NPASS Compound

Structure

NPC270992 OpenBabel06302215222D 32 35 0 0 1 0 0 0 0 0999 V2000 3.3854 -5.8541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -5.3665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5401 -4.3908 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3849 -3.9027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3846 -2.9270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 -2.4389 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0746 -2.9265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2292 -1.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0737 -0.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0734 0.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3829 0.0010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5369 0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6911 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6914 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5374 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3832 -0.9751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3834 -1.9751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -0.5114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6906 1.9539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5366 1.4658 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4025 1.9660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 1.4648 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7119 1.9644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6949 -3.9032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6947 -2.9275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8501 -4.3913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 3 2 1 1 0 0 0 3 4 1 0 0 0 0 3 30 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 11 10 1 6 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 6 0 0 0 18 27 1 0 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 20 21 2 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 1 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 26 27 1 0 0 0 0 27 28 2 0 0 0 0 30 31 1 0 0 0 0 30 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.36
Volume:	497.012
LogP:	5.989
LogD:	5.683
LogS:	-5.413
# Rotatable Bonds:	6
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.481
Synthetic Accessibility Score:	4.875
Fsp3:	0.897
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.749
MDCK Permeability:	1.4225439372239634e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.918
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.424

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.548
Plasma Protein Binding (PPB):	95.53197479248047%
Volume Distribution (VD):	1.197
Pgp-substrate:	1.2421871423721313%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.384
CYP2C19-inhibitor:	0.261
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.499
CYP2C9-substrate:	0.208
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.876
CYP3A4-substrate:	0.84

ADMET: Excretion

Clearance (CL):	10.5
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.19
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.341
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.667
Skin Sensitization:	0.457
Carcinogencity:	0.127
Eye Corrosion:	0.007
Eye Irritation:	0.074
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC270992

Natural Product ID:	NPC270992
*Common Name:**	RUXQTPOFIWOKQP-SFBYTARZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RUXQTPOFIWOKQP-SFBYTARZSA-N
Standard InCHI:	InChI=1S/C29H48O3/c1-7-19(17(2)3)9-8-18(4)22-10-11-23-27-24(12-13-28(22,23)5)29(6)20(15-25(27)31)14-21(30)16-26(29)32/h15,17-19,21-25,27,30-31H,7-14,16H2,1-6H3/t18-,19-,21-,22-,23+,24+,25-,27+,28-,29+/m1/s1
SMILES:	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(C)C(=C[C@H]3O)C[C@H](CC1=O)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	101712318
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
NPO16838	Salvia glutinosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16838	Salvia glutinosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28189	Metzgeria pubescens	Species	Metzgeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14253	Bothriocline longipes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11003	Euphorbia sancta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO191	Amaranthus hybr	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11814	Asphodeline tenuior	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11985	Glycyrrhiza triphylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11487	Senecio madagascariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13164	Iris hoogiana	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16838	Salvia glutinosa	Species	Lamiaceae	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 NPC270992 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	164
0.1-0.2	1089
0.2-0.3	4476
0.3-0.4	11868
0.4-0.5	10895
0.5-0.6	6596
0.6-0.7	4960
0.7-0.8	2245
0.8-0.85	312
0.85-0.9	81
0.9-0.95	11
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 NPC270992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1404
0.2-0.3	3913
0.3-0.4	2487
0.4-0.5	696
0.5-0.6	179
0.6-0.7	146
0.7-0.8	149
0.8-0.85	23
0.85-0.9	2
0.9-0.95	2
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