NPASS Compound

Structure

NPC79522 OpenBabel06302215282D 31 34 0 0 1 0 0 0 0 0999 V2000 3.3761 -1.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5319 -1.4629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5319 -0.4880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -1.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -2.9251 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8433 -1.4628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0009 -1.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8452 -1.4628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6895 -1.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8452 -0.4879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6891 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6891 0.9753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.9753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 2.4391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6904 2.9270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3801 2.9269 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3801 3.9269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2247 2.4390 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2246 1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 0.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 1.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5355 0.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6903 0.9752 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6903 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 -0.4879 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0908 2.9389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 1 0 0 0 10 8 1 1 0 0 0 10 11 1 0 0 0 0 10 29 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 29 1 0 0 0 0 13 14 1 6 0 0 0 13 15 1 0 0 0 0 15 26 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 18 17 1 1 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 6 0 0 0 19 21 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 1 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 1 0 0 0 24 26 1 0 0 0 0 26 27 1 6 0 0 0 27 28 1 0 0 0 0 28 29 1 0 0 0 0 29 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.37
Volume:	488.222
LogP:	6.552
LogD:	5.51
LogS:	-6.085
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	4.667
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:	-4.697
MDCK Permeability:	1.0852602827071678e-05
Pgp-inhibitor:	0.936
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246
Plasma Protein Binding (PPB):	95.3478012084961%
Volume Distribution (VD):	1.367
Pgp-substrate:	1.3635377883911133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.539
CYP2C19-inhibitor:	0.112
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.269
CYP2C9-substrate:	0.198
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.798
CYP3A4-inhibitor:	0.814
CYP3A4-substrate:	0.783

ADMET: Excretion

Clearance (CL):	7.35
Half-life (T1/2):	0.108

ADMET: Toxicity

hERG Blockers:	0.738
Human Hepatotoxicity (H-HT):	0.303
Drug-inuced Liver Injury (DILI):	0.443
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.467
Maximum Recommended Daily Dose:	0.084
Skin Sensitization:	0.506
Carcinogencity:	0.368
Eye Corrosion:	0.271
Eye Irritation:	0.084
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC79522

Natural Product ID:	NPC79522
*Common Name:**	KXHHHBICYOMCON-HELIWFEESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KXHHHBICYOMCON-HELIWFEESA-N
Standard InCHI:	InChI=1S/C29H48O2/c1-18(2)25(30)11-8-19(3)21-12-16-29(7)24-10-9-22-20(4)26(31)14-15-27(22,5)23(24)13-17-28(21,29)6/h10,18-23,26,31H,8-9,11-17H2,1-7H3/t19-,20+,21-,22+,23-,26+,27+,28-,29+/m1/s1
SMILES:	CC(C)C(=O)CC[C@@H](C)[C@H]1CC[C@@]2(C)C3=CC[C@H]4[C@H](C)[C@H](CC[C@]4(C)[C@@H]3CC[C@]12C)O
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:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000260] Monohydroxy bile acids, alcohols 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
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4095	Hedysarum multijugum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6988	Diploschistes cretaceus	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6815	Streptomyces sclerotialus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4095	Hedysarum multijugum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8037	Bryum rutilans	Species	Bryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6429	Phlomis regelii	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 NPC79522 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	158
0.1-0.2	1110
0.2-0.3	5073
0.3-0.4	15335
0.4-0.5	7560
0.5-0.6	5566
0.6-0.7	4598
0.7-0.8	2603
0.8-0.85	469
0.85-0.9	154
0.9-0.95	63
0.95-1	8

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 NPC79522 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1419
0.2-0.3	4111
0.3-0.4	2408
0.4-0.5	583
0.5-0.6	166
0.6-0.7	100
0.7-0.8	150
0.8-0.85	45
0.85-0.9	16
0.9-0.95	5
0.95-1	4

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