NPASS Compound

Structure

NPC488672 OpenBabel06302215512D 27 29 0 0 1 0 0 0 0 0999 V2000 -3.1925 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3943 -0.4608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7981 0.4608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7981 1.3824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1945 0.9860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4090 0.4682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4090 -0.0923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1945 -0.6102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7981 -1.0066 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2803 -1.2211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2803 -1.2211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7981 -1.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1945 -0.6102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4090 -0.0923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4090 0.4682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8948 -0.1650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5894 -0.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1945 0.9860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7981 1.3824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7981 0.4608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3943 -0.4608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1925 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4601 -2.1249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3101 -1.7728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 22 2 0 0 0 0 3 4 1 0 0 0 0 4 20 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 9 27 1 1 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 1 0 0 0 12 17 2 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 22 23 1 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	380.389
LogP:	3.108
LogD:	2.602
LogS:	-4.11
# Rotatable Bonds:	2
TPSA:	88.38
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	5.28
Fsp3:	0.333
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:	-4.858
MDCK Permeability:	1.3091894288663752e-05
Pgp-inhibitor:	0.103
Pgp-substrate:	0.928
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.425

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	97.7850570678711%
Volume Distribution (VD):	0.554
Pgp-substrate:	7.836529731750488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.463
CYP1A2-substrate:	0.883
CYP2C19-inhibitor:	0.129
CYP2C19-substrate:	0.815
CYP2C9-inhibitor:	0.147
CYP2C9-substrate:	0.482
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.391
CYP3A4-substrate:	0.489

ADMET: Excretion

Clearance (CL):	12.921
Half-life (T1/2):	0.606

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.419
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.709
Carcinogencity:	0.923
Eye Corrosion:	0.003
Eye Irritation:	0.079
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC488672

Natural Product ID:	NPC488672
*Common Name:**	ATGCIUOLONYVDU-XQONNYOLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ATGCIUOLONYVDU-XQONNYOLSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-25-20-14-5-3-4-6-15(22)12-17(23)13-7-9-16(10-8-13)27-18(11-14)21(26-2)19(20)24/h3,5,7-11,15,17,22-24H,4,6,12H2,1-2H3/b5-3-/t15-,17-/m0/s1
SMILES:	COc1c2/C=CCC[C@@H](C[C@@H](c3ccc(cc3)Oc(c2)c(c1O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	127026084
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003523] Meta,para-diphenylether diarylheptanoids

*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
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Shells; Leaves	n.a.	n.a.	PMID[18163585]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25420236]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26606246]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Green Leafy Covers	n.a.	n.a.	PMID[28520428]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12631	Corylus avellana	Species	Betulaceae	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
EC50	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell Line	U2OS	Homo sapiens	EC50	>	150000.0	nM	PMID[26606246]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	150000.0	nM	PMID[26606246]

☑ 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 NPC488672 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	433
0.1-0.2	1582
0.2-0.3	5094
0.3-0.4	12763
0.4-0.5	5022
0.5-0.6	4245
0.6-0.7	6222
0.7-0.8	5491
0.8-0.85	1009
0.85-0.9	567
0.9-0.95	247
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID

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 NPC488672 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	890
0.2-0.3	2013
0.3-0.4	2732
0.4-0.5	1516
0.5-0.6	865
0.6-0.7	630
0.7-0.8	141
0.8-0.85	7
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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