NPASS Compound

Structure

NPC148416 OpenBabel06302215332D 31 34 0 0 1 0 0 0 0 0999 V2000 0.5000 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6962 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6962 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5622 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5622 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1962 -0.0000 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 1 2 1 0 0 0 0 2 7 2 0 0 0 0 2 3 1 0 0 0 0 3 4 2 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 8 5 1 1 0 0 0 8 9 1 0 0 0 0 8 31 1 0 0 0 0 9 10 1 6 0 0 0 9 31 1 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 13 14 1 6 0 0 0 13 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 6 0 0 0 16 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 21 30 1 0 0 0 0 22 23 1 6 0 0 0 22 30 1 0 0 0 0 23 29 2 0 0 0 0 23 24 1 0 0 0 0 24 25 2 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 26 28 2 0 0 0 0 28 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.27
Volume:	472.403
LogP:	7.175
LogD:	4.973
LogS:	-6.84
# Rotatable Bonds:	10
TPSA:	25.06
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	4.379
Fsp3:	0.448
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.753
MDCK Permeability:	2.0105424482608214e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.458
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	97.7262191772461%
Volume Distribution (VD):	1.293
Pgp-substrate:	2.181868553161621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.587
CYP2C19-inhibitor:	0.829
CYP2C19-substrate:	0.369
CYP2C9-inhibitor:	0.763
CYP2C9-substrate:	0.258
CYP2D6-inhibitor:	0.719
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.642

ADMET: Excretion

Clearance (CL):	10.321
Half-life (T1/2):	0.004

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.16
Rat Oral Acute Toxicity:	0.488
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.026
Carcinogencity:	0.634
Eye Corrosion:	0.004
Eye Irritation:	0.724
Respiratory Toxicity:	0.208

Download Data

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

Natural Product: NPC148416

Natural Product ID:	NPC148416
*Common Name:**	CTHDLZOITPXSJS-KLXXULICSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CTHDLZOITPXSJS-KLXXULICSA-N
Standard InCHI:	InChI=1S/C29H36O2/c1-18-7-11-24(12-8-18)28-26(30-28)16-22(5)20(3)15-21(4)23(6)17-27-29(31-27)25-13-9-19(2)10-14-25/h7-14,20-21,26-29H,5-6,15-17H2,1-4H3/t20-,21+,26-,27-,28-,29-/m0/s1
SMILES:	Cc1ccc(cc1)[C@H]1[C@H](CC(=C)[C@@H](C)C[C@@H](C)C(=C)C[C@H]2[C@H](c3ccc(C)cc3)O2)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001091] Toluenes

*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
NPO4562	Lonchocarpus urucu	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10075742]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[32786878]
NPO6017	Artemisia arbuscula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6017	Artemisia arbuscula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13443	Doris montereyensis	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9094	Citrus reshni	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO378	Myristica argentea	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO790	Cybister confusus	Species	Dytiscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2622	Cheilanthes mysurensis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1477	Egregia menziesii	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4562	Lonchocarpus urucu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8794	Aconitum fauriei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO182	Cylas formicarius	Species	Brentidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6559	Duddingtonia flagrans	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9234	Cynoctonum wilfordii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6017	Artemisia arbuscula	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

☑ 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 NPC148416 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	361
0.1-0.2	1421
0.2-0.3	3767
0.3-0.4	13304
0.4-0.5	12965
0.5-0.6	9329
0.6-0.7	1519
0.7-0.8	31
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
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 NPC148416 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	978
0.2-0.3	1216
0.3-0.4	3297
0.4-0.5	2136
0.5-0.6	1046
0.6-0.7	164
0.7-0.8	9
0.8-0.85	0
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