NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	178.1
Volume:	197.29
LogP:	2.236
LogD:	2.357
LogS:	-2.597
# Rotatable Bonds:	3
TPSA:	18.46
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	1.745
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.524
MDCK Permeability:	1.701523069641553e-05
Pgp-inhibitor:	0.154
Pgp-substrate:	0.975
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.306

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.691
Plasma Protein Binding (PPB):	92.51848602294922%
Volume Distribution (VD):	1.542
Pgp-substrate:	5.314083099365234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.66
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.101
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.17
CYP3A4-substrate:	0.537

ADMET: Excretion

Clearance (CL):	9.139
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.79
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.749
Carcinogencity:	0.354
Eye Corrosion:	0.868
Eye Irritation:	0.964
Respiratory Toxicity:	0.096

Download Data

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

Natural Product: NPC310905

Natural Product ID:	NPC310905
*Common Name:**	Methylisoeugenol
IUPAC Name:	1,2-dimethoxy-4-[(E)-prop-1-enyl]benzene
Synonyms:	Methylisoeugenol
Standard InCHIKey:	NNWHUJCUHAELCL-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4+
SMILES:	C/C=C/c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465829
PubChem CID:	637776
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004113] Methoxybenzenes [CHEMONTID:0004111] Dimethoxybenzenes

*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
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	DOI[10.1016/0045-6535(91)90110-Y]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	roots	n.a.	n.a.	PMID[12444706]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	stem bark	n.a.	n.a.	PMID[20411974]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20476749]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21563811]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21800857]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[21936523]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22671987]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22951040]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23373216]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23713285]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[26296476]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26305406]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[29116780]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2016	Asarum europaeum	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2016	Asarum europaeum	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2016	Asarum europaeum	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31101	Acarus calamus	Species	Acaridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6113	Piper pedicellosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5162	Comaster multifida	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4539	Ipomoea cristulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2016	Asarum europaeum	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO490	Lophozonia menziesii	Species	0thofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7237	Xanthostemon oppositifolius	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5746	Pancratium trianthum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28409	Lens phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7393	Esenbeckia nesiotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8532	Helipterum tenellum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5334	Rhodotypos scandens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2665	Andinobates fulguritus	Species	Dendrobatidae	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	2
MIC	3

Activity Type	# Activity
Cell Line	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[487625]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	400.0	ug.mL-1	PMID[487624]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	400.0	ug.mL-1	PMID[487624]
NPT523	Organism	Malassezia furfur	Malassezia furfur	MIC	=	200.0	ug.mL-1	PMID[487624]

☑ 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 NPC310905 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	406
0.1-0.2	2903
0.2-0.3	9286
0.3-0.4	10025
0.4-0.5	4129
0.5-0.6	9216
0.6-0.7	4825
0.7-0.8	1604
0.8-0.85	209
0.85-0.9	66
0.9-0.95	25
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC12714
0.9792	High Similarity	NPC292792
0.9495	High Similarity	NPC258171
0.9495	High Similarity	NPC227894
0.9307	High Similarity	NPC246358
0.9307	High Similarity	NPC233731
0.9307	High Similarity	NPC7097
0.9307	High Similarity	NPC127326
0.9307	High Similarity	NPC36108
0.9216	High Similarity	NPC137685
0.9216	High Similarity	NPC179309
0.9126	High Similarity	NPC173746
0.9126	High Similarity	NPC8547
0.9126	High Similarity	NPC139617
0.9126	High Similarity	NPC156840
0.9126	High Similarity	NPC257124
0.9126	High Similarity	NPC245552
0.9126	High Similarity	NPC203924
0.9126	High Similarity	NPC78918
0.9126	High Similarity	NPC55300
0.9118	High Similarity	NPC165386
0.9038	High Similarity	NPC165646
0.9029	High Similarity	NPC31279
0.8952	High Similarity	NPC204120
0.8952	High Similarity	NPC165106
0.8952	High Similarity	NPC303522
0.8936	High Similarity	NPC8002
0.8936	High Similarity	NPC259134
0.8936	High Similarity	NPC99886
0.8936	High Similarity	NPC177844
0.8868	High Similarity	NPC294941
0.8842	High Similarity	NPC71853
0.8785	High Similarity	NPC475815
0.8785	High Similarity	NPC473264
0.8785	High Similarity	NPC47194
0.8762	High Similarity	NPC195873
0.875	High Similarity	NPC321956
0.8723	High Similarity	NPC206876
0.8704	High Similarity	NPC81067
0.8704	High Similarity	NPC268317
0.8704	High Similarity	NPC9341
0.8704	High Similarity	NPC221049
0.8704	High Similarity	NPC123948
0.8627	High Similarity	NPC12987
0.8627	High Similarity	NPC474603
0.8624	High Similarity	NPC293619
0.8624	High Similarity	NPC199209
0.8624	High Similarity	NPC212643
0.8624	High Similarity	NPC33271
0.8624	High Similarity	NPC280001
0.8624	High Similarity	NPC304208
0.8624	High Similarity	NPC185738
0.8624	High Similarity	NPC120075
0.8624	High Similarity	NPC52464
0.8624	High Similarity	NPC39793
0.8624	High Similarity	NPC164386
0.8624	High Similarity	NPC259638
0.8571	High Similarity	NPC471581
0.8545	High Similarity	NPC277460
0.8545	High Similarity	NPC137537
0.8545	High Similarity	NPC164706
0.8545	High Similarity	NPC470626
0.8545	High Similarity	NPC255675
0.8545	High Similarity	NPC474040
0.8545	High Similarity	NPC205502
0.8545	High Similarity	NPC124916
0.8545	High Similarity	NPC70744
0.8545	High Similarity	NPC159916
0.8545	High Similarity	NPC474214
0.8545	High Similarity	NPC272471
0.8545	High Similarity	NPC107588
0.8532	High Similarity	NPC111225
0.8532	High Similarity	NPC193067
0.85	High Similarity	NPC175298
0.85	High Similarity	NPC470161
0.8468	Intermediate Similarity	NPC135961
0.8468	Intermediate Similarity	NPC37858
0.8468	Intermediate Similarity	NPC15805
0.8468	Intermediate Similarity	NPC320987
0.8468	Intermediate Similarity	NPC299406
0.8468	Intermediate Similarity	NPC310338
0.8468	Intermediate Similarity	NPC181969
0.8468	Intermediate Similarity	NPC119949
0.8468	Intermediate Similarity	NPC475961
0.8468	Intermediate Similarity	NPC254625
0.8468	Intermediate Similarity	NPC474320
0.8468	Intermediate Similarity	NPC69670
0.8468	Intermediate Similarity	NPC24474
0.8468	Intermediate Similarity	NPC281298
0.8468	Intermediate Similarity	NPC308217
0.8468	Intermediate Similarity	NPC311595
0.8468	Intermediate Similarity	NPC20674
0.8447	Intermediate Similarity	NPC241224
0.8431	Intermediate Similarity	NPC300166
0.8416	Intermediate Similarity	NPC100870
0.8393	Intermediate Similarity	NPC344161
0.8393	Intermediate Similarity	NPC177475
0.8393	Intermediate Similarity	NPC227217
0.8393	Intermediate Similarity	NPC61516
0.8393	Intermediate Similarity	NPC222175
0.8393	Intermediate Similarity	NPC247364
0.8393	Intermediate Similarity	NPC35071
0.8393	Intermediate Similarity	NPC95614
0.8393	Intermediate Similarity	NPC232084
0.8393	Intermediate Similarity	NPC148615
0.8393	Intermediate Similarity	NPC474565
0.8393	Intermediate Similarity	NPC2058
0.8393	Intermediate Similarity	NPC232316
0.8393	Intermediate Similarity	NPC165133
0.8393	Intermediate Similarity	NPC229401
0.8393	Intermediate Similarity	NPC10932
0.8393	Intermediate Similarity	NPC117780
0.8393	Intermediate Similarity	NPC56214
0.8393	Intermediate Similarity	NPC242885
0.8393	Intermediate Similarity	NPC202474
0.8378	Intermediate Similarity	NPC63083
0.8333	Intermediate Similarity	NPC13755
0.8319	Intermediate Similarity	NPC269843
0.8319	Intermediate Similarity	NPC472596
0.8319	Intermediate Similarity	NPC267064
0.8319	Intermediate Similarity	NPC14007
0.8319	Intermediate Similarity	NPC158949
0.8319	Intermediate Similarity	NPC225245
0.8319	Intermediate Similarity	NPC166759
0.8319	Intermediate Similarity	NPC189844
0.8319	Intermediate Similarity	NPC199023
0.8319	Intermediate Similarity	NPC109083
0.8319	Intermediate Similarity	NPC295317
0.8319	Intermediate Similarity	NPC204466
0.8319	Intermediate Similarity	NPC183262
0.8319	Intermediate Similarity	NPC60962
0.8319	Intermediate Similarity	NPC224814
0.8319	Intermediate Similarity	NPC471877
0.8319	Intermediate Similarity	NPC207613
0.8304	Intermediate Similarity	NPC57501
0.8302	Intermediate Similarity	NPC75440
0.8288	Intermediate Similarity	NPC86947
0.8252	Intermediate Similarity	NPC51633
0.8246	Intermediate Similarity	NPC177291
0.8246	Intermediate Similarity	NPC65933
0.8246	Intermediate Similarity	NPC473853
0.8246	Intermediate Similarity	NPC193484
0.8246	Intermediate Similarity	NPC324571
0.8246	Intermediate Similarity	NPC54872
0.8246	Intermediate Similarity	NPC57268
0.8246	Intermediate Similarity	NPC160380
0.8246	Intermediate Similarity	NPC285289
0.8246	Intermediate Similarity	NPC184651
0.8246	Intermediate Similarity	NPC113865
0.8246	Intermediate Similarity	NPC476343
0.8246	Intermediate Similarity	NPC126935
0.8246	Intermediate Similarity	NPC194416
0.8246	Intermediate Similarity	NPC477886
0.8246	Intermediate Similarity	NPC262156
0.8246	Intermediate Similarity	NPC201777
0.8246	Intermediate Similarity	NPC80241
0.8246	Intermediate Similarity	NPC470212
0.8246	Intermediate Similarity	NPC312675
0.8246	Intermediate Similarity	NPC172676
0.8246	Intermediate Similarity	NPC38996
0.8246	Intermediate Similarity	NPC301641
0.8246	Intermediate Similarity	NPC114845
0.8246	Intermediate Similarity	NPC470804
0.8246	Intermediate Similarity	NPC70752
0.8246	Intermediate Similarity	NPC312713
0.8246	Intermediate Similarity	NPC310373
0.8246	Intermediate Similarity	NPC343720
0.8246	Intermediate Similarity	NPC216929
0.8235	Intermediate Similarity	NPC471576
0.8224	Intermediate Similarity	NPC82016
0.8214	Intermediate Similarity	NPC474612
0.8214	Intermediate Similarity	NPC212743
0.819	Intermediate Similarity	NPC288760
0.8174	Intermediate Similarity	NPC298486
0.8174	Intermediate Similarity	NPC114298
0.8174	Intermediate Similarity	NPC41562
0.8174	Intermediate Similarity	NPC30462
0.8174	Intermediate Similarity	NPC473411
0.8174	Intermediate Similarity	NPC288238
0.8174	Intermediate Similarity	NPC286573
0.8174	Intermediate Similarity	NPC261661
0.8174	Intermediate Similarity	NPC71090
0.8174	Intermediate Similarity	NPC209567
0.8174	Intermediate Similarity	NPC194626
0.8174	Intermediate Similarity	NPC71579
0.8174	Intermediate Similarity	NPC262253
0.8174	Intermediate Similarity	NPC270326
0.8174	Intermediate Similarity	NPC85488
0.8174	Intermediate Similarity	NPC256167
0.8173	Intermediate Similarity	NPC179686
0.8173	Intermediate Similarity	NPC192596
0.8173	Intermediate Similarity	NPC298224
0.8173	Intermediate Similarity	NPC12870
0.8173	Intermediate Similarity	NPC24327
0.8173	Intermediate Similarity	NPC305205
0.8155	Intermediate Similarity	NPC107101
0.8148	Intermediate Similarity	NPC475852
0.8142	Intermediate Similarity	NPC226629
0.8119	Intermediate Similarity	NPC107522
0.8103	Intermediate Similarity	NPC140359

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 NPC310905 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	1164
0.2-0.3	1899
0.3-0.4	2577
0.4-0.5	1615
0.5-0.6	950
0.6-0.7	477
0.7-0.8	89
0.8-0.85	7
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9126	High Similarity	NPD228	Approved
0.8952	High Similarity	NPD5283	Phase 1
0.8624	High Similarity	NPD5536	Phase 2
0.8468	Intermediate Similarity	NPD1357	Approved
0.8208	Intermediate Similarity	NPD1358	Approved
0.8174	Intermediate Similarity	NPD2981	Phase 2
0.8131	Intermediate Similarity	NPD2684	Approved
0.8103	Intermediate Similarity	NPD2983	Phase 2
0.8103	Intermediate Similarity	NPD2982	Phase 2
0.8103	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD3705	Approved
0.802	Intermediate Similarity	NPD9296	Approved
0.7944	Intermediate Similarity	NPD3134	Approved
0.787	Intermediate Similarity	NPD290	Approved
0.7838	Intermediate Similarity	NPD7843	Approved
0.7833	Intermediate Similarity	NPD3018	Phase 2
0.7833	Intermediate Similarity	NPD9494	Approved
0.7788	Intermediate Similarity	NPD7157	Approved
0.7769	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD291	Approved
0.7731	Intermediate Similarity	NPD2922	Phase 1
0.7727	Intermediate Similarity	NPD5451	Approved
0.7705	Intermediate Similarity	NPD3027	Phase 3
0.7642	Intermediate Similarity	NPD3145	Approved
0.7642	Intermediate Similarity	NPD5109	Approved
0.7642	Intermediate Similarity	NPD5718	Phase 2
0.7642	Intermediate Similarity	NPD5110	Phase 2
0.7642	Intermediate Similarity	NPD5111	Phase 2
0.7642	Intermediate Similarity	NPD3144	Approved
0.7581	Intermediate Similarity	NPD2674	Phase 3
0.7581	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD9365	Approved
0.7522	Intermediate Similarity	NPD821	Approved
0.7521	Intermediate Similarity	NPD1651	Approved
0.7521	Intermediate Similarity	NPD5691	Approved
0.7475	Intermediate Similarity	NPD111	Approved
0.7458	Intermediate Similarity	NPD4626	Approved
0.7456	Intermediate Similarity	NPD1241	Discontinued
0.7455	Intermediate Similarity	NPD968	Approved
0.7436	Intermediate Similarity	NPD1182	Approved
0.7411	Intermediate Similarity	NPD3021	Approved
0.7411	Intermediate Similarity	NPD3022	Approved
0.7381	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1558	Phase 1
0.7381	Intermediate Similarity	NPD3620	Phase 2
0.7368	Intermediate Similarity	NPD5535	Approved
0.7353	Intermediate Similarity	NPD9295	Approved
0.7344	Intermediate Similarity	NPD6895	Approved
0.7344	Intermediate Similarity	NPD6896	Approved
0.7339	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1281	Approved
0.7328	Intermediate Similarity	NPD6671	Approved
0.7328	Intermediate Similarity	NPD709	Approved
0.7323	Intermediate Similarity	NPD3657	Discovery
0.7287	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2492	Phase 1
0.7266	Intermediate Similarity	NPD2653	Approved
0.7258	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD556	Approved
0.7244	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1613	Approved
0.7231	Intermediate Similarity	NPD2161	Phase 2
0.7231	Intermediate Similarity	NPD3539	Phase 1
0.7227	Intermediate Similarity	NPD5585	Approved
0.7213	Intermediate Similarity	NPD5327	Phase 3
0.7213	Intermediate Similarity	NPD1669	Approved
0.7213	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6111	Discontinued
0.7207	Intermediate Similarity	NPD9697	Approved
0.719	Intermediate Similarity	NPD776	Approved
0.7176	Intermediate Similarity	NPD3540	Phase 1
0.7176	Intermediate Similarity	NPD1375	Discontinued
0.717	Intermediate Similarity	NPD2934	Approved
0.717	Intermediate Similarity	NPD2933	Approved
0.717	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1778	Approved
0.7167	Intermediate Similarity	NPD5846	Approved
0.7167	Intermediate Similarity	NPD6516	Phase 2
0.7167	Intermediate Similarity	NPD2668	Approved
0.7167	Intermediate Similarity	NPD2667	Approved
0.7156	Intermediate Similarity	NPD1242	Phase 1
0.7154	Intermediate Similarity	NPD1283	Approved
0.7131	Intermediate Similarity	NPD1840	Phase 2
0.713	Intermediate Similarity	NPD1139	Approved
0.713	Intermediate Similarity	NPD1137	Approved
0.7121	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2808	Discontinued
0.7121	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7153	Discontinued
0.7119	Intermediate Similarity	NPD3596	Phase 2
0.7107	Intermediate Similarity	NPD3496	Discontinued
0.7103	Intermediate Similarity	NPD2859	Approved
0.7103	Intermediate Similarity	NPD844	Approved
0.7103	Intermediate Similarity	NPD2860	Approved
0.7069	Intermediate Similarity	NPD9379	Approved
0.7069	Intermediate Similarity	NPD9377	Approved
0.7069	Intermediate Similarity	NPD1138	Approved
0.7068	Intermediate Similarity	NPD4236	Phase 3
0.7068	Intermediate Similarity	NPD4162	Approved
0.7068	Intermediate Similarity	NPD3060	Approved
0.7068	Intermediate Similarity	NPD4237	Approved
0.7064	Intermediate Similarity	NPD3020	Approved
0.7054	Intermediate Similarity	NPD447	Suspended
0.704	Intermediate Similarity	NPD4624	Approved
0.704	Intermediate Similarity	NPD6584	Phase 3
0.7037	Intermediate Similarity	NPD288	Approved
0.7025	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD17	Approved
0.7015	Intermediate Similarity	NPD6331	Phase 2
0.7015	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4110	Phase 3
0.7008	Intermediate Similarity	NPD7095	Approved
0.7	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6581	Approved
0.7	Intermediate Similarity	NPD6580	Approved
0.7	Intermediate Similarity	NPD1548	Phase 1
0.6992	Remote Similarity	NPD2233	Approved
0.6992	Remote Similarity	NPD2232	Approved
0.6992	Remote Similarity	NPD2230	Approved
0.6977	Remote Similarity	NPD4060	Phase 1
0.6967	Remote Similarity	NPD3847	Discontinued
0.6963	Remote Similarity	NPD5241	Discontinued
0.6963	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1820	Approved
0.696	Remote Similarity	NPD1818	Approved
0.696	Remote Similarity	NPD1819	Approved
0.696	Remote Similarity	NPD1817	Approved
0.696	Remote Similarity	NPD987	Approved
0.6949	Remote Similarity	NPD595	Approved
0.6949	Remote Similarity	NPD593	Approved
0.6942	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4359	Approved
0.6935	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7124	Phase 2
0.6911	Remote Similarity	NPD1611	Approved
0.6911	Remote Similarity	NPD1610	Phase 2
0.6899	Remote Similarity	NPD3531	Approved
0.6899	Remote Similarity	NPD3530	Approved
0.6899	Remote Similarity	NPD3532	Approved
0.6897	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2557	Approved
0.6885	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8651	Approved
0.688	Remote Similarity	NPD1876	Approved
0.6864	Remote Similarity	NPD594	Approved
0.6864	Remote Similarity	NPD592	Approved
0.6861	Remote Similarity	NPD5297	Approved
0.6861	Remote Similarity	NPD4357	Discontinued
0.6861	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1894	Discontinued
0.6855	Remote Similarity	NPD2231	Phase 2
0.6855	Remote Similarity	NPD2235	Phase 2
0.6855	Remote Similarity	NPD3972	Approved
0.6855	Remote Similarity	NPD1608	Approved
0.6855	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.685	Remote Similarity	NPD2861	Phase 2
0.6847	Remote Similarity	NPD3028	Approved
0.6838	Remote Similarity	NPD2219	Phase 1
0.6838	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1039	Discontinued
0.6815	Remote Similarity	NPD5177	Phase 3
0.6814	Remote Similarity	NPD9501	Approved
0.6812	Remote Similarity	NPD4739	Approved
0.6812	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1424	Approved
0.6812	Remote Similarity	NPD3146	Approved
0.6812	Remote Similarity	NPD4584	Approved
0.6812	Remote Similarity	NPD4123	Phase 3
0.6812	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD9299	Approved
0.6803	Remote Similarity	NPD3445	Approved
0.6803	Remote Similarity	NPD3443	Approved
0.6803	Remote Similarity	NPD3444	Approved
0.68	Remote Similarity	NPD1420	Approved
0.68	Remote Similarity	NPD1421	Approved
0.68	Remote Similarity	NPD6582	Phase 2
0.68	Remote Similarity	NPD6583	Phase 3
0.68	Remote Similarity	NPD3685	Discontinued
0.6794	Remote Similarity	NPD5735	Approved
0.6794	Remote Similarity	NPD1933	Approved
0.6788	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD940	Approved
0.6786	Remote Similarity	NPD846	Approved
0.6777	Remote Similarity	NPD1103	Approved
0.6777	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1102	Approved
0.6774	Remote Similarity	NPD422	Phase 1
0.6774	Remote Similarity	NPD1091	Approved
0.6772	Remote Similarity	NPD3691	Phase 2
0.6772	Remote Similarity	NPD7905	Discontinued
0.6772	Remote Similarity	NPD3690	Phase 2
0.6763	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7526	Approved
0.6763	Remote Similarity	NPD52	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