NPASS Compound

Structure

CID273483 OpenBabel06191716082D 28 29 0 0 0 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -4.3301 -1.5000 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 0.8660 -1.5000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 1.7321 -1.0000 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 -4.3301 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 5 1 0 0 0 0 4 11 2 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 22 1 0 0 0 0 10 16 1 0 0 0 0 10 23 1 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 14 24 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 20 2 0 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.15
Volume:	395.099
LogP:	3.551
LogD:	2.357
LogS:	-3.204
# Rotatable Bonds:	7
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.292
Synthetic Accessibility Score:	2.952
Fsp3:	0.286
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:	-5.285
MDCK Permeability:	4.980853645975003e-06
Pgp-inhibitor:	0.041
Pgp-substrate:	0.631
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.777

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	97.98670959472656%
Volume Distribution (VD):	0.509
Pgp-substrate:	3.2412898540496826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.824
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.262
CYP2D6-inhibitor:	0.729
CYP2D6-substrate:	0.24
CYP3A4-inhibitor:	0.315
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	13.569
Half-life (T1/2):	0.973

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.144
AMES Toxicity:	0.184
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.163
Skin Sensitization:	0.924
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.297
Respiratory Toxicity:	0.203

Download Data

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

Natural Product: NPC273483

Natural Product ID:	NPC273483
*Common Name:**	[3-Hydroxy-4,5-Bis(Hydroxymethyl)-2-(3-Methylbut-2-Enyl)Phenyl] 2,4-Dihydroxy-6-Methylbenzoate
IUPAC Name:	[3-hydroxy-4,5-bis(hydroxymethyl)-2-(3-methylbut-2-enyl)phenyl] 2,4-dihydroxy-6-methylbenzoate
Synonyms:
Standard InCHIKey:	WTZUCTQSBSDSRG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H24O7/c1-11(2)4-5-15-18(7-13(9-22)16(10-23)20(15)26)28-21(27)19-12(3)6-14(24)8-17(19)25/h4,6-8,22-26H,5,9-10H2,1-3H3
SMILES:	OCc1c(CO)cc(c(c1O)CC=C(C)C)OC(=O)c1c(C)cc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2005906
PubChem CID:	100450
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO21301	Stereum hirsutum	Species	Stereaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12003003]
NPO21558	Ormosia sumatrana	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15568789]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16748484]
NPO19990	Axinyssa isabela	Species	Halichondriidae	Eukaryota	n.a.	Isla Isabel (Gulf of California, Mexico)	n.a.	PMID[19007287]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	fresh leaves	n.a.	n.a.	PMID[19778089]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	fresh fruits	n.a.	n.a.	PMID[20092288]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20597533]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23656415]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25565282]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25650289]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	Mycelia	n.a.	n.a.	PMID[26807743]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	Fruiting Bodies	n.a.	n.a.	PMID[33246107]
NPO4994	Pachysandra procumbens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784163]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Bulb	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18460	Trema dielsiana	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21301	Stereum hirsutum	Species	Stereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18460	Trema dielsiana	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18857	Pteronia eenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20485	Cussonia arborea	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20276	Burasaia madagascariensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13404	Plantago subulata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18460	Trema dielsiana	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21238	Berberis tabiensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20747	Stictocardia campanulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19796	Azolla filiculoides	Species	Azollaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19907	Helicobasidium mompa	Species	Helicobasidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18114	Cyclamen repandum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24508	Aspergillus brunneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19031	Thymus marschallianus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19990	Axinyssa isabela	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21490	Hypoxylon fragiforme	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21558	Ormosia sumatrana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4994	Pachysandra procumbens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21431	Rapanea laetevirens	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21301	Stereum hirsutum	Species	Stereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17541	Andryala pinnatifida	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	56

Activity Type	# Activity
Cell Line	56

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	19098.53	nM	PMID[555508]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	16788.04	nM	PMID[555508]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	18535.32	nM	PMID[555508]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	14421.15	nM	PMID[555508]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	12189.9	nM	PMID[555508]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	4497.8	nM	PMID[555508]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	17701.09	nM	PMID[555508]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	25118.86	nM	PMID[555508]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	18620.87	nM	PMID[555508]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	14757.07	nM	PMID[555508]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	17458.22	nM	PMID[555508]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	7620.79	nM	PMID[555508]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	17258.38	nM	PMID[555508]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	16255.49	nM	PMID[555508]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	30130.06	nM	PMID[555508]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	17458.22	nM	PMID[555508]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[555508]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	20370.42	nM	PMID[555508]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	8072.35	nM	PMID[555508]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	20701.41	nM	PMID[555508]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	15488.17	nM	PMID[555508]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	26302.68	nM	PMID[555508]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[555508]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	18030.18	nM	PMID[555508]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	20844.91	nM	PMID[555508]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	16218.1	nM	PMID[555508]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	21281.39	nM	PMID[555508]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	16032.45	nM	PMID[555508]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	18663.8	nM	PMID[555508]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	16180.8	nM	PMID[555508]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	21330.45	nM	PMID[555508]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	6426.88	nM	PMID[555508]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	12589.25	nM	PMID[555508]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	16443.72	nM	PMID[555508]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	17660.38	nM	PMID[555508]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	20941.12	nM	PMID[555508]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	26730.06	nM	PMID[555508]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	24043.63	nM	PMID[555508]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	32433.96	nM	PMID[555508]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	18030.18	nM	PMID[555508]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	16180.8	nM	PMID[555508]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	6854.88	nM	PMID[555508]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	15170.5	nM	PMID[555508]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	17619.76	nM	PMID[555508]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	5482.77	nM	PMID[555508]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	17741.89	nM	PMID[555508]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	17218.69	nM	PMID[555508]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	20090.93	nM	PMID[555508]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	19186.69	nM	PMID[555508]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	31405.09	nM	PMID[555508]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	29922.65	nM	PMID[555508]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[555508]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	34040.82	nM	PMID[555508]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	21232.44	nM	PMID[555508]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	18535.32	nM	PMID[555508]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	17906.06	nM	PMID[555508]

☑ 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 NPC273483 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	355
0.1-0.2	1531
0.2-0.3	3598
0.3-0.4	8279
0.4-0.5	10283
0.5-0.6	3492
0.6-0.7	5160
0.7-0.8	6335
0.8-0.85	2461
0.85-0.9	1080
0.9-0.95	110
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC291049
0.9793	High Similarity	NPC233267
0.9724	High Similarity	NPC105415
0.966	High Similarity	NPC133856
0.9597	High Similarity	NPC149618
0.9597	High Similarity	NPC89625
0.9533	High Similarity	NPC146211
0.9517	High Similarity	NPC134621
0.9474	High Similarity	NPC143050
0.9463	High Similarity	NPC217447
0.9452	High Similarity	NPC163846
0.9452	High Similarity	NPC237208
0.9452	High Similarity	NPC225173
0.9448	High Similarity	NPC95123
0.9448	High Similarity	NPC66404
0.9388	High Similarity	NPC125801
0.9384	High Similarity	NPC29577
0.9355	High Similarity	NPC112981
0.9329	High Similarity	NPC119929
0.9329	High Similarity	NPC202595
0.9324	High Similarity	NPC37139
0.932	High Similarity	NPC473927
0.931	High Similarity	NPC105648
0.9295	High Similarity	NPC20216
0.929	High Similarity	NPC156082
0.9272	High Similarity	NPC472799
0.9267	High Similarity	NPC474417
0.9267	High Similarity	NPC232645
0.9267	High Similarity	NPC149526
0.9267	High Similarity	NPC478148
0.9267	High Similarity	NPC72958
0.9262	High Similarity	NPC288036
0.9262	High Similarity	NPC65589
0.9262	High Similarity	NPC100985
0.9262	High Similarity	NPC158338
0.9262	High Similarity	NPC97029
0.9262	High Similarity	NPC97028
0.9247	High Similarity	NPC51106
0.9241	High Similarity	NPC220106
0.9205	High Similarity	NPC40356
0.9205	High Similarity	NPC154683
0.9205	High Similarity	NPC175978
0.9205	High Similarity	NPC87708
0.9205	High Similarity	NPC271681
0.92	High Similarity	NPC158866
0.92	High Similarity	NPC150928
0.92	High Similarity	NPC60413
0.9195	High Similarity	NPC256672
0.9195	High Similarity	NPC27221
0.9195	High Similarity	NPC7025
0.9195	High Similarity	NPC2569
0.9195	High Similarity	NPC172329
0.9189	High Similarity	NPC267509
0.9178	High Similarity	NPC250755
0.9172	High Similarity	NPC165172
0.9145	High Similarity	NPC169990
0.9145	High Similarity	NPC210942
0.9145	High Similarity	NPC135522
0.9133	High Similarity	NPC6923
0.9128	High Similarity	NPC8817
0.9128	High Similarity	NPC12305
0.9128	High Similarity	NPC7943
0.9128	High Similarity	NPC22005
0.9128	High Similarity	NPC123202
0.9122	High Similarity	NPC75694
0.9122	High Similarity	NPC32470
0.9119	High Similarity	NPC17219
0.9116	High Similarity	NPC469542
0.9116	High Similarity	NPC471731
0.9116	High Similarity	NPC84266
0.9116	High Similarity	NPC159721
0.9114	High Similarity	NPC292788
0.9114	High Similarity	NPC272485
0.911	High Similarity	NPC1704
0.911	High Similarity	NPC67650
0.9091	High Similarity	NPC263483
0.9073	High Similarity	NPC307780
0.9073	High Similarity	NPC325983
0.9073	High Similarity	NPC474660
0.9073	High Similarity	NPC147735
0.9073	High Similarity	NPC474735
0.9073	High Similarity	NPC309979
0.9067	High Similarity	NPC240622
0.9067	High Similarity	NPC471642
0.9067	High Similarity	NPC240253
0.9067	High Similarity	NPC471641
0.906	High Similarity	NPC290133
0.906	High Similarity	NPC470357
0.906	High Similarity	NPC187282
0.906	High Similarity	NPC24136
0.9054	High Similarity	NPC151607
0.9054	High Similarity	NPC42540
0.9051	High Similarity	NPC30027
0.9048	High Similarity	NPC474385
0.9048	High Similarity	NPC469579
0.9048	High Similarity	NPC471733
0.9048	High Similarity	NPC182255
0.9048	High Similarity	NPC94076
0.9032	High Similarity	NPC474373
0.9032	High Similarity	NPC85121
0.9026	High Similarity	NPC4547
0.9026	High Similarity	NPC180924
0.902	High Similarity	NPC329844
0.902	High Similarity	NPC193200
0.9013	High Similarity	NPC39819
0.9013	High Similarity	NPC470569
0.9007	High Similarity	NPC476684
0.9	High Similarity	NPC137296
0.9	High Similarity	NPC239440
0.9	High Similarity	NPC34802
0.9	High Similarity	NPC298778
0.9	High Similarity	NPC246716
0.9	High Similarity	NPC20543
0.9	High Similarity	NPC71055
0.8993	High Similarity	NPC312789
0.8993	High Similarity	NPC224714
0.8993	High Similarity	NPC470890
0.8986	High Similarity	NPC310340
0.8986	High Similarity	NPC294432
0.8986	High Similarity	NPC472006
0.898	High Similarity	NPC472605
0.898	High Similarity	NPC472604
0.8974	High Similarity	NPC470810
0.8974	High Similarity	NPC47623
0.8968	High Similarity	NPC246647
0.8968	High Similarity	NPC96342
0.8968	High Similarity	NPC212967
0.8968	High Similarity	NPC164110
0.8966	High Similarity	NPC135837
0.8954	High Similarity	NPC281272
0.8954	High Similarity	NPC474843
0.8947	High Similarity	NPC470107
0.8947	High Similarity	NPC470568
0.8947	High Similarity	NPC290954
0.8947	High Similarity	NPC255641
0.8947	High Similarity	NPC37348
0.8947	High Similarity	NPC295036
0.8947	High Similarity	NPC473466
0.8947	High Similarity	NPC227122
0.8938	High Similarity	NPC99613
0.8938	High Similarity	NPC26568
0.8938	High Similarity	NPC49487
0.8933	High Similarity	NPC130176
0.8933	High Similarity	NPC107625
0.8933	High Similarity	NPC472629
0.8933	High Similarity	NPC470322
0.8933	High Similarity	NPC154217
0.8933	High Similarity	NPC99454
0.8931	High Similarity	NPC29160
0.8931	High Similarity	NPC178851
0.8926	High Similarity	NPC86373
0.8926	High Similarity	NPC280404
0.8926	High Similarity	NPC470909
0.8926	High Similarity	NPC96216
0.8926	High Similarity	NPC184738
0.8926	High Similarity	NPC210425
0.8926	High Similarity	NPC189650
0.8926	High Similarity	NPC277426
0.8926	High Similarity	NPC474939
0.8926	High Similarity	NPC33653
0.8924	High Similarity	NPC474350
0.8912	High Similarity	NPC472600
0.8912	High Similarity	NPC168471
0.8912	High Similarity	NPC472601
0.891	High Similarity	NPC186113
0.891	High Similarity	NPC470339
0.8904	High Similarity	NPC94248
0.8904	High Similarity	NPC212693
0.8903	High Similarity	NPC54928
0.8897	High Similarity	NPC158481
0.8896	High Similarity	NPC477691
0.8889	High Similarity	NPC181523
0.8889	High Similarity	NPC227166
0.8889	High Similarity	NPC70016
0.8889	High Similarity	NPC215921
0.8889	High Similarity	NPC312549
0.8889	High Similarity	NPC258249
0.8889	High Similarity	NPC290671
0.8889	High Similarity	NPC209142
0.8882	High Similarity	NPC477573
0.8882	High Similarity	NPC329933
0.8882	High Similarity	NPC237440
0.8882	High Similarity	NPC1827
0.8882	High Similarity	NPC109827
0.8882	High Similarity	NPC124470
0.8882	High Similarity	NPC477572
0.8882	High Similarity	NPC477571
0.8882	High Similarity	NPC10576
0.8882	High Similarity	NPC10027
0.8882	High Similarity	NPC269420
0.8882	High Similarity	NPC70764
0.8882	High Similarity	NPC270160
0.8882	High Similarity	NPC65775
0.8875	High Similarity	NPC76647
0.8875	High Similarity	NPC234331
0.8874	High Similarity	NPC126767
0.8874	High Similarity	NPC56433
0.8874	High Similarity	NPC312929
0.8874	High Similarity	NPC190648
0.8874	High Similarity	NPC259632

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 NPC273483 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	972
0.2-0.3	1678
0.3-0.4	2523
0.4-0.5	1851
0.5-0.6	1111
0.6-0.7	461
0.7-0.8	183
0.8-0.85	39
0.85-0.9	10
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9122	High Similarity	NPD2532	Approved
0.9122	High Similarity	NPD2534	Approved
0.9122	High Similarity	NPD2533	Approved
0.902	High Similarity	NPD7819	Suspended
0.8844	High Similarity	NPD970	Clinical (unspecified phase)
0.8797	High Similarity	NPD6959	Discontinued
0.8742	High Similarity	NPD6232	Discontinued
0.8742	High Similarity	NPD4378	Clinical (unspecified phase)
0.8704	High Similarity	NPD5844	Phase 1
0.8654	High Similarity	NPD2393	Clinical (unspecified phase)
0.858	High Similarity	NPD7473	Discontinued
0.8526	High Similarity	NPD7411	Suspended
0.8516	High Similarity	NPD3226	Approved
0.8491	Intermediate Similarity	NPD7075	Discontinued
0.8462	Intermediate Similarity	NPD6599	Discontinued
0.8456	Intermediate Similarity	NPD2935	Discontinued
0.8456	Intermediate Similarity	NPD1551	Phase 2
0.8428	Intermediate Similarity	NPD7768	Phase 2
0.8418	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD5710	Approved
0.8395	Intermediate Similarity	NPD5711	Approved
0.8378	Intermediate Similarity	NPD1607	Approved
0.8365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD3750	Approved
0.8354	Intermediate Similarity	NPD1934	Approved
0.8354	Intermediate Similarity	NPD6801	Discontinued
0.8344	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD4380	Phase 2
0.8312	Intermediate Similarity	NPD6799	Approved
0.8293	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD2346	Discontinued
0.8267	Intermediate Similarity	NPD1510	Phase 2
0.8261	Intermediate Similarity	NPD3749	Approved
0.8258	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD3817	Phase 2
0.8243	Intermediate Similarity	NPD1240	Approved
0.8235	Intermediate Similarity	NPD4628	Phase 3
0.8231	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6559	Discontinued
0.8212	Intermediate Similarity	NPD2796	Approved
0.8199	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1511	Approved
0.8187	Intermediate Similarity	NPD2801	Approved
0.817	Intermediate Similarity	NPD2800	Approved
0.817	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1243	Approved
0.8153	Intermediate Similarity	NPD920	Approved
0.8148	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1512	Approved
0.8086	Intermediate Similarity	NPD3882	Suspended
0.8077	Intermediate Similarity	NPD7390	Discontinued
0.8075	Intermediate Similarity	NPD1465	Phase 2
0.8072	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6166	Phase 2
0.805	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3748	Approved
0.8026	Intermediate Similarity	NPD2799	Discontinued
0.8025	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7074	Phase 3
0.7976	Intermediate Similarity	NPD3818	Discontinued
0.7974	Intermediate Similarity	NPD6099	Approved
0.7974	Intermediate Similarity	NPD6100	Approved
0.7941	Intermediate Similarity	NPD5953	Discontinued
0.7939	Intermediate Similarity	NPD5494	Approved
0.7929	Intermediate Similarity	NPD7286	Phase 2
0.7929	Intermediate Similarity	NPD7054	Approved
0.7914	Intermediate Similarity	NPD5402	Approved
0.7911	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1203	Approved
0.7885	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7472	Approved
0.7879	Intermediate Similarity	NPD919	Approved
0.7867	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5408	Approved
0.7857	Intermediate Similarity	NPD5405	Approved
0.7857	Intermediate Similarity	NPD5406	Approved
0.7857	Intermediate Similarity	NPD5404	Approved
0.7852	Intermediate Similarity	NPD6832	Phase 2
0.7849	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7229	Phase 3
0.7836	Intermediate Similarity	NPD6797	Phase 2
0.7829	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5403	Approved
0.7803	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD8312	Approved
0.78	Intermediate Similarity	NPD4625	Phase 3
0.7791	Intermediate Similarity	NPD7251	Discontinued
0.7791	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD6651	Approved
0.7758	Intermediate Similarity	NPD4965	Approved
0.7758	Intermediate Similarity	NPD4966	Approved
0.7758	Intermediate Similarity	NPD4967	Phase 2
0.775	Intermediate Similarity	NPD6273	Approved
0.7748	Intermediate Similarity	NPD2313	Discontinued
0.7748	Intermediate Similarity	NPD411	Approved
0.7746	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7808	Phase 3
0.7733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD230	Phase 1
0.7703	Intermediate Similarity	NPD1283	Approved
0.7688	Intermediate Similarity	NPD5401	Approved
0.7687	Intermediate Similarity	NPD9717	Approved
0.7687	Intermediate Similarity	NPD1608	Approved
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7199	Phase 2
0.7677	Intermediate Similarity	NPD7033	Discontinued
0.7677	Intermediate Similarity	NPD4308	Phase 3
0.7665	Intermediate Similarity	NPD6234	Discontinued
0.7661	Intermediate Similarity	NPD7177	Discontinued
0.7658	Intermediate Similarity	NPD7003	Approved
0.7651	Intermediate Similarity	NPD2797	Approved
0.7647	Intermediate Similarity	NPD4060	Phase 1
0.7647	Intermediate Similarity	NPD2979	Phase 3
0.7632	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3268	Approved
0.7619	Intermediate Similarity	NPD422	Phase 1
0.7603	Intermediate Similarity	NPD4626	Approved
0.7597	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5124	Phase 1
0.7597	Intermediate Similarity	NPD447	Suspended
0.758	Intermediate Similarity	NPD2344	Approved
0.7566	Intermediate Similarity	NPD7783	Phase 2
0.7566	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD8151	Discontinued
0.7534	Intermediate Similarity	NPD5691	Approved
0.7516	Intermediate Similarity	NPD4477	Approved
0.7516	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4476	Approved
0.7515	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1281	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7485	Intermediate Similarity	NPD4288	Approved
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD17	Approved
0.7473	Intermediate Similarity	NPD7435	Discontinued
0.7472	Intermediate Similarity	NPD8150	Discontinued
0.7471	Intermediate Similarity	NPD1247	Approved
0.7457	Intermediate Similarity	NPD7228	Approved
0.7419	Intermediate Similarity	NPD4307	Phase 2
0.7419	Intermediate Similarity	NPD943	Approved
0.7418	Intermediate Similarity	NPD4363	Phase 3
0.7418	Intermediate Similarity	NPD4360	Phase 2
0.7405	Intermediate Similarity	NPD6780	Approved
0.7405	Intermediate Similarity	NPD6778	Approved
0.7405	Intermediate Similarity	NPD2438	Suspended
0.7405	Intermediate Similarity	NPD6782	Approved
0.7405	Intermediate Similarity	NPD6781	Approved
0.7405	Intermediate Similarity	NPD6777	Approved
0.7405	Intermediate Similarity	NPD6776	Approved
0.7405	Intermediate Similarity	NPD6779	Approved
0.7403	Intermediate Similarity	NPD3764	Approved
0.74	Intermediate Similarity	NPD4749	Approved
0.7391	Intermediate Similarity	NPD2309	Approved
0.7384	Intermediate Similarity	NPD3926	Phase 2
0.7383	Intermediate Similarity	NPD1610	Phase 2
0.7383	Intermediate Similarity	NPD1611	Approved
0.7383	Intermediate Similarity	NPD1201	Approved
0.7378	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8434	Phase 2
0.7368	Intermediate Similarity	NPD1019	Discontinued
0.7368	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1778	Approved
0.7362	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6005	Phase 3
0.7358	Intermediate Similarity	NPD6004	Phase 3
0.7358	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6002	Phase 3
0.7356	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD3225	Approved
0.7347	Intermediate Similarity	NPD9545	Approved
0.7337	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3787	Discontinued
0.7312	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1613	Approved
0.7303	Intermediate Similarity	NPD1470	Approved
0.7303	Intermediate Similarity	NPD3266	Approved
0.7303	Intermediate Similarity	NPD1164	Approved
0.7303	Intermediate Similarity	NPD3267	Approved
0.7301	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1651	Approved
0.7296	Intermediate Similarity	NPD2531	Phase 2
0.7293	Intermediate Similarity	NPD4287	Approved
0.729	Intermediate Similarity	NPD1296	Phase 2
0.7287	Intermediate Similarity	NPD7696	Phase 3
0.7287	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD7697	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