Structure

Physi-Chem Properties

Molecular Weight:  226.06
Volume:  232.946
LogP:  3.448
LogD:  3.194
LogS:  -5.311
# Rotatable Bonds:  1
TPSA:  43.35
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.596
Synthetic Accessibility Score:  2.737
Fsp3:  0.071
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.77
MDCK Permeability:  1.3616115211334545e-05
Pgp-inhibitor:  0.752
Pgp-substrate:  0.363
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.541
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.006
Plasma Protein Binding (PPB):  84.8000717163086%
Volume Distribution (VD):  1.116
Pgp-substrate:  11.805716514587402%

ADMET: Metabolism

CYP1A2-inhibitor:  0.989
CYP1A2-substrate:  0.631
CYP2C19-inhibitor:  0.484
CYP2C19-substrate:  0.068
CYP2C9-inhibitor:  0.377
CYP2C9-substrate:  0.776
CYP2D6-inhibitor:  0.78
CYP2D6-substrate:  0.849
CYP3A4-inhibitor:  0.734
CYP3A4-substrate:  0.175

ADMET: Excretion

Clearance (CL):  9.233
Half-life (T1/2):  0.404

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.758
Drug-inuced Liver Injury (DILI):  0.958
AMES Toxicity:  0.187
Rat Oral Acute Toxicity:  0.343
Maximum Recommended Daily Dose:  0.781
Skin Sensitization:  0.237
Carcinogencity:  0.898
Eye Corrosion:  0.011
Eye Irritation:  0.502
Respiratory Toxicity:  0.579

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

  Natural Product: NPC313036

Natural Product ID:  NPC313036
Common Name*:   8-Prop-1-En-2-Ylfuro[2,3-H]Chromen-2-One
IUPAC Name:   8-prop-1-en-2-ylfuro[2,3-h]chromen-2-one
Synonyms:  
Standard InCHIKey:  FQCPXIJRWHRHIP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H10O3/c1-8(2)12-7-10-11(16-12)5-3-9-4-6-13(15)17-14(9)10/h3-7H,1H2,2H3
SMILES:  O=c1ccc2c(o1)c1cc(oc1cc2)C(=C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1708543
PubChem CID:   74477
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0000358] Furanocoumarins
          • [CHEMONTID:0002568] Angular furanocoumarins

*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
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. fruit n.a. PMID[10785419]
NPO5129 Tagetes lucida Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[12502312]
NPO12590 Erythrina poeppigiana Species Fabaceae Eukaryota n.a. root n.a. PMID[12803562]
NPO6823 Haemodorum simplex Species Haemodoraceae Eukaryota n.a. n.a. n.a. PMID[19419186]
NPO12590 Erythrina poeppigiana Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19705860]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota fruits n.a. n.a. PMID[22932311]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. fruit n.a. PMID[23721280]
NPO12590 Erythrina poeppigiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12590 Erythrina poeppigiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO900 Cnidium monieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5129 Tagetes lucida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4303 Scirpus tuberosus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8600 Thamnosma texana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12590 Erythrina poeppigiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17910 Russowia sogdiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3917 Desmotes incomparabilis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6823 Haemodorum simplex Species Haemodoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12662 Torilis japonica Species Apiaceae 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
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 18348.9 nM PMID[456994]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 4.6 nM PMID[456994]
NPT156 Individual Protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 25118.9 nM PMID[456994]
NPT920 Individual Protein Alpha-synuclein Homo sapiens Potency n.a. 5011.9 nM PMID[456994]

☑ 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 NPC313036 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
0.9781 High Similarity NPC254010
0.9779 High Similarity NPC262635
0.9577 High Similarity NPC88445
0.9574 High Similarity NPC74539
0.9574 High Similarity NPC304443
0.9571 High Similarity NPC246903
0.951 High Similarity NPC191104
0.9429 High Similarity NPC51146
0.9429 High Similarity NPC166858
0.9371 High Similarity NPC266743
0.9296 High Similarity NPC208584
0.9231 High Similarity NPC190572
0.9178 High Similarity NPC98028
0.9149 High Similarity NPC470856
0.9143 High Similarity NPC36414
0.9137 High Similarity NPC29638
0.9137 High Similarity NPC472516
0.9128 High Similarity NPC269495
0.9122 High Similarity NPC250769
0.9122 High Similarity NPC295608
0.9122 High Similarity NPC278010
0.911 High Similarity NPC155882
0.9091 High Similarity NPC17262
0.9078 High Similarity NPC472515
0.9071 High Similarity NPC253616
0.9071 High Similarity NPC103001
0.9054 High Similarity NPC131725
0.9034 High Similarity NPC198427
0.9007 High Similarity NPC49009
0.9007 High Similarity NPC169
0.9 High Similarity NPC268081
0.9 High Similarity NPC270044
0.898 High Similarity NPC135303
0.898 High Similarity NPC148423
0.8973 High Similarity NPC306788
0.8958 High Similarity NPC225884
0.8947 High Similarity NPC14822
0.8944 High Similarity NPC136095
0.8944 High Similarity NPC473209
0.894 High Similarity NPC244750
0.8912 High Similarity NPC37226
0.8912 High Similarity NPC226644
0.8882 High Similarity NPC303210
0.8882 High Similarity NPC115432
0.8882 High Similarity NPC95472
0.8882 High Similarity NPC260296
0.8882 High Similarity NPC239270
0.8881 High Similarity NPC28337
0.8859 High Similarity NPC130015
0.8859 High Similarity NPC38361
0.8859 High Similarity NPC41326
0.8851 High Similarity NPC472406
0.8851 High Similarity NPC78335
0.8851 High Similarity NPC230713
0.8849 High Similarity NPC229646
0.8844 High Similarity NPC272194
0.8836 High Similarity NPC210826
0.8836 High Similarity NPC51641
0.8836 High Similarity NPC300267
0.8831 High Similarity NPC179464
0.8816 High Similarity NPC33320
0.8808 High Similarity NPC19860
0.8803 High Similarity NPC332594
0.88 High Similarity NPC472462
0.88 High Similarity NPC41719
0.8792 High Similarity NPC170169
0.8792 High Similarity NPC472407
0.8786 High Similarity NPC292998
0.8786 High Similarity NPC247743
0.8784 High Similarity NPC37208
0.8784 High Similarity NPC178202
0.8784 High Similarity NPC221868
0.8776 High Similarity NPC130581
0.8776 High Similarity NPC12148
0.8774 High Similarity NPC204088
0.8774 High Similarity NPC259007
0.8774 High Similarity NPC329215
0.8767 High Similarity NPC155144
0.8766 High Similarity NPC78612
0.8766 High Similarity NPC234536
0.8759 High Similarity NPC53192
0.8758 High Similarity NPC243509
0.8742 High Similarity NPC233776
0.8733 High Similarity NPC263676
0.8718 High Similarity NPC210460
0.8718 High Similarity NPC155264
0.8718 High Similarity NPC193881
0.8718 High Similarity NPC67450
0.8718 High Similarity NPC323137
0.8716 High Similarity NPC135325
0.8714 High Similarity NPC55147
0.871 High Similarity NPC155640
0.8707 High Similarity NPC154217
0.8701 High Similarity NPC216092
0.8699 High Similarity NPC302181
0.8684 High Similarity NPC470625
0.8684 High Similarity NPC13879
0.8681 High Similarity NPC137009
0.8675 High Similarity NPC1477
0.8675 High Similarity NPC213608
0.8675 High Similarity NPC235333
0.8671 High Similarity NPC38153
0.8671 High Similarity NPC157855
0.8667 High Similarity NPC290671
0.8667 High Similarity NPC116604
0.8662 High Similarity NPC151113
0.8658 High Similarity NPC317492
0.8658 High Similarity NPC296030
0.8658 High Similarity NPC39929
0.8649 High Similarity NPC17816
0.8643 High Similarity NPC284424
0.8639 High Similarity NPC196137
0.8639 High Similarity NPC171656
0.8639 High Similarity NPC98926
0.8639 High Similarity NPC230943
0.8639 High Similarity NPC1886
0.863 High Similarity NPC36181
0.8627 High Similarity NPC268360
0.8627 High Similarity NPC65504
0.8621 High Similarity NPC474037
0.8618 High Similarity NPC198490
0.8618 High Similarity NPC213936
0.8618 High Similarity NPC148938
0.8618 High Similarity NPC297531
0.8609 High Similarity NPC5871
0.8601 High Similarity NPC161196
0.8601 High Similarity NPC254741
0.86 High Similarity NPC167576
0.8592 High Similarity NPC66705
0.8591 High Similarity NPC168085
0.8582 High Similarity NPC54503
0.8581 High Similarity NPC470322
0.8581 High Similarity NPC473927
0.8581 High Similarity NPC181388
0.8571 High Similarity NPC87609
0.8571 High Similarity NPC94794
0.8571 High Similarity NPC184702
0.8571 High Similarity NPC112791
0.8571 High Similarity NPC196459
0.8571 High Similarity NPC470296
0.8571 High Similarity NPC188632
0.8562 High Similarity NPC297985
0.8562 High Similarity NPC247677
0.8562 High Similarity NPC24075
0.8562 High Similarity NPC160015
0.8553 High Similarity NPC183874
0.8553 High Similarity NPC72370
0.8551 High Similarity NPC475496
0.8551 High Similarity NPC49852
0.8544 High Similarity NPC320789
0.8543 High Similarity NPC193976
0.8543 High Similarity NPC115324
0.8543 High Similarity NPC23668
0.8542 High Similarity NPC228661
0.8535 High Similarity NPC179015
0.8535 High Similarity NPC173149
0.8533 High Similarity NPC164299
0.8531 High Similarity NPC46869
0.8531 High Similarity NPC104796
0.8523 High Similarity NPC180477
0.8523 High Similarity NPC140120
0.8521 High Similarity NPC108113
0.8521 High Similarity NPC93756
0.8514 High Similarity NPC294365
0.8514 High Similarity NPC469935
0.8514 High Similarity NPC469953
0.8514 High Similarity NPC311741
0.8514 High Similarity NPC178627
0.8514 High Similarity NPC179970
0.8514 High Similarity NPC234629
0.8511 High Similarity NPC175159
0.8511 High Similarity NPC278556
0.8506 High Similarity NPC246647
0.8506 High Similarity NPC296957
0.8506 High Similarity NPC164110
0.8506 High Similarity NPC212967
0.8506 High Similarity NPC260902
0.8506 High Similarity NPC96342
0.8503 High Similarity NPC473042
0.8497 Intermediate Similarity NPC108937
0.8497 Intermediate Similarity NPC469934
0.8497 Intermediate Similarity NPC99199
0.8497 Intermediate Similarity NPC279218
0.8493 Intermediate Similarity NPC270883
0.8493 Intermediate Similarity NPC172986
0.8493 Intermediate Similarity NPC261227
0.8493 Intermediate Similarity NPC472409
0.8493 Intermediate Similarity NPC305355
0.8493 Intermediate Similarity NPC475680
0.8489 Intermediate Similarity NPC473907
0.8487 Intermediate Similarity NPC67654
0.8487 Intermediate Similarity NPC253872
0.8487 Intermediate Similarity NPC142308
0.8487 Intermediate Similarity NPC207624
0.8487 Intermediate Similarity NPC271681
0.8483 Intermediate Similarity NPC17848
0.8483 Intermediate Similarity NPC199458
0.8483 Intermediate Similarity NPC183639
0.8483 Intermediate Similarity NPC201395
0.8477 Intermediate Similarity NPC474660

  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 NPC313036 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
0.9779 High Similarity NPD1243 Approved
0.9574 High Similarity NPD920 Approved
0.9571 High Similarity NPD642 Clinical (unspecified phase)
0.9429 High Similarity NPD643 Clinical (unspecified phase)
0.8816 High Similarity NPD919 Approved
0.8601 High Similarity NPD2796 Approved
0.8506 High Similarity NPD3749 Approved
0.8462 Intermediate Similarity NPD1247 Approved
0.8389 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD3748 Approved
0.8252 Intermediate Similarity NPD1240 Approved
0.82 Intermediate Similarity NPD6799 Approved
0.8194 Intermediate Similarity NPD7819 Suspended
0.8194 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD7411 Suspended
0.8176 Intermediate Similarity NPD2800 Approved
0.8163 Intermediate Similarity NPD2344 Approved
0.8151 Intermediate Similarity NPD1510 Phase 2
0.8146 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8138 Intermediate Similarity NPD1607 Approved
0.8129 Intermediate Similarity NPD6801 Discontinued
0.8112 Intermediate Similarity NPD2313 Discontinued
0.8108 Intermediate Similarity NPD1549 Phase 2
0.805 Intermediate Similarity NPD5494 Approved
0.8041 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD7075 Discontinued
0.8027 Intermediate Similarity NPD2799 Discontinued
0.8 Intermediate Similarity NPD6599 Discontinued
0.8 Intermediate Similarity NPD3750 Approved
0.7987 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD1511 Approved
0.7947 Intermediate Similarity NPD2309 Approved
0.7919 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7911 Intermediate Similarity NPD3817 Phase 2
0.7908 Intermediate Similarity NPD2532 Approved
0.7908 Intermediate Similarity NPD2534 Approved
0.7908 Intermediate Similarity NPD2533 Approved
0.7901 Intermediate Similarity NPD3926 Phase 2
0.7885 Intermediate Similarity NPD4380 Phase 2
0.7862 Intermediate Similarity NPD1296 Phase 2
0.7862 Intermediate Similarity NPD7768 Phase 2
0.7857 Intermediate Similarity NPD1512 Approved
0.7853 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD1551 Phase 2
0.7848 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7847 Intermediate Similarity NPD6832 Phase 2
0.7821 Intermediate Similarity NPD3226 Approved
0.7815 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD9717 Approved
0.78 Intermediate Similarity NPD1471 Phase 3
0.7784 Intermediate Similarity NPD6559 Discontinued
0.7763 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD1203 Approved
0.7758 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD3882 Suspended
0.774 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD2801 Approved
0.7733 Intermediate Similarity NPD2935 Discontinued
0.773 Intermediate Similarity NPD422 Phase 1
0.7708 Intermediate Similarity NPD1019 Discontinued
0.7703 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD2346 Discontinued
0.7677 Intermediate Similarity NPD5401 Approved
0.7673 Intermediate Similarity NPD1934 Approved
0.7651 Intermediate Similarity NPD3818 Discontinued
0.7639 Intermediate Similarity NPD3267 Approved
0.7639 Intermediate Similarity NPD3266 Approved
0.7635 Intermediate Similarity NPD4307 Phase 2
0.7622 Intermediate Similarity NPD6232 Discontinued
0.7619 Intermediate Similarity NPD5953 Discontinued
0.7606 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD7286 Phase 2
0.759 Intermediate Similarity NPD7473 Discontinued
0.7589 Intermediate Similarity NPD17 Approved
0.7584 Intermediate Similarity NPD447 Suspended
0.758 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD5403 Approved
0.7578 Intermediate Similarity NPD5402 Approved
0.7516 Intermediate Similarity NPD1465 Phase 2
0.7515 Intermediate Similarity NPD6808 Phase 2
0.75 Intermediate Similarity NPD5844 Phase 1
0.75 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD4287 Approved
0.7468 Intermediate Similarity NPD2654 Approved
0.7466 Intermediate Similarity NPD2798 Approved
0.7455 Intermediate Similarity NPD6959 Discontinued
0.7453 Intermediate Similarity NPD6280 Approved
0.7453 Intermediate Similarity NPD6279 Approved
0.7434 Intermediate Similarity NPD4308 Phase 3
0.7431 Intermediate Similarity NPD1608 Approved
0.7423 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD2797 Approved
0.7383 Intermediate Similarity NPD411 Approved
0.7383 Intermediate Similarity NPD3268 Approved
0.7362 Intermediate Similarity NPD2296 Approved
0.7351 Intermediate Similarity NPD1933 Approved
0.7338 Intermediate Similarity NPD1241 Discontinued
0.7326 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD4628 Phase 3
0.7305 Intermediate Similarity NPD5710 Approved
0.7305 Intermediate Similarity NPD7229 Phase 3
0.7305 Intermediate Similarity NPD5711 Approved
0.7303 Intermediate Similarity NPD6651 Approved
0.7285 Intermediate Similarity NPD943 Approved
0.7279 Intermediate Similarity NPD1164 Approved
0.7256 Intermediate Similarity NPD4288 Approved
0.7251 Intermediate Similarity NPD1729 Discontinued
0.7237 Intermediate Similarity NPD230 Phase 1
0.7225 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6585 Discontinued
0.7219 Intermediate Similarity NPD2403 Approved
0.7219 Intermediate Similarity NPD6166 Phase 2
0.7219 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD3225 Approved
0.7208 Intermediate Similarity NPD7033 Discontinued
0.7203 Intermediate Similarity NPD9545 Approved
0.7197 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD7054 Approved
0.7192 Intermediate Similarity NPD3972 Approved
0.7183 Intermediate Similarity NPD9493 Approved
0.7178 Intermediate Similarity NPD5890 Approved
0.7178 Intermediate Similarity NPD5889 Approved
0.7152 Intermediate Similarity NPD3764 Approved
0.7151 Intermediate Similarity NPD7074 Phase 3
0.7151 Intermediate Similarity NPD7472 Approved
0.7132 Intermediate Similarity NPD9697 Approved
0.7124 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD5124 Phase 1
0.7123 Intermediate Similarity NPD1281 Approved
0.7115 Intermediate Similarity NPD2353 Approved
0.7115 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD6797 Phase 2
0.7095 Intermediate Similarity NPD1876 Approved
0.7073 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD7251 Discontinued
0.7062 Intermediate Similarity NPD8434 Phase 2
0.7029 Intermediate Similarity NPD7808 Phase 3
0.7024 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD1611 Approved
0.6985 Remote Similarity NPD9261 Approved
0.6981 Remote Similarity NPD7003 Approved
0.698 Remote Similarity NPD1283 Approved
0.6966 Remote Similarity NPD1548 Phase 1
0.6959 Remote Similarity NPD5242 Approved
0.6957 Remote Similarity NPD7390 Discontinued
0.6943 Remote Similarity NPD6099 Approved
0.6943 Remote Similarity NPD6100 Approved
0.694 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6937 Remote Similarity NPD3887 Approved
0.6937 Remote Similarity NPD2354 Approved
0.6928 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6918 Remote Similarity NPD1652 Phase 2
0.6918 Remote Similarity NPD1651 Approved
0.6914 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6901 Remote Similarity NPD5535 Approved
0.6899 Remote Similarity NPD6004 Phase 3
0.6899 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6005 Phase 3
0.6899 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6002 Phase 3
0.6892 Remote Similarity NPD1610 Phase 2
0.6885 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6885 Remote Similarity NPD4361 Phase 2
0.6883 Remote Similarity NPD8032 Phase 2
0.6879 Remote Similarity NPD651 Clinical (unspecified phase)
0.6871 Remote Similarity NPD6273 Approved
0.6871 Remote Similarity NPD5049 Phase 3
0.6852 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6848 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6848 Remote Similarity NPD7458 Discontinued
0.6846 Remote Similarity NPD1481 Phase 2
0.6845 Remote Similarity NPD5353 Approved
0.6842 Remote Similarity NPD7199 Phase 2
0.6839 Remote Similarity NPD3140 Approved
0.6839 Remote Similarity NPD3142 Approved
0.6839 Remote Similarity NPD2979 Phase 3
0.6835 Remote Similarity NPD5405 Approved
0.6835 Remote Similarity NPD5404 Approved
0.6835 Remote Similarity NPD5406 Approved
0.6835 Remote Similarity NPD5408 Approved
0.6835 Remote Similarity NPD4477 Approved
0.6835 Remote Similarity NPD4476 Approved
0.6831 Remote Similarity NPD4363 Phase 3
0.6831 Remote Similarity NPD4360 Phase 2
0.6818 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6818 Remote Similarity NPD1252 Clinical (unspecified phase)
0.6813 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6805 Remote Similarity NPD4947 Clinical (unspecified phase)
0.6803 Remote Similarity NPD5691 Approved
0.6803 Remote Similarity NPD9268 Approved
0.6796 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6795 Remote Similarity NPD6355 Discontinued

  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