Structure

Physi-Chem Properties

Molecular Weight:  160.1
Volume:  157.121
LogP:  -2.806
LogD:  0.418
LogS:  -0.013
# Rotatable Bonds:  1
TPSA:  57.53
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.491
Synthetic Accessibility Score:  4.309
Fsp3:  0.857
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.247
MDCK Permeability:  0.0011585633037611842
Pgp-inhibitor:  0.0
Pgp-substrate:  0.016
Human Intestinal Absorption (HIA):  0.992
20% Bioavailability (F20%):  0.995
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.44
Plasma Protein Binding (PPB):  9.234642028808594%
Volume Distribution (VD):  0.679
Pgp-substrate:  95.74537658691406%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.087
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.045
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.231
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.432
CYP3A4-inhibitor:  0.003
CYP3A4-substrate:  0.006

ADMET: Excretion

Clearance (CL):  3.592
Half-life (T1/2):  0.925

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.014
Drug-inuced Liver Injury (DILI):  0.005
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.057
Maximum Recommended Daily Dose:  0.14
Skin Sensitization:  0.223
Carcinogencity:  0.151
Eye Corrosion:  0.242
Eye Irritation:  0.761
Respiratory Toxicity:  0.768

Download Data

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

  Natural Product: NPC99672

Natural Product ID:  NPC99672
Common Name*:   WTBNMEWVZFFAPJ-PHDIDXHHSA-O
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  WTBNMEWVZFFAPJ-PHDIDXHHSA-O
Standard InCHI:  InChI=1S/C7H13NO3/c1-8(2)3-5(7(10)11)6(9)4-8/h5-6,9H,3-4H2,1-2H3/p+1/t5-,6-/m1/s1
SMILES:  C[N+]1(C)C[C@H]([C@@H](C1)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   1801303
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000218] Pyrrolidines
        • [CHEMONTID:0001903] Pyrrolidine carboxylic acids and derivatives
          • [CHEMONTID:0002416] Pyrrolidine carboxylic acids

*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
NPO27978 Crossosoma bigelovii Species Crossosomataceae Eukaryota n.a. leaf n.a. DOI[10.1021/np8006342]
NPO27978 Crossosoma bigelovii Species Crossosomataceae Eukaryota n.a. flower n.a. DOI[10.1021/np8006342]
NPO27978 Crossosoma bigelovii Species Crossosomataceae Eukaryota n.a. twig n.a. DOI[10.1021/np8006342]
NPO27978 Crossosoma bigelovii Species Crossosomataceae Eukaryota n.a. fruit n.a. DOI[10.1021/np8006342]
NPO28619 Carex distachya Species Cyperaceae Eukaryota leaves n.a. n.a. PMID[16971124]
NPO28619 Carex distachya Species Cyperaceae Eukaryota leaves n.a. n.a. PMID[17112723]
NPO27978 Crossosoma bigelovii Species Crossosomataceae Eukaryota n.a. leaf n.a. PMID[19405508]
NPO27978 Crossosoma bigelovii Species Crossosomataceae Eukaryota n.a. flower n.a. PMID[19405508]
NPO27978 Crossosoma bigelovii Species Crossosomataceae Eukaryota n.a. twig n.a. PMID[19405508]
NPO27978 Crossosoma bigelovii Species Crossosomataceae Eukaryota n.a. fruit n.a. PMID[19405508]
NPO27978 Crossosoma bigelovii Species Crossosomataceae Eukaryota n.a. n.a. n.a. PMID[19405508]
NPO28473 Piper banksii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28473 Piper banksii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28619 Carex distachya Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28473 Piper banksii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27978 Crossosoma bigelovii Species Crossosomataceae 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 NPC99672 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

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 NPC99672 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

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