Structure

Physi-Chem Properties

Molecular Weight:  486.37
Volume:  537.758
LogP:  4.773
LogD:  3.686
LogS:  -4.274
# Rotatable Bonds:  6
TPSA:  77.76
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.357
Synthetic Accessibility Score:  4.941
Fsp3:  0.839
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:  -5.338
MDCK Permeability:  1.1475976862129755e-05
Pgp-inhibitor:  0.384
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.137
30% Bioavailability (F30%):  0.153

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.032
Plasma Protein Binding (PPB):  88.91313934326172%
Volume Distribution (VD):  0.844
Pgp-substrate:  2.139738082885742%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.512
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.944
CYP2C9-inhibitor:  0.168
CYP2C9-substrate:  0.959
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.726
CYP3A4-inhibitor:  0.038
CYP3A4-substrate:  0.148

ADMET: Excretion

Clearance (CL):  3.274
Half-life (T1/2):  0.139

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.225
Drug-inuced Liver Injury (DILI):  0.027
AMES Toxicity:  0.018
Rat Oral Acute Toxicity:  0.044
Maximum Recommended Daily Dose:  0.849
Skin Sensitization:  0.048
Carcinogencity:  0.017
Eye Corrosion:  0.005
Eye Irritation:  0.133
Respiratory Toxicity:  0.916

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC46940

Natural Product ID:  NPC46940
Common Name*:   5-Ethenyl-1,6-Dimethyl-9,10-Dihydrophenanthrene-2,7-Diol
IUPAC Name:   5-ethenyl-1,6-dimethyl-9,10-dihydrophenanthrene-2,7-diol
Synonyms:   NSC-220968
Standard InCHIKey:  XNVMKPYDOHZJLR-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H18O2/c1-4-13-10(2)17(20)9-12-5-6-14-11(3)16(19)8-7-15(14)18(12)13/h4,7-9,19-20H,1,5-6H2,2-3H3
SMILES:  C=Cc1c(C)c(O)cc2c1c1ccc(c(c1CC2)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL38650
PubChem CID:   72740
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000025] Phenanthrenes and derivatives
        • [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO23964 Haloxylon scoparium Species Chenopodiaceae Eukaryota n.a. n.a. n.a. PMID[20210326]
NPO40173 Juncus inflexus Species Juncaceae Eukaryota n.a. n.a. n.a. PMID[27808510]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. PMID[30892891]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO21045 Salvia staminea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25816 Kopsia flavida Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21045 Salvia staminea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30493 Common rush n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23964 Haloxylon scoparium Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23592 Oecophylla longinoda Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3850 Ilex argentina Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21045 Salvia staminea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19288 Rhynchosia minima Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25816 Kopsia flavida Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22843 Astraea lobata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22164 Vanillosmopsis erythropappa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23551 Paullinia japonica Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20333 Guatteria sagotiana Species Annonaceae 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
NPT319 Cell Line B16 Mus musculus IC50 = 12.5 ug.mL-1 PMID[549804]
NPT137 Cell Line L1210 Mus musculus IC50 = 13.8 ug.mL-1 PMID[549804]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 13645.83 nM PMID[549806]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 17538.81 nM PMID[549806]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 17139.57 nM PMID[549806]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 29444.22 nM PMID[549806]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 14825.18 nM PMID[549806]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 23173.95 nM PMID[549806]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 14996.85 nM PMID[549806]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 13489.63 nM PMID[549806]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 14092.89 nM PMID[549806]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 15995.58 nM PMID[549806]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 19633.6 nM PMID[549806]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 11641.26 nM PMID[549806]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 25763.21 nM PMID[549806]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 11641.26 nM PMID[549806]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 26668.59 nM PMID[549806]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 20989.4 nM PMID[549806]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 14256.08 nM PMID[549806]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 17498.47 nM PMID[549806]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 27227.01 nM PMID[549806]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 24490.63 nM PMID[549806]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 23227.37 nM PMID[549806]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 3706.81 nM PMID[549806]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 13061.71 nM PMID[549806]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 23442.29 nM PMID[549806]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 19408.86 nM PMID[549806]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 14321.88 nM PMID[549806]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 20892.96 nM PMID[549806]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 22387.21 nM PMID[549806]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 15885.47 nM PMID[549806]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 17139.57 nM PMID[549806]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 19453.6 nM PMID[549806]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 16069.41 nM PMID[549806]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 17139.57 nM PMID[549806]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 18967.06 nM PMID[549806]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 18967.06 nM PMID[549806]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 12246.16 nM PMID[549806]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 14092.89 nM PMID[549806]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 18535.32 nM PMID[549806]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 1967.89 nM PMID[549806]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 20892.96 nM PMID[549806]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 10000.0 nM PMID[549806]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 10914.4 nM PMID[549806]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 17021.59 nM PMID[549806]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 7498.94 nM PMID[549806]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 20137.24 nM PMID[549806]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 13899.53 nM PMID[549806]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 14092.89 nM PMID[549806]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 16595.87 nM PMID[549806]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 14859.36 nM PMID[549806]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 3111.72 nM PMID[549806]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 15848.93 nM PMID[549806]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 14791.08 nM PMID[549806]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 12473.84 nM PMID[549806]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 17258.38 nM PMID[549806]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 23659.2 nM PMID[549806]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 16218.1 nM PMID[549806]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 19275.25 nM PMID[549806]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 10864.26 nM PMID[549806]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 25.0 ug.mL-1 PMID[549804]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 12.5 ug.mL-1 PMID[549804]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Ratio = 7.0 n.a. PMID[549807]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 25.0 ug.mL-1 PMID[549807]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 12.0 mm PMID[549807]
NPT669 Individual Protein Solute carrier family 22 member 8 Homo sapiens Inhibition > 50.0 % PMID[549808]
NPT665 Individual Protein Solute carrier family 22 member 6 Homo sapiens Inhibition < 50.0 % PMID[549808]
NPT669 Individual Protein Solute carrier family 22 member 8 Homo sapiens IC50 = 6500.0 nM PMID[549808]

☑ 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 NPC46940 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
0.9904 High Similarity NPC95716
0.9717 High Similarity NPC715
0.9626 High Similarity NPC195922
0.9524 High Similarity NPC58865
0.9524 High Similarity NPC314187
0.9429 High Similarity NPC11554
0.9364 High Similarity NPC299180
0.9352 High Similarity NPC322239
0.9346 High Similarity NPC176279
0.9346 High Similarity NPC151537
0.9346 High Similarity NPC260323
0.9333 High Similarity NPC151477
0.9259 High Similarity NPC250323
0.9252 High Similarity NPC141782
0.9231 High Similarity NPC238696
0.9182 High Similarity NPC35797
0.9182 High Similarity NPC192948
0.9143 High Similarity NPC138942
0.9143 High Similarity NPC117115
0.9135 High Similarity NPC168829
0.9099 High Similarity NPC477137
0.9099 High Similarity NPC471668
0.9099 High Similarity NPC219112
0.9099 High Similarity NPC38893
0.9099 High Similarity NPC308311
0.9091 High Similarity NPC249270
0.9091 High Similarity NPC268160
0.9074 High Similarity NPC296683
0.9074 High Similarity NPC13482
0.9057 High Similarity NPC271274
0.9057 High Similarity NPC21594
0.9048 High Similarity NPC288411
0.9043 High Similarity NPC176208
0.9027 High Similarity NPC176893
0.9018 High Similarity NPC477136
0.9018 High Similarity NPC304510
0.9018 High Similarity NPC172219
0.9009 High Similarity NPC147179
0.9 High Similarity NPC321589
0.8947 High Similarity NPC103916
0.8938 High Similarity NPC471671
0.8929 High Similarity NPC308828
0.8929 High Similarity NPC469663
0.8929 High Similarity NPC261973
0.8929 High Similarity NPC92
0.8919 High Similarity NPC107240
0.8899 High Similarity NPC132720
0.8879 High Similarity NPC54765
0.886 High Similarity NPC469644
0.886 High Similarity NPC151197
0.886 High Similarity NPC93071
0.886 High Similarity NPC126002
0.885 High Similarity NPC16030
0.8839 High Similarity NPC246760
0.8839 High Similarity NPC84999
0.8839 High Similarity NPC469719
0.8829 High Similarity NPC117846
0.8829 High Similarity NPC317869
0.8818 High Similarity NPC77772
0.8818 High Similarity NPC322753
0.8772 High Similarity NPC469609
0.875 High Similarity NPC32674
0.875 High Similarity NPC156313
0.8739 High Similarity NPC471179
0.8729 High Similarity NPC224342
0.8718 High Similarity NPC71094
0.8716 High Similarity NPC262365
0.8716 High Similarity NPC95344
0.8707 High Similarity NPC129176
0.8707 High Similarity NPC32322
0.8707 High Similarity NPC259703
0.8692 High Similarity NPC272029
0.8684 High Similarity NPC470760
0.8679 High Similarity NPC51015
0.8661 High Similarity NPC263753
0.8649 High Similarity NPC165770
0.8649 High Similarity NPC225679
0.8649 High Similarity NPC4493
0.8649 High Similarity NPC476632
0.8649 High Similarity NPC266937
0.8649 High Similarity NPC470770
0.8632 High Similarity NPC162935
0.8632 High Similarity NPC249340
0.8621 High Similarity NPC135467
0.8621 High Similarity NPC260832
0.8609 High Similarity NPC154030
0.8598 High Similarity NPC233827
0.8598 High Similarity NPC168393
0.8596 High Similarity NPC115808
0.8596 High Similarity NPC141001
0.8585 High Similarity NPC72729
0.8585 High Similarity NPC211885
0.8585 High Similarity NPC225506
0.8584 High Similarity NPC471534
0.8571 High Similarity NPC77492
0.8571 High Similarity NPC302371
0.8571 High Similarity NPC43525
0.8571 High Similarity NPC166995
0.8571 High Similarity NPC177962
0.8571 High Similarity NPC228425
0.8571 High Similarity NPC79241
0.8571 High Similarity NPC6597
0.8571 High Similarity NPC62867
0.8559 High Similarity NPC224870
0.8559 High Similarity NPC44732
0.8559 High Similarity NPC297057
0.8559 High Similarity NPC11250
0.8558 High Similarity NPC274678
0.8558 High Similarity NPC26244
0.8547 High Similarity NPC241001
0.8545 High Similarity NPC233835
0.8525 High Similarity NPC276238
0.8522 High Similarity NPC25648
0.8519 High Similarity NPC254965
0.8519 High Similarity NPC327811
0.8505 High Similarity NPC252105
0.8496 Intermediate Similarity NPC141003
0.8496 Intermediate Similarity NPC35344
0.8491 Intermediate Similarity NPC122005
0.8491 Intermediate Similarity NPC252821
0.8491 Intermediate Similarity NPC33675
0.8491 Intermediate Similarity NPC92730
0.8491 Intermediate Similarity NPC299762
0.8487 Intermediate Similarity NPC471187
0.8482 Intermediate Similarity NPC308689
0.8482 Intermediate Similarity NPC224527
0.8482 Intermediate Similarity NPC469912
0.8476 Intermediate Similarity NPC216520
0.8476 Intermediate Similarity NPC312132
0.8476 Intermediate Similarity NPC132271
0.8476 Intermediate Similarity NPC292730
0.8476 Intermediate Similarity NPC82664
0.8476 Intermediate Similarity NPC259512
0.8476 Intermediate Similarity NPC473388
0.8475 Intermediate Similarity NPC253627
0.8475 Intermediate Similarity NPC154696
0.8468 Intermediate Similarity NPC19808
0.8468 Intermediate Similarity NPC202647
0.8468 Intermediate Similarity NPC33728
0.8462 Intermediate Similarity NPC128062
0.8462 Intermediate Similarity NPC478121
0.8462 Intermediate Similarity NPC245187
0.8462 Intermediate Similarity NPC151715
0.8462 Intermediate Similarity NPC76938
0.8455 Intermediate Similarity NPC320439
0.8448 Intermediate Similarity NPC63010
0.8448 Intermediate Similarity NPC206
0.8448 Intermediate Similarity NPC328694
0.8448 Intermediate Similarity NPC164649
0.8448 Intermediate Similarity NPC48342
0.8443 Intermediate Similarity NPC215300
0.8443 Intermediate Similarity NPC96024
0.844 Intermediate Similarity NPC47284
0.844 Intermediate Similarity NPC99557
0.844 Intermediate Similarity NPC219286
0.843 Intermediate Similarity NPC170485
0.8426 Intermediate Similarity NPC108497
0.8421 Intermediate Similarity NPC12656
0.8417 Intermediate Similarity NPC61685
0.8417 Intermediate Similarity NPC181334
0.8407 Intermediate Similarity NPC286222
0.8407 Intermediate Similarity NPC228988
0.8403 Intermediate Similarity NPC121168
0.8403 Intermediate Similarity NPC471794
0.8396 Intermediate Similarity NPC225464
0.839 Intermediate Similarity NPC328504
0.8381 Intermediate Similarity NPC32714
0.8381 Intermediate Similarity NPC8392
0.8378 Intermediate Similarity NPC61885
0.8378 Intermediate Similarity NPC174981
0.8378 Intermediate Similarity NPC63698
0.8376 Intermediate Similarity NPC42657
0.8365 Intermediate Similarity NPC271440
0.8364 Intermediate Similarity NPC53740
0.8364 Intermediate Similarity NPC67250
0.8361 Intermediate Similarity NPC53781
0.8349 Intermediate Similarity NPC475225
0.8348 Intermediate Similarity NPC474486
0.8347 Intermediate Similarity NPC137750
0.8347 Intermediate Similarity NPC105031
0.8333 Intermediate Similarity NPC12221
0.8333 Intermediate Similarity NPC477685
0.8333 Intermediate Similarity NPC12824
0.8333 Intermediate Similarity NPC198014
0.8319 Intermediate Similarity NPC39029
0.8319 Intermediate Similarity NPC237667
0.8318 Intermediate Similarity NPC128723
0.8305 Intermediate Similarity NPC475245
0.8305 Intermediate Similarity NPC190501
0.8305 Intermediate Similarity NPC99734
0.8305 Intermediate Similarity NPC69006
0.8305 Intermediate Similarity NPC318552
0.8304 Intermediate Similarity NPC254833
0.8304 Intermediate Similarity NPC228343
0.8293 Intermediate Similarity NPC48248
0.8293 Intermediate Similarity NPC38017
0.8279 Intermediate Similarity NPC100414
0.8279 Intermediate Similarity NPC321822
0.8279 Intermediate Similarity NPC325294
0.8279 Intermediate Similarity NPC43000

  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 NPC46940 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
0.9333 High Similarity NPD2342 Discontinued
0.9083 High Similarity NPD7635 Approved
0.8667 High Similarity NPD3020 Approved
0.8621 High Similarity NPD2286 Discontinued
0.8558 High Similarity NPD844 Approved
0.8558 High Similarity NPD2859 Approved
0.8558 High Similarity NPD2860 Approved
0.8476 Intermediate Similarity NPD288 Approved
0.8462 Intermediate Similarity NPD2933 Approved
0.8462 Intermediate Similarity NPD2934 Approved
0.8448 Intermediate Similarity NPD3091 Approved
0.8305 Intermediate Similarity NPD3019 Approved
0.8305 Intermediate Similarity NPD4059 Approved
0.8304 Intermediate Similarity NPD3022 Approved
0.8304 Intermediate Similarity NPD3021 Approved
0.822 Intermediate Similarity NPD4093 Discontinued
0.8208 Intermediate Similarity NPD1809 Phase 2
0.819 Intermediate Similarity NPD845 Approved
0.8182 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.8167 Intermediate Similarity NPD3092 Approved
0.8151 Intermediate Similarity NPD2932 Approved
0.8142 Intermediate Similarity NPD4750 Phase 3
0.8113 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.8103 Intermediate Similarity NPD497 Approved
0.808 Intermediate Similarity NPD4625 Phase 3
0.8073 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.8017 Intermediate Similarity NPD498 Approved
0.8017 Intermediate Similarity NPD495 Approved
0.8017 Intermediate Similarity NPD496 Approved
0.8 Intermediate Similarity NPD4626 Approved
0.8 Intermediate Similarity NPD3095 Discontinued
0.7966 Intermediate Similarity NPD7325 Clinical (unspecified phase)
0.7903 Intermediate Similarity NPD3094 Phase 2
0.7869 Intermediate Similarity NPD1201 Approved
0.7863 Intermediate Similarity NPD4869 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD940 Approved
0.7838 Intermediate Similarity NPD846 Approved
0.7778 Intermediate Similarity NPD5736 Approved
0.7769 Intermediate Similarity NPD4097 Suspended
0.7769 Intermediate Similarity NPD1651 Approved
0.7768 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD4339 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD1242 Phase 1
0.7727 Intermediate Similarity NPD5406 Approved
0.7727 Intermediate Similarity NPD5408 Approved
0.7727 Intermediate Similarity NPD5404 Approved
0.7727 Intermediate Similarity NPD5405 Approved
0.7705 Intermediate Similarity NPD4589 Approved
0.7705 Intermediate Similarity NPD1751 Approved
0.7686 Intermediate Similarity NPD5304 Approved
0.7686 Intermediate Similarity NPD5303 Approved
0.768 Intermediate Similarity NPD1283 Approved
0.7672 Intermediate Similarity NPD1792 Phase 2
0.7656 Intermediate Similarity NPD5155 Approved
0.7656 Intermediate Similarity NPD5156 Approved
0.7642 Intermediate Similarity NPD3026 Approved
0.7642 Intermediate Similarity NPD3023 Approved
0.7623 Intermediate Similarity NPD3025 Approved
0.7623 Intermediate Similarity NPD3024 Approved
0.7623 Intermediate Similarity NPD5691 Approved
0.7619 Intermediate Similarity NPD1470 Approved
0.7615 Intermediate Similarity NPD4060 Phase 1
0.7596 Intermediate Similarity NPD111 Approved
0.7578 Intermediate Similarity NPD2605 Approved
0.7578 Intermediate Similarity NPD2606 Approved
0.7563 Intermediate Similarity NPD2228 Approved
0.7563 Intermediate Similarity NPD2234 Approved
0.7563 Intermediate Similarity NPD2229 Approved
0.7559 Intermediate Similarity NPD4624 Approved
0.7542 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7541 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD6663 Approved
0.7519 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3635 Approved
0.75 Intermediate Similarity NPD3636 Approved
0.75 Intermediate Similarity NPD3637 Approved
0.7464 Intermediate Similarity NPD7390 Discontinued
0.7464 Intermediate Similarity NPD2420 Approved
0.7464 Intermediate Similarity NPD2421 Approved
0.7462 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.746 Intermediate Similarity NPD1669 Approved
0.7442 Intermediate Similarity NPD3594 Approved
0.7442 Intermediate Similarity NPD3595 Approved
0.744 Intermediate Similarity NPD1281 Approved
0.744 Intermediate Similarity NPD1611 Approved
0.7438 Intermediate Similarity NPD709 Approved
0.7438 Intermediate Similarity NPD6671 Approved
0.7434 Intermediate Similarity NPD3028 Approved
0.7422 Intermediate Similarity NPD2195 Approved
0.7422 Intermediate Similarity NPD2194 Approved
0.7417 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD1398 Phase 1
0.7414 Intermediate Similarity NPD1444 Approved
0.7414 Intermediate Similarity NPD1445 Approved
0.7402 Intermediate Similarity NPD6696 Suspended
0.7377 Intermediate Similarity NPD7340 Approved
0.7372 Intermediate Similarity NPD7003 Approved
0.7364 Intermediate Similarity NPD2861 Phase 2
0.7348 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD3620 Phase 2
0.7323 Intermediate Similarity NPD5327 Phase 3
0.7323 Intermediate Similarity NPD4749 Approved
0.7313 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD4908 Phase 1
0.7299 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD6584 Phase 3
0.7286 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5283 Phase 1
0.7259 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD7743 Approved
0.7259 Intermediate Similarity NPD7742 Approved
0.7258 Intermediate Similarity NPD7330 Discontinued
0.7227 Intermediate Similarity NPD5451 Approved
0.7218 Intermediate Similarity NPD4140 Approved
0.7214 Intermediate Similarity NPD7041 Phase 2
0.7214 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD5951 Approved
0.7209 Intermediate Similarity NPD1164 Approved
0.7197 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD1610 Phase 2
0.7165 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD5735 Approved
0.7155 Intermediate Similarity NPD9500 Approved
0.7154 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD4725 Approved
0.7153 Intermediate Similarity NPD4726 Approved
0.7153 Intermediate Similarity NPD4721 Approved
0.7143 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD6353 Approved
0.7111 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD2230 Approved
0.7109 Intermediate Similarity NPD2233 Approved
0.7109 Intermediate Similarity NPD2232 Approved
0.7107 Intermediate Similarity NPD228 Approved
0.7101 Intermediate Similarity NPD7037 Approved
0.7097 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD2979 Phase 3
0.7087 Intermediate Similarity NPD1983 Approved
0.7087 Intermediate Similarity NPD1980 Approved
0.7087 Intermediate Similarity NPD1981 Approved
0.7073 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD4235 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6582 Phase 2
0.7054 Intermediate Similarity NPD6583 Phase 3
0.705 Intermediate Similarity NPD3638 Discontinued
0.7049 Intermediate Similarity NPD5535 Approved
0.7029 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD3845 Phase 1
0.7007 Intermediate Similarity NPD4108 Discontinued
0.6992 Remote Similarity NPD7095 Approved
0.6984 Remote Similarity NPD1548 Phase 1
0.6983 Remote Similarity NPD1616 Discontinued
0.6978 Remote Similarity NPD4257 Approved
0.6978 Remote Similarity NPD4256 Phase 2
0.6957 Remote Similarity NPD2935 Discontinued
0.6953 Remote Similarity NPD3143 Discontinued
0.695 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6949 Remote Similarity NPD9608 Approved
0.6949 Remote Similarity NPD9610 Approved
0.6947 Remote Similarity NPD3053 Approved
0.6947 Remote Similarity NPD3055 Approved
0.6947 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6947 Remote Similarity NPD4103 Phase 2
0.694 Remote Similarity NPD3764 Approved
0.6935 Remote Similarity NPD1793 Approved
0.6935 Remote Similarity NPD1791 Approved
0.6923 Remote Similarity NPD4659 Approved
0.6917 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6911 Remote Similarity NPD9379 Approved
0.6911 Remote Similarity NPD9377 Approved
0.6906 Remote Similarity NPD2346 Discontinued
0.6892 Remote Similarity NPD5929 Approved
0.6889 Remote Similarity NPD6405 Approved
0.6889 Remote Similarity NPD6407 Approved
0.6889 Remote Similarity NPD8032 Phase 2
0.688 Remote Similarity NPD6387 Discontinued
0.6879 Remote Similarity NPD8166 Discontinued
0.6875 Remote Similarity NPD4319 Phase 2
0.6875 Remote Similarity NPD2667 Approved
0.6875 Remote Similarity NPD2668 Approved
0.6875 Remote Similarity NPD7163 Clinical (unspecified phase)
0.687 Remote Similarity NPD5311 Approved
0.687 Remote Similarity NPD5310 Approved
0.6866 Remote Similarity NPD3027 Phase 3
0.6861 Remote Similarity NPD2157 Approved
0.686 Remote Similarity NPD2684 Approved
0.6849 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6846 Remote Similarity NPD3070 Discontinued
0.6842 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6835 Remote Similarity NPD2438 Suspended
0.6835 Remote Similarity NPD4476 Approved
0.6835 Remote Similarity NPD6100 Approved
0.6835 Remote Similarity NPD1632 Clinical (unspecified phase)
0.6835 Remote Similarity NPD4477 Approved
0.6835 Remote Similarity NPD2531 Phase 2
0.6835 Remote Similarity NPD6099 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