205006
0.8986	High Similarity	NPC64908
0.8986	High Similarity	NPC156590
0.8974	High Similarity	NPC244750
0.8974	High Similarity	NPC40583
0.8973	High Similarity	NPC228661
0.8968	High Similarity	NPC247677
0.8968	High Similarity	NPC160015
0.8968	High Similarity	NPC45131
0.8961	High Similarity	NPC169990
0.8961	High Similarity	NPC122365
0.8961	High Similarity	NPC210942
0.8961	High Similarity	NPC329844
0.8954	High Similarity	NPC149085
0.8954	High Similarity	NPC156244
0.8947	High Similarity	NPC266499
0.8947	High Similarity	NPC223988
0.8947	High Similarity	NPC288036
0.8947	High Similarity	NPC65589
0.8947	High Similarity	NPC97029
0.8947	High Similarity	NPC158338
0.8947	High Similarity	NPC100985
0.8947	High Similarity	NPC97028
0.8944	High Similarity	NPC476641
0.894	High Similarity	NPC150215
0.8933	High Similarity	NPC469764
0.8931	High Similarity	NPC329215
0.8931	High Similarity	NPC136641
0.8931	High Similarity	NPC204088
0.8931	High Similarity	NPC259007
0.8926	High Similarity	NPC169479
0.8926	High Similarity	NPC226636
0.8926	High Similarity	NPC144499
0.8926	High Similarity	NPC159855
0.8926	High Similarity	NPC11561
0.8924	High Similarity	NPC272722
0.8924	High Similarity	NPC312056
0.8924	High Similarity	NPC84515
0.8919	High Similarity	NPC261227
0.8919	High Similarity	NPC171094
0.8919	High Similarity	NPC305355
0.8919	High Similarity	NPC235239
0.8919	High Similarity	NPC475680
0.8919	High Similarity	NPC270883
0.8919	High Similarity	NPC172986
0.8917	High Similarity	NPC260296
0.8917	High Similarity	NPC115432
0.8904	High Similarity	NPC13408
0.8903	High Similarity	NPC275575
0.8896	High Similarity	NPC253872
0.8896	High Similarity	NPC38361
0.8896	High Similarity	NPC227906
0.8896	High Similarity	NPC125300
0.8896	High Similarity	NPC476238
0.8896	High Similarity	NPC263676
0.8896	High Similarity	NPC31627
0.8896	High Similarity	NPC41326
0.8896	High Similarity	NPC327269
0.8896	High Similarity	NPC130015
0.8889	High Similarity	NPC472633
0.8882	High Similarity	NPC27221
0.8882	High Similarity	NPC256672
0.8882	High Similarity	NPC266572
0.8882	High Similarity	NPC7025
0.8875	High Similarity	NPC277480
0.8875	High Similarity	NPC323137
0.8875	High Similarity	NPC53640
0.8874	High Similarity	NPC299011
0.8874	High Similarity	NPC124729
0.8868	High Similarity	NPC155640
0.8868	High Similarity	NPC472581
0.8867	High Similarity	NPC106985
0.8867	High Similarity	NPC190637
0.8867	High Similarity	NPC9117
0.8867	High Similarity	NPC219915
0.8867	High Similarity	NPC293053
0.8867	High Similarity	NPC38219
0.8867	High Similarity	NPC212932
0.8867	High Similarity	NPC166138
0.8867	High Similarity	NPC18585
0.8867	High Similarity	NPC24821
0.8861	High Similarity	NPC188486
0.8859	High Similarity	NPC103362
0.8859	High Similarity	NPC110969
0.8854	High Similarity	NPC196879
0.8854	High Similarity	NPC476349
0.8854	High Similarity	NPC226287
0.8854	High Similarity	NPC476350
0.8854	High Similarity	NPC16935
0.8851	High Similarity	NPC96565
0.8851	High Similarity	NPC216978
0.8851	High Similarity	NPC303633
0.8851	High Similarity	NPC220062
0.8851	High Similarity	NPC55018
0.8851	High Similarity	NPC109232
0.8851	High Similarity	NPC301217
0.8848	High Similarity	NPC121888
0.8846	High Similarity	NPC472461
0.8844	High Similarity	NPC266597
0.8844	High Similarity	NPC250266
0.8839	High Similarity	NPC280530
0.8839	High Similarity	NPC95842
0.8839	High Similarity	NPC178964
0.8839	High Similarity	NPC193200
0.8834	High Similarity	NPC216842
0.8834	High Similarity	NPC476640
0.8834	High Similarity	NPC82217
0.8834	High Similarity	NPC310794
0.8834	High Similarity	NPC65885

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 NPC72370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	981
0.2-0.3	1518
0.3-0.4	2676
0.4-0.5	1897
0.5-0.6	1134
0.6-0.7	367
0.7-0.8	116
0.8-0.85	47
0.85-0.9	16
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8808	High Similarity	NPD7410	Clinical (unspecified phase)
0.8808	High Similarity	NPD4378	Clinical (unspecified phase)
0.879	High Similarity	NPD3749	Approved
0.8618	High Similarity	NPD1511	Approved
0.8599	High Similarity	NPD2801	Approved
0.8591	High Similarity	NPD2344	Approved
0.8581	High Similarity	NPD1510	Phase 2
0.8571	High Similarity	NPD1607	Approved
0.8533	High Similarity	NPD1549	Phase 2
0.8523	High Similarity	NPD2796	Approved
0.8506	High Similarity	NPD1512	Approved
0.8494	Intermediate Similarity	NPD6559	Discontinued
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8481	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1240	Approved
0.8418	Intermediate Similarity	NPD1934	Approved
0.8395	Intermediate Similarity	NPD6959	Discontinued
0.8366	Intermediate Similarity	NPD2309	Approved
0.8364	Intermediate Similarity	NPD3818	Discontinued
0.8355	Intermediate Similarity	NPD1243	Approved
0.8333	Intermediate Similarity	NPD920	Approved
0.8291	Intermediate Similarity	NPD4380	Phase 2
0.825	Intermediate Similarity	NPD7819	Suspended
0.8239	Intermediate Similarity	NPD7411	Suspended
0.8235	Intermediate Similarity	NPD2800	Approved
0.8232	Intermediate Similarity	NPD6232	Discontinued
0.821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2532	Approved
0.8205	Intermediate Similarity	NPD2533	Approved
0.8205	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2534	Approved
0.8199	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD7473	Discontinued
0.8182	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD3926	Phase 2
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.811	Intermediate Similarity	NPD5494	Approved
0.8098	Intermediate Similarity	NPD7075	Discontinued
0.8086	Intermediate Similarity	NPD3817	Phase 2
0.8077	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6599	Discontinued
0.8061	Intermediate Similarity	NPD1247	Approved
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1551	Phase 2
0.8039	Intermediate Similarity	NPD6100	Approved
0.8039	Intermediate Similarity	NPD6099	Approved
0.8037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7768	Phase 2
0.8025	Intermediate Similarity	NPD6799	Approved
0.8025	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3226	Approved
0.7974	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6801	Discontinued
0.7939	Intermediate Similarity	NPD919	Approved
0.7922	Intermediate Similarity	NPD2935	Discontinued
0.7911	Intermediate Similarity	NPD7390	Discontinued
0.7885	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7054	Approved
0.7882	Intermediate Similarity	NPD5844	Phase 1
0.7871	Intermediate Similarity	NPD2346	Discontinued
0.7866	Intermediate Similarity	NPD5402	Approved
0.7857	Intermediate Similarity	NPD3748	Approved
0.7836	Intermediate Similarity	NPD7074	Phase 3
0.7836	Intermediate Similarity	NPD7472	Approved
0.7834	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD943	Approved
0.7815	Intermediate Similarity	NPD2313	Discontinued
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2296	Approved
0.7746	Intermediate Similarity	NPD7251	Discontinued
0.7742	Intermediate Similarity	NPD4308	Phase 3
0.7742	Intermediate Similarity	NPD2799	Discontinued
0.774	Intermediate Similarity	NPD4287	Approved
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7808	Phase 3
0.7701	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5403	Approved
0.7643	Intermediate Similarity	NPD1471	Phase 3
0.764	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4625	Phase 3
0.761	Intermediate Similarity	NPD4628	Phase 3
0.76	Intermediate Similarity	NPD1203	Approved
0.7588	Intermediate Similarity	NPD5711	Approved
0.7588	Intermediate Similarity	NPD5710	Approved
0.7586	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5953	Discontinued
0.7582	Intermediate Similarity	NPD3764	Approved
0.7572	Intermediate Similarity	NPD7286	Phase 2
0.755	Intermediate Similarity	NPD2798	Approved
0.7532	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5401	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7514	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6651	Approved
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD5761	Phase 2
0.7485	Intermediate Similarity	NPD5760	Phase 2
0.7484	Intermediate Similarity	NPD4307	Phase 2
0.7468	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD3268	Approved
0.7468	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD5404	Approved
0.7468	Intermediate Similarity	NPD5408	Approved
0.7468	Intermediate Similarity	NPD411	Approved
0.7467	Intermediate Similarity	NPD4749	Approved
0.7451	Intermediate Similarity	NPD4908	Phase 1
0.7436	Intermediate Similarity	NPD447	Suspended
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7425	Intermediate Similarity	NPD6279	Approved
0.7425	Intermediate Similarity	NPD6280	Approved
0.74	Intermediate Similarity	NPD9717	Approved
0.7368	Intermediate Similarity	NPD1470	Approved
0.7368	Intermediate Similarity	NPD2797	Approved
0.7363	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7333	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2654	Approved
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.7297	Intermediate Similarity	NPD1548	Phase 1
0.7296	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1608	Approved
0.7285	Intermediate Similarity	NPD3972	Approved
0.7283	Intermediate Similarity	NPD6808	Phase 2
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7253	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4361	Phase 2
0.7243	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4288	Approved
0.7232	Intermediate Similarity	NPD1729	Discontinued
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7219	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD6844	Discontinued
0.72	Intermediate Similarity	NPD2403	Approved
0.719	Intermediate Similarity	NPD3225	Approved
0.7189	Intermediate Similarity	NPD4360	Phase 2
0.7189	Intermediate Similarity	NPD4363	Phase 3
0.7184	Intermediate Similarity	NPD3787	Discontinued
0.7178	Intermediate Similarity	NPD7003	Approved
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.7151	Intermediate Similarity	NPD6971	Discontinued
0.7151	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7177	Discontinued
0.7119	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD37	Approved
0.7112	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6234	Discontinued
0.7095	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4965	Approved
0.7093	Intermediate Similarity	NPD4966	Approved
0.7093	Intermediate Similarity	NPD4967	Phase 2
0.709	Intermediate Similarity	NPD6779	Approved
0.709	Intermediate Similarity	NPD6781	Approved
0.709	Intermediate Similarity	NPD6782	Approved
0.709	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6780	Approved
0.709	Intermediate Similarity	NPD6778	Approved
0.709	Intermediate Similarity	NPD6777	Approved
0.709	Intermediate Similarity	NPD6776	Approved
0.7088	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD17	Approved
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2861	Phase 2
0.7041	Intermediate Similarity	NPD7458	Discontinued
0.7035	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.7025	Intermediate Similarity	NPD1296	Phase 2
0.7006	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5124	Phase 1
0.7	Intermediate Similarity	NPD1933	Approved
0.7	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7783	Phase 2
0.699	Remote Similarity	NPD7782	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