NPASS Compound

Structure

NPC298541 OpenBabel06302216002D 40 44 0 0 1 0 0 0 0 0999 V2000 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 6.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5622 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -3.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5622 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4282 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2942 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4282 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2942 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1603 1.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1603 1.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.0263 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6603 1.0000 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 2 1 1 1 0 0 0 2 3 1 0 0 0 0 2 40 1 0 0 0 0 3 4 1 6 0 0 0 3 40 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 8 9 1 0 0 0 0 9 29 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 12 1 0 0 0 0 12 13 2 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 18 19 2 0 0 0 0 18 20 1 0 0 0 0 20 21 2 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 27 2 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 24 25 1 0 0 0 0 25 26 2 0 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 29 30 2 0 0 0 0 31 32 1 0 0 0 0 32 33 2 0 0 0 0 32 34 1 0 0 0 0 34 35 2 0 0 0 0 36 35 1 6 0 0 0 36 37 1 0 0 0 0 36 39 1 0 0 0 0 37 38 1 1 0 0 0 37 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.14
Volume:	535.646
LogP:	3.465
LogD:	2.821
LogS:	-4.735
# Rotatable Bonds:	10
TPSA:	152.26
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.219
Synthetic Accessibility Score:	4.423
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.7
MDCK Permeability:	2.8325403036433272e-05
Pgp-inhibitor:	0.105
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	97.17179870605469%
Volume Distribution (VD):	0.313
Pgp-substrate:	0.8708035349845886%

ADMET: Metabolism

CYP1A2-inhibitor:	0.928
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.926
CYP2C9-substrate:	0.647
CYP2D6-inhibitor:	0.898
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.861
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	5.449
Half-life (T1/2):	0.729

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.728
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.645
Rat Oral Acute Toxicity:	0.624
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.919
Carcinogencity:	0.786
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.736

Download Data

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

Natural Product: NPC298541

Natural Product ID:	NPC298541
*Common Name:**	BJWGCWHLADXFNM-RRDZNQRYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BJWGCWHLADXFNM-RRDZNQRYSA-N
Standard InCHI:	InChI=1S/C30H24O10/c1-15-21(37-15)11-13-23(33)39-29-25(17-3-7-19(31)8-4-17)28(36)30(40-24(34)14-12-22-16(2)38-22)26(27(29)35)18-5-9-20(32)10-6-18/h3-16,21-22,31-32H,1-2H3/b13-11-,14-12-/t15-,16-,21-,22-/m0/s1
SMILES:	C[C@H]1[C@H](/C=CC(=O)OC2=C(c3ccc(cc3)O)C(=O)C(=C(c3ccc(cc3)O)C2=O)OC(=O)/C=C[C@H]2[C@H](C)O2)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002494] P-benzoquinones

*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
NPO29532	Vigna angularis	Species	Fabaceae	Eukaryota	Leaf Diffusate	n.a.	n.a.	Database[FooDB]
NPO29532	Vigna angularis	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29532	Vigna angularis	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29532	Vigna angularis	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29532	Vigna angularis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29532	Vigna angularis	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO29532	Vigna angularis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22014	Dysphania botrys	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29532	Vigna angularis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29173	Leucadendron adscendens	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28951	Manglietia phuthoensis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29489	Garcinia opaca	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22014	Dysphania botrys	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28972	Comatula solaris	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29451	Clostridium tertium	Species	Clostridiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29029	Ophistreptus levis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29205	Vepris fitoravina	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28846	Doris nobilis	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18062	Tapinella atrotomentosa	Species	Tapinellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29532	Vigna angularis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18494	Carassea connexa	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28886	Acacia latifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24755	Abies nordmanniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28866	Haematomma ochrophaeum	Species	Haematommataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28900	Planobispora rosea	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29128	Pimpinella heyneana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29416	Rhodophyllus nidorosus	Species	Entolomataceae	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 NPC298541 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	281
0.1-0.2	1350
0.2-0.3	3397
0.3-0.4	8671
0.4-0.5	10721
0.5-0.6	7029
0.6-0.7	10563
0.7-0.8	676
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
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 NPC298541 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	877
0.2-0.3	1432
0.3-0.4	2614
0.4-0.5	2246
0.5-0.6	1299
0.6-0.7	415
0.7-0.8	20
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