Structure

Physi-Chem Properties

Molecular Weight:  586.22
Volume:  598.676
LogP:  7.342
LogD:  3.756
LogS:  -2.202
# Rotatable Bonds:  7
TPSA:  121.5
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.189
Synthetic Accessibility Score:  4.265
Fsp3:  0.324
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.804
MDCK Permeability:  1.807263288355898e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.757
Human Intestinal Absorption (HIA):  0.716
20% Bioavailability (F20%):  0.02
30% Bioavailability (F30%):  0.083

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.011
Plasma Protein Binding (PPB):  83.30912017822266%
Volume Distribution (VD):  1.277
Pgp-substrate:  12.952886581420898%

ADMET: Metabolism

CYP1A2-inhibitor:  0.076
CYP1A2-substrate:  0.151
CYP2C19-inhibitor:  0.687
CYP2C19-substrate:  0.133
CYP2C9-inhibitor:  0.893
CYP2C9-substrate:  0.787
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.142
CYP3A4-inhibitor:  0.221
CYP3A4-substrate:  0.255

ADMET: Excretion

Clearance (CL):  1.023
Half-life (T1/2):  0.064

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.974
Drug-inuced Liver Injury (DILI):  0.969
AMES Toxicity:  0.322
Rat Oral Acute Toxicity:  0.989
Maximum Recommended Daily Dose:  0.17
Skin Sensitization:  0.47
Carcinogencity:  0.067
Eye Corrosion:  0.003
Eye Irritation:  0.044
Respiratory Toxicity:  0.809

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

  Natural Product: NPC475669

Natural Product ID:  NPC475669
Common Name*:   Cycloheterphyllin Diacetate
IUPAC Name:   n.a.
Synonyms:   Cycloheterphyllin Diacetate
Standard InCHIKey:  BLGOUETXOBGGAX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C34H34O9/c1-16(2)9-10-21-31-20(11-12-34(7,8)43-31)29(37)28-30(38)27-26(13-17(3)4)41-23-15-25(40-19(6)36)24(39-18(5)35)14-22(23)33(27)42-32(21)28/h9,11-15,26,37H,10H2,1-8H3
SMILES:  CC(=CC1Oc2cc(OC(=O)C)c(cc2c2c1c(=O)c1c(o2)c(CC=C(C)C)c2c(c1O)C=CC(O2)(C)C)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL510985
PubChem CID:   44566809
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0003520] Pyranoflavonoids

*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 n.a. n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants Shawnee National Forest, Harrisburg, IL, US n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[12419367]
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]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Wood n.a. n.a. PMID[23113717]
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]
NPO17767 Artocarpus heterophyllus Species Moraceae 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[TCMID]
NPO5495 Broussonetia papyrifera Species Moraceae 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]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17767 Artocarpus heterophyllus Species Moraceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 4.9 % PMID[523213]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 91.3 % PMID[523213]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 83.4 % PMID[523213]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 86.0 % PMID[523213]

☑ 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 NPC475669 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
0.9688 High Similarity NPC475369
0.9379 High Similarity NPC40037
0.9321 High Similarity NPC194427
0.9207 High Similarity NPC85057
0.9207 High Similarity NPC130920
0.9198 High Similarity NPC477164
0.9193 High Similarity NPC284820
0.9193 High Similarity NPC473272
0.9152 High Similarity NPC120593
0.9146 High Similarity NPC234004
0.9141 High Similarity NPC198829
0.9136 High Similarity NPC469658
0.9091 High Similarity NPC50960
0.9085 High Similarity NPC261470
0.9085 High Similarity NPC8300
0.908 High Similarity NPC118256
0.908 High Similarity NPC119209
0.908 High Similarity NPC475784
0.908 High Similarity NPC192686
0.9074 High Similarity NPC218871
0.9074 High Similarity NPC476981
0.9074 High Similarity NPC108456
0.9074 High Similarity NPC476630
0.9068 High Similarity NPC226025
0.9042 High Similarity NPC177480
0.9036 High Similarity NPC272502
0.903 High Similarity NPC474350
0.9024 High Similarity NPC26326
0.9024 High Similarity NPC471210
0.9024 High Similarity NPC471211
0.9024 High Similarity NPC471212
0.9024 High Similarity NPC259456
0.9024 High Similarity NPC472634
0.9024 High Similarity NPC474038
0.9018 High Similarity NPC184755
0.9018 High Similarity NPC187792
0.9018 High Similarity NPC74178
0.9012 High Similarity NPC276444
0.9012 High Similarity NPC180340
0.9012 High Similarity NPC471985
0.9006 High Similarity NPC475895
0.8988 High Similarity NPC476365
0.8982 High Similarity NPC158761
0.897 High Similarity NPC472448
0.897 High Similarity NPC229632
0.897 High Similarity NPC83922
0.8963 High Similarity NPC472631
0.8963 High Similarity NPC476980
0.8963 High Similarity NPC204290
0.8963 High Similarity NPC472630
0.8963 High Similarity NPC299436
0.8957 High Similarity NPC27337
0.8957 High Similarity NPC78071
0.8957 High Similarity NPC223787
0.8951 High Similarity NPC37392
0.8941 High Similarity NPC99591
0.8935 High Similarity NPC289396
0.8935 High Similarity NPC212038
0.8935 High Similarity NPC271848
0.8935 High Similarity NPC81332
0.8935 High Similarity NPC262580
0.8929 High Similarity NPC477165
0.8929 High Similarity NPC475212
0.8929 High Similarity NPC471287
0.8922 High Similarity NPC13481
0.8922 High Similarity NPC207575
0.8922 High Similarity NPC471213
0.8922 High Similarity NPC39091
0.8916 High Similarity NPC472625
0.8916 High Similarity NPC186686
0.8909 High Similarity NPC475883
0.8909 High Similarity NPC167678
0.8909 High Similarity NPC472632
0.8909 High Similarity NPC266314
0.8909 High Similarity NPC29876
0.8909 High Similarity NPC474187
0.8909 High Similarity NPC474186
0.8909 High Similarity NPC349525
0.8909 High Similarity NPC474351
0.8902 High Similarity NPC53545
0.8902 High Similarity NPC83763
0.8902 High Similarity NPC250214
0.8902 High Similarity NPC168616
0.8902 High Similarity NPC95936
0.8902 High Similarity NPC473990
0.8902 High Similarity NPC117418
0.8896 High Similarity NPC291878
0.8896 High Similarity NPC195796
0.8896 High Similarity NPC35038
0.8896 High Similarity NPC282307
0.8896 High Similarity NPC170026
0.8896 High Similarity NPC278778
0.8896 High Similarity NPC470328
0.8896 High Similarity NPC209614
0.8896 High Similarity NPC472626
0.8889 High Similarity NPC472408
0.8889 High Similarity NPC128961
0.8889 High Similarity NPC186507
0.8889 High Similarity NPC170492
0.8889 High Similarity NPC280937
0.8889 High Similarity NPC476631
0.8882 High Similarity NPC208043
0.8882 High Similarity NPC226973
0.8882 High Similarity NPC308451
0.8882 High Similarity NPC208668
0.8876 High Similarity NPC103307
0.8875 High Similarity NPC328119
0.8869 High Similarity NPC218226
0.8869 High Similarity NPC471288
0.8869 High Similarity NPC243877
0.8869 High Similarity NPC470456
0.8869 High Similarity NPC8965
0.8862 High Similarity NPC239752
0.8862 High Similarity NPC470457
0.8862 High Similarity NPC472450
0.8862 High Similarity NPC142614
0.8862 High Similarity NPC275780
0.8862 High Similarity NPC293319
0.8855 High Similarity NPC474033
0.8855 High Similarity NPC474150
0.8855 High Similarity NPC81679
0.8855 High Similarity NPC201800
0.8855 High Similarity NPC471745
0.8855 High Similarity NPC472635
0.8855 High Similarity NPC474162
0.8855 High Similarity NPC474034
0.8848 High Similarity NPC475886
0.8848 High Similarity NPC28241
0.8848 High Similarity NPC292415
0.8848 High Similarity NPC328102
0.8848 High Similarity NPC474287
0.8848 High Similarity NPC472624
0.8848 High Similarity NPC174953
0.8841 High Similarity NPC474208
0.8841 High Similarity NPC183851
0.8841 High Similarity NPC48208
0.8841 High Similarity NPC474836
0.8841 High Similarity NPC183
0.8841 High Similarity NPC474055
0.8841 High Similarity NPC162869
0.8841 High Similarity NPC19097
0.8841 High Similarity NPC475267
0.8841 High Similarity NPC291508
0.8841 High Similarity NPC237418
0.8841 High Similarity NPC470402
0.8841 High Similarity NPC63454
0.8841 High Similarity NPC156057
0.8841 High Similarity NPC52889
0.8841 High Similarity NPC78225
0.8841 High Similarity NPC472598
0.8841 High Similarity NPC471209
0.8834 High Similarity NPC183597
0.8834 High Similarity NPC477503
0.8834 High Similarity NPC128863
0.8834 High Similarity NPC470681
0.8834 High Similarity NPC50715
0.8834 High Similarity NPC201136
0.8834 High Similarity NPC470327
0.8834 High Similarity NPC92659
0.8834 High Similarity NPC279218
0.8834 High Similarity NPC45849
0.8834 High Similarity NPC200761
0.8834 High Similarity NPC227325
0.8834 High Similarity NPC163780
0.8834 High Similarity NPC196439
0.8834 High Similarity NPC213622
0.8834 High Similarity NPC472909
0.8834 High Similarity NPC2476
0.8834 High Similarity NPC146165
0.8834 High Similarity NPC138360
0.8834 High Similarity NPC280339
0.8834 High Similarity NPC167815
0.8834 High Similarity NPC108937
0.8834 High Similarity NPC234255
0.8834 High Similarity NPC4455
0.8827 High Similarity NPC40033
0.8827 High Similarity NPC199773
0.8827 High Similarity NPC471982
0.8827 High Similarity NPC249570
0.8827 High Similarity NPC289968
0.8824 High Similarity NPC172807
0.8824 High Similarity NPC254540
0.8824 High Similarity NPC256760
0.8824 High Similarity NPC475825
0.8824 High Similarity NPC211594
0.8824 High Similarity NPC472386
0.8824 High Similarity NPC223375
0.882 High Similarity NPC338131
0.882 High Similarity NPC472633
0.882 High Similarity NPC189270
0.882 High Similarity NPC5840
0.882 High Similarity NPC306821
0.882 High Similarity NPC37348
0.8817 High Similarity NPC326877
0.8817 High Similarity NPC280493
0.8817 High Similarity NPC99613
0.8817 High Similarity NPC165456
0.8817 High Similarity NPC49487
0.8817 High Similarity NPC476637
0.8812 High Similarity NPC321623

  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 NPC475669 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
0.8773 High Similarity NPD2801 Approved
0.8773 High Similarity NPD2393 Clinical (unspecified phase)
0.872 High Similarity NPD3817 Phase 2
0.8712 High Similarity NPD1934 Approved
0.8706 High Similarity NPD7054 Approved
0.8655 High Similarity NPD7472 Approved
0.8655 High Similarity NPD7074 Phase 3
0.8639 High Similarity NPD6166 Phase 2
0.8639 High Similarity NPD6168 Clinical (unspecified phase)
0.8639 High Similarity NPD6167 Clinical (unspecified phase)
0.8614 High Similarity NPD7075 Discontinued
0.8613 High Similarity NPD7808 Phase 3
0.8613 High Similarity NPD4338 Clinical (unspecified phase)
0.8596 High Similarity NPD5844 Phase 1
0.8545 High Similarity NPD7819 Suspended
0.8512 High Similarity NPD5494 Approved
0.8488 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.848 Intermediate Similarity NPD7473 Discontinued
0.8476 Intermediate Similarity NPD4380 Phase 2
0.8448 Intermediate Similarity NPD7251 Discontinued
0.8443 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.843 Intermediate Similarity NPD3818 Discontinued
0.8412 Intermediate Similarity NPD6232 Discontinued
0.8395 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8391 Intermediate Similarity NPD6797 Phase 2
0.8383 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8383 Intermediate Similarity NPD5402 Approved
0.8373 Intermediate Similarity NPD6801 Discontinued
0.8333 Intermediate Similarity NPD1511 Approved
0.8313 Intermediate Similarity NPD7411 Suspended
0.8284 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8282 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD1512 Approved
0.8225 Intermediate Similarity NPD3882 Suspended
0.8222 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8208 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.814 Intermediate Similarity NPD6959 Discontinued
0.8129 Intermediate Similarity NPD919 Approved
0.8118 Intermediate Similarity NPD7768 Phase 2
0.8075 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8072 Intermediate Similarity NPD5403 Approved
0.8033 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD1549 Phase 2
0.8012 Intermediate Similarity NPD2935 Discontinued
0.8012 Intermediate Similarity NPD2796 Approved
0.8 Intermediate Similarity NPD6799 Approved
0.8 Intermediate Similarity NPD1465 Phase 2
0.7952 Intermediate Similarity NPD5401 Approved
0.795 Intermediate Similarity NPD1510 Phase 2
0.7933 Intermediate Similarity NPD6559 Discontinued
0.7931 Intermediate Similarity NPD1247 Approved
0.7824 Intermediate Similarity NPD6599 Discontinued
0.7818 Intermediate Similarity NPD3750 Approved
0.7805 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD3749 Approved
0.7758 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD920 Approved
0.7751 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD2533 Approved
0.7738 Intermediate Similarity NPD2532 Approved
0.7738 Intermediate Similarity NPD2534 Approved
0.7706 Intermediate Similarity NPD1653 Approved
0.7702 Intermediate Similarity NPD1240 Approved
0.7688 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD3226 Approved
0.7654 Intermediate Similarity NPD447 Suspended
0.7651 Intermediate Similarity NPD1243 Approved
0.765 Intermediate Similarity NPD8313 Approved
0.765 Intermediate Similarity NPD8312 Approved
0.7633 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD8150 Discontinued
0.7619 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD7783 Phase 2
0.7614 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD1607 Approved
0.7582 Intermediate Similarity NPD5953 Discontinued
0.7576 Intermediate Similarity NPD1551 Phase 2
0.7569 Intermediate Similarity NPD7286 Phase 2
0.7546 Intermediate Similarity NPD5124 Phase 1
0.7546 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD3926 Phase 2
0.7541 Intermediate Similarity NPD7685 Pre-registration
0.7529 Intermediate Similarity NPD37 Approved
0.7528 Intermediate Similarity NPD7199 Phase 2
0.7527 Intermediate Similarity NPD8434 Phase 2
0.7526 Intermediate Similarity NPD7435 Discontinued
0.7515 Intermediate Similarity NPD3748 Approved
0.7514 Intermediate Similarity NPD7228 Approved
0.7514 Intermediate Similarity NPD6234 Discontinued
0.75 Intermediate Similarity NPD4967 Phase 2
0.75 Intermediate Similarity NPD4628 Phase 3
0.75 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD4965 Approved
0.7471 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD2313 Discontinued
0.7461 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD6190 Approved
0.7453 Intermediate Similarity NPD6832 Phase 2
0.7444 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD2800 Approved
0.7439 Intermediate Similarity NPD230 Phase 1
0.7436 Intermediate Similarity NPD7698 Approved
0.7436 Intermediate Similarity NPD7696 Phase 3
0.7436 Intermediate Similarity NPD7697 Approved
0.743 Intermediate Similarity NPD8127 Discontinued
0.7424 Intermediate Similarity NPD8151 Discontinued
0.7418 Intermediate Similarity NPD3751 Discontinued
0.741 Intermediate Similarity NPD7033 Discontinued
0.741 Intermediate Similarity NPD2799 Discontinued
0.7405 Intermediate Similarity NPD7549 Discontinued
0.7403 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD7870 Phase 2
0.7398 Intermediate Similarity NPD7871 Phase 2
0.7396 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD6651 Approved
0.7389 Intermediate Similarity NPD3787 Discontinued
0.7387 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7387 Intermediate Similarity NPD7874 Approved
0.7386 Intermediate Similarity NPD8455 Phase 2
0.7378 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD943 Approved
0.7378 Intermediate Similarity NPD1613 Approved
0.7371 Intermediate Similarity NPD6782 Approved
0.7371 Intermediate Similarity NPD6776 Approved
0.7371 Intermediate Similarity NPD6778 Approved
0.7371 Intermediate Similarity NPD6779 Approved
0.7371 Intermediate Similarity NPD6781 Approved
0.7371 Intermediate Similarity NPD6777 Approved
0.7371 Intermediate Similarity NPD6780 Approved
0.7368 Intermediate Similarity NPD7390 Discontinued
0.7356 Intermediate Similarity NPD7458 Discontinued
0.7333 Intermediate Similarity NPD1933 Approved
0.7323 Intermediate Similarity NPD7584 Approved
0.7321 Intermediate Similarity NPD2346 Discontinued
0.7312 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD3027 Phase 3
0.7286 Intermediate Similarity NPD7701 Phase 2
0.7273 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1203 Approved
0.7262 Intermediate Similarity NPD6100 Approved
0.7262 Intermediate Similarity NPD6099 Approved
0.7256 Intermediate Similarity NPD3268 Approved
0.7239 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD8285 Discontinued
0.7229 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD6823 Phase 2
0.7205 Intermediate Similarity NPD3225 Approved
0.7202 Intermediate Similarity NPD4363 Phase 3
0.7202 Intermediate Similarity NPD4308 Phase 3
0.7202 Intermediate Similarity NPD4360 Phase 2
0.72 Intermediate Similarity NPD7585 Approved
0.7198 Intermediate Similarity NPD5710 Approved
0.7198 Intermediate Similarity NPD5711 Approved
0.7198 Intermediate Similarity NPD7229 Phase 3
0.7179 Intermediate Similarity NPD7699 Phase 2
0.7179 Intermediate Similarity NPD7700 Phase 2
0.7178 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD7801 Approved
0.7166 Intermediate Similarity NPD7240 Approved
0.716 Intermediate Similarity NPD2797 Approved
0.7159 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD5242 Approved
0.7152 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD5353 Approved
0.715 Intermediate Similarity NPD7583 Approved
0.7135 Intermediate Similarity NPD6844 Discontinued
0.7125 Intermediate Similarity NPD422 Phase 1
0.7113 Intermediate Similarity NPD6534 Approved
0.7113 Intermediate Similarity NPD6535 Approved
0.7108 Intermediate Similarity NPD6233 Phase 2
0.7101 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD9717 Approved
0.7079 Intermediate Similarity NPD6386 Approved
0.7079 Intermediate Similarity NPD6385 Approved
0.705 Intermediate Similarity NPD8319 Approved
0.705 Intermediate Similarity NPD8320 Phase 1
0.7048 Intermediate Similarity NPD6798 Discontinued
0.7041 Intermediate Similarity NPD7097 Phase 1
0.7035 Intermediate Similarity NPD1652 Phase 2
0.7033 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4908 Phase 1
0.7024 Intermediate Similarity NPD6355 Discontinued
0.7018 Intermediate Similarity NPD2344 Approved
0.7018 Intermediate Similarity NPD7266 Discontinued
0.6994 Remote Similarity NPD8166 Discontinued
0.6989 Remote Similarity NPD6273 Approved
0.6984 Remote Similarity NPD7039 Approved
0.6984 Remote Similarity NPD7038 Approved
0.6975 Remote Similarity NPD1608 Approved
0.6964 Remote Similarity NPD4307 Phase 2
0.6964 Remote Similarity NPD4060 Phase 1
0.6961 Remote Similarity NPD4288 Approved
0.6959 Remote Similarity NPD5405 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