NPASS Compound

Structure

NPC268087 OpenBabel06302215262D 46 52 0 0 1 0 0 0 0 0999 V2000 1.6498 -3.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7838 -3.0933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0823 -3.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9483 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9483 -2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8143 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8143 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9483 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0823 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0823 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7838 -2.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3387 -2.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9368 -2.3517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0468 -3.3456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9352 -3.3862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4145 -2.6371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0054 -1.8474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5132 -2.1887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3601 -1.3648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5390 -0.7931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5225 -0.1943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3124 0.3666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9316 0.8290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7858 0.6864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0895 -0.1246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4213 1.1427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7977 2.0692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8369 1.2736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2415 1.2078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6998 0.9521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2705 0.5344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6588 0.1798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1781 0.2623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4375 0.7198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7573 0.4892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1168 0.6508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1566 1.0431 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3715 -0.7781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0575 -1.5057 0.0000 C 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 4.4135 -2.6826 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8735 -3.5706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9483 0.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0823 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6803 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6803 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 11 1 0 0 0 0 2 3 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 8 1 0 0 0 0 7 45 1 0 0 0 0 8 9 2 0 0 0 0 8 43 1 0 0 0 0 9 40 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 1 0 0 0 12 13 1 0 0 0 0 13 18 2 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 41 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 20 1 0 0 0 0 20 25 2 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 23 26 1 0 0 0 0 24 25 1 0 0 0 0 26 27 2 0 0 0 0 26 28 1 0 0 0 0 28 37 2 0 0 0 0 28 29 1 0 0 0 0 29 34 2 0 0 0 0 29 30 1 0 0 0 0 30 31 2 0 0 0 0 31 32 1 0 0 0 0 31 40 1 0 0 0 0 32 33 2 0 0 0 0 32 38 1 0 0 0 0 33 34 1 0 0 0 0 34 35 1 0 0 0 0 35 36 2 0 0 0 0 36 37 1 0 0 0 0 38 39 1 0 0 0 0 41 42 1 0 0 0 0 43 44 1 0 0 0 0 45 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.24
Volume:	632.591
LogP:	6.322
LogD:	3.951
LogS:	-7.527
# Rotatable Bonds:	4
TPSA:	88.58
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	5.425
Fsp3:	0.243
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.686
MDCK Permeability:	3.433299934840761e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.866
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.417

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	90.43452453613281%
Volume Distribution (VD):	0.479
Pgp-substrate:	2.5482394695281982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.515
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.492
CYP2C9-substrate:	0.86
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.405
CYP3A4-substrate:	0.941

ADMET: Excretion

Clearance (CL):	7.737
Half-life (T1/2):	0.157

ADMET: Toxicity

hERG Blockers:	0.865
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.904
AMES Toxicity:	0.516
Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.152
Carcinogencity:	0.265
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.609

Download Data

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

Natural Product: NPC268087

Natural Product ID:	NPC268087
*Common Name:**	INUHRHLZFLIFNB-HHHXNRCGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	INUHRHLZFLIFNB-HHHXNRCGSA-N
Standard InCHI:	InChI=1S/C37H34N2O7/c1-39-15-13-24-19-32(43-4)36(44-5)37-33(24)27(39)16-21-6-11-28(41-2)30(17-21)45-25-9-7-22(8-10-25)35(40)34-26-20-31(46-37)29(42-3)18-23(26)12-14-38-34/h6-12,14,17-20,27H,13,15-16H2,1-5H3/t27-/m1/s1
SMILES:	CN1CCc2cc(c(c3c2[C@H]1Cc1ccc(c(c1)Oc1ccc(cc1)C(=O)c1c2cc(c(cc2ccn1)OC)O3)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO1179	Anaxagorea luzonensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10959592]
NPO755	Phoradendron reichenbachianum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11488459]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[20030508]
NPO3148	Melianthus major	Species	Melianthaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[32663024]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3728032]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12183	Argyreia nervosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11802	Physeter catodon	Species	Physeteridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12183	Argyreia nervosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11802	Physeter catodon	Species	Physeteridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11802	Physeter catodon	Species	Physeteridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12183	Argyreia nervosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1179	Anaxagorea luzonensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21826	Vulpicida juniperinus	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15367	Croton regelianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18003	Leptolyngbya lurida	Species	Leptolyngbyaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12663	Penicillium implicatum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2679	Dictyota bartayresiana	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12430	Erythrina chiriquensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11802	Physeter catodon	Species	Physeteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28111	Lathyrus aphaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22389	Phelipanche arenaria	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3148	Melianthus major	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5377	Tapinoma erraticum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12183	Argyreia nervosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5783	Acronychia muelleri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO755	Phoradendron reichenbachianum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12882	Clitocybe fasciculata	Species	Tricholomataceae	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 NPC268087 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	565
0.1-0.2	2816
0.2-0.3	12222
0.3-0.4	5108
0.4-0.5	8535
0.5-0.6	11300
0.6-0.7	1817
0.7-0.8	302
0.8-0.85	16
0.85-0.9	16
0.9-0.95	0
0.95-1	0

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 NPC268087 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	688
0.2-0.3	1016
0.3-0.4	1587
0.4-0.5	2547
0.5-0.6	2145
0.6-0.7	775
0.7-0.8	77
0.8-0.85	3
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