Structure

Physi-Chem Properties

Molecular Weight:  334.18
Volume:  350.836
LogP:  4.332
LogD:  3.572
LogS:  -4.379
# Rotatable Bonds:  1
TPSA:  75.99
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.766
Synthetic Accessibility Score:  3.814
Fsp3:  0.526
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:  -4.768
MDCK Permeability:  4.9842125008581206e-05
Pgp-inhibitor:  0.091
Pgp-substrate:  0.081
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.125
30% Bioavailability (F30%):  0.689

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.548
Plasma Protein Binding (PPB):  96.56889343261719%
Volume Distribution (VD):  0.838
Pgp-substrate:  3.9788291454315186%

ADMET: Metabolism

CYP1A2-inhibitor:  0.921
CYP1A2-substrate:  0.777
CYP2C19-inhibitor:  0.573
CYP2C19-substrate:  0.431
CYP2C9-inhibitor:  0.509
CYP2C9-substrate:  0.943
CYP2D6-inhibitor:  0.89
CYP2D6-substrate:  0.887
CYP3A4-inhibitor:  0.734
CYP3A4-substrate:  0.132

ADMET: Excretion

Clearance (CL):  12.303
Half-life (T1/2):  0.451

ADMET: Toxicity

hERG Blockers:  0.045
Human Hepatotoxicity (H-HT):  0.492
Drug-inuced Liver Injury (DILI):  0.139
AMES Toxicity:  0.052
Rat Oral Acute Toxicity:  0.016
Maximum Recommended Daily Dose:  0.853
Skin Sensitization:  0.954
Carcinogencity:  0.491
Eye Corrosion:  0.111
Eye Irritation:  0.865
Respiratory Toxicity:  0.849

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

  Natural Product: NPC474385

Natural Product ID:  NPC474385
Common Name*:   Methyl Beta-Zearalenol
IUPAC Name:   (2E,7S,11S)-7,15-dihydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(18),2,14,16-tetraen-13-one
Synonyms:   Methyl Beta-Zearalenol
Standard InCHIKey:  JVYBAZCPWDLGCX-KHKWHVMBSA-N
Standard InCHI:  InChI=1S/C19H26O5/c1-13-7-6-10-15(20)9-5-3-4-8-14-11-16(23-2)12-17(21)18(14)19(22)24-13/h4,8,11-13,15,20-21H,3,5-7,9-10H2,1-2H3/b8-4+/t13-,15-/m0/s1
SMILES:  COc1cc2/C=C/CCC[C@H](O)CCC[C@@H](OC(=O)c2c(c1)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465785
PubChem CID:   6478919
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000147] Macrolides and analogues

*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
NPO27821.1 Pochonia chlamydosporia Under-species n.a. n.a. n.a. n.a. n.a. PMID[12828470]

☑ 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
NPT91 Cell Line KB Homo sapiens IC50 = 55980.0 nM PMID[564038]

☑ 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 NPC474385 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
0.9854 High Similarity NPC210425
0.9854 High Similarity NPC277426
0.9854 High Similarity NPC86373
0.9854 High Similarity NPC280404
0.9781 High Similarity NPC51106
0.9779 High Similarity NPC1704
0.9779 High Similarity NPC475730
0.9779 High Similarity NPC67650
0.9643 High Similarity NPC472036
0.9643 High Similarity NPC210320
0.964 High Similarity NPC472034
0.9638 High Similarity NPC472006
0.9638 High Similarity NPC469542
0.9635 High Similarity NPC158634
0.963 High Similarity NPC135837
0.9574 High Similarity NPC73411
0.9574 High Similarity NPC215711
0.9571 High Similarity NPC472033
0.9565 High Similarity NPC469579
0.9562 High Similarity NPC158472
0.9559 High Similarity NPC212693
0.9559 High Similarity NPC478200
0.9559 High Similarity NPC94248
0.9559 High Similarity NPC33144
0.9507 High Similarity NPC476684
0.9489 High Similarity NPC32360
0.9485 High Similarity NPC70380
0.9481 High Similarity NPC180905
0.9481 High Similarity NPC182496
0.9441 High Similarity NPC469619
0.9441 High Similarity NPC469670
0.9437 High Similarity NPC240622
0.9437 High Similarity NPC471642
0.9437 High Similarity NPC471641
0.9437 High Similarity NPC240253
0.9433 High Similarity NPC107625
0.9424 High Similarity NPC250755
0.9416 High Similarity NPC191835
0.9375 High Similarity NPC200773
0.9375 High Similarity NPC240768
0.9375 High Similarity NPC215921
0.9375 High Similarity NPC70016
0.9353 High Similarity NPC478201
0.9353 High Similarity NPC313123
0.9353 High Similarity NPC472035
0.9353 High Similarity NPC90411
0.9353 High Similarity NPC478217
0.9348 High Similarity NPC105456
0.9348 High Similarity NPC268052
0.9348 High Similarity NPC139634
0.9343 High Similarity NPC71256
0.9333 High Similarity NPC153783
0.9291 High Similarity NPC95123
0.9291 High Similarity NPC66404
0.9275 High Similarity NPC472602
0.927 High Similarity NPC235115
0.9236 High Similarity NPC270160
0.9236 High Similarity NPC237440
0.9225 High Similarity NPC257558
0.9225 High Similarity NPC312789
0.9225 High Similarity NPC134621
0.9225 High Similarity NPC83272
0.922 High Similarity NPC478202
0.9214 High Similarity NPC472605
0.9214 High Similarity NPC244923
0.9214 High Similarity NPC53649
0.9214 High Similarity NPC472604
0.9185 High Similarity NPC219892
0.9185 High Similarity NPC189823
0.9184 High Similarity NPC99381
0.9161 High Similarity NPC225173
0.9161 High Similarity NPC163846
0.9161 High Similarity NPC237208
0.9155 High Similarity NPC151607
0.9155 High Similarity NPC126882
0.9155 High Similarity NPC478203
0.9155 High Similarity NPC42540
0.9155 High Similarity NPC210966
0.9149 High Similarity NPC96692
0.9149 High Similarity NPC105648
0.9143 High Similarity NPC472601
0.9143 High Similarity NPC472600
0.9143 High Similarity NPC165172
0.9137 High Similarity NPC9121
0.9137 High Similarity NPC177307
0.9137 High Similarity NPC475974
0.9124 High Similarity NPC175943
0.9103 High Similarity NPC77325
0.9103 High Similarity NPC4423
0.9097 High Similarity NPC14098
0.9097 High Similarity NPC125801
0.9097 High Similarity NPC8817
0.9091 High Similarity NPC29577
0.9085 High Similarity NPC159721
0.9085 High Similarity NPC471731
0.9078 High Similarity NPC220106
0.9078 High Similarity NPC472603
0.9071 High Similarity NPC247409
0.9071 High Similarity NPC52358
0.9065 High Similarity NPC194579
0.9065 High Similarity NPC178467
0.9065 High Similarity NPC65837
0.9065 High Similarity NPC474771
0.9065 High Similarity NPC474849
0.9065 High Similarity NPC149372
0.9058 High Similarity NPC142027
0.9054 High Similarity NPC16082
0.9054 High Similarity NPC82592
0.9048 High Similarity NPC273483
0.9048 High Similarity NPC167903
0.9041 High Similarity NPC179178
0.9041 High Similarity NPC475460
0.9034 High Similarity NPC153417
0.9034 High Similarity NPC37139
0.9028 High Similarity NPC470357
0.9028 High Similarity NPC473023
0.9021 High Similarity NPC470932
0.9014 High Similarity NPC471733
0.9014 High Similarity NPC471640
0.9014 High Similarity NPC471644
0.9014 High Similarity NPC49108
0.9007 High Similarity NPC155205
0.9 High Similarity NPC472403
0.8986 High Similarity NPC281477
0.8978 High Similarity NPC470160
0.8973 High Similarity NPC291049
0.8973 High Similarity NPC233267
0.8971 High Similarity NPC42292
0.8971 High Similarity NPC307732
0.8966 High Similarity NPC12305
0.8966 High Similarity NPC137296
0.8963 High Similarity NPC293453
0.8958 High Similarity NPC75694
0.8958 High Similarity NPC473692
0.8951 High Similarity NPC471643
0.8951 High Similarity NPC471639
0.8951 High Similarity NPC472610
0.8936 High Similarity NPC92655
0.8936 High Similarity NPC474655
0.8936 High Similarity NPC88269
0.8933 High Similarity NPC84935
0.8933 High Similarity NPC246466
0.8933 High Similarity NPC190020
0.8933 High Similarity NPC77679
0.8929 High Similarity NPC470397
0.8929 High Similarity NPC472367
0.8929 High Similarity NPC476333
0.8929 High Similarity NPC473391
0.8929 High Similarity NPC472364
0.8926 High Similarity NPC79998
0.8921 High Similarity NPC27407
0.8919 High Similarity NPC474843
0.8919 High Similarity NPC478224
0.8913 High Similarity NPC203817
0.8912 High Similarity NPC158866
0.8912 High Similarity NPC295036
0.8912 High Similarity NPC56204
0.8912 High Similarity NPC60413
0.8912 High Similarity NPC472891
0.8912 High Similarity NPC96501
0.8905 High Similarity NPC214702
0.8905 High Similarity NPC470831
0.8904 High Similarity NPC172329
0.8904 High Similarity NPC105415
0.8904 High Similarity NPC2569
0.8904 High Similarity NPC221352
0.8897 High Similarity NPC267509
0.8889 High Similarity NPC184702
0.8881 High Similarity NPC82913
0.8874 High Similarity NPC470339
0.8867 High Similarity NPC227062
0.8867 High Similarity NPC150227
0.8867 High Similarity NPC472050
0.8859 High Similarity NPC472799
0.8857 High Similarity NPC158481
0.8857 High Similarity NPC84699
0.8857 High Similarity NPC50455
0.8857 High Similarity NPC242712
0.8857 High Similarity NPC291454
0.8851 High Similarity NPC133856
0.8851 High Similarity NPC91809
0.8849 High Similarity NPC474097
0.8844 High Similarity NPC84142
0.8844 High Similarity NPC6923
0.8841 High Similarity NPC476389
0.8836 High Similarity NPC471734
0.8832 High Similarity NPC17840
0.8832 High Similarity NPC473271
0.8832 High Similarity NPC247477
0.8828 High Similarity NPC32470
0.8819 High Similarity NPC310340
0.8816 High Similarity NPC472055
0.8811 High Similarity NPC307990
0.8811 High Similarity NPC37530
0.8811 High Similarity NPC16455
0.8803 High Similarity NPC472368
0.8803 High Similarity NPC275356
0.8803 High Similarity NPC57380
0.88 High Similarity NPC170189
0.88 High Similarity NPC89625

  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 NPC474385 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
0.9348 High Similarity NPD970 Clinical (unspecified phase)
0.8958 High Similarity NPD2534 Approved
0.8958 High Similarity NPD2533 Approved
0.8958 High Similarity NPD2532 Approved
0.8733 High Similarity NPD7819 Suspended
0.8472 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8472 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD1510 Phase 2
0.844 Intermediate Similarity NPD1240 Approved
0.8425 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8414 Intermediate Similarity NPD1549 Phase 2
0.8378 Intermediate Similarity NPD6799 Approved
0.8366 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD6232 Discontinued
0.8323 Intermediate Similarity NPD7075 Discontinued
0.8322 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD1607 Approved
0.8301 Intermediate Similarity NPD1934 Approved
0.8299 Intermediate Similarity NPD3750 Approved
0.8298 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8289 Intermediate Similarity NPD4380 Phase 2
0.8276 Intermediate Similarity NPD1551 Phase 2
0.8276 Intermediate Similarity NPD2935 Discontinued
0.8276 Intermediate Similarity NPD2796 Approved
0.8247 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD7411 Suspended
0.8194 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD3817 Phase 2
0.8187 Intermediate Similarity NPD7473 Discontinued
0.8182 Intermediate Similarity NPD6801 Discontinued
0.817 Intermediate Similarity NPD6599 Discontinued
0.8165 Intermediate Similarity NPD6959 Discontinued
0.8141 Intermediate Similarity NPD7768 Phase 2
0.8141 Intermediate Similarity NPD3882 Suspended
0.8133 Intermediate Similarity NPD1511 Approved
0.8129 Intermediate Similarity NPD2801 Approved
0.8125 Intermediate Similarity NPD230 Phase 1
0.8113 Intermediate Similarity NPD5711 Approved
0.8113 Intermediate Similarity NPD5710 Approved
0.8089 Intermediate Similarity NPD3749 Approved
0.8089 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD5844 Phase 1
0.8054 Intermediate Similarity NPD4628 Phase 3
0.8026 Intermediate Similarity NPD1512 Approved
0.8025 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8015 Intermediate Similarity NPD9545 Approved
0.8012 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD6166 Phase 2
0.8012 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD9717 Approved
0.7975 Intermediate Similarity NPD7054 Approved
0.7974 Intermediate Similarity NPD5403 Approved
0.7962 Intermediate Similarity NPD5402 Approved
0.7961 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7959 Intermediate Similarity NPD3748 Approved
0.7927 Intermediate Similarity NPD7472 Approved
0.7927 Intermediate Similarity NPD7074 Phase 3
0.7914 Intermediate Similarity NPD3818 Discontinued
0.7892 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD6797 Phase 2
0.7868 Intermediate Similarity NPD9493 Approved
0.7867 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD2800 Approved
0.7843 Intermediate Similarity NPD5401 Approved
0.7831 Intermediate Similarity NPD7251 Discontinued
0.7823 Intermediate Similarity NPD6651 Approved
0.7817 Intermediate Similarity NPD1203 Approved
0.7815 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD411 Approved
0.7786 Intermediate Similarity NPD422 Phase 1
0.7784 Intermediate Similarity NPD7808 Phase 3
0.7778 Intermediate Similarity NPD6832 Phase 2
0.7758 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD3226 Approved
0.7755 Intermediate Similarity NPD447 Suspended
0.7748 Intermediate Similarity NPD1243 Approved
0.7742 Intermediate Similarity NPD920 Approved
0.7727 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD6559 Discontinued
0.7718 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD7033 Discontinued
0.7718 Intermediate Similarity NPD2799 Discontinued
0.7718 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD1465 Phase 2
0.7667 Intermediate Similarity NPD6100 Approved
0.7667 Intermediate Similarity NPD6099 Approved
0.7665 Intermediate Similarity NPD5953 Discontinued
0.7654 Intermediate Similarity NPD5494 Approved
0.7643 Intermediate Similarity NPD4626 Approved
0.7643 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD2654 Approved
0.763 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD2346 Discontinued
0.7613 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD37 Approved
0.7607 Intermediate Similarity NPD7199 Phase 2
0.7606 Intermediate Similarity NPD1608 Approved
0.7593 Intermediate Similarity NPD919 Approved
0.7578 Intermediate Similarity NPD4966 Approved
0.7578 Intermediate Similarity NPD4967 Phase 2
0.7578 Intermediate Similarity NPD4965 Approved
0.7571 Intermediate Similarity NPD5691 Approved
0.7568 Intermediate Similarity NPD943 Approved
0.756 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD3764 Approved
0.755 Intermediate Similarity NPD5406 Approved
0.755 Intermediate Similarity NPD5408 Approved
0.755 Intermediate Similarity NPD5404 Approved
0.755 Intermediate Similarity NPD5405 Approved
0.7548 Intermediate Similarity NPD7390 Discontinued
0.7545 Intermediate Similarity NPD7286 Phase 2
0.7518 Intermediate Similarity NPD1778 Approved
0.7517 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD1019 Discontinued
0.7517 Intermediate Similarity NPD5124 Phase 1
0.7516 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2344 Approved
0.7485 Intermediate Similarity NPD6234 Discontinued
0.7471 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD7229 Phase 3
0.7452 Intermediate Similarity NPD6273 Approved
0.7448 Intermediate Similarity NPD2797 Approved
0.7436 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD3268 Approved
0.7415 Intermediate Similarity NPD4908 Phase 1
0.741 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD4288 Approved
0.7397 Intermediate Similarity NPD2798 Approved
0.7394 Intermediate Similarity NPD17 Approved
0.7386 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6004 Phase 3
0.7386 Intermediate Similarity NPD6002 Phase 3
0.7386 Intermediate Similarity NPD6005 Phase 3
0.7386 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD3751 Discontinued
0.7379 Intermediate Similarity NPD1283 Approved
0.7365 Intermediate Similarity NPD3027 Phase 3
0.7361 Intermediate Similarity NPD9269 Phase 2
0.7355 Intermediate Similarity NPD7003 Approved
0.7349 Intermediate Similarity NPD3787 Discontinued
0.7347 Intermediate Similarity NPD9494 Approved
0.7343 Intermediate Similarity NPD3496 Discontinued
0.7333 Intermediate Similarity NPD4060 Phase 1
0.7326 Intermediate Similarity NPD8312 Approved
0.7326 Intermediate Similarity NPD8313 Approved
0.7324 Intermediate Similarity NPD9268 Approved
0.7315 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD2313 Discontinued
0.7315 Intermediate Similarity NPD1296 Phase 2
0.7314 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD2309 Approved
0.7308 Intermediate Similarity NPD6190 Approved
0.7305 Intermediate Similarity NPD3926 Phase 2
0.7301 Intermediate Similarity NPD5353 Approved
0.7292 Intermediate Similarity NPD1201 Approved
0.7292 Intermediate Similarity NPD1610 Phase 2
0.729 Intermediate Similarity NPD1652 Phase 2
0.7285 Intermediate Similarity NPD6355 Discontinued
0.7279 Intermediate Similarity NPD74 Approved
0.7279 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD9266 Approved
0.7278 Intermediate Similarity NPD7228 Approved
0.726 Intermediate Similarity NPD3225 Approved
0.7255 Intermediate Similarity NPD4308 Phase 3
0.7254 Intermediate Similarity NPD1548 Phase 1
0.725 Intermediate Similarity NPD1653 Approved
0.7248 Intermediate Similarity NPD4625 Phase 3
0.7234 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD1613 Approved
0.7219 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2979 Phase 3
0.7213 Intermediate Similarity NPD7435 Discontinued
0.7211 Intermediate Similarity NPD1470 Approved
0.7211 Intermediate Similarity NPD1164 Approved
0.7208 Intermediate Similarity NPD4477 Approved
0.7208 Intermediate Similarity NPD4476 Approved
0.7208 Intermediate Similarity NPD2438 Suspended
0.7206 Intermediate Similarity NPD9263 Approved
0.7206 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD9267 Approved
0.7206 Intermediate Similarity NPD9264 Approved
0.7205 Intermediate Similarity NPD7458 Discontinued
0.7204 Intermediate Similarity NPD8151 Discontinued
0.7202 Intermediate Similarity NPD5242 Approved
0.72 Intermediate Similarity NPD6798 Discontinued
0.72 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD8150 Discontinued
0.7192 Intermediate Similarity NPD4749 Approved
0.7186 Intermediate Similarity NPD1247 Approved
0.7176 Intermediate Similarity NPD7177 Discontinued
0.7172 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD1281 Approved
0.7171 Intermediate Similarity NPD1933 Approved
0.7167 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD5647 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