NPASS Compound

Structure

NPC45666 OpenBabel06302215422D 44 51 0 0 1 0 0 0 0 0999 V2000 2.1790 3.0731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1790 2.1203 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0042 1.6440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0042 0.6912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1790 0.2148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1790 -0.7380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3539 -1.2144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5288 -0.7380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5288 0.2148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3539 0.6912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3539 1.6440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2755 2.2093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0178 2.7185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6087 3.1164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0926 3.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4746 3.4228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2035 3.8929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9497 3.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0315 3.2980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5177 2.9991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8805 2.5586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0806 2.0241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0158 2.2067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2982 1.7562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5491 2.1523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7422 1.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1000 2.0912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0964 1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9260 0.9089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5880 0.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1190 0.1239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5698 -0.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6012 -0.6838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3573 0.0267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 0.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8203 1.0910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1904 1.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6825 1.3442 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8507 3.2423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4105 2.1476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0519 -1.0371 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 1.3539 -2.1672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1790 -2.6436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 11 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 10 2 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 7 43 1 0 0 0 0 8 41 1 0 0 0 0 8 9 2 0 0 0 0 9 42 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 6 0 0 0 12 13 1 0 0 0 0 13 18 2 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 19 20 1 0 0 0 0 20 25 2 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 24 2 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 29 28 1 6 0 0 0 29 30 1 0 0 0 0 29 38 1 0 0 0 0 30 35 2 0 0 0 0 30 31 1 0 0 0 0 31 32 2 0 0 0 0 32 33 1 0 0 0 0 32 42 1 0 0 0 0 33 34 2 0 0 0 0 33 41 1 0 0 0 0 34 35 1 0 0 0 0 35 36 1 0 0 0 0 36 37 1 0 0 0 0 37 38 1 0 0 0 0 38 39 2 0 0 0 0 38 40 1 0 0 0 0 43 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.26
Volume:	605.858
LogP:	5.892
LogD:	3.221
LogS:	-5.671
# Rotatable Bonds:	2
TPSA:	72.45
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	9
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.158
Synthetic Accessibility Score:	6.365
Fsp3:	0.333
Lipinski Rule-of-5:	Rejected
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:	-5.77
MDCK Permeability:	4.0238071960629895e-05
Pgp-inhibitor:	0.117
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.546
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	63.128700256347656%
Volume Distribution (VD):	0.844
Pgp-substrate:	27.206464767456055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.251
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.817
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.937
CYP3A4-inhibitor:	0.235
CYP3A4-substrate:	0.954

ADMET: Excretion

Clearance (CL):	10.61
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.865
Human Hepatotoxicity (H-HT):	0.008
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.203
Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.258
Carcinogencity:	0.604
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.461

Download Data

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

Natural Product: NPC45666

Natural Product ID:	NPC45666
*Common Name:**	YSJFSRXIDTYKBR-XZTSFBBGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YSJFSRXIDTYKBR-XZTSFBBGSA-N
Standard InCHI:	InChI=1S/C36H36N2O6/c1-37-13-11-24-19-33(41-4)35-36-34(24)27(37)15-21-5-8-25(9-6-21)42-30-17-22(7-10-29(30)40-3)16-28-26-20-32(44-36)31(43-35)18-23(26)12-14-38(28,2)39/h5-10,17-20,27-28H,11-16H2,1-4H3/t27-,28-,38+/m0/s1
SMILES:	CN1CCc2cc(c3c4c2[C@@H]1Cc1ccc(cc1)Oc1cc(ccc1OC)C[C@H]1c2cc(c(cc2CC[N@]1(=O)C)O3)O4)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5156	Hypoestes rosea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7389	Rhodiola atuntsuensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7389	Rhodiola atuntsuensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5156	Hypoestes rosea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6730	Crossopteryx febrifuga	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24372	Artemisia palustris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19931	Pyrus x nivalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1516	Passiflora suberosa	Species	Passifloraceae	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 NPC45666 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	453
0.1-0.2	2119
0.2-0.3	10730
0.3-0.4	7633
0.4-0.5	6783
0.5-0.6	10437
0.6-0.7	3756
0.7-0.8	579
0.8-0.85	82
0.85-0.9	39
0.9-0.95	70
0.95-1	16

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 NPC45666 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	851
0.2-0.3	1139
0.3-0.4	2346
0.4-0.5	2406
0.5-0.6	1539
0.6-0.7	523
0.7-0.8	96
0.8-0.85	3
0.85-0.9	2
0.9-0.95	2
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