NPASS Compound

Structure

NPC150767 OpenBabel07101718292D 41 45 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 3 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 10 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 5 15 2 0 0 0 0 6 14 1 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 7 18 1 0 0 0 0 8 28 1 0 0 0 0 9 1 1 1 0 0 0 9 22 1 0 0 0 0 9 38 1 0 0 0 0 10 15 1 0 0 0 0 11 12 2 0 0 0 0 11 29 1 0 0 0 0 12 30 1 0 0 0 0 13 20 1 0 0 0 0 13 31 2 0 0 0 0 14 22 1 0 0 0 0 14 32 1 6 0 0 0 15 39 1 0 0 0 0 16 21 1 1 0 0 0 16 38 1 0 0 0 0 17 20 1 0 0 0 0 17 39 1 0 0 0 0 18 21 2 0 0 0 0 18 40 1 0 0 0 0 19 8 1 6 0 0 0 19 23 1 0 0 0 0 19 41 1 0 0 0 0 20 24 2 0 0 0 0 21 24 1 0 0 0 0 22 33 1 1 0 0 0 23 25 1 0 0 0 0 23 34 1 1 0 0 0 24 35 1 0 0 0 0 25 26 1 0 0 0 0 25 36 1 6 0 0 0 26 27 1 0 0 0 0 26 37 1 1 0 0 0 27 40 1 6 0 0 0 27 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.16
Volume:	534.737
LogP:	0.491
LogD:	-0.128
LogS:	-3.558
# Rotatable Bonds:	5
TPSA:	239.97
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	4.826
Fsp3:	0.444
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:	-6.401
MDCK Permeability:	1.8390079276286997e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.867
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	86.92453002929688%
Volume Distribution (VD):	0.671
Pgp-substrate:	15.040504455566406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.211
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.705
Half-life (T1/2):	0.621

ADMET: Toxicity

hERG Blockers:	0.134
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.792
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.778
Skin Sensitization:	0.837
Carcinogencity:	0.133
Eye Corrosion:	0.003
Eye Irritation:	0.062
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC150767

Natural Product ID:	NPC150767
*Common Name:**	Farobin A
IUPAC Name:	6-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	UKNXXFWLEJRJCY-NCJQNZQYSA-N
Standard InCHI:	InChI=1S/C27H30O14/c1-9-22(33)14(32)6-16(38-9)21-18(40-27-26(37)25(36)23(34)19(8-28)41-27)7-17-20(24(21)35)13(31)5-15(39-17)10-2-3-11(29)12(30)4-10/h2-5,7,9,14,16,19,22-23,25-30,32-37H,6,8H2,1H3/t9-,14+,16-,19-,22+,23-,25+,26-,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc3oc(cc(=O)c3c(c2[C@H]2C[C@H](O)[C@H]([C@H](O2)C)O)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224895
PubChem CID:	46938449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*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
NPO33290	fargesia robusta	Species	Poaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20863141]

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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
No data available in table

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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

Activity Type	# Activity
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		Activity	=	26.8	n.a.	PMID[509866]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.332	n.a.	PMID[509866]

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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 NPC150767 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	444
0.1-0.2	1824
0.2-0.3	3992
0.3-0.4	9579
0.4-0.5	8636
0.5-0.6	4531
0.6-0.7	5399
0.7-0.8	5287
0.8-0.85	1868
0.85-0.9	659
0.9-0.95	406
0.95-1	72

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Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC78734
0.9938	High Similarity	NPC256760
0.9876	High Similarity	NPC208668
0.9875	High Similarity	NPC218488
0.9815	High Similarity	NPC294629

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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 NPC150767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	945
0.2-0.3	1908
0.3-0.4	2743
0.4-0.5	1841
0.5-0.6	881
0.6-0.7	271
0.7-0.8	123
0.8-0.85	24
0.85-0.9	6
0.9-0.95	3
0.95-1	4

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9689	High Similarity	NPD7054	Approved
0.963	High Similarity	NPD7074	Phase 3
0.963	High Similarity	NPD7472	Approved
0.9571	High Similarity	NPD6797	Phase 2
0.9512	High Similarity	NPD7251	Discontinued

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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