NPASS Compound

Structure

NPC43577 OpenBabel06302215472D 23 24 0 0 1 0 0 0 0 0999 V2000 2.3548 4.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8509 3.3810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8929 3.4097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4388 4.2537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3890 2.5944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5689 2.6232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8431 1.7504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4272 0.8870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0247 0.1376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8113 -0.7967 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0521 -1.2125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9156 -0.7966 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1289 0.1378 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5312 0.8870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 3 3 0 0 0 0 0 0 0 0 0 0.2080 0.4317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6650 -1.3942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2363 -2.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2795 -2.3087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7643 -3.0513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3356 -3.9085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8636 -4.7084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 -2.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 8 7 1 1 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 10 9 1 1 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 6 0 0 0 13 14 1 1 0 0 0 13 15 1 0 0 0 0 15 16 1 0 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 18 20 1 0 0 0 0 20 21 2 0 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 M CHG 1 15 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	321.19
Volume:	338.383
LogP:	2.415
LogD:	1.752
LogS:	-2.289
# Rotatable Bonds:	6
TPSA:	55.84
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	4.931
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.592
MDCK Permeability:	3.2783478673081845e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.1
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.281
Plasma Protein Binding (PPB):	56.213165283203125%
Volume Distribution (VD):	2.434
Pgp-substrate:	31.380722045898438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.315
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.332
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.92
CYP2D6-substrate:	0.377
CYP3A4-inhibitor:	0.876
CYP3A4-substrate:	0.546

ADMET: Excretion

Clearance (CL):	11.353
Half-life (T1/2):	0.689

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.84
Drug-inuced Liver Injury (DILI):	0.686
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.971
Carcinogencity:	0.331
Eye Corrosion:	0.222
Eye Irritation:	0.488
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC43577

Natural Product ID:	NPC43577
*Common Name:**	MJJVORBCNQQRMU-AVNBRKTCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MJJVORBCNQQRMU-AVNBRKTCSA-N
Standard InCHI:	InChI=1S/C18H27NO4/c1-6-11(3)17(20)22-14-8-13-9-16(15(10-14)19(13)5)23-18(21)12(4)7-2/h6-7,13-16H,8-10H2,1-5H3/p+1/b11-6+,12-7+/t13-,14-,15+,16-/m0/s1
SMILES:	C/C=C(C)/C(=O)O[C@H]1C[C@H]2C[C@@H]([C@@H](C1)[NH+]2C)OC(=O)/C(=C/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	21159049
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000492] Tropane alkaloids

*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
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.3923/pjbs.2013.1138.1144]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17262437]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18326559]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Essential oil	n.a.	n.a.	PMID[23163425]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23865201]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[24508058]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25650289]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	garlic skin	n.a.	n.a.	PMID[25726329]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350088]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Bulb	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16087	Atractylodes lancea	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 NPC43577 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	68
0.1-0.2	883
0.2-0.3	15937
0.3-0.4	17927
0.4-0.5	6965
0.5-0.6	858
0.6-0.7	54
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	3
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 NPC43577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	69
0.1-0.2	556
0.2-0.3	4337
0.3-0.4	3330
0.4-0.5	757
0.5-0.6	92
0.6-0.7	9
0.7-0.8	0
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