NPASS Compound

Structure

NPC250147 OpenBabel06302216112D 36 37 0 0 1 0 0 0 0 0999 V2000 -4.2997 -1.3059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2469 -1.3059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7205 -2.2176 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2469 -3.1293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6678 -2.2176 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1414 -1.3059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0886 -1.3059 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4378 -0.3942 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9980 -0.5762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8880 -1.6232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0738 -2.0514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7397 -2.2420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5838 -0.5146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0940 -0.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0057 0.3063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0057 1.3591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0940 1.8854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1823 1.3591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1823 0.3063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5838 2.1800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9980 2.2416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4378 2.0595 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2396 1.1272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2694 1.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5947 2.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8902 3.1297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6244 2.5662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2396 0.5381 0.0000 N 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 -0.8517 -0.6188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8517 2.2842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6678 -0.3942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1414 -3.1293 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6678 -4.0411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0886 -3.1293 0.0000 C 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 4 1 1 0 0 0 3 5 1 0 0 0 0 5 6 1 1 0 0 0 5 34 1 0 0 0 0 6 7 2 3 0 0 0 6 33 1 0 0 0 0 8 7 1 6 0 0 0 8 9 1 0 0 0 0 8 30 1 0 0 0 0 9 10 1 1 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 13 14 1 0 0 0 0 14 19 2 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 20 21 2 0 0 0 0 21 22 1 0 0 0 0 22 23 2 3 0 0 0 23 24 1 0 0 0 0 23 32 1 0 0 0 0 24 25 1 1 0 0 0 24 29 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 29 30 2 3 0 0 0 30 31 1 0 0 0 0 34 35 1 0 0 0 0 34 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.34
Volume:	536.424
LogP:	4.04
LogD:	4.343
LogS:	-4.242
# Rotatable Bonds:	8
TPSA:	100.1
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.599
Synthetic Accessibility Score:	5.731
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.148
MDCK Permeability:	1.023219374474138e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.158
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.199

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.326
Plasma Protein Binding (PPB):	79.21819305419922%
Volume Distribution (VD):	1.32
Pgp-substrate:	5.756841659545898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.801
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.873
CYP2C9-substrate:	0.575
CYP2D6-inhibitor:	0.233
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.72

ADMET: Excretion

Clearance (CL):	8.497
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.535
Human Hepatotoxicity (H-HT):	0.695
Drug-inuced Liver Injury (DILI):	0.797
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.401
Maximum Recommended Daily Dose:	0.383
Skin Sensitization:	0.048
Carcinogencity:	0.236
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC250147

Natural Product ID:	NPC250147
*Common Name:**	ULQXKOIGVXLOOC-RJJCKBEYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ULQXKOIGVXLOOC-RJJCKBEYSA-N
Standard InCHI:	InChI=1S/C28H44N4O4/c1-9-19(6)24(32(7)8)28(35)31-23-25(18(4)5)36-21-12-10-20(11-13-21)14-15-29-26(33)22(16-17(2)3)30-27(23)34/h10-15,17-19,22-25H,9,16H2,1-8H3,(H,29,33)(H,30,34)(H,31,35)/b15-14-/t19-,22-,23-,24-,25-/m0/s1
SMILES:	CC[C@H](C)[C@@H](C(=N[C@H]1[C@H](C(C)C)Oc2ccc(cc2)/C=CN=C([C@H](CC(C)C)N=C1O)O)O)N(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	5281587
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO25301	Angylocalyx pynaertii	Species	Fabaceae	Eukaryota	pods	n.a.	n.a.	PMID[11858756]
NPO23049	Methanocaldococcus jannaschii	Species	Methanocaldococcaceae	Archaea	n.a.	n.a.	n.a.	PMID[24977328]
NPO23049	Methanocaldococcus jannaschii	Species	Methanocaldococcaceae	Archaea	n.a.	n.a.	n.a.	PMID[26100040]
NPO25301	Angylocalyx pynaertii	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8229017]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24625	Fannia canicularis	Species	Fanniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24913	Licania densiflora	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23602	Aspergillus parvulus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7271	Stachys affinis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24061	Zanthoxylum pistaciiflorum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23355	Astragalus arguricus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24546	Diospyros siamang	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23560	Peridinium foliaceum	Species	Peridiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23521	Christiana africana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25213	Physcia endococcina	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24784	Forsythia ovata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25301	Angylocalyx pynaertii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23644	Clitoria ternatea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24751	Swartzia arborescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24584	Corydalis bungeana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23049	Methanocaldococcus jannaschii	Species	Methanocaldococcaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO24467	Silene italica	Species	Caryophyllaceae	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 NPC250147 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	161
0.1-0.2	1299
0.2-0.3	8386
0.3-0.4	9573
0.4-0.5	9312
0.5-0.6	11505
0.6-0.7	2270
0.7-0.8	175
0.8-0.85	6
0.85-0.9	0
0.9-0.95	9
0.95-1	1

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 NPC250147 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	117
0.1-0.2	504
0.2-0.3	1112
0.3-0.4	1970
0.4-0.5	2755
0.5-0.6	1874
0.6-0.7	694
0.7-0.8	122
0.8-0.85	2
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