Structure

Physi-Chem Properties

Molecular Weight:  222.2
Volume:  257.037
LogP:  4.031
LogD:  3.789
LogS:  -3.55
# Rotatable Bonds:  1
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.667
Synthetic Accessibility Score:  4.181
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.541
MDCK Permeability:  1.542768040962983e-05
Pgp-inhibitor:  0.313
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.086
30% Bioavailability (F30%):  0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.386
Plasma Protein Binding (PPB):  97.45909881591797%
Volume Distribution (VD):  1.862
Pgp-substrate:  2.034813642501831%

ADMET: Metabolism

CYP1A2-inhibitor:  0.164
CYP1A2-substrate:  0.549
CYP2C19-inhibitor:  0.066
CYP2C19-substrate:  0.797
CYP2C9-inhibitor:  0.225
CYP2C9-substrate:  0.644
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.639
CYP3A4-inhibitor:  0.191
CYP3A4-substrate:  0.374

ADMET: Excretion

Clearance (CL):  7.932
Half-life (T1/2):  0.163

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.057
Drug-inuced Liver Injury (DILI):  0.361
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.05
Maximum Recommended Daily Dose:  0.398
Skin Sensitization:  0.044
Carcinogencity:  0.488
Eye Corrosion:  0.004
Eye Irritation:  0.389
Respiratory Toxicity:  0.234

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Similar NPs/Drugs  

  Natural Product: NPC261228

Natural Product ID:  NPC261228
Common Name*:   TWVJWDMOZJXUID-HTAVTVPLSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  TWVJWDMOZJXUID-HTAVTVPLSA-N
Standard InCHI:  InChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3/t10?,11?,12-/m1/s1
SMILES:  CC1CC[C@H](CC2=C1CCC2C)C(C)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   9899341
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO3359 Psidium guajava Species Myrtaceae Eukaryota n.a. leaf n.a. DOI[10.1016/j.foodchem.2010.03.088]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00119-3]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. seed n.a. DOI[10.1016/S0031-9422(99)00216-2]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[1659613]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. root n.a. PMID[17238120]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota stem bark n.a. n.a. PMID[17918910]
NPO15388 Eucalyptus globulus Species Myrtaceae Eukaryota n.a. fruit n.a. PMID[18020353]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. root n.a. PMID[18405608]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. root n.a. PMID[18661821]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. rhizome n.a. PMID[18787781]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota Stems; Barks n.a. n.a. PMID[19086868]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota stems n.a. n.a. PMID[20387902]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. rhizome n.a. PMID[20707067]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. root n.a. PMID[20707067]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[21302967]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21417376]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21627108]
NPO15388 Eucalyptus globulus Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[22934600]
NPO15388 Eucalyptus globulus Species Myrtaceae Eukaryota n.a. whole plant n.a. PMID[23678820]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. bark n.a. PMID[23823874]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25333853]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota seeds and root bark Henan, China n.a. PMID[26295746]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27228227]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[28485933]
NPO15388 Eucalyptus globulus Species Myrtaceae Eukaryota Fruits n.a. n.a. PMID[30543429]
NPO15388 Eucalyptus globulus Species Myrtaceae Eukaryota Fruits n.a. n.a. PMID[30848923]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[31738062]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[4013523]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. root n.a. PMID[7700984]
NPO15388 Eucalyptus globulus Species Myrtaceae Eukaryota Leaves n.a. n.a. PMID[8864235]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[9544564]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO15388 Eucalyptus globulus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10597 Fructus syzygii n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO319 Citrus limon Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15388 Eucalyptus globulus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10597 Fructus syzygii n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15388 Eucalyptus globulus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15388 Eucalyptus globulus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3359 Psidium guajava Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29334 Oplopanax elatus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22273 Angelica pubescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16087 Atractylodes lancea 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 NPC261228 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 NPC261228 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