Structure

Physi-Chem Properties

Molecular Weight:  272.27
Volume:  320.169
LogP:  5.186
LogD:  3.669
LogS:  -4.695
# Rotatable Bonds:  15
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.42
Synthetic Accessibility Score:  2.456
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.7
MDCK Permeability:  2.5293611543020234e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.452
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.305
30% Bioavailability (F30%):  0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.107
Plasma Protein Binding (PPB):  96.23674774169922%
Volume Distribution (VD):  1.222
Pgp-substrate:  2.3496317863464355%

ADMET: Metabolism

CYP1A2-inhibitor:  0.441
CYP1A2-substrate:  0.211
CYP2C19-inhibitor:  0.246
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.168
CYP2C9-substrate:  0.919
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.055
CYP3A4-inhibitor:  0.116
CYP3A4-substrate:  0.041

ADMET: Excretion

Clearance (CL):  9.2
Half-life (T1/2):  0.309

ADMET: Toxicity

hERG Blockers:  0.184
Human Hepatotoxicity (H-HT):  0.02
Drug-inuced Liver Injury (DILI):  0.021
AMES Toxicity:  0.005
Rat Oral Acute Toxicity:  0.01
Maximum Recommended Daily Dose:  0.036
Skin Sensitization:  0.951
Carcinogencity:  0.045
Eye Corrosion:  0.978
Eye Irritation:  0.98
Respiratory Toxicity:  0.221

Download Data

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

  Natural Product: NPC474914

Natural Product ID:  NPC474914
Common Name*:   Heptadecane-1,14-Diol
IUPAC Name:   heptadecane-1,14-diol
Synonyms:   Heptadecane-1,14-Diol
Standard InCHIKey:  LVOWTTRTDYAFAN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C17H36O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h17-19H,2-16H2,1H3
SMILES:  CCCC(CCCCCCCCCCCCCO)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL487401
PubChem CID:   44559588
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] Fatty alcohols
          • [CHEMONTID:0002951] Long-chain fatty alcohols

*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
NPO18052 Cicuta maculata Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[3572419]
NPO18052 Cicuta maculata Species Apiaceae 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
NPT91 Cell Line KB Homo sapiens ED50 > 4.0 ug ml-1 PMID[465781]

☑ 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 NPC474914 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
1.0 High Similarity NPC474392
0.9697 High Similarity NPC97967
0.9091 High Similarity NPC319034
0.9091 High Similarity NPC185538
0.9091 High Similarity NPC139131
0.9091 High Similarity NPC272998
0.9091 High Similarity NPC152759
0.9091 High Similarity NPC205141
0.9091 High Similarity NPC12231
0.9091 High Similarity NPC1748
0.9091 High Similarity NPC66124
0.9091 High Similarity NPC193062
0.9091 High Similarity NPC181516
0.9091 High Similarity NPC72324
0.9091 High Similarity NPC291158
0.8788 High Similarity NPC126915
0.8788 High Similarity NPC267243
0.8788 High Similarity NPC122962
0.8649 High Similarity NPC471282
0.8611 High Similarity NPC74352
0.8485 Intermediate Similarity NPC163556
0.8485 Intermediate Similarity NPC236797
0.8485 Intermediate Similarity NPC225783
0.8485 Intermediate Similarity NPC147096
0.8485 Intermediate Similarity NPC112242
0.8485 Intermediate Similarity NPC24506
0.8485 Intermediate Similarity NPC185041
0.8182 Intermediate Similarity NPC110884
0.8049 Intermediate Similarity NPC469781
0.7895 Intermediate Similarity NPC197039
0.7879 Intermediate Similarity NPC279895
0.7879 Intermediate Similarity NPC159845
0.7778 Intermediate Similarity NPC139569
0.7692 Intermediate Similarity NPC221022
0.7674 Intermediate Similarity NPC328497
0.7674 Intermediate Similarity NPC324004
0.7619 Intermediate Similarity NPC215358
0.7619 Intermediate Similarity NPC62014
0.75 Intermediate Similarity NPC152008
0.75 Intermediate Similarity NPC106872
0.7442 Intermediate Similarity NPC473914
0.7297 Intermediate Similarity NPC474120
0.7297 Intermediate Similarity NPC474089
0.7273 Intermediate Similarity NPC560
0.7273 Intermediate Similarity NPC8597
0.7179 Intermediate Similarity NPC177022
0.7174 Intermediate Similarity NPC90904
0.7073 Intermediate Similarity NPC160261
0.7073 Intermediate Similarity NPC469759
0.7045 Intermediate Similarity NPC12438
0.7045 Intermediate Similarity NPC30195
0.6977 Remote Similarity NPC76051
0.697 Remote Similarity NPC232554
0.697 Remote Similarity NPC275462
0.697 Remote Similarity NPC213764
0.6957 Remote Similarity NPC304162
0.6889 Remote Similarity NPC289484
0.6889 Remote Similarity NPC319709
0.6875 Remote Similarity NPC123814
0.6875 Remote Similarity NPC474322
0.6857 Remote Similarity NPC325345
0.6842 Remote Similarity NPC283682
0.6818 Remote Similarity NPC240994
0.6757 Remote Similarity NPC272426
0.675 Remote Similarity NPC128996
0.6739 Remote Similarity NPC131770
0.6739 Remote Similarity NPC200618
0.6735 Remote Similarity NPC270041
0.6667 Remote Similarity NPC76976
0.6667 Remote Similarity NPC245688
0.66 Remote Similarity NPC23155
0.66 Remote Similarity NPC469937
0.66 Remote Similarity NPC320588
0.66 Remote Similarity NPC53463
0.66 Remote Similarity NPC289979
0.6591 Remote Similarity NPC144891
0.6591 Remote Similarity NPC74845
0.6522 Remote Similarity NPC223468
0.6522 Remote Similarity NPC84030
0.6522 Remote Similarity NPC198540
0.6522 Remote Similarity NPC147343
0.6522 Remote Similarity NPC287550
0.6522 Remote Similarity NPC176309
0.6512 Remote Similarity NPC307783
0.6512 Remote Similarity NPC149184
0.6512 Remote Similarity NPC171736
0.6512 Remote Similarity NPC209970
0.6512 Remote Similarity NPC216630
0.6512 Remote Similarity NPC196924
0.6512 Remote Similarity NPC474361
0.6471 Remote Similarity NPC88887
0.6444 Remote Similarity NPC47363
0.6444 Remote Similarity NPC287231
0.6429 Remote Similarity NPC31557
0.6429 Remote Similarity NPC28394
0.64 Remote Similarity NPC474496
0.64 Remote Similarity NPC477724
0.64 Remote Similarity NPC26102
0.64 Remote Similarity NPC187361
0.6389 Remote Similarity NPC223195
0.6383 Remote Similarity NPC29222
0.6383 Remote Similarity NPC121062
0.6383 Remote Similarity NPC96966
0.6364 Remote Similarity NPC52403
0.6364 Remote Similarity NPC249801
0.6364 Remote Similarity NPC39977
0.6364 Remote Similarity NPC46248
0.6364 Remote Similarity NPC67462
0.6346 Remote Similarity NPC148424
0.6346 Remote Similarity NPC8979
0.6327 Remote Similarity NPC473672
0.6327 Remote Similarity NPC100096
0.6327 Remote Similarity NPC474495
0.6286 Remote Similarity NPC252154
0.6275 Remote Similarity NPC49059
0.6275 Remote Similarity NPC256209
0.625 Remote Similarity NPC86412
0.625 Remote Similarity NPC325034
0.625 Remote Similarity NPC66052
0.625 Remote Similarity NPC86545
0.625 Remote Similarity NPC196442
0.625 Remote Similarity NPC293908
0.625 Remote Similarity NPC301398
0.625 Remote Similarity NPC223374
0.625 Remote Similarity NPC192065
0.625 Remote Similarity NPC26253
0.6226 Remote Similarity NPC322148
0.6222 Remote Similarity NPC252978
0.6176 Remote Similarity NPC199270
0.6154 Remote Similarity NPC477725
0.6154 Remote Similarity NPC147054
0.6154 Remote Similarity NPC477726
0.6136 Remote Similarity NPC241279
0.6098 Remote Similarity NPC61665
0.6098 Remote Similarity NPC328441
0.6087 Remote Similarity NPC8219
0.6078 Remote Similarity NPC161473
0.6061 Remote Similarity NPC299484
0.6047 Remote Similarity NPC201844
0.6047 Remote Similarity NPC14227
0.6047 Remote Similarity NPC154186
0.6047 Remote Similarity NPC113928
0.6047 Remote Similarity NPC261080
0.6047 Remote Similarity NPC279026
0.6047 Remote Similarity NPC301696
0.6047 Remote Similarity NPC301585
0.6042 Remote Similarity NPC314087
0.6038 Remote Similarity NPC471960
0.6038 Remote Similarity NPC475384
0.6038 Remote Similarity NPC470968
0.6038 Remote Similarity NPC470967
0.6038 Remote Similarity NPC473847
0.6038 Remote Similarity NPC471443
0.6038 Remote Similarity NPC477661
0.6038 Remote Similarity NPC470969
0.6038 Remote Similarity NPC471605
0.6038 Remote Similarity NPC161838
0.6038 Remote Similarity NPC470966
0.6 Remote Similarity NPC319131
0.6 Remote Similarity NPC129972
0.6 Remote Similarity NPC470363
0.6 Remote Similarity NPC474126
0.6 Remote Similarity NPC203531
0.6 Remote Similarity NPC71317
0.6 Remote Similarity NPC122239
0.6 Remote Similarity NPC174485
0.6 Remote Similarity NPC307022
0.6 Remote Similarity NPC236579
0.6 Remote Similarity NPC474125
0.6 Remote Similarity NPC286498
0.6 Remote Similarity NPC301528
0.6 Remote Similarity NPC140389
0.5957 Remote Similarity NPC87439
0.5952 Remote Similarity NPC277333
0.5946 Remote Similarity NPC52362
0.5926 Remote Similarity NPC135438
0.5926 Remote Similarity NPC52012
0.5926 Remote Similarity NPC474577
0.5926 Remote Similarity NPC470970
0.5909 Remote Similarity NPC28598
0.5909 Remote Similarity NPC161097
0.5897 Remote Similarity NPC187058
0.5897 Remote Similarity NPC182541
0.5897 Remote Similarity NPC197207
0.5897 Remote Similarity NPC149070
0.5897 Remote Similarity NPC127074
0.5893 Remote Similarity NPC477753
0.5893 Remote Similarity NPC477757
0.5893 Remote Similarity NPC477750
0.5893 Remote Similarity NPC477755
0.5893 Remote Similarity NPC243532
0.5893 Remote Similarity NPC477762
0.5893 Remote Similarity NPC477763
0.587 Remote Similarity NPC19305
0.587 Remote Similarity NPC255837
0.5849 Remote Similarity NPC475353
0.5849 Remote Similarity NPC281590
0.5849 Remote Similarity NPC473725
0.5849 Remote Similarity NPC471269
0.5849 Remote Similarity NPC473721

  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 NPC474914 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
0.9091 High Similarity NPD5383 Approved
0.9091 High Similarity NPD2272 Approved
0.75 Intermediate Similarity NPD7536 Approved
0.6889 Remote Similarity NPD3211 Approved
0.6875 Remote Similarity NPD3215 Phase 1
0.6857 Remote Similarity NPD8988 Clinical (unspecified phase)
0.6809 Remote Similarity NPD3214 Discontinued
0.6757 Remote Similarity NPD907 Approved
0.6757 Remote Similarity NPD908 Approved
0.6757 Remote Similarity NPD1461 Approved
0.66 Remote Similarity NPD3729 Clinical (unspecified phase)
0.66 Remote Similarity NPD3730 Approved
0.66 Remote Similarity NPD3728 Approved
0.6522 Remote Similarity NPD384 Approved
0.6522 Remote Similarity NPD385 Approved
0.6512 Remote Similarity NPD2270 Approved
0.6444 Remote Similarity NPD2699 Approved
0.6429 Remote Similarity NPD5799 Discontinued
0.6364 Remote Similarity NPD1462 Approved
0.6279 Remote Similarity NPD1460 Approved
0.625 Remote Similarity NPD9052 Approved
0.625 Remote Similarity NPD9053 Approved
0.625 Remote Similarity NPD9051 Approved
0.6087 Remote Similarity NPD3199 Clinical (unspecified phase)
0.6047 Remote Similarity NPD633 Phase 3
0.6047 Remote Similarity NPD9448 Phase 2
0.6 Remote Similarity NPD3198 Approved
0.5957 Remote Similarity NPD1152 Phase 2
0.5897 Remote Similarity NPD8814 Phase 3
0.5814 Remote Similarity NPD3206 Approved
0.5741 Remote Similarity NPD2267 Suspended
0.5714 Remote Similarity NPD6125 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8225 Phase 3
0.5714 Remote Similarity NPD370 Phase 3
0.5682 Remote Similarity NPD9655 Approved
0.5625 Remote Similarity NPD388 Approved
0.5625 Remote Similarity NPD386 Approved

  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