Structure

Physi-Chem Properties

Molecular Weight:  526.13
Volume:  518.299
LogP:  5.229
LogD:  2.93
LogS:  -4.77
# Rotatable Bonds:  3
TPSA:  160.82
# H-Bond Aceptor:  9
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.18
Synthetic Accessibility Score:  3.52
Fsp3:  0.1
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.114
MDCK Permeability:  7.473904588550795e-06
Pgp-inhibitor:  0.039
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.593
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.005
Plasma Protein Binding (PPB):  97.92835998535156%
Volume Distribution (VD):  0.403
Pgp-substrate:  2.015838623046875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.627
CYP1A2-substrate:  0.13
CYP2C19-inhibitor:  0.84
CYP2C19-substrate:  0.041
CYP2C9-inhibitor:  0.731
CYP2C9-substrate:  0.972
CYP2D6-inhibitor:  0.135
CYP2D6-substrate:  0.726
CYP3A4-inhibitor:  0.254
CYP3A4-substrate:  0.096

ADMET: Excretion

Clearance (CL):  6.792
Half-life (T1/2):  0.667

ADMET: Toxicity

hERG Blockers:  0.096
Human Hepatotoxicity (H-HT):  0.362
Drug-inuced Liver Injury (DILI):  0.984
AMES Toxicity:  0.727
Rat Oral Acute Toxicity:  0.391
Maximum Recommended Daily Dose:  0.63
Skin Sensitization:  0.904
Carcinogencity:  0.064
Eye Corrosion:  0.003
Eye Irritation:  0.903
Respiratory Toxicity:  0.055

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

  Natural Product: NPC174086

Natural Product ID:  NPC174086
Common Name*:   3-[(2S)-5,7-Dihydroxy-2-(4-Hydroxyphenyl)-3,4-Dihydro-2H-Chromen-8-Yl]-5,7-Dihydroxy-2-(4-Hydroxyphenyl)Chromen-4-One
IUPAC Name:   3-[(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:  
Standard InCHIKey:  KBUYUAWZPKKJRC-QHCPKHFHSA-N
Standard InCHI:  InChI=1S/C30H22O9/c31-16-5-1-14(2-6-16)23-10-9-19-20(34)13-22(36)26(30(19)38-23)27-28(37)25-21(35)11-18(33)12-24(25)39-29(27)15-3-7-17(32)8-4-15/h1-8,11-13,23,31-36H,9-10H2/t23-/m0/s1
SMILES:  Oc1ccc(cc1)[C@@H]1CCc2c(O1)c(c(cc2O)O)c1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1433872
PubChem CID:   13941113
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22494026]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. root n.a. PMID[24156713]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[32997496]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. Database[FooDB]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18393 Eugenia sandwicensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16416 Serratula strangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10882 Acer caudatifolium Species Aceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12376 Baccharis macraei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17558 Cynoglossum formosanum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7037 Rumohra adiantiformis Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18393 Eugenia sandwicensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17135 Mikania goyazensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16416 Serratula strangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18247 Globicephala melas Species Delphinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19406 Chrysanthemum leptophyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13505 Grateloupia livida Species Halymeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19479 Trametes feei Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14015 Salacia cordata Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15287 Vernonia megapotamica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10705 Marshallia graminifolia Species Asteraceae 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
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 56234.1 nM PMID[544303]
NPT443 Individual Protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 39810.7 nM PMID[544303]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 19952.6 nM PMID[544303]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 35481.3 nM PMID[544303]
NPT2966 Individual Protein T-complex protein 1 subunit beta Macaaca fascicularis Potency n.a. 35481.3 nM PMID[544303]
NPT156 Individual Protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 89125.1 nM PMID[544303]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 12589.3 nM PMID[544303]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 5173.5 nM PMID[544303]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 20596.2 nM PMID[544303]
NPT864 Individual Protein Lethal(3)malignant brain tumor-like protein 1 Homo sapiens Potency = 15848.9 nM PMID[544303]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 39810.7 nM PMID[544303]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 89125.1 nM PMID[544303]
NPT9 Individual Protein DNA polymerase eta Homo sapiens Potency n.a. 56234.1 nM PMID[544303]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 31622.8 nM PMID[544303]

☑ 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 NPC174086 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
0.9797 High Similarity NPC32867
0.973 High Similarity NPC182555
0.973 High Similarity NPC66441
0.9724 High Similarity NPC122894
0.9667 High Similarity NPC295090
0.9664 High Similarity NPC69531
0.9658 High Similarity NPC291746
0.9658 High Similarity NPC3642
0.9658 High Similarity NPC288840
0.9597 High Similarity NPC134171
0.9597 High Similarity NPC300668
0.9595 High Similarity NPC208011
0.9595 High Similarity NPC39154
0.9595 High Similarity NPC78324
0.9595 High Similarity NPC115601
0.953 High Similarity NPC121568
0.9517 High Similarity NPC470136
0.9517 High Similarity NPC470135
0.9517 High Similarity NPC39045
0.947 High Similarity NPC257166
0.947 High Similarity NPC1796
0.947 High Similarity NPC475184
0.9467 High Similarity NPC258474
0.9467 High Similarity NPC201227
0.9452 High Similarity NPC470133
0.9452 High Similarity NPC470131
0.9452 High Similarity NPC473078
0.9452 High Similarity NPC470132
0.9452 High Similarity NPC109183
0.9452 High Similarity NPC228779
0.9452 High Similarity NPC470134
0.9408 High Similarity NPC105584
0.9408 High Similarity NPC123544
0.9408 High Similarity NPC51247
0.9408 High Similarity NPC51760
0.9408 High Similarity NPC15815
0.9404 High Similarity NPC198489
0.9404 High Similarity NPC309648
0.9404 High Similarity NPC61112
0.94 High Similarity NPC290830
0.94 High Similarity NPC303485
0.94 High Similarity NPC71061
0.94 High Similarity NPC194593
0.94 High Similarity NPC72425
0.9396 High Similarity NPC67322
0.9396 High Similarity NPC222713
0.9396 High Similarity NPC138299
0.9396 High Similarity NPC111112
0.9392 High Similarity NPC132345
0.9388 High Similarity NPC473077
0.9388 High Similarity NPC296998
0.9346 High Similarity NPC98023
0.9346 High Similarity NPC121647
0.9346 High Similarity NPC226462
0.9346 High Similarity NPC42965
0.9346 High Similarity NPC195136
0.9342 High Similarity NPC271741
0.9342 High Similarity NPC318527
0.9342 High Similarity NPC323627
0.9342 High Similarity NPC324358
0.9342 High Similarity NPC322459
0.9342 High Similarity NPC287789
0.9338 High Similarity NPC79375
0.9338 High Similarity NPC121649
0.9338 High Similarity NPC248739
0.9338 High Similarity NPC205026
0.9338 High Similarity NPC159707
0.9338 High Similarity NPC150908
0.9338 High Similarity NPC37253
0.9338 High Similarity NPC215203
0.9338 High Similarity NPC158027
0.9338 High Similarity NPC186227
0.9338 High Similarity NPC52611
0.9338 High Similarity NPC14606
0.9338 High Similarity NPC265624
0.9338 High Similarity NPC100049
0.9324 High Similarity NPC161191
0.932 High Similarity NPC54577
0.932 High Similarity NPC88964
0.932 High Similarity NPC246948
0.932 High Similarity NPC267375
0.932 High Similarity NPC475052
0.932 High Similarity NPC111786
0.932 High Similarity NPC142405
0.932 High Similarity NPC83357
0.932 High Similarity NPC301276
0.932 High Similarity NPC312973
0.932 High Similarity NPC470647
0.932 High Similarity NPC214774
0.932 High Similarity NPC20488
0.932 High Similarity NPC67805
0.932 High Similarity NPC195621
0.932 High Similarity NPC176229
0.931 High Similarity NPC14871
0.9295 High Similarity NPC171985
0.9295 High Similarity NPC320741
0.929 High Similarity NPC38591
0.929 High Similarity NPC63438
0.9286 High Similarity NPC301256
0.9286 High Similarity NPC312273
0.9272 High Similarity NPC109594
0.9272 High Similarity NPC326592
0.9272 High Similarity NPC112701
0.9267 High Similarity NPC316960
0.9267 High Similarity NPC477897
0.9267 High Similarity NPC204561
0.9267 High Similarity NPC78835
0.9267 High Similarity NPC317715
0.9267 High Similarity NPC328740
0.9267 High Similarity NPC309512
0.9267 High Similarity NPC289774
0.9267 High Similarity NPC178484
0.9267 High Similarity NPC209846
0.9267 High Similarity NPC148945
0.9257 High Similarity NPC23728
0.9257 High Similarity NPC283234
0.9257 High Similarity NPC110303
0.9252 High Similarity NPC319752
0.9247 High Similarity NPC306829
0.9247 High Similarity NPC166482
0.9247 High Similarity NPC194432
0.9247 High Similarity NPC265040
0.9247 High Similarity NPC161506
0.9247 High Similarity NPC148757
0.9247 High Similarity NPC125855
0.9247 High Similarity NPC296917
0.9247 High Similarity NPC228504
0.9247 High Similarity NPC182852
0.9247 High Similarity NPC66515
0.9247 High Similarity NPC223500
0.9247 High Similarity NPC220998
0.9247 High Similarity NPC177354
0.9247 High Similarity NPC64915
0.9247 High Similarity NPC107572
0.9247 High Similarity NPC227579
0.9247 High Similarity NPC76372
0.9247 High Similarity NPC324134
0.9247 High Similarity NPC166934
0.9247 High Similarity NPC1089
0.9247 High Similarity NPC37496
0.9247 High Similarity NPC324436
0.9247 High Similarity NPC167624
0.9247 High Similarity NPC40833
0.9247 High Similarity NPC10937
0.9247 High Similarity NPC76338
0.9247 High Similarity NPC78
0.9247 High Similarity NPC32739
0.9247 High Similarity NPC328164
0.9226 High Similarity NPC473011
0.9226 High Similarity NPC473012
0.9216 High Similarity NPC208258
0.9211 High Similarity NPC254351
0.9205 High Similarity NPC161881
0.9205 High Similarity NPC56232
0.9205 High Similarity NPC10807
0.9205 High Similarity NPC244583
0.9205 High Similarity NPC150123
0.92 High Similarity NPC472633
0.92 High Similarity NPC29777
0.92 High Similarity NPC471115
0.9195 High Similarity NPC132592
0.9195 High Similarity NPC160821
0.9195 High Similarity NPC266572
0.9195 High Similarity NPC189087
0.9195 High Similarity NPC321623
0.9189 High Similarity NPC474161
0.9189 High Similarity NPC472629
0.9189 High Similarity NPC476088
0.9184 High Similarity NPC125894
0.9184 High Similarity NPC310130
0.9184 High Similarity NPC68104
0.9184 High Similarity NPC77794
0.9184 High Similarity NPC85162
0.9184 High Similarity NPC221432
0.9184 High Similarity NPC257097
0.9184 High Similarity NPC164980
0.9184 High Similarity NPC478086
0.9184 High Similarity NPC278249
0.9184 High Similarity NPC175504
0.9184 High Similarity NPC149026
0.9184 High Similarity NPC39329
0.9184 High Similarity NPC91560
0.9184 High Similarity NPC185276
0.9184 High Similarity NPC150408
0.9184 High Similarity NPC75049
0.9184 High Similarity NPC143896
0.9184 High Similarity NPC81697
0.9184 High Similarity NPC219915
0.9184 High Similarity NPC223812
0.9184 High Similarity NPC107177
0.9184 High Similarity NPC316816
0.9184 High Similarity NPC214166
0.9184 High Similarity NPC169591
0.9178 High Similarity NPC17170
0.9178 High Similarity NPC248372
0.9178 High Similarity NPC110038
0.9178 High Similarity NPC166689
0.9178 High Similarity NPC4743
0.9178 High Similarity NPC26238
0.9178 High Similarity NPC213322

  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 NPC174086 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
0.9211 High Similarity NPD8443 Clinical (unspecified phase)
0.9122 High Similarity NPD7410 Clinical (unspecified phase)
0.9073 High Similarity NPD4380 Phase 2
0.9038 High Similarity NPD6959 Discontinued
0.9034 High Similarity NPD1550 Clinical (unspecified phase)
0.9034 High Similarity NPD1552 Clinical (unspecified phase)
0.9013 High Similarity NPD7411 Suspended
0.8993 High Similarity NPD4378 Clinical (unspecified phase)
0.8987 High Similarity NPD7852 Clinical (unspecified phase)
0.8973 High Similarity NPD1549 Phase 2
0.8774 High Similarity NPD2393 Clinical (unspecified phase)
0.8767 High Similarity NPD1510 Phase 2
0.8726 High Similarity NPD7075 Discontinued
0.8726 High Similarity NPD4381 Clinical (unspecified phase)
0.8707 High Similarity NPD2796 Approved
0.8662 High Similarity NPD7768 Phase 2
0.8634 High Similarity NPD6167 Clinical (unspecified phase)
0.8634 High Similarity NPD6166 Phase 2
0.8634 High Similarity NPD6168 Clinical (unspecified phase)
0.8589 High Similarity NPD7804 Clinical (unspecified phase)
0.8535 High Similarity NPD7819 Suspended
0.8535 High Similarity NPD7096 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD3749 Approved
0.8471 Intermediate Similarity NPD6801 Discontinued
0.8471 Intermediate Similarity NPD1934 Approved
0.8428 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8367 Intermediate Similarity NPD1240 Approved
0.8312 Intermediate Similarity NPD1511 Approved
0.8302 Intermediate Similarity NPD2801 Approved
0.8289 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8255 Intermediate Similarity NPD1607 Approved
0.8253 Intermediate Similarity NPD7054 Approved
0.8235 Intermediate Similarity NPD3750 Approved
0.8205 Intermediate Similarity NPD1512 Approved
0.8204 Intermediate Similarity NPD7074 Phase 3
0.8204 Intermediate Similarity NPD7472 Approved
0.8193 Intermediate Similarity NPD3818 Discontinued
0.816 Intermediate Similarity NPD5494 Approved
0.8155 Intermediate Similarity NPD6797 Phase 2
0.8153 Intermediate Similarity NPD5403 Approved
0.8108 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8107 Intermediate Similarity NPD7251 Discontinued
0.8086 Intermediate Similarity NPD3882 Suspended
0.8077 Intermediate Similarity NPD6799 Approved
0.8077 Intermediate Similarity NPD7390 Discontinued
0.8061 Intermediate Similarity NPD6232 Discontinued
0.8059 Intermediate Similarity NPD7808 Phase 3
0.8059 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8052 Intermediate Similarity NPD2800 Approved
0.8025 Intermediate Similarity NPD5401 Approved
0.8025 Intermediate Similarity NPD3817 Phase 2
0.8025 Intermediate Similarity NPD5402 Approved
0.8024 Intermediate Similarity NPD7473 Discontinued
0.8 Intermediate Similarity NPD6559 Discontinued
0.7974 Intermediate Similarity NPD1551 Phase 2
0.7973 Intermediate Similarity NPD4908 Phase 1
0.7941 Intermediate Similarity NPD5953 Discontinued
0.7929 Intermediate Similarity NPD5844 Phase 1
0.7925 Intermediate Similarity NPD920 Approved
0.7911 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD3748 Approved
0.7907 Intermediate Similarity NPD8313 Approved
0.7907 Intermediate Similarity NPD8312 Approved
0.7898 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD6651 Approved
0.7888 Intermediate Similarity NPD6599 Discontinued
0.7871 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD2313 Discontinued
0.7867 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD1243 Approved
0.7806 Intermediate Similarity NPD2344 Approved
0.7799 Intermediate Similarity NPD2533 Approved
0.7799 Intermediate Similarity NPD2534 Approved
0.7799 Intermediate Similarity NPD2532 Approved
0.7792 Intermediate Similarity NPD2799 Discontinued
0.7771 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD8455 Phase 2
0.7742 Intermediate Similarity NPD2935 Discontinued
0.774 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD7286 Phase 2
0.7716 Intermediate Similarity NPD3226 Approved
0.7709 Intermediate Similarity NPD4360 Phase 2
0.7709 Intermediate Similarity NPD4363 Phase 3
0.7697 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD1610 Phase 2
0.761 Intermediate Similarity NPD2309 Approved
0.7607 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD5124 Phase 1
0.7586 Intermediate Similarity NPD1548 Phase 1
0.7584 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD7033 Discontinued
0.7547 Intermediate Similarity NPD4628 Phase 3
0.7533 Intermediate Similarity NPD1203 Approved
0.7532 Intermediate Similarity NPD943 Approved
0.753 Intermediate Similarity NPD1465 Phase 2
0.7529 Intermediate Similarity NPD3787 Discontinued
0.7516 Intermediate Similarity NPD6099 Approved
0.7516 Intermediate Similarity NPD5406 Approved
0.7516 Intermediate Similarity NPD6100 Approved
0.7516 Intermediate Similarity NPD5408 Approved
0.7516 Intermediate Similarity NPD5404 Approved
0.7516 Intermediate Similarity NPD5405 Approved
0.7515 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6832 Phase 2
0.75 Intermediate Similarity NPD7458 Discontinued
0.7486 Intermediate Similarity NPD4287 Approved
0.7485 Intermediate Similarity NPD3926 Phase 2
0.7471 Intermediate Similarity NPD1247 Approved
0.7468 Intermediate Similarity NPD2346 Discontinued
0.7457 Intermediate Similarity NPD3751 Discontinued
0.7456 Intermediate Similarity NPD919 Approved
0.7438 Intermediate Similarity NPD7003 Approved
0.7407 Intermediate Similarity NPD7212 Phase 2
0.7407 Intermediate Similarity NPD7213 Phase 3
0.7405 Intermediate Similarity NPD6780 Approved
0.7405 Intermediate Similarity NPD6778 Approved
0.7405 Intermediate Similarity NPD6782 Approved
0.7405 Intermediate Similarity NPD6781 Approved
0.7405 Intermediate Similarity NPD6777 Approved
0.7405 Intermediate Similarity NPD6779 Approved
0.7405 Intermediate Similarity NPD6776 Approved
0.7403 Intermediate Similarity NPD3268 Approved
0.7378 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD4361 Phase 2
0.7377 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD2798 Approved
0.7368 Intermediate Similarity NPD8151 Discontinued
0.7362 Intermediate Similarity NPD7447 Phase 1
0.7354 Intermediate Similarity NPD7584 Approved
0.7351 Intermediate Similarity NPD3225 Approved
0.734 Intermediate Similarity NPD7871 Phase 2
0.734 Intermediate Similarity NPD7870 Phase 2
0.7329 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7229 Phase 3
0.7326 Intermediate Similarity NPD5711 Approved
0.7326 Intermediate Similarity NPD5710 Approved
0.7312 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD1613 Approved
0.7303 Intermediate Similarity NPD2797 Approved
0.729 Intermediate Similarity NPD6798 Discontinued
0.729 Intermediate Similarity NPD3764 Approved
0.7287 Intermediate Similarity NPD7697 Approved
0.7287 Intermediate Similarity NPD7435 Discontinued
0.7287 Intermediate Similarity NPD7698 Approved
0.7287 Intermediate Similarity NPD7696 Phase 3
0.7278 Intermediate Similarity NPD4288 Approved
0.7267 Intermediate Similarity NPD422 Phase 1
0.7262 Intermediate Similarity NPD6844 Discontinued
0.7257 Intermediate Similarity NPD7177 Discontinued
0.7256 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD4308 Phase 3
0.7226 Intermediate Similarity NPD4625 Phase 3
0.7219 Intermediate Similarity NPD9717 Approved
0.7202 Intermediate Similarity NPD5889 Approved
0.7202 Intermediate Similarity NPD5890 Approved
0.7202 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD7783 Phase 2
0.719 Intermediate Similarity NPD1470 Approved
0.7182 Intermediate Similarity NPD8150 Discontinued
0.7175 Intermediate Similarity NPD1729 Discontinued
0.717 Intermediate Similarity NPD7097 Phase 1
0.7168 Intermediate Similarity NPD7199 Phase 2
0.7161 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2654 Approved
0.7159 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1201 Approved
0.7143 Intermediate Similarity NPD6823 Phase 2
0.7143 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6535 Approved
0.7135 Intermediate Similarity NPD6534 Approved
0.7135 Intermediate Similarity NPD7701 Phase 2
0.7108 Intermediate Similarity NPD6273 Approved
0.7099 Intermediate Similarity NPD2424 Discontinued
0.7097 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD2861 Phase 2
0.7091 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD3266 Approved
0.7078 Intermediate Similarity NPD3267 Approved
0.7076 Intermediate Similarity NPD2296 Approved
0.707 Intermediate Similarity NPD1296 Phase 2
0.7062 Intermediate Similarity NPD7874 Approved
0.7062 Intermediate Similarity NPD7228 Approved
0.7062 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD37 Approved
0.7059 Intermediate Similarity NPD7577 Discontinued
0.7052 Intermediate Similarity NPD6234 Discontinued
0.7044 Intermediate Similarity NPD1933 Approved
0.7044 Intermediate Similarity NPD230 Phase 1
0.7044 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD6585 Discontinued
0.7035 Intermediate Similarity NPD4966 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