NPASS Compound

Structure

NPC226836 OpenBabel06302215132D 31 36 0 0 1 0 0 0 0 0999 V2000 -0.0000 -1.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5036 -0.8722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5107 -0.8722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0143 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5107 0.8722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1846 1.6207 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9752 2.6058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1047 1.2110 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1052 2.1716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9368 2.6512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7684 2.1707 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4315 2.1699 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2636 2.6495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0947 2.1690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0942 1.2085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9253 0.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9249 -0.2318 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0933 -0.7114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2622 -0.2311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2626 0.7289 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3963 0.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4310 1.2093 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5994 0.7297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5991 -0.2703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7679 1.2102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9358 0.7306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9354 -0.2694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7969 -0.7358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9994 0.2094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5036 0.8722 0.0000 N 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 2 1 1 6 0 0 0 2 3 1 0 0 0 0 2 31 1 0 0 0 0 4 3 1 6 0 0 0 4 5 1 0 0 0 0 4 29 1 0 0 0 0 5 6 1 0 0 0 0 5 30 1 1 0 0 0 6 7 1 1 0 0 0 6 8 1 0 0 0 0 8 26 1 0 0 0 0 8 9 1 1 0 0 0 8 29 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 25 1 0 0 0 0 12 13 1 6 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 20 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 28 1 1 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 6 0 0 0 20 22 1 0 0 0 0 22 23 1 1 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 25 26 2 0 0 0 0 26 27 1 0 0 0 0 30 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	425.29
Volume:	453.667
LogP:	4.398
LogD:	4.128
LogS:	-4.831
# Rotatable Bonds:	0
TPSA:	58.56
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	5.599
Fsp3:	0.815
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.029
MDCK Permeability:	1.0629880307533313e-05
Pgp-inhibitor:	0.438
Pgp-substrate:	0.862
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.073
30% Bioavailability (F30%):	0.529

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.188
Plasma Protein Binding (PPB):	75.42186737060547%
Volume Distribution (VD):	1.979
Pgp-substrate:	14.041666984558105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.461
CYP2C19-inhibitor:	0.383
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.808
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.562

ADMET: Excretion

Clearance (CL):	10.768
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.199
Human Hepatotoxicity (H-HT):	0.356
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.854
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.277
Carcinogencity:	0.831
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC226836

Natural Product ID:	NPC226836
*Common Name:**	CLEXYFLHGFJONT-QDWDECSQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CLEXYFLHGFJONT-QDWDECSQSA-N
Standard InCHI:	InChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19+,20-,21+,23+,24-,26+,27-/m0/s1
SMILES:	C[C@H]1C[C@@H]2[C@H]([C@@H](C)[C@@]3(CC[C@@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6(C)[C@H]5C(=O)C4=C3C)O)O2)NC1
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:0002724] Steroidal alkaloids [CHEMONTID:0002728] Jerveratrum-type 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
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	Roots	n.a.	n.a.	PMID[2089115]
NPO2634	Tetrapleura tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8289059]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10815	Uncaria borneensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10815	Uncaria borneensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4148	Artemisia spicigera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO612	Pteronia stricta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9242	Bauhinia manca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10815	Uncaria borneensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9373	Sigmadocia symbiotica	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12228	Rhizocarpon viridiatrum	Species	Rhizocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1718	Sarcodontia setosa	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7600	Gnetum macrostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2634	Tetrapleura tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20796	Stemonoporus canaliculatus	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7675	Perezia cuernavacana	Species	Pereziidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3787	Polycarpa clavata	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1968	Delphinium ternatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16865	Prunus serrulata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8057	Bulnesia retama	Species	Zygophyllaceae	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 NPC226836 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	104
0.1-0.2	678
0.2-0.3	3033
0.3-0.4	18273
0.4-0.5	11742
0.5-0.6	7807
0.6-0.7	1028
0.7-0.8	26
0.8-0.85	0
0.85-0.9	1
0.9-0.95	3
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 NPC226836 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	95
0.1-0.2	455
0.2-0.3	2223
0.3-0.4	4133
0.4-0.5	1687
0.5-0.6	486
0.6-0.7	71
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