Structure

Physi-Chem Properties

Molecular Weight:  305.24
Volume:  340.735
LogP:  4.963
LogD:  3.989
LogS:  -3.9
# Rotatable Bonds:  8
TPSA:  42.09
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.697
Synthetic Accessibility Score:  3.127
Fsp3:  0.737
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:  -4.832
MDCK Permeability:  1.6444315406261012e-05
Pgp-inhibitor:  0.046
Pgp-substrate:  0.355
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.943
30% Bioavailability (F30%):  0.701

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.355
Plasma Protein Binding (PPB):  99.18663787841797%
Volume Distribution (VD):  2.115
Pgp-substrate:  1.7518305778503418%

ADMET: Metabolism

CYP1A2-inhibitor:  0.698
CYP1A2-substrate:  0.968
CYP2C19-inhibitor:  0.811
CYP2C19-substrate:  0.76
CYP2C9-inhibitor:  0.716
CYP2C9-substrate:  0.947
CYP2D6-inhibitor:  0.763
CYP2D6-substrate:  0.689
CYP3A4-inhibitor:  0.72
CYP3A4-substrate:  0.516

ADMET: Excretion

Clearance (CL):  2.679
Half-life (T1/2):  0.22

ADMET: Toxicity

hERG Blockers:  0.114
Human Hepatotoxicity (H-HT):  0.162
Drug-inuced Liver Injury (DILI):  0.108
AMES Toxicity:  0.094
Rat Oral Acute Toxicity:  0.45
Maximum Recommended Daily Dose:  0.935
Skin Sensitization:  0.943
Carcinogencity:  0.059
Eye Corrosion:  0.016
Eye Irritation:  0.332
Respiratory Toxicity:  0.956

Download Data

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

  Natural Product: NPC472161

Natural Product ID:  NPC472161
Common Name*:   HVCQMOJYUXVKJI-OAHLLOKOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  HVCQMOJYUXVKJI-OAHLLOKOSA-N
Standard InCHI:  InChI=1S/C19H31NO2/c1-4-5-6-7-8-9-11-15-12-10-13-16-17(15)18(21)19(22-3)14(2)20-16/h15H,4-13H2,1-3H3,(H,20,21)/t15-/m1/s1
SMILES:  CCCCCCCCC1CCCC2=C1C(=O)C(=C(N2)C)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3342748
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000254] Ethers
          • [CHEMONTID:0000128] Alkyl aryl ethers

*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
NPO22669 Waltheria indica Species Malvaceae Eukaryota roots n.a. n.a. PMID[25314007]
NPO22669 Waltheria indica Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[26848627]
NPO22669 Waltheria indica Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[33095014]
NPO22669 Waltheria indica Species Malvaceae 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
NPT839 Cell Line L6 Rattus norvegicus IC50 = 750.0 nM PMID[553250]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 32600.0 nM PMID[553250]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 > 100000.0 nM PMID[553250]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 490.0 nM PMID[553250]
NPT2 Others Unspecified Ratio IC50 = 1.5 n.a. PMID[553250]

☑ 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 NPC472161 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
0.9756 High Similarity NPC116231
0.9048 High Similarity NPC472136
0.8889 High Similarity NPC472162
0.8085 Intermediate Similarity NPC472166
0.8085 Intermediate Similarity NPC472167
0.6909 Remote Similarity NPC472164
0.6889 Remote Similarity NPC23778
0.6796 Remote Similarity NPC34193
0.6778 Remote Similarity NPC283087
0.6762 Remote Similarity NPC87919
0.6667 Remote Similarity NPC474085
0.6562 Remote Similarity NPC475614
0.6548 Remote Similarity NPC34622
0.6548 Remote Similarity NPC474400
0.6526 Remote Similarity NPC8091
0.6471 Remote Similarity NPC98897
0.6452 Remote Similarity NPC475681
0.6429 Remote Similarity NPC5485
0.6429 Remote Similarity NPC57463
0.6429 Remote Similarity NPC151728
0.6422 Remote Similarity NPC24596
0.64 Remote Similarity NPC236322
0.6395 Remote Similarity NPC16119
0.6392 Remote Similarity NPC263997
0.6392 Remote Similarity NPC132228
0.6392 Remote Similarity NPC241512
0.6392 Remote Similarity NPC6185
0.6392 Remote Similarity NPC8518
0.6392 Remote Similarity NPC133652
0.6389 Remote Similarity NPC185929
0.6364 Remote Similarity NPC318578
0.633 Remote Similarity NPC176773
0.6322 Remote Similarity NPC243272
0.6322 Remote Similarity NPC474619
0.6316 Remote Similarity NPC7905
0.6316 Remote Similarity NPC315652
0.6306 Remote Similarity NPC72688
0.6304 Remote Similarity NPC92080
0.6281 Remote Similarity NPC472165
0.6262 Remote Similarity NPC251884
0.6261 Remote Similarity NPC27413
0.6261 Remote Similarity NPC271621
0.6261 Remote Similarity NPC59751
0.625 Remote Similarity NPC125578
0.625 Remote Similarity NPC263382
0.625 Remote Similarity NPC146376
0.625 Remote Similarity NPC134385
0.6238 Remote Similarity NPC223093
0.6224 Remote Similarity NPC90287
0.6222 Remote Similarity NPC474539
0.6207 Remote Similarity NPC296361
0.6196 Remote Similarity NPC175079
0.6186 Remote Similarity NPC471595
0.618 Remote Similarity NPC94488
0.618 Remote Similarity NPC262673
0.617 Remote Similarity NPC30321
0.6162 Remote Similarity NPC203795
0.6147 Remote Similarity NPC9436
0.6146 Remote Similarity NPC312419
0.6146 Remote Similarity NPC478262
0.6129 Remote Similarity NPC26504
0.6111 Remote Similarity NPC291062
0.6111 Remote Similarity NPC94743
0.6111 Remote Similarity NPC173321
0.6102 Remote Similarity NPC473808
0.6087 Remote Similarity NPC264178
0.6087 Remote Similarity NPC147438
0.6087 Remote Similarity NPC176336
0.6078 Remote Similarity NPC475823
0.6078 Remote Similarity NPC474209
0.6071 Remote Similarity NPC473494
0.6061 Remote Similarity NPC76283
0.6061 Remote Similarity NPC478245
0.6061 Remote Similarity NPC2640
0.6061 Remote Similarity NPC474680
0.605 Remote Similarity NPC315915
0.6042 Remote Similarity NPC108955
0.604 Remote Similarity NPC53454
0.6019 Remote Similarity NPC166110
0.6 Remote Similarity NPC476808
0.6 Remote Similarity NPC478246
0.6 Remote Similarity NPC469996
0.6 Remote Similarity NPC133420
0.6 Remote Similarity NPC315011
0.6 Remote Similarity NPC478247
0.598 Remote Similarity NPC280833
0.5979 Remote Similarity NPC474353
0.5979 Remote Similarity NPC99308
0.5979 Remote Similarity NPC55869
0.5979 Remote Similarity NPC225515
0.5966 Remote Similarity NPC315110
0.5962 Remote Similarity NPC248193
0.5938 Remote Similarity NPC192329
0.5938 Remote Similarity NPC476177
0.5918 Remote Similarity NPC103486
0.5909 Remote Similarity NPC61473
0.5895 Remote Similarity NPC472300
0.5882 Remote Similarity NPC478261
0.5882 Remote Similarity NPC478259
0.5882 Remote Similarity NPC307298
0.5882 Remote Similarity NPC478260
0.5882 Remote Similarity NPC475001
0.5882 Remote Similarity NPC185059
0.5876 Remote Similarity NPC18955
0.5865 Remote Similarity NPC248913
0.5862 Remote Similarity NPC477830
0.5862 Remote Similarity NPC53109
0.5862 Remote Similarity NPC143168
0.5859 Remote Similarity NPC105803
0.5859 Remote Similarity NPC288281
0.5849 Remote Similarity NPC31021
0.5841 Remote Similarity NPC220730
0.5833 Remote Similarity NPC13351
0.5825 Remote Similarity NPC142159
0.5825 Remote Similarity NPC95364
0.5816 Remote Similarity NPC475833
0.5816 Remote Similarity NPC149237
0.5804 Remote Similarity NPC195841
0.5804 Remote Similarity NPC233256
0.5802 Remote Similarity NPC473955
0.58 Remote Similarity NPC60951
0.58 Remote Similarity NPC474359
0.5795 Remote Similarity NPC7029
0.5789 Remote Similarity NPC470525
0.5789 Remote Similarity NPC110725
0.5789 Remote Similarity NPC40353
0.5784 Remote Similarity NPC220930
0.5784 Remote Similarity NPC272039
0.5773 Remote Similarity NPC27817
0.5773 Remote Similarity NPC622
0.5773 Remote Similarity NPC254996
0.5773 Remote Similarity NPC268502
0.5773 Remote Similarity NPC276647
0.5769 Remote Similarity NPC478257
0.5769 Remote Similarity NPC478258
0.5769 Remote Similarity NPC113393
0.5758 Remote Similarity NPC321289
0.5758 Remote Similarity NPC327969
0.5755 Remote Similarity NPC212812
0.5745 Remote Similarity NPC470299
0.5743 Remote Similarity NPC470177
0.5743 Remote Similarity NPC32037
0.5727 Remote Similarity NPC77703
0.5714 Remote Similarity NPC470036
0.5714 Remote Similarity NPC174167
0.5714 Remote Similarity NPC2482
0.5714 Remote Similarity NPC250632
0.5714 Remote Similarity NPC32944
0.5714 Remote Similarity NPC474956
0.5714 Remote Similarity NPC193396
0.5714 Remote Similarity NPC304795
0.5714 Remote Similarity NPC26865
0.5702 Remote Similarity NPC470535
0.5701 Remote Similarity NPC91408
0.5701 Remote Similarity NPC279313
0.57 Remote Similarity NPC53733
0.57 Remote Similarity NPC258985
0.5699 Remote Similarity NPC84790
0.569 Remote Similarity NPC44733
0.5686 Remote Similarity NPC470345
0.5686 Remote Similarity NPC229717
0.5686 Remote Similarity NPC322672
0.5686 Remote Similarity NPC94666
0.568 Remote Similarity NPC473249
0.567 Remote Similarity NPC475994
0.567 Remote Similarity NPC189485
0.567 Remote Similarity NPC178852
0.567 Remote Similarity NPC471220
0.566 Remote Similarity NPC476753
0.566 Remote Similarity NPC476752
0.566 Remote Similarity NPC263780
0.566 Remote Similarity NPC271652
0.5657 Remote Similarity NPC121984
0.5652 Remote Similarity NPC274895
0.5652 Remote Similarity NPC474060
0.5652 Remote Similarity NPC469914
0.5652 Remote Similarity NPC470536
0.5652 Remote Similarity NPC477449
0.5652 Remote Similarity NPC477448
0.5648 Remote Similarity NPC476449
0.5644 Remote Similarity NPC320801
0.5644 Remote Similarity NPC469569
0.5644 Remote Similarity NPC237712
0.5636 Remote Similarity NPC128698
0.5636 Remote Similarity NPC239768
0.5631 Remote Similarity NPC473525
0.5631 Remote Similarity NPC471739
0.5631 Remote Similarity NPC38885
0.5625 Remote Similarity NPC473223
0.5625 Remote Similarity NPC180886
0.5625 Remote Similarity NPC320154
0.5625 Remote Similarity NPC263582
0.5625 Remote Similarity NPC1254
0.5619 Remote Similarity NPC469464
0.5612 Remote Similarity NPC471740
0.5612 Remote Similarity NPC281138
0.5607 Remote Similarity NPC476754
0.5607 Remote Similarity NPC477439

  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 NPC472161 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
0.6522 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6395 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6395 Remote Similarity NPD3704 Approved
0.6042 Remote Similarity NPD4695 Discontinued
0.6 Remote Similarity NPD3617 Approved
0.6 Remote Similarity NPD2101 Approved
0.5966 Remote Similarity NPD7196 Clinical (unspecified phase)
0.5917 Remote Similarity NPD7739 Clinical (unspecified phase)
0.5909 Remote Similarity NPD7341 Phase 2
0.5868 Remote Similarity NPD7623 Phase 3
0.5868 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5862 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5859 Remote Similarity NPD3527 Clinical (unspecified phase)
0.5826 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5729 Remote Similarity NPD4756 Discovery
0.5728 Remote Similarity NPD6672 Approved
0.5728 Remote Similarity NPD5737 Approved
0.568 Remote Similarity NPD7746 Phase 1
0.568 Remote Similarity NPD7747 Phase 1
0.5667 Remote Similarity NPD7331 Phase 2
0.5604 Remote Similarity NPD3709 Clinical (unspecified phase)

  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