Structure

Physi-Chem Properties

Molecular Weight:  368.18
Volume:  365.133
LogP:  2.077
LogD:  1.24
LogS:  -3.425
# Rotatable Bonds:  6
TPSA:  94.73
# H-Bond Aceptor:  7
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.424
Synthetic Accessibility Score:  5.396
Fsp3:  0.842
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.044
MDCK Permeability:  5.424381379270926e-05
Pgp-inhibitor:  0.778
Pgp-substrate:  0.011
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.041
30% Bioavailability (F30%):  0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.965
Plasma Protein Binding (PPB):  37.05154800415039%
Volume Distribution (VD):  1.848
Pgp-substrate:  52.53001022338867%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.106
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.295
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.017
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.062
CYP3A4-inhibitor:  0.571
CYP3A4-substrate:  0.436

ADMET: Excretion

Clearance (CL):  3.894
Half-life (T1/2):  0.63

ADMET: Toxicity

hERG Blockers:  0.049
Human Hepatotoxicity (H-HT):  0.622
Drug-inuced Liver Injury (DILI):  0.672
AMES Toxicity:  0.863
Rat Oral Acute Toxicity:  0.108
Maximum Recommended Daily Dose:  0.023
Skin Sensitization:  0.953
Carcinogencity:  0.543
Eye Corrosion:  0.861
Eye Irritation:  0.403
Respiratory Toxicity:  0.902

Download Data

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

  Natural Product: NPC108014

Natural Product ID:  NPC108014
Common Name*:   Pulicanaral B
IUPAC Name:   n.a.
Synonyms:   Pulicanaral B
Standard InCHIKey:  FZHYVARJPXGTKX-HQPSDWMKSA-N
Standard InCHI:  InChI=1S/C19H28O7/c1-10(2)15-13(23-11(3)21)8-19(9-20)14(25-19)6-7-18(5)17(26-18)16(15)24-12(4)22/h9-10,13-17H,6-8H2,1-5H3/t13-,14-,15+,16+,17+,18-,19-/m1/s1
SMILES:  O=C[C@@]12C[C@@H](OC(=O)C)[C@H](C(C)C)[C@H](OC(=O)C)[C@H]3[C@](CC[C@H]2O1)(C)O3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL481041
PubChem CID:   44575374
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002456] Germacrane 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
NPO1119 Pulicaria canariensis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15844941]
NPO1119 Pulicaria canariensis 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 264000.0 nM PMID[482947]

☑ 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 NPC108014 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
0.8267 Intermediate Similarity NPC96322
0.7875 Intermediate Similarity NPC470014
0.75 Intermediate Similarity NPC475971
0.7356 Intermediate Similarity NPC475491
0.7356 Intermediate Similarity NPC469626
0.7128 Intermediate Similarity NPC471140
0.7108 Intermediate Similarity NPC474003
0.7033 Intermediate Similarity NPC65359
0.7013 Intermediate Similarity NPC469926
0.6957 Remote Similarity NPC469627
0.6933 Remote Similarity NPC472021
0.6915 Remote Similarity NPC470191
0.6907 Remote Similarity NPC477511
0.6907 Remote Similarity NPC264477
0.6882 Remote Similarity NPC474379
0.6842 Remote Similarity NPC172622
0.6837 Remote Similarity NPC471148
0.6835 Remote Similarity NPC469925
0.6818 Remote Similarity NPC128429
0.68 Remote Similarity NPC472020
0.68 Remote Similarity NPC226602
0.68 Remote Similarity NPC472019
0.6795 Remote Similarity NPC306805
0.6795 Remote Similarity NPC215987
0.6774 Remote Similarity NPC216137
0.6774 Remote Similarity NPC474699
0.6742 Remote Similarity NPC65133
0.6742 Remote Similarity NPC138647
0.6742 Remote Similarity NPC470238
0.6735 Remote Similarity NPC201718
0.6709 Remote Similarity NPC241949
0.6703 Remote Similarity NPC5130
0.67 Remote Similarity NPC477510
0.67 Remote Similarity NPC471143
0.6667 Remote Similarity NPC477264
0.6667 Remote Similarity NPC228411
0.6634 Remote Similarity NPC44004
0.6634 Remote Similarity NPC474101
0.6633 Remote Similarity NPC477512
0.6632 Remote Similarity NPC471147
0.6629 Remote Similarity NPC476721
0.6627 Remote Similarity NPC470526
0.6625 Remote Similarity NPC286842
0.6623 Remote Similarity NPC469923
0.6623 Remote Similarity NPC469922
0.66 Remote Similarity NPC474166
0.66 Remote Similarity NPC19239
0.6596 Remote Similarity NPC475881
0.6596 Remote Similarity NPC70251
0.6593 Remote Similarity NPC476717
0.6593 Remote Similarity NPC477441
0.6591 Remote Similarity NPC207188
0.6582 Remote Similarity NPC476330
0.6569 Remote Similarity NPC477513
0.6566 Remote Similarity NPC471767
0.6566 Remote Similarity NPC474339
0.6566 Remote Similarity NPC164598
0.6556 Remote Similarity NPC475689
0.6552 Remote Similarity NPC80999
0.6552 Remote Similarity NPC276647
0.6552 Remote Similarity NPC622
0.6538 Remote Similarity NPC473975
0.6538 Remote Similarity NPC473843
0.6538 Remote Similarity NPC474586
0.6538 Remote Similarity NPC473594
0.6538 Remote Similarity NPC474552
0.6531 Remote Similarity NPC208233
0.6531 Remote Similarity NPC274695
0.6526 Remote Similarity NPC475788
0.6526 Remote Similarity NPC228700
0.6517 Remote Similarity NPC212340
0.6506 Remote Similarity NPC470243
0.65 Remote Similarity NPC250594
0.6495 Remote Similarity NPC17585
0.6495 Remote Similarity NPC39859
0.6495 Remote Similarity NPC470883
0.6495 Remote Similarity NPC76862
0.6495 Remote Similarity NPC158416
0.6495 Remote Similarity NPC476275
0.6476 Remote Similarity NPC194619
0.6471 Remote Similarity NPC475802
0.6471 Remote Similarity NPC9303
0.6471 Remote Similarity NPC16313
0.6471 Remote Similarity NPC93213
0.6458 Remote Similarity NPC190294
0.6452 Remote Similarity NPC471221
0.6452 Remote Similarity NPC221993
0.6436 Remote Similarity NPC469350
0.6429 Remote Similarity NPC236176
0.6421 Remote Similarity NPC20713
0.6413 Remote Similarity NPC228593
0.6413 Remote Similarity NPC235196
0.6408 Remote Similarity NPC474421
0.6408 Remote Similarity NPC475587
0.6408 Remote Similarity NPC475510
0.6408 Remote Similarity NPC326994
0.6408 Remote Similarity NPC469558
0.6408 Remote Similarity NPC194620
0.6408 Remote Similarity NPC324327
0.6408 Remote Similarity NPC72813
0.6404 Remote Similarity NPC328639
0.6404 Remote Similarity NPC329490
0.64 Remote Similarity NPC98225
0.6392 Remote Similarity NPC475900
0.6392 Remote Similarity NPC322188
0.6389 Remote Similarity NPC287811
0.6383 Remote Similarity NPC151770
0.6364 Remote Similarity NPC474213
0.6364 Remote Similarity NPC17935
0.6364 Remote Similarity NPC475821
0.6364 Remote Similarity NPC470363
0.6353 Remote Similarity NPC215030
0.6353 Remote Similarity NPC55508
0.6346 Remote Similarity NPC474664
0.6346 Remote Similarity NPC55972
0.6346 Remote Similarity NPC473939
0.6346 Remote Similarity NPC169888
0.6346 Remote Similarity NPC473595
0.6346 Remote Similarity NPC14862
0.6346 Remote Similarity NPC327286
0.6346 Remote Similarity NPC233379
0.6344 Remote Similarity NPC266957
0.6341 Remote Similarity NPC319007
0.6327 Remote Similarity NPC476009
0.6327 Remote Similarity NPC35498
0.6327 Remote Similarity NPC31645
0.6322 Remote Similarity NPC143250
0.6322 Remote Similarity NPC214030
0.6322 Remote Similarity NPC83108
0.6316 Remote Similarity NPC477442
0.6316 Remote Similarity NPC477433
0.6316 Remote Similarity NPC477444
0.6304 Remote Similarity NPC478111
0.6289 Remote Similarity NPC476267
0.6286 Remote Similarity NPC475922
0.6286 Remote Similarity NPC15218
0.6277 Remote Similarity NPC201046
0.6277 Remote Similarity NPC476379
0.6265 Remote Similarity NPC28526
0.6264 Remote Similarity NPC475989
0.6264 Remote Similarity NPC474472
0.6264 Remote Similarity NPC257358
0.6263 Remote Similarity NPC323421
0.6263 Remote Similarity NPC328562
0.6263 Remote Similarity NPC474313
0.625 Remote Similarity NPC314103
0.6239 Remote Similarity NPC474333
0.6238 Remote Similarity NPC162024
0.6237 Remote Similarity NPC475729
0.6237 Remote Similarity NPC204048
0.6237 Remote Similarity NPC50637
0.6237 Remote Similarity NPC474215
0.6235 Remote Similarity NPC474755
0.6226 Remote Similarity NPC161816
0.6226 Remote Similarity NPC281624
0.6226 Remote Similarity NPC115257
0.6224 Remote Similarity NPC475659
0.6222 Remote Similarity NPC475743
0.6214 Remote Similarity NPC474741
0.6211 Remote Similarity NPC477443
0.6211 Remote Similarity NPC477440
0.6207 Remote Similarity NPC474020
0.6204 Remote Similarity NPC33360
0.6197 Remote Similarity NPC13105
0.6196 Remote Similarity NPC471343
0.6196 Remote Similarity NPC9060
0.6196 Remote Similarity NPC181871
0.619 Remote Similarity NPC329876
0.619 Remote Similarity NPC117604
0.6182 Remote Similarity NPC296822
0.6176 Remote Similarity NPC105725
0.6176 Remote Similarity NPC49393
0.6173 Remote Similarity NPC295256
0.617 Remote Similarity NPC314364
0.617 Remote Similarity NPC51662
0.617 Remote Similarity NPC471739
0.617 Remote Similarity NPC197333
0.617 Remote Similarity NPC231889
0.6168 Remote Similarity NPC475495
0.6164 Remote Similarity NPC314084
0.6164 Remote Similarity NPC474331
0.6163 Remote Similarity NPC477867
0.6163 Remote Similarity NPC125164
0.6162 Remote Similarity NPC473859
0.6146 Remote Similarity NPC475748
0.6146 Remote Similarity NPC469718
0.6146 Remote Similarity NPC329857
0.6145 Remote Similarity NPC119838
0.6145 Remote Similarity NPC82315
0.6139 Remote Similarity NPC475949
0.6139 Remote Similarity NPC288876
0.6129 Remote Similarity NPC474572
0.6129 Remote Similarity NPC149725
0.6129 Remote Similarity NPC477445
0.6129 Remote Similarity NPC304509
0.6129 Remote Similarity NPC474547
0.6129 Remote Similarity NPC476715
0.6129 Remote Similarity NPC51267
0.6129 Remote Similarity NPC47958
0.6122 Remote Similarity NPC473330

  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 NPC108014 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
0.64 Remote Similarity NPD1700 Approved
0.6176 Remote Similarity NPD8301 Approved
0.6176 Remote Similarity NPD8300 Approved
0.6173 Remote Similarity NPD9496 Clinical (unspecified phase)
0.6145 Remote Similarity NPD229 Approved
0.6067 Remote Similarity NPD4802 Phase 2
0.6067 Remote Similarity NPD4238 Approved
0.6058 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6058 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6044 Remote Similarity NPD1780 Approved
0.6044 Remote Similarity NPD1779 Approved
0.5972 Remote Similarity NPD6125 Clinical (unspecified phase)
0.5957 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5854 Remote Similarity NPD7909 Approved
0.5794 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5794 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5741 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5714 Remote Similarity NPD1695 Approved
0.5714 Remote Similarity NPD3730 Approved
0.5714 Remote Similarity NPD3728 Approved
0.5657 Remote Similarity NPD6698 Approved
0.5657 Remote Similarity NPD46 Approved
0.5644 Remote Similarity NPD5282 Discontinued
0.5638 Remote Similarity NPD7345 Approved
0.5636 Remote Similarity NPD5955 Clinical (unspecified phase)
0.56 Remote Similarity NPD7983 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