Structure

Physi-Chem Properties

Molecular Weight:  246.13
Volume:  258.152
LogP:  2.48
LogD:  1.983
LogS:  -2.743
# Rotatable Bonds:  0
TPSA:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.374
Synthetic Accessibility Score:  4.67
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.605
MDCK Permeability:  2.3815262466087006e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.022
20% Bioavailability (F20%):  0.348
30% Bioavailability (F30%):  0.115

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.095
Plasma Protein Binding (PPB):  81.37567901611328%
Volume Distribution (VD):  1.426
Pgp-substrate:  21.565553665161133%

ADMET: Metabolism

CYP1A2-inhibitor:  0.101
CYP1A2-substrate:  0.358
CYP2C19-inhibitor:  0.125
CYP2C19-substrate:  0.807
CYP2C9-inhibitor:  0.17
CYP2C9-substrate:  0.159
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.06
CYP3A4-inhibitor:  0.783
CYP3A4-substrate:  0.482

ADMET: Excretion

Clearance (CL):  13.814
Half-life (T1/2):  0.642

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.122
Drug-inuced Liver Injury (DILI):  0.208
AMES Toxicity:  0.073
Rat Oral Acute Toxicity:  0.687
Maximum Recommended Daily Dose:  0.913
Skin Sensitization:  0.307
Carcinogencity:  0.907
Eye Corrosion:  0.85
Eye Irritation:  0.702
Respiratory Toxicity:  0.968

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

  Natural Product: NPC161957

Natural Product ID:  NPC161957
Common Name*:   Aromaticin
IUPAC Name:   (3aS,5R,5aR,8aS,9aR)-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
Synonyms:   Aromaticin
Standard InCHIKey:  OSSDUQKWVVZIGP-SCGWIAOYSA-N
Standard InCHI:  InChI=1S/C15H18O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h4-5,8,10-12H,2,6-7H2,1,3H3/t8-,10-,11+,12+,15+/m1/s1
SMILES:  C[C@@H]1C[C@H]2[C@H](C[C@@]3(C)[C@H]1C=CC3=O)C(=C)C(=O)O2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL494255
PubChem CID:   282529
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0002046] Ambrosanolides and secoambrosanolides

*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
NPO33469 Asteraceae Family Asteraceae Eukaryota n.a. n.a. n.a. PMID[18329753]
NPO4280 Inula hupehensis Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[21894898]
NPO4280 Inula hupehensis Species Asteraceae Eukaryota aerial parts n.a. n.a. PMID[21894898]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8509 Senecio discolor Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16482 Hypoestes forskalei Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18577 Lathyrus roseus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10732 Erysimum allionii Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18249 Eucalyptus deglupta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28309 Artocarpus nitidus Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19131 Callilepis salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15631 Baccharis neaei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11615 Kopsia deverrei Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15114 Oxalis pes-caprae Species Oxalidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17192 Licaria macrophylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16848 Nasutitermes nigriceps Species Termitoidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9681 Toxicodendron diversilobum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4280 Inula hupehensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17502 Senecio jacquemontianus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21499 Halimeda tuna Species Halimedaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26490 Helenium aromaticum 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
NPT91 Cell Line KB Homo sapiens pED50 = 5.86 n.a. PMID[523578]
NPT91 Cell Line KB Homo sapiens ED50 = 0.34 ug ml-1 PMID[523578]
NPT91 Cell Line KB Homo sapiens ED50 = 1.38 umol/L PMID[523579]
NPT91 Cell Line KB Homo sapiens ED50 = 2.0 ug ml-1 PMID[523580]
NPT3728 Individual Protein p53-binding protein Mdm-2 Homo sapiens EC50 = 590.0 nM PMID[523581]
NPT1197 Individual Protein Huntingtin Homo sapiens Potency = 5623.4 nM PMID[523581]
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency = 2511.9 nM PMID[523581]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 17782.8 nM PMID[523581]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 10000.0 nM PMID[523581]
NPT3 Individual Protein Thioredoxin glutathione reductase Schistosoma mansoni Potency = 35481.3 nM PMID[523581]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 14125.4 nM PMID[523581]
NPT538 Individual Protein Niemann-Pick C1 protein Homo sapiens Potency = 3548.1 nM PMID[523581]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 6309.6 nM PMID[523581]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 20596.2 nM PMID[523581]
NPT2892 Individual Protein X-box-binding protein 1 Homo sapiens IC50 = 5710.0 nM PMID[523581]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 3661.1 nM PMID[523581]
NPT2893 Individual Protein DNA damage-inducible transcript 3 protein Mus musculus IC50 = 10000.0 nM PMID[523581]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 32629.4 nM PMID[523581]
NPT1397 Cell Line INS1 Rattus norvegicus AC50 = 7821.0 nM PMID[523581]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 7943.3 nM PMID[523581]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 4466.8 nM PMID[523581]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 8200.0 nM PMID[523582]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2909.3 nM PMID[523581]
NPT477 Individual Protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens Potency n.a. 3162.3 nM PMID[523581]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 1458.1 nM PMID[523581]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 7943.3 nM PMID[523581]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 10000.0 nM PMID[523581]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 651.3 nM PMID[523581]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 1032.3 nM PMID[523581]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 35481.3 nM PMID[523581]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 70794.6 nM PMID[523581]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Potency = 11220.2 nM PMID[523581]
NPT536 Uncleic Acid microRNA 21 Homo sapiens Potency = 4645.1 nM PMID[523581]
NPT2 Others Unspecified Potency = 18356.4 nM PMID[523581]
NPT2 Others Unspecified Potency n.a. 18356.4 nM PMID[523581]
NPT2 Others Unspecified Potency n.a. 1584.9 nM PMID[523581]
NPT2 Others Unspecified IC50 = 5840.0 nM PMID[523581]
NPT2 Others Unspecified IC50 > 80000.0 nM PMID[523581]
NPT2 Others Unspecified IC50 = 1260.0 nM PMID[523581]
NPT2 Others Unspecified IC50 = 1250.0 nM PMID[523581]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 8275.3 nM PMID[523581]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 17782.8 nM PMID[523581]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[523581]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 5221.3 nM PMID[523581]
NPT2 Others Unspecified Potency n.a. 1995.3 nM PMID[523581]
NPT2 Others Unspecified Potency n.a. 22.4 nM PMID[523581]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[523581]
NPT2 Others Unspecified Potency n.a. 8199.5 nM PMID[523581]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 12995.3 nM PMID[523581]
NPT2 Others Unspecified Potency n.a. 2238.7 nM PMID[523581]
NPT2 Others Unspecified Potency n.a. 25118.9 nM PMID[523581]

☑ 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 NPC161957 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
0.9747 High Similarity NPC39588
0.9506 High Similarity NPC21471
0.9506 High Similarity NPC33570
0.9294 High Similarity NPC70595
0.9294 High Similarity NPC150978
0.9294 High Similarity NPC123177
0.9294 High Similarity NPC74103
0.9176 High Similarity NPC253144
0.9125 High Similarity NPC69271
0.9125 High Similarity NPC74673
0.907 High Similarity NPC284185
0.9024 High Similarity NPC215294
0.9012 High Similarity NPC10276
0.9012 High Similarity NPC35089
0.8977 High Similarity NPC48803
0.8977 High Similarity NPC90121
0.8977 High Similarity NPC275960
0.8977 High Similarity NPC193645
0.8889 High Similarity NPC302426
0.8889 High Similarity NPC293418
0.8889 High Similarity NPC290508
0.8889 High Similarity NPC73052
0.8889 High Similarity NPC276356
0.8778 High Similarity NPC169205
0.8706 High Similarity NPC70422
0.8706 High Similarity NPC104961
0.8706 High Similarity NPC70555
0.8681 High Similarity NPC141191
0.8681 High Similarity NPC54843
0.8667 High Similarity NPC185553
0.8659 High Similarity NPC223904
0.8652 High Similarity NPC167219
0.8571 High Similarity NPC54468
0.8537 High Similarity NPC472965
0.8537 High Similarity NPC264227
0.8537 High Similarity NPC63649
0.8537 High Similarity NPC182550
0.8523 High Similarity NPC62815
0.8519 High Similarity NPC208223
0.8519 High Similarity NPC15975
0.8519 High Similarity NPC65603
0.8519 High Similarity NPC195785
0.85 High Similarity NPC193351
0.85 High Similarity NPC138408
0.85 High Similarity NPC226669
0.8488 Intermediate Similarity NPC107787
0.8471 Intermediate Similarity NPC115786
0.8434 Intermediate Similarity NPC6823
0.8427 Intermediate Similarity NPC300312
0.8427 Intermediate Similarity NPC261607
0.8427 Intermediate Similarity NPC111114
0.8415 Intermediate Similarity NPC472960
0.8409 Intermediate Similarity NPC52198
0.8409 Intermediate Similarity NPC117405
0.8372 Intermediate Similarity NPC78089
0.8372 Intermediate Similarity NPC110405
0.8333 Intermediate Similarity NPC135776
0.8315 Intermediate Similarity NPC152467
0.8313 Intermediate Similarity NPC469690
0.8295 Intermediate Similarity NPC215831
0.8293 Intermediate Similarity NPC122264
0.8293 Intermediate Similarity NPC476794
0.8293 Intermediate Similarity NPC470240
0.8276 Intermediate Similarity NPC238593
0.8272 Intermediate Similarity NPC155587
0.825 Intermediate Similarity NPC472956
0.8235 Intermediate Similarity NPC173609
0.8229 Intermediate Similarity NPC203659
0.8211 Intermediate Similarity NPC225353
0.8202 Intermediate Similarity NPC268298
0.8202 Intermediate Similarity NPC73995
0.8193 Intermediate Similarity NPC299235
0.8171 Intermediate Similarity NPC266159
0.8171 Intermediate Similarity NPC235906
0.8171 Intermediate Similarity NPC472967
0.8171 Intermediate Similarity NPC472959
0.8161 Intermediate Similarity NPC177932
0.8148 Intermediate Similarity NPC143979
0.8148 Intermediate Similarity NPC320537
0.8125 Intermediate Similarity NPC110989
0.8118 Intermediate Similarity NPC47635
0.8118 Intermediate Similarity NPC301477
0.8118 Intermediate Similarity NPC281949
0.8118 Intermediate Similarity NPC25684
0.8118 Intermediate Similarity NPC255580
0.8118 Intermediate Similarity NPC39411
0.8111 Intermediate Similarity NPC129419
0.8095 Intermediate Similarity NPC470244
0.8095 Intermediate Similarity NPC469620
0.8095 Intermediate Similarity NPC470239
0.809 Intermediate Similarity NPC91248
0.8072 Intermediate Similarity NPC41780
0.8072 Intermediate Similarity NPC187568
0.8068 Intermediate Similarity NPC284902
0.8043 Intermediate Similarity NPC289004
0.8023 Intermediate Similarity NPC178676
0.8 Intermediate Similarity NPC32922
0.8 Intermediate Similarity NPC168679
0.8 Intermediate Similarity NPC4986
0.8 Intermediate Similarity NPC12872
0.7978 Intermediate Similarity NPC475703
0.7978 Intermediate Similarity NPC237540
0.7976 Intermediate Similarity NPC128276
0.7957 Intermediate Similarity NPC304886
0.7952 Intermediate Similarity NPC123360
0.7931 Intermediate Similarity NPC22611
0.7931 Intermediate Similarity NPC272814
0.7931 Intermediate Similarity NPC193198
0.7927 Intermediate Similarity NPC476355
0.7927 Intermediate Similarity NPC469641
0.7927 Intermediate Similarity NPC469643
0.7907 Intermediate Similarity NPC471325
0.7907 Intermediate Similarity NPC42470
0.7907 Intermediate Similarity NPC38642
0.7901 Intermediate Similarity NPC163003
0.7889 Intermediate Similarity NPC226863
0.7882 Intermediate Similarity NPC178277
0.7882 Intermediate Similarity NPC617
0.7875 Intermediate Similarity NPC296522
0.7875 Intermediate Similarity NPC144511
0.7865 Intermediate Similarity NPC309757
0.7865 Intermediate Similarity NPC64153
0.7865 Intermediate Similarity NPC236692
0.7857 Intermediate Similarity NPC57744
0.7849 Intermediate Similarity NPC477131
0.7841 Intermediate Similarity NPC156485
0.7841 Intermediate Similarity NPC475100
0.7841 Intermediate Similarity NPC165287
0.7841 Intermediate Similarity NPC238197
0.7826 Intermediate Similarity NPC131209
0.7826 Intermediate Similarity NPC290651
0.7826 Intermediate Similarity NPC133698
0.7826 Intermediate Similarity NPC191339
0.7826 Intermediate Similarity NPC221282
0.7826 Intermediate Similarity NPC286341
0.7805 Intermediate Similarity NPC58956
0.7805 Intermediate Similarity NPC269206
0.7805 Intermediate Similarity NPC295633
0.7802 Intermediate Similarity NPC295312
0.7791 Intermediate Similarity NPC47747
0.7789 Intermediate Similarity NPC108475
0.7789 Intermediate Similarity NPC170143
0.7789 Intermediate Similarity NPC474343
0.7789 Intermediate Similarity NPC213947
0.7778 Intermediate Similarity NPC478144
0.7778 Intermediate Similarity NPC118601
0.7778 Intermediate Similarity NPC201658
0.7778 Intermediate Similarity NPC472955
0.7766 Intermediate Similarity NPC474490
0.7765 Intermediate Similarity NPC471220
0.7753 Intermediate Similarity NPC215364
0.7753 Intermediate Similarity NPC165162
0.7753 Intermediate Similarity NPC235792
0.7742 Intermediate Similarity NPC200237
0.7742 Intermediate Similarity NPC475657
0.7742 Intermediate Similarity NPC153590
0.7732 Intermediate Similarity NPC171759
0.7732 Intermediate Similarity NPC474742
0.7727 Intermediate Similarity NPC318468
0.7717 Intermediate Similarity NPC469372
0.7717 Intermediate Similarity NPC106510
0.7717 Intermediate Similarity NPC312042
0.7717 Intermediate Similarity NPC71533
0.7711 Intermediate Similarity NPC140287
0.7701 Intermediate Similarity NPC325031
0.7701 Intermediate Similarity NPC141810
0.7701 Intermediate Similarity NPC475665
0.7692 Intermediate Similarity NPC469653
0.7692 Intermediate Similarity NPC469631
0.7692 Intermediate Similarity NPC471047
0.7692 Intermediate Similarity NPC475906
0.7692 Intermediate Similarity NPC469628
0.7692 Intermediate Similarity NPC178875
0.7683 Intermediate Similarity NPC129665
0.7677 Intermediate Similarity NPC189616
0.7674 Intermediate Similarity NPC270126
0.7667 Intermediate Similarity NPC67493
0.7667 Intermediate Similarity NPC220478
0.7667 Intermediate Similarity NPC469676
0.7667 Intermediate Similarity NPC56593
0.766 Intermediate Similarity NPC148463
0.766 Intermediate Similarity NPC198853
0.766 Intermediate Similarity NPC477130
0.766 Intermediate Similarity NPC477129
0.766 Intermediate Similarity NPC470010
0.766 Intermediate Similarity NPC470013
0.766 Intermediate Similarity NPC323008
0.766 Intermediate Similarity NPC262133
0.7654 Intermediate Similarity NPC5714
0.7654 Intermediate Similarity NPC199557
0.7653 Intermediate Similarity NPC474747
0.7647 Intermediate Similarity NPC53581
0.7647 Intermediate Similarity NPC103987
0.764 Intermediate Similarity NPC472958
0.764 Intermediate Similarity NPC472957
0.764 Intermediate Similarity NPC149869
0.7634 Intermediate Similarity NPC219874
0.7634 Intermediate Similarity NPC472953
0.7619 Intermediate Similarity NPC244166
0.7614 Intermediate Similarity NPC246076

  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 NPC161957 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
0.8977 High Similarity NPD1698 Clinical (unspecified phase)
0.8161 Intermediate Similarity NPD1694 Approved
0.8 Intermediate Similarity NPD1695 Approved
0.7556 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD5209 Approved
0.734 Intermediate Similarity NPD5785 Approved
0.7019 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6371 Approved
0.6947 Remote Similarity NPD6903 Approved
0.6939 Remote Similarity NPD5282 Discontinued
0.6915 Remote Similarity NPD6409 Approved
0.6915 Remote Similarity NPD7334 Approved
0.6915 Remote Similarity NPD5330 Approved
0.6915 Remote Similarity NPD6684 Approved
0.6915 Remote Similarity NPD7146 Approved
0.6915 Remote Similarity NPD7521 Approved
0.6842 Remote Similarity NPD3573 Approved
0.6818 Remote Similarity NPD8039 Approved
0.6809 Remote Similarity NPD5363 Approved
0.6804 Remote Similarity NPD5207 Approved
0.6774 Remote Similarity NPD5362 Discontinued
0.6771 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6762 Remote Similarity NPD6008 Approved
0.6737 Remote Similarity NPD5786 Approved
0.6667 Remote Similarity NPD6435 Approved
0.6667 Remote Similarity NPD4225 Approved
0.6598 Remote Similarity NPD6672 Approved
0.6598 Remote Similarity NPD5737 Approved
0.6596 Remote Similarity NPD7154 Phase 3
0.6593 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6566 Remote Similarity NPD6411 Approved
0.6566 Remote Similarity NPD5693 Phase 1
0.6559 Remote Similarity NPD5369 Approved
0.6548 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6535 Remote Similarity NPD6356 Clinical (unspecified phase)
0.65 Remote Similarity NPD6399 Phase 3
0.6489 Remote Similarity NPD4270 Approved
0.6489 Remote Similarity NPD4269 Approved
0.6452 Remote Similarity NPD5368 Approved
0.6436 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6436 Remote Similarity NPD7900 Approved
0.6436 Remote Similarity NPD6001 Approved
0.64 Remote Similarity NPD6079 Approved
0.6389 Remote Similarity NPD5697 Approved
0.6364 Remote Similarity NPD6101 Approved
0.6364 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5779 Approved
0.6337 Remote Similarity NPD5778 Approved
0.633 Remote Similarity NPD6899 Approved
0.633 Remote Similarity NPD6881 Approved
0.633 Remote Similarity NPD6011 Approved
0.6316 Remote Similarity NPD7115 Discovery
0.6306 Remote Similarity NPD6650 Approved
0.6306 Remote Similarity NPD6649 Approved
0.63 Remote Similarity NPD46 Approved
0.63 Remote Similarity NPD6698 Approved
0.6289 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6277 Remote Similarity NPD4252 Approved
0.6275 Remote Similarity NPD7748 Approved
0.6273 Remote Similarity NPD6014 Approved
0.6273 Remote Similarity NPD6012 Approved
0.6273 Remote Similarity NPD6013 Approved
0.6263 Remote Similarity NPD5208 Approved
0.625 Remote Similarity NPD7902 Approved
0.625 Remote Similarity NPD6053 Discontinued
0.6238 Remote Similarity NPD5694 Approved
0.6224 Remote Similarity NPD3618 Phase 1
0.6216 Remote Similarity NPD7290 Approved
0.6216 Remote Similarity NPD6883 Approved
0.6216 Remote Similarity NPD7102 Approved
0.6214 Remote Similarity NPD5695 Phase 3
0.62 Remote Similarity NPD6080 Approved
0.62 Remote Similarity NPD6673 Approved
0.62 Remote Similarity NPD6904 Approved
0.62 Remote Similarity NPD5328 Approved
0.619 Remote Similarity NPD5696 Approved
0.619 Remote Similarity NPD7638 Approved
0.6186 Remote Similarity NPD3665 Phase 1
0.6186 Remote Similarity NPD3133 Approved
0.6186 Remote Similarity NPD3666 Approved
0.6182 Remote Similarity NPD6686 Approved
0.6182 Remote Similarity NPD7320 Approved
0.6161 Remote Similarity NPD6617 Approved
0.6161 Remote Similarity NPD8130 Phase 1
0.6161 Remote Similarity NPD6869 Approved
0.6161 Remote Similarity NPD6847 Approved
0.6154 Remote Similarity NPD5222 Approved
0.6154 Remote Similarity NPD5221 Approved
0.6154 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6147 Remote Similarity NPD6675 Approved
0.6147 Remote Similarity NPD5739 Approved
0.6147 Remote Similarity NPD7128 Approved
0.6147 Remote Similarity NPD6402 Approved
0.6146 Remote Similarity NPD3667 Approved
0.6139 Remote Similarity NPD7838 Discovery
0.6139 Remote Similarity NPD5692 Phase 3
0.6132 Remote Similarity NPD7640 Approved
0.6132 Remote Similarity NPD7639 Approved
0.6126 Remote Similarity NPD6373 Approved
0.6126 Remote Similarity NPD6372 Approved
0.6106 Remote Similarity NPD6882 Approved
0.6106 Remote Similarity NPD8297 Approved
0.6105 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6105 Remote Similarity NPD4695 Discontinued
0.6102 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6095 Remote Similarity NPD6084 Phase 2
0.6095 Remote Similarity NPD5173 Approved
0.6095 Remote Similarity NPD6083 Phase 2
0.6092 Remote Similarity NPD7331 Phase 2
0.6091 Remote Similarity NPD5701 Approved
0.6082 Remote Similarity NPD5332 Approved
0.6082 Remote Similarity NPD5331 Approved
0.6078 Remote Similarity NPD5284 Approved
0.6078 Remote Similarity NPD5281 Approved
0.6078 Remote Similarity NPD7983 Approved
0.6078 Remote Similarity NPD6050 Approved
0.6078 Remote Similarity NPD7515 Phase 2
0.6061 Remote Similarity NPD5279 Phase 3
0.6061 Remote Similarity NPD4249 Approved
0.6061 Remote Similarity NPD4519 Discontinued
0.6061 Remote Similarity NPD4623 Approved
0.6061 Remote Similarity NPD6098 Approved
0.6042 Remote Similarity NPD4790 Discontinued
0.602 Remote Similarity NPD3668 Phase 3
0.602 Remote Similarity NPD4786 Approved
0.6019 Remote Similarity NPD5211 Phase 2
0.6018 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6 Remote Similarity NPD4697 Phase 3
0.6 Remote Similarity NPD4250 Approved
0.6 Remote Similarity NPD4251 Approved
0.5981 Remote Similarity NPD5285 Approved
0.5981 Remote Similarity NPD5286 Approved
0.5981 Remote Similarity NPD4696 Approved
0.5977 Remote Similarity NPD7341 Phase 2
0.5963 Remote Similarity NPD6052 Approved
0.596 Remote Similarity NPD1696 Phase 3
0.5948 Remote Similarity NPD6868 Approved
0.5938 Remote Similarity NPD4819 Approved
0.5938 Remote Similarity NPD4821 Approved
0.5938 Remote Similarity NPD4820 Approved
0.5938 Remote Similarity NPD4822 Approved
0.5926 Remote Similarity NPD5223 Approved
0.592 Remote Similarity NPD7260 Phase 2
0.5913 Remote Similarity NPD4632 Approved
0.5909 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5909 Remote Similarity NPD5141 Approved
0.5905 Remote Similarity NPD5210 Approved
0.5905 Remote Similarity NPD4629 Approved
0.59 Remote Similarity NPD5690 Phase 2
0.59 Remote Similarity NPD6422 Discontinued
0.5897 Remote Similarity NPD6317 Approved
0.5895 Remote Similarity NPD4271 Approved
0.5895 Remote Similarity NPD4268 Approved
0.5888 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5882 Remote Similarity NPD6051 Approved
0.5877 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5876 Remote Similarity NPD857 Phase 3
0.5872 Remote Similarity NPD5225 Approved
0.5872 Remote Similarity NPD4633 Approved
0.5872 Remote Similarity NPD5226 Approved
0.5872 Remote Similarity NPD5224 Approved
0.5862 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5859 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5849 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5849 Remote Similarity NPD7839 Suspended
0.5849 Remote Similarity NPD7732 Phase 3
0.5847 Remote Similarity NPD6335 Approved
0.5847 Remote Similarity NPD6313 Approved
0.5847 Remote Similarity NPD6314 Approved
0.5824 Remote Similarity NPD4691 Approved
0.582 Remote Similarity NPD7492 Approved
0.5818 Remote Similarity NPD5174 Approved
0.5818 Remote Similarity NPD5175 Approved
0.5816 Remote Similarity NPD4221 Approved
0.5816 Remote Similarity NPD4223 Phase 3
0.5816 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5812 Remote Similarity NPD6274 Approved
0.5806 Remote Similarity NPD4058 Approved
0.5804 Remote Similarity NPD6614 Approved
0.5804 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5798 Remote Similarity NPD7101 Approved
0.5798 Remote Similarity NPD7100 Approved
0.5794 Remote Similarity NPD4755 Approved
0.5789 Remote Similarity NPD4756 Discovery
0.5784 Remote Similarity NPD4518 Approved
0.5772 Remote Similarity NPD6616 Approved
0.5769 Remote Similarity NPD7637 Suspended
0.5763 Remote Similarity NPD6009 Approved
0.5755 Remote Similarity NPD5654 Approved
0.575 Remote Similarity NPD6054 Approved
0.575 Remote Similarity NPD6319 Approved
0.5748 Remote Similarity NPD6845 Suspended
0.5743 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5739 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5728 Remote Similarity NPD5370 Suspended
0.5728 Remote Similarity NPD4753 Phase 2
0.5728 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5726 Remote Similarity NPD7078 Approved
0.5714 Remote Similarity NPD4137 Phase 3

  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