Structure

Physi-Chem Properties

Molecular Weight:  338.12
Volume:  343.11
LogP:  4.566
LogD:  2.834
LogS:  -3.96
# Rotatable Bonds:  1
TPSA:  79.9
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.703
Synthetic Accessibility Score:  3.291
Fsp3:  0.25
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:  -4.72
MDCK Permeability:  1.4338309483719058e-05
Pgp-inhibitor:  0.09
Pgp-substrate:  0.021
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.471

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.018
Plasma Protein Binding (PPB):  98.77440643310547%
Volume Distribution (VD):  0.48
Pgp-substrate:  2.7140486240386963%

ADMET: Metabolism

CYP1A2-inhibitor:  0.923
CYP1A2-substrate:  0.609
CYP2C19-inhibitor:  0.886
CYP2C19-substrate:  0.08
CYP2C9-inhibitor:  0.831
CYP2C9-substrate:  0.913
CYP2D6-inhibitor:  0.61
CYP2D6-substrate:  0.716
CYP3A4-inhibitor:  0.351
CYP3A4-substrate:  0.482

ADMET: Excretion

Clearance (CL):  3.059
Half-life (T1/2):  0.349

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.093
Drug-inuced Liver Injury (DILI):  0.773
AMES Toxicity:  0.255
Rat Oral Acute Toxicity:  0.177
Maximum Recommended Daily Dose:  0.617
Skin Sensitization:  0.802
Carcinogencity:  0.341
Eye Corrosion:  0.003
Eye Irritation:  0.882
Respiratory Toxicity:  0.516

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

  Natural Product: NPC476185

Natural Product ID:  NPC476185
Common Name*:   4-Hydroxy-7-(4-Hydroxyphenyl)-2,3,3-Trimethyl-2H-Furo[3,2-G]Chromen-5-One
IUPAC Name:   4-hydroxy-7-(4-hydroxyphenyl)-2,3,3-trimethyl-2H-furo[3,2-g]chromen-5-one
Synonyms:  
Standard InCHIKey:  YPVUORZILHLSOT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H18O5/c1-10-20(2,3)18-16(24-10)9-15-17(19(18)23)13(22)8-14(25-15)11-4-6-12(21)7-5-11/h4-10,21,23H,1-3H3
SMILES:  CC1C(C2=C(O1)C=C3C(=C2O)C(=O)C=C(O3)C4=CC=C(C=C4)O)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL551658
PubChem CID:   45270713
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones
          • [CHEMONTID:0001759] Furanoflavones

*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
NPO11959 Helminthostachys zeylanica Species Ophioglossaceae Eukaryota rhizomes n.a. n.a. PMID[19583252]
NPO11959 Helminthostachys zeylanica Species Ophioglossaceae Eukaryota Rhizomes n.a. n.a. PMID[28169537]
NPO11959 Helminthostachys zeylanica Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11959 Helminthostachys zeylanica Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11959 Helminthostachys zeylanica Species Ophioglossaceae 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
NPT65 Cell Line HepG2 Homo sapiens IC50 > 10000.0 nM PMID[479659]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[479659]

☑ 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 NPC476185 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 NPC321896
0.9722 High Similarity NPC168085
0.9655 High Similarity NPC317492
0.9653 High Similarity NPC300988
0.9653 High Similarity NPC10990
0.958 High Similarity NPC11700
0.9524 High Similarity NPC471675
0.9521 High Similarity NPC471114
0.9514 High Similarity NPC224714
0.947 High Similarity NPC476283
0.9459 High Similarity NPC476238
0.9459 High Similarity NPC327269
0.9459 High Similarity NPC31627
0.9448 High Similarity NPC472629
0.9392 High Similarity NPC290671
0.9392 High Similarity NPC472636
0.9388 High Similarity NPC5173
0.9384 High Similarity NPC473077
0.9384 High Similarity NPC296998
0.9384 High Similarity NPC308200
0.9379 High Similarity NPC87486
0.9379 High Similarity NPC124780
0.9379 High Similarity NPC216538
0.9379 High Similarity NPC319752
0.9379 High Similarity NPC476055
0.9379 High Similarity NPC470890
0.9379 High Similarity NPC271288
0.9379 High Similarity NPC273538
0.9375 High Similarity NPC166934
0.9375 High Similarity NPC220998
0.9375 High Similarity NPC37496
0.9375 High Similarity NPC64915
0.9375 High Similarity NPC167624
0.9375 High Similarity NPC107572
0.9375 High Similarity NPC227579
0.9375 High Similarity NPC10937
0.9375 High Similarity NPC40833
0.9375 High Similarity NPC223500
0.9375 High Similarity NPC76338
0.9375 High Similarity NPC177354
0.9375 High Similarity NPC1089
0.9375 High Similarity NPC265040
0.9375 High Similarity NPC78
0.9375 High Similarity NPC166482
0.9375 High Similarity NPC76372
0.9375 High Similarity NPC324436
0.9375 High Similarity NPC161506
0.9375 High Similarity NPC32739
0.9375 High Similarity NPC66515
0.9375 High Similarity NPC328164
0.9375 High Similarity NPC306829
0.9375 High Similarity NPC194432
0.9375 High Similarity NPC148757
0.9375 High Similarity NPC125855
0.9375 High Similarity NPC296917
0.9375 High Similarity NPC228504
0.9375 High Similarity NPC324134
0.9375 High Similarity NPC182852
0.9371 High Similarity NPC159275
0.9371 High Similarity NPC241100
0.9338 High Similarity NPC196448
0.9329 High Similarity NPC285623
0.9329 High Similarity NPC473996
0.9324 High Similarity NPC472421
0.9324 High Similarity NPC472633
0.9324 High Similarity NPC29777
0.9324 High Similarity NPC61258
0.9324 High Similarity NPC37348
0.9324 High Similarity NPC471115
0.9324 High Similarity NPC188403
0.932 High Similarity NPC145467
0.932 High Similarity NPC39195
0.9315 High Similarity NPC142405
0.9315 High Similarity NPC54577
0.9315 High Similarity NPC267375
0.9315 High Similarity NPC312973
0.9315 High Similarity NPC24136
0.9315 High Similarity NPC475052
0.9315 High Similarity NPC83357
0.9315 High Similarity NPC178343
0.9315 High Similarity NPC474161
0.9315 High Similarity NPC67805
0.9315 High Similarity NPC306488
0.9315 High Similarity NPC246948
0.9315 High Similarity NPC301276
0.9315 High Similarity NPC111786
0.9315 High Similarity NPC187282
0.9315 High Similarity NPC476088
0.9315 High Similarity NPC20488
0.9315 High Similarity NPC290133
0.9315 High Similarity NPC195621
0.9315 High Similarity NPC176229
0.9315 High Similarity NPC5820
0.9315 High Similarity NPC124729
0.9315 High Similarity NPC88964
0.9315 High Similarity NPC214774
0.9315 High Similarity NPC470647
0.931 High Similarity NPC278249
0.931 High Similarity NPC214166
0.931 High Similarity NPC75049
0.931 High Similarity NPC81697
0.931 High Similarity NPC68104
0.931 High Similarity NPC125894
0.931 High Similarity NPC257097
0.931 High Similarity NPC85162
0.931 High Similarity NPC169591
0.931 High Similarity NPC185276
0.931 High Similarity NPC77794
0.931 High Similarity NPC316816
0.931 High Similarity NPC150408
0.931 High Similarity NPC190637
0.931 High Similarity NPC149026
0.931 High Similarity NPC476178
0.931 High Similarity NPC164980
0.931 High Similarity NPC39329
0.931 High Similarity NPC212932
0.931 High Similarity NPC293053
0.931 High Similarity NPC221432
0.931 High Similarity NPC475705
0.931 High Similarity NPC117836
0.931 High Similarity NPC9117
0.931 High Similarity NPC91560
0.931 High Similarity NPC143896
0.931 High Similarity NPC175504
0.931 High Similarity NPC51887
0.931 High Similarity NPC107177
0.931 High Similarity NPC478086
0.931 High Similarity NPC24821
0.931 High Similarity NPC223812
0.931 High Similarity NPC310130
0.9306 High Similarity NPC110969
0.9306 High Similarity NPC110038
0.9306 High Similarity NPC258630
0.9306 High Similarity NPC282300
0.9306 High Similarity NPC96408
0.9306 High Similarity NPC248372
0.9306 High Similarity NPC469404
0.9306 High Similarity NPC213322
0.9306 High Similarity NPC324386
0.9306 High Similarity NPC4743
0.9306 High Similarity NPC156190
0.9306 High Similarity NPC17170
0.9306 High Similarity NPC312391
0.9306 High Similarity NPC166689
0.9306 High Similarity NPC279650
0.9301 High Similarity NPC78913
0.9301 High Similarity NPC217186
0.9301 High Similarity NPC96565
0.9301 High Similarity NPC301217
0.9301 High Similarity NPC216978
0.9301 High Similarity NPC303633
0.9301 High Similarity NPC53181
0.9301 High Similarity NPC220062
0.9301 High Similarity NPC55018
0.9301 High Similarity NPC18260
0.9281 High Similarity NPC187354
0.9267 High Similarity NPC213608
0.9267 High Similarity NPC1477
0.9262 High Similarity NPC472580
0.9262 High Similarity NPC474744
0.9262 High Similarity NPC472423
0.9262 High Similarity NPC474772
0.9257 High Similarity NPC473016
0.9257 High Similarity NPC470461
0.9252 High Similarity NPC104406
0.9252 High Similarity NPC97716
0.9252 High Similarity NPC201731
0.9252 High Similarity NPC23728
0.9252 High Similarity NPC79469
0.9252 High Similarity NPC237635
0.9252 High Similarity NPC283234
0.9252 High Similarity NPC24673
0.9252 High Similarity NPC110303
0.9247 High Similarity NPC326500
0.9247 High Similarity NPC473014
0.9247 High Similarity NPC473015
0.9247 High Similarity NPC234629
0.9247 High Similarity NPC197252
0.9247 High Similarity NPC311741
0.9247 High Similarity NPC209040
0.9247 High Similarity NPC473013
0.9247 High Similarity NPC235217
0.9247 High Similarity NPC311144
0.9247 High Similarity NPC131568
0.9247 High Similarity NPC236766
0.9247 High Similarity NPC131579
0.9241 High Similarity NPC200694
0.9241 High Similarity NPC226636
0.9241 High Similarity NPC473042
0.9241 High Similarity NPC11561
0.9236 High Similarity NPC188243
0.9236 High Similarity NPC215311
0.9236 High Similarity NPC172250
0.9236 High Similarity NPC6407
0.9236 High Similarity NPC80962
0.9236 High Similarity NPC219917
0.9236 High Similarity NPC270883
0.9236 High Similarity NPC150522
0.9236 High Similarity NPC259166
0.9236 High Similarity NPC144118

  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 NPC476185 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
0.9379 High Similarity NPD4378 Clinical (unspecified phase)
0.9028 High Similarity NPD1552 Clinical (unspecified phase)
0.9028 High Similarity NPD1550 Clinical (unspecified phase)
0.9013 High Similarity NPD2393 Clinical (unspecified phase)
0.8966 High Similarity NPD1549 Phase 2
0.8958 High Similarity NPD2796 Approved
0.8954 High Similarity NPD8443 Clinical (unspecified phase)
0.894 High Similarity NPD4380 Phase 2
0.8904 High Similarity NPD2800 Approved
0.8889 High Similarity NPD1510 Phase 2
0.8859 High Similarity NPD7410 Clinical (unspecified phase)
0.8718 High Similarity NPD7075 Discontinued
0.8701 High Similarity NPD1934 Approved
0.8645 High Similarity NPD7819 Suspended
0.8645 High Similarity NPD7096 Clinical (unspecified phase)
0.8636 High Similarity NPD7411 Suspended
0.8611 High Similarity NPD1240 Approved
0.8599 High Similarity NPD4381 Clinical (unspecified phase)
0.8581 High Similarity NPD6801 Discontinued
0.8553 High Similarity NPD6959 Discontinued
0.8543 High Similarity NPD1511 Approved
0.8526 High Similarity NPD2801 Approved
0.8493 Intermediate Similarity NPD1607 Approved
0.8491 Intermediate Similarity NPD5494 Approved
0.8466 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD6599 Discontinued
0.8431 Intermediate Similarity NPD1512 Approved
0.8418 Intermediate Similarity NPD7768 Phase 2
0.8418 Intermediate Similarity NPD3882 Suspended
0.8405 Intermediate Similarity NPD3818 Discontinued
0.8395 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8377 Intermediate Similarity NPD920 Approved
0.8373 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.8366 Intermediate Similarity NPD2533 Approved
0.8366 Intermediate Similarity NPD2532 Approved
0.8366 Intermediate Similarity NPD2534 Approved
0.8344 Intermediate Similarity NPD3750 Approved
0.8301 Intermediate Similarity NPD6799 Approved
0.8282 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8282 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8282 Intermediate Similarity NPD6166 Phase 2
0.8278 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8278 Intermediate Similarity NPD1243 Approved
0.825 Intermediate Similarity NPD3749 Approved
0.8247 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8243 Intermediate Similarity NPD6651 Approved
0.8239 Intermediate Similarity NPD3817 Phase 2
0.8235 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8212 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD6559 Discontinued
0.8146 Intermediate Similarity NPD2344 Approved
0.8133 Intermediate Similarity NPD7054 Approved
0.8105 Intermediate Similarity NPD4628 Phase 3
0.8095 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8084 Intermediate Similarity NPD7074 Phase 3
0.8084 Intermediate Similarity NPD7472 Approved
0.8079 Intermediate Similarity NPD2935 Discontinued
0.8079 Intermediate Similarity NPD1551 Phase 2
0.8049 Intermediate Similarity NPD6232 Discontinued
0.8036 Intermediate Similarity NPD6797 Phase 2
0.8025 Intermediate Similarity NPD5403 Approved
0.8013 Intermediate Similarity NPD3748 Approved
0.8013 Intermediate Similarity NPD2799 Discontinued
0.8012 Intermediate Similarity NPD7473 Discontinued
0.7988 Intermediate Similarity NPD7251 Discontinued
0.7973 Intermediate Similarity NPD2313 Discontinued
0.7973 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD6100 Approved
0.7961 Intermediate Similarity NPD6099 Approved
0.7941 Intermediate Similarity NPD7808 Phase 3
0.7935 Intermediate Similarity NPD2309 Approved
0.7929 Intermediate Similarity NPD5953 Discontinued
0.7917 Intermediate Similarity NPD5844 Phase 1
0.7917 Intermediate Similarity NPD7286 Phase 2
0.7901 Intermediate Similarity NPD5402 Approved
0.7898 Intermediate Similarity NPD5401 Approved
0.7898 Intermediate Similarity NPD4360 Phase 2
0.7898 Intermediate Similarity NPD4363 Phase 3
0.7895 Intermediate Similarity NPD7033 Discontinued
0.7879 Intermediate Similarity NPD1247 Approved
0.7871 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD919 Approved
0.7853 Intermediate Similarity NPD4361 Phase 2
0.7853 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD4908 Phase 1
0.7836 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD3226 Approved
0.7785 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD3268 Approved
0.7725 Intermediate Similarity NPD5710 Approved
0.7725 Intermediate Similarity NPD5711 Approved
0.7724 Intermediate Similarity NPD1610 Phase 2
0.7724 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD7390 Discontinued
0.7703 Intermediate Similarity NPD2798 Approved
0.7692 Intermediate Similarity NPD1548 Phase 1
0.7679 Intermediate Similarity NPD3926 Phase 2
0.7677 Intermediate Similarity NPD2346 Discontinued
0.7635 Intermediate Similarity NPD2797 Approved
0.7635 Intermediate Similarity NPD1203 Approved
0.7622 Intermediate Similarity NPD5760 Phase 2
0.7622 Intermediate Similarity NPD5761 Phase 2
0.7619 Intermediate Similarity NPD7229 Phase 3
0.7607 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD6832 Phase 2
0.7593 Intermediate Similarity NPD7458 Discontinued
0.7582 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD5124 Phase 1
0.758 Intermediate Similarity NPD2654 Approved
0.7564 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD1729 Discontinued
0.7557 Intermediate Similarity NPD8434 Phase 2
0.7551 Intermediate Similarity NPD3972 Approved
0.7516 Intermediate Similarity NPD943 Approved
0.7514 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD422 Phase 1
0.7469 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD6002 Phase 3
0.7452 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD6005 Phase 3
0.7452 Intermediate Similarity NPD6004 Phase 3
0.7452 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD4308 Phase 3
0.7434 Intermediate Similarity NPD4625 Phase 3
0.7432 Intermediate Similarity NPD9717 Approved
0.7421 Intermediate Similarity NPD7003 Approved
0.7417 Intermediate Similarity NPD2861 Phase 2
0.741 Intermediate Similarity NPD1465 Phase 2
0.7407 Intermediate Similarity NPD6273 Approved
0.7403 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD1613 Approved
0.74 Intermediate Similarity NPD3266 Approved
0.74 Intermediate Similarity NPD3267 Approved
0.7389 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD3764 Approved
0.7378 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD4288 Approved
0.7365 Intermediate Similarity NPD2296 Approved
0.7355 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6355 Discontinued
0.7353 Intermediate Similarity NPD7199 Phase 2
0.7349 Intermediate Similarity NPD37 Approved
0.7342 Intermediate Similarity NPD1471 Phase 3
0.734 Intermediate Similarity NPD7584 Approved
0.7337 Intermediate Similarity NPD6234 Discontinued
0.7333 Intermediate Similarity NPD3225 Approved
0.7326 Intermediate Similarity NPD2403 Approved
0.7321 Intermediate Similarity NPD4966 Approved
0.7321 Intermediate Similarity NPD4965 Approved
0.7321 Intermediate Similarity NPD4967 Phase 2
0.7315 Intermediate Similarity NPD1608 Approved
0.7297 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD2424 Discontinued
0.7288 Intermediate Similarity NPD8312 Approved
0.7288 Intermediate Similarity NPD8313 Approved
0.7284 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD4287 Approved
0.7273 Intermediate Similarity NPD3658 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6798 Discontinued
0.7273 Intermediate Similarity NPD6104 Discontinued
0.7267 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD1201 Approved
0.7246 Intermediate Similarity NPD6844 Discontinued
0.7246 Intermediate Similarity NPD6279 Approved
0.7246 Intermediate Similarity NPD6280 Approved
0.7244 Intermediate Similarity NPD230 Phase 1
0.7241 Intermediate Similarity NPD3751 Discontinued
0.7211 Intermediate Similarity NPD9545 Approved
0.7209 Intermediate Similarity NPD6808 Phase 2
0.7209 Intermediate Similarity NPD3787 Discontinued
0.7208 Intermediate Similarity NPD3027 Phase 3
0.7202 Intermediate Similarity NPD8455 Phase 2
0.719 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD5890 Approved
0.7186 Intermediate Similarity NPD5889 Approved
0.7182 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD4307 Phase 2
0.7171 Intermediate Similarity NPD1470 Approved
0.7171 Intermediate Similarity NPD1164 Approved
0.717 Intermediate Similarity NPD5405 Approved
0.717 Intermediate Similarity NPD5406 Approved
0.717 Intermediate Similarity NPD5408 Approved
0.717 Intermediate Similarity NPD4476 Approved
0.717 Intermediate Similarity NPD4477 Approved
0.717 Intermediate Similarity NPD5404 Approved
0.7162 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD1296 Phase 2
0.7161 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD4749 Approved
0.7143 Intermediate Similarity NPD1652 Phase 2
0.7134 Intermediate Similarity NPD447 Suspended
0.7134 Intermediate Similarity NPD1933 Approved
0.7126 Intermediate Similarity NPD7784 Clinical (unspecified phase)

  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