NPASS Compound

Structure

NPC197420 OpenBabel06302216002D 75 83 0 0 1 0 0 0 0 0999 V2000 7.7014 1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8457 0.9881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8457 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9900 -0.4940 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1343 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1343 0.9881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9900 1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2786 1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2786 2.4702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1343 2.9643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1343 3.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2786 4.4464 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2786 5.4345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4229 5.9286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4229 3.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4229 2.9643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5671 2.4702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7114 2.9643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7114 3.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8557 4.4464 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 3.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8557 4.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7114 3.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8557 5.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8557 2.4702 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8557 1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8557 1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7114 0.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7114 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5671 0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8557 -0.4940 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8557 -1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7114 -1.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5671 -1.4821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5671 -3.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5671 -0.4940 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4229 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2786 -0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2786 -1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -1.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9900 -1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8457 -1.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8338 -1.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3398 -1.1205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8457 -2.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9900 -3.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1343 -2.9643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1343 -3.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2786 -3.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4229 -2.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4229 -1.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5671 -2.4702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9900 -4.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8457 -4.9405 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7014 -4.4464 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5572 -4.9405 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5572 -5.9286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7014 -6.4226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8457 -5.9286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4129 -6.4226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4129 -4.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7014 -3.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9881 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4940 -0.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8557 5.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5671 4.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9900 4.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9900 2.4702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2786 -0.4940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9900 -1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7014 -0.4940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 4 1 0 0 0 0 3 75 1 6 0 0 0 4 5 1 0 0 0 0 4 74 1 1 0 0 0 5 6 1 0 0 0 0 5 73 1 1 0 0 0 6 7 1 0 0 0 0 6 8 1 6 0 0 0 9 8 1 1 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 72 1 6 0 0 0 11 12 1 0 0 0 0 11 71 1 6 0 0 0 12 13 1 6 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 6 0 0 0 18 17 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 70 1 6 0 0 0 20 21 1 0 0 0 0 20 69 1 1 0 0 0 21 22 1 6 0 0 0 21 25 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 6 0 0 0 28 27 1 6 0 0 0 28 29 1 0 0 0 0 28 65 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 31 38 1 0 0 0 0 31 32 1 6 0 0 0 31 33 1 0 0 0 0 33 34 1 6 0 0 0 33 65 1 0 0 0 0 34 35 1 0 0 0 0 35 36 1 0 0 0 0 36 53 1 0 0 0 0 36 37 1 6 0 0 0 36 38 1 0 0 0 0 38 39 1 6 0 0 0 39 40 1 0 0 0 0 40 41 2 0 0 0 0 41 53 1 0 0 0 0 41 42 1 0 0 0 0 42 43 1 1 0 0 0 42 49 1 0 0 0 0 43 44 1 0 0 0 0 44 45 1 0 0 0 0 44 46 1 0 0 0 0 44 47 1 0 0 0 0 47 48 1 0 0 0 0 48 49 1 0 0 0 0 48 55 1 6 0 0 0 49 50 1 6 0 0 0 49 51 1 0 0 0 0 51 52 1 0 0 0 0 52 53 1 0 0 0 0 53 54 1 1 0 0 0 56 55 1 6 0 0 0 56 57 1 0 0 0 0 56 61 1 0 0 0 0 57 58 1 0 0 0 0 57 64 1 1 0 0 0 58 59 1 0 0 0 0 58 63 1 6 0 0 0 59 60 1 0 0 0 0 59 62 1 1 0 0 0 60 61 1 0 0 0 0 65 66 1 1 0 0 0 65 67 1 0 0 0 0 67 68 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1074.56
Volume:	1036.348
LogP:	1.725
LogD:	1.459
LogS:	-3.083
# Rotatable Bonds:	11
TPSA:	353.9
# H-Bond Aceptor:	22
# H-Bond Donor:	13
# Rings:	9
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	6.845
Fsp3:	0.943
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.167
MDCK Permeability:	8.256186993094161e-05
Pgp-inhibitor:	0.558
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.989
20% Bioavailability (F20%):	0.253
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	66.17777252197266%
Volume Distribution (VD):	-0.051
Pgp-substrate:	16.561508178710938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.288
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.082
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.156
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC197420

Natural Product ID:	NPC197420
*Common Name:**	ZKJLHEOYIFBWLR-YAYQVEJMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZKJLHEOYIFBWLR-YAYQVEJMSA-N
Standard InCHI:	InChI=1S/C53H86O22/c1-22-31(57)34(60)39(65)45(69-22)74-41-35(61)33(59)26(19-54)70-46(41)75-42-37(63)36(62)40(43(66)67)73-47(42)71-29-12-13-50(5)27(51(29,6)21-55)11-14-53(8)28(50)10-9-23-24-17-48(2,3)18-30(49(24,4)15-16-52(23,53)7)72-44-38(64)32(58)25(56)20-68-44/h9,22,24-42,44-47,54-65H,10-21H2,1-8H3,(H,66,67)/t22-,24-,25+,26+,27+,28+,29-,30+,31-,32-,33-,34+,35-,36-,37-,38+,39+,40-,41+,42+,44-,45-,46-,47+,49+,50-,51+,52+,53+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H]([C@@H](CO)O[C@H]1O[C@@H]1[C@H]([C@@H]([C@@H](C(=O)O)O[C@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)C[C@H]([C@]4(C)CC[C@@]32C)O[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)[C@@]1(C)CO)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	101244079
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO20620	Eucalyptus cypellocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000030]
NPO17542	Aconitum orientale	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17315	Ceanothus integerrimus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17542	Aconitum orientale	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17315	Ceanothus integerrimus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20620	Eucalyptus cypellocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19504	Solanum canense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20346	Acacia retinoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18462	Calliactis parasitica	Species	Hormathiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20620	Eucalyptus cypellocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17315	Ceanothus integerrimus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17542	Aconitum orientale	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19033	Sargassum lacerifolium	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12227	Xylopia acutiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24375	Micrococcus luteus	Species	Micrococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23977	Helichrysum moeserianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15338	Lampranthus aurantiacus	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18125	Suillus variegatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20277	Pentzia eenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25819.1	Gueldenstaedtia verna subsp. multiflora	Subspecies	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 NPC197420 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	282
0.1-0.2	1992
0.2-0.3	5500
0.3-0.4	10948
0.4-0.5	10876
0.5-0.6	6687
0.6-0.7	3662
0.7-0.8	1846
0.8-0.85	332
0.85-0.9	114
0.9-0.95	337
0.95-1	121

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 NPC197420 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	2284
0.2-0.3	3889
0.3-0.4	1740
0.4-0.5	564
0.5-0.6	246
0.6-0.7	123
0.7-0.8	35
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

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