NPASS Compound

Structure

CID233334 OpenBabel06191716032D 24 27 0 0 0 0 0 0 0 0999 V2000 2.0437 0.8084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3862 -0.4745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8044 1.3719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2084 -1.8834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1913 -2.8133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4116 -1.4037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3775 -3.2635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6084 -1.8414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6124 -2.7599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5978 -1.8539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5807 -2.7838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8047 -1.3774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0109 -1.8412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7992 -1.3873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0112 -2.7745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7873 -3.2410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7980 -0.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7938 -0.4638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8186 -3.2236 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7846 -4.1661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5900 0.0102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5931 -0.0094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0062 0.9182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	321.1
Volume:	325.384
LogP:	3.147
LogD:	2.753
LogS:	-5.041
# Rotatable Bonds:	3
TPSA:	57.65
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	2.458
Fsp3:	0.158
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:	-4.699
MDCK Permeability:	1.8269849533680826e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.265
Plasma Protein Binding (PPB):	91.76740264892578%
Volume Distribution (VD):	0.569
Pgp-substrate:	5.292239189147949%

ADMET: Metabolism

CYP1A2-inhibitor:	0.768
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.793
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.607
CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.781
CYP3A4-inhibitor:	0.615
CYP3A4-substrate:	0.56

ADMET: Excretion

Clearance (CL):	2.101
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.142
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.778
Rat Oral Acute Toxicity:	0.454
Maximum Recommended Daily Dose:	0.194
Skin Sensitization:	0.057
Carcinogencity:	0.724
Eye Corrosion:	0.004
Eye Irritation:	0.324
Respiratory Toxicity:	0.813

Download Data

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

Natural Product: NPC233334

Natural Product ID:	NPC233334
*Common Name:**	Homomoschatoline
IUPAC Name:	n.a.
Synonyms:	Homomoschatoline; O-Methyl-Moschatoline; O-Methylmoschatoline
Standard InCHIKey:	WXGQWNXTPSGPIX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H15NO4/c1-22-17-12-8-9-20-15-13(12)14(18(23-2)19(17)24-3)10-6-4-5-7-11(10)16(15)21/h4-9H,1-3H3
SMILES:	COc1c(OC)c(OC)c2c3c1c1ccccc1C(=O)c3ncc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227533
PubChem CID:	145779
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO16788	Syzygium formosanum	Species	Myrtaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[10075776]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575948]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO7436	Annona foetida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499336]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO32767	guatteria hispida	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[20476748]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158166]
NPO33359	miliusa cf. banacea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158166]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25457	Anemone anhuiensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22452	Leucanthemum vulgare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7436	Annona foetida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25612	Polyalthia microtus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25431	Anthemis cotula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3090	Verbascum undulatum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22545	Plectranthus crassus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25457	Anemone anhuiensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23743	Camoensia maxima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22452	Leucanthemum vulgare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25346	Eucalyptus cneorifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16788	Syzygium formosanum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1222	Baccharis scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3938	Cucurbita pepo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25403	Alstonia villosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1843	Laurelia sempervirens	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6982	Cheimophila salicella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23897	Lobophytum strictum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13861	Niphates rowi	Species	Niphatidae	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
ED50	1
IC50	4
MIC	3
Others	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	8
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1076	Cell Line	B-cells		IC50	>	100000.0	nM	PMID[533958]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[533959]
NPT27	Others	Unspecified		CC50	>	100000.0	nM	PMID[533958]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[533958]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	>	500.0	ug ml-1	PMID[533960]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC50	=	320800.0	nM	PMID[533961]
NPT3631	Organism	Leishmania guyanensis	Leishmania guyanensis	IC50	=	103700.0	nM	PMID[533961]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.5	n.a.	PMID[533962]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	25.0	ug.mL-1	PMID[533962]
NPT2580	Organism	Candida dubliniensis	Candida dubliniensis	MIC	=	12.5	ug.mL-1	PMID[533962]
NPT2580	Organism	Candida dubliniensis	Candida dubliniensis	MIC	=	25.0	ug.mL-1	PMID[533962]

☑ 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 NPC233334 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	578
0.1-0.2	2782
0.2-0.3	11334
0.3-0.4	5705
0.4-0.5	8581
0.5-0.6	11518
0.6-0.7	1856
0.7-0.8	290
0.8-0.85	30
0.85-0.9	2
0.9-0.95	14
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC90875
0.9615	High Similarity	NPC24019
0.9579	High Similarity	NPC15406
0.9535	High Similarity	NPC124313
0.9533	High Similarity	NPC84164
0.9533	High Similarity	NPC207283
0.9515	High Similarity	NPC210434
0.939	High Similarity	NPC108342
0.9346	High Similarity	NPC182907
0.9346	High Similarity	NPC189903
0.9318	High Similarity	NPC183537
0.9231	High Similarity	NPC77878
0.9213	High Similarity	NPC166722
0.9206	High Similarity	NPC22481
0.9155	High Similarity	NPC278525
0.9128	High Similarity	NPC210296
0.9034	High Similarity	NPC236668
0.899	High Similarity	NPC146976
0.8955	High Similarity	NPC119134
0.8619	High Similarity	NPC470020
0.8611	High Similarity	NPC122463
0.8472	Intermediate Similarity	NPC270515
0.8318	Intermediate Similarity	NPC322482
0.8194	Intermediate Similarity	NPC251160
0.8182	Intermediate Similarity	NPC174049
0.8161	Intermediate Similarity	NPC470018
0.8125	Intermediate Similarity	NPC74575
0.8116	Intermediate Similarity	NPC195268
0.8116	Intermediate Similarity	NPC133140
0.8091	Intermediate Similarity	NPC473822
0.807	Intermediate Similarity	NPC253675
0.805	Intermediate Similarity	NPC132385
0.8043	Intermediate Similarity	NPC134637
0.8027	Intermediate Similarity	NPC216612
0.8008	Intermediate Similarity	NPC137353
0.7982	Intermediate Similarity	NPC49547
0.7957	Intermediate Similarity	NPC470017
0.7953	Intermediate Similarity	NPC16452
0.7953	Intermediate Similarity	NPC36229
0.7953	Intermediate Similarity	NPC476581
0.7937	Intermediate Similarity	NPC54066
0.7922	Intermediate Similarity	NPC470022
0.7915	Intermediate Similarity	NPC107123
0.7908	Intermediate Similarity	NPC478045
0.7887	Intermediate Similarity	NPC476578
0.7887	Intermediate Similarity	NPC476582
0.7887	Intermediate Similarity	NPC4071
0.7875	Intermediate Similarity	NPC318068
0.7873	Intermediate Similarity	NPC235076
0.787	Intermediate Similarity	NPC255800
0.787	Intermediate Similarity	NPC96584
0.786	Intermediate Similarity	NPC201508
0.7854	Intermediate Similarity	NPC188420
0.7814	Intermediate Similarity	NPC31930
0.781	Intermediate Similarity	NPC129897
0.7793	Intermediate Similarity	NPC224928
0.7787	Intermediate Similarity	NPC72905
0.7782	Intermediate Similarity	NPC302807
0.7773	Intermediate Similarity	NPC246381
0.7768	Intermediate Similarity	NPC100079
0.7768	Intermediate Similarity	NPC23614
0.7767	Intermediate Similarity	NPC477019
0.7754	Intermediate Similarity	NPC142385
0.7748	Intermediate Similarity	NPC149471
0.7748	Intermediate Similarity	NPC271215
0.7733	Intermediate Similarity	NPC46451
0.7722	Intermediate Similarity	NPC208522
0.7717	Intermediate Similarity	NPC193238
0.7705	Intermediate Similarity	NPC191489
0.7703	Intermediate Similarity	NPC53069
0.7703	Intermediate Similarity	NPC202605
0.7703	Intermediate Similarity	NPC202768
0.7703	Intermediate Similarity	NPC112206
0.7703	Intermediate Similarity	NPC296482
0.7699	Intermediate Similarity	NPC469439
0.7692	Intermediate Similarity	NPC290689
0.7685	Intermediate Similarity	NPC234197
0.7658	Intermediate Similarity	NPC220337
0.7636	Intermediate Similarity	NPC308943
0.7636	Intermediate Similarity	NPC313189
0.7632	Intermediate Similarity	NPC118121
0.7627	Intermediate Similarity	NPC41501
0.7623	Intermediate Similarity	NPC96405
0.7623	Intermediate Similarity	NPC171409
0.7611	Intermediate Similarity	NPC204446
0.7595	Intermediate Similarity	NPC217554
0.7593	Intermediate Similarity	NPC127085
0.7581	Intermediate Similarity	NPC88923
0.7581	Intermediate Similarity	NPC100734
0.7581	Intermediate Similarity	NPC315634
0.7573	Intermediate Similarity	NPC284141
0.7557	Intermediate Similarity	NPC135549
0.7522	Intermediate Similarity	NPC94842
0.7511	Intermediate Similarity	NPC11408
0.7478	Intermediate Similarity	NPC477788
0.7477	Intermediate Similarity	NPC222561
0.7466	Intermediate Similarity	NPC137929
0.7466	Intermediate Similarity	NPC164374
0.7447	Intermediate Similarity	NPC471004
0.7434	Intermediate Similarity	NPC232225
0.741	Intermediate Similarity	NPC470042
0.7404	Intermediate Similarity	NPC476999
0.7401	Intermediate Similarity	NPC55470
0.7382	Intermediate Similarity	NPC473506
0.7379	Intermediate Similarity	NPC284685
0.7368	Intermediate Similarity	NPC13603
0.7362	Intermediate Similarity	NPC469792
0.7361	Intermediate Similarity	NPC141915
0.7361	Intermediate Similarity	NPC280964
0.7361	Intermediate Similarity	NPC114335
0.735	Intermediate Similarity	NPC328186
0.735	Intermediate Similarity	NPC122968
0.735	Intermediate Similarity	NPC477787
0.735	Intermediate Similarity	NPC228377
0.735	Intermediate Similarity	NPC476110
0.735	Intermediate Similarity	NPC475600
0.735	Intermediate Similarity	NPC475631
0.735	Intermediate Similarity	NPC87152
0.7339	Intermediate Similarity	NPC473449
0.7333	Intermediate Similarity	NPC253482
0.7331	Intermediate Similarity	NPC316841
0.7331	Intermediate Similarity	NPC473689
0.7331	Intermediate Similarity	NPC475303
0.7331	Intermediate Similarity	NPC475596
0.7331	Intermediate Similarity	NPC292416
0.7328	Intermediate Similarity	NPC85879
0.7328	Intermediate Similarity	NPC475301
0.7328	Intermediate Similarity	NPC326930
0.7328	Intermediate Similarity	NPC53255
0.7325	Intermediate Similarity	NPC4421
0.7323	Intermediate Similarity	NPC473639
0.7322	Intermediate Similarity	NPC472061
0.732	Intermediate Similarity	NPC282346
0.732	Intermediate Similarity	NPC215837
0.7319	Intermediate Similarity	NPC475644
0.7319	Intermediate Similarity	NPC471190
0.7319	Intermediate Similarity	NPC471977
0.7319	Intermediate Similarity	NPC476997
0.7319	Intermediate Similarity	NPC470486
0.7314	Intermediate Similarity	NPC475648
0.7311	Intermediate Similarity	NPC475406
0.7309	Intermediate Similarity	NPC210256
0.7308	Intermediate Similarity	NPC200888
0.7304	Intermediate Similarity	NPC212768
0.7304	Intermediate Similarity	NPC158020
0.7304	Intermediate Similarity	NPC473115
0.7304	Intermediate Similarity	NPC75600
0.7304	Intermediate Similarity	NPC6576
0.7304	Intermediate Similarity	NPC473089
0.73	Intermediate Similarity	NPC30456
0.73	Intermediate Similarity	NPC320324
0.73	Intermediate Similarity	NPC319880
0.73	Intermediate Similarity	NPC244839
0.7296	Intermediate Similarity	NPC122436
0.7294	Intermediate Similarity	NPC146724
0.7291	Intermediate Similarity	NPC328928
0.7288	Intermediate Similarity	NPC476996
0.7288	Intermediate Similarity	NPC476998
0.728	Intermediate Similarity	NPC473833
0.728	Intermediate Similarity	NPC38959
0.728	Intermediate Similarity	NPC327904
0.7269	Intermediate Similarity	NPC237702
0.725	Intermediate Similarity	NPC235685
0.7249	Intermediate Similarity	NPC298449
0.7246	Intermediate Similarity	NPC476994
0.7238	Intermediate Similarity	NPC327769
0.7231	Intermediate Similarity	NPC148889
0.7224	Intermediate Similarity	NPC1608
0.7222	Intermediate Similarity	NPC250807
0.7222	Intermediate Similarity	NPC76565
0.7222	Intermediate Similarity	NPC57797
0.722	Intermediate Similarity	NPC101350
0.7217	Intermediate Similarity	NPC42678
0.7217	Intermediate Similarity	NPC477909
0.7217	Intermediate Similarity	NPC477907
0.7211	Intermediate Similarity	NPC89549
0.721	Intermediate Similarity	NPC253314
0.721	Intermediate Similarity	NPC477903
0.7206	Intermediate Similarity	NPC67401
0.7205	Intermediate Similarity	NPC162530
0.7203	Intermediate Similarity	NPC146824
0.7198	Intermediate Similarity	NPC84815
0.7198	Intermediate Similarity	NPC301368
0.7193	Intermediate Similarity	NPC208284
0.7191	Intermediate Similarity	NPC328154
0.7191	Intermediate Similarity	NPC475137
0.7191	Intermediate Similarity	NPC475498
0.7191	Intermediate Similarity	NPC473850
0.719	Intermediate Similarity	NPC312872
0.7186	Intermediate Similarity	NPC473513
0.7185	Intermediate Similarity	NPC217176
0.7183	Intermediate Similarity	NPC190461
0.7179	Intermediate Similarity	NPC127026
0.7179	Intermediate Similarity	NPC127720
0.7178	Intermediate Similarity	NPC476995
0.7173	Intermediate Similarity	NPC475362
0.7167	Intermediate Similarity	NPC35208
0.716	Intermediate Similarity	NPC472589
0.7155	Intermediate Similarity	NPC62367
0.7154	Intermediate Similarity	NPC475315

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 NPC233334 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	682
0.2-0.3	952
0.3-0.4	1619
0.4-0.5	2629
0.5-0.6	2178
0.6-0.7	690
0.7-0.8	56
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8116	Intermediate Similarity	NPD3922	Approved
0.8116	Intermediate Similarity	NPD3921	Approved
0.8116	Intermediate Similarity	NPD3924	Approved
0.8116	Intermediate Similarity	NPD3923	Approved
0.8009	Intermediate Similarity	NPD7885	Phase 2
0.8009	Intermediate Similarity	NPD7886	Phase 2
0.7924	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD1483	Discontinued
0.7741	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3763	Approved
0.7705	Intermediate Similarity	NPD7708	Approved
0.7703	Intermediate Similarity	NPD3816	Phase 1
0.7703	Intermediate Similarity	NPD3815	Phase 1
0.7695	Intermediate Similarity	NPD8091	Phase 3
0.7623	Intermediate Similarity	NPD7069	Discontinued
0.7585	Intermediate Similarity	NPD3920	Phase 2
0.7581	Intermediate Similarity	NPD7803	Approved
0.7521	Intermediate Similarity	NPD6790	Phase 1
0.75	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD6494	Phase 2
0.7429	Intermediate Similarity	NPD3386	Phase 2
0.7379	Intermediate Similarity	NPD7955	Approved
0.7379	Intermediate Similarity	NPD7956	Approved
0.7375	Intermediate Similarity	NPD7417	Discontinued
0.7362	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5488	Discontinued
0.7316	Intermediate Similarity	NPD6242	Discontinued
0.7311	Intermediate Similarity	NPD6963	Approved
0.7311	Intermediate Similarity	NPD6964	Approved
0.7304	Intermediate Similarity	NPD6568	Discontinued
0.7304	Intermediate Similarity	NPD7395	Discontinued
0.7256	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4429	Discontinued
0.7193	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD5482	Discontinued
0.7163	Intermediate Similarity	NPD4889	Approved
0.7162	Intermediate Similarity	NPD5866	Approved
0.7143	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4989	Phase 2
0.7112	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5805	Approved
0.7093	Intermediate Similarity	NPD5429	Discontinued
0.7091	Intermediate Similarity	NPD6361	Phase 2
0.7083	Intermediate Similarity	NPD4885	Approved
0.7073	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5022	Discontinued
0.7063	Intermediate Similarity	NPD7169	Suspended
0.7051	Intermediate Similarity	NPD4375	Approved
0.7035	Intermediate Similarity	NPD5513	Phase 2
0.7034	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7426	Phase 1
0.7009	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6531	Approved
0.7008	Intermediate Similarity	NPD6530	Approved
0.7004	Intermediate Similarity	NPD6230	Discontinued
0.7004	Intermediate Similarity	NPD7673	Phase 3
0.7	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6716	Phase 1
0.6985	Remote Similarity	NPD3217	Phase 2
0.6985	Remote Similarity	NPD6745	Discontinued
0.698	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7010	Phase 3
0.6949	Remote Similarity	NPD8479	Phase 2
0.6946	Remote Similarity	NPD3263	Phase 3
0.693	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4952	Phase 3
0.6923	Remote Similarity	NPD8149	Discontinued
0.6913	Remote Similarity	NPD5658	Approved
0.6913	Remote Similarity	NPD7467	Discontinued
0.6905	Remote Similarity	NPD7859	Phase 2
0.6904	Remote Similarity	NPD3925	Approved
0.6903	Remote Similarity	NPD6219	Discontinued
0.69	Remote Similarity	NPD5530	Phase 1
0.6892	Remote Similarity	NPD7588	Discontinued
0.6892	Remote Similarity	NPD6569	Phase 2
0.6888	Remote Similarity	NPD7654	Discontinued
0.6878	Remote Similarity	NPD5930	Phase 3
0.6875	Remote Similarity	NPD6228	Discontinued
0.6875	Remote Similarity	NPD5640	Discontinued
0.6867	Remote Similarity	NPD7225	Discontinued
0.6865	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3354	Phase 2
0.6862	Remote Similarity	NPD7278	Phase 2
0.6862	Remote Similarity	NPD7279	Phase 2
0.6857	Remote Similarity	NPD3006	Discontinued
0.6856	Remote Similarity	NPD4037	Approved
0.6856	Remote Similarity	NPD4122	Approved
0.6856	Remote Similarity	NPD4033	Approved
0.6856	Remote Similarity	NPD4038	Approved
0.6856	Remote Similarity	NPD32	Approved
0.6856	Remote Similarity	NPD4036	Approved
0.6856	Remote Similarity	NPD4035	Approved
0.6856	Remote Similarity	NPD4039	Approved
0.6856	Remote Similarity	NPD31	Approved
0.6856	Remote Similarity	NPD4034	Approved
0.6853	Remote Similarity	NPD5914	Approved
0.6847	Remote Similarity	NPD2334	Discontinued
0.6846	Remote Similarity	NPD3259	Approved
0.6844	Remote Similarity	NPD4373	Phase 2
0.6836	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD5450	Discontinued
0.6833	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.683	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.683	Remote Similarity	NPD4418	Discontinued
0.6802	Remote Similarity	NPD6727	Phase 2
0.6789	Remote Similarity	NPD5891	Approved
0.6786	Remote Similarity	NPD4558	Phase 2
0.6786	Remote Similarity	NPD4551	Phase 2
0.6778	Remote Similarity	NPD4923	Phase 1
0.6776	Remote Similarity	NPD7558	Phase 2
0.6774	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8016	Phase 3
0.6765	Remote Similarity	NPD6974	Phase 3
0.6762	Remote Similarity	NPD6962	Phase 2
0.6761	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD2782	Approved
0.6745	Remote Similarity	NPD2780	Approved
0.6737	Remote Similarity	NPD3257	Approved
0.6737	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6550	Discontinued
0.6724	Remote Similarity	NPD7222	Phase 2
0.6723	Remote Similarity	NPD5632	Approved
0.672	Remote Similarity	NPD4875	Phase 3
0.672	Remote Similarity	NPD4876	Phase 3
0.671	Remote Similarity	NPD4795	Phase 2
0.6708	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7994	Phase 2
0.6708	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3794	Approved
0.6695	Remote Similarity	NPD2899	Discontinued
0.6695	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3795	Approved
0.6694	Remote Similarity	NPD1505	Phase 2
0.6682	Remote Similarity	NPD2781	Approved
0.6681	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4502	Phase 2
0.6681	Remote Similarity	NPD5601	Phase 2
0.6681	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7555	Discontinued
0.668	Remote Similarity	NPD1856	Discontinued
0.668	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6825	Phase 1
0.6654	Remote Similarity	NPD7924	Phase 2
0.6654	Remote Similarity	NPD7925	Phase 2
0.6653	Remote Similarity	NPD6517	Phase 3
0.6652	Remote Similarity	NPD5512	Phase 3
0.6651	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7689	Approved
0.664	Remote Similarity	NPD8468	Phase 2
0.664	Remote Similarity	NPD8100	Phase 3
0.6639	Remote Similarity	NPD4845	Discontinued
0.6639	Remote Similarity	NPD5612	Discontinued
0.6639	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD1038	Approved
0.6637	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3258	Approved
0.6624	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6975	Discontinued
0.6621	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5532	Phase 2
0.6613	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1739	Approved
0.6609	Remote Similarity	NPD1740	Approved
0.6607	Remote Similarity	NPD7291	Discontinued
0.6601	Remote Similarity	NPD4349	Approved
0.6601	Remote Similarity	NPD4350	Approved
0.6598	Remote Similarity	NPD7180	Phase 3
0.6598	Remote Similarity	NPD7674	Phase 3
0.6598	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7675	Phase 3
0.6598	Remote Similarity	NPD5850	Phase 3
0.6597	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD5071	Phase 2
0.6585	Remote Similarity	NPD5479	Discontinued
0.6583	Remote Similarity	NPD6198	Phase 1
0.6579	Remote Similarity	NPD3477	Phase 2
0.6579	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6281	Approved
0.6573	Remote Similarity	NPD7922	Phase 1
0.6571	Remote Similarity	NPD4328	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