Structure

Physi-Chem Properties

Molecular Weight:  288.1
Volume:  293.675
LogP:  4.519
LogD:  2.936
LogS:  -3.46
# Rotatable Bonds:  3
TPSA:  97.99
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.395
Synthetic Accessibility Score:  2.925
Fsp3:  0.188
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:  -4.909
MDCK Permeability:  8.318387699546292e-06
Pgp-inhibitor:  0.01
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.847
30% Bioavailability (F30%):  0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.005
Plasma Protein Binding (PPB):  96.12079620361328%
Volume Distribution (VD):  0.681
Pgp-substrate:  5.406493186950684%

ADMET: Metabolism

CYP1A2-inhibitor:  0.953
CYP1A2-substrate:  0.173
CYP2C19-inhibitor:  0.259
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.719
CYP2C9-substrate:  0.741
CYP2D6-inhibitor:  0.716
CYP2D6-substrate:  0.235
CYP3A4-inhibitor:  0.149
CYP3A4-substrate:  0.096

ADMET: Excretion

Clearance (CL):  17.16
Half-life (T1/2):  0.783

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.264
Drug-inuced Liver Injury (DILI):  0.805
AMES Toxicity:  0.766
Rat Oral Acute Toxicity:  0.442
Maximum Recommended Daily Dose:  0.294
Skin Sensitization:  0.922
Carcinogencity:  0.454
Eye Corrosion:  0.033
Eye Irritation:  0.942
Respiratory Toxicity:  0.401

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  Natural Product: NPC242358

Natural Product ID:  NPC242358
Common Name*:   5,8-Dihydroxy-2-(1-Hydroxy-4-Methylpent-3-Enyl)Naphthalene-1,4-Dione
IUPAC Name:   5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
Synonyms:  
Standard InCHIKey:  NEZONWMXZKDMKF-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3
SMILES:  CC(=CCC(C1=CC(=O)c2c(C1=O)c(O)ccc2O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL29285
PubChem CID:   5208
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]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[17157006]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[19217780]
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]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8642 Lithospermum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30958 Onosma paniculatum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
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]
NPO8642 Lithospermum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8642 Lithospermum officinale 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]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30958 Onosma paniculatum Species Boraginaceae 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]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae 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]
NPO8642 Lithospermum officinale 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]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20297 Arnebia guttata 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 663.74 nM PMID[523072]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 805.38 nM PMID[523072]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 1132.4 nM PMID[523072]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 524.81 nM PMID[523072]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 1377.21 nM PMID[523072]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 641.21 nM PMID[523072]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 34.91 nM PMID[523072]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 1610.65 nM PMID[523072]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 1221.8 nM PMID[523072]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 300.61 nM PMID[523072]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 1963.36 nM PMID[523072]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 190.55 nM PMID[523072]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 1142.88 nM PMID[523072]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 62.95 nM PMID[523072]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 1823.9 nM PMID[523072]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 2046.44 nM PMID[523072]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 2103.78 nM PMID[523072]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 1548.82 nM PMID[523072]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 1972.42 nM PMID[523072]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 2360.48 nM PMID[523072]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 1552.39 nM PMID[523072]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 149.62 nM PMID[523072]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 1534.62 nM PMID[523072]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 933.25 nM PMID[523072]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 257.63 nM PMID[523072]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 4698.94 nM PMID[523072]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 1156.11 nM PMID[523072]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 229.61 nM PMID[523072]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 2393.32 nM PMID[523072]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 1216.19 nM PMID[523072]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 1761.98 nM PMID[523072]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 1584.89 nM PMID[523072]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 1949.84 nM PMID[523072]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 4819.48 nM PMID[523072]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 5035.01 nM PMID[523072]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 1737.8 nM PMID[523072]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1247.38 nM PMID[523072]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 210.38 nM PMID[523072]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 2269.86 nM PMID[523072]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 1538.15 nM PMID[523072]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 557.19 nM PMID[523072]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 2233.57 nM PMID[523072]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 11668.1 nM PMID[523072]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 389.94 nM PMID[523072]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 1577.61 nM PMID[523072]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 1883.65 nM PMID[523072]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 407.38 nM PMID[523072]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 1306.17 nM PMID[523072]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 1640.59 nM PMID[523072]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 2779.71 nM PMID[523072]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 2904.02 nM PMID[523072]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 494.31 nM PMID[523072]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 1499.68 nM PMID[523072]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 74.99 nM PMID[523072]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 1006.93 nM PMID[523072]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 1972.42 nM PMID[523072]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 1482.52 nM PMID[523072]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 171.4 nM PMID[523072]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 744.73 nM PMID[523072]

☑ 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 NPC242358 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 NPC110609
1.0 High Similarity NPC246693
0.952 High Similarity NPC306765
0.9323 High Similarity NPC471602
0.9323 High Similarity NPC256463
0.9323 High Similarity NPC476477
0.9323 High Similarity NPC306835
0.9323 High Similarity NPC111422
0.9323 High Similarity NPC29771
0.9323 High Similarity NPC299405
0.9323 High Similarity NPC216312
0.9318 High Similarity NPC305060
0.9254 High Similarity NPC42262
0.9254 High Similarity NPC32749
0.9254 High Similarity NPC220496
0.9254 High Similarity NPC147542
0.9254 High Similarity NPC37992
0.9254 High Similarity NPC327916
0.9254 High Similarity NPC241349
0.9185 High Similarity NPC257003
0.9185 High Similarity NPC471444
0.9118 High Similarity NPC474300
0.9062 High Similarity NPC3224
0.9062 High Similarity NPC1991
0.9062 High Similarity NPC231774
0.9055 High Similarity NPC234890
0.9055 High Similarity NPC74507
0.9051 High Similarity NPC476473
0.9023 High Similarity NPC281513
0.9023 High Similarity NPC22222
0.9008 High Similarity NPC205992
0.9 High Similarity NPC278928
0.8992 High Similarity NPC471530
0.8986 High Similarity NPC89664
0.8986 High Similarity NPC274085
0.8986 High Similarity NPC477409
0.896 High Similarity NPC206778
0.896 High Similarity NPC285829
0.8955 High Similarity NPC272268
0.8939 High Similarity NPC70622
0.8915 High Similarity NPC136342
0.8915 High Similarity NPC295202
0.8915 High Similarity NPC49647
0.8915 High Similarity NPC96915
0.8915 High Similarity NPC227741
0.8906 High Similarity NPC310540
0.8906 High Similarity NPC68756
0.8906 High Similarity NPC152525
0.8898 High Similarity NPC307174
0.8897 High Similarity NPC295339
0.8889 High Similarity NPC245923
0.888 High Similarity NPC232178
0.8849 High Similarity NPC103910
0.8837 High Similarity NPC103540
0.8837 High Similarity NPC131799
0.8824 High Similarity NPC61590
0.8815 High Similarity NPC474813
0.8815 High Similarity NPC315275
0.881 High Similarity NPC7151
0.881 High Similarity NPC216297
0.881 High Similarity NPC473662
0.8797 High Similarity NPC58685
0.8788 High Similarity NPC136588
0.8788 High Similarity NPC199253
0.8779 High Similarity NPC237225
0.8779 High Similarity NPC282923
0.8768 High Similarity NPC187843
0.8759 High Similarity NPC477408
0.8741 High Similarity NPC283088
0.8731 High Similarity NPC115458
0.8731 High Similarity NPC314048
0.8722 High Similarity NPC85342
0.872 High Similarity NPC269414
0.8712 High Similarity NPC146647
0.8712 High Similarity NPC34414
0.8712 High Similarity NPC99731
0.8686 High Similarity NPC173980
0.8682 High Similarity NPC477153
0.8682 High Similarity NPC375356
0.8657 High Similarity NPC309430
0.8651 High Similarity NPC41567
0.8647 High Similarity NPC198305
0.8647 High Similarity NPC475741
0.8647 High Similarity NPC55949
0.8643 High Similarity NPC21873
0.864 High Similarity NPC108288
0.864 High Similarity NPC477453
0.8636 High Similarity NPC247250
0.8636 High Similarity NPC165257
0.8636 High Similarity NPC767
0.8636 High Similarity NPC48248
0.8633 High Similarity NPC124365
0.8626 High Similarity NPC51037
0.8623 High Similarity NPC103337
0.8623 High Similarity NPC114620
0.8605 High Similarity NPC300274
0.8593 High Similarity NPC52407
0.8592 High Similarity NPC300540
0.8582 High Similarity NPC29932
0.8582 High Similarity NPC244699
0.8582 High Similarity NPC17083
0.8571 High Similarity NPC135524
0.856 High Similarity NPC240163
0.855 High Similarity NPC240744
0.855 High Similarity NPC167055
0.854 High Similarity NPC155211
0.8519 High Similarity NPC477406
0.8519 High Similarity NPC88864
0.8511 High Similarity NPC143898
0.8507 High Similarity NPC31799
0.85 High Similarity NPC305845
0.85 High Similarity NPC204045
0.8485 Intermediate Similarity NPC472047
0.8473 Intermediate Similarity NPC173978
0.8473 Intermediate Similarity NPC142956
0.8467 Intermediate Similarity NPC161632
0.8462 Intermediate Similarity NPC136878
0.8456 Intermediate Similarity NPC254603
0.8456 Intermediate Similarity NPC53896
0.8456 Intermediate Similarity NPC171968
0.8456 Intermediate Similarity NPC193169
0.8451 Intermediate Similarity NPC244691
0.8451 Intermediate Similarity NPC471906
0.844 Intermediate Similarity NPC329493
0.844 Intermediate Similarity NPC474961
0.844 Intermediate Similarity NPC469520
0.8435 Intermediate Similarity NPC182921
0.8435 Intermediate Similarity NPC474824
0.8435 Intermediate Similarity NPC218870
0.8435 Intermediate Similarity NPC470408
0.8433 Intermediate Similarity NPC474546
0.8429 Intermediate Similarity NPC315578
0.8421 Intermediate Similarity NPC45537
0.8417 Intermediate Similarity NPC206207
0.8413 Intermediate Similarity NPC161304
0.8406 Intermediate Similarity NPC141934
0.8406 Intermediate Similarity NPC86524
0.8394 Intermediate Similarity NPC166480
0.8394 Intermediate Similarity NPC288089
0.8394 Intermediate Similarity NPC50924
0.8394 Intermediate Similarity NPC282780
0.8392 Intermediate Similarity NPC471683
0.8392 Intermediate Similarity NPC474630
0.8382 Intermediate Similarity NPC17843
0.837 Intermediate Similarity NPC31539
0.837 Intermediate Similarity NPC117609
0.837 Intermediate Similarity NPC147757
0.8357 Intermediate Similarity NPC1268
0.8357 Intermediate Similarity NPC138099
0.8357 Intermediate Similarity NPC143438
0.8357 Intermediate Similarity NPC242994
0.8357 Intermediate Similarity NPC26924
0.8357 Intermediate Similarity NPC190457
0.8346 Intermediate Similarity NPC71610
0.8345 Intermediate Similarity NPC147418
0.8345 Intermediate Similarity NPC94781
0.8333 Intermediate Similarity NPC285122
0.8322 Intermediate Similarity NPC474861
0.8321 Intermediate Similarity NPC213485
0.8321 Intermediate Similarity NPC225051
0.8321 Intermediate Similarity NPC139074
0.8321 Intermediate Similarity NPC40524
0.831 Intermediate Similarity NPC85310
0.831 Intermediate Similarity NPC137649
0.8309 Intermediate Similarity NPC205360
0.8308 Intermediate Similarity NPC472046
0.8298 Intermediate Similarity NPC183345
0.8298 Intermediate Similarity NPC169452
0.8298 Intermediate Similarity NPC181560
0.8288 Intermediate Similarity NPC44378
0.8288 Intermediate Similarity NPC280753
0.8288 Intermediate Similarity NPC120171
0.8286 Intermediate Similarity NPC13715
0.8284 Intermediate Similarity NPC470841
0.8273 Intermediate Similarity NPC472308
0.8273 Intermediate Similarity NPC193358
0.8271 Intermediate Similarity NPC472592
0.8264 Intermediate Similarity NPC34482
0.8264 Intermediate Similarity NPC170055
0.8261 Intermediate Similarity NPC474394
0.8261 Intermediate Similarity NPC287604
0.8261 Intermediate Similarity NPC202225
0.8261 Intermediate Similarity NPC44437
0.8261 Intermediate Similarity NPC472262
0.8261 Intermediate Similarity NPC12070
0.8261 Intermediate Similarity NPC161964
0.8258 Intermediate Similarity NPC275145
0.8258 Intermediate Similarity NPC135062
0.8252 Intermediate Similarity NPC471682
0.8248 Intermediate Similarity NPC478190
0.8239 Intermediate Similarity NPC91019
0.8239 Intermediate Similarity NPC283292
0.8239 Intermediate Similarity NPC106519
0.8235 Intermediate Similarity NPC123
0.8235 Intermediate Similarity NPC163169
0.8231 Intermediate Similarity NPC315520
0.8227 Intermediate Similarity NPC162939
0.8219 Intermediate Similarity NPC112816
0.8214 Intermediate Similarity NPC53414
0.8214 Intermediate Similarity NPC471905

  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 NPC242358 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
0.8837 High Similarity NPD1470 Approved
0.864 High Similarity NPD405 Clinical (unspecified phase)
0.8527 High Similarity NPD1201 Approved
0.8143 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD3300 Phase 2
0.7832 Intermediate Similarity NPD5406 Approved
0.7832 Intermediate Similarity NPD2935 Discontinued
0.7832 Intermediate Similarity NPD5404 Approved
0.7832 Intermediate Similarity NPD5405 Approved
0.7832 Intermediate Similarity NPD5408 Approved
0.777 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD7390 Discontinued
0.7682 Intermediate Similarity NPD3226 Approved
0.7655 Intermediate Similarity NPD2346 Discontinued
0.7639 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD943 Approved
0.7556 Intermediate Similarity NPD2932 Approved
0.75 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD3019 Approved
0.7417 Intermediate Similarity NPD2532 Approved
0.7417 Intermediate Similarity NPD2534 Approved
0.7417 Intermediate Similarity NPD2533 Approved
0.7388 Intermediate Similarity NPD9493 Approved
0.7357 Intermediate Similarity NPD1164 Approved
0.7353 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD7635 Approved
0.7328 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD8150 Discontinued
0.7308 Intermediate Similarity NPD74 Approved
0.7308 Intermediate Similarity NPD9266 Approved
0.7305 Intermediate Similarity NPD2798 Approved
0.729 Intermediate Similarity NPD4380 Phase 2
0.7289 Intermediate Similarity NPD4955 Approved
0.7289 Intermediate Similarity NPD36 Approved
0.7289 Intermediate Similarity NPD5034 Approved
0.7289 Intermediate Similarity NPD4954 Approved
0.7289 Intermediate Similarity NPD5028 Approved
0.7289 Intermediate Similarity NPD5026 Approved
0.7279 Intermediate Similarity NPD2799 Discontinued
0.7279 Intermediate Similarity NPD1510 Phase 2
0.7279 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD6232 Discontinued
0.7261 Intermediate Similarity NPD7819 Suspended
0.7261 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD1607 Approved
0.7251 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD1240 Approved
0.7239 Intermediate Similarity NPD7473 Discontinued
0.7235 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD9267 Approved
0.7231 Intermediate Similarity NPD9263 Approved
0.7231 Intermediate Similarity NPD9264 Approved
0.7229 Intermediate Similarity NPD5030 Phase 2
0.7222 Intermediate Similarity NPD2313 Discontinued
0.7222 Intermediate Similarity NPD3764 Approved
0.7219 Intermediate Similarity NPD5038 Approved
0.7219 Intermediate Similarity NPD5037 Approved
0.7215 Intermediate Similarity NPD5402 Approved
0.7205 Intermediate Similarity NPD6959 Discontinued
0.7197 Intermediate Similarity NPD6844 Discontinued
0.719 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD2344 Approved
0.7165 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5036 Approved
0.7152 Intermediate Similarity NPD2801 Approved
0.7143 Intermediate Similarity NPD8313 Approved
0.7143 Intermediate Similarity NPD8312 Approved
0.7133 Intermediate Similarity NPD1549 Phase 2
0.7132 Intermediate Similarity NPD1237 Approved
0.7121 Intermediate Similarity NPD4750 Phase 3
0.7115 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1934 Approved
0.7071 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD6535 Approved
0.7069 Intermediate Similarity NPD6534 Approved
0.7067 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD6663 Approved
0.7048 Intermediate Similarity NPD5844 Phase 1
0.7045 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD8166 Discontinued
0.7039 Intermediate Similarity NPD3750 Approved
0.7039 Intermediate Similarity NPD4628 Phase 3
0.7037 Intermediate Similarity NPD5494 Approved
0.7029 Intermediate Similarity NPD3091 Approved
0.7029 Intermediate Similarity NPD9545 Approved
0.7024 Intermediate Similarity NPD5027 Approved
0.7024 Intermediate Similarity NPD5031 Approved
0.7024 Intermediate Similarity NPD5029 Approved
0.7014 Intermediate Similarity NPD5736 Approved
0.7011 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6212 Phase 3
0.7011 Intermediate Similarity NPD6213 Phase 3
0.7 Intermediate Similarity NPD1551 Phase 2
0.7 Intermediate Similarity NPD3023 Approved
0.7 Intermediate Similarity NPD2796 Approved
0.7 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3026 Approved
0.6993 Remote Similarity NPD3094 Phase 2
0.6993 Remote Similarity NPD2309 Approved
0.6986 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6985 Remote Similarity NPD5951 Approved
0.6985 Remote Similarity NPD9281 Approved
0.6984 Remote Similarity NPD844 Approved
0.6978 Remote Similarity NPD3024 Approved
0.6978 Remote Similarity NPD3025 Approved
0.6974 Remote Similarity NPD2800 Approved
0.6974 Remote Similarity NPD7421 Clinical (unspecified phase)
0.697 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6777 Approved
0.6966 Remote Similarity NPD6779 Approved
0.6966 Remote Similarity NPD6781 Approved
0.6966 Remote Similarity NPD6776 Approved
0.6966 Remote Similarity NPD6778 Approved
0.6966 Remote Similarity NPD6782 Approved
0.6966 Remote Similarity NPD6780 Approved
0.6959 Remote Similarity NPD447 Suspended
0.6957 Remote Similarity NPD3882 Suspended
0.6954 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6954 Remote Similarity NPD1471 Phase 3
0.695 Remote Similarity NPD3092 Approved
0.6949 Remote Similarity NPD7700 Phase 2
0.6949 Remote Similarity NPD7699 Phase 2
0.6944 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6929 Remote Similarity NPD288 Approved
0.6929 Remote Similarity NPD4626 Approved
0.6928 Remote Similarity NPD3400 Discontinued
0.6928 Remote Similarity NPD7003 Approved
0.6928 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6273 Approved
0.6923 Remote Similarity NPD1876 Approved
0.6923 Remote Similarity NPD9261 Approved
0.6923 Remote Similarity NPD6559 Discontinued
0.6917 Remote Similarity NPD2182 Approved
0.6914 Remote Similarity NPD7075 Discontinued
0.6914 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6901 Remote Similarity NPD9717 Approved
0.6886 Remote Similarity NPD3818 Discontinued
0.6875 Remote Similarity NPD1203 Approved
0.6871 Remote Similarity NPD411 Approved
0.6867 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6867 Remote Similarity NPD6166 Phase 2
0.6867 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6859 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6857 Remote Similarity NPD1651 Approved
0.6852 Remote Similarity NPD7768 Phase 2
0.6851 Remote Similarity NPD7435 Discontinued
0.6851 Remote Similarity NPD7698 Approved
0.6851 Remote Similarity NPD7697 Approved
0.6851 Remote Similarity NPD7696 Phase 3
0.6849 Remote Similarity NPD6832 Phase 2
0.6848 Remote Similarity NPD5711 Approved
0.6848 Remote Similarity NPD5710 Approved
0.6846 Remote Similarity NPD230 Phase 1
0.6846 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5035 Approved
0.6842 Remote Similarity NPD2342 Discontinued
0.6832 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5039 Approved
0.6824 Remote Similarity NPD520 Approved
0.6821 Remote Similarity NPD8434 Phase 2
0.6815 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6813 Remote Similarity NPD7411 Suspended
0.6813 Remote Similarity NPD7870 Phase 2
0.6813 Remote Similarity NPD7871 Phase 2
0.6809 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6809 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6809 Remote Similarity NPD3095 Discontinued
0.6806 Remote Similarity NPD1283 Approved
0.68 Remote Similarity NPD6651 Approved
0.6796 Remote Similarity NPD6823 Phase 2
0.6795 Remote Similarity NPD1511 Approved
0.6792 Remote Similarity NPD2651 Approved
0.6792 Remote Similarity NPD2649 Approved
0.6786 Remote Similarity NPD3751 Discontinued
0.6783 Remote Similarity NPD3972 Approved
0.6783 Remote Similarity NPD4878 Approved
0.6783 Remote Similarity NPD9269 Phase 2
0.6774 Remote Similarity NPD6190 Approved
0.6772 Remote Similarity NPD5403 Approved
0.677 Remote Similarity NPD6801 Discontinued
0.6765 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6761 Remote Similarity NPD3496 Discontinued
0.675 Remote Similarity NPD6599 Discontinued
0.6743 Remote Similarity NPD6836 Approved
0.6742 Remote Similarity NPD164 Approved
0.6739 Remote Similarity NPD497 Approved
0.6738 Remote Similarity NPD5691 Approved
0.6738 Remote Similarity NPD9268 Approved
0.6736 Remote Similarity NPD1755 Approved
0.6712 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6711 Remote Similarity NPD3748 Approved
0.6709 Remote Similarity NPD1512 Approved
0.6707 Remote Similarity NPD3749 Approved
0.6706 Remote Similarity NPD7074 Phase 3
0.6706 Remote Similarity NPD4956 Approved
0.6703 Remote Similarity NPD7701 Phase 2
0.6693 Remote Similarity NPD845 Approved
0.6692 Remote Similarity NPD3020 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