NPASS Compound

Structure

CID184649 OpenBabel06191715562D 21 23 0 0 1 0 0 0 0 0999 V2000 -4.3301 4.5000 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 -2.5981 3.5000 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 -1.7321 3.0000 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 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 2.5981 0.5000 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 -1.7321 2.0000 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 -0.8660 1.5000 0.0000 C 0 0 2 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 0.8660 0.5000 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 -4.3301 3.5000 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 20 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 11 1 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 21 1 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 11 1 6 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	2.695
LogD:	2.418
LogS:	-3.794
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.887
Synthetic Accessibility Score:	2.834
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.755
MDCK Permeability:	1.6601035895291716e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.889

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	98.11461639404297%
Volume Distribution (VD):	0.486
Pgp-substrate:	1.6463690996170044%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.903
CYP2C19-substrate:	0.238
CYP2C9-inhibitor:	0.836
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.856
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	11.442
Half-life (T1/2):	0.541

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.646
AMES Toxicity:	0.659
Rat Oral Acute Toxicity:	0.609
Maximum Recommended Daily Dose:	0.266
Skin Sensitization:	0.789
Carcinogencity:	0.294
Eye Corrosion:	0.003
Eye Irritation:	0.595
Respiratory Toxicity:	0.079

Download Data

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

Natural Product: NPC184649

Natural Product ID:	NPC184649
*Common Name:**	(3S)-Vestitone
IUPAC Name:	(3S)-7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:	(3S)-Vestitone
Standard InCHIKey:	WQCJOKYOIJVEFN-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-20-10-3-5-11(14(18)7-10)13-8-21-15-6-9(17)2-4-12(15)16(13)19/h2-7,13,17-18H,8H2,1H3/t13-/m1/s1
SMILES:	COc1ccc([C@H]2COc3cc(ccc3C2=O)O)c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253038
PubChem CID:	44446897
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids

*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
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	bud covers	n.a.	n.a.	PMID[11975520]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[12662107]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16643051]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[16989517]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[17950610]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[18440233]
NPO17211	Albizia inundata	Species	Fabaceae	Eukaryota	aerial parts	Primavera, Department Patino, Province of Formosa, Argentina (lat. 27S, long. 58W)	1999-AUG	PMID[21314099]
NPO17211	Albizia inundata	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21314099]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26938776]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32525315]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3839140]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7684040]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9868153]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16799	Glinus lotoides	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20585	Urochloa decumbens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14521	Oxalis purpurea	Species	Oxalidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10892	Xanthorrhoea resinosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16306	Curcuma caesia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17293	Menegazzia asahinae	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10594	Centaurea solstitialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13683	Cosmos diversifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO875	Cryptocarya oblata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17367	Parmelia subrudecta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12557	Strychnos tricalysioides	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14256	Acnistus breviflorus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4960	Garrya elliptica	Species	Garryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5380	Eucalyptus australiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2046	Cathormion altissimum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9342	Solenopsis punctaticeps	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7608	Phelline lucida	Species	Phellinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12207	Lagochilus leiacanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO206	Ormosia nobilis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14075	Streptomyces viridogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1398	Trichodesma incanum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13192	Chara ceratophylla	Species	Characeae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10928	Xenia obscuronata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11046	Ocimum pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16013	Inga velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3059	Erythrina pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16799	Glinus lotoides	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12946	Onobrychis cyri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12726	Piptostigma fugax	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12607	Ircinia dendroides	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO534	Nassauvia cumingii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12035	Rhododendron ungerni	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17834	Tipuana tipu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17211	Albizia inundata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	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	6
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	>	100.0	uM	PMID[564416]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[564417]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[564417]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[564417]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	67000.0	nM	PMID[564417]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[564417]

☑ 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 NPC184649 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	366
0.1-0.2	1508
0.2-0.3	3660
0.3-0.4	9017
0.4-0.5	9364
0.5-0.6	3512
0.6-0.7	5281
0.7-0.8	5321
0.8-0.85	2464
0.85-0.9	1512
0.9-0.95	659
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC303185
0.9928	High Similarity	NPC113770
0.9928	High Similarity	NPC299011
0.9856	High Similarity	NPC311144
0.9855	High Similarity	NPC202981
0.9787	High Similarity	NPC39195
0.9716	High Similarity	NPC308200
0.9648	High Similarity	NPC145467
0.9638	High Similarity	NPC261234
0.9638	High Similarity	NPC316480
0.958	High Similarity	NPC471114
0.9574	High Similarity	NPC271288
0.9568	High Similarity	NPC129853
0.9568	High Similarity	NPC284550
0.9568	High Similarity	NPC76445
0.9565	High Similarity	NPC99333
0.9565	High Similarity	NPC188947
0.9565	High Similarity	NPC118813
0.9565	High Similarity	NPC280284
0.9514	High Similarity	NPC471115
0.9514	High Similarity	NPC29777
0.9514	High Similarity	NPC267117
0.9507	High Similarity	NPC477955
0.95	High Similarity	NPC3188
0.9496	High Similarity	NPC20709
0.9496	High Similarity	NPC274784
0.9496	High Similarity	NPC265871
0.9496	High Similarity	NPC222342
0.9496	High Similarity	NPC150648
0.9496	High Similarity	NPC225153
0.9496	High Similarity	NPC329203
0.9496	High Similarity	NPC310135
0.9493	High Similarity	NPC290291
0.9493	High Similarity	NPC275055
0.9448	High Similarity	NPC471229
0.9444	High Similarity	NPC277032
0.9437	High Similarity	NPC473015
0.9437	High Similarity	NPC473013
0.9433	High Similarity	NPC73028
0.9429	High Similarity	NPC188243
0.9429	High Similarity	NPC6407
0.9429	High Similarity	NPC110228
0.9424	High Similarity	NPC147686
0.9424	High Similarity	NPC124269
0.9424	High Similarity	NPC329225
0.9424	High Similarity	NPC12175
0.9424	High Similarity	NPC55162
0.9424	High Similarity	NPC90665
0.9424	High Similarity	NPC279668
0.9424	High Similarity	NPC278323
0.9424	High Similarity	NPC472460
0.9424	High Similarity	NPC309154
0.9388	High Similarity	NPC255807
0.9388	High Similarity	NPC31018
0.9371	High Similarity	NPC472629
0.9366	High Similarity	NPC81697
0.9366	High Similarity	NPC18585
0.9366	High Similarity	NPC91560
0.9366	High Similarity	NPC75049
0.9366	High Similarity	NPC143896
0.9366	High Similarity	NPC221432
0.9366	High Similarity	NPC166138
0.9366	High Similarity	NPC125894
0.9366	High Similarity	NPC107177
0.9366	High Similarity	NPC223812
0.9366	High Similarity	NPC164980
0.9366	High Similarity	NPC169591
0.9366	High Similarity	NPC77794
0.9366	High Similarity	NPC39329
0.9366	High Similarity	NPC149026
0.9366	High Similarity	NPC257097
0.9366	High Similarity	NPC106985
0.9366	High Similarity	NPC310130
0.9366	High Similarity	NPC85162
0.9366	High Similarity	NPC150408
0.9366	High Similarity	NPC68104
0.9366	High Similarity	NPC278249
0.9366	High Similarity	NPC175504
0.9362	High Similarity	NPC312391
0.9362	High Similarity	NPC213322
0.9362	High Similarity	NPC324386
0.9362	High Similarity	NPC4743
0.9357	High Similarity	NPC140890
0.9353	High Similarity	NPC209560
0.9353	High Similarity	NPC228661
0.9353	High Similarity	NPC107586
0.9353	High Similarity	NPC162680
0.9353	High Similarity	NPC294409
0.9353	High Similarity	NPC476480
0.9353	High Similarity	NPC84585
0.9353	High Similarity	NPC181124
0.9353	High Similarity	NPC295261
0.9353	High Similarity	NPC13768
0.9353	High Similarity	NPC287246
0.9353	High Similarity	NPC250266
0.9353	High Similarity	NPC12296
0.9353	High Similarity	NPC116632
0.9353	High Similarity	NPC303644
0.9353	High Similarity	NPC79943
0.9353	High Similarity	NPC32441
0.9353	High Similarity	NPC7013
0.9353	High Similarity	NPC243083
0.9353	High Similarity	NPC266597
0.9353	High Similarity	NPC188879
0.9353	High Similarity	NPC296490
0.9348	High Similarity	NPC9985
0.9348	High Similarity	NPC239495
0.932	High Similarity	NPC203080
0.932	High Similarity	NPC213608
0.932	High Similarity	NPC1477
0.931	High Similarity	NPC317492
0.931	High Similarity	NPC266499
0.931	High Similarity	NPC473016
0.9306	High Similarity	NPC300988
0.9306	High Similarity	NPC10990
0.9301	High Similarity	NPC236766
0.9301	High Similarity	NPC234629
0.9301	High Similarity	NPC311741
0.9301	High Similarity	NPC470890
0.9301	High Similarity	NPC131579
0.9301	High Similarity	NPC131568
0.9301	High Similarity	NPC87486
0.9301	High Similarity	NPC473014
0.9301	High Similarity	NPC209040
0.9301	High Similarity	NPC124780
0.9301	High Similarity	NPC197252
0.9301	High Similarity	NPC235217
0.9301	High Similarity	NPC469764
0.9296	High Similarity	NPC64915
0.9296	High Similarity	NPC10937
0.9296	High Similarity	NPC227579
0.9296	High Similarity	NPC37496
0.9296	High Similarity	NPC324134
0.9296	High Similarity	NPC324436
0.9296	High Similarity	NPC223500
0.9296	High Similarity	NPC328164
0.9296	High Similarity	NPC40833
0.9296	High Similarity	NPC265040
0.9296	High Similarity	NPC76338
0.9296	High Similarity	NPC1089
0.9296	High Similarity	NPC296917
0.9296	High Similarity	NPC161506
0.9296	High Similarity	NPC32739
0.9296	High Similarity	NPC78
0.9296	High Similarity	NPC66515
0.9296	High Similarity	NPC166482
0.9296	High Similarity	NPC306829
0.9296	High Similarity	NPC194432
0.9296	High Similarity	NPC159855
0.9296	High Similarity	NPC169479
0.9296	High Similarity	NPC177354
0.9296	High Similarity	NPC220998
0.9296	High Similarity	NPC125855
0.9296	High Similarity	NPC182852
0.9296	High Similarity	NPC107572
0.9296	High Similarity	NPC167624
0.9296	High Similarity	NPC76372
0.9296	High Similarity	NPC228504
0.9296	High Similarity	NPC310340
0.9296	High Similarity	NPC148757
0.9296	High Similarity	NPC144499
0.9296	High Similarity	NPC166934
0.9291	High Similarity	NPC101366
0.9291	High Similarity	NPC69769
0.9291	High Similarity	NPC182421
0.9291	High Similarity	NPC281207
0.9291	High Similarity	NPC269652
0.9281	High Similarity	NPC127447
0.9281	High Similarity	NPC29353
0.9281	High Similarity	NPC47815
0.9281	High Similarity	NPC231772
0.9281	High Similarity	NPC235428
0.9281	High Similarity	NPC87545
0.9281	High Similarity	NPC194281
0.9281	High Similarity	NPC473887
0.9281	High Similarity	NPC124784
0.9281	High Similarity	NPC240593
0.9281	High Similarity	NPC234133
0.9281	High Similarity	NPC213603
0.9262	High Similarity	NPC181960
0.9262	High Similarity	NPC299520
0.9262	High Similarity	NPC129684
0.9252	High Similarity	NPC5871
0.9252	High Similarity	NPC210597
0.9252	High Similarity	NPC474843
0.9247	High Similarity	NPC470107
0.9241	High Similarity	NPC37135
0.9241	High Similarity	NPC186397
0.9241	High Similarity	NPC266572
0.9241	High Similarity	NPC168085
0.9236	High Similarity	NPC24136
0.9236	High Similarity	NPC229190
0.9236	High Similarity	NPC290133
0.9236	High Similarity	NPC187282
0.9236	High Similarity	NPC469758
0.9236	High Similarity	NPC285630
0.9236	High Similarity	NPC127059
0.9236	High Similarity	NPC196114
0.9231	High Similarity	NPC478086
0.9231	High Similarity	NPC185276

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 NPC184649 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	930
0.2-0.3	1523
0.3-0.4	2495
0.4-0.5	1956
0.5-0.6	1180
0.6-0.7	499
0.7-0.8	153
0.8-0.85	48
0.85-0.9	25
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9424	High Similarity	NPD1549	Phase 2
0.9353	High Similarity	NPD1552	Clinical (unspecified phase)
0.9353	High Similarity	NPD1550	Clinical (unspecified phase)
0.9209	High Similarity	NPD1510	Phase 2
0.9167	High Similarity	NPD4378	Clinical (unspecified phase)
0.9058	High Similarity	NPD1240	Approved
0.9007	High Similarity	NPD2796	Approved
0.9	High Similarity	NPD8443	Clinical (unspecified phase)
0.8993	High Similarity	NPD1934	Approved
0.8933	High Similarity	NPD2393	Clinical (unspecified phase)
0.8929	High Similarity	NPD1607	Approved
0.8859	High Similarity	NPD4380	Phase 2
0.8808	High Similarity	NPD7819	Suspended
0.88	High Similarity	NPD7411	Suspended
0.8776	High Similarity	NPD7410	Clinical (unspecified phase)
0.8758	High Similarity	NPD7075	Discontinued
0.8758	High Similarity	NPD4381	Clinical (unspecified phase)
0.8707	High Similarity	NPD1511	Approved
0.8684	High Similarity	NPD7096	Clinical (unspecified phase)
0.8684	High Similarity	NPD2801	Approved
0.8636	High Similarity	NPD3749	Approved
0.863	High Similarity	NPD3750	Approved
0.8591	High Similarity	NPD1512	Approved
0.8581	High Similarity	NPD6799	Approved
0.8571	High Similarity	NPD3882	Suspended
0.8562	High Similarity	NPD2800	Approved
0.8544	High Similarity	NPD7852	Clinical (unspecified phase)
0.8526	High Similarity	NPD5494	Approved
0.8493	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD6599	Discontinued
0.8483	Intermediate Similarity	NPD1551	Phase 2
0.8471	Intermediate Similarity	NPD6959	Discontinued
0.8452	Intermediate Similarity	NPD7768	Phase 2
0.8428	Intermediate Similarity	NPD6166	Phase 2
0.8428	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD2344	Approved
0.8377	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3818	Discontinued
0.8311	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD920	Approved
0.8288	Intermediate Similarity	NPD3748	Approved
0.8288	Intermediate Similarity	NPD2799	Discontinued
0.8272	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD3817	Phase 2
0.8261	Intermediate Similarity	NPD1610	Phase 2
0.8255	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD4908	Phase 1
0.8221	Intermediate Similarity	NPD7074	Phase 3
0.82	Intermediate Similarity	NPD2309	Approved
0.816	Intermediate Similarity	NPD7054	Approved
0.8158	Intermediate Similarity	NPD2532	Approved
0.8158	Intermediate Similarity	NPD2533	Approved
0.8158	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD2534	Approved
0.8148	Intermediate Similarity	NPD7473	Discontinued
0.8129	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD2313	Discontinued
0.811	Intermediate Similarity	NPD7472	Approved
0.8108	Intermediate Similarity	NPD6099	Approved
0.8108	Intermediate Similarity	NPD6100	Approved
0.8108	Intermediate Similarity	NPD2935	Discontinued
0.8075	Intermediate Similarity	NPD6232	Discontinued
0.8072	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1243	Approved
0.8065	Intermediate Similarity	NPD3226	Approved
0.8061	Intermediate Similarity	NPD5953	Discontinued
0.8061	Intermediate Similarity	NPD6797	Phase 2
0.8054	Intermediate Similarity	NPD2346	Discontinued
0.8052	Intermediate Similarity	NPD5403	Approved
0.8049	Intermediate Similarity	NPD7286	Phase 2
0.8041	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD5401	Approved
0.8038	Intermediate Similarity	NPD5402	Approved
0.8028	Intermediate Similarity	NPD1203	Approved
0.8027	Intermediate Similarity	NPD6651	Approved
0.8026	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD943	Approved
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8012	Intermediate Similarity	NPD7251	Discontinued
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.7975	Intermediate Similarity	NPD1465	Phase 2
0.7972	Intermediate Similarity	NPD2798	Approved
0.7964	Intermediate Similarity	NPD7808	Phase 3
0.7964	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5844	Phase 1
0.7895	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD3268	Approved
0.7862	Intermediate Similarity	NPD6832	Phase 2
0.7844	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1548	Phase 1
0.7817	Intermediate Similarity	NPD9717	Approved
0.7816	Intermediate Similarity	NPD4363	Phase 3
0.7816	Intermediate Similarity	NPD4360	Phase 2
0.7805	Intermediate Similarity	NPD3926	Phase 2
0.7791	Intermediate Similarity	NPD1247	Approved
0.7778	Intermediate Similarity	NPD2797	Approved
0.7736	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD230	Phase 1
0.7718	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1608	Approved
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7682	Intermediate Similarity	NPD4308	Phase 3
0.7669	Intermediate Similarity	NPD919	Approved
0.7665	Intermediate Similarity	NPD3751	Discontinued
0.7655	Intermediate Similarity	NPD3266	Approved
0.7655	Intermediate Similarity	NPD3267	Approved
0.7651	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1613	Approved
0.7636	Intermediate Similarity	NPD5711	Approved
0.7636	Intermediate Similarity	NPD5710	Approved
0.7635	Intermediate Similarity	NPD3764	Approved
0.7628	Intermediate Similarity	NPD7390	Discontinued
0.7622	Intermediate Similarity	NPD422	Phase 1
0.7619	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD447	Suspended
0.76	Intermediate Similarity	NPD1933	Approved
0.7593	Intermediate Similarity	NPD2296	Approved
0.7593	Intermediate Similarity	NPD4288	Approved
0.7589	Intermediate Similarity	NPD9545	Approved
0.7586	Intermediate Similarity	NPD4287	Approved
0.7571	Intermediate Similarity	NPD4361	Phase 2
0.7571	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3972	Approved
0.7566	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2861	Phase 2
0.7551	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1470	Approved
0.753	Intermediate Similarity	NPD7229	Phase 3
0.7517	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8313	Approved
0.7484	Intermediate Similarity	NPD2654	Approved
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5124	Phase 1
0.7483	Intermediate Similarity	NPD17	Approved
0.7483	Intermediate Similarity	NPD1019	Discontinued
0.7483	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1241	Discontinued
0.7469	Intermediate Similarity	NPD6844	Discontinued
0.7468	Intermediate Similarity	NPD1471	Phase 3
0.7466	Intermediate Similarity	NPD3225	Approved
0.7466	Intermediate Similarity	NPD1876	Approved
0.745	Intermediate Similarity	NPD4625	Phase 3
0.7447	Intermediate Similarity	NPD9493	Approved
0.744	Intermediate Similarity	NPD2403	Approved
0.7425	Intermediate Similarity	NPD3787	Discontinued
0.7423	Intermediate Similarity	NPD5760	Phase 2
0.7423	Intermediate Similarity	NPD5761	Phase 2
0.7417	Intermediate Similarity	NPD4307	Phase 2
0.74	Intermediate Similarity	NPD411	Approved
0.74	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6104	Discontinued
0.7379	Intermediate Similarity	NPD1201	Approved
0.7371	Intermediate Similarity	NPD8434	Phase 2
0.7368	Intermediate Similarity	NPD1729	Discontinued
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.7365	Intermediate Similarity	NPD7199	Phase 2
0.7362	Intermediate Similarity	NPD7577	Discontinued
0.7362	Intermediate Similarity	NPD6280	Approved
0.7362	Intermediate Similarity	NPD6279	Approved
0.7333	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7003	Approved
0.7297	Intermediate Similarity	NPD1164	Approved
0.7285	Intermediate Similarity	NPD1296	Phase 2
0.7285	Intermediate Similarity	NPD6798	Discontinued
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7584	Approved
0.7256	Intermediate Similarity	NPD37	Approved
0.7251	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6234	Discontinued
0.7229	Intermediate Similarity	NPD4966	Approved
0.7229	Intermediate Similarity	NPD4965	Approved
0.7229	Intermediate Similarity	NPD4967	Phase 2
0.7219	Intermediate Similarity	NPD3027	Phase 3
0.7219	Intermediate Similarity	NPD6808	Phase 2
0.7216	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6777	Approved
0.7213	Intermediate Similarity	NPD6780	Approved
0.7213	Intermediate Similarity	NPD6776	Approved
0.7213	Intermediate Similarity	NPD6781	Approved
0.7213	Intermediate Similarity	NPD6778	Approved
0.7213	Intermediate Similarity	NPD6779	Approved
0.7213	Intermediate Similarity	NPD6782	Approved
0.7211	Intermediate Similarity	NPD1481	Phase 2
0.7205	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD9494	Approved
0.7197	Intermediate Similarity	NPD2424	Discontinued
0.7195	Intermediate Similarity	NPD5890	Approved
0.7195	Intermediate Similarity	NPD5889	Approved
0.7191	Intermediate Similarity	NPD8397	Clinical (unspecified phase)

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