NPASS Compound

Structure

NPC51545 OpenBabel06302215342D 40 45 0 0 1 0 0 0 0 0999 V2000 1.6944 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -0.4891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8978 0.9569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5886 2.4109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3683 2.2075 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8909 3.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8478 3.5446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1501 4.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4955 5.2020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5386 4.9986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2363 4.0682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7205 3.8648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1159 5.7256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1070 4.6784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8707 1.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3598 1.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8707 2.7535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3598 3.6007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3381 3.6007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8272 2.7535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3381 1.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8272 4.4479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2686 0.1655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -0.4891 0.0000 C 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 -1.6944 -2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 3 40 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 7 6 1 6 0 0 0 7 8 1 0 0 0 0 7 37 1 0 0 0 0 8 9 1 0 0 0 0 8 39 1 1 0 0 0 9 10 1 0 0 0 0 10 36 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 11 38 1 0 0 0 0 12 13 1 0 0 0 0 13 35 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 14 36 1 0 0 0 0 15 16 1 0 0 0 0 15 27 2 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 18 23 2 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 24 1 0 0 0 0 27 28 1 0 0 0 0 27 35 1 0 0 0 0 28 33 2 0 0 0 0 28 29 1 0 0 0 0 29 30 2 0 0 0 0 30 31 1 0 0 0 0 31 32 2 0 0 0 0 31 34 1 0 0 0 0 32 33 1 0 0 0 0 36 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.12
Volume:	527.089
LogP:	4.861
LogD:	2.925
LogS:	-4.728
# Rotatable Bonds:	4
TPSA:	181.05
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.096
Synthetic Accessibility Score:	3.872
Fsp3:	0.1
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.102
MDCK Permeability:	5.7954134717874695e-06
Pgp-inhibitor:	0.029
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.085
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	98.65260314941406%
Volume Distribution (VD):	0.385
Pgp-substrate:	3.835415840148926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.627
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.191
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.63
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.101
CYP2D6-substrate:	0.242
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	12.077
Half-life (T1/2):	0.813

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.761
Rat Oral Acute Toxicity:	0.261
Maximum Recommended Daily Dose:	0.335
Skin Sensitization:	0.922
Carcinogencity:	0.257
Eye Corrosion:	0.003
Eye Irritation:	0.899
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC51545

Natural Product ID:	NPC51545
*Common Name:**	LYBUQSTWQONGEQ-RBISFHTESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LYBUQSTWQONGEQ-RBISFHTESA-N
Standard InCHI:	InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)28-22(36)11-18-20(34)12-23-24(30(18)40-28)25(29(39-23)14-3-7-16(32)8-4-14)27(38)19-9-17(33)10-21(35)26(19)37/h1-10,12,22,28,31-37H,11H2/t22-,28+/m0/s1
SMILES:	c1cc(ccc1[C@@H]1[C@H](Cc2c(cc3c(c(C(=O)c4cc(cc(c4O)O)O)c(c4ccc(cc4)O)o3)c2O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15635251]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22494026]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24156713]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[24660446]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32997496]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[501363]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320737]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18816	Lindera glauca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16416	Serratula strangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18816	Lindera glauca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18393	Eugenia sandwicensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16416	Serratula strangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19406	Chrysanthemum leptophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18247	Globicephala melas	Species	Delphinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13505	Grateloupia livida	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19479	Trametes feei	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15287	Vernonia megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14015	Salacia cordata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10882	Acer caudatifolium	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10705	Marshallia graminifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12376	Baccharis macraei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17558	Cynoglossum formosanum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7037	Rumohra adiantiformis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18393	Eugenia sandwicensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18816	Lindera glauca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17135	Mikania goyazensis	Species	Asteraceae	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 NPC51545 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	486
0.1-0.2	1888
0.2-0.3	4260
0.3-0.4	10605
0.4-0.5	7691
0.5-0.6	3850
0.6-0.7	5339
0.7-0.8	4900
0.8-0.85	2206
0.85-0.9	1375
0.9-0.95	93
0.95-1	4

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 NPC51545 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	433
0.1-0.2	970
0.2-0.3	1916
0.3-0.4	2709
0.4-0.5	1746
0.5-0.6	916
0.6-0.7	292
0.7-0.8	121
0.8-0.85	28
0.85-0.9	19
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