Structure

Physi-Chem Properties

Molecular Weight:  279.13
Volume:  295.78
LogP:  4.77
LogD:  4.134
LogS:  -3.749
# Rotatable Bonds:  0
TPSA:  45.25
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.635
Synthetic Accessibility Score:  2.868
Fsp3:  0.222
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -5.046
MDCK Permeability:  1.6245297956629656e-05
Pgp-inhibitor:  0.291
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.062
20% Bioavailability (F20%):  0.015
30% Bioavailability (F30%):  0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.4
Plasma Protein Binding (PPB):  98.393310546875%
Volume Distribution (VD):  0.739
Pgp-substrate:  1.2941311597824097%

ADMET: Metabolism

CYP1A2-inhibitor:  0.987
CYP1A2-substrate:  0.763
CYP2C19-inhibitor:  0.87
CYP2C19-substrate:  0.153
CYP2C9-inhibitor:  0.774
CYP2C9-substrate:  0.942
CYP2D6-inhibitor:  0.94
CYP2D6-substrate:  0.918
CYP3A4-inhibitor:  0.641
CYP3A4-substrate:  0.233

ADMET: Excretion

Clearance (CL):  4.698
Half-life (T1/2):  0.31

ADMET: Toxicity

hERG Blockers:  0.334
Human Hepatotoxicity (H-HT):  0.91
Drug-inuced Liver Injury (DILI):  0.759
AMES Toxicity:  0.846
Rat Oral Acute Toxicity:  0.941
Maximum Recommended Daily Dose:  0.928
Skin Sensitization:  0.897
Carcinogencity:  0.92
Eye Corrosion:  0.013
Eye Irritation:  0.962
Respiratory Toxicity:  0.977

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

  Natural Product: NPC48353

Natural Product ID:  NPC48353
Common Name*:   Glycoborinine
IUPAC Name:   3,3,10-trimethyl-7H-pyrano[3,2-g]carbazol-9-ol
Synonyms:   Glycoborinine
Standard InCHIKey:  KGHHJTRYOSFBOZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H17NO2/c1-10-8-12-14(9-15(10)20)19-13-4-5-16-11(17(12)13)6-7-18(2,3)21-16/h4-9,19-20H,1-3H3
SMILES:  Oc1cc2[nH]c3c(c2cc1C)c1C=CC(Oc1cc3)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL506671
PubChem CID:   10446329
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000210] Carbazoles

*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
NPO17936 Glycosmis arborea Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[15387647]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17936 Glycosmis arborea Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[545691]
NPT80 Cell Line Raji Homo sapiens Activity = 60.0 % PMID[545691]
NPT2 Others Unspecified Activity = 17.4 % PMID[545691]
NPT2 Others Unspecified Activity = 49.1 % PMID[545691]
NPT2 Others Unspecified Activity = 73.7 % PMID[545691]
NPT2 Others Unspecified Activity = 100.0 % PMID[545691]

☑ 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 NPC48353 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
0.9632 High Similarity NPC201697
0.963 High Similarity NPC193777
0.9521 High Similarity NPC475085
0.9521 High Similarity NPC291535
0.9521 High Similarity NPC475112
0.9471 High Similarity NPC162484
0.9307 High Similarity NPC252251
0.9261 High Similarity NPC209174
0.9255 High Similarity NPC153042
0.9216 High Similarity NPC477531
0.9206 High Similarity NPC72211
0.9202 High Similarity NPC70259
0.9171 High Similarity NPC476106
0.9153 High Similarity NPC70956
0.9153 High Similarity NPC243834
0.9149 High Similarity NPC205934
0.9149 High Similarity NPC43787
0.9048 High Similarity NPC131017
0.9031 High Similarity NPC209769
0.8964 High Similarity NPC267423
0.8905 High Similarity NPC6786
0.8883 High Similarity NPC246700
0.8824 High Similarity NPC477532
0.8769 High Similarity NPC476044
0.8731 High Similarity NPC470930
0.8723 High Similarity NPC94943
0.8693 High Similarity NPC470931
0.8684 High Similarity NPC128751
0.867 High Similarity NPC190007
0.8639 High Similarity NPC106833
0.8639 High Similarity NPC469497
0.8629 High Similarity NPC135887
0.8629 High Similarity NPC199277
0.8617 High Similarity NPC212535
0.8551 High Similarity NPC280799
0.8544 High Similarity NPC473179
0.8492 Intermediate Similarity NPC223427
0.8457 Intermediate Similarity NPC88363
0.8411 Intermediate Similarity NPC473182
0.8372 Intermediate Similarity NPC277351
0.8349 Intermediate Similarity NPC473185
0.8342 Intermediate Similarity NPC11017
0.8325 Intermediate Similarity NPC477533
0.8302 Intermediate Similarity NPC202503
0.8286 Intermediate Similarity NPC198503
0.8245 Intermediate Similarity NPC474409
0.8238 Intermediate Similarity NPC150239
0.8238 Intermediate Similarity NPC86078
0.8233 Intermediate Similarity NPC475253
0.8213 Intermediate Similarity NPC478074
0.8204 Intermediate Similarity NPC208284
0.82 Intermediate Similarity NPC128823
0.8187 Intermediate Similarity NPC84478
0.8182 Intermediate Similarity NPC314552
0.8155 Intermediate Similarity NPC11464
0.8155 Intermediate Similarity NPC199667
0.8143 Intermediate Similarity NPC247803
0.8143 Intermediate Similarity NPC46561
0.8135 Intermediate Similarity NPC176127
0.8116 Intermediate Similarity NPC9894
0.8116 Intermediate Similarity NPC87413
0.8107 Intermediate Similarity NPC473181
0.8077 Intermediate Similarity NPC473180
0.8073 Intermediate Similarity NPC72980
0.8069 Intermediate Similarity NPC329747
0.8061 Intermediate Similarity NPC66083
0.8058 Intermediate Similarity NPC475910
0.8047 Intermediate Similarity NPC227908
0.8045 Intermediate Similarity NPC473183
0.802 Intermediate Similarity NPC242928
0.7991 Intermediate Similarity NPC280272
0.799 Intermediate Similarity NPC280964
0.799 Intermediate Similarity NPC294620
0.799 Intermediate Similarity NPC316981
0.799 Intermediate Similarity NPC141915
0.799 Intermediate Similarity NPC114335
0.7981 Intermediate Similarity NPC174760
0.7971 Intermediate Similarity NPC39679
0.7955 Intermediate Similarity NPC473184
0.7952 Intermediate Similarity NPC266931
0.7923 Intermediate Similarity NPC249583
0.7923 Intermediate Similarity NPC4687
0.7919 Intermediate Similarity NPC473187
0.7917 Intermediate Similarity NPC179287
0.7913 Intermediate Similarity NPC285558
0.7905 Intermediate Similarity NPC310211
0.7905 Intermediate Similarity NPC308137
0.79 Intermediate Similarity NPC99666
0.7892 Intermediate Similarity NPC329793
0.789 Intermediate Similarity NPC274640
0.7888 Intermediate Similarity NPC89549
0.7877 Intermediate Similarity NPC170114
0.7877 Intermediate Similarity NPC3207
0.7874 Intermediate Similarity NPC300156
0.7874 Intermediate Similarity NPC45190
0.7871 Intermediate Similarity NPC251090
0.7867 Intermediate Similarity NPC471080
0.7867 Intermediate Similarity NPC469592
0.7861 Intermediate Similarity NPC307963
0.7857 Intermediate Similarity NPC23294
0.785 Intermediate Similarity NPC213530
0.785 Intermediate Similarity NPC193267
0.784 Intermediate Similarity NPC169402
0.783 Intermediate Similarity NPC470549
0.783 Intermediate Similarity NPC116238
0.7828 Intermediate Similarity NPC61350
0.7814 Intermediate Similarity NPC132642
0.781 Intermediate Similarity NPC303951
0.7804 Intermediate Similarity NPC469594
0.7798 Intermediate Similarity NPC200888
0.7788 Intermediate Similarity NPC51388
0.7784 Intermediate Similarity NPC288943
0.7778 Intermediate Similarity NPC469440
0.7772 Intermediate Similarity NPC475190
0.7742 Intermediate Similarity NPC144452
0.7736 Intermediate Similarity NPC94157
0.7731 Intermediate Similarity NPC225279
0.7725 Intermediate Similarity NPC471304
0.7716 Intermediate Similarity NPC474798
0.7714 Intermediate Similarity NPC86834
0.7714 Intermediate Similarity NPC210828
0.7711 Intermediate Similarity NPC76748
0.77 Intermediate Similarity NPC46580
0.7699 Intermediate Similarity NPC475844
0.7685 Intermediate Similarity NPC208084
0.7673 Intermediate Similarity NPC92111
0.7673 Intermediate Similarity NPC469390
0.7662 Intermediate Similarity NPC296527
0.7658 Intermediate Similarity NPC474688
0.7658 Intermediate Similarity NPC474701
0.7653 Intermediate Similarity NPC283152
0.7633 Intermediate Similarity NPC249040
0.7626 Intermediate Similarity NPC211416
0.7619 Intermediate Similarity NPC304183
0.7615 Intermediate Similarity NPC310118
0.7611 Intermediate Similarity NPC131486
0.7611 Intermediate Similarity NPC11408
0.761 Intermediate Similarity NPC13880
0.76 Intermediate Similarity NPC295228
0.76 Intermediate Similarity NPC314002
0.76 Intermediate Similarity NPC476319
0.7596 Intermediate Similarity NPC232727
0.7593 Intermediate Similarity NPC293151
0.7585 Intermediate Similarity NPC32200
0.7571 Intermediate Similarity NPC164374
0.7571 Intermediate Similarity NPC137929
0.7562 Intermediate Similarity NPC171171
0.7561 Intermediate Similarity NPC276517
0.7561 Intermediate Similarity NPC326634
0.7559 Intermediate Similarity NPC167860
0.7559 Intermediate Similarity NPC123976
0.7558 Intermediate Similarity NPC96321
0.7558 Intermediate Similarity NPC184408
0.7558 Intermediate Similarity NPC473041
0.7558 Intermediate Similarity NPC303658
0.755 Intermediate Similarity NPC204717
0.755 Intermediate Similarity NPC62069
0.7548 Intermediate Similarity NPC176538
0.7546 Intermediate Similarity NPC183407
0.7544 Intermediate Similarity NPC217554
0.7536 Intermediate Similarity NPC306376
0.7524 Intermediate Similarity NPC477135
0.7523 Intermediate Similarity NPC470126
0.75 Intermediate Similarity NPC18487
0.75 Intermediate Similarity NPC118121
0.75 Intermediate Similarity NPC220765
0.7488 Intermediate Similarity NPC475070
0.7488 Intermediate Similarity NPC474188
0.7488 Intermediate Similarity NPC77555
0.7488 Intermediate Similarity NPC112206
0.7488 Intermediate Similarity NPC202605
0.7479 Intermediate Similarity NPC189079
0.7475 Intermediate Similarity NPC204385
0.7465 Intermediate Similarity NPC469928
0.7465 Intermediate Similarity NPC330009
0.7462 Intermediate Similarity NPC312872
0.7453 Intermediate Similarity NPC472111
0.7446 Intermediate Similarity NPC284141
0.7444 Intermediate Similarity NPC110151
0.744 Intermediate Similarity NPC242209
0.7436 Intermediate Similarity NPC133609
0.7435 Intermediate Similarity NPC26850
0.743 Intermediate Similarity NPC476116
0.743 Intermediate Similarity NPC469589
0.7427 Intermediate Similarity NPC79293
0.7427 Intermediate Similarity NPC279401
0.7426 Intermediate Similarity NPC473189
0.7419 Intermediate Similarity NPC118228
0.7418 Intermediate Similarity NPC321428
0.7411 Intermediate Similarity NPC253580
0.7395 Intermediate Similarity NPC5145
0.7389 Intermediate Similarity NPC474192
0.7389 Intermediate Similarity NPC475720
0.7389 Intermediate Similarity NPC132329
0.7387 Intermediate Similarity NPC96890
0.7387 Intermediate Similarity NPC184964
0.7385 Intermediate Similarity NPC152768
0.7385 Intermediate Similarity NPC148183
0.7381 Intermediate Similarity NPC315957
0.7376 Intermediate Similarity NPC60621

  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 NPC48353 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
0.8235 Intermediate Similarity NPD5658 Approved
0.8227 Intermediate Similarity NPD3003 Approved
0.8182 Intermediate Similarity NPD5164 Discontinued
0.8048 Intermediate Similarity NPD5612 Discontinued
0.803 Intermediate Similarity NPD4511 Phase 1
0.802 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.801 Intermediate Similarity NPD7452 Approved
0.801 Intermediate Similarity NPD7222 Phase 2
0.801 Intermediate Similarity NPD7453 Approved
0.8 Intermediate Similarity NPD5902 Approved
0.8 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5903 Approved
0.7931 Intermediate Similarity NPD1768 Approved
0.791 Intermediate Similarity NPD4418 Discontinued
0.7861 Intermediate Similarity NPD1038 Approved
0.7822 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.7788 Intermediate Similarity NPD5530 Phase 1
0.7772 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7772 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD7558 Phase 2
0.7748 Intermediate Similarity NPD6494 Phase 2
0.7739 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7731 Intermediate Similarity NPD5930 Phase 3
0.7721 Intermediate Similarity NPD6985 Discontinued
0.7689 Intermediate Similarity NPD4502 Phase 2
0.7688 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7685 Intermediate Similarity NPD7194 Discontinued
0.7667 Intermediate Similarity NPD1392 Approved
0.7638 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD3920 Phase 2
0.75 Intermediate Similarity NPD3825 Phase 3
0.7488 Intermediate Similarity NPD4795 Phase 2
0.7487 Intermediate Similarity NPD1326 Approved
0.7487 Intermediate Similarity NPD1325 Approved
0.7477 Intermediate Similarity NPD5632 Approved
0.7442 Intermediate Similarity NPD5066 Phase 2
0.7442 Intermediate Similarity NPD6220 Phase 3
0.7442 Intermediate Similarity NPD5067 Phase 2
0.7427 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD7221 Approved
0.7421 Intermediate Similarity NPD7219 Approved
0.7418 Intermediate Similarity NPD5429 Discontinued
0.7407 Intermediate Similarity NPD7069 Discontinued
0.7404 Intermediate Similarity NPD7948 Phase 1
0.7391 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD2916 Discontinued
0.7381 Intermediate Similarity NPD1739 Approved
0.7381 Intermediate Similarity NPD1740 Approved
0.7371 Intermediate Similarity NPD4349 Approved
0.7371 Intermediate Similarity NPD4350 Approved
0.7371 Intermediate Similarity NPD4305 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD8403 Phase 1
0.7364 Intermediate Similarity NPD3875 Discontinued
0.7363 Intermediate Similarity NPD4204 Approved
0.7363 Intermediate Similarity NPD4203 Approved
0.7361 Intermediate Similarity NPD5936 Approved
0.7361 Intermediate Similarity NPD5939 Approved
0.7342 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5559 Phase 2
0.733 Intermediate Similarity NPD5913 Phase 3
0.733 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD6242 Discontinued
0.731 Intermediate Similarity NPD4724 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD6590 Discontinued
0.7273 Intermediate Similarity NPD5512 Phase 3
0.7265 Intermediate Similarity NPD5488 Discontinued
0.7265 Intermediate Similarity NPD1954 Phase 1
0.726 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD802 Phase 2
0.7257 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD6290 Phase 2
0.7252 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD8396 Approved
0.7251 Intermediate Similarity NPD2175 Phase 3
0.7251 Intermediate Similarity NPD2177 Approved
0.7251 Intermediate Similarity NPD8395 Approved
0.7251 Intermediate Similarity NPD2176 Approved
0.7248 Intermediate Similarity NPD3815 Phase 1
0.7248 Intermediate Similarity NPD3816 Phase 1
0.7238 Intermediate Similarity NPD5003 Discontinued
0.7238 Intermediate Similarity NPD2952 Discontinued
0.7224 Intermediate Similarity NPD8363 Approved
0.7224 Intermediate Similarity NPD8364 Approved
0.7222 Intermediate Similarity NPD6230 Discontinued
0.7222 Intermediate Similarity NPD2189 Approved
0.7222 Intermediate Similarity NPD2187 Approved
0.7212 Intermediate Similarity NPD3921 Approved
0.7212 Intermediate Similarity NPD3924 Approved
0.7212 Intermediate Similarity NPD3923 Approved
0.7212 Intermediate Similarity NPD3922 Approved
0.7207 Intermediate Similarity NPD3763 Approved
0.7198 Intermediate Similarity NPD5905 Phase 1
0.7188 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD7479 Phase 2
0.717 Intermediate Similarity NPD3814 Phase 1
0.7169 Intermediate Similarity NPD2794 Discontinued
0.7167 Intermediate Similarity NPD8244 Phase 2
0.7166 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD8358 Approved
0.7157 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD6975 Discontinued
0.7149 Intermediate Similarity NPD6530 Approved
0.7149 Intermediate Similarity NPD6531 Approved
0.7143 Intermediate Similarity NPD5506 Approved
0.7143 Intermediate Similarity NPD7672 Approved
0.7143 Intermediate Similarity NPD3810 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5507 Approved
0.7143 Intermediate Similarity NPD7671 Approved
0.7137 Intermediate Similarity NPD6473 Phase 1
0.7136 Intermediate Similarity NPD5944 Phase 1
0.7136 Intermediate Similarity NPD5945 Phase 1
0.7136 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD6150 Discontinued
0.7124 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD5416 Discontinued
0.712 Intermediate Similarity NPD8466 Approved
0.712 Intermediate Similarity NPD8429 Approved
0.712 Intermediate Similarity NPD8467 Approved
0.712 Intermediate Similarity NPD8465 Approved
0.712 Intermediate Similarity NPD8427 Approved
0.712 Intermediate Similarity NPD8428 Approved
0.7118 Intermediate Similarity NPD4996 Approved
0.7118 Intermediate Similarity NPD4995 Approved
0.7117 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD6736 Discontinued
0.7105 Intermediate Similarity NPD7555 Discontinued
0.7101 Intermediate Similarity NPD6243 Phase 3
0.7101 Intermediate Similarity NPD6244 Phase 3
0.7089 Intermediate Similarity NPD3837 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD7395 Discontinued
0.7075 Intermediate Similarity NPD6769 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD4925 Approved
0.7074 Intermediate Similarity NPD7589 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD6147 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.7061 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD484 Approved
0.7053 Intermediate Similarity NPD5256 Discontinued
0.7051 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD6246 Approved
0.7048 Intermediate Similarity NPD6569 Phase 2
0.7043 Intermediate Similarity NPD6962 Phase 2
0.7034 Intermediate Similarity NPD7592 Phase 2
0.7033 Intermediate Similarity NPD2564 Approved
0.7033 Intermediate Similarity NPD2565 Phase 2
0.7032 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD6964 Approved
0.7026 Intermediate Similarity NPD6963 Approved
0.7024 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD7678 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD7417 Discontinued
0.7018 Intermediate Similarity NPD7051 Phase 3
0.7018 Intermediate Similarity NPD7050 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD4551 Phase 2
0.7014 Intermediate Similarity NPD3330 Phase 1
0.7013 Intermediate Similarity NPD4885 Approved
0.7009 Intermediate Similarity NPD2151 Approved
0.7009 Intermediate Similarity NPD8109 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD8459 Approved
0.7008 Intermediate Similarity NPD8460 Approved
0.7008 Intermediate Similarity NPD8426 Approved
0.7008 Intermediate Similarity NPD8425 Approved
0.7005 Intermediate Similarity NPD6138 Clinical (unspecified phase)
0.7004 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8512 Phase 3
0.6996 Remote Similarity NPD8091 Phase 3
0.6995 Remote Similarity NPD6988 Phase 1
0.6992 Remote Similarity NPD4876 Phase 3
0.6992 Remote Similarity NPD4875 Phase 3
0.6991 Remote Similarity NPD5669 Clinical (unspecified phase)
0.6991 Remote Similarity NPD6208 Discontinued
0.6983 Remote Similarity NPD4373 Phase 2
0.6981 Remote Similarity NPD6251 Discontinued
0.6978 Remote Similarity NPD3258 Approved
0.6978 Remote Similarity NPD3402 Phase 1
0.6972 Remote Similarity NPD3932 Clinical (unspecified phase)
0.6971 Remote Similarity NPD6742 Phase 2
0.6971 Remote Similarity NPD6743 Phase 2
0.697 Remote Similarity NPD1505 Phase 2
0.697 Remote Similarity NPD1684 Approved
0.697 Remote Similarity NPD1685 Approved
0.6967 Remote Similarity NPD7955 Approved
0.6967 Remote Similarity NPD7956 Approved
0.6963 Remote Similarity NPD2727 Phase 2
0.6963 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6961 Remote Similarity NPD5810 Discontinued
0.6959 Remote Similarity NPD6991 Approved
0.6959 Remote Similarity NPD2920 Discontinued
0.6958 Remote Similarity NPD5482 Discontinued
0.6955 Remote Similarity NPD4437 Phase 3
0.6948 Remote Similarity NPD6550 Discontinued
0.6944 Remote Similarity NPD6592 Clinical (unspecified phase)
0.6942 Remote Similarity NPD3037 Phase 1
0.6941 Remote Similarity NPD3930 Clinical (unspecified phase)
0.6937 Remote Similarity NPD5097 Phase 2
0.6936 Remote Similarity NPD7729 Clinical (unspecified phase)
0.6934 Remote Similarity NPD6361 Phase 2
0.6933 Remote Similarity NPD3354 Phase 2
0.6927 Remote Similarity NPD4037 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