NPASS Compound

Structure

NPC27186 OpenBabel06302216152D 64 70 0 0 1 0 0 0 0 0999 V2000 -6.6435 3.8356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8130 4.3151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9826 3.8356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1522 4.3151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3217 3.8356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3217 2.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1522 2.3973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9826 2.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8130 2.3973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4913 4.3151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6609 3.8356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6609 2.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4913 2.3973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8304 2.3973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8304 1.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9589 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8304 1.4384 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6609 0.9589 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6609 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8304 -0.4795 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8304 -1.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6609 -1.9178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6609 -2.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4913 -3.3562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4913 -4.3151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3217 -2.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3217 -1.9178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1522 -1.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1522 -0.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9826 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8130 -0.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8130 -1.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9826 -1.9178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6435 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4913 -1.4384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8304 -3.3562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3217 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1522 -0.4795 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0282 -0.0894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6698 -0.8020 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5458 -1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3216 -0.6284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1904 -1.6325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2524 -1.4331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4456 -0.2384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2275 0.8485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8304 -3.3562 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8304 -4.3151 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6609 -4.7945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4913 -4.3151 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4913 -3.3562 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3217 -2.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1522 -3.3562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6609 -2.8767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3217 -4.7945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6609 -5.7534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.7945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8304 -4.3151 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 2.4913 -0.4795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4913 1.4384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8304 2.3973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 8 2 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 14 15 1 0 0 0 0 16 15 1 6 0 0 0 16 17 1 0 0 0 0 16 61 1 0 0 0 0 17 18 1 0 0 0 0 17 64 1 1 0 0 0 18 19 1 0 0 0 0 18 63 1 6 0 0 0 19 20 1 0 0 0 0 19 62 1 1 0 0 0 20 21 1 6 0 0 0 20 61 1 0 0 0 0 21 38 2 0 0 0 0 21 22 1 0 0 0 0 22 35 1 0 0 0 0 22 23 2 0 0 0 0 23 24 1 0 0 0 0 23 36 1 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 26 27 2 0 0 0 0 27 28 1 0 0 0 0 27 35 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 34 1 0 0 0 0 32 33 1 0 0 0 0 36 37 2 0 0 0 0 36 60 1 0 0 0 0 37 38 1 0 0 0 0 38 39 1 0 0 0 0 40 39 1 6 0 0 0 40 41 1 0 0 0 0 40 46 1 0 0 0 0 41 42 1 0 0 0 0 41 48 1 1 0 0 0 42 43 1 0 0 0 0 42 45 1 0 0 0 0 42 47 1 1 0 0 0 43 44 1 0 0 0 0 45 46 1 0 0 0 0 49 37 1 1 0 0 0 49 50 1 0 0 0 0 49 56 1 0 0 0 0 50 51 1 0 0 0 0 50 59 1 6 0 0 0 51 52 1 0 0 0 0 51 58 1 1 0 0 0 52 53 1 0 0 0 0 52 57 1 6 0 0 0 53 54 1 1 0 0 0 53 56 1 0 0 0 0 54 55 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	902.25
Volume:	834.204
LogP:	0.64
LogD:	-0.271
LogS:	-3.473
# Rotatable Bonds:	13
TPSA:	365.65
# H-Bond Aceptor:	22
# H-Bond Donor:	13
# Rings:	7
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.053
Synthetic Accessibility Score:	5.797
Fsp3:	0.429
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.597
MDCK Permeability:	1.495347805757774e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.985
20% Bioavailability (F20%):	0.824
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	77.97185516357422%
Volume Distribution (VD):	0.628
Pgp-substrate:	15.479700088500977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.123
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	1.108
Half-life (T1/2):	0.509

ADMET: Toxicity

hERG Blockers:	0.2
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.72
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.643
Carcinogencity:	0.061
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.004

Download Data

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

Natural Product: NPC27186

Natural Product ID:	NPC27186
*Common Name:**	VWDHYOBWFQBNEZ-AALLZNIUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VWDHYOBWFQBNEZ-AALLZNIUSA-N
Standard InCHI:	InChI=1S/C42H46O22/c1-58-22-10-16(2-8-19(22)46)3-9-25(48)59-13-24-30(50)33(53)35(55)39(63-24)28-36-26(20(47)11-21(61-36)17-4-6-18(45)7-5-17)31(51)27(38-34(54)32(52)29(49)23(12-43)62-38)37(28)64-41-40(56)42(57,14-44)15-60-41/h2-11,23-24,29-30,32-35,38-41,43-46,49-57H,12-15H2,1H3/b9-3+/t23-,24-,29-,30-,32+,33+,34-,35-,38+,39+,40+,41+,42-/m1/s1
SMILES:	COc1cc(ccc1O)/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](c2c3c(c(=O)cc(c4ccc(cc4)O)o3)c(c(c2O[C@H]2[C@@H]([C@@](CO)(CO2)O)O)[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-glycosides [CHEMONTID:0003535] Flavonoid 8-C-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

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24195	Stylissa carteri	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043426]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21574561]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23747095]
NPO3866	Pistia stratiotes	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24258601]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29192771]
NPO24195	Stylissa carteri	Species	Axinellidae	Eukaryota	n.a.	indopacific	n.a.	PMID[9917317]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Shoot Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16529	Plagiodera versicolora	Species	Chrysomelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3866	Pistia stratiotes	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21102	Thalictrum wangii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24195	Stylissa carteri	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12511	Leplaea thompsonii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21982	Erechtites hieraciifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2502	Lupinus mexicanus	Species	Fabaceae	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 NPC27186 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	447
0.1-0.2	1815
0.2-0.3	3729
0.3-0.4	8787
0.4-0.5	9457
0.5-0.6	5437
0.6-0.7	5914
0.7-0.8	5566
0.8-0.85	822
0.85-0.9	572
0.9-0.95	146
0.95-1	5

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 NPC27186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	939
0.2-0.3	2000
0.3-0.4	2786
0.4-0.5	1923
0.5-0.6	771
0.6-0.7	240
0.7-0.8	102
0.8-0.85	9
0.85-0.9	3
0.9-0.95	5
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