Structure

Physi-Chem Properties

Molecular Weight:  398.29
Volume:  447.598
LogP:  5.269
LogD:  4.357
LogS:  -4.026
# Rotatable Bonds:  16
TPSA:  54.12
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.289
Synthetic Accessibility Score:  2.922
Fsp3:  0.56
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:  -4.813
MDCK Permeability:  2.128200139850378e-05
Pgp-inhibitor:  0.823
Pgp-substrate:  0.437
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.875
30% Bioavailability (F30%):  0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.286
Plasma Protein Binding (PPB):  98.1679458618164%
Volume Distribution (VD):  0.798
Pgp-substrate:  1.248162865638733%

ADMET: Metabolism

CYP1A2-inhibitor:  0.473
CYP1A2-substrate:  0.853
CYP2C19-inhibitor:  0.74
CYP2C19-substrate:  0.126
CYP2C9-inhibitor:  0.57
CYP2C9-substrate:  0.824
CYP2D6-inhibitor:  0.869
CYP2D6-substrate:  0.869
CYP3A4-inhibitor:  0.944
CYP3A4-substrate:  0.151

ADMET: Excretion

Clearance (CL):  4.339
Half-life (T1/2):  0.78

ADMET: Toxicity

hERG Blockers:  0.565
Human Hepatotoxicity (H-HT):  0.741
Drug-inuced Liver Injury (DILI):  0.031
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.056
Maximum Recommended Daily Dose:  0.94
Skin Sensitization:  0.96
Carcinogencity:  0.085
Eye Corrosion:  0.003
Eye Irritation:  0.048
Respiratory Toxicity:  0.115

Download Data

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

  Natural Product: NPC311276

Natural Product ID:  NPC311276
Common Name*:   Hermitamide B
IUPAC Name:   (E,7S)-N-[2-(1H-indol-3-yl)ethyl]-7-methoxytetradec-4-enamide
Synonyms:  
Standard InCHIKey:  OHYDYQKPXIXRBQ-GLJAUCNMSA-N
Standard InCHI:  InChI=1S/C25H38N2O2/c1-3-4-5-6-8-13-22(29-2)14-9-7-10-17-25(28)26-19-18-21-20-27-24-16-12-11-15-23(21)24/h7,9,11-12,15-16,20,22,27H,3-6,8,10,13-14,17-19H2,1-2H3,(H,26,28)/b9-7+/t22-/m0/s1
SMILES:  CCCCCCC[C@@H](C/C=C/CCC(=NCCc1c[nH]c2ccccc12)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL524285
PubChem CID:   10386173
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0002497] Indoles
          • [CHEMONTID:0004196] 3-alkylindoles

*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
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10514329]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10654420]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10691708]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. palauan n.a. PMID[10691729]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10843570]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10924172]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10978206]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076571]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076573]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076574]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11277744]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11389621]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11430000]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11473443]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11922791]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[12762816]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[12828459]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[14575437]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[1517734]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[16643028]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17125217]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17441769]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[18444683]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Singapore n.a. PMID[19093843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19489598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. eastern Caribbean n.a. PMID[19739598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19839606]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20030365]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. panamanian n.a. PMID[20158242]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Floridian n.a. PMID[20166701]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20936843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21138309]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[2128518]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21341718]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21539315]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21806011]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21999614]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[22035372]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[29792428]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[3924698]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[7623050]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[8699186]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9584405]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599278]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599279]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9784156]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria 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
NPT3715 Individual Protein Sodium channel protein type II alpha subunit Homo sapiens Inhibition = 100.0 % PMID[472984]
NPT3715 Individual Protein Sodium channel protein type II alpha subunit Homo sapiens Inhibition = 87.8 % PMID[472984]
NPT3715 Individual Protein Sodium channel protein type II alpha subunit Homo sapiens Inhibition = 17.2 % PMID[472984]
NPT27 Others Unspecified IC50 = 5500.0 nM PMID[472983]
NPT176 Organism Artemia salina Artemia salina LD50 = 18.0 uM PMID[472983]
NPT1042 Organism Carassius auratus Carassius auratus LD50 = 25.0 uM PMID[472983]
NPT2 Others Unspecified Activity = 29.02 % PMID[472984]

☑ 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 NPC311276 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
0.96 High Similarity NPC469762
0.9533 High Similarity NPC469785
0.953 High Similarity NPC259644
0.953 High Similarity NPC469786
0.953 High Similarity NPC469765
0.953 High Similarity NPC73952
0.953 High Similarity NPC469760
0.953 High Similarity NPC25008
0.953 High Similarity NPC469763
0.9477 High Similarity NPC40779
0.9467 High Similarity NPC70922
0.9467 High Similarity NPC212376
0.9467 High Similarity NPC75540
0.9467 High Similarity NPC80597
0.9467 High Similarity NPC211572
0.9128 High Similarity NPC314372
0.9108 High Similarity NPC160105
0.9051 High Similarity NPC201700
0.9032 High Similarity NPC230869
0.9013 High Similarity NPC24678
0.9013 High Similarity NPC105818
0.8993 High Similarity NPC190296
0.8987 High Similarity NPC49954
0.8987 High Similarity NPC474561
0.8951 High Similarity NPC151939
0.8917 High Similarity NPC282231
0.8882 High Similarity NPC314603
0.8868 High Similarity NPC54988
0.8861 High Similarity NPC102423
0.8859 High Similarity NPC469761
0.8859 High Similarity NPC469779
0.8859 High Similarity NPC469780
0.8859 High Similarity NPC469783
0.8859 High Similarity NPC469767
0.8859 High Similarity NPC469768
0.8859 High Similarity NPC469784
0.8854 High Similarity NPC131718
0.8854 High Similarity NPC279918
0.8841 High Similarity NPC300688
0.8812 High Similarity NPC63751
0.88 High Similarity NPC469766
0.8765 High Similarity NPC313791
0.875 High Similarity NPC159856
0.8743 High Similarity NPC188387
0.8743 High Similarity NPC163421
0.8742 High Similarity NPC194640
0.8675 High Similarity NPC233936
0.8667 High Similarity NPC73767
0.8658 High Similarity NPC84911
0.8636 High Similarity NPC471957
0.8623 High Similarity NPC163055
0.8623 High Similarity NPC469358
0.8606 High Similarity NPC248454
0.8591 High Similarity NPC96102
0.8591 High Similarity NPC29886
0.8591 High Similarity NPC261195
0.8589 High Similarity NPC470498
0.8563 High Similarity NPC71037
0.8543 High Similarity NPC110126
0.8538 High Similarity NPC95783
0.8533 High Similarity NPC105127
0.8494 Intermediate Similarity NPC68354
0.8494 Intermediate Similarity NPC59269
0.8485 Intermediate Similarity NPC37423
0.8485 Intermediate Similarity NPC275305
0.8471 Intermediate Similarity NPC474707
0.8471 Intermediate Similarity NPC235684
0.8466 Intermediate Similarity NPC78020
0.8443 Intermediate Similarity NPC213468
0.8438 Intermediate Similarity NPC92796
0.8438 Intermediate Similarity NPC135141
0.8434 Intermediate Similarity NPC267885
0.8421 Intermediate Similarity NPC317030
0.8415 Intermediate Similarity NPC194411
0.8412 Intermediate Similarity NPC280290
0.8391 Intermediate Similarity NPC474177
0.8373 Intermediate Similarity NPC110500
0.8373 Intermediate Similarity NPC203468
0.8373 Intermediate Similarity NPC149155
0.8372 Intermediate Similarity NPC65215
0.8372 Intermediate Similarity NPC173028
0.8366 Intermediate Similarity NPC279081
0.8363 Intermediate Similarity NPC94752
0.8363 Intermediate Similarity NPC315555
0.8354 Intermediate Similarity NPC216713
0.8333 Intermediate Similarity NPC248041
0.8333 Intermediate Similarity NPC126709
0.8324 Intermediate Similarity NPC193761
0.8322 Intermediate Similarity NPC82295
0.8314 Intermediate Similarity NPC204565
0.8313 Intermediate Similarity NPC285469
0.8313 Intermediate Similarity NPC34508
0.8304 Intermediate Similarity NPC314002
0.8302 Intermediate Similarity NPC200214
0.8291 Intermediate Similarity NPC53947
0.8274 Intermediate Similarity NPC111275
0.8268 Intermediate Similarity NPC300183
0.8266 Intermediate Similarity NPC213629
0.8256 Intermediate Similarity NPC171171
0.8247 Intermediate Similarity NPC230002
0.8246 Intermediate Similarity NPC204717
0.8239 Intermediate Similarity NPC133366
0.8225 Intermediate Similarity NPC283219
0.8225 Intermediate Similarity NPC55772
0.8225 Intermediate Similarity NPC176199
0.8225 Intermediate Similarity NPC215795
0.8222 Intermediate Similarity NPC476874
0.8217 Intermediate Similarity NPC288838
0.8202 Intermediate Similarity NPC470499
0.8198 Intermediate Similarity NPC15102
0.8187 Intermediate Similarity NPC220765
0.8187 Intermediate Similarity NPC48938
0.8182 Intermediate Similarity NPC307963
0.8182 Intermediate Similarity NPC267343
0.8177 Intermediate Similarity NPC98715
0.8167 Intermediate Similarity NPC475506
0.8166 Intermediate Similarity NPC14113
0.8166 Intermediate Similarity NPC145885
0.8166 Intermediate Similarity NPC84827
0.8155 Intermediate Similarity NPC189812
0.8155 Intermediate Similarity NPC329688
0.8148 Intermediate Similarity NPC129721
0.814 Intermediate Similarity NPC228835
0.8137 Intermediate Similarity NPC470507
0.8136 Intermediate Similarity NPC157828
0.8136 Intermediate Similarity NPC195239
0.8133 Intermediate Similarity NPC317430
0.8125 Intermediate Similarity NPC99666
0.8122 Intermediate Similarity NPC155143
0.8118 Intermediate Similarity NPC270009
0.8114 Intermediate Similarity NPC154339
0.8113 Intermediate Similarity NPC321911
0.8113 Intermediate Similarity NPC37548
0.811 Intermediate Similarity NPC16667
0.8103 Intermediate Similarity NPC46580
0.8101 Intermediate Similarity NPC143872
0.8101 Intermediate Similarity NPC473640
0.809 Intermediate Similarity NPC11445
0.809 Intermediate Similarity NPC251090
0.8081 Intermediate Similarity NPC472108
0.8081 Intermediate Similarity NPC139291
0.8072 Intermediate Similarity NPC49217
0.8061 Intermediate Similarity NPC78375
0.8061 Intermediate Similarity NPC469813
0.8061 Intermediate Similarity NPC476446
0.8057 Intermediate Similarity NPC321708
0.8056 Intermediate Similarity NPC100321
0.805 Intermediate Similarity NPC469811
0.805 Intermediate Similarity NPC201380
0.805 Intermediate Similarity NPC179787
0.8047 Intermediate Similarity NPC472586
0.8045 Intermediate Similarity NPC227582
0.8043 Intermediate Similarity NPC46225
0.8043 Intermediate Similarity NPC225821
0.8037 Intermediate Similarity NPC286427
0.8035 Intermediate Similarity NPC165495
0.8035 Intermediate Similarity NPC284678
0.8025 Intermediate Similarity NPC207726
0.8025 Intermediate Similarity NPC471458
0.8024 Intermediate Similarity NPC154293
0.8023 Intermediate Similarity NPC192270
0.8012 Intermediate Similarity NPC470823
0.8012 Intermediate Similarity NPC141377
0.8012 Intermediate Similarity NPC470508
0.8012 Intermediate Similarity NPC11126
0.8011 Intermediate Similarity NPC470497
0.8011 Intermediate Similarity NPC76748
0.8 Intermediate Similarity NPC127677
0.8 Intermediate Similarity NPC314957
0.8 Intermediate Similarity NPC258062
0.7989 Intermediate Similarity NPC62510
0.7988 Intermediate Similarity NPC472123
0.7988 Intermediate Similarity NPC56765
0.7988 Intermediate Similarity NPC206819
0.7988 Intermediate Similarity NPC41257
0.7988 Intermediate Similarity NPC67056
0.7988 Intermediate Similarity NPC318065
0.7987 Intermediate Similarity NPC63545
0.7977 Intermediate Similarity NPC19679
0.7977 Intermediate Similarity NPC472109
0.7977 Intermediate Similarity NPC472444
0.7977 Intermediate Similarity NPC472110
0.7976 Intermediate Similarity NPC280548
0.7975 Intermediate Similarity NPC242556
0.7975 Intermediate Similarity NPC141353
0.7966 Intermediate Similarity NPC92111
0.7963 Intermediate Similarity NPC325903
0.7963 Intermediate Similarity NPC141926
0.7957 Intermediate Similarity NPC478158
0.7955 Intermediate Similarity NPC296527
0.7955 Intermediate Similarity NPC46413
0.7953 Intermediate Similarity NPC184964
0.7953 Intermediate Similarity NPC293472
0.7946 Intermediate Similarity NPC323927
0.7944 Intermediate Similarity NPC229332
0.7935 Intermediate Similarity NPC150259
0.7927 Intermediate Similarity NPC216643
0.7921 Intermediate Similarity NPC324149
0.7921 Intermediate Similarity NPC47190
0.7921 Intermediate Similarity NPC473342

  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 NPC311276 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
0.8875 High Similarity NPD4184 Clinical (unspecified phase)
0.8834 High Similarity NPD2144 Approved
0.8675 High Similarity NPD3038 Discontinued
0.8667 High Similarity NPD786 Approved
0.8614 High Similarity NPD6595 Phase 3
0.8598 High Similarity NPD5065 Approved
0.8591 High Similarity NPD198 Clinical (unspecified phase)
0.8554 High Similarity NPD4079 Approved
0.8554 High Similarity NPD4076 Approved
0.8494 Intermediate Similarity NPD3505 Approved
0.8494 Intermediate Similarity NPD3506 Approved
0.8466 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.8431 Intermediate Similarity NPD1722 Approved
0.8402 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD482 Approved
0.8344 Intermediate Similarity NPD3100 Discontinued
0.8314 Intermediate Similarity NPD8431 Approved
0.8294 Intermediate Similarity NPD2095 Phase 2
0.8294 Intermediate Similarity NPD2094 Phase 2
0.8294 Intermediate Similarity NPD2092 Phase 2
0.8291 Intermediate Similarity NPD2172 Phase 1
0.8266 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.8246 Intermediate Similarity NPD2096 Phase 2
0.8246 Intermediate Similarity NPD2091 Phase 2
0.8228 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.8198 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD1038 Approved
0.8176 Intermediate Similarity NPD4462 Approved
0.8176 Intermediate Similarity NPD4463 Approved
0.8166 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD750 Phase 2
0.8087 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.8087 Intermediate Similarity NPD7957 Phase 1
0.805 Intermediate Similarity NPD4703 Approved
0.805 Intermediate Similarity NPD4702 Approved
0.8049 Intermediate Similarity NPD1404 Approved
0.8049 Intermediate Similarity NPD1403 Approved
0.8045 Intermediate Similarity NPD7948 Phase 1
0.8024 Intermediate Similarity NPD4639 Approved
0.8024 Intermediate Similarity NPD4640 Approved
0.8024 Intermediate Similarity NPD4638 Approved
0.8 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7978 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7978 Intermediate Similarity NPD8072 Approved
0.7976 Intermediate Similarity NPD1325 Approved
0.7976 Intermediate Similarity NPD1326 Approved
0.7964 Intermediate Similarity NPD2639 Approved
0.7964 Intermediate Similarity NPD2642 Approved
0.7963 Intermediate Similarity NPD2837 Discontinued
0.7962 Intermediate Similarity NPD1592 Phase 3
0.7941 Intermediate Similarity NPD4128 Approved
0.7923 Intermediate Similarity NPD8073 Approved
0.7917 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD2640 Approved
0.7917 Intermediate Similarity NPD2641 Approved
0.7877 Intermediate Similarity NPD802 Phase 2
0.7877 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD4181 Approved
0.7844 Intermediate Similarity NPD3323 Discontinued
0.7844 Intermediate Similarity NPD5140 Approved
0.7844 Intermediate Similarity NPD5138 Approved
0.7838 Intermediate Similarity NPD8272 Phase 2
0.7824 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD8036 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD8037 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD3717 Discontinued
0.7798 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7797 Intermediate Similarity NPD5590 Clinical (unspecified phase)
0.7796 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD4075 Phase 2
0.7791 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD5067 Phase 2
0.7778 Intermediate Similarity NPD5066 Phase 2
0.7778 Intermediate Similarity NPD7470 Discontinued
0.7771 Intermediate Similarity NPD5596 Phase 2
0.7759 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7749 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD8122 Approved
0.7746 Intermediate Similarity NPD8123 Approved
0.7725 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD2510 Approved
0.7713 Intermediate Similarity NPD2509 Approved
0.7706 Intermediate Similarity NPD5021 Discontinued
0.7706 Intermediate Similarity NPD5862 Discovery
0.7701 Intermediate Similarity NPD8386 Phase 2
0.7697 Intermediate Similarity NPD3961 Discontinued
0.7697 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7663 Intermediate Similarity NPD3825 Phase 3
0.766 Intermediate Similarity NPD1392 Approved
0.764 Intermediate Similarity NPD5254 Discontinued
0.7637 Intermediate Similarity NPD7944 Discontinued
0.7637 Intermediate Similarity NPD7619 Phase 3
0.7637 Intermediate Similarity NPD7618 Phase 3
0.763 Intermediate Similarity NPD2928 Phase 2
0.7627 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD3404 Approved
0.7622 Intermediate Similarity NPD484 Approved
0.7616 Intermediate Similarity NPD3610 Approved
0.7616 Intermediate Similarity NPD3609 Approved
0.7611 Intermediate Similarity NPD6281 Approved
0.7607 Intermediate Similarity NPD1661 Suspended
0.7605 Intermediate Similarity NPD2581 Approved
0.7605 Intermediate Similarity NPD2582 Approved
0.7602 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD3654 Approved
0.7594 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD2380 Approved
0.7586 Intermediate Similarity NPD2381 Approved
0.7586 Intermediate Similarity NPD2382 Approved
0.7579 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD972 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD1853 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD5255 Approved
0.7553 Intermediate Similarity NPD5426 Phase 3
0.7553 Intermediate Similarity NPD5901 Discontinued
0.7552 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD3476 Approved
0.7548 Intermediate Similarity NPD3475 Approved
0.753 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD8129 Discovery
0.7528 Intermediate Similarity NPD4957 Phase 2
0.7526 Intermediate Similarity NPD5612 Discontinued
0.7515 Intermediate Similarity NPD3833 Phase 3
0.7515 Intermediate Similarity NPD3835 Phase 3
0.7514 Intermediate Similarity NPD3116 Approved
0.7514 Intermediate Similarity NPD3117 Approved
0.75 Intermediate Similarity NPD4547 Phase 3
0.75 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7472 Intermediate Similarity NPD5105 Approved
0.7472 Intermediate Similarity NPD5106 Approved
0.7471 Intermediate Similarity NPD8026 Phase 1
0.7469 Intermediate Similarity NPD2006 Phase 2
0.7468 Intermediate Similarity NPD2118 Approved
0.7468 Intermediate Similarity NPD2119 Approved
0.7468 Intermediate Similarity NPD991 Phase 2
0.7468 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.7461 Intermediate Similarity NPD3330 Phase 1
0.7461 Intermediate Similarity NPD8093 Discontinued
0.7459 Intermediate Similarity NPD6664 Approved
0.7458 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD2430 Phase 2
0.7448 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD6217 Discontinued
0.744 Intermediate Similarity NPD6026 Approved
0.744 Intermediate Similarity NPD2580 Discontinued
0.7439 Intermediate Similarity NPD6148 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD2189 Approved
0.7435 Intermediate Similarity NPD2187 Approved
0.7433 Intermediate Similarity NPD4601 Approved
0.7433 Intermediate Similarity NPD4600 Approved
0.7423 Intermediate Similarity NPD8094 Discontinued
0.7405 Intermediate Similarity NPD3385 Approved
0.7403 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD2844 Phase 3
0.7398 Intermediate Similarity NPD8406 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD4670 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD4671 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD4669 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD5100 Phase 3
0.7382 Intermediate Similarity NPD8410 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD4699 Discontinued
0.7377 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD8458 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD4112 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD2385 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD6158 Phase 2
0.7365 Intermediate Similarity NPD2882 Phase 1
0.7363 Intermediate Similarity NPD7233 Approved
0.7363 Intermediate Similarity NPD7234 Approved
0.7362 Intermediate Similarity NPD2007 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD1554 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD3393 Approved
0.7347 Intermediate Similarity NPD3394 Approved
0.7347 Intermediate Similarity NPD3389 Approved
0.734 Intermediate Similarity NPD8248 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD4615 Phase 2
0.7333 Intermediate Similarity NPD6178 Phase 3
0.7333 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1683 Approved
0.7333 Intermediate Similarity NPD8488 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD3003 Approved
0.733 Intermediate Similarity NPD7001 Phase 3
0.7329 Intermediate Similarity NPD2896 Discontinued
0.7322 Intermediate Similarity NPD4499 Approved
0.7318 Intermediate Similarity NPD3178 Discontinued
0.731 Intermediate Similarity NPD2511 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