NPASS Compound

Structure

NPC83122 OpenBabel06302215262D 37 42 0 0 1 0 0 0 0 0999 V2000 -3.8182 -1.3159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0584 -0.8773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2890 -1.3215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5195 -0.8773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5195 0.0113 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2890 0.4555 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5292 0.8942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0584 0.0113 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8279 0.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8279 1.3441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5877 1.7827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0584 1.7883 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1906 2.6670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5861 3.3183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7001 3.2517 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3471 4.0406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1307 2.2894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8051 1.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4858 1.1839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7676 2.5550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1998 2.5175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4618 1.6685 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2890 1.3441 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8283 1.0804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7597 0.4499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7597 -1.3159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.8773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7597 -1.3159 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5195 -0.8773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5195 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7597 0.4386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7597 1.3159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5195 1.7545 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 2.2792 0.4386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2792 -1.3159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7597 -2.1932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 8 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 4 26 1 0 0 0 0 5 6 1 0 0 0 0 5 25 1 0 0 0 0 6 23 1 0 0 0 0 6 7 1 6 0 0 0 6 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 12 23 1 0 0 0 0 12 13 1 6 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 21 1 0 0 0 0 15 16 1 1 0 0 0 15 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 18 20 1 0 0 0 0 21 20 1 1 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 27 34 1 0 0 0 0 28 29 1 0 0 0 0 28 37 1 1 0 0 0 29 30 1 0 0 0 0 29 36 1 6 0 0 0 30 31 1 0 0 0 0 30 35 1 1 0 0 0 31 32 1 6 0 0 0 31 34 1 0 0 0 0 32 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	216.12
Volume:	243.905
LogP:	2.896
LogD:	3.079
LogS:	-3.321
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.759
Synthetic Accessibility Score:	2.803
Fsp3:	0.143
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:	-4.667
MDCK Permeability:	1.9762079318752512e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.51
Plasma Protein Binding (PPB):	93.87000274658203%
Volume Distribution (VD):	0.458
Pgp-substrate:	4.538804054260254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.476
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	11.934
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.21
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.638
Rat Oral Acute Toxicity:	0.148
Maximum Recommended Daily Dose:	0.761
Skin Sensitization:	0.956
Carcinogencity:	0.508
Eye Corrosion:	0.312
Eye Irritation:	0.989
Respiratory Toxicity:	0.815

Download Data

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

Natural Product: NPC83122

Natural Product ID:	NPC83122
*Common Name:**	XKHBVJKBHHZGGQ-FUDFEDLXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XKHBVJKBHHZGGQ-FUDFEDLXSA-N
Standard InCHI:	InChI=1S/C25H34O12/c1-8-4-10(35-22-15(30)14(29)13(28)11(6-26)36-22)19(32)23(2)9(8)5-12(27)25-7-34-24(3)18(25)21(33)37-20(24)16(31)17(23)25/h4,9-11,13-20,22,26,28-32H,5-7H2,1-3H3/t9-,10-,11+,13+,14-,15+,16+,17+,18-,19+,20-,22+,23-,24-,25+/m0/s1
SMILES:	CC1=C[C@@H]([C@H]([C@@]2(C)[C@H]1CC(=O)[C@]13CO[C@@]4(C)[C@@H]3C(=O)O[C@H]4[C@@H]([C@H]21)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	102585875
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO23869	Basella alba	Species	Basellaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23869	Basella alba	Species	Basellaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23869	Basella alba	Species	Basellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23869	Basella alba	Species	Basellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1129	Punctularia atropurpurascens	Species	Punctulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27970	Desmonostoc muscorum	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11660	Qualea paraensis	Species	Vochysiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6551	Lythrum lanceolatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11902	Gomphocarpus fruticosus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4438	Austrobrickellia patens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2230	Fusarium sporotrichiella	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10692	Euryops othonnoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3635	Omphalotus olearius	Species	Omphalotaceae	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 NPC83122 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	287
0.1-0.2	1549
0.2-0.3	4483
0.3-0.4	7460
0.4-0.5	11551
0.5-0.6	8284
0.6-0.7	5433
0.7-0.8	3060
0.8-0.85	502
0.85-0.9	87
0.9-0.95	1
0.95-1	0

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 NPC83122 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	1748
0.2-0.3	3799
0.3-0.4	2145
0.4-0.5	653
0.5-0.6	328
0.6-0.7	175
0.7-0.8	49
0.8-0.85	6
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