NPASS Compound

Structure

NPC242755 OpenBabel06302216142D 25 28 0 0 0 0 0 0 0 0999 V2000 -1.6676 -4.9506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7936 -4.4463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -3.4372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6671 -2.9324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6669 -1.9233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8338 -1.4426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8335 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6664 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4994 -0.4804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4997 -1.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3737 -1.9465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6662 0.9628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8331 1.4435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8329 2.4435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6665 0.9621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5001 1.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3329 0.9618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3327 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4997 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6664 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8333 -0.4811 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 4.1987 -0.5008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0802 -4.9510 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 25 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 23 1 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 15 23 2 0 0 0 0 15 16 1 0 0 0 0 16 21 2 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	305.698
LogP:	2.9
LogD:	2.597
LogS:	-3.715
# Rotatable Bonds:	5
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.504
Synthetic Accessibility Score:	2.356
Fsp3:	0.059
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.75
MDCK Permeability:	1.2211770808789879e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.132

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	98.85089874267578%
Volume Distribution (VD):	0.447
Pgp-substrate:	0.7995885610580444%

ADMET: Metabolism

CYP1A2-inhibitor:	0.918
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.413
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.605
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.165
CYP2D6-substrate:	0.757
CYP3A4-inhibitor:	0.5
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	8.994
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.51
AMES Toxicity:	0.933
Rat Oral Acute Toxicity:	0.43
Maximum Recommended Daily Dose:	0.851
Skin Sensitization:	0.879
Carcinogencity:	0.777
Eye Corrosion:	0.025
Eye Irritation:	0.956
Respiratory Toxicity:	0.771

Download Data

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

Natural Product: NPC242755

Natural Product ID:	NPC242755
*Common Name:**	YABIJLLNNFURIJ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YABIJLLNNFURIJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3
SMILES:	CC(=CCc1cc2c(cc1O)oc(=O)c1c3ccc(cc3oc21)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	5281806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000354] Coumestans

*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
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18359631]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20663508]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24507928]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[25710081]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3069958]
NPO17794	Streptomyces violaceusniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8557611]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[8759164]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544566]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18560	Tripterospermum japonicum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4002	Lappula intermedia	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18560	Tripterospermum japonicum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4002	Lappula intermedia	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1470	Fructus psoraleae corylifoliae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14323	Bossiella orbigniana	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19260	Zanthoxylum petiolare	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12920	Erimacrus isenbeckii	Species	Atelecyclidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19809	Streptomyces roseoviolaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17794	Streptomyces violaceusniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4002	Lappula intermedia	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9811	Macrotyloma uniflorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18560	Tripterospermum japonicum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19587	Cordia rothii	Species	Cordiaceae	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

Activity Type	# Activity
IC50	1
Kd	1
Ki	1

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3896	Individual Protein	5-lipoxygenase activating protein	Homo sapiens	Kd	=	21000.0	nM	PMID[552949]
NPT2	Others	Unspecified		IC50	=	4200.0	nM	PMID[552950]
NPT2	Others	Unspecified		Ki	=	1700.0	nM	PMID[552950]

☑ 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 NPC242755 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	398
0.1-0.2	1821
0.2-0.3	4182
0.3-0.4	10386
0.4-0.5	8099
0.5-0.6	4268
0.6-0.7	5830
0.7-0.8	4550
0.8-0.85	2220
0.85-0.9	785
0.9-0.95	148
0.95-1	10

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 NPC242755 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	989
0.2-0.3	1560
0.3-0.4	2676
0.4-0.5	2004
0.5-0.6	1068
0.6-0.7	314
0.7-0.8	105
0.8-0.85	48
0.85-0.9	16
0.9-0.95	3
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