NPASS Compound

Structure

CID137062 OpenBabel06191715492D 23 25 0 0 0 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -1.5000 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 1.7321 -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 2.5981 0.5000 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 1.7321 2.0000 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 -3.4641 0.0000 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 -4.3301 -1.5000 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 0.0000 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 0.5000 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 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 15 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 7 16 2 0 0 0 0 8 13 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 21 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	3.574
LogD:	2.835
LogS:	-3.856
# Rotatable Bonds:	3
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	2.252
Fsp3:	0.118
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:	-4.861
MDCK Permeability:	1.5552514014416374e-05
Pgp-inhibitor:	0.064
Pgp-substrate:	0.544
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	93.166259765625%
Volume Distribution (VD):	0.692
Pgp-substrate:	8.731134414672852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.727
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.739
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.645
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.696
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	6.251
Half-life (T1/2):	0.701

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.891
AMES Toxicity:	0.533
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.68
Skin Sensitization:	0.804
Carcinogencity:	0.064
Eye Corrosion:	0.006
Eye Irritation:	0.921
Respiratory Toxicity:	0.557

Download Data

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

Natural Product: NPC137062

Natural Product ID:	NPC137062
*Common Name:**	Velutin
IUPAC Name:	5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one
Synonyms:	Velutin
Standard InCHIKey:	ROCUOVBWAWAQFD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-21-10-6-12(19)17-13(20)8-14(23-16(17)7-10)9-3-4-11(18)15(5-9)22-2/h3-8,18-19H,1-2H3
SMILES:	COc1cc(O)c2c(c1)oc(cc2=O)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508292
PubChem CID:	5464381
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-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
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075750]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608862]
NPO10810	Acridocarpus vivy	Species	Malpighiaceae	Eukaryota	n.a.	Madagascar rain forest	n.a.	PMID[15217279]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15678383]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16045947]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711344]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	stem bark	Kunming, Yunnan Province, China	n.a.	PMID[18986199]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19025748]
NPO1905	Fagraea fragrans	Species	Gentianaceae	Eukaryota	bark and leaves	Koh Kong Province, Cambodia	2005-DEC	PMID[19053508]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245240]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO6706	Arthrobotrys oligospora	Species	Orbiliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21568306]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	flower	n.a.	PMID[21916433]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22351977]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[23558238]
NPO32859	leucas stelligera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24117130]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228307]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31150241]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31860304]
NPO40372	Tephrosia linearis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32155073]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223193]
NPO1425	Salvia palaestina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6677714]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[7506311]
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759170]
NPO17584	Crataegus maximowiczii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9258	Plantago cornuti	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17266	Hedychium yunnanense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17584	Crataegus maximowiczii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4487	Fritillaria thunbergii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4713	Eucalyptus cordata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2839	Dovyalis abyssinica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2495	Agave xylonacantha	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO53	Nephelium mutabile	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6977	Triopha carpenteri	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3212	Bipolaris sorokiniana	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9136	Pseudocyclosorus subochthodes	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6766	Antiphiona pinnatisecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17266	Hedychium yunnanense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4873	Plectranthus sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1905	Fagraea fragrans	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10991	Maackia tashiroi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9567	Enicosanthum cupulare	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5784	Walsura chrysogyne	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12873	Tessaria absinthioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3796	Pseudomonas viridiflava	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11435	Tulipa sylvestris	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10211	Pajanelia multijuga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21329	Ilyonectria destructans	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19826	Helicoverpa armigera	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2012	Turnera diffusa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4487	Fritillaria thunbergii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5020	Jasonia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6706	Arthrobotrys oligospora	Species	Orbiliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1425	Salvia palaestina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17584	Crataegus maximowiczii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18231	Rhagoletis cerasi	Species	Tephritidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26103	Streptomyces bobili	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10810	Acridocarpus vivy	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9258	Plantago cornuti	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5442	Bryum weigelii	Species	Bryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9079	Tephrosia egregia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Others	6

Activity Type	# Activity
Cell Line	9
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[478588]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[478589]
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[478590]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[478590]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[478591]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	0.8	%	PMID[478593]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	57.6	%	PMID[478593]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	0.09	%	PMID[478593]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	8.63	%	PMID[478593]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	0.92	%	PMID[478593]
NPT2	Others	Unspecified		MED	=	0.1	ug ml-1	PMID[478590]

☑ 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 NPC137062 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	453
0.1-0.2	1953
0.2-0.3	4903
0.3-0.4	11340
0.4-0.5	6025
0.5-0.6	3678
0.6-0.7	4899
0.7-0.8	4843
0.8-0.85	2259
0.85-0.9	1394
0.9-0.95	666
0.95-1	284

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC52005
1.0	High Similarity	NPC183950
1.0	High Similarity	NPC287101
1.0	High Similarity	NPC223579
0.993	High Similarity	NPC120464
0.9861	High Similarity	NPC200740
0.9861	High Similarity	NPC125062
0.9861	High Similarity	NPC54394
0.9861	High Similarity	NPC252933
0.986	High Similarity	NPC48479
0.986	High Similarity	NPC177298
0.9859	High Similarity	NPC12200
0.9859	High Similarity	NPC108406
0.9793	High Similarity	NPC82325
0.9793	High Similarity	NPC275836
0.9793	High Similarity	NPC275722
0.9793	High Similarity	NPC131624
0.9793	High Similarity	NPC241498
0.9793	High Similarity	NPC198826
0.9793	High Similarity	NPC256283
0.9793	High Similarity	NPC120163
0.9793	High Similarity	NPC162313
0.9793	High Similarity	NPC212678
0.9793	High Similarity	NPC83508
0.9793	High Similarity	NPC60972
0.9793	High Similarity	NPC25270
0.9793	High Similarity	NPC279989
0.9793	High Similarity	NPC57030
0.9793	High Similarity	NPC55205
0.9793	High Similarity	NPC239128
0.9793	High Similarity	NPC222830
0.9793	High Similarity	NPC71334
0.9793	High Similarity	NPC187498
0.9793	High Similarity	NPC156222
0.9793	High Similarity	NPC39732
0.9793	High Similarity	NPC293183
0.9793	High Similarity	NPC188203
0.9793	High Similarity	NPC301323
0.9793	High Similarity	NPC100887
0.979	High Similarity	NPC195202
0.9726	High Similarity	NPC160951
0.9726	High Similarity	NPC145379
0.9726	High Similarity	NPC270620
0.9726	High Similarity	NPC236223
0.9726	High Similarity	NPC274327
0.9726	High Similarity	NPC176775
0.9726	High Similarity	NPC78326
0.9726	High Similarity	NPC231018
0.9726	High Similarity	NPC47781
0.9726	High Similarity	NPC255350
0.9726	High Similarity	NPC179126
0.9726	High Similarity	NPC69394
0.9726	High Similarity	NPC183878
0.9726	High Similarity	NPC22519
0.9724	High Similarity	NPC133953
0.9724	High Similarity	NPC50403
0.9724	High Similarity	NPC28274
0.9722	High Similarity	NPC87125
0.9722	High Similarity	NPC270465
0.9722	High Similarity	NPC159103
0.972	High Similarity	NPC62536
0.972	High Similarity	NPC33265
0.966	High Similarity	NPC128863
0.966	High Similarity	NPC167815
0.966	High Similarity	NPC146165
0.966	High Similarity	NPC227325
0.966	High Similarity	NPC4455
0.966	High Similarity	NPC20830
0.966	High Similarity	NPC280339
0.966	High Similarity	NPC138360
0.966	High Similarity	NPC92659
0.966	High Similarity	NPC44079
0.966	High Similarity	NPC201136
0.966	High Similarity	NPC213622
0.966	High Similarity	NPC50715
0.966	High Similarity	NPC2476
0.966	High Similarity	NPC256612
0.966	High Similarity	NPC196439
0.966	High Similarity	NPC183597
0.966	High Similarity	NPC201451
0.966	High Similarity	NPC26227
0.966	High Similarity	NPC163780
0.9658	High Similarity	NPC142540
0.9658	High Similarity	NPC302950
0.9658	High Similarity	NPC219582
0.9658	High Similarity	NPC236637
0.9658	High Similarity	NPC471982
0.9658	High Similarity	NPC123886
0.9655	High Similarity	NPC188871
0.9655	High Similarity	NPC149127
0.9655	High Similarity	NPC306821
0.9655	High Similarity	NPC50728
0.9655	High Similarity	NPC184136
0.9655	High Similarity	NPC286342
0.9655	High Similarity	NPC166753
0.9653	High Similarity	NPC119059
0.9648	High Similarity	NPC279121
0.9595	High Similarity	NPC43243
0.9595	High Similarity	NPC265511
0.9595	High Similarity	NPC98661
0.9595	High Similarity	NPC245546
0.9595	High Similarity	NPC49824
0.9595	High Similarity	NPC266960
0.9595	High Similarity	NPC247017
0.9592	High Similarity	NPC75279
0.9592	High Similarity	NPC58382
0.9592	High Similarity	NPC250822
0.9592	High Similarity	NPC276409
0.9592	High Similarity	NPC18727
0.9592	High Similarity	NPC162351
0.9589	High Similarity	NPC31363
0.9589	High Similarity	NPC226973
0.9589	High Similarity	NPC308451
0.9589	High Similarity	NPC208043
0.9589	High Similarity	NPC260895
0.9589	High Similarity	NPC236769
0.9586	High Similarity	NPC259713
0.9586	High Similarity	NPC216318
0.9586	High Similarity	NPC328119
0.9586	High Similarity	NPC296197
0.9586	High Similarity	NPC17286
0.9583	High Similarity	NPC168803
0.958	High Similarity	NPC70136
0.9577	High Similarity	NPC175013
0.953	High Similarity	NPC110070
0.953	High Similarity	NPC174908
0.953	High Similarity	NPC287979
0.953	High Similarity	NPC163524
0.953	High Similarity	NPC203891
0.953	High Similarity	NPC224137
0.953	High Similarity	NPC176665
0.953	High Similarity	NPC305663
0.953	High Similarity	NPC101830
0.953	High Similarity	NPC93376
0.953	High Similarity	NPC75215
0.953	High Similarity	NPC189179
0.953	High Similarity	NPC227192
0.953	High Similarity	NPC470402
0.9527	High Similarity	NPC234255
0.9527	High Similarity	NPC2928
0.9527	High Similarity	NPC208197
0.9524	High Similarity	NPC257648
0.9524	High Similarity	NPC301123
0.9524	High Similarity	NPC199100
0.9524	High Similarity	NPC472912
0.9524	High Similarity	NPC477231
0.9524	High Similarity	NPC180234
0.9524	High Similarity	NPC260979
0.9524	High Similarity	NPC120537
0.9521	High Similarity	NPC29231
0.9521	High Similarity	NPC88804
0.9521	High Similarity	NPC3825
0.9521	High Similarity	NPC45873
0.9521	High Similarity	NPC219330
0.9517	High Similarity	NPC261548
0.9517	High Similarity	NPC254702
0.9517	High Similarity	NPC194653
0.9517	High Similarity	NPC139364
0.9517	High Similarity	NPC80710
0.9517	High Similarity	NPC203747
0.9514	High Similarity	NPC179271
0.9514	High Similarity	NPC20791
0.9467	High Similarity	NPC7846
0.9467	High Similarity	NPC284127
0.9467	High Similarity	NPC300943
0.9467	High Similarity	NPC4481
0.9467	High Similarity	NPC476410
0.9467	High Similarity	NPC176300
0.9467	High Similarity	NPC191459
0.9467	High Similarity	NPC25495
0.9467	High Similarity	NPC9609
0.9467	High Similarity	NPC261004
0.9467	High Similarity	NPC19687
0.9467	High Similarity	NPC143828
0.9467	High Similarity	NPC152166
0.9467	High Similarity	NPC204854
0.9467	High Similarity	NPC288669
0.9467	High Similarity	NPC18772
0.9467	High Similarity	NPC253634
0.9467	High Similarity	NPC115798
0.9467	High Similarity	NPC18607
0.9467	High Similarity	NPC22472
0.9467	High Similarity	NPC105242
0.9467	High Similarity	NPC172202
0.9467	High Similarity	NPC130894
0.9463	High Similarity	NPC195796
0.9463	High Similarity	NPC255106
0.9463	High Similarity	NPC55619
0.9463	High Similarity	NPC13858
0.9463	High Similarity	NPC200388
0.9463	High Similarity	NPC291878
0.9463	High Similarity	NPC35038
0.9463	High Similarity	NPC472455
0.9463	High Similarity	NPC292107
0.9463	High Similarity	NPC471985
0.9463	High Similarity	NPC474520
0.9463	High Similarity	NPC278778
0.9463	High Similarity	NPC235165
0.9463	High Similarity	NPC326037
0.9463	High Similarity	NPC472916

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 NPC137062 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	432
0.1-0.2	969
0.2-0.3	1798
0.3-0.4	2662
0.4-0.5	1742
0.5-0.6	989
0.6-0.7	387
0.7-0.8	107
0.8-0.85	42
0.85-0.9	12
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9726	High Similarity	NPD2801	Approved
0.9658	High Similarity	NPD1934	Approved
0.9648	High Similarity	NPD1511	Approved
0.9514	High Similarity	NPD1512	Approved
0.9329	High Similarity	NPD2393	Clinical (unspecified phase)
0.9205	High Similarity	NPD3882	Suspended
0.9139	High Similarity	NPD3817	Phase 2
0.9038	High Similarity	NPD6167	Clinical (unspecified phase)
0.9038	High Similarity	NPD6168	Clinical (unspecified phase)
0.9038	High Similarity	NPD6166	Phase 2
0.8987	High Similarity	NPD7054	Approved
0.8931	High Similarity	NPD7472	Approved
0.8924	High Similarity	NPD3818	Discontinued
0.8919	High Similarity	NPD4378	Clinical (unspecified phase)
0.8812	High Similarity	NPD7074	Phase 3
0.8758	High Similarity	NPD6797	Phase 2
0.8704	High Similarity	NPD7251	Discontinued
0.8699	High Similarity	NPD1552	Clinical (unspecified phase)
0.8699	High Similarity	NPD1550	Clinical (unspecified phase)
0.869	High Similarity	NPD1510	Phase 2
0.865	High Similarity	NPD7808	Phase 3
0.865	High Similarity	NPD4338	Clinical (unspecified phase)
0.8639	High Similarity	NPD1549	Phase 2
0.8627	High Similarity	NPD4380	Phase 2
0.859	High Similarity	NPD4868	Clinical (unspecified phase)
0.8542	High Similarity	NPD1240	Approved
0.8535	High Similarity	NPD4381	Clinical (unspecified phase)
0.8503	High Similarity	NPD2796	Approved
0.8477	Intermediate Similarity	NPD6799	Approved
0.8438	Intermediate Similarity	NPD6232	Discontinued
0.8428	Intermediate Similarity	NPD5494	Approved
0.8425	Intermediate Similarity	NPD1607	Approved
0.8421	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD7075	Discontinued
0.8414	Intermediate Similarity	NPD943	Approved
0.8395	Intermediate Similarity	NPD7473	Discontinued
0.8389	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1465	Phase 2
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8264	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7819	Suspended
0.8194	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5402	Approved
0.8163	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1613	Approved
0.8158	Intermediate Similarity	NPD3750	Approved
0.8153	Intermediate Similarity	NPD6599	Discontinued
0.8148	Intermediate Similarity	NPD1247	Approved
0.8137	Intermediate Similarity	NPD919	Approved
0.8108	Intermediate Similarity	NPD447	Suspended
0.8108	Intermediate Similarity	NPD230	Phase 1
0.8101	Intermediate Similarity	NPD7411	Suspended
0.8084	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD5403	Approved
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8065	Intermediate Similarity	NPD5401	Approved
0.8049	Intermediate Similarity	NPD3926	Phase 2
0.8037	Intermediate Similarity	NPD6959	Discontinued
0.8013	Intermediate Similarity	NPD1551	Phase 2
0.7974	Intermediate Similarity	NPD2800	Approved
0.7962	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD3027	Phase 3
0.7947	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6559	Discontinued
0.7905	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2935	Discontinued
0.7867	Intermediate Similarity	NPD1933	Approved
0.7853	Intermediate Similarity	NPD3749	Approved
0.7829	Intermediate Similarity	NPD3748	Approved
0.7823	Intermediate Similarity	NPD9494	Approved
0.7806	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1243	Approved
0.7736	Intermediate Similarity	NPD920	Approved
0.7727	Intermediate Similarity	NPD2344	Approved
0.7722	Intermediate Similarity	NPD2534	Approved
0.7722	Intermediate Similarity	NPD2532	Approved
0.7722	Intermediate Similarity	NPD2533	Approved
0.7711	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7688	Intermediate Similarity	NPD1653	Approved
0.7687	Intermediate Similarity	NPD1203	Approved
0.7667	Intermediate Similarity	NPD2313	Discontinued
0.7662	Intermediate Similarity	NPD6100	Approved
0.7662	Intermediate Similarity	NPD6099	Approved
0.764	Intermediate Similarity	NPD3226	Approved
0.7622	Intermediate Similarity	NPD1548	Phase 1
0.7619	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6234	Discontinued
0.7588	Intermediate Similarity	NPD3751	Discontinued
0.7582	Intermediate Similarity	NPD6651	Approved
0.7572	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD422	Phase 1
0.7532	Intermediate Similarity	NPD2309	Approved
0.7532	Intermediate Similarity	NPD6190	Approved
0.7527	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2346	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7483	Intermediate Similarity	NPD9717	Approved
0.7483	Intermediate Similarity	NPD9269	Phase 2
0.7457	Intermediate Similarity	NPD5953	Discontinued
0.7456	Intermediate Similarity	NPD3787	Discontinued
0.7442	Intermediate Similarity	NPD7286	Phase 2
0.7438	Intermediate Similarity	NPD7390	Discontinued
0.7434	Intermediate Similarity	NPD3268	Approved
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7417	Intermediate Similarity	NPD4908	Phase 1
0.7415	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1610	Phase 2
0.7414	Intermediate Similarity	NPD7685	Pre-registration
0.74	Intermediate Similarity	NPD2798	Approved
0.7394	Intermediate Similarity	NPD37	Approved
0.7383	Intermediate Similarity	NPD3225	Approved
0.7372	Intermediate Similarity	NPD4308	Phase 3
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7365	Intermediate Similarity	NPD1608	Approved
0.7365	Intermediate Similarity	NPD4966	Approved
0.7365	Intermediate Similarity	NPD4965	Approved
0.7365	Intermediate Similarity	NPD4967	Phase 2
0.7358	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3018	Phase 2
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2797	Approved
0.732	Intermediate Similarity	NPD411	Approved
0.732	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5242	Approved
0.731	Intermediate Similarity	NPD5536	Phase 2
0.7296	Intermediate Similarity	NPD2654	Approved
0.7283	Intermediate Similarity	NPD7228	Approved
0.7268	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD228	Approved
0.7253	Intermediate Similarity	NPD4363	Phase 3
0.7253	Intermediate Similarity	NPD4360	Phase 2
0.7238	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6385	Approved
0.7229	Intermediate Similarity	NPD6386	Approved
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7219	Intermediate Similarity	NPD3266	Approved
0.7219	Intermediate Similarity	NPD3267	Approved
0.7211	Intermediate Similarity	NPD9268	Approved
0.7208	Intermediate Similarity	NPD6798	Discontinued
0.7202	Intermediate Similarity	NPD5353	Approved
0.7202	Intermediate Similarity	NPD4288	Approved
0.72	Intermediate Similarity	NPD2983	Phase 2
0.72	Intermediate Similarity	NPD2982	Phase 2
0.7188	Intermediate Similarity	NPD1652	Phase 2
0.7186	Intermediate Similarity	NPD6844	Discontinued
0.7181	Intermediate Similarity	NPD1201	Approved
0.7178	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2403	Approved
0.7162	Intermediate Similarity	NPD17	Approved
0.7161	Intermediate Similarity	NPD6233	Phase 2
0.7151	Intermediate Similarity	NPD5710	Approved
0.7151	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD9545	Approved
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7133	Intermediate Similarity	NPD2981	Phase 2
0.7123	Intermediate Similarity	NPD9493	Approved
0.712	Intermediate Similarity	NPD4361	Phase 2
0.712	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1558	Phase 1
0.7115	Intermediate Similarity	NPD4307	Phase 2
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.7105	Intermediate Similarity	NPD1470	Approved
0.7105	Intermediate Similarity	NPD7584	Approved
0.7099	Intermediate Similarity	NPD2354	Approved
0.7097	Intermediate Similarity	NPD1296	Phase 2
0.7086	Intermediate Similarity	NPD4749	Approved
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7069	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7266	Discontinued
0.7059	Intermediate Similarity	NPD1019	Discontinued
0.7052	Intermediate Similarity	NPD7229	Phase 3
0.7034	Intermediate Similarity	NPD1241	Discontinued
0.703	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7039	Approved
0.7022	Intermediate Similarity	NPD7038	Approved
0.702	Intermediate Similarity	NPD1481	Phase 2
0.702	Intermediate Similarity	NPD3972	Approved
0.7018	Intermediate Similarity	NPD6971	Discontinued
0.7013	Intermediate Similarity	NPD2861	Phase 2
0.7006	Intermediate Similarity	NPD4060	Phase 1
0.7006	Intermediate Similarity	NPD7458	Discontinued
0.7	Intermediate Similarity	NPD2296	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