Structure

Physi-Chem Properties

Molecular Weight:  504.21
Volume:  525.741
LogP:  7.475
LogD:  4.006
LogS:  -1.744
# Rotatable Bonds:  5
TPSA:  120.36
# H-Bond Aceptor:  7
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.178
Synthetic Accessibility Score:  3.622
Fsp3:  0.3
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.935
MDCK Permeability:  1.546729981782846e-05
Pgp-inhibitor:  0.894
Pgp-substrate:  0.031
Human Intestinal Absorption (HIA):  0.319
20% Bioavailability (F20%):  0.877
30% Bioavailability (F30%):  0.161

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  92.83495330810547%
Volume Distribution (VD):  0.743
Pgp-substrate:  9.669966697692871%

ADMET: Metabolism

CYP1A2-inhibitor:  0.345
CYP1A2-substrate:  0.178
CYP2C19-inhibitor:  0.772
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.862
CYP2C9-substrate:  0.86
CYP2D6-inhibitor:  0.59
CYP2D6-substrate:  0.181
CYP3A4-inhibitor:  0.182
CYP3A4-substrate:  0.082

ADMET: Excretion

Clearance (CL):  5.189
Half-life (T1/2):  0.265

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.969
Drug-inuced Liver Injury (DILI):  0.979
AMES Toxicity:  0.27
Rat Oral Acute Toxicity:  0.822
Maximum Recommended Daily Dose:  0.796
Skin Sensitization:  0.823
Carcinogencity:  0.396
Eye Corrosion:  0.003
Eye Irritation:  0.415
Respiratory Toxicity:  0.351

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Structure MOL file  
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  Natural Product: NPC218871

Natural Product ID:  NPC218871
Common Name*:   Heterophyllin
IUPAC Name:   5-hydroxy-2,2-dimethyl-7,10-bis(3-methylbut-2-enyl)-8-(2,4,5-trihydroxyphenyl)pyrano[3,2-g]chromen-6-one
Synonyms:   Heterophyllin
Standard InCHIKey:  CBYLXVCMCVXUQQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C30H32O7/c1-15(2)7-9-17-25(34)24-26(35)18-11-12-30(5,6)37-28(18)19(10-8-16(3)4)29(24)36-27(17)20-13-22(32)23(33)14-21(20)31/h7-8,11-14,31-33,35H,9-10H2,1-6H3
SMILES:  CC(=CCc1c(=O)c2c(c3C=CC(C)(C)Oc3c(CC=C(C)C)c2oc1c1cc(c(cc1O)O)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL461821
PubChem CID:   14557105
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones
          • [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. root n.a. DOI[10.1016/0031-9422(95)00135-T]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. root n.a. PMID[11395279]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants Shawnee National Forest, Harrisburg, IL, US n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants n.a. n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[12419367]
NPO33150 Artocarpus communis Species Moraceae Eukaryota heartwood n.a. n.a. PMID[16643064]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota leaves Kaohsiung, Taiwan 2006-SEP PMID[18986201]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota Fruits n.a. n.a. PMID[19296617]
NPO12348 Chrysosplenium grayanum Species Saxifragaceae Eukaryota n.a. n.a. n.a. PMID[1955888]
NPO6876 Ixora coccinea Species Rubiaceae Eukaryota aerial parts collected on the campus of Kaohsiung Medical University, Taiwan 2007-Oct PMID[21106454]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Wood n.a. n.a. PMID[23113717]
NPO33150 Artocarpus communis Species Moraceae Eukaryota roots Khon Kaen, Thailand 2009-DEC PMID[25537111]
NPO33150 Artocarpus communis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[26178912]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. formosan n.a. PMID[8864236]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. formosan n.a. PMID[8864236]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9358644]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO12348 Chrysosplenium grayanum Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6890 Euphorbia jolkinii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18019 Dalbergia oliveri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12348 Chrysosplenium grayanum Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17471 Penicillium obscurum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6890 Euphorbia jolkinii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12348 Chrysosplenium grayanum Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17091 Berberis chilensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15941 Bacillus licheniformis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6876 Ixora coccinea Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16603 Mundulea sericea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17021 Mahonia aquifolia n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO18019 Dalbergia oliveri Species Fabaceae 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
NPT196 Cell Line AGS Homo sapiens Activity = 31.0 % PMID[527251]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 80.2 % PMID[527250]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 32.0 % PMID[527250]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 0.0 % PMID[527250]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 49800.0 nM PMID[527250]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 48700.0 nM PMID[527250]

☑ 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 NPC218871 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 NPC476630
0.9933 High Similarity NPC276444
0.9799 High Similarity NPC170492
0.9735 High Similarity NPC237418
0.9732 High Similarity NPC249570
0.9673 High Similarity NPC198829
0.9673 High Similarity NPC259456
0.9671 High Similarity NPC469658
0.9669 High Similarity NPC471985
0.9667 High Similarity NPC476631
0.961 High Similarity NPC194427
0.9608 High Similarity NPC204290
0.9597 High Similarity NPC3825
0.9597 High Similarity NPC88804
0.9545 High Similarity NPC167678
0.9545 High Similarity NPC29876
0.9539 High Similarity NPC282307
0.9539 High Similarity NPC170026
0.9533 High Similarity NPC154345
0.9487 High Similarity NPC156432
0.9484 High Similarity NPC472448
0.9484 High Similarity NPC83922
0.9484 High Similarity NPC329760
0.9484 High Similarity NPC261470
0.9481 High Similarity NPC476980
0.9481 High Similarity NPC28241
0.947 High Similarity NPC37684
0.947 High Similarity NPC157784
0.947 High Similarity NPC63187
0.9427 High Similarity NPC39091
0.9423 High Similarity NPC23298
0.9423 High Similarity NPC207690
0.9423 High Similarity NPC189473
0.9419 High Similarity NPC278427
0.9416 High Similarity NPC74178
0.9416 High Similarity NPC184755
0.9412 High Similarity NPC191146
0.9412 High Similarity NPC68093
0.9404 High Similarity NPC304295
0.9404 High Similarity NPC205046
0.9404 High Similarity NPC59162
0.9363 High Similarity NPC239752
0.9363 High Similarity NPC130920
0.9363 High Similarity NPC472450
0.9363 High Similarity NPC85057
0.9363 High Similarity NPC50960
0.9363 High Similarity NPC275780
0.9359 High Similarity NPC78332
0.9355 High Similarity NPC476280
0.9355 High Similarity NPC119209
0.9355 High Similarity NPC118256
0.9355 High Similarity NPC192686
0.9351 High Similarity NPC218313
0.9351 High Similarity NPC273843
0.9351 High Similarity NPC476981
0.9351 High Similarity NPC236796
0.9351 High Similarity NPC474681
0.9351 High Similarity NPC471209
0.9351 High Similarity NPC78225
0.9346 High Similarity NPC472280
0.9346 High Similarity NPC133392
0.9346 High Similarity NPC234255
0.9346 High Similarity NPC113906
0.9342 High Similarity NPC471982
0.9342 High Similarity NPC237994
0.9338 High Similarity NPC184136
0.9308 High Similarity NPC476637
0.9304 High Similarity NPC472449
0.9304 High Similarity NPC37870
0.9299 High Similarity NPC303460
0.9299 High Similarity NPC306321
0.9295 High Similarity NPC474038
0.9295 High Similarity NPC471210
0.9295 High Similarity NPC258331
0.9295 High Similarity NPC40037
0.929 High Similarity NPC172770
0.929 High Similarity NPC185258
0.929 High Similarity NPC197856
0.929 High Similarity NPC46736
0.929 High Similarity NPC204879
0.9286 High Similarity NPC138243
0.9286 High Similarity NPC142339
0.9286 High Similarity NPC475799
0.9286 High Similarity NPC3980
0.9286 High Similarity NPC13779
0.9286 High Similarity NPC133970
0.9286 High Similarity NPC5322
0.9286 High Similarity NPC6633
0.9286 High Similarity NPC472455
0.9281 High Similarity NPC255350
0.9281 High Similarity NPC176775
0.9281 High Similarity NPC160951
0.9281 High Similarity NPC47781
0.9281 High Similarity NPC69394
0.9281 High Similarity NPC213896
0.9281 High Similarity NPC145379
0.9281 High Similarity NPC22519
0.9281 High Similarity NPC231018
0.9281 High Similarity NPC192083
0.9281 High Similarity NPC298692
0.9281 High Similarity NPC74924
0.9281 High Similarity NPC274327
0.9281 High Similarity NPC183878
0.9267 High Similarity NPC130230
0.9267 High Similarity NPC108406
0.9267 High Similarity NPC275772
0.9267 High Similarity NPC239312
0.925 High Similarity NPC101107
0.9245 High Similarity NPC126204
0.9241 High Similarity NPC259757
0.9236 High Similarity NPC474150
0.9236 High Similarity NPC474162
0.9236 High Similarity NPC25152
0.9236 High Similarity NPC229632
0.9236 High Similarity NPC206605
0.9236 High Similarity NPC8300
0.9231 High Similarity NPC45146
0.9231 High Similarity NPC320359
0.9231 High Similarity NPC328102
0.9231 High Similarity NPC475784
0.9231 High Similarity NPC471973
0.9231 High Similarity NPC80375
0.9231 High Similarity NPC139036
0.9231 High Similarity NPC119224
0.9231 High Similarity NPC297212
0.9231 High Similarity NPC246478
0.9231 High Similarity NPC235018
0.9226 High Similarity NPC473272
0.9226 High Similarity NPC284820
0.9226 High Similarity NPC27337
0.9226 High Similarity NPC79053
0.9226 High Similarity NPC262286
0.9226 High Similarity NPC223787
0.9226 High Similarity NPC36852
0.9226 High Similarity NPC52889
0.9221 High Similarity NPC138360
0.9221 High Similarity NPC280339
0.9221 High Similarity NPC213622
0.9221 High Similarity NPC321779
0.9221 High Similarity NPC201136
0.9221 High Similarity NPC256612
0.9221 High Similarity NPC183597
0.9221 High Similarity NPC146165
0.9221 High Similarity NPC128863
0.9221 High Similarity NPC200246
0.9221 High Similarity NPC92659
0.9221 High Similarity NPC50715
0.9221 High Similarity NPC20830
0.9221 High Similarity NPC227325
0.9221 High Similarity NPC167815
0.9221 High Similarity NPC163780
0.9221 High Similarity NPC196439
0.9221 High Similarity NPC4455
0.9221 High Similarity NPC2476
0.9216 High Similarity NPC301323
0.9216 High Similarity NPC25270
0.9216 High Similarity NPC71334
0.9216 High Similarity NPC156222
0.9216 High Similarity NPC275836
0.9216 High Similarity NPC239128
0.9216 High Similarity NPC131624
0.9216 High Similarity NPC57030
0.9216 High Similarity NPC256283
0.9216 High Similarity NPC162313
0.9216 High Similarity NPC293183
0.9216 High Similarity NPC187498
0.9216 High Similarity NPC188203
0.9216 High Similarity NPC275722
0.9216 High Similarity NPC222830
0.9216 High Similarity NPC120163
0.9216 High Similarity NPC45934
0.9216 High Similarity NPC241498
0.9216 High Similarity NPC198826
0.9216 High Similarity NPC106976
0.9216 High Similarity NPC212678
0.9216 High Similarity NPC83508
0.9216 High Similarity NPC100887
0.9211 High Similarity NPC62042
0.9211 High Similarity NPC101957
0.9211 High Similarity NPC120105
0.9205 High Similarity NPC276930
0.9205 High Similarity NPC118726
0.9205 High Similarity NPC12367
0.9195 High Similarity NPC279121
0.9187 High Similarity NPC475805
0.9187 High Similarity NPC471287
0.9177 High Similarity NPC248638
0.9177 High Similarity NPC152659
0.9177 High Similarity NPC236521
0.9177 High Similarity NPC12461
0.9177 High Similarity NPC186686
0.9177 High Similarity NPC234004
0.9177 High Similarity NPC472625
0.9172 High Similarity NPC266314
0.9172 High Similarity NPC61010
0.9172 High Similarity NPC26326
0.9172 High Similarity NPC471211
0.9172 High Similarity NPC32694
0.9172 High Similarity NPC472275
0.9172 High Similarity NPC40491

  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 NPC218871 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
0.9281 High Similarity NPD2393 Clinical (unspecified phase)
0.9281 High Similarity NPD2801 Approved
0.9195 High Similarity NPD1511 Approved
0.9073 High Similarity NPD1512 Approved
0.8968 High Similarity NPD1934 Approved
0.8882 High Similarity NPD4378 Clinical (unspecified phase)
0.8758 High Similarity NPD7410 Clinical (unspecified phase)
0.865 High Similarity NPD6168 Clinical (unspecified phase)
0.865 High Similarity NPD6167 Clinical (unspecified phase)
0.865 High Similarity NPD6166 Phase 2
0.8606 High Similarity NPD7054 Approved
0.8599 High Similarity NPD4380 Phase 2
0.8562 High Similarity NPD3882 Suspended
0.8554 High Similarity NPD7472 Approved
0.8554 High Similarity NPD7074 Phase 3
0.8519 High Similarity NPD5494 Approved
0.85 High Similarity NPD3817 Phase 2
0.8452 Intermediate Similarity NPD7251 Discontinued
0.8434 Intermediate Similarity NPD3818 Discontinued
0.8402 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD7075 Discontinued
0.8393 Intermediate Similarity NPD6797 Phase 2
0.8385 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD7819 Suspended
0.8323 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8301 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8301 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8294 Intermediate Similarity NPD7808 Phase 3
0.8289 Intermediate Similarity NPD1510 Phase 2
0.8282 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8274 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD7473 Discontinued
0.8247 Intermediate Similarity NPD1549 Phase 2
0.8235 Intermediate Similarity NPD2796 Approved
0.8199 Intermediate Similarity NPD7411 Suspended
0.8193 Intermediate Similarity NPD6232 Discontinued
0.8166 Intermediate Similarity NPD5844 Phase 1
0.816 Intermediate Similarity NPD5402 Approved
0.8148 Intermediate Similarity NPD6801 Discontinued
0.8146 Intermediate Similarity NPD1240 Approved
0.8146 Intermediate Similarity NPD943 Approved
0.8133 Intermediate Similarity NPD6959 Discontinued
0.8117 Intermediate Similarity NPD2935 Discontinued
0.8039 Intermediate Similarity NPD1607 Approved
0.8025 Intermediate Similarity NPD3750 Approved
0.8024 Intermediate Similarity NPD1247 Approved
0.8 Intermediate Similarity NPD7768 Phase 2
0.7988 Intermediate Similarity NPD1465 Phase 2
0.7987 Intermediate Similarity NPD6799 Approved
0.7962 Intermediate Similarity NPD2800 Approved
0.7898 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD3749 Approved
0.784 Intermediate Similarity NPD5403 Approved
0.7816 Intermediate Similarity NPD6559 Discontinued
0.7815 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD6599 Discontinued
0.7798 Intermediate Similarity NPD919 Approved
0.7771 Intermediate Similarity NPD6100 Approved
0.7771 Intermediate Similarity NPD6099 Approved
0.7736 Intermediate Similarity NPD1243 Approved
0.7736 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD2534 Approved
0.7716 Intermediate Similarity NPD2533 Approved
0.7716 Intermediate Similarity NPD2532 Approved
0.7716 Intermediate Similarity NPD5401 Approved
0.7709 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD3748 Approved
0.7692 Intermediate Similarity NPD6651 Approved
0.7677 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD1613 Approved
0.7662 Intermediate Similarity NPD2313 Discontinued
0.7662 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD7390 Discontinued
0.7636 Intermediate Similarity NPD3226 Approved
0.7628 Intermediate Similarity NPD230 Phase 1
0.7624 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD920 Approved
0.7616 Intermediate Similarity NPD3926 Phase 2
0.7595 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD2799 Discontinued
0.7578 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD1551 Phase 2
0.7543 Intermediate Similarity NPD7286 Phase 2
0.7516 Intermediate Similarity NPD447 Suspended
0.7515 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2344 Approved
0.75 Intermediate Similarity NPD2346 Discontinued
0.75 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3027 Phase 3
0.7458 Intermediate Similarity NPD5953 Discontinued
0.7444 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7433 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD3751 Discontinued
0.7372 Intermediate Similarity NPD4625 Phase 3
0.7366 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1653 Approved
0.7362 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD4628 Phase 3
0.7356 Intermediate Similarity NPD3787 Discontinued
0.7351 Intermediate Similarity NPD4363 Phase 3
0.7351 Intermediate Similarity NPD4360 Phase 2
0.7338 Intermediate Similarity NPD1203 Approved
0.7333 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD3268 Approved
0.7317 Intermediate Similarity NPD2309 Approved
0.7317 Intermediate Similarity NPD6190 Approved
0.7308 Intermediate Similarity NPD4908 Phase 1
0.7299 Intermediate Similarity NPD7199 Phase 2
0.7296 Intermediate Similarity NPD5124 Phase 1
0.7296 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD6844 Discontinued
0.7292 Intermediate Similarity NPD7584 Approved
0.729 Intermediate Similarity NPD2798 Approved
0.7289 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD6234 Discontinued
0.7273 Intermediate Similarity NPD3225 Approved
0.7267 Intermediate Similarity NPD4308 Phase 3
0.7267 Intermediate Similarity NPD7033 Discontinued
0.7249 Intermediate Similarity NPD6776 Approved
0.7249 Intermediate Similarity NPD6782 Approved
0.7249 Intermediate Similarity NPD6780 Approved
0.7249 Intermediate Similarity NPD6778 Approved
0.7249 Intermediate Similarity NPD6779 Approved
0.7249 Intermediate Similarity NPD6777 Approved
0.7249 Intermediate Similarity NPD6781 Approved
0.7238 Intermediate Similarity NPD8313 Approved
0.7238 Intermediate Similarity NPD8312 Approved
0.7226 Intermediate Similarity NPD2797 Approved
0.7225 Intermediate Similarity NPD7435 Discontinued
0.7222 Intermediate Similarity NPD7685 Pre-registration
0.7216 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD8434 Phase 2
0.7213 Intermediate Similarity NPD8150 Discontinued
0.7208 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD6832 Phase 2
0.7191 Intermediate Similarity NPD7228 Approved
0.719 Intermediate Similarity NPD422 Phase 1
0.7188 Intermediate Similarity NPD1933 Approved
0.7159 Intermediate Similarity NPD7229 Phase 3
0.7159 Intermediate Similarity NPD5710 Approved
0.7159 Intermediate Similarity NPD5711 Approved
0.7152 Intermediate Similarity NPD1548 Phase 1
0.7143 Intermediate Similarity NPD7783 Phase 2
0.7143 Intermediate Similarity NPD1608 Approved
0.7143 Intermediate Similarity NPD9717 Approved
0.7143 Intermediate Similarity NPD9269 Phase 2
0.7143 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7696 Phase 3
0.7135 Intermediate Similarity NPD7698 Approved
0.7135 Intermediate Similarity NPD7697 Approved
0.7135 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD9494 Approved
0.7128 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4361 Phase 2
0.7118 Intermediate Similarity NPD7458 Discontinued
0.7117 Intermediate Similarity NPD5404 Approved
0.7117 Intermediate Similarity NPD5406 Approved
0.7117 Intermediate Similarity NPD5405 Approved
0.7117 Intermediate Similarity NPD5408 Approved
0.711 Intermediate Similarity NPD4288 Approved
0.7098 Intermediate Similarity NPD7871 Phase 2
0.7098 Intermediate Similarity NPD7870 Phase 2
0.7097 Intermediate Similarity NPD4749 Approved
0.7093 Intermediate Similarity NPD37 Approved
0.7083 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD6823 Phase 2
0.7081 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD1610 Phase 2
0.7078 Intermediate Similarity NPD1201 Approved
0.7077 Intermediate Similarity NPD7701 Phase 2
0.7069 Intermediate Similarity NPD4965 Approved
0.7069 Intermediate Similarity NPD4966 Approved
0.7069 Intermediate Similarity NPD4967 Phase 2
0.7067 Intermediate Similarity NPD6671 Approved
0.7066 Intermediate Similarity NPD3300 Phase 2
0.7041 Intermediate Similarity NPD8151 Discontinued
0.7025 Intermediate Similarity NPD2861 Phase 2
0.7019 Intermediate Similarity NPD4307 Phase 2
0.7018 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD3266 Approved
0.7006 Intermediate Similarity NPD1470 Approved
0.7006 Intermediate Similarity NPD3267 Approved
0.7005 Intermediate Similarity NPD7874 Approved
0.7005 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD411 Approved
0.6995 Remote Similarity NPD7549 Discontinued
0.6988 Remote Similarity NPD2654 Approved
0.6984 Remote Similarity NPD6535 Approved
0.6984 Remote Similarity NPD6534 Approved
0.6983 Remote Similarity NPD2403 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