Structure

Physi-Chem Properties

Molecular Weight:  358.21
Volume:  391.297
LogP:  5.292
LogD:  4.03
LogS:  -5.224
# Rotatable Bonds:  12
TPSA:  52.6
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.241
Synthetic Accessibility Score:  2.9
Fsp3:  0.545
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:  -4.699
MDCK Permeability:  2.9276545319589786e-05
Pgp-inhibitor:  0.841
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.038
30% Bioavailability (F30%):  0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.552
Plasma Protein Binding (PPB):  96.75066375732422%
Volume Distribution (VD):  0.558
Pgp-substrate:  2.986598253250122%

ADMET: Metabolism

CYP1A2-inhibitor:  0.866
CYP1A2-substrate:  0.35
CYP2C19-inhibitor:  0.892
CYP2C19-substrate:  0.085
CYP2C9-inhibitor:  0.694
CYP2C9-substrate:  0.908
CYP2D6-inhibitor:  0.376
CYP2D6-substrate:  0.556
CYP3A4-inhibitor:  0.79
CYP3A4-substrate:  0.217

ADMET: Excretion

Clearance (CL):  6.68
Half-life (T1/2):  0.688

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.944
Drug-inuced Liver Injury (DILI):  0.947
AMES Toxicity:  0.9
Rat Oral Acute Toxicity:  0.757
Maximum Recommended Daily Dose:  0.664
Skin Sensitization:  0.403
Carcinogencity:  0.559
Eye Corrosion:  0.054
Eye Irritation:  0.281
Respiratory Toxicity:  0.866

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

  Natural Product: NPC282230

Natural Product ID:  NPC282230
Common Name*:   Nonanoylbitalin A
IUPAC Name:   2-[(2R)-5-acetyl-2,3-dihydro-1-benzofuran-2-yl]prop-2-enyl nonanoate
Synonyms:   Nonanoylbitalin A
Standard InCHIKey:  NAQCTYLFZQYNHK-OAQYLSRUSA-N
Standard InCHI:  InChI=1S/C22H30O4/c1-4-5-6-7-8-9-10-22(24)25-15-16(2)21-14-19-13-18(17(3)23)11-12-20(19)26-21/h11-13,21H,2,4-10,14-15H2,1,3H3/t21-/m1/s1
SMILES:  CCCCCCCCC(=O)OCC(=C)[C@H]1Cc2cc(ccc2O1)C(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2334422
PubChem CID:   71659267
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000119] Acetophenones

*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
NPO25148.1 Helichrysum italicum Under-species n.a. n.a. Flowered aerial parts Arzana, Sardinia 2010-Jul PMID[23265253]

☑ 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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 128.0 ug.mL-1 PMID[482824]

☑ 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 NPC282230 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 NPC183348
0.9919 High Similarity NPC196979
0.9919 High Similarity NPC15083
0.9919 High Similarity NPC66246
0.9919 High Similarity NPC170546
0.9919 High Similarity NPC470976
0.9919 High Similarity NPC470977
0.9435 High Similarity NPC470858
0.9431 High Similarity NPC11799
0.9431 High Similarity NPC141252
0.9141 High Similarity NPC939
0.9037 High Similarity NPC470856
0.8931 High Similarity NPC470859
0.8837 High Similarity NPC293387
0.8837 High Similarity NPC37512
0.8797 High Similarity NPC247743
0.8714 High Similarity NPC286038
0.8682 High Similarity NPC165556
0.8676 High Similarity NPC253616
0.8652 High Similarity NPC66991
0.864 High Similarity NPC293424
0.8629 High Similarity NPC470860
0.8626 High Similarity NPC50583
0.8623 High Similarity NPC184053
0.8613 High Similarity NPC36414
0.8603 High Similarity NPC268081
0.8571 High Similarity NPC279596
0.8561 High Similarity NPC473019
0.8551 High Similarity NPC472515
0.855 High Similarity NPC121104
0.8511 High Similarity NPC171656
0.8496 Intermediate Similarity NPC86774
0.8496 Intermediate Similarity NPC327457
0.8496 Intermediate Similarity NPC109778
0.8478 Intermediate Similarity NPC473988
0.8473 Intermediate Similarity NPC237868
0.8472 Intermediate Similarity NPC191104
0.8462 Intermediate Similarity NPC89630
0.8462 Intermediate Similarity NPC221798
0.8444 Intermediate Similarity NPC55147
0.8444 Intermediate Similarity NPC54503
0.844 Intermediate Similarity NPC213900
0.844 Intermediate Similarity NPC184702
0.8429 Intermediate Similarity NPC171870
0.8417 Intermediate Similarity NPC11566
0.8417 Intermediate Similarity NPC37206
0.8417 Intermediate Similarity NPC137009
0.8417 Intermediate Similarity NPC136095
0.8413 Intermediate Similarity NPC469954
0.8406 Intermediate Similarity NPC259685
0.8403 Intermediate Similarity NPC88886
0.8403 Intermediate Similarity NPC88445
0.8403 Intermediate Similarity NPC104172
0.8392 Intermediate Similarity NPC14875
0.838 Intermediate Similarity NPC294365
0.838 Intermediate Similarity NPC208584
0.8374 Intermediate Similarity NPC23332
0.8359 Intermediate Similarity NPC230951
0.8357 Intermediate Similarity NPC16455
0.8357 Intermediate Similarity NPC307990
0.8346 Intermediate Similarity NPC2401
0.8346 Intermediate Similarity NPC473744
0.8333 Intermediate Similarity NPC472516
0.8333 Intermediate Similarity NPC254741
0.8333 Intermediate Similarity NPC266743
0.8333 Intermediate Similarity NPC168085
0.8321 Intermediate Similarity NPC470844
0.8321 Intermediate Similarity NPC184219
0.8321 Intermediate Similarity NPC229128
0.832 Intermediate Similarity NPC252004
0.8311 Intermediate Similarity NPC470625
0.8309 Intermediate Similarity NPC229646
0.8309 Intermediate Similarity NPC222036
0.8309 Intermediate Similarity NPC7526
0.8308 Intermediate Similarity NPC291189
0.8308 Intermediate Similarity NPC69403
0.8299 Intermediate Similarity NPC131725
0.8298 Intermediate Similarity NPC297985
0.8298 Intermediate Similarity NPC254010
0.8296 Intermediate Similarity NPC125153
0.8293 Intermediate Similarity NPC473809
0.8293 Intermediate Similarity NPC183648
0.8288 Intermediate Similarity NPC290671
0.8286 Intermediate Similarity NPC473209
0.8286 Intermediate Similarity NPC262635
0.8276 Intermediate Similarity NPC317492
0.8276 Intermediate Similarity NPC164299
0.8273 Intermediate Similarity NPC62735
0.8273 Intermediate Similarity NPC103001
0.8273 Intermediate Similarity NPC38153
0.8268 Intermediate Similarity NPC45104
0.8268 Intermediate Similarity NPC217423
0.8264 Intermediate Similarity NPC471285
0.8264 Intermediate Similarity NPC74539
0.8264 Intermediate Similarity NPC304443
0.8261 Intermediate Similarity NPC163029
0.8261 Intermediate Similarity NPC283331
0.8261 Intermediate Similarity NPC46869
0.8261 Intermediate Similarity NPC99854
0.8255 Intermediate Similarity NPC269495
0.8254 Intermediate Similarity NPC220540
0.8252 Intermediate Similarity NPC474044
0.8248 Intermediate Similarity NPC311339
0.8248 Intermediate Similarity NPC307412
0.8248 Intermediate Similarity NPC209858
0.8248 Intermediate Similarity NPC55149
0.8239 Intermediate Similarity NPC471643
0.8239 Intermediate Similarity NPC51146
0.8239 Intermediate Similarity NPC313036
0.8239 Intermediate Similarity NPC472344
0.8239 Intermediate Similarity NPC147145
0.8239 Intermediate Similarity NPC471639
0.8239 Intermediate Similarity NPC166858
0.8235 Intermediate Similarity NPC14248
0.8235 Intermediate Similarity NPC302844
0.8235 Intermediate Similarity NPC175159
0.8231 Intermediate Similarity NPC10429
0.8227 Intermediate Similarity NPC472409
0.8222 Intermediate Similarity NPC245395
0.8219 Intermediate Similarity NPC180351
0.8219 Intermediate Similarity NPC472421
0.8209 Intermediate Similarity NPC2596
0.8209 Intermediate Similarity NPC125887
0.8207 Intermediate Similarity NPC95526
0.8201 Intermediate Similarity NPC29638
0.8201 Intermediate Similarity NPC161196
0.8201 Intermediate Similarity NPC156910
0.8195 Intermediate Similarity NPC474737
0.8195 Intermediate Similarity NPC188327
0.8195 Intermediate Similarity NPC475236
0.8195 Intermediate Similarity NPC234109
0.8194 Intermediate Similarity NPC471346
0.8188 Intermediate Similarity NPC61499
0.8188 Intermediate Similarity NPC125269
0.8182 Intermediate Similarity NPC59522
0.8182 Intermediate Similarity NPC150408
0.8182 Intermediate Similarity NPC143896
0.8182 Intermediate Similarity NPC310130
0.8182 Intermediate Similarity NPC17262
0.8182 Intermediate Similarity NPC149026
0.8182 Intermediate Similarity NPC470932
0.8182 Intermediate Similarity NPC290038
0.8182 Intermediate Similarity NPC39329
0.8182 Intermediate Similarity NPC91560
0.8182 Intermediate Similarity NPC169591
0.8182 Intermediate Similarity NPC68104
0.8182 Intermediate Similarity NPC257097
0.8182 Intermediate Similarity NPC175504
0.8182 Intermediate Similarity NPC221432
0.8182 Intermediate Similarity NPC164980
0.8182 Intermediate Similarity NPC75049
0.8175 Intermediate Similarity NPC66158
0.8169 Intermediate Similarity NPC201820
0.8169 Intermediate Similarity NPC471644
0.8169 Intermediate Similarity NPC22467
0.8169 Intermediate Similarity NPC229916
0.8169 Intermediate Similarity NPC471640
0.8168 Intermediate Similarity NPC67300
0.8163 Intermediate Similarity NPC318424
0.8163 Intermediate Similarity NPC474744
0.8163 Intermediate Similarity NPC472580
0.8163 Intermediate Similarity NPC472423
0.8163 Intermediate Similarity NPC474772
0.8162 Intermediate Similarity NPC472517
0.8162 Intermediate Similarity NPC473777
0.8156 Intermediate Similarity NPC139554
0.8156 Intermediate Similarity NPC23257
0.8151 Intermediate Similarity NPC39929
0.8151 Intermediate Similarity NPC296030
0.8151 Intermediate Similarity NPC472298
0.8148 Intermediate Similarity NPC238309
0.8146 Intermediate Similarity NPC74749
0.8146 Intermediate Similarity NPC43971
0.8146 Intermediate Similarity NPC19554
0.8146 Intermediate Similarity NPC49009
0.814 Intermediate Similarity NPC98748
0.8138 Intermediate Similarity NPC218300
0.8138 Intermediate Similarity NPC12148
0.8138 Intermediate Similarity NPC282335
0.8138 Intermediate Similarity NPC130581
0.8133 Intermediate Similarity NPC123153
0.8129 Intermediate Similarity NPC278832
0.8129 Intermediate Similarity NPC215109
0.8129 Intermediate Similarity NPC170604
0.8129 Intermediate Similarity NPC64157
0.8129 Intermediate Similarity NPC307401
0.8125 Intermediate Similarity NPC124780
0.8125 Intermediate Similarity NPC179970
0.8125 Intermediate Similarity NPC246903
0.8125 Intermediate Similarity NPC469953
0.8125 Intermediate Similarity NPC197252
0.8125 Intermediate Similarity NPC87486
0.8125 Intermediate Similarity NPC316535
0.8125 Intermediate Similarity NPC209040
0.8125 Intermediate Similarity NPC236766
0.8125 Intermediate Similarity NPC470857
0.8125 Intermediate Similarity NPC473015
0.8125 Intermediate Similarity NPC473013
0.8121 Intermediate Similarity NPC278010
0.8121 Intermediate Similarity NPC250769

  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 NPC282230 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
0.8551 High Similarity NPD7421 Clinical (unspecified phase)
0.8394 Intermediate Similarity NPD2799 Discontinued
0.8346 Intermediate Similarity NPD6832 Phase 2
0.8333 Intermediate Similarity NPD2796 Approved
0.8286 Intermediate Similarity NPD1243 Approved
0.8264 Intermediate Similarity NPD920 Approved
0.824 Intermediate Similarity NPD1241 Discontinued
0.8239 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8143 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8099 Intermediate Similarity NPD4628 Phase 3
0.8092 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.8088 Intermediate Similarity NPD2313 Discontinued
0.8071 Intermediate Similarity NPD2935 Discontinued
0.806 Intermediate Similarity NPD1019 Discontinued
0.8056 Intermediate Similarity NPD6799 Approved
0.8054 Intermediate Similarity NPD7819 Suspended
0.8042 Intermediate Similarity NPD3887 Approved
0.8041 Intermediate Similarity NPD7411 Suspended
0.803 Intermediate Similarity NPD3972 Approved
0.803 Intermediate Similarity NPD9717 Approved
0.8013 Intermediate Similarity NPD7075 Discontinued
0.8 Intermediate Similarity NPD3748 Approved
0.8 Intermediate Similarity NPD5691 Approved
0.7987 Intermediate Similarity NPD6801 Discontinued
0.7985 Intermediate Similarity NPD3267 Approved
0.7985 Intermediate Similarity NPD3266 Approved
0.7971 Intermediate Similarity NPD4307 Phase 2
0.7956 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD6355 Discontinued
0.7887 Intermediate Similarity NPD2344 Approved
0.7877 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD6599 Discontinued
0.7843 Intermediate Similarity NPD919 Approved
0.7842 Intermediate Similarity NPD3140 Approved
0.7842 Intermediate Similarity NPD3142 Approved
0.7832 Intermediate Similarity NPD1549 Phase 2
0.7826 Intermediate Similarity NPD3268 Approved
0.7826 Intermediate Similarity NPD6798 Discontinued
0.7823 Intermediate Similarity NPD3134 Approved
0.7806 Intermediate Similarity NPD6808 Phase 2
0.7792 Intermediate Similarity NPD5494 Approved
0.7786 Intermediate Similarity NPD9545 Approved
0.7785 Intermediate Similarity NPD7458 Discontinued
0.7778 Intermediate Similarity NPD1876 Approved
0.7762 Intermediate Similarity NPD6004 Phase 3
0.7762 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD6005 Phase 3
0.7762 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD6002 Phase 3
0.7762 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD2346 Discontinued
0.7762 Intermediate Similarity NPD2353 Approved
0.7762 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD1358 Approved
0.7755 Intermediate Similarity NPD2533 Approved
0.7755 Intermediate Similarity NPD2532 Approved
0.7755 Intermediate Similarity NPD2534 Approved
0.7746 Intermediate Similarity NPD4308 Phase 3
0.7724 Intermediate Similarity NPD3750 Approved
0.7722 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7721 Intermediate Similarity NPD2797 Approved
0.7721 Intermediate Similarity NPD1203 Approved
0.7717 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD6273 Approved
0.7697 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD4476 Approved
0.7692 Intermediate Similarity NPD4477 Approved
0.7671 Intermediate Similarity NPD2309 Approved
0.7669 Intermediate Similarity NPD17 Approved
0.7669 Intermediate Similarity NPD4626 Approved
0.7667 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD2798 Approved
0.766 Intermediate Similarity NPD1933 Approved
0.7651 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD1471 Phase 3
0.7635 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD1510 Phase 2
0.7622 Intermediate Similarity NPD7033 Discontinued
0.7616 Intermediate Similarity NPD4380 Phase 2
0.7612 Intermediate Similarity NPD3496 Discontinued
0.7603 Intermediate Similarity NPD7003 Approved
0.7597 Intermediate Similarity NPD5535 Approved
0.7597 Intermediate Similarity NPD7768 Phase 2
0.7595 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD1240 Approved
0.7589 Intermediate Similarity NPD2979 Phase 3
0.7586 Intermediate Similarity NPD2424 Discontinued
0.7584 Intermediate Similarity NPD5049 Phase 3
0.7571 Intermediate Similarity NPD411 Approved
0.7569 Intermediate Similarity NPD2438 Suspended
0.7566 Intermediate Similarity NPD5890 Approved
0.7566 Intermediate Similarity NPD5889 Approved
0.7556 Intermediate Similarity NPD1281 Approved
0.7551 Intermediate Similarity NPD2354 Approved
0.7537 Intermediate Similarity NPD1778 Approved
0.7535 Intermediate Similarity NPD447 Suspended
0.7534 Intermediate Similarity NPD2800 Approved
0.7532 Intermediate Similarity NPD3817 Phase 2
0.7519 Intermediate Similarity NPD1894 Discontinued
0.7518 Intermediate Similarity NPD8032 Phase 2
0.7518 Intermediate Similarity NPD6233 Phase 2
0.7516 Intermediate Similarity NPD6279 Approved
0.7516 Intermediate Similarity NPD6280 Approved
0.75 Intermediate Similarity NPD1608 Approved
0.75 Intermediate Similarity NPD9493 Approved
0.7484 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3882 Suspended
0.7483 Intermediate Similarity NPD1607 Approved
0.7466 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7463 Intermediate Similarity NPD1651 Approved
0.746 Intermediate Similarity NPD9697 Approved
0.7453 Intermediate Similarity NPD5844 Phase 1
0.7448 Intermediate Similarity NPD1551 Phase 2
0.7447 Intermediate Similarity NPD1296 Phase 2
0.7436 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD3749 Approved
0.7434 Intermediate Similarity NPD3226 Approved
0.7417 Intermediate Similarity NPD5403 Approved
0.7415 Intermediate Similarity NPD2654 Approved
0.7405 Intermediate Similarity NPD1247 Approved
0.7403 Intermediate Similarity NPD1934 Approved
0.74 Intermediate Similarity NPD5401 Approved
0.74 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD4062 Phase 3
0.7391 Intermediate Similarity NPD1283 Approved
0.7386 Intermediate Similarity NPD6585 Discontinued
0.7365 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD5953 Discontinued
0.7351 Intermediate Similarity NPD2186 Approved
0.7343 Intermediate Similarity NPD4060 Phase 1
0.7333 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5585 Approved
0.7329 Intermediate Similarity NPD2531 Phase 2
0.7324 Intermediate Similarity NPD3764 Approved
0.7324 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD6559 Discontinued
0.7292 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD5124 Phase 1
0.7292 Intermediate Similarity NPD4622 Approved
0.7292 Intermediate Similarity NPD4618 Approved
0.7287 Intermediate Similarity NPD2182 Approved
0.7287 Intermediate Similarity NPD2684 Approved
0.7286 Intermediate Similarity NPD5647 Approved
0.7284 Intermediate Similarity NPD3818 Discontinued
0.7267 Intermediate Similarity NPD7440 Discontinued
0.7266 Intermediate Similarity NPD3225 Approved
0.7255 Intermediate Similarity NPD957 Approved
0.7248 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD4110 Phase 3
0.7248 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD1481 Phase 2
0.7239 Intermediate Similarity NPD7286 Phase 2
0.7239 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD9494 Approved
0.723 Intermediate Similarity NPD2897 Discontinued
0.7226 Intermediate Similarity NPD3847 Discontinued
0.7214 Intermediate Similarity NPD6362 Approved
0.7205 Intermediate Similarity NPD3926 Phase 2
0.7197 Intermediate Similarity NPD7843 Approved
0.7197 Intermediate Similarity NPD5402 Approved
0.7192 Intermediate Similarity NPD7097 Phase 1
0.7192 Intermediate Similarity NPD5688 Approved
0.7192 Intermediate Similarity NPD5689 Approved
0.719 Intermediate Similarity NPD5586 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD6959 Discontinued
0.7185 Intermediate Similarity NPD5536 Phase 2
0.7183 Intermediate Similarity NPD2614 Approved
0.7174 Intermediate Similarity NPD422 Phase 1
0.7174 Intermediate Similarity NPD1535 Discovery
0.7174 Intermediate Similarity NPD1611 Approved
0.7172 Intermediate Similarity NPD230 Phase 1
0.7171 Intermediate Similarity NPD4662 Approved
0.7171 Intermediate Similarity NPD4661 Approved
0.7165 Intermediate Similarity NPD9261 Approved
0.7164 Intermediate Similarity NPD7157 Approved
0.7153 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7229 Phase 3
0.7134 Intermediate Similarity NPD8455 Phase 2
0.7134 Intermediate Similarity NPD2801 Approved
0.7123 Intermediate Similarity NPD6651 Approved
0.7123 Intermediate Similarity NPD6653 Approved
0.7115 Intermediate Similarity NPD6386 Approved
0.7115 Intermediate Similarity NPD6385 Approved
0.7115 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD958 Approved
0.7114 Intermediate Similarity NPD5958 Discontinued
0.7114 Intermediate Similarity NPD4534 Discontinued
0.7113 Intermediate Similarity NPD454 Approved
0.7105 Intermediate Similarity NPD1511 Approved
0.7103 Intermediate Similarity NPD4140 Approved
0.7099 Intermediate Similarity NPD2067 Discontinued
0.7095 Intermediate Similarity NPD2239 Approved
0.7095 Intermediate Similarity NPD2240 Approved
0.7092 Intermediate Similarity NPD1164 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