NPASS Compound

Structure

NPC156448 OpenBabel06302216122D 28 31 0 0 1 0 0 0 0 0999 V2000 -5.4912 0.6664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8221 1.4095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8439 1.2016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5349 0.2505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5568 0.0426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8876 0.7858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1966 1.7368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1748 1.9447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4838 2.8958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4619 3.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9095 0.5779 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5027 -0.3357 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7106 -1.3138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1554 -1.8138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8985 -1.1447 0.0000 C 0 0 2 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 0.0000 -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 -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 -1.7321 -0.0000 0.0000 O 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4918 -0.2312 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6997 0.7470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1663 1.2470 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 8 2 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 2 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 11 6 1 1 0 0 0 11 12 1 0 0 0 0 11 28 1 0 0 0 0 12 13 1 1 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 1 0 0 0 15 26 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 24 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 22 23 1 0 0 0 0 24 25 1 0 0 0 0 26 27 1 1 0 0 0 27 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.17
Volume:	391.765
LogP:	2.919
LogD:	3.173
LogS:	-3.972
# Rotatable Bonds:	6
TPSA:	55.38
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	3.488
Fsp3:	0.455
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:	-4.817
MDCK Permeability:	6.866761395940557e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.106
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.102

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	68.1998519897461%
Volume Distribution (VD):	0.712
Pgp-substrate:	9.523994445800781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.254
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.718
CYP2D6-inhibitor:	0.111
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.773
CYP3A4-substrate:	0.838

ADMET: Excretion

Clearance (CL):	11.928
Half-life (T1/2):	0.226

ADMET: Toxicity

hERG Blockers:	0.604
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.378
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.17
Skin Sensitization:	0.926
Carcinogencity:	0.508
Eye Corrosion:	0.004
Eye Irritation:	0.222
Respiratory Toxicity:	0.469

Download Data

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

Natural Product: NPC156448

Natural Product ID:	NPC156448
*Common Name:**	PEUUVVGQIVMSAW-AHWCRGGASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PEUUVVGQIVMSAW-AHWCRGGASA-N
Standard InCHI:	InChI=1S/C22H26O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-28-22(16(15)12-27-21)14-6-8-18(24-2)20(10-14)26-4/h5-10,15-16,21-22H,11-12H2,1-4H3/t15-,16-,21-,22-/m1/s1
SMILES:	COc1ccc(cc1OC)[C@@H]1[C@@H]2CO[C@H](c3ccc(c(c3)OC)OC)[C@@H]2CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11870582
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[17628872]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19370929]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[7779269]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30858	Atractylodes japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21741	Araucaria angustifolia	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27299	Litsea gracilipes	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29814	Haplophyllum	Genus	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10821	Magnolia praecocissima	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21741	Araucaria angustifolia	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10821	Magnolia praecocissima	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27299	Litsea gracilipes	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28920	Haplophyllum sp.	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21741	Araucaria angustifolia	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30858	Atractylodes japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27299	Litsea gracilipes	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21741	Araucaria angustifolia	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10821	Magnolia praecocissima	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27299	Litsea gracilipes	Species	Lauraceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC156448 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	464
0.1-0.2	1396
0.2-0.3	3776
0.3-0.4	11545
0.4-0.5	7717
0.5-0.6	6724
0.6-0.7	8463
0.7-0.8	2132
0.8-0.85	311
0.85-0.9	106
0.9-0.95	52
0.95-1	11

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 NPC156448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	840
0.2-0.3	1610
0.3-0.4	2836
0.4-0.5	1861
0.5-0.6	1046
0.6-0.7	524
0.7-0.8	64
0.8-0.85	3
0.85-0.9	0
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