NPASS Compound

Structure

NPC220400 OpenBabel06302215142D 30 32 0 0 1 0 0 0 0 0999 V2000 -0.6925 -3.4648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7971 -2.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6631 -1.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4552 -0.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4606 -0.8876 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0539 -1.8011 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9139 -2.0527 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7141 -1.4529 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5318 -2.0285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4781 -1.7053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2370 -2.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8368 -3.7842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2371 -2.9990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7440 -0.4533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9811 0.1933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1194 0.9928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 0.3930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6575 -0.0466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7621 0.9479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9530 1.5357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6756 1.3547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7801 2.3492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9711 2.9370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0756 3.9315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4846 0.7669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3982 1.1736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5027 2.1681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6937 2.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4162 2.5749 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 5 4 1 1 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 2 1 1 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 6 0 0 0 8 9 1 1 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 1 0 0 0 15 16 1 0 0 0 0 16 17 1 1 0 0 0 16 18 1 0 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 28 29 2 0 0 0 0 28 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	417.902
LogP:	0.284
LogD:	0.934
LogS:	-2.28
# Rotatable Bonds:	8
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.226
Synthetic Accessibility Score:	4.979
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.875
MDCK Permeability:	0.0001226505555678159
Pgp-inhibitor:	0.722
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.645
20% Bioavailability (F20%):	0.844
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	49.76054763793945%
Volume Distribution (VD):	1.153
Pgp-substrate:	41.59969711303711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.121
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.511
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	3.778
Half-life (T1/2):	0.878

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.86
Drug-inuced Liver Injury (DILI):	0.597
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.122
Maximum Recommended Daily Dose:	0.112
Skin Sensitization:	0.937
Carcinogencity:	0.105
Eye Corrosion:	0.038
Eye Irritation:	0.118
Respiratory Toxicity:	0.491

Download Data

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

Natural Product: NPC220400

Natural Product ID:	NPC220400
*Common Name:**	ASIOTCDZQTZAME-JPUTZVMCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ASIOTCDZQTZAME-JPUTZVMCSA-N
Standard InCHI:	InChI=1S/C22H28O8/c1-11-5-6-15-17(11)19-18(12(2)20(25)30-19)16(9-22(15,4)27)29-21(26)14(7-8-23)10-28-13(3)24/h5,7,15-19,23,27H,2,6,8-10H2,1,3-4H3/b14-7+/t15-,16-,17+,18-,19-,22-/m1/s1
SMILES:	CC1=CC[C@@H]2[C@H]1[C@@H]1[C@H](C(=C)C(=O)O1)[C@@H](C[C@@]2(C)O)OC(=O)/C(=C/CO)/COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395508]
NPO4796	Polyscias fulva	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170676]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730261]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15973055]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18053715]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18656987]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21053938]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23387901]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	Moroccan	n.a.	PMID[23713692]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7766039]
NPO7280	Lycoris squamigera	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7280	Lycoris squamigera	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7280	Lycoris squamigera	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5438	Ficus racemosa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7591	Cedrus deodara	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4796	Polyscias fulva	Species	Araliaceae	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 NPC220400 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	224
0.1-0.2	1261
0.2-0.3	4692
0.3-0.4	8850
0.4-0.5	14478
0.5-0.6	7527
0.6-0.7	4151
0.7-0.8	1281
0.8-0.85	174
0.85-0.9	41
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 NPC220400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1853
0.2-0.3	3686
0.3-0.4	2245
0.4-0.5	740
0.5-0.6	335
0.6-0.7	64
0.7-0.8	16
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
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