Structure

Physi-Chem Properties

Molecular Weight:  272.1
Volume:  284.885
LogP:  4.727
LogD:  3.242
LogS:  -2.988
# Rotatable Bonds:  2
TPSA:  80.92
# H-Bond Aceptor:  4
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.497
Synthetic Accessibility Score:  2.984
Fsp3:  0.125
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.017
MDCK Permeability:  1.4842103155388031e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.237
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.492
30% Bioavailability (F30%):  0.719

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.009
Plasma Protein Binding (PPB):  99.13569641113281%
Volume Distribution (VD):  0.566
Pgp-substrate:  3.5469300746917725%

ADMET: Metabolism

CYP1A2-inhibitor:  0.973
CYP1A2-substrate:  0.912
CYP2C19-inhibitor:  0.121
CYP2C19-substrate:  0.065
CYP2C9-inhibitor:  0.574
CYP2C9-substrate:  0.899
CYP2D6-inhibitor:  0.554
CYP2D6-substrate:  0.907
CYP3A4-inhibitor:  0.072
CYP3A4-substrate:  0.165

ADMET: Excretion

Clearance (CL):  8.126
Half-life (T1/2):  0.748

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.235
Drug-inuced Liver Injury (DILI):  0.419
AMES Toxicity:  0.809
Rat Oral Acute Toxicity:  0.76
Maximum Recommended Daily Dose:  0.929
Skin Sensitization:  0.966
Carcinogencity:  0.588
Eye Corrosion:  0.186
Eye Irritation:  0.949
Respiratory Toxicity:  0.788

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General Info & Identifiers & Properties  
Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC306765

Natural Product ID:  NPC306765
Common Name*:   Deoxyshikonin
IUPAC Name:   5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione
Synonyms:   11-Deoxyalkannin; Deoxyshikonin
Standard InCHIKey:  VOMDIEGPEURZJO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H16O4/c1-9(2)4-3-5-10-8-13(19)14-11(17)6-7-12(18)15(14)16(10)20/h4,6-8,17-18H,3,5H2,1-2H3
SMILES:  CC(=CCCC1=CC(=O)c2c(C1=O)c(O)ccc2O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL486627
PubChem CID:   98914
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0000153] Naphthoquinones

*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
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. root n.a. DOI[10.1007/s11418-007-0221-0]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[12502328]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. leaf n.a. PMID[16494492]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. stem n.a. PMID[16494492]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[16562834]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[17157006]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[17190445]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. fruit n.a. PMID[17190445]
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[17488128]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[17489633]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[19217780]
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[19534474]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota leaves and stems n.a. n.a. PMID[20146529]
NPO12855 Alkanna cappadocica Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[20405844]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[23265871]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. fruit n.a. PMID[24155209]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[24959987]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[25302569]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[3373224]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[7775984]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11300 Eucalyptus coccifera Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9209 Rhizomnium magnifolium Species Mniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26982 Callyspongia siphonella Species Callyspongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12855 Alkanna cappadocica Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae 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
NPT139 Cell Line HT-29 Homo sapiens IC50 = 5120.0 nM PMID[489832]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 5080.0 nM PMID[489832]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 4290.0 nM PMID[489832]
NPT2296 Cell Line AU565 Homo sapiens IC50 = 920.0 nM PMID[489832]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 900.0 nM PMID[489832]
NPT858 Cell Line LNCaP Homo sapiens IC50 = 12210.0 nM PMID[489832]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 790.0 nM PMID[489832]
NPT165 Cell Line HeLa Homo sapiens IC50 = 850.0 nM PMID[489832]
NPT134 Cell Line SK-BR-3 Homo sapiens IC50 = 690.0 nM PMID[489832]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 1240.0 nM PMID[489832]
NPT2405 Cell Line SAOS-2 Homo sapiens IC50 = 850.0 nM PMID[489832]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 660.0 nM PMID[489832]
NPT886 Cell Line NIH3T3 Mus musculus IC50 = 5840.0 nM PMID[489832]
NPT2228 Individual Protein Neuraminidase Influenza A virus (strain A/Brevig Mission/1/1918 H1N1) (Influenza Avirus (strain A/South Carolina/1/1918 H1N1)) IC50 = 63400.0 nM PMID[489833]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 1.52 % PMID[489834]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 200.0 ug.mL-1 PMID[489831]
NPT1390 Organism Kocuria rosea Kocuria rosea MIC = 100.0 ug.mL-1 PMID[489831]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 50.0 ug.mL-1 PMID[489831]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 200.0 ug.mL-1 PMID[489831]
NPT1533 Organism Saccharomyces Saccharomyces MIC = 6.2 ug.mL-1 PMID[489831]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC = 25.0 ug.mL-1 PMID[489831]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC = 12.5 ug.mL-1 PMID[489831]
NPT4799 Organism Trichophyton tonsurans var. sulfureum Trichophyton tonsurans var. sulfureum MIC = 12.5 ug.mL-1 PMID[489831]
NPT327 Organism Microsporum gypseum Microsporum gypseum MIC = 6.2 ug.mL-1 PMID[489831]
NPT328 Organism Epidermophyton floccosum Epidermophyton floccosum MIC = 6.2 ug.mL-1 PMID[489831]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 6020.0 nM PMID[489832]
NPT2 Others Unspecified Ki = 11900.0 nM PMID[489833]
NPT2 Others Unspecified Kic = 15.9 uM PMID[489833]
NPT2 Others Unspecified IC50 = 27500.0 nM PMID[489833]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -2.66 % PMID[489834]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 66.4 % PMID[489835]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 87.3 % PMID[489835]

☑ 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 NPC306765 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
0.952 High Similarity NPC246693
0.952 High Similarity NPC242358
0.952 High Similarity NPC110609
0.9431 High Similarity NPC471530
0.9412 High Similarity NPC206778
0.9412 High Similarity NPC285829
0.935 High Similarity NPC96915
0.9344 High Similarity NPC310540
0.9339 High Similarity NPC307174
0.9328 High Similarity NPC232178
0.9297 High Similarity NPC281513
0.9297 High Similarity NPC22222
0.9194 High Similarity NPC1991
0.9194 High Similarity NPC231774
0.9194 High Similarity NPC3224
0.916 High Similarity NPC269414
0.9134 High Similarity NPC205992
0.9127 High Similarity NPC278928
0.9127 High Similarity NPC34414
0.9127 High Similarity NPC146647
0.9106 High Similarity NPC375356
0.9106 High Similarity NPC477153
0.9077 High Similarity NPC272268
0.9076 High Similarity NPC477453
0.9076 High Similarity NPC108288
0.9055 High Similarity NPC55949
0.9048 High Similarity NPC48248
0.9048 High Similarity NPC237225
0.904 High Similarity NPC295202
0.904 High Similarity NPC227741
0.904 High Similarity NPC136342
0.904 High Similarity NPC49647
0.9024 High Similarity NPC300274
0.9015 High Similarity NPC471602
0.9015 High Similarity NPC256463
0.9015 High Similarity NPC299405
0.9015 High Similarity NPC216312
0.9015 High Similarity NPC306835
0.9015 High Similarity NPC111422
0.9015 High Similarity NPC29771
0.9015 High Similarity NPC476477
0.9008 High Similarity NPC245923
0.8992 High Similarity NPC240163
0.8984 High Similarity NPC244699
0.896 High Similarity NPC103540
0.896 High Similarity NPC131799
0.8947 High Similarity NPC37992
0.8947 High Similarity NPC327916
0.8947 High Similarity NPC147542
0.8947 High Similarity NPC241349
0.8947 High Similarity NPC32749
0.8947 High Similarity NPC220496
0.8947 High Similarity NPC42262
0.8931 High Similarity NPC155211
0.8931 High Similarity NPC474813
0.8915 High Similarity NPC58685
0.8906 High Similarity NPC198305
0.8898 High Similarity NPC282923
0.8889 High Similarity NPC51037
0.8881 High Similarity NPC471444
0.8881 High Similarity NPC257003
0.888 High Similarity NPC74507
0.888 High Similarity NPC142956
0.888 High Similarity NPC234890
0.8864 High Similarity NPC305060
0.8855 High Similarity NPC283088
0.8846 High Similarity NPC53896
0.8846 High Similarity NPC115458
0.8846 High Similarity NPC171968
0.8837 High Similarity NPC85342
0.8833 High Similarity NPC161304
0.8828 High Similarity NPC99731
0.8815 High Similarity NPC474300
0.8779 High Similarity NPC50924
0.876 High Similarity NPC31539
0.876 High Similarity NPC136588
0.876 High Similarity NPC199253
0.876 High Similarity NPC117609
0.875 High Similarity NPC476473
0.873 High Similarity NPC68756
0.873 High Similarity NPC152525
0.871 High Similarity NPC472046
0.8702 High Similarity NPC225051
0.8692 High Similarity NPC17083
0.8686 High Similarity NPC274085
0.8686 High Similarity NPC89664
0.8672 High Similarity NPC45537
0.8651 High Similarity NPC275145
0.8647 High Similarity NPC193358
0.8647 High Similarity NPC472308
0.8629 High Similarity NPC7151
0.8629 High Similarity NPC473662
0.8629 High Similarity NPC216297
0.8626 High Similarity NPC70622
0.8626 High Similarity NPC309430
0.8618 High Similarity NPC41567
0.8615 High Similarity NPC475741
0.8605 High Similarity NPC165257
0.8603 High Similarity NPC124365
0.8603 High Similarity NPC187843
0.8594 High Similarity NPC15837
0.8593 High Similarity NPC477408
0.8593 High Similarity NPC295339
0.8583 High Similarity NPC173978
0.8571 High Similarity NPC161632
0.8571 High Similarity NPC282577
0.8571 High Similarity NPC80035
0.8561 High Similarity NPC52407
0.856 High Similarity NPC222876
0.856 High Similarity NPC301987
0.856 High Similarity NPC179092
0.856 High Similarity NPC35856
0.856 High Similarity NPC178395
0.856 High Similarity NPC244994
0.856 High Similarity NPC272454
0.856 High Similarity NPC115188
0.856 High Similarity NPC292665
0.856 High Similarity NPC26433
0.856 High Similarity NPC159760
0.8551 High Similarity NPC477409
0.855 High Similarity NPC205360
0.8548 High Similarity NPC233165
0.8548 High Similarity NPC184579
0.8538 High Similarity NPC25736
0.8519 High Similarity NPC173980
0.8519 High Similarity NPC61590
0.8519 High Similarity NPC206207
0.8507 High Similarity NPC474311
0.8504 High Similarity NPC135062
0.8496 Intermediate Similarity NPC288089
0.8496 Intermediate Similarity NPC166480
0.8496 Intermediate Similarity NPC282780
0.8489 Intermediate Similarity NPC471683
0.8485 Intermediate Similarity NPC477406
0.8485 Intermediate Similarity NPC88864
0.8473 Intermediate Similarity NPC31799
0.8462 Intermediate Similarity NPC96024
0.8456 Intermediate Similarity NPC138099
0.8456 Intermediate Similarity NPC242994
0.8456 Intermediate Similarity NPC143438
0.845 Intermediate Similarity NPC160499
0.845 Intermediate Similarity NPC254492
0.8444 Intermediate Similarity NPC238108
0.8444 Intermediate Similarity NPC147418
0.8438 Intermediate Similarity NPC199273
0.8425 Intermediate Similarity NPC91478
0.8425 Intermediate Similarity NPC244351
0.8421 Intermediate Similarity NPC294226
0.8421 Intermediate Similarity NPC193169
0.8421 Intermediate Similarity NPC254603
0.8417 Intermediate Similarity NPC103910
0.8413 Intermediate Similarity NPC165197
0.8403 Intermediate Similarity NPC224584
0.8394 Intermediate Similarity NPC315578
0.8394 Intermediate Similarity NPC181560
0.8394 Intermediate Similarity NPC169452
0.8387 Intermediate Similarity NPC125252
0.8387 Intermediate Similarity NPC160199
0.8385 Intermediate Similarity NPC72667
0.8382 Intermediate Similarity NPC13715
0.8382 Intermediate Similarity NPC4214
0.8372 Intermediate Similarity NPC167055
0.8372 Intermediate Similarity NPC240744
0.8372 Intermediate Similarity NPC123506
0.837 Intermediate Similarity NPC315275
0.837 Intermediate Similarity NPC141934
0.8359 Intermediate Similarity NPC182646
0.8358 Intermediate Similarity NPC161964
0.8358 Intermediate Similarity NPC472262
0.8358 Intermediate Similarity NPC12070
0.8358 Intermediate Similarity NPC44437
0.8358 Intermediate Similarity NPC287604
0.8346 Intermediate Similarity NPC120545
0.8346 Intermediate Similarity NPC25168
0.8346 Intermediate Similarity NPC118253
0.8345 Intermediate Similarity NPC471682
0.8345 Intermediate Similarity NPC21873
0.8333 Intermediate Similarity NPC108129
0.8321 Intermediate Similarity NPC114620
0.8321 Intermediate Similarity NPC103337
0.8321 Intermediate Similarity NPC26924
0.8321 Intermediate Similarity NPC1268
0.8319 Intermediate Similarity NPC34715
0.8309 Intermediate Similarity NPC53206
0.8309 Intermediate Similarity NPC471905
0.8309 Intermediate Similarity NPC53414
0.8308 Intermediate Similarity NPC71610
0.8308 Intermediate Similarity NPC472047
0.8306 Intermediate Similarity NPC312800
0.8298 Intermediate Similarity NPC300540
0.8296 Intermediate Similarity NPC249272
0.8296 Intermediate Similarity NPC258502
0.8295 Intermediate Similarity NPC236189
0.8293 Intermediate Similarity NPC163154
0.8286 Intermediate Similarity NPC10764
0.8284 Intermediate Similarity NPC114183
0.8284 Intermediate Similarity NPC314048
0.8281 Intermediate Similarity NPC283514
0.8281 Intermediate Similarity NPC297193
0.8273 Intermediate Similarity NPC193555

  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 NPC306765 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
0.9076 High Similarity NPD405 Clinical (unspecified phase)
0.896 High Similarity NPD1470 Approved
0.864 High Similarity NPD1201 Approved
0.8235 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8085 Intermediate Similarity NPD3300 Phase 2
0.8043 Intermediate Similarity NPD2935 Discontinued
0.7986 Intermediate Similarity NPD2346 Discontinued
0.7914 Intermediate Similarity NPD5408 Approved
0.7914 Intermediate Similarity NPD5404 Approved
0.7914 Intermediate Similarity NPD5405 Approved
0.7914 Intermediate Similarity NPD5406 Approved
0.7907 Intermediate Similarity NPD2932 Approved
0.7778 Intermediate Similarity NPD7390 Discontinued
0.7769 Intermediate Similarity NPD3019 Approved
0.7755 Intermediate Similarity NPD3226 Approved
0.7714 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7698 Intermediate Similarity NPD7635 Approved
0.7692 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD1164 Approved
0.7681 Intermediate Similarity NPD943 Approved
0.7661 Intermediate Similarity NPD9266 Approved
0.7661 Intermediate Similarity NPD74 Approved
0.763 Intermediate Similarity NPD2798 Approved
0.7603 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD9493 Approved
0.7589 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD2799 Discontinued
0.7581 Intermediate Similarity NPD9264 Approved
0.7581 Intermediate Similarity NPD9267 Approved
0.7581 Intermediate Similarity NPD9263 Approved
0.7536 Intermediate Similarity NPD2313 Discontinued
0.7521 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD2344 Approved
0.7381 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD844 Approved
0.7313 Intermediate Similarity NPD3026 Approved
0.7313 Intermediate Similarity NPD3023 Approved
0.7308 Intermediate Similarity NPD9281 Approved
0.7308 Intermediate Similarity NPD5951 Approved
0.7293 Intermediate Similarity NPD3025 Approved
0.7293 Intermediate Similarity NPD3024 Approved
0.7286 Intermediate Similarity NPD3764 Approved
0.7279 Intermediate Similarity NPD2309 Approved
0.7273 Intermediate Similarity NPD288 Approved
0.7258 Intermediate Similarity NPD9261 Approved
0.7254 Intermediate Similarity NPD447 Suspended
0.7248 Intermediate Similarity NPD2532 Approved
0.7248 Intermediate Similarity NPD2533 Approved
0.7248 Intermediate Similarity NPD2534 Approved
0.7241 Intermediate Similarity NPD1471 Phase 3
0.7215 Intermediate Similarity NPD6232 Discontinued
0.7211 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD9717 Approved
0.7203 Intermediate Similarity NPD1607 Approved
0.7192 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD4750 Phase 3
0.7188 Intermediate Similarity NPD7473 Discontinued
0.7183 Intermediate Similarity NPD1240 Approved
0.7174 Intermediate Similarity NPD1203 Approved
0.7165 Intermediate Similarity NPD2342 Discontinued
0.7163 Intermediate Similarity NPD411 Approved
0.7133 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD4626 Approved
0.7103 Intermediate Similarity NPD1510 Phase 2
0.7101 Intermediate Similarity NPD1876 Approved
0.7097 Intermediate Similarity NPD7819 Suspended
0.7097 Intermediate Similarity NPD2801 Approved
0.7095 Intermediate Similarity NPD8166 Discontinued
0.7095 Intermediate Similarity NPD7003 Approved
0.7095 Intermediate Similarity NPD3750 Approved
0.708 Intermediate Similarity NPD4878 Approved
0.7077 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD5029 Approved
0.7073 Intermediate Similarity NPD5031 Approved
0.7073 Intermediate Similarity NPD5027 Approved
0.7045 Intermediate Similarity NPD497 Approved
0.7037 Intermediate Similarity NPD1651 Approved
0.7032 Intermediate Similarity NPD6844 Discontinued
0.7031 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4955 Approved
0.703 Intermediate Similarity NPD5026 Approved
0.703 Intermediate Similarity NPD4954 Approved
0.703 Intermediate Similarity NPD5028 Approved
0.703 Intermediate Similarity NPD5034 Approved
0.703 Intermediate Similarity NPD36 Approved
0.7029 Intermediate Similarity NPD1755 Approved
0.7027 Intermediate Similarity NPD2800 Approved
0.7025 Intermediate Similarity NPD845 Approved
0.7016 Intermediate Similarity NPD3020 Approved
0.7007 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7609 Phase 3
0.6993 Remote Similarity NPD6663 Approved
0.6992 Remote Similarity NPD6671 Approved
0.6987 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6984 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6984 Remote Similarity NPD1929 Approved
0.6984 Remote Similarity NPD1930 Approved
0.6982 Remote Similarity NPD8397 Clinical (unspecified phase)
0.698 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6978 Remote Similarity NPD1283 Approved
0.6977 Remote Similarity NPD2182 Approved
0.697 Remote Similarity NPD496 Approved
0.697 Remote Similarity NPD495 Approved
0.697 Remote Similarity NPD5030 Phase 2
0.697 Remote Similarity NPD498 Approved
0.6964 Remote Similarity NPD8150 Discontinued
0.6957 Remote Similarity NPD3972 Approved
0.695 Remote Similarity NPD5736 Approved
0.6948 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6942 Remote Similarity NPD7631 Approved
0.6937 Remote Similarity NPD6959 Discontinued
0.6929 Remote Similarity NPD164 Approved
0.6929 Remote Similarity NPD1237 Approved
0.6923 Remote Similarity NPD3021 Approved
0.6923 Remote Similarity NPD3022 Approved
0.6911 Remote Similarity NPD2859 Approved
0.6911 Remote Similarity NPD2860 Approved
0.6908 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6905 Remote Similarity NPD1932 Approved
0.6903 Remote Similarity NPD4380 Phase 2
0.6901 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6901 Remote Similarity NPD6832 Phase 2
0.6897 Remote Similarity NPD1899 Clinical (unspecified phase)
0.688 Remote Similarity NPD2066 Phase 3
0.6875 Remote Similarity NPD520 Approved
0.6871 Remote Similarity NPD4308 Phase 3
0.6864 Remote Similarity NPD5037 Approved
0.6864 Remote Similarity NPD5038 Approved
0.6861 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6846 Remote Similarity NPD1549 Phase 2
0.6842 Remote Similarity NPD1511 Approved
0.6838 Remote Similarity NPD3091 Approved
0.6838 Remote Similarity NPD9545 Approved
0.6835 Remote Similarity NPD5402 Approved
0.6835 Remote Similarity NPD9269 Phase 2
0.6829 Remote Similarity NPD2934 Approved
0.6829 Remote Similarity NPD2933 Approved
0.6829 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6824 Remote Similarity NPD1551 Phase 2
0.6815 Remote Similarity NPD1934 Approved
0.6812 Remote Similarity NPD3496 Discontinued
0.6809 Remote Similarity NPD2797 Approved
0.6807 Remote Similarity NPD650 Approved
0.6806 Remote Similarity NPD3268 Approved
0.6805 Remote Similarity NPD5036 Approved
0.68 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6792 Remote Similarity NPD3882 Suspended
0.6788 Remote Similarity NPD9268 Approved
0.6788 Remote Similarity NPD5691 Approved
0.6786 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6786 Remote Similarity NPD8313 Approved
0.6786 Remote Similarity NPD8312 Approved
0.6784 Remote Similarity NPD6836 Approved
0.6779 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6779 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6774 Remote Similarity NPD1809 Phase 2
0.677 Remote Similarity NPD5494 Approved
0.6763 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6763 Remote Similarity NPD1281 Approved
0.6763 Remote Similarity NPD1611 Approved
0.6763 Remote Similarity NPD6212 Phase 3
0.6763 Remote Similarity NPD6213 Phase 3
0.6757 Remote Similarity NPD3748 Approved
0.6753 Remote Similarity NPD1512 Approved
0.6753 Remote Similarity NPD6273 Approved
0.675 Remote Similarity NPD3749 Approved
0.6748 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6742 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6739 Remote Similarity NPD4059 Approved
0.6738 Remote Similarity NPD6696 Suspended
0.6736 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6735 Remote Similarity NPD6651 Approved
0.6731 Remote Similarity NPD7458 Discontinued
0.673 Remote Similarity NPD2296 Approved
0.673 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6724 Remote Similarity NPD6534 Approved
0.6724 Remote Similarity NPD6535 Approved
0.6718 Remote Similarity NPD2329 Discontinued
0.6716 Remote Similarity NPD1241 Discontinued
0.6716 Remote Similarity NPD1398 Phase 1
0.6713 Remote Similarity NPD9494 Approved
0.6712 Remote Similarity NPD2979 Phase 3
0.6711 Remote Similarity NPD2796 Approved
0.6711 Remote Similarity NPD6099 Approved
0.6711 Remote Similarity NPD6100 Approved
0.6691 Remote Similarity NPD4879 Approved
0.6691 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6691 Remote Similarity NPD7340 Approved
0.669 Remote Similarity NPD1699 Clinical (unspecified phase)
0.669 Remote Similarity NPD3094 Phase 2
0.6687 Remote Similarity NPD5711 Approved
0.6687 Remote Similarity NPD5710 Approved
0.6687 Remote Similarity NPD7768 Phase 2
0.6687 Remote Similarity NPD5844 Phase 1
0.6667 Remote Similarity NPD5033 Approved
0.6667 Remote Similarity NPD230 Phase 1
0.6667 Remote Similarity NPD1792 Phase 2

  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