NPASS Compound

Structure

NPC164044 OpenBabel06302216032D 22 25 0 0 1 0 0 0 0 0999 V2000 3.2485 1.8752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2484 0.9013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0499 0.4385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0498 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2483 -0.9498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2482 -1.8754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4466 -2.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6451 -1.8756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6450 -0.9497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4468 -0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4465 0.4385 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6451 0.9013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 -0.4870 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8435 -1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 -1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6870 -1.9480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 -0.4870 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 0.8017 -2.3626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4466 -3.2638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9094 -4.0653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 11 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 10 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 7 21 1 0 0 0 0 8 9 2 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 1 0 0 0 12 13 1 0 0 0 0 13 19 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 18 19 2 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	297.14
Volume:	307.207
LogP:	1.327
LogD:	1.181
LogS:	-1.421
# Rotatable Bonds:	1
TPSA:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.864
Synthetic Accessibility Score:	4.102
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.692
MDCK Permeability:	2.6725048883236013e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	91.69324493408203%
Volume Distribution (VD):	1.057
Pgp-substrate:	4.1716413497924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.543
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.669
CYP2D6-inhibitor:	0.334
CYP2D6-substrate:	0.667
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.825

ADMET: Excretion

Clearance (CL):	5.892
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.512
Human Hepatotoxicity (H-HT):	0.42
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.346
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.865
Carcinogencity:	0.914
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC164044

Natural Product ID:	NPC164044
*Common Name:**	PNJUPRNTSWJWAX-CYBMUJFWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PNJUPRNTSWJWAX-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C18H19NO3/c1-19-8-5-11-9-14(22-2)17(21)16-15(11)13(19)10-18(16)6-3-12(20)4-7-18/h3-4,6-7,9,13,21H,5,8,10H2,1-2H3/t13-/m1/s1
SMILES:	CN1CCc2cc(c(c3c2[C@H]1CC13C=CC(=O)C=C1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	442245
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002660] Proaporphines

*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
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[9599253]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868142]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19361	Herba meconpsis integrifoliae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO628	Schisandra nigra	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2058	Sideritis discolor	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO189	Pachypodium lealii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20755	Ballota hirsuta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2256	Pseudaxinyssa cantharella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO628	Schisandra nigra	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO413	Astragalus prusianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3183	Phalaenopsis equestris	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8841	Shorea leprosula	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4921	Brickellia diffusa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23324	Porphyridium purpureum	Species	Porphyridiaceae	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 NPC164044 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	277
0.1-0.2	1494
0.2-0.3	5246
0.3-0.4	12347
0.4-0.5	5370
0.5-0.6	13100
0.6-0.7	4082
0.7-0.8	616
0.8-0.85	122
0.85-0.9	37
0.9-0.95	4
0.95-1	2

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 NPC164044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	732
0.2-0.3	974
0.3-0.4	2132
0.4-0.5	2713
0.5-0.6	1731
0.6-0.7	577
0.7-0.8	95
0.8-0.85	7
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