NPASS Compound

Structure

NPC173899 OpenBabel06302215312D 33 35 0 0 1 0 0 0 0 0999 V2000 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 9 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 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 11 1 0 0 0 0 13 12 1 6 0 0 0 13 14 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 33 1 1 0 0 0 15 16 1 0 0 0 0 15 32 1 6 0 0 0 16 17 1 0 0 0 0 16 31 1 1 0 0 0 17 18 1 6 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 20 19 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 6 0 0 0 22 23 1 0 0 0 0 22 28 1 6 0 0 0 23 24 1 0 0 0 0 23 27 1 1 0 0 0 24 25 1 6 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.19
Volume:	449.545
LogP:	0.448
LogD:	-0.318
LogS:	-2.372
# Rotatable Bonds:	8
TPSA:	167.53
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	4.377
Fsp3:	0.636
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.067
MDCK Permeability:	6.233816384337842e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.895
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	61.12445831298828%
Volume Distribution (VD):	0.553
Pgp-substrate:	23.01478385925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.619
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.135
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	1.305
Half-life (T1/2):	0.723

ADMET: Toxicity

hERG Blockers:	0.185
Human Hepatotoxicity (H-HT):	0.054
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.302
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.824
Carcinogencity:	0.141
Eye Corrosion:	0.004
Eye Irritation:	0.045
Respiratory Toxicity:	0.338

Download Data

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

Natural Product: NPC173899

Natural Product ID:	NPC173899
*Common Name:**	KNUPPNGCEAQRSV-XCPHWCDESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KNUPPNGCEAQRSV-XCPHWCDESA-N
Standard InCHI:	InChI=1S/C22H32O11/c1-4-5-11-6-7-12(13(8-11)29-3)32-22-20(28)18(26)16(24)14(33-22)9-30-21-19(27)17(25)15(23)10(2)31-21/h4,6-8,10,14-28H,1,5,9H2,2-3H3/t10-,14+,15-,16+,17+,18-,19+,20+,21+,22+/m0/s1
SMILES:	C=CCc1ccc(c(c1)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	15101911
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[10395493]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	Galls	n.a.	n.a.	PMID[16724837]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	n.a.	gall	n.a.	PMID[17827775]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18854	Jamesonia scammaniae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5621	Arisaema erubescens	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4690	Aphloia theiformis	Species	Aphloiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6496	Strongylosoma tambanum	Species	Paradoxosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18854	Jamesonia scammaniae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2814	Peperomia amplexicaulis	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1081	Parochetus communis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5621	Arisaema erubescens	Species	Araceae	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 NPC173899 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	371
0.1-0.2	1445
0.2-0.3	3732
0.3-0.4	9492
0.4-0.5	9006
0.5-0.6	5879
0.6-0.7	8204
0.7-0.8	3730
0.8-0.85	571
0.85-0.9	214
0.9-0.95	46
0.95-1	7

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 NPC173899 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	825
0.2-0.3	1820
0.3-0.4	2795
0.4-0.5	1768
0.5-0.6	956
0.6-0.7	572
0.7-0.8	104
0.8-0.85	5
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