NPASS Compound

Structure

NPC85446 OpenBabel06302216222D 31 35 0 0 1 0 0 0 0 0999 V2000 -0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -0.4861 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6839 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5259 -0.4861 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5259 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3679 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2098 -1.4583 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.0518 -1.9444 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.2098 -2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0518 -2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8938 -3.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7358 -2.9167 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.5777 -3.4028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7358 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2219 -1.1025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7080 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8938 -1.4583 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.8938 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0518 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2098 -0.4861 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.2098 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3679 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.2098 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3679 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 0.9722 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6839 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9722 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 0.8420 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 30 1 0 0 0 0 2 3 1 0 0 0 0 3 26 1 0 0 0 0 3 4 1 0 0 0 0 4 22 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 20 1 0 0 0 0 7 8 1 0 0 0 0 8 17 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 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 22 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 28 29 1 0 0 0 0 29 30 2 0 0 0 0 30 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.39
Volume:	490.807
LogP:	7.49
LogD:	5.545
LogS:	-6.106
# Rotatable Bonds:	0
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	4.792
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.955
MDCK Permeability:	7.05319371263613e-06
Pgp-inhibitor:	0.065
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.904
30% Bioavailability (F30%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.582
Plasma Protein Binding (PPB):	100.08070373535156%
Volume Distribution (VD):	2.359
Pgp-substrate:	1.9509226083755493%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.448
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.965
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.095
CYP2D6-substrate:	0.803
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.595

ADMET: Excretion

Clearance (CL):	20.494
Half-life (T1/2):	0.009

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.31
Maximum Recommended Daily Dose:	0.784
Skin Sensitization:	0.465
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.091
Respiratory Toxicity:	0.667

Download Data

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

Natural Product: NPC85446

Natural Product ID:	NPC85446
*Common Name:**	NGFFRJBGMSPDMS-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NGFFRJBGMSPDMS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h11,20-25,31H,9-10,12-18H2,1-8H3
SMILES:	CC1=CCC2(C)CCC3(C)C(CCC4C5(C)CCC(C(C)(C)C5CCC34C)O)C2C1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	604983
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473446]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	Whole plant	Songyang County, Zhejiang Province, China	n.a.	PMID[15387644]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23706	Breea segeta	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11697	Cirsium setosum	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
NPO22234	NPC85446	Other (raw)	Leaf	9250	4300	14200	mg/100g	Database [DUKE]

☑ 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 NPC85446 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	212
0.1-0.2	1933
0.2-0.3	8365
0.3-0.4	16371
0.4-0.5	6344
0.5-0.6	4788
0.6-0.7	3337
0.7-0.8	969
0.8-0.85	237
0.85-0.9	101
0.9-0.95	13
0.95-1	27

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 NPC85446 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	2164
0.2-0.3	4232
0.3-0.4	1825
0.4-0.5	356
0.5-0.6	192
0.6-0.7	141
0.7-0.8	13
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

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