NPASS Compound

Structure

NPC6581 OpenBabel06302215102D 36 39 0 0 1 0 0 0 0 0999 V2000 2.6637 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1762 -0.8444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8444 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2577 -2.1149 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8611 -3.0056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8915 -2.9037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -1.9500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7191 -2.0519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2114 -1.9122 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2025 -0.9372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1216 -1.5628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7352 -2.3205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2042 -3.1382 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5536 -4.0484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3113 -4.6620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4638 -3.6990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9400 -4.8062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2624 -2.8859 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 -0.4875 0.8444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4875 0.8444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4875 2.5331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4625 2.5331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.3775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4875 4.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.9750 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 2 36 1 0 0 0 0 4 2 1 6 0 0 0 4 5 1 0 0 0 0 4 28 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 16 1 0 0 0 0 7 8 1 6 0 0 0 7 9 1 0 0 0 0 9 10 1 6 0 0 0 9 28 1 0 0 0 0 10 11 1 0 0 0 0 12 11 1 1 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 6 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 1 0 0 0 18 27 1 0 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 1 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 28 29 1 6 0 0 0 28 30 1 0 0 0 0 30 31 1 0 0 0 0 31 32 1 0 0 0 0 32 33 2 0 0 0 0 32 34 1 0 0 0 0 34 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.4
Volume:	551.821
LogP:	5.32
LogD:	4.861
LogS:	-4.746
# Rotatable Bonds:	7
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	4.915
Fsp3:	0.968
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:	-4.957
MDCK Permeability:	3.6484630982158706e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.768

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	90.26021575927734%
Volume Distribution (VD):	0.965
Pgp-substrate:	2.802467107772827%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.399
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.16
CYP2C9-substrate:	0.244
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.363
CYP3A4-inhibitor:	0.412
CYP3A4-substrate:	0.314

ADMET: Excretion

Clearance (CL):	3.897
Half-life (T1/2):	0.226

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.946
Carcinogencity:	0.012
Eye Corrosion:	0.283
Eye Irritation:	0.26
Respiratory Toxicity:	0.824

Download Data

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

Natural Product: NPC6581

Natural Product ID:	NPC6581
*Common Name:**	KMTSRTXGLOZVER-NWZPQFJUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KMTSRTXGLOZVER-NWZPQFJUSA-N
Standard InCHI:	InChI=1S/C31H54O5/c1-26(2,33)22-13-18-30(7)23(28(22,5)16-15-25(32)35-9)11-10-20-21(12-17-29(20,30)6)31(8)19-14-24(36-31)27(3,4)34/h20-24,33-34H,10-19H2,1-9H3/t20-,21+,22+,23-,24-,28+,29-,30-,31+/m1/s1
SMILES:	CC(C)([C@@H]1CC[C@]2(C)[C@H](CC[C@@H]3[C@H](CC[C@@]23C)[C@]2(C)CC[C@H](C(C)(C)O)O2)[C@@]1(C)CCC(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	70698185
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
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20939540]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21875098]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22817615]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24868863]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25089845]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28682072]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29883114]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9750	Dysoxylum malabaricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO819	Heliotropium olgae	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4668	Sideritis flavovirens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4372	Halimium halimifolium	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7674	Tragopogon orientalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7856	Streptomyces halstedii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2480	Amoora rohituka	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8578	Acacia rhodoxylon	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2633	Baccharis minutiflora	Species	Asteraceae	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 NPC6581 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	324
0.1-0.2	2830
0.2-0.3	11024
0.3-0.4	12130
0.4-0.5	5506
0.5-0.6	7123
0.6-0.7	3216
0.7-0.8	477
0.8-0.85	44
0.85-0.9	12
0.9-0.95	5
0.95-1	6

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 NPC6581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	3218
0.2-0.3	3686
0.3-0.4	1092
0.4-0.5	355
0.5-0.6	289
0.6-0.7	119
0.7-0.8	23
0.8-0.85	0
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