Structure

Physi-Chem Properties

Molecular Weight:  303.14
Volume:  315.087
LogP:  3.106
LogD:  3.221
LogS:  -5.435
# Rotatable Bonds:  0
TPSA:  39.34
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.692
Synthetic Accessibility Score:  2.838
Fsp3:  0.211
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.797
MDCK Permeability:  2.4298746211570688e-05
Pgp-inhibitor:  0.983
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.032
30% Bioavailability (F30%):  0.119

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.783
Plasma Protein Binding (PPB):  94.04936218261719%
Volume Distribution (VD):  1.049
Pgp-substrate:  3.0593981742858887%

ADMET: Metabolism

CYP1A2-inhibitor:  0.774
CYP1A2-substrate:  0.761
CYP2C19-inhibitor:  0.929
CYP2C19-substrate:  0.396
CYP2C9-inhibitor:  0.798
CYP2C9-substrate:  0.895
CYP2D6-inhibitor:  0.185
CYP2D6-substrate:  0.874
CYP3A4-inhibitor:  0.708
CYP3A4-substrate:  0.345

ADMET: Excretion

Clearance (CL):  3.795
Half-life (T1/2):  0.431

ADMET: Toxicity

hERG Blockers:  0.262
Human Hepatotoxicity (H-HT):  0.643
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.069
Rat Oral Acute Toxicity:  0.936
Maximum Recommended Daily Dose:  0.938
Skin Sensitization:  0.836
Carcinogencity:  0.776
Eye Corrosion:  0.009
Eye Irritation:  0.338
Respiratory Toxicity:  0.983

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Structure MOL file  
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  Natural Product: NPC141612

Natural Product ID:  NPC141612
Common Name*:   TXDUTHBFYKGSAH-SFHVURJKSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  TXDUTHBFYKGSAH-SFHVURJKSA-N
Standard InCHI:  InChI=1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3/t18-/m0/s1
SMILES:  CN1c2ccccc2C(=O)N2CCc3c4ccccc4[nH]c3[C@@H]12
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463165
PubChem CID:   442088
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0001213] Pyridoindoles
          • [CHEMONTID:0001914] Beta carbolines

*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
NPO3894 Dendrobium nobile Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[11575955]
NPO3894 Dendrobium nobile Species Orchidaceae Eukaryota stems Yunnan Province, China 2004 PMID[17253844]
NPO3894 Dendrobium nobile Species Orchidaceae Eukaryota Stems purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea 2006-APR PMID[18052323]
NPO3894 Dendrobium nobile Species Orchidaceae Eukaryota Stems n.a. n.a. PMID[27310249]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7463094]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8201313]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8699182]
NPO22281 Warburgia salutaris Species Canellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30823 Evodia rutaecarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3894 Dendrobium nobile Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14163.1 Hesperocyparis goveniana var. abramsiana Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22281 Warburgia salutaris Species Canellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3894 Dendrobium nobile Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3894 Dendrobium nobile Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30823 Evodia rutaecarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8314 Euodia ruticarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16845 Euodia bodinieri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26538 Phellodendron chinese Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3894 Dendrobium nobile Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4877 Euodia officinalis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3894 Dendrobium nobile Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14163.1 Hesperocyparis goveniana var. abramsiana Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22281 Warburgia salutaris Species Canellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21954 Streptomyces levoris Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17513 Lagochilus hirsutissimus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22242 Phellodendron chinense Species Rutaceae 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
NPT4542 Individual Protein NAD-dependent deacetylase sirtuin 3 Homo sapiens Inhibition = 20.0 % PMID[525766]
NPT1158 Individual Protein NAD-dependent deacetylase sirtuin 2 Homo sapiens Inhibition = 71.0 % PMID[525766]
NPT1046 Individual Protein NAD-dependent deacetylase sirtuin 1 Homo sapiens Inhibition = 4.2 % PMID[525766]
NPT65 Cell Line HepG2 Homo sapiens Inhibition = 69.0 % PMID[525766]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 44.0 % PMID[525766]
NPT83 Cell Line MCF7 Homo sapiens Activity = 39.3 % PMID[525767]
NPT2138 Cell Line MSTO-211H Homo sapiens IC50 = 540.0 nM PMID[525767]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 5400.0 nM PMID[525767]
NPT83 Cell Line MCF7 Homo sapiens Activity = 51.5 % PMID[525767]
NPT83 Cell Line MCF7 Homo sapiens Activity = 41.9 % PMID[525767]
NPT83 Cell Line MCF7 Homo sapiens Activity = 11.9 % PMID[525767]
NPT83 Cell Line MCF7 Homo sapiens Activity = 16.8 % PMID[525767]
NPT83 Cell Line MCF7 Homo sapiens Activity = 27.6 % PMID[525767]
NPT83 Cell Line MCF7 Homo sapiens Activity = 33.2 % PMID[525767]
NPT83 Cell Line MCF7 Homo sapiens Activity = 9.0 % PMID[525767]
NPT83 Cell Line MCF7 Homo sapiens Activity = 8.1 % PMID[525767]
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 200000.0 nM PMID[525769]
NPT400 Cell Line MDA-MB-435 Homo sapiens IC50 = 22100.0 nM PMID[525769]
NPT81 Cell Line A549 Homo sapiens IC50 > 200000.0 nM PMID[525769]
NPT273 Individual Protein Phosphodiesterase 5A Homo sapiens IC50 = 1300.0 nM PMID[525772]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2600.0 nM PMID[525766]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 260.0 nM PMID[525767]
NPT2 Others Unspecified Inhibition = 60.0 % PMID[525767]
NPT2 Others Unspecified Inhibition = 100.0 % PMID[525767]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Survival = 53.22 % PMID[525767]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Survival = 65.47 % PMID[525767]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Survival = 26.75 % PMID[525767]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Survival = 43.09 % PMID[525767]
NPT2 Others Unspecified Tm = 75.5 degrees C PMID[525767]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -4.75 % PMID[525768]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = -1.656 % PMID[525770]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 1.0 % PMID[525771]

☑ 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 NPC141612 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 NPC135601
1.0 High Similarity NPC17273
0.907 High Similarity NPC21429
0.9017 High Similarity NPC133003
0.8603 High Similarity NPC324091
0.858 High Similarity NPC470205
0.8391 Intermediate Similarity NPC161861
0.8258 Intermediate Similarity NPC88110
0.8256 Intermediate Similarity NPC271797
0.8256 Intermediate Similarity NPC21174
0.8242 Intermediate Similarity NPC470440
0.8192 Intermediate Similarity NPC151635
0.8182 Intermediate Similarity NPC252572
0.8171 Intermediate Similarity NPC471943
0.8107 Intermediate Similarity NPC117032
0.8063 Intermediate Similarity NPC317701
0.8043 Intermediate Similarity NPC473666
0.8022 Intermediate Similarity NPC477003
0.8011 Intermediate Similarity NPC191415
0.7989 Intermediate Similarity NPC194881
0.7979 Intermediate Similarity NPC102592
0.7979 Intermediate Similarity NPC471191
0.7979 Intermediate Similarity NPC79356
0.7957 Intermediate Similarity NPC476460
0.7944 Intermediate Similarity NPC284775
0.7919 Intermediate Similarity NPC6865
0.7919 Intermediate Similarity NPC153980
0.7907 Intermediate Similarity NPC476219
0.7872 Intermediate Similarity NPC326422
0.7869 Intermediate Similarity NPC102755
0.7868 Intermediate Similarity NPC72956
0.7865 Intermediate Similarity NPC471944
0.7831 Intermediate Similarity NPC88097
0.7819 Intermediate Similarity NPC272458
0.7784 Intermediate Similarity NPC308931
0.7784 Intermediate Similarity NPC99939
0.7772 Intermediate Similarity NPC117027
0.776 Intermediate Similarity NPC16659
0.7755 Intermediate Similarity NPC243850
0.7739 Intermediate Similarity NPC471193
0.7739 Intermediate Similarity NPC471194
0.7714 Intermediate Similarity NPC76982
0.7713 Intermediate Similarity NPC472112
0.7711 Intermediate Similarity NPC471192
0.7711 Intermediate Similarity NPC470731
0.7705 Intermediate Similarity NPC265710
0.7697 Intermediate Similarity NPC42372
0.7697 Intermediate Similarity NPC115232
0.7697 Intermediate Similarity NPC198988
0.7684 Intermediate Similarity NPC304203
0.767 Intermediate Similarity NPC475990
0.767 Intermediate Similarity NPC474880
0.767 Intermediate Similarity NPC221786
0.7663 Intermediate Similarity NPC91179
0.766 Intermediate Similarity NPC63199
0.766 Intermediate Similarity NPC111602
0.766 Intermediate Similarity NPC102338
0.766 Intermediate Similarity NPC196251
0.7656 Intermediate Similarity NPC167710
0.7654 Intermediate Similarity NPC114637
0.765 Intermediate Similarity NPC473380
0.765 Intermediate Similarity NPC240088
0.7637 Intermediate Similarity NPC293216
0.7632 Intermediate Similarity NPC472113
0.7627 Intermediate Similarity NPC229173
0.7626 Intermediate Similarity NPC116555
0.7624 Intermediate Similarity NPC322064
0.7616 Intermediate Similarity NPC21605
0.7609 Intermediate Similarity NPC11126
0.76 Intermediate Similarity NPC476297
0.7584 Intermediate Similarity NPC214106
0.7574 Intermediate Similarity NPC59084
0.7573 Intermediate Similarity NPC220851
0.7561 Intermediate Similarity NPC272174
0.7558 Intermediate Similarity NPC478186
0.7556 Intermediate Similarity NPC56233
0.7545 Intermediate Similarity NPC325252
0.7542 Intermediate Similarity NPC478184
0.7542 Intermediate Similarity NPC478182
0.754 Intermediate Similarity NPC228835
0.7536 Intermediate Similarity NPC476817
0.7529 Intermediate Similarity NPC473868
0.7529 Intermediate Similarity NPC63157
0.7524 Intermediate Similarity NPC474896
0.7512 Intermediate Similarity NPC257851
0.7512 Intermediate Similarity NPC157931
0.75 Intermediate Similarity NPC204141
0.7488 Intermediate Similarity NPC31097
0.7487 Intermediate Similarity NPC477004
0.7487 Intermediate Similarity NPC237414
0.7476 Intermediate Similarity NPC66777
0.7476 Intermediate Similarity NPC323969
0.7476 Intermediate Similarity NPC471762
0.7474 Intermediate Similarity NPC175474
0.7471 Intermediate Similarity NPC115611
0.7471 Intermediate Similarity NPC2949
0.7461 Intermediate Similarity NPC19692
0.7461 Intermediate Similarity NPC220151
0.746 Intermediate Similarity NPC94752
0.7451 Intermediate Similarity NPC470732
0.7447 Intermediate Similarity NPC467063
0.7446 Intermediate Similarity NPC469529
0.7443 Intermediate Similarity NPC281094
0.7435 Intermediate Similarity NPC329858
0.7433 Intermediate Similarity NPC470677
0.7423 Intermediate Similarity NPC472116
0.7409 Intermediate Similarity NPC472295
0.7409 Intermediate Similarity NPC269886
0.7409 Intermediate Similarity NPC472210
0.7409 Intermediate Similarity NPC81802
0.7409 Intermediate Similarity NPC247735
0.7403 Intermediate Similarity NPC195507
0.7403 Intermediate Similarity NPC2165
0.7391 Intermediate Similarity NPC472123
0.7377 Intermediate Similarity NPC474897
0.7374 Intermediate Similarity NPC293487
0.7368 Intermediate Similarity NPC238499
0.7366 Intermediate Similarity NPC14325
0.7366 Intermediate Similarity NPC28848
0.736 Intermediate Similarity NPC312870
0.736 Intermediate Similarity NPC254240
0.736 Intermediate Similarity NPC199851
0.736 Intermediate Similarity NPC294909
0.736 Intermediate Similarity NPC128265
0.7358 Intermediate Similarity NPC216550
0.7347 Intermediate Similarity NPC52557
0.7344 Intermediate Similarity NPC314333
0.7333 Intermediate Similarity NPC472293
0.7333 Intermediate Similarity NPC245916
0.733 Intermediate Similarity NPC33421
0.733 Intermediate Similarity NPC267811
0.733 Intermediate Similarity NPC17059
0.7322 Intermediate Similarity NPC317430
0.7321 Intermediate Similarity NPC327095
0.7321 Intermediate Similarity NPC312942
0.7318 Intermediate Similarity NPC299594
0.7305 Intermediate Similarity NPC475450
0.7293 Intermediate Similarity NPC242116
0.7288 Intermediate Similarity NPC470233
0.7287 Intermediate Similarity NPC469896
0.7286 Intermediate Similarity NPC40455
0.7283 Intermediate Similarity NPC20144
0.7277 Intermediate Similarity NPC470730
0.7277 Intermediate Similarity NPC477175
0.7277 Intermediate Similarity NPC478077
0.7273 Intermediate Similarity NPC157583
0.7273 Intermediate Similarity NPC195461
0.7273 Intermediate Similarity NPC79129
0.7273 Intermediate Similarity NPC249150
0.7273 Intermediate Similarity NPC81654
0.7273 Intermediate Similarity NPC313985
0.7273 Intermediate Similarity NPC49196
0.7269 Intermediate Similarity NPC477549
0.7268 Intermediate Similarity NPC472292
0.7268 Intermediate Similarity NPC470509
0.7268 Intermediate Similarity NPC471386
0.7268 Intermediate Similarity NPC47190
0.7268 Intermediate Similarity NPC478183
0.7267 Intermediate Similarity NPC284635
0.7263 Intermediate Similarity NPC258480
0.7263 Intermediate Similarity NPC472294
0.7259 Intermediate Similarity NPC50503
0.7251 Intermediate Similarity NPC19170
0.7247 Intermediate Similarity NPC200214
0.7247 Intermediate Similarity NPC325903
0.7246 Intermediate Similarity NPC22079
0.7245 Intermediate Similarity NPC128244
0.7243 Intermediate Similarity NPC475969
0.7243 Intermediate Similarity NPC475859
0.7243 Intermediate Similarity NPC6982
0.7235 Intermediate Similarity NPC218268
0.7234 Intermediate Similarity NPC219336
0.7233 Intermediate Similarity NPC477979
0.7222 Intermediate Similarity NPC220797
0.7222 Intermediate Similarity NPC474318
0.7222 Intermediate Similarity NPC475914
0.7222 Intermediate Similarity NPC268744
0.7222 Intermediate Similarity NPC201266
0.7222 Intermediate Similarity NPC153123
0.7222 Intermediate Similarity NPC472297
0.7222 Intermediate Similarity NPC472296
0.7219 Intermediate Similarity NPC280852
0.7216 Intermediate Similarity NPC201380
0.7216 Intermediate Similarity NPC179787
0.7212 Intermediate Similarity NPC250361
0.7209 Intermediate Similarity NPC165743
0.7202 Intermediate Similarity NPC103119
0.7198 Intermediate Similarity NPC470203
0.7198 Intermediate Similarity NPC478185
0.7196 Intermediate Similarity NPC73994
0.7194 Intermediate Similarity NPC294693
0.7188 Intermediate Similarity NPC66210
0.7186 Intermediate Similarity NPC13456
0.7186 Intermediate Similarity NPC166209
0.7186 Intermediate Similarity NPC473587
0.7186 Intermediate Similarity NPC77241
0.7186 Intermediate Similarity NPC269203
0.7181 Intermediate Similarity NPC217372
0.7181 Intermediate Similarity NPC183662
0.7181 Intermediate Similarity NPC237188

  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 NPC141612 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
0.8272 Intermediate Similarity NPD2442 Approved
0.8272 Intermediate Similarity NPD2443 Approved
0.8258 Intermediate Similarity NPD5473 Discontinued
0.8232 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.8222 Intermediate Similarity NPD7564 Discontinued
0.8207 Intermediate Similarity NPD4922 Phase 2
0.8107 Intermediate Similarity NPD3248 Phase 1
0.8066 Intermediate Similarity NPD3318 Approved
0.8066 Intermediate Similarity NPD3320 Approved
0.8066 Intermediate Similarity NPD3319 Phase 1
0.8041 Intermediate Similarity NPD2408 Discontinued
0.7919 Intermediate Similarity NPD7657 Approved
0.7919 Intermediate Similarity NPD7656 Approved
0.7919 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD6180 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD5820 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD7619 Phase 3
0.7831 Intermediate Similarity NPD7618 Phase 3
0.7802 Intermediate Similarity NPD3079 Approved
0.7802 Intermediate Similarity NPD3077 Approved
0.7802 Intermediate Similarity NPD3078 Approved
0.7802 Intermediate Similarity NPD3076 Approved
0.7778 Intermediate Similarity NPD4863 Approved
0.7766 Intermediate Similarity NPD5592 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD1506 Discontinued
0.7744 Intermediate Similarity NPD7208 Approved
0.7744 Intermediate Similarity NPD7209 Approved
0.7744 Intermediate Similarity NPD7207 Approved
0.7742 Intermediate Similarity NPD5809 Phase 3
0.7737 Intermediate Similarity NPD7406 Phase 2
0.7704 Intermediate Similarity NPD2008 Discontinued
0.7692 Intermediate Similarity NPD4385 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7685 Intermediate Similarity NPD5198 Approved
0.7685 Intermediate Similarity NPD5199 Approved
0.768 Intermediate Similarity NPD3868 Phase 1
0.7672 Intermediate Similarity NPD1658 Discontinued
0.7656 Intermediate Similarity NPD2880 Discontinued
0.7656 Intermediate Similarity NPD5446 Phase 2
0.765 Intermediate Similarity NPD2411 Approved
0.765 Intermediate Similarity NPD7454 Approved
0.765 Intermediate Similarity NPD7455 Approved
0.7644 Intermediate Similarity NPD7024 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD6176 Phase 1
0.7596 Intermediate Similarity NPD4075 Phase 2
0.7577 Intermediate Similarity NPD5854 Approved
0.7576 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7565 Intermediate Similarity NPD6664 Approved
0.7563 Intermediate Similarity NPD8114 Approved
0.7563 Intermediate Similarity NPD8115 Approved
0.7563 Intermediate Similarity NPD6288 Clinical (unspecified phase)
0.7549 Intermediate Similarity NPD6470 Phase 3
0.7526 Intermediate Similarity NPD1982 Phase 1
0.7525 Intermediate Similarity NPD6271 Approved
0.7514 Intermediate Similarity NPD2590 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD7023 Clinical (unspecified phase)
0.7512 Intermediate Similarity NPD6164 Phase 2
0.7512 Intermediate Similarity NPD6165 Phase 2
0.7474 Intermediate Similarity NPD7175 Phase 1
0.7471 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.7461 Intermediate Similarity NPD5853 Phase 3
0.7461 Intermediate Similarity NPD5855 Phase 3
0.7459 Intermediate Similarity NPD4643 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD2837 Discontinued
0.7437 Intermediate Similarity NPD5491 Phase 3
0.7437 Intermediate Similarity NPD5489 Phase 1
0.7432 Intermediate Similarity NPD6828 Phase 2
0.7432 Intermediate Similarity NPD6827 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD3385 Approved
0.7423 Intermediate Similarity NPD1851 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7027 Phase 3
0.7423 Intermediate Similarity NPD4848 Phase 1
0.7411 Intermediate Similarity NPD7817 Phase 1
0.7403 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD3905 Phase 3
0.7376 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD4500 Approved
0.736 Intermediate Similarity NPD4501 Approved
0.736 Intermediate Similarity NPD8248 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD5467 Phase 2
0.7344 Intermediate Similarity NPD4499 Approved
0.7341 Intermediate Similarity NPD5254 Discontinued
0.733 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD4462 Approved
0.733 Intermediate Similarity NPD4463 Approved
0.733 Intermediate Similarity NPD6507 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD4988 Discontinued
0.733 Intermediate Similarity NPD7394 Phase 2
0.7317 Intermediate Similarity NPD5293 Phase 2
0.7296 Intermediate Similarity NPD1952 Discontinued
0.7293 Intermediate Similarity NPD5400 Approved
0.7293 Intermediate Similarity NPD6771 Discontinued
0.7292 Intermediate Similarity NPD5016 Approved
0.7287 Intermediate Similarity NPD2481 Approved
0.7287 Intermediate Similarity NPD2479 Phase 3
0.7287 Intermediate Similarity NPD5146 Suspended
0.7287 Intermediate Similarity NPD3927 Phase 2
0.7286 Intermediate Similarity NPD2879 Approved
0.7286 Intermediate Similarity NPD2881 Approved
0.7273 Intermediate Similarity NPD4601 Approved
0.7273 Intermediate Similarity NPD4600 Approved
0.7268 Intermediate Similarity NPD3431 Approved
0.7268 Intermediate Similarity NPD3430 Approved
0.7259 Intermediate Similarity NPD7204 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD1683 Approved
0.7255 Intermediate Similarity NPD4614 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7249 Intermediate Similarity NPD4011 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD3246 Discontinued
0.7238 Intermediate Similarity NPD5001 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD7727 Phase 2
0.7231 Intermediate Similarity NPD4348 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD1292 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD2405 Phase 3
0.7222 Intermediate Similarity NPD7308 Discontinued
0.7216 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD4051 Discontinued
0.7204 Intermediate Similarity NPD4112 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD3389 Approved
0.7198 Intermediate Similarity NPD3393 Approved
0.7198 Intermediate Similarity NPD3394 Approved
0.7196 Intermediate Similarity NPD1291 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD2509 Approved
0.7192 Intermediate Similarity NPD6459 Phase 2
0.7192 Intermediate Similarity NPD2510 Approved
0.7188 Intermediate Similarity NPD4940 Approved
0.7184 Intermediate Similarity NPD6787 Phase 2
0.7184 Intermediate Similarity NPD8094 Discontinued
0.7182 Intermediate Similarity NPD2214 Approved
0.7182 Intermediate Similarity NPD2213 Approved
0.7178 Intermediate Similarity NPD7568 Phase 1
0.7167 Intermediate Similarity NPD2150 Discontinued
0.7166 Intermediate Similarity NPD4883 Approved
0.7165 Intermediate Similarity NPD1905 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD3323 Discontinued
0.7158 Intermediate Similarity NPD3583 Phase 2
0.715 Intermediate Similarity NPD2009 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD4948 Discontinued
0.715 Intermediate Similarity NPD3961 Discontinued
0.7143 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6210 Phase 3
0.7136 Intermediate Similarity NPD6248 Phase 2
0.7136 Intermediate Similarity NPD6249 Phase 2
0.7136 Intermediate Similarity NPD7195 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD7434 Approved
0.7128 Intermediate Similarity NPD5104 Approved
0.7126 Intermediate Similarity NPD1722 Approved
0.7123 Intermediate Similarity NPD7661 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD2915 Discontinued
0.712 Intermediate Similarity NPD7401 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD6269 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD7724 Phase 2
0.7114 Intermediate Similarity NPD6268 Phase 1
0.7113 Intermediate Similarity NPD1284 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD6285 Phase 2
0.7109 Intermediate Similarity NPD4854 Phase 3
0.7108 Intermediate Similarity NPD6474 Phase 2
0.7107 Intermediate Similarity NPD5464 Approved
0.7105 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD5444 Phase 1
0.7098 Intermediate Similarity NPD6217 Discontinued
0.7095 Intermediate Similarity NPD5965 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD1896 Approved
0.7092 Intermediate Similarity NPD5505 Discontinued
0.709 Intermediate Similarity NPD4181 Approved
0.7086 Intermediate Similarity NPD5918 Discontinued
0.7081 Intermediate Similarity NPD8000 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD5065 Approved
0.7065 Intermediate Similarity NPD6837 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD460 Discontinued
0.7044 Intermediate Similarity NPD5901 Discontinued
0.7044 Intermediate Similarity NPD5000 Phase 2
0.7043 Intermediate Similarity NPD1343 Approved
0.7039 Intermediate Similarity NPD6204 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD4326 Phase 2
0.7031 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4924 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD4334 Discontinued
0.7024 Intermediate Similarity NPD7665 Phase 2
0.7024 Intermediate Similarity NPD7666 Phase 3
0.7022 Intermediate Similarity NPD4547 Phase 3
0.7017 Intermediate Similarity NPD7072 Phase 2
0.7011 Intermediate Similarity NPD1853 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD786 Approved
0.701 Intermediate Similarity NPD7026 Phase 2
0.7005 Intermediate Similarity NPD5475 Discontinued
0.6995 Remote Similarity NPD7483 Phase 2
0.6995 Remote Similarity NPD6178 Phase 3
0.6995 Remote Similarity NPD7482 Phase 2
0.6994 Remote Similarity NPD1262 Discovery
0.699 Remote Similarity NPD1600 Suspended
0.699 Remote Similarity NPD5685 Approved
0.699 Remote Similarity NPD5686 Approved
0.6986 Remote Similarity NPD8242 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data