NPASS Compound

Structure

CID274327 OpenBabel06191716082D 25 27 0 0 0 0 0 0 0 0999 V2000 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 6 1 0 0 0 0 4 9 2 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 12 2 0 0 0 0 9 12 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 19 2 0 0 0 0 12 25 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	334.655
LogP:	3.307
LogD:	2.478
LogS:	-4.185
# Rotatable Bonds:	4
TPSA:	98.36
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	2.426
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.76
MDCK Permeability:	1.950833757291548e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	85.7050552368164%
Volume Distribution (VD):	0.824
Pgp-substrate:	18.362035751342773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.86
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.577
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.227
CYP2D6-substrate:	0.816
CYP3A4-inhibitor:	0.352
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	2.062
Half-life (T1/2):	0.579

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.548
Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.616
Carcinogencity:	0.203
Eye Corrosion:	0.003
Eye Irritation:	0.235
Respiratory Toxicity:	0.188

Download Data

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

Natural Product: NPC274327

Natural Product ID:	NPC274327
*Common Name:**	Nevadensin
IUPAC Name:	5,7-dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	KRFBMPVGAYGGJE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O7/c1-22-10-6-4-9(5-7-10)12-8-11(19)13-14(20)17(23-2)15(21)18(24-3)16(13)25-12/h4-8,20-21H,1-3H3
SMILES:	COc1ccc(cc1)c1cc(=O)c2c(o1)c(OC)c(c(c2O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL312073
PubChem CID:	160921
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002593] 8-O-methylated flavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	small food enterprises (Zvijezda d.d., Zagreb, Croatia)	n.a.	DOI[10.1002/EJLT.200900231]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO129	Biebersteinia orphanidis	Species	Biebersteiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11198823]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16660462]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	flower petals	n.a.	n.a.	PMID[17480100]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[18303853]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[18303853]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21574561]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775221]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23747095]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[25127164]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25176187]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26696523]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29192771]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[6361218]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Shoot Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10150	Anemone raddeana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16651	Gardenia gummifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13507	Mangifera persiciformis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15424	Aralia chinensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15424	Aralia chinensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16651	Gardenia gummifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8501	Lysimachia congestiflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13507	Mangifera persiciformis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10150	Anemone raddeana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4470	Ocimum americanum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4388	Gloeophyllum odoratum	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7596	Eleutherococcus trifoliatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13507	Mangifera persiciformis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10150	Anemone raddeana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13756	Alpinia conchigera	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8501	Lysimachia congestiflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO129	Biebersteinia orphanidis	Species	Biebersteiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22925	Henriettea fascicularis	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13243	Achillea ligustica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7879	Plagiochila semidecurrens	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14220	Phoracantha semipunctata	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13381	Pannaria fulvescens	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1386	Bothriocline eupatorioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16651	Gardenia gummifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4388	Gloeophyllum odoratum	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4470	Ocimum americanum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13507	Mangifera persiciformis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15547	Jaborosa bergii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15424	Aralia chinensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15099	Machilus parviflora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10150	Anemone raddeana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12728	Artemisia rupestris	Species	Asteraceae	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
GI50	1
IC50	2
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT517	Cell Line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	59000.0	nM	PMID[463171]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5080.0	nM	PMID[463176]
NPT140	Organism	Artemia	Artemia	LC50	>	700.0	ppm	PMID[463172]
NPT2	Others	Unspecified		ID50	=	48.0	ug ml-1	PMID[463173]
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	CD	>	20.0	ug ml-1	PMID[463174]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	7244.36	nM	PMID[463175]

☑ 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 NPC274327 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	480
0.1-0.2	2045
0.2-0.3	5283
0.3-0.4	11455
0.4-0.5	5595
0.5-0.6	4083
0.6-0.7	5142
0.7-0.8	4776
0.8-0.85	1856
0.85-0.9	1104
0.9-0.95	612
0.95-1	266

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC22519
1.0	High Similarity	NPC69394
1.0	High Similarity	NPC231018
1.0	High Similarity	NPC255350
1.0	High Similarity	NPC176775
1.0	High Similarity	NPC145379
1.0	High Similarity	NPC160951
1.0	High Similarity	NPC47781
1.0	High Similarity	NPC183878
0.9932	High Similarity	NPC198826
0.9932	High Similarity	NPC162313
0.9932	High Similarity	NPC131624
0.9932	High Similarity	NPC71334
0.9932	High Similarity	NPC239128
0.9932	High Similarity	NPC213622
0.9932	High Similarity	NPC156222
0.9932	High Similarity	NPC138360
0.9932	High Similarity	NPC187498
0.9932	High Similarity	NPC20830
0.9932	High Similarity	NPC275722
0.9932	High Similarity	NPC4455
0.9932	High Similarity	NPC120163
0.9932	High Similarity	NPC92659
0.9932	High Similarity	NPC83508
0.9932	High Similarity	NPC100887
0.9932	High Similarity	NPC163780
0.9932	High Similarity	NPC183597
0.9932	High Similarity	NPC301323
0.9932	High Similarity	NPC256612
0.9932	High Similarity	NPC188203
0.9932	High Similarity	NPC201136
0.9932	High Similarity	NPC212678
0.9932	High Similarity	NPC275836
0.9932	High Similarity	NPC128863
0.9932	High Similarity	NPC293183
0.9932	High Similarity	NPC50715
0.9932	High Similarity	NPC227325
0.9932	High Similarity	NPC57030
0.9932	High Similarity	NPC222830
0.9932	High Similarity	NPC256283
0.9932	High Similarity	NPC25270
0.9932	High Similarity	NPC2476
0.9932	High Similarity	NPC196439
0.9932	High Similarity	NPC167815
0.9932	High Similarity	NPC280339
0.9932	High Similarity	NPC146165
0.9932	High Similarity	NPC241498
0.9865	High Similarity	NPC49824
0.9864	High Similarity	NPC250822
0.9864	High Similarity	NPC276409
0.9864	High Similarity	NPC75279
0.9863	High Similarity	NPC208043
0.9863	High Similarity	NPC226973
0.9799	High Similarity	NPC75215
0.9799	High Similarity	NPC93376
0.9799	High Similarity	NPC110070
0.9799	High Similarity	NPC227192
0.9799	High Similarity	NPC189179
0.9799	High Similarity	NPC470402
0.9799	High Similarity	NPC203891
0.9799	High Similarity	NPC224137
0.9799	High Similarity	NPC101830
0.9797	High Similarity	NPC44079
0.9797	High Similarity	NPC208197
0.9797	High Similarity	NPC201451
0.9797	High Similarity	NPC26227
0.9796	High Similarity	NPC60972
0.9796	High Similarity	NPC142540
0.9796	High Similarity	NPC39732
0.9795	High Similarity	NPC306821
0.9795	High Similarity	NPC184136
0.9733	High Similarity	NPC19687
0.9733	High Similarity	NPC25495
0.9733	High Similarity	NPC176300
0.9733	High Similarity	NPC261004
0.9733	High Similarity	NPC18772
0.9733	High Similarity	NPC105242
0.9733	High Similarity	NPC130894
0.9733	High Similarity	NPC204854
0.9733	High Similarity	NPC152166
0.9733	High Similarity	NPC115798
0.9733	High Similarity	NPC143828
0.9733	High Similarity	NPC300943
0.9733	High Similarity	NPC9609
0.9733	High Similarity	NPC191459
0.9733	High Similarity	NPC22472
0.9733	High Similarity	NPC18607
0.9733	High Similarity	NPC7846
0.9733	High Similarity	NPC4481
0.9733	High Similarity	NPC253634
0.9733	High Similarity	NPC288669
0.9732	High Similarity	NPC266960
0.9732	High Similarity	NPC98661
0.9732	High Similarity	NPC43243
0.9732	High Similarity	NPC247017
0.9732	High Similarity	NPC472916
0.9732	High Similarity	NPC292107
0.9732	High Similarity	NPC474520
0.9732	High Similarity	NPC245546
0.973	High Similarity	NPC86485
0.9728	High Similarity	NPC308451
0.9726	High Similarity	NPC223579
0.9726	High Similarity	NPC177298
0.9726	High Similarity	NPC328119
0.9726	High Similarity	NPC183950
0.9726	High Similarity	NPC48479
0.9726	High Similarity	NPC296197
0.9726	High Similarity	NPC216318
0.9726	High Similarity	NPC17286
0.9726	High Similarity	NPC259713
0.9726	High Similarity	NPC287101
0.9726	High Similarity	NPC52005
0.9726	High Similarity	NPC137062
0.9669	High Similarity	NPC476980
0.9667	High Similarity	NPC472914
0.9667	High Similarity	NPC176665
0.9667	High Similarity	NPC29841
0.9667	High Similarity	NPC472438
0.9667	High Similarity	NPC48208
0.9667	High Similarity	NPC96167
0.9667	High Similarity	NPC472913
0.9667	High Similarity	NPC475267
0.9667	High Similarity	NPC163524
0.9667	High Similarity	NPC474836
0.9667	High Similarity	NPC472911
0.9667	High Similarity	NPC472910
0.9667	High Similarity	NPC78302
0.9667	High Similarity	NPC235215
0.9667	High Similarity	NPC245758
0.9667	High Similarity	NPC287979
0.9667	High Similarity	NPC474208
0.9667	High Similarity	NPC222814
0.9667	High Similarity	NPC162869
0.9667	High Similarity	NPC78225
0.9667	High Similarity	NPC7973
0.9667	High Similarity	NPC156057
0.9667	High Similarity	NPC305663
0.9664	High Similarity	NPC2928
0.9664	High Similarity	NPC32557
0.9664	High Similarity	NPC189960
0.9662	High Similarity	NPC301123
0.9662	High Similarity	NPC120537
0.9662	High Similarity	NPC180234
0.9662	High Similarity	NPC199100
0.966	High Similarity	NPC45873
0.9658	High Similarity	NPC120464
0.9658	High Similarity	NPC195202
0.9605	High Similarity	NPC258331
0.9603	High Similarity	NPC193842
0.96	High Similarity	NPC200388
0.96	High Similarity	NPC68093
0.96	High Similarity	NPC178854
0.96	High Similarity	NPC191146
0.96	High Similarity	NPC55619
0.96	High Similarity	NPC268161
0.96	High Similarity	NPC100916
0.96	High Similarity	NPC235165
0.96	High Similarity	NPC265511
0.96	High Similarity	NPC255106
0.9597	High Similarity	NPC167091
0.9597	High Similarity	NPC124714
0.9597	High Similarity	NPC271779
0.9597	High Similarity	NPC292214
0.9597	High Similarity	NPC78326
0.9597	High Similarity	NPC270620
0.9597	High Similarity	NPC280937
0.9597	High Similarity	NPC206238
0.9597	High Similarity	NPC472915
0.9597	High Similarity	NPC88645
0.9597	High Similarity	NPC179126
0.9597	High Similarity	NPC236223
0.9595	High Similarity	NPC117579
0.9595	High Similarity	NPC225731
0.9595	High Similarity	NPC200740
0.9595	High Similarity	NPC125062
0.9595	High Similarity	NPC252933
0.9595	High Similarity	NPC54394
0.9592	High Similarity	NPC92722
0.9592	High Similarity	NPC102003
0.9589	High Similarity	NPC33265
0.9589	High Similarity	NPC130230
0.9589	High Similarity	NPC30647
0.9589	High Similarity	NPC61871
0.9589	High Similarity	NPC62536
0.9589	High Similarity	NPC55557
0.9589	High Similarity	NPC275772
0.9589	High Similarity	NPC108406
0.9589	High Similarity	NPC12200
0.9589	High Similarity	NPC239312
0.9542	High Similarity	NPC472448
0.9542	High Similarity	NPC83922
0.9539	High Similarity	NPC246478
0.9539	High Similarity	NPC204290
0.9536	High Similarity	NPC241904
0.9536	High Similarity	NPC476981
0.9536	High Similarity	NPC469584
0.9536	High Similarity	NPC262286
0.9536	High Similarity	NPC36852
0.9536	High Similarity	NPC210084
0.9536	High Similarity	NPC300727

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 NPC274327 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	1006
0.2-0.3	1906
0.3-0.4	2679
0.4-0.5	1673
0.5-0.6	954
0.6-0.7	332
0.7-0.8	96
0.8-0.85	34
0.85-0.9	11
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD2801	Approved
0.94	High Similarity	NPD1934	Approved
0.9384	High Similarity	NPD1511	Approved
0.9257	High Similarity	NPD1512	Approved
0.9216	High Similarity	NPD3882	Suspended
0.9211	High Similarity	NPD2393	Clinical (unspecified phase)
0.9026	High Similarity	NPD3817	Phase 2
0.8938	High Similarity	NPD3818	Discontinued
0.8931	High Similarity	NPD6166	Phase 2
0.8931	High Similarity	NPD6167	Clinical (unspecified phase)
0.8931	High Similarity	NPD6168	Clinical (unspecified phase)
0.8896	High Similarity	NPD4338	Clinical (unspecified phase)
0.8882	High Similarity	NPD7054	Approved
0.8827	High Similarity	NPD7472	Approved
0.8808	High Similarity	NPD4378	Clinical (unspecified phase)
0.8712	High Similarity	NPD7074	Phase 3
0.8679	High Similarity	NPD5494	Approved
0.8659	High Similarity	NPD6797	Phase 2
0.8608	High Similarity	NPD4868	Clinical (unspecified phase)
0.8606	High Similarity	NPD7251	Discontinued
0.8554	High Similarity	NPD7808	Phase 3
0.8526	High Similarity	NPD4380	Phase 2
0.8467	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD6232	Discontinued
0.8456	Intermediate Similarity	NPD1510	Phase 2
0.8438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD5402	Approved
0.8415	Intermediate Similarity	NPD7473	Discontinued
0.8411	Intermediate Similarity	NPD1549	Phase 2
0.84	Intermediate Similarity	NPD2796	Approved
0.8377	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8311	Intermediate Similarity	NPD1240	Approved
0.8311	Intermediate Similarity	NPD943	Approved
0.8282	Intermediate Similarity	NPD1247	Approved
0.825	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD1465	Phase 2
0.8204	Intermediate Similarity	NPD5844	Phase 1
0.82	Intermediate Similarity	NPD1607	Approved
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.817	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7819	Suspended
0.8107	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD3926	Phase 2
0.8063	Intermediate Similarity	NPD6599	Discontinued
0.8041	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8013	Intermediate Similarity	NPD447	Suspended
0.8013	Intermediate Similarity	NPD230	Phase 1
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7987	Intermediate Similarity	NPD5403	Approved
0.7973	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6959	Discontinued
0.7949	Intermediate Similarity	NPD3750	Approved
0.7947	Intermediate Similarity	NPD1613	Approved
0.7947	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD919	Approved
0.7885	Intermediate Similarity	NPD2800	Approved
0.7875	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD3027	Phase 3
0.7862	Intermediate Similarity	NPD5401	Approved
0.7857	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7826	Intermediate Similarity	NPD1653	Approved
0.7815	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1551	Phase 2
0.7771	Intermediate Similarity	NPD3749	Approved
0.775	Intermediate Similarity	NPD2534	Approved
0.775	Intermediate Similarity	NPD2532	Approved
0.775	Intermediate Similarity	NPD2533	Approved
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD9494	Approved
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7768	Phase 2
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6190	Approved
0.7662	Intermediate Similarity	NPD1933	Approved
0.7658	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD920	Approved
0.7643	Intermediate Similarity	NPD2344	Approved
0.7633	Intermediate Similarity	NPD7199	Phase 2
0.7628	Intermediate Similarity	NPD3748	Approved
0.7619	Intermediate Similarity	NPD6234	Discontinued
0.7616	Intermediate Similarity	NPD3751	Discontinued
0.761	Intermediate Similarity	NPD4628	Phase 3
0.7588	Intermediate Similarity	NPD3787	Discontinued
0.7582	Intermediate Similarity	NPD2313	Discontinued
0.758	Intermediate Similarity	NPD6100	Approved
0.758	Intermediate Similarity	NPD6099	Approved
0.7561	Intermediate Similarity	NPD3226	Approved
0.7554	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1243	Approved
0.7544	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7483	Intermediate Similarity	NPD1203	Approved
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7286	Phase 2
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2309	Approved
0.7443	Intermediate Similarity	NPD7685	Pre-registration
0.7425	Intermediate Similarity	NPD37	Approved
0.7425	Intermediate Similarity	NPD6844	Discontinued
0.7421	Intermediate Similarity	NPD2346	Discontinued
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7407	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD9269	Phase 2
0.7396	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7362	Intermediate Similarity	NPD7390	Discontinued
0.7355	Intermediate Similarity	NPD3268	Approved
0.7341	Intermediate Similarity	NPD5242	Approved
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7338	Intermediate Similarity	NPD4908	Phase 1
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2798	Approved
0.7314	Intermediate Similarity	NPD7228	Approved
0.7308	Intermediate Similarity	NPD6233	Phase 2
0.7296	Intermediate Similarity	NPD7033	Discontinued
0.7285	Intermediate Similarity	NPD9717	Approved
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3018	Phase 2
0.7262	Intermediate Similarity	NPD6385	Approved
0.7262	Intermediate Similarity	NPD6386	Approved
0.7256	Intermediate Similarity	NPD4357	Discontinued
0.7255	Intermediate Similarity	NPD2797	Approved
0.7244	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7235	Intermediate Similarity	NPD5353	Approved
0.723	Intermediate Similarity	NPD5536	Phase 2
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2403	Approved
0.719	Intermediate Similarity	NPD3225	Approved
0.7189	Intermediate Similarity	NPD4360	Phase 2
0.7189	Intermediate Similarity	NPD4363	Phase 3
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7184	Intermediate Similarity	NPD5711	Approved
0.7184	Intermediate Similarity	NPD5710	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7171	Intermediate Similarity	NPD1608	Approved
0.7167	Intermediate Similarity	NPD8313	Approved
0.7167	Intermediate Similarity	NPD8312	Approved
0.7161	Intermediate Similarity	NPD2861	Phase 2
0.7134	Intermediate Similarity	NPD6798	Discontinued
0.7134	Intermediate Similarity	NPD411	Approved
0.7133	Intermediate Similarity	NPD9268	Approved
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7117	Intermediate Similarity	NPD1652	Phase 2
0.7111	Intermediate Similarity	NPD7549	Discontinued
0.7108	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7229	Phase 3
0.7085	Intermediate Similarity	NPD2899	Discontinued
0.707	Intermediate Similarity	NPD4625	Phase 3
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7066	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1481	Phase 2
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4361	Phase 2
0.7059	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD228	Approved
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7047	Intermediate Similarity	NPD7584	Approved
0.7035	Intermediate Similarity	NPD4288	Approved
0.7032	Intermediate Similarity	NPD1470	Approved
0.7032	Intermediate Similarity	NPD3267	Approved
0.7032	Intermediate Similarity	NPD3266	Approved
0.7013	Intermediate Similarity	NPD4749	Approved
0.7006	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6994	Remote Similarity	NPD7266	Discontinued
0.6993	Remote Similarity	NPD1535	Discovery
0.6993	Remote Similarity	NPD1201	Approved
0.699	Remote Similarity	NPD7783	Phase 2
0.699	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7697	Approved
0.6979	Remote Similarity	NPD7696	Phase 3

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