NPASS Compound

Structure

NPC268799 OpenBabel06302215512D 37 39 0 0 1 0 0 0 0 0999 V2000 4.9641 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 0.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 -1.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 -1.9019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 -1.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -1.9019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -1.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -0.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 0.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 0.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 1.0981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5000 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.3660 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 2.5981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.2321 1.5981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0981 1.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 3.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 4.3301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 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 1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5622 -1.9019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5622 0.0981 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 37 1 0 0 0 0 4 5 2 0 0 0 0 4 36 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 3 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 11 12 1 0 0 0 0 12 17 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 20 21 2 0 0 0 0 20 22 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 26 27 2 3 0 0 0 27 28 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 35 1 0 0 0 0 32 33 1 0 0 0 0 32 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.13
Volume:	491.768
LogP:	1.426
LogD:	0.876
LogS:	-2.026
# Rotatable Bonds:	9
TPSA:	211.28
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.156
Synthetic Accessibility Score:	4.164
Fsp3:	0.24
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.212
MDCK Permeability:	9.620004675525706e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.582
Human Intestinal Absorption (HIA):	0.916
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	98.6004867553711%
Volume Distribution (VD):	0.275
Pgp-substrate:	1.9304776191711426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.401
CYP2C9-substrate:	0.653
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	4.548
Half-life (T1/2):	0.957

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.063
Skin Sensitization:	0.908
Carcinogencity:	0.13
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.021

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

Natural Product: NPC268799

Natural Product ID:	NPC268799
*Common Name:**	YDDUMTOHNYZQPO-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YDDUMTOHNYZQPO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)
SMILES:	c1cc(c(cc1C=CC(=O)OC1CC(CC(C1O)O)(C(=O)O)OC(=O)C=Cc1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	205954
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002512] Quinic acids and derivatives

*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

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[27169184]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[26110443]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26081757]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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☑ 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

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Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference
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☑ 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

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
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☑ 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 NPC268799 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	330
0.1-0.2	1314
0.2-0.3	3226
0.3-0.4	7444
0.4-0.5	10235
0.5-0.6	5757
0.6-0.7	8436
0.7-0.8	5560
0.8-0.85	270
0.85-0.9	56
0.9-0.95	27
0.95-1	42

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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 NPC268799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	785
0.2-0.3	1698
0.3-0.4	2766
0.4-0.5	2020
0.5-0.6	1058
0.6-0.7	457
0.7-0.8	80
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
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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