NPASS Compound

Structure

NPC483497 OpenBabel06302215482D 30 33 0 0 1 0 0 0 0 0999 V2000 3.1551 -5.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6551 -4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 -3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -3.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7770 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7281 -1.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4712 -0.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2633 0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3122 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4223 -1.2361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4135 1.9456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6045 2.5334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3271 2.3523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2226 1.3578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 O 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 0.9511 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 12 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 11 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 13 14 1 0 0 0 0 14 29 1 0 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 21 2 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 6 0 0 0 23 28 1 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 28 29 1 0 0 0 0 29 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.14
Volume:	409.942
LogP:	4.073
LogD:	2.961
LogS:	-3.961
# Rotatable Bonds:	4
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.664
Synthetic Accessibility Score:	3.489
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.319
MDCK Permeability:	2.1335250494303182e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.201
30% Bioavailability (F30%):	0.404

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	99.49422454833984%
Volume Distribution (VD):	0.424
Pgp-substrate:	0.6574727296829224%

ADMET: Metabolism

CYP1A2-inhibitor:	0.583
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.657
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.821
CYP2C9-substrate:	0.274
CYP2D6-inhibitor:	0.353
CYP2D6-substrate:	0.233
CYP3A4-inhibitor:	0.292
CYP3A4-substrate:	0.575

ADMET: Excretion

Clearance (CL):	1.687
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.354
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.335
Carcinogencity:	0.181
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.133

Download Data

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

Natural Product: NPC483497

Natural Product ID:	NPC483497
*Common Name:**	MVHXVQPFCOSYOK-QHCPKHFHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MVHXVQPFCOSYOK-QHCPKHFHSA-N
Standard InCHI:	InChI=1S/C23H22O7/c1-22(2)10-9-15-11-13(3-8-18(15)29-22)12-17-19(14-4-6-16(24)7-5-14)23(28,21(26)27)30-20(17)25/h3-8,11,24,28H,9-10,12H2,1-2H3,(H,26,27)/t23-/m0/s1
SMILES:	CC1(C)CCc2cc(ccc2O1)CC1=C(c2ccc(cc2)O)[C@](C(=O)O)(O)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	132577716
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO40445	Aspergillus flavipes HN4-13	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27933892]

☑ 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	3
Ki	2
Others	7

Activity Type	# Activity
Cell Line	6
Others	5
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI	<	34.0	%	PMID[27933892]
NPT65	Cell Line	HepG2	Homo sapiens	GI	<	34.0	%	PMID[27933892]
NPT15	Cell Line	Jurkat	Homo sapiens	GI	<	34.0	%	PMID[27933892]
NPT81	Cell Line	A549	Homo sapiens	GI	<	34.0	%	PMID[27933892]
NPT111	Cell Line	K562	Homo sapiens	GI	<	34.0	%	PMID[27933892]
NPT492	Cell Line	Caco-2	Homo sapiens	CC50	>	800000.0	nM	PMID[27933892]
NPT2	Others	Unspecified		IC50	=	95000.0	nM	PMID[27933892]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	8.5	n.a.	PMID[27933892]
NPT2	Others	Unspecified		Ki	=	4700.0	nM	PMID[27933892]
NPT2	Others	Unspecified		Ki	=	9200.0	nM	PMID[27933892]
NPT20648	PROTEIN FAMILY	Alpha glucosidase	Homo sapiens	IC50	=	7630.0	nM	PMID[29295795]
NPT35	Others	n.a.		IC50	>	200000.0	nM	PMID[29295795]

☑ 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 NPC483497 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	315
0.1-0.2	1422
0.2-0.3	3520
0.3-0.4	8642
0.4-0.5	10101
0.5-0.6	3963
0.6-0.7	10059
0.7-0.8	4631
0.8-0.85	29
0.85-0.9	9
0.9-0.95	2
0.95-1	4

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 NPC483497 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	892
0.2-0.3	1414
0.3-0.4	2492
0.4-0.5	2098
0.5-0.6	1212
0.6-0.7	623
0.7-0.8	135
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
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