NPASS Compound

Structure

NPC54957 OpenBabel06302216162D 21 24 0 0 1 0 0 0 0 0999 V2000 3.1833 -0.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3754 -0.5890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5571 -0.1166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7388 -0.5890 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7388 -1.5339 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7388 -2.4189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5571 -2.0063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3754 -1.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -2.1230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1493 -2.9954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9210 -1.9129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3310 -1.0616 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9212 -0.2101 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1356 -1.0102 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2900 -0.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1004 -0.5391 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 -2.2760 -1.0617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3746 -2.0015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2378 -2.3859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6101 -2.5568 0.0000 C 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 4 3 1 6 0 0 0 4 5 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 1 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 7 8 1 0 0 0 0 9 14 1 0 0 0 0 9 10 1 6 0 0 0 9 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 1 0 0 0 13 14 1 0 0 0 0 13 17 1 1 0 0 0 14 16 1 0 0 0 0 14 15 1 1 0 0 0 15 16 1 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	722.16
Volume:	692.892
LogP:	4.694
LogD:	2.787
LogS:	-3.519
# Rotatable Bonds:	6
TPSA:	236.06
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	8
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.068
Synthetic Accessibility Score:	5.568
Fsp3:	0.154
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.655
MDCK Permeability:	7.604724487464409e-06
Pgp-inhibitor:	0.122
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.46
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	96.62224578857422%
Volume Distribution (VD):	0.237
Pgp-substrate:	3.3362653255462646%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.133
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.837
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.156
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	9.232
Half-life (T1/2):	0.655

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.386
Rat Oral Acute Toxicity:	0.634
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.96
Carcinogencity:	0.393
Eye Corrosion:	0.003
Eye Irritation:	0.908
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC54957

Natural Product ID:	NPC54957
*Common Name:**	OZXJPPYWZVBMGW-IKIFYQGPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OZXJPPYWZVBMGW-IKIFYQGPSA-N
Standard InCHI:	InChI=1S/C17H24O4/c1-10-5-6-15(3)13(7-10)21-14-12(20-11(2)18)8-16(15,4)17(14)9-19-17/h7,12-14H,5-6,8-9H2,1-4H3/t12-,13-,14-,15+,16-,17+/m1/s1
SMILES:	CC1=C[C@@H]2[C@](C)(CC1)[C@@]1(C)C[C@H]([C@H]([C@]31CO3)O2)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	14733837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO28075	Crataegus sanguinea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20735	Aconitum balfourii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28075	Crataegus sanguinea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20735	Aconitum balfourii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28657	Incarvillea mairei	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29355	Asaemia axillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24825	Colchicum bulbocodium	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28237	Miconia langsdorffii	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23154	Paysonia grandiflora	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27920	Piper kwashoense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28355	Pseudocyphellaria crocata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20735	Aconitum balfourii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28075	Crataegus sanguinea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28249	Macaranga pleiostemon	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27977	Crotalaria verrucosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28692	Pteris undulata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28673	Cucumaria echinata	Species	Cucumariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28547	Arthrocnemum glaucum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28285	Taxus harringtonia	Species	Taxaceae	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 NPC54957 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	207
0.1-0.2	1482
0.2-0.3	5684
0.3-0.4	15241
0.4-0.5	8364
0.5-0.6	7633
0.6-0.7	3742
0.7-0.8	282
0.8-0.85	20
0.85-0.9	24
0.9-0.95	16
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 NPC54957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1789
0.2-0.3	4235
0.3-0.4	2127
0.4-0.5	477
0.5-0.6	255
0.6-0.7	99
0.7-0.8	1
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