Structure

Physi-Chem Properties

Molecular Weight:  444.11
Volume:  413.096
LogP:  1.661
LogD:  0.984
LogS:  -3.721
# Rotatable Bonds:  3
TPSA:  153.5
# H-Bond Aceptor:  10
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.385
Synthetic Accessibility Score:  6.125
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.776
MDCK Permeability:  1.9373435861780308e-05
Pgp-inhibitor:  0.1
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.032
20% Bioavailability (F20%):  0.31
30% Bioavailability (F30%):  0.32

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.126
Plasma Protein Binding (PPB):  87.00825500488281%
Volume Distribution (VD):  0.7
Pgp-substrate:  7.1041083335876465%

ADMET: Metabolism

CYP1A2-inhibitor:  0.027
CYP1A2-substrate:  0.95
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.302
CYP2C9-inhibitor:  0.018
CYP2C9-substrate:  0.355
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.189
CYP3A4-inhibitor:  0.576
CYP3A4-substrate:  0.404

ADMET: Excretion

Clearance (CL):  13.821
Half-life (T1/2):  0.074

ADMET: Toxicity

hERG Blockers:  0.031
Human Hepatotoxicity (H-HT):  0.161
Drug-inuced Liver Injury (DILI):  0.884
AMES Toxicity:  0.078
Rat Oral Acute Toxicity:  0.923
Maximum Recommended Daily Dose:  0.055
Skin Sensitization:  0.24
Carcinogencity:  0.631
Eye Corrosion:  0.043
Eye Irritation:  0.164
Respiratory Toxicity:  0.261

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  Natural Product: NPC182693

Natural Product ID:  NPC182693
Common Name*:   WMHYXAXGNZAMDO-AHIRLFQDSA-N
IUPAC Name:   n.a.
Synonyms:   JBIR-85
Standard InCHIKey:  WMHYXAXGNZAMDO-AHIRLFQDSA-N
Standard InCHI:  InChI=1S/C22H20O10/c1-7(23)8-4-11-9-6-21(8)15(19(28)22(9,31-3)20(29)32-11)17(26)13-10(24)5-12(30-2)16(25)14(13)18(21)27/h5,8-9,11,24-25,28H,4,6H2,1-3H3/t8-,9-,11+,21-,22-/m0/s1
SMILES:  CC(=O)[C@@H]1C[C@@H]2[C@@H]3C[C@]41C(=C([C@@]3(C(=O)O2)OC)O)C(=O)c1c(cc(c(c1C4=O)O)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1927941
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

*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
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344559]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344578]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10348041]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10604756]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10695669]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10724004]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10994816]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11099231]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11132958]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11374972]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11473415]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[14738393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Australian n.a. PMID[15497950]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15813185]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15844966]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15974616]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16180833]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1666120]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724845]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16830891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16872146]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17125235]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17315965]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17551212]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17608531]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17844998]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17887721]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17917237]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18044841]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Indonesian n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18205372]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Northwest Territories, Canada 1995 PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18666798]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18776684]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19007176]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19129624]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19191549]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19856955]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19883065]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20092333]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20545334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20836523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028889]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21090727]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21314175]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21639131]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21728289]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21751787]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21807523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21873059]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21879726]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[22145663]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22574670]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22583058]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22591466]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22758660]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22775474]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23387796]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23662937]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24592993]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24754815]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24878306]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24964393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25211234]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25455147]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25495422]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25537064]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25918793]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25934225]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26035239]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26465675]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26798949]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26905826]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31013087]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31298537]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31894983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32298122]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8501018]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[8784423]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8931733]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8982334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031666]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031676]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066767]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066768]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9186568]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9531983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[9711246]

☑ 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 165000.0 nM PMID[449363]

☑ 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 NPC182693 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
0.9 High Similarity NPC20237
0.8994 High Similarity NPC476822
0.8994 High Similarity NPC249181
0.8988 High Similarity NPC87431
0.8947 High Similarity NPC283041
0.8941 High Similarity NPC191930
0.8939 High Similarity NPC295436
0.8929 High Similarity NPC155302
0.8929 High Similarity NPC161947
0.8902 High Similarity NPC473113
0.8864 High Similarity NPC476273
0.8817 High Similarity NPC472055
0.881 High Similarity NPC179732
0.8802 High Similarity NPC472048
0.88 High Similarity NPC245975
0.8793 High Similarity NPC118128
0.8786 High Similarity NPC473095
0.8786 High Similarity NPC473096
0.8779 High Similarity NPC472452
0.8772 High Similarity NPC208120
0.8772 High Similarity NPC173587
0.8765 High Similarity NPC117985
0.8764 High Similarity NPC228209
0.8757 High Similarity NPC473785
0.8757 High Similarity NPC244903
0.8757 High Similarity NPC470339
0.8728 High Similarity NPC473094
0.8728 High Similarity NPC107009
0.8728 High Similarity NPC232936
0.8722 High Similarity NPC174486
0.8722 High Similarity NPC240808
0.8721 High Similarity NPC146584
0.8721 High Similarity NPC21016
0.8721 High Similarity NPC472049
0.8715 High Similarity NPC476170
0.8713 High Similarity NPC215612
0.8708 High Similarity NPC475996
0.8701 High Similarity NPC23553
0.8701 High Similarity NPC207467
0.8701 High Similarity NPC77179
0.869 High Similarity NPC234485
0.869 High Similarity NPC79998
0.8689 High Similarity NPC314020
0.8686 High Similarity NPC158226
0.8678 High Similarity NPC213416
0.8671 High Similarity NPC170245
0.8663 High Similarity NPC475985
0.8663 High Similarity NPC29055
0.8663 High Similarity NPC475055
0.8659 High Similarity NPC246153
0.8659 High Similarity NPC475656
0.8659 High Similarity NPC8927
0.8659 High Similarity NPC475148
0.8659 High Similarity NPC240508
0.8652 High Similarity NPC473729
0.8652 High Similarity NPC473607
0.8647 High Similarity NPC477410
0.8644 High Similarity NPC478050
0.8644 High Similarity NPC227275
0.8639 High Similarity NPC150227
0.8636 High Similarity NPC30550
0.8636 High Similarity NPC471969
0.8636 High Similarity NPC476311
0.8631 High Similarity NPC127172
0.8629 High Similarity NPC313717
0.8629 High Similarity NPC315306
0.8629 High Similarity NPC472276
0.8621 High Similarity NPC126204
0.8613 High Similarity NPC473286
0.8613 High Similarity NPC326520
0.8613 High Similarity NPC102372
0.8596 High Similarity NPC221820
0.8596 High Similarity NPC470334
0.8596 High Similarity NPC185617
0.8596 High Similarity NPC233978
0.8588 High Similarity NPC294149
0.8588 High Similarity NPC246466
0.8588 High Similarity NPC77679
0.8588 High Similarity NPC190020
0.8588 High Similarity NPC84935
0.8588 High Similarity NPC162248
0.858 High Similarity NPC472620
0.858 High Similarity NPC199926
0.858 High Similarity NPC68727
0.8571 High Similarity NPC99613
0.8571 High Similarity NPC242395
0.8571 High Similarity NPC165456
0.8571 High Similarity NPC49487
0.8571 High Similarity NPC165979
0.8571 High Similarity NPC163130
0.8571 High Similarity NPC475805
0.8563 High Similarity NPC103509
0.8556 High Similarity NPC150977
0.8556 High Similarity NPC471842
0.8555 High Similarity NPC41301
0.8547 High Similarity NPC113446
0.8547 High Similarity NPC65746
0.8547 High Similarity NPC201560
0.8531 High Similarity NPC475080
0.8531 High Similarity NPC469393
0.8529 High Similarity NPC472050
0.8523 High Similarity NPC102277
0.8523 High Similarity NPC124470
0.8523 High Similarity NPC109827
0.8523 High Similarity NPC279209
0.8523 High Similarity NPC72696
0.8523 High Similarity NPC101107
0.8521 High Similarity NPC273248
0.8521 High Similarity NPC478231
0.8521 High Similarity NPC192189
0.8514 High Similarity NPC117854
0.8514 High Similarity NPC150131
0.8514 High Similarity NPC478060
0.8514 High Similarity NPC158761
0.8514 High Similarity NPC472622
0.8514 High Similarity NPC471975
0.8514 High Similarity NPC470377
0.8514 High Similarity NPC6588
0.8514 High Similarity NPC470374
0.8514 High Similarity NPC478059
0.8514 High Similarity NPC470456
0.8514 High Similarity NPC477154
0.8514 High Similarity NPC476306
0.8508 High Similarity NPC71260
0.8506 High Similarity NPC314653
0.8506 High Similarity NPC316262
0.8506 High Similarity NPC470457
0.8506 High Similarity NPC224280
0.8506 High Similarity NPC8070
0.85 High Similarity NPC170203
0.85 High Similarity NPC208069
0.85 High Similarity NPC47883
0.85 High Similarity NPC265795
0.8497 Intermediate Similarity NPC191360
0.8497 Intermediate Similarity NPC48860
0.8492 Intermediate Similarity NPC476210
0.8492 Intermediate Similarity NPC246877
0.8492 Intermediate Similarity NPC476199
0.8488 Intermediate Similarity NPC84571
0.8483 Intermediate Similarity NPC289244
0.8483 Intermediate Similarity NPC139350
0.8475 Intermediate Similarity NPC121333
0.8471 Intermediate Similarity NPC471456
0.8471 Intermediate Similarity NPC478221
0.8471 Intermediate Similarity NPC16082
0.8471 Intermediate Similarity NPC82592
0.8466 Intermediate Similarity NPC280493
0.8466 Intermediate Similarity NPC152477
0.8466 Intermediate Similarity NPC326877
0.8466 Intermediate Similarity NPC328321
0.8466 Intermediate Similarity NPC472619
0.8466 Intermediate Similarity NPC288813
0.8466 Intermediate Similarity NPC177480
0.8466 Intermediate Similarity NPC188079
0.8462 Intermediate Similarity NPC113608
0.8462 Intermediate Similarity NPC161778
0.8462 Intermediate Similarity NPC197972
0.8462 Intermediate Similarity NPC268992
0.8462 Intermediate Similarity NPC470337
0.8462 Intermediate Similarity NPC470338
0.8462 Intermediate Similarity NPC51824
0.8457 Intermediate Similarity NPC62444
0.8457 Intermediate Similarity NPC477517
0.8457 Intermediate Similarity NPC470462
0.8457 Intermediate Similarity NPC472621
0.8457 Intermediate Similarity NPC29160
0.8453 Intermediate Similarity NPC470332
0.8452 Intermediate Similarity NPC96501
0.8452 Intermediate Similarity NPC216917
0.8448 Intermediate Similarity NPC152659
0.8448 Intermediate Similarity NPC220313
0.8448 Intermediate Similarity NPC205265
0.8448 Intermediate Similarity NPC248638
0.8448 Intermediate Similarity NPC236521
0.8448 Intermediate Similarity NPC134047
0.8448 Intermediate Similarity NPC474350
0.8448 Intermediate Similarity NPC173729
0.8448 Intermediate Similarity NPC476931
0.8448 Intermediate Similarity NPC472278
0.8448 Intermediate Similarity NPC18100
0.8448 Intermediate Similarity NPC472281
0.8448 Intermediate Similarity NPC223006
0.8448 Intermediate Similarity NPC272750
0.8448 Intermediate Similarity NPC473313
0.8448 Intermediate Similarity NPC470459
0.8448 Intermediate Similarity NPC329669
0.8448 Intermediate Similarity NPC273959
0.8444 Intermediate Similarity NPC70318
0.8439 Intermediate Similarity NPC61010
0.8439 Intermediate Similarity NPC311740
0.8439 Intermediate Similarity NPC187354
0.8439 Intermediate Similarity NPC476929
0.8439 Intermediate Similarity NPC112418
0.8436 Intermediate Similarity NPC24258
0.8436 Intermediate Similarity NPC98943
0.843 Intermediate Similarity NPC45846
0.843 Intermediate Similarity NPC476242
0.8427 Intermediate Similarity NPC476152
0.8427 Intermediate Similarity NPC470333
0.8427 Intermediate Similarity NPC472054

  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 NPC182693 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
0.8457 Intermediate Similarity NPD7473 Discontinued
0.8391 Intermediate Similarity NPD6232 Discontinued
0.8278 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8208 Intermediate Similarity NPD3882 Suspended
0.8192 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8192 Intermediate Similarity NPD6166 Phase 2
0.8192 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.815 Intermediate Similarity NPD3817 Phase 2
0.8142 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8118 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8114 Intermediate Similarity NPD6234 Discontinued
0.8103 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD2801 Approved
0.8068 Intermediate Similarity NPD5494 Approved
0.8056 Intermediate Similarity NPD5844 Phase 1
0.8035 Intermediate Similarity NPD1934 Approved
0.8011 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD3818 Discontinued
0.8 Intermediate Similarity NPD8434 Phase 2
0.7989 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7955 Intermediate Similarity NPD7075 Discontinued
0.7941 Intermediate Similarity NPD2534 Approved
0.7941 Intermediate Similarity NPD2532 Approved
0.7941 Intermediate Similarity NPD2533 Approved
0.7931 Intermediate Similarity NPD37 Approved
0.7901 Intermediate Similarity NPD7228 Approved
0.7898 Intermediate Similarity NPD4966 Approved
0.7898 Intermediate Similarity NPD4967 Phase 2
0.7898 Intermediate Similarity NPD4965 Approved
0.7886 Intermediate Similarity NPD1465 Phase 2
0.7869 Intermediate Similarity NPD6797 Phase 2
0.7869 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD5402 Approved
0.7829 Intermediate Similarity NPD6801 Discontinued
0.7826 Intermediate Similarity NPD7251 Discontinued
0.7821 Intermediate Similarity NPD6959 Discontinued
0.7816 Intermediate Similarity NPD6599 Discontinued
0.7814 Intermediate Similarity NPD7074 Phase 3
0.7784 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7808 Phase 3
0.776 Intermediate Similarity NPD7054 Approved
0.774 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD1247 Approved
0.7717 Intermediate Similarity NPD7472 Approved
0.7714 Intermediate Similarity NPD4380 Phase 2
0.7713 Intermediate Similarity NPD8150 Discontinued
0.7704 Intermediate Similarity NPD7435 Discontinued
0.7692 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD1512 Approved
0.7684 Intermediate Similarity NPD7819 Suspended
0.767 Intermediate Similarity NPD7411 Suspended
0.7611 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD3751 Discontinued
0.7572 Intermediate Similarity NPD6799 Approved
0.7572 Intermediate Similarity NPD1511 Approved
0.7568 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD6190 Approved
0.7557 Intermediate Similarity NPD3226 Approved
0.7556 Intermediate Similarity NPD3749 Approved
0.7551 Intermediate Similarity NPD6780 Approved
0.7551 Intermediate Similarity NPD6777 Approved
0.7551 Intermediate Similarity NPD6776 Approved
0.7551 Intermediate Similarity NPD6779 Approved
0.7551 Intermediate Similarity NPD6778 Approved
0.7551 Intermediate Similarity NPD6781 Approved
0.7551 Intermediate Similarity NPD6782 Approved
0.7544 Intermediate Similarity NPD2800 Approved
0.7529 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD7199 Phase 2
0.7514 Intermediate Similarity NPD919 Approved
0.75 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7874 Approved
0.7459 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD6559 Discontinued
0.7447 Intermediate Similarity NPD7240 Approved
0.7446 Intermediate Similarity NPD3926 Phase 2
0.7443 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD5403 Approved
0.7391 Intermediate Similarity NPD5711 Approved
0.7391 Intermediate Similarity NPD3787 Discontinued
0.7391 Intermediate Similarity NPD5710 Approved
0.735 Intermediate Similarity NPD7697 Approved
0.735 Intermediate Similarity NPD7696 Phase 3
0.735 Intermediate Similarity NPD7698 Approved
0.734 Intermediate Similarity NPD8151 Discontinued
0.7337 Intermediate Similarity NPD230 Phase 1
0.733 Intermediate Similarity NPD5401 Approved
0.733 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD7870 Phase 2
0.7313 Intermediate Similarity NPD7871 Phase 2
0.7312 Intermediate Similarity NPD2403 Approved
0.7299 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD3750 Approved
0.7296 Intermediate Similarity NPD6535 Approved
0.7296 Intermediate Similarity NPD6534 Approved
0.7294 Intermediate Similarity NPD6651 Approved
0.7291 Intermediate Similarity NPD7701 Phase 2
0.7286 Intermediate Similarity NPD7907 Approved
0.7277 Intermediate Similarity NPD8313 Approved
0.7277 Intermediate Similarity NPD8312 Approved
0.7268 Intermediate Similarity NPD7801 Approved
0.7267 Intermediate Similarity NPD2935 Discontinued
0.7263 Intermediate Similarity NPD7685 Pre-registration
0.725 Intermediate Similarity NPD2494 Approved
0.725 Intermediate Similarity NPD2493 Approved
0.7243 Intermediate Similarity NPD8127 Discontinued
0.7232 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD4582 Approved
0.7228 Intermediate Similarity NPD8319 Approved
0.7228 Intermediate Similarity NPD4583 Approved
0.7228 Intermediate Similarity NPD8320 Phase 1
0.7225 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD7768 Phase 2
0.7209 Intermediate Similarity NPD1510 Phase 2
0.7209 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD4628 Phase 3
0.72 Intermediate Similarity NPD8166 Discontinued
0.719 Intermediate Similarity NPD4111 Phase 1
0.719 Intermediate Similarity NPD4665 Approved
0.7186 Intermediate Similarity NPD7700 Phase 2
0.7186 Intermediate Similarity NPD7699 Phase 2
0.7184 Intermediate Similarity NPD1549 Phase 2
0.7178 Intermediate Similarity NPD4002 Approved
0.7178 Intermediate Similarity NPD4004 Approved
0.7175 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD7390 Discontinued
0.7168 Intermediate Similarity NPD6099 Approved
0.7168 Intermediate Similarity NPD6100 Approved
0.7164 Intermediate Similarity NPD3452 Approved
0.7164 Intermediate Similarity NPD3450 Approved
0.715 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD7783 Phase 2
0.7101 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD1607 Approved
0.7076 Intermediate Similarity NPD943 Approved
0.7076 Intermediate Similarity NPD1240 Approved
0.7072 Intermediate Similarity NPD7458 Discontinued
0.7069 Intermediate Similarity NPD2796 Approved
0.7056 Intermediate Similarity NPD2488 Approved
0.7056 Intermediate Similarity NPD2490 Approved
0.7056 Intermediate Similarity NPD920 Approved
0.705 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD2973 Approved
0.705 Intermediate Similarity NPD2974 Approved
0.705 Intermediate Similarity NPD2975 Approved
0.7044 Intermediate Similarity NPD6823 Phase 2
0.703 Intermediate Similarity NPD4580 Approved
0.7021 Intermediate Similarity NPD7229 Phase 3
0.7017 Intermediate Similarity NPD1653 Approved
0.7011 Intermediate Similarity NPD3748 Approved
0.701 Intermediate Similarity NPD7680 Approved
0.7006 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6273 Approved
0.6995 Remote Similarity NPD6765 Approved
0.6995 Remote Similarity NPD6764 Approved
0.6974 Remote Similarity NPD8407 Phase 2
0.6963 Remote Similarity NPD7799 Discontinued
0.6943 Remote Similarity NPD5953 Discontinued
0.694 Remote Similarity NPD7028 Phase 2
0.6936 Remote Similarity NPD447 Suspended
0.6934 Remote Similarity NPD8404 Phase 2
0.6932 Remote Similarity NPD1471 Phase 3
0.6932 Remote Similarity NPD2346 Discontinued
0.6927 Remote Similarity NPD7236 Approved
0.6927 Remote Similarity NPD3300 Phase 2
0.6923 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6919 Remote Similarity NPD5760 Phase 2
0.6919 Remote Similarity NPD5761 Phase 2
0.691 Remote Similarity NPD7003 Approved
0.6907 Remote Similarity NPD8368 Discontinued
0.6901 Remote Similarity NPD3027 Phase 3
0.6885 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5353 Approved
0.6879 Remote Similarity NPD4060 Phase 1
0.6879 Remote Similarity NPD3620 Phase 2
0.6879 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6878 Remote Similarity NPD3057 Approved
0.6875 Remote Similarity NPD1551 Phase 2
0.6863 Remote Similarity NPD4107 Approved
0.686 Remote Similarity NPD1699 Clinical (unspecified phase)
0.686 Remote Similarity NPD3764 Approved
0.686 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6854 Remote Similarity NPD1243 Approved
0.6853 Remote Similarity NPD6785 Approved
0.6853 Remote Similarity NPD6784 Approved
0.6851 Remote Similarity NPD642 Clinical (unspecified phase)
0.6839 Remote Similarity NPD6355 Discontinued
0.6839 Remote Similarity NPD7286 Phase 2
0.6834 Remote Similarity NPD8361 Approved
0.6834 Remote Similarity NPD8435 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