NPASS Compound

Structure

NPC113472 OpenBabel06302215342D 30 31 0 0 1 0 0 0 0 0999 V2000 4.6831 3.0411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1831 3.9071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1831 3.9071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.0411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1831 2.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 6.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 7.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 2.0339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 O 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 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6831 4.7731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 2 30 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 12 1 0 0 0 0 6 7 1 6 0 0 0 6 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 9 29 1 6 0 0 0 10 28 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 6 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 18 19 2 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 22 23 1 1 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 27 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.26
Volume:	451.976
LogP:	3.229
LogD:	3.093
LogS:	-3.403
# Rotatable Bonds:	9
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	5.017
Fsp3:	0.6
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:	-4.73
MDCK Permeability:	1.8283795725437813e-05
Pgp-inhibitor:	0.939
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.476
30% Bioavailability (F30%):	0.26

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.898
Plasma Protein Binding (PPB):	76.71443939208984%
Volume Distribution (VD):	0.647
Pgp-substrate:	18.65610122680664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.229
CYP2C19-inhibitor:	0.672
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.804
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.257
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.843
CYP3A4-substrate:	0.433

ADMET: Excretion

Clearance (CL):	11.454
Half-life (T1/2):	0.337

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.254
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.814
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.859
Carcinogencity:	0.365
Eye Corrosion:	0.911
Eye Irritation:	0.33
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC113472

Natural Product ID:	NPC113472
*Common Name:**	DOUGJCUAIIVOOP-XFTRUYOKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DOUGJCUAIIVOOP-XFTRUYOKSA-N
Standard InCHI:	InChI=1S/C25H36O5/c1-16(2)8-7-10-25(6)14-21(27)19-15-30-22(13-18(5)26)24(19)20(25)9-11-29-23(28)12-17(3)4/h8-9,11-12,20-22,27H,7,10,13-15H2,1-6H3/b11-9+/t20-,21-,22-,25-/m0/s1
SMILES:	CC(=CCC[C@@]1(C)C[C@@H](C2=C([C@@H]1/C=C/OC(=O)C=C(C)C)[C@H](CC(=O)C)OC2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10645581
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003408] Isobenzofurans

*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
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)83457-3]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075772]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843567]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043405]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16155971]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125219]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665952]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345641]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19824618]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21667999]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27592135]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[324959]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33325237]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO276	Miscanthus sacchariflorus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15610	Citrus trifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24370	Crassocephalum crepidioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10806	Achillea roseoalba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3830	Euplotes rariseta	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5319	Ulmus thomasii	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6310	Ruta bracteosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4516	Fasciospongia rimosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7766	Pericopsis schliebenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1355	Urechis caupo	Species	Urechidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8103	Lecanora melanophthalma	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9903	Engelhardia spicata	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2304	Byssovorax cruenta	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25481	Lonchocarpus oaxacensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7060	Ficus ruficaulis	Species	Moraceae	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 NPC113472 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	194
0.1-0.2	1031
0.2-0.3	4039
0.3-0.4	8224
0.4-0.5	14980
0.5-0.6	7531
0.6-0.7	5188
0.7-0.8	1429
0.8-0.85	70
0.85-0.9	9
0.9-0.95	1
0.95-1	1

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 NPC113472 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1506
0.2-0.3	3495
0.3-0.4	2536
0.4-0.5	941
0.5-0.6	336
0.6-0.7	143
0.7-0.8	21
0.8-0.85	2
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