NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.11
Volume:	276.095
LogP:	3.243
LogD:	3.465
LogS:	-3.015
# Rotatable Bonds:	4
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.881
Synthetic Accessibility Score:	2.125
Fsp3:	0.125
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:	-4.724
MDCK Permeability:	1.8069993529934436e-05
Pgp-inhibitor:	0.132
Pgp-substrate:	0.081
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	97.61827850341797%
Volume Distribution (VD):	1.14
Pgp-substrate:	1.7695722579956055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.707
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.877
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	14.192
Half-life (T1/2):	0.919

ADMET: Toxicity

hERG Blockers:	0.183
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.463
Skin Sensitization:	0.95
Carcinogencity:	0.508
Eye Corrosion:	0.053
Eye Irritation:	0.953
Respiratory Toxicity:	0.677

Download Data

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

Natural Product: NPC185541

Natural Product ID:	NPC185541
*Common Name:**	Xenognosin
IUPAC Name:	4-[(E)-3-(4-hydroxyphenyl)prop-2-enyl]-3-methoxyphenol
Synonyms:	Xenognosin
Standard InCHIKey:	LOHIEGDVOARVPJ-NSCUHMNNSA-N
Standard InCHI:	InChI=1S/C16H16O3/c1-19-16-11-15(18)10-7-13(16)4-2-3-12-5-8-14(17)9-6-12/h2-3,5-11,17-18H,4H2,1H3/b3-2+
SMILES:	COc1cc(O)ccc1C/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087026
PubChem CID:	5281296
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12568545]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15286289]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19128011]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191562]
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[20947202]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253552]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28093914]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Wax	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13749	Luvunga scandens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13749	Luvunga scandens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22420	Lignum dalbergiae odoriferae rosewood	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13749	Luvunga scandens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	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	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	5.7	uM	PMID[458297]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	0.01	uM	PMID[458297]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[458297]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[458297]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	0.7	uM	PMID[458297]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	4.6	uM	PMID[458297]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.1	uM	PMID[458297]

☑ 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 NPC185541 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	303
0.1-0.2	1829
0.2-0.3	5672
0.3-0.4	13566
0.4-0.5	3761
0.5-0.6	5088
0.6-0.7	7772
0.7-0.8	3787
0.8-0.85	611
0.85-0.9	235
0.9-0.95	67
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC464
0.9907	High Similarity	NPC54507
0.9907	High Similarity	NPC85292
0.9907	High Similarity	NPC229147
0.9727	High Similarity	NPC131118
0.9469	High Similarity	NPC102639
0.9459	High Similarity	NPC69261
0.9459	High Similarity	NPC33270
0.9459	High Similarity	NPC474933
0.9386	High Similarity	NPC476633
0.9369	High Similarity	NPC150624
0.9369	High Similarity	NPC141090
0.9369	High Similarity	NPC203113
0.9364	High Similarity	NPC180508
0.9364	High Similarity	NPC228287
0.9304	High Similarity	NPC100099
0.9304	High Similarity	NPC36016
0.9292	High Similarity	NPC184302
0.9292	High Similarity	NPC295259
0.9279	High Similarity	NPC53906
0.9279	High Similarity	NPC808
0.9224	High Similarity	NPC76465
0.9224	High Similarity	NPC38761
0.9224	High Similarity	NPC474160
0.9217	High Similarity	NPC54972
0.9204	High Similarity	NPC190514
0.9204	High Similarity	NPC74821
0.9189	High Similarity	NPC22610
0.9189	High Similarity	NPC276737
0.9182	High Similarity	NPC280606
0.9145	High Similarity	NPC106914
0.9145	High Similarity	NPC246648
0.9145	High Similarity	NPC197351
0.9145	High Similarity	NPC86502
0.9145	High Similarity	NPC134195
0.9115	High Similarity	NPC470759
0.9115	High Similarity	NPC50521
0.9115	High Similarity	NPC221549
0.9115	High Similarity	NPC244816
0.9115	High Similarity	NPC127894
0.9115	High Similarity	NPC15860
0.9115	High Similarity	NPC219070
0.9115	High Similarity	NPC195466
0.9091	High Similarity	NPC296920
0.9091	High Similarity	NPC90520
0.9068	High Similarity	NPC105031
0.9068	High Similarity	NPC105925
0.9068	High Similarity	NPC113495
0.9068	High Similarity	NPC103420
0.9068	High Similarity	NPC17809
0.9068	High Similarity	NPC102540
0.9068	High Similarity	NPC60885
0.9068	High Similarity	NPC188022
0.9068	High Similarity	NPC234400
0.9068	High Similarity	NPC285040
0.9043	High Similarity	NPC258979
0.9043	High Similarity	NPC93398
0.9043	High Similarity	NPC8283
0.9027	High Similarity	NPC114064
0.9	High Similarity	NPC94045
0.8992	High Similarity	NPC283049
0.8992	High Similarity	NPC18924
0.8992	High Similarity	NPC103823
0.8992	High Similarity	NPC50315
0.8992	High Similarity	NPC44748
0.8992	High Similarity	NPC78974
0.8992	High Similarity	NPC26879
0.8992	High Similarity	NPC28730
0.8992	High Similarity	NPC223136
0.8992	High Similarity	NPC276212
0.8992	High Similarity	NPC170485
0.8992	High Similarity	NPC214406
0.8992	High Similarity	NPC230479
0.8983	High Similarity	NPC270030
0.8981	High Similarity	NPC113457
0.8974	High Similarity	NPC77789
0.8974	High Similarity	NPC18128
0.8938	High Similarity	NPC167934
0.8917	High Similarity	NPC169474
0.8917	High Similarity	NPC293054
0.8917	High Similarity	NPC82679
0.8917	High Similarity	NPC246620
0.8917	High Similarity	NPC124452
0.8917	High Similarity	NPC324112
0.8917	High Similarity	NPC159968
0.8917	High Similarity	NPC282000
0.8917	High Similarity	NPC149796
0.8917	High Similarity	NPC236791
0.8917	High Similarity	NPC473221
0.8917	High Similarity	NPC74817
0.8909	High Similarity	NPC82016
0.8908	High Similarity	NPC299584
0.8908	High Similarity	NPC265483
0.8908	High Similarity	NPC82483
0.8898	High Similarity	NPC136319
0.8898	High Similarity	NPC233526
0.8898	High Similarity	NPC282496
0.8889	High Similarity	NPC193364
0.8889	High Similarity	NPC75713
0.8889	High Similarity	NPC474839
0.8843	High Similarity	NPC274717
0.8843	High Similarity	NPC53986
0.8843	High Similarity	NPC222572
0.8843	High Similarity	NPC38664
0.8843	High Similarity	NPC87224
0.8833	High Similarity	NPC82299
0.8833	High Similarity	NPC223953
0.8829	High Similarity	NPC2682
0.8829	High Similarity	NPC168657
0.8824	High Similarity	NPC138248
0.8824	High Similarity	NPC159132
0.8824	High Similarity	NPC228503
0.8818	High Similarity	NPC61885
0.8818	High Similarity	NPC63698
0.8814	High Similarity	NPC74137
0.8803	High Similarity	NPC166759
0.8796	High Similarity	NPC119860
0.8793	High Similarity	NPC59561
0.8793	High Similarity	NPC172253
0.877	High Similarity	NPC93962
0.877	High Similarity	NPC190144
0.877	High Similarity	NPC471518
0.877	High Similarity	NPC10225
0.877	High Similarity	NPC58164
0.877	High Similarity	NPC134360
0.877	High Similarity	NPC471519
0.8761	High Similarity	NPC141003
0.8761	High Similarity	NPC35344
0.876	High Similarity	NPC46978
0.875	High Similarity	NPC233410
0.875	High Similarity	NPC278955
0.875	High Similarity	NPC105718
0.875	High Similarity	NPC203133
0.875	High Similarity	NPC193544
0.875	High Similarity	NPC117214
0.875	High Similarity	NPC208950
0.875	High Similarity	NPC298757
0.875	High Similarity	NPC116907
0.875	High Similarity	NPC221077
0.875	High Similarity	NPC472093
0.875	High Similarity	NPC57490
0.875	High Similarity	NPC251855
0.875	High Similarity	NPC17943
0.875	High Similarity	NPC475169
0.8739	High Similarity	NPC95168
0.8729	High Similarity	NPC97432
0.8729	High Similarity	NPC190454
0.8727	High Similarity	NPC35543
0.8718	High Similarity	NPC474565
0.8699	High Similarity	NPC224157
0.8699	High Similarity	NPC234488
0.8699	High Similarity	NPC51840
0.8699	High Similarity	NPC299221
0.8699	High Similarity	NPC126836
0.8699	High Similarity	NPC469929
0.8699	High Similarity	NPC192687
0.8699	High Similarity	NPC254000
0.8699	High Similarity	NPC311680
0.8689	High Similarity	NPC47283
0.8689	High Similarity	NPC28765
0.8689	High Similarity	NPC39064
0.8689	High Similarity	NPC154866
0.8689	High Similarity	NPC215300
0.8689	High Similarity	NPC219923
0.8661	High Similarity	NPC475018
0.8661	High Similarity	NPC106141
0.8655	High Similarity	NPC41562
0.8655	High Similarity	NPC71579
0.8655	High Similarity	NPC262253
0.8655	High Similarity	NPC473411
0.8649	High Similarity	NPC201959
0.8649	High Similarity	NPC75440
0.8649	High Similarity	NPC245115
0.8644	High Similarity	NPC218753
0.8636	High Similarity	NPC164576
0.8632	High Similarity	NPC137294
0.8632	High Similarity	NPC226629
0.8632	High Similarity	NPC85895
0.8629	High Similarity	NPC228369
0.8629	High Similarity	NPC129106
0.8629	High Similarity	NPC244888
0.8629	High Similarity	NPC164574
0.8629	High Similarity	NPC268917
0.8629	High Similarity	NPC471517
0.8629	High Similarity	NPC206224
0.8629	High Similarity	NPC118683
0.8629	High Similarity	NPC12875
0.8629	High Similarity	NPC118114
0.8629	High Similarity	NPC473309
0.8629	High Similarity	NPC293203
0.8629	High Similarity	NPC162801
0.8629	High Similarity	NPC196765
0.8629	High Similarity	NPC164804
0.8629	High Similarity	NPC103799
0.8629	High Similarity	NPC236014
0.8629	High Similarity	NPC129784
0.8629	High Similarity	NPC150011
0.8629	High Similarity	NPC300875
0.8629	High Similarity	NPC12275
0.8629	High Similarity	NPC15543

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 NPC185541 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	1065
0.2-0.3	1532
0.3-0.4	2706
0.4-0.5	1759
0.5-0.6	1012
0.6-0.7	621
0.7-0.8	128
0.8-0.85	14
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9204	High Similarity	NPD1548	Phase 1
0.8889	High Similarity	NPD1610	Phase 2
0.8843	High Similarity	NPD4908	Phase 1
0.8699	High Similarity	NPD4907	Clinical (unspecified phase)
0.8611	High Similarity	NPD940	Approved
0.8611	High Similarity	NPD846	Approved
0.8571	High Similarity	NPD422	Phase 1
0.8468	Intermediate Similarity	NPD3027	Phase 3
0.84	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.832	Intermediate Similarity	NPD4625	Phase 3
0.8279	Intermediate Similarity	NPD4749	Approved
0.8268	Intermediate Similarity	NPD1240	Approved
0.824	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD2933	Approved
0.8224	Intermediate Similarity	NPD2934	Approved
0.8182	Intermediate Similarity	NPD1242	Phase 1
0.816	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD3018	Phase 2
0.8148	Intermediate Similarity	NPD2859	Approved
0.8148	Intermediate Similarity	NPD2860	Approved
0.814	Intermediate Similarity	NPD1607	Approved
0.8125	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1613	Approved
0.808	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8016	Intermediate Similarity	NPD2861	Phase 2
0.7984	Intermediate Similarity	NPD2982	Phase 2
0.7984	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD2983	Phase 2
0.7982	Intermediate Similarity	NPD968	Approved
0.7969	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD5451	Approved
0.7931	Intermediate Similarity	NPD4750	Phase 3
0.7928	Intermediate Similarity	NPD3020	Approved
0.7903	Intermediate Similarity	NPD2981	Phase 2
0.7879	Intermediate Similarity	NPD1510	Phase 2
0.7845	Intermediate Similarity	NPD2684	Approved
0.7833	Intermediate Similarity	NPD6671	Approved
0.781	Intermediate Similarity	NPD7213	Phase 3
0.781	Intermediate Similarity	NPD7212	Phase 2
0.7797	Intermediate Similarity	NPD228	Approved
0.7761	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD290	Approved
0.7754	Intermediate Similarity	NPD7447	Phase 1
0.7754	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD1549	Phase 2
0.7698	Intermediate Similarity	NPD6582	Phase 2
0.7698	Intermediate Similarity	NPD6583	Phase 3
0.768	Intermediate Similarity	NPD1091	Approved
0.7667	Intermediate Similarity	NPD5283	Phase 1
0.7652	Intermediate Similarity	NPD5124	Phase 1
0.7652	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3847	Discontinued
0.7591	Intermediate Similarity	NPD3750	Approved
0.7583	Intermediate Similarity	NPD7843	Approved
0.7583	Intermediate Similarity	NPD821	Approved
0.7583	Intermediate Similarity	NPD5535	Approved
0.7578	Intermediate Similarity	NPD2797	Approved
0.7556	Intermediate Similarity	NPD6100	Approved
0.7556	Intermediate Similarity	NPD6099	Approved
0.7556	Intermediate Similarity	NPD2796	Approved
0.752	Intermediate Similarity	NPD4626	Approved
0.752	Intermediate Similarity	NPD2668	Approved
0.752	Intermediate Similarity	NPD2667	Approved
0.7519	Intermediate Similarity	NPD6584	Phase 3
0.75	Intermediate Similarity	NPD3540	Phase 1
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3225	Approved
0.7463	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2238	Phase 2
0.7444	Intermediate Similarity	NPD4060	Phase 1
0.7429	Intermediate Similarity	NPD6799	Approved
0.7426	Intermediate Similarity	NPD1551	Phase 2
0.7426	Intermediate Similarity	NPD3539	Phase 1
0.7426	Intermediate Similarity	NPD2935	Discontinued
0.7422	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD709	Approved
0.7398	Intermediate Similarity	NPD7157	Approved
0.7398	Intermediate Similarity	NPD2557	Approved
0.7391	Intermediate Similarity	NPD1652	Phase 2
0.7383	Intermediate Similarity	NPD111	Approved
0.7381	Intermediate Similarity	NPD6516	Phase 2
0.7381	Intermediate Similarity	NPD5846	Approved
0.7373	Intermediate Similarity	NPD3134	Approved
0.7364	Intermediate Similarity	NPD8651	Approved
0.7361	Intermediate Similarity	NPD4380	Phase 2
0.736	Intermediate Similarity	NPD1894	Discontinued
0.7353	Intermediate Similarity	NPD7033	Discontinued
0.7345	Intermediate Similarity	NPD844	Approved
0.7345	Intermediate Similarity	NPD1809	Phase 2
0.7344	Intermediate Similarity	NPD2232	Approved
0.7344	Intermediate Similarity	NPD2233	Approved
0.7344	Intermediate Similarity	NPD2230	Approved
0.7339	Intermediate Similarity	NPD3596	Phase 2
0.7338	Intermediate Similarity	NPD3892	Phase 2
0.7338	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7466	Approved
0.7333	Intermediate Similarity	NPD3054	Approved
0.7333	Intermediate Similarity	NPD3052	Approved
0.7333	Intermediate Similarity	NPD4097	Suspended
0.7333	Intermediate Similarity	NPD3022	Approved
0.7333	Intermediate Similarity	NPD3021	Approved
0.7329	Intermediate Similarity	NPD2801	Approved
0.7329	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD845	Approved
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7411	Suspended
0.7305	Intermediate Similarity	NPD1511	Approved
0.7293	Intermediate Similarity	NPD3268	Approved
0.7293	Intermediate Similarity	NPD6798	Discontinued
0.7279	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9295	Approved
0.7266	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1535	Discovery
0.7266	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1934	Approved
0.7258	Intermediate Similarity	NPD6387	Discontinued
0.7252	Intermediate Similarity	NPD3690	Phase 2
0.7252	Intermediate Similarity	NPD3691	Phase 2
0.7244	Intermediate Similarity	NPD1778	Approved
0.7241	Intermediate Similarity	NPD3028	Approved
0.7231	Intermediate Similarity	NPD6696	Suspended
0.723	Intermediate Similarity	NPD7768	Phase 2
0.723	Intermediate Similarity	NPD3882	Suspended
0.7226	Intermediate Similarity	NPD3748	Approved
0.7222	Intermediate Similarity	NPD6580	Approved
0.7222	Intermediate Similarity	NPD6581	Approved
0.7214	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1481	Phase 2
0.7209	Intermediate Similarity	NPD1608	Approved
0.7206	Intermediate Similarity	NPD6651	Approved
0.7203	Intermediate Similarity	NPD1512	Approved
0.7188	Intermediate Similarity	NPD3496	Discontinued
0.7185	Intermediate Similarity	NPD1558	Phase 1
0.7183	Intermediate Similarity	NPD4357	Discontinued
0.7181	Intermediate Similarity	NPD7075	Discontinued
0.7176	Intermediate Similarity	NPD1203	Approved
0.7167	Intermediate Similarity	NPD1358	Approved
0.7165	Intermediate Similarity	NPD3049	Approved
0.7165	Intermediate Similarity	NPD3444	Approved
0.7165	Intermediate Similarity	NPD1651	Approved
0.7165	Intermediate Similarity	NPD3443	Approved
0.7165	Intermediate Similarity	NPD5691	Approved
0.7165	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD3445	Approved
0.7164	Intermediate Similarity	NPD1296	Phase 2
0.7154	Intermediate Similarity	NPD1138	Approved
0.7154	Intermediate Similarity	NPD1669	Approved
0.7153	Intermediate Similarity	NPD4536	Approved
0.7153	Intermediate Similarity	NPD2200	Suspended
0.7153	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4538	Approved
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7132	Intermediate Similarity	NPD6355	Discontinued
0.7132	Intermediate Similarity	NPD4340	Discontinued
0.713	Intermediate Similarity	NPD288	Approved
0.7123	Intermediate Similarity	NPD6599	Discontinued
0.7121	Intermediate Similarity	NPD4624	Approved
0.7113	Intermediate Similarity	NPD6667	Approved
0.7113	Intermediate Similarity	NPD6666	Approved
0.7111	Intermediate Similarity	NPD6233	Phase 2
0.7109	Intermediate Similarity	NPD2556	Approved
0.7109	Intermediate Similarity	NPD2554	Approved
0.7109	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9089	Approved
0.7099	Intermediate Similarity	NPD1283	Approved
0.7097	Intermediate Similarity	NPD1241	Discontinued
0.7095	Intermediate Similarity	NPD7819	Suspended
0.7095	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5163	Phase 2
0.7087	Intermediate Similarity	NPD9545	Approved
0.7087	Intermediate Similarity	NPD2486	Discontinued
0.7077	Intermediate Similarity	NPD3972	Approved
0.7077	Intermediate Similarity	NPD2231	Phase 2
0.7077	Intermediate Similarity	NPD2235	Phase 2
0.7073	Intermediate Similarity	NPD1139	Approved
0.7073	Intermediate Similarity	NPD1137	Approved
0.7067	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9493	Approved
0.7042	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5403	Approved
0.7031	Intermediate Similarity	NPD1357	Approved
0.7029	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD37	Approved
0.7027	Intermediate Similarity	NPD6801	Discontinued
0.7023	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD3685	Discontinued
0.7021	Intermediate Similarity	NPD3060	Approved
0.7016	Intermediate Similarity	NPD7635	Approved
0.7015	Intermediate Similarity	NPD596	Approved
0.7015	Intermediate Similarity	NPD6832	Phase 2
0.7015	Intermediate Similarity	NPD600	Approved
0.7009	Intermediate Similarity	NPD9093	Approved
0.7007	Intermediate Similarity	NPD4675	Approved
0.7007	Intermediate Similarity	NPD4678	Approved

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