Structure

Physi-Chem Properties

Molecular Weight:  1120.55
Volume:  1092.349
LogP:  3.069
LogD:  2.469
LogS:  -3.641
# Rotatable Bonds:  17
TPSA:  306.74
# H-Bond Aceptor:  22
# H-Bond Donor:  8
# Rings:  9
# Heavy Atoms:  22

MedChem Properties

QED Drug-Likeness Score:  0.067
Synthetic Accessibility Score:  6.939
Fsp3:  0.789
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:  -6.155
MDCK Permeability:  0.00013890185800846666
Pgp-inhibitor:  0.002
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.433
20% Bioavailability (F20%):  0.149
30% Bioavailability (F30%):  0.134

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.06
Plasma Protein Binding (PPB):  81.91365814208984%
Volume Distribution (VD):  0.095
Pgp-substrate:  9.596162796020508%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.983
CYP2C19-inhibitor:  0.005
CYP2C19-substrate:  0.31
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.002
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.054
CYP3A4-inhibitor:  0.211
CYP3A4-substrate:  0.923

ADMET: Excretion

Clearance (CL):  1.092
Half-life (T1/2):  0.441

ADMET: Toxicity

hERG Blockers:  0.734
Human Hepatotoxicity (H-HT):  0.245
Drug-inuced Liver Injury (DILI):  0.109
AMES Toxicity:  0.498
Rat Oral Acute Toxicity:  0.479
Maximum Recommended Daily Dose:  0.978
Skin Sensitization:  0.87
Carcinogencity:  0.383
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.922

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

  Natural Product: NPC475613

Natural Product ID:  NPC475613
Common Name*:   [(3S,8S,9R,10R,12R,13S,14R,17R)-17-Acetyl-8,14,17-Trihydroxy-3-[(2R,4R,5R,6R)-4-Methoxy-5-[(2S,4S,5R,6R)-4-Methoxy-5-[(2S,4S,5R,6R)-4-Methoxy-6-Methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-6-Methyloxan-2-Yl]Oxy-6-Methyloxan-2-Yl]Oxy-10,13-Dimethyl-1,2,3,4,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-12-Yl] (E)-3-(4-Hydroxyphenyl)Prop-2-Enoate
IUPAC Name:   [(3S,8S,9R,10R,12R,13S,14R,17R)-17-acetyl-8,14,17-trihydroxy-3-[(2R,4R,5R,6R)-4-methoxy-5-[(2S,4S,5R,6R)-4-methoxy-5-[(2S,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  GHXBXPWGPDQWPN-QEDPWYQISA-N
Standard InCHI:  InChI=1S/C57H84O22/c1-28-49(77-44-24-37(69-8)50(29(2)72-44)78-45-25-38(70-9)51(30(3)73-45)79-52-48(64)47(63)46(62)39(27-58)75-52)36(68-7)23-43(71-28)74-35-17-18-53(5)33(22-35)16-19-56(66)40(53)26-41(54(6)55(65,31(4)59)20-21-57(54,56)67)76-42(61)15-12-32-10-13-34(60)14-11-32/h10-16,28-30,35-41,43-52,58,60,62-67H,17-27H2,1-9H3/b15-12+/t28-,29-,30-,35+,36-,37+,38+,39-,40-,41-,43+,44+,45+,46-,47+,48-,49-,50-,51-,52+,53+,54-,55+,56+,57-/m1/s1
SMILES:  CC1C(C(CC(O1)OC2CCC3(C4CC(C5(C(CCC5(C4(CC=C3C2)O)O)(C(=O)C)O)C)OC(=O)C=CC6=CC=C(C=C6)O)C)OC)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL509315
PubChem CID:   44575235
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides

*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
NPO32487 leptadenia pyrotechnica Species Apocynaceae Eukaryota whole plant Dogon region, Mali 2002-Apr PMID[16643040]

☑ 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
NPT71 Cell Line HEK293 Homo sapiens IC50 = 100.0 nM PMID[558977]
NPT3470 Cell Line WEHI-164 Mus musculus IC50 = 80.0 nM PMID[558977]
NPT1182 Cell Line J774.A1 Mus musculus IC50 = 120.0 nM PMID[558977]

☑ 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 NPC475613 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
0.9202 High Similarity NPC475536
0.9202 High Similarity NPC165234
0.9146 High Similarity NPC475464
0.9146 High Similarity NPC475437
0.9146 High Similarity NPC473797
0.9146 High Similarity NPC475505
0.9146 High Similarity NPC473641
0.9146 High Similarity NPC475300
0.8982 High Similarity NPC161151
0.8765 High Similarity NPC477488
0.8722 High Similarity NPC475299
0.8708 High Similarity NPC189704
0.8698 High Similarity NPC475567
0.8698 High Similarity NPC473557
0.8698 High Similarity NPC473468
0.869 High Similarity NPC269668
0.8671 High Similarity NPC477617
0.8659 High Similarity NPC475121
0.8659 High Similarity NPC476067
0.8652 High Similarity NPC96194
0.8652 High Similarity NPC299855
0.8647 High Similarity NPC475198
0.8647 High Similarity NPC475175
0.8647 High Similarity NPC475531
0.8621 High Similarity NPC195972
0.8588 High Similarity NPC477491
0.8564 High Similarity NPC112708
0.8563 High Similarity NPC476784
0.8528 High Similarity NPC470330
0.8528 High Similarity NPC474564
0.8516 High Similarity NPC473711
0.8514 High Similarity NPC124828
0.8508 High Similarity NPC230670
0.8508 High Similarity NPC71385
0.8485 Intermediate Similarity NPC240592
0.8485 Intermediate Similarity NPC117346
0.8476 Intermediate Similarity NPC476092
0.8476 Intermediate Similarity NPC475447
0.8476 Intermediate Similarity NPC70236
0.8476 Intermediate Similarity NPC475218
0.8439 Intermediate Similarity NPC88176
0.8439 Intermediate Similarity NPC149002
0.8439 Intermediate Similarity NPC469419
0.8439 Intermediate Similarity NPC469396
0.8439 Intermediate Similarity NPC469459
0.8439 Intermediate Similarity NPC469458
0.8436 Intermediate Similarity NPC473776
0.8436 Intermediate Similarity NPC473205
0.843 Intermediate Similarity NPC471861
0.8402 Intermediate Similarity NPC10945
0.8382 Intermediate Similarity NPC102465
0.838 Intermediate Similarity NPC102367
0.8354 Intermediate Similarity NPC320734
0.8352 Intermediate Similarity NPC469776
0.8352 Intermediate Similarity NPC135334
0.8352 Intermediate Similarity NPC469773
0.8352 Intermediate Similarity NPC100925
0.8352 Intermediate Similarity NPC469777
0.8352 Intermediate Similarity NPC469775
0.8352 Intermediate Similarity NPC469774
0.8352 Intermediate Similarity NPC295941
0.8352 Intermediate Similarity NPC13989
0.8352 Intermediate Similarity NPC469772
0.8352 Intermediate Similarity NPC32723
0.8352 Intermediate Similarity NPC469778
0.8323 Intermediate Similarity NPC77310
0.8314 Intermediate Similarity NPC117943
0.8314 Intermediate Similarity NPC477627
0.8314 Intermediate Similarity NPC293568
0.8313 Intermediate Similarity NPC96599
0.8305 Intermediate Similarity NPC471871
0.8282 Intermediate Similarity NPC204644
0.8249 Intermediate Similarity NPC148185
0.8239 Intermediate Similarity NPC471870
0.8235 Intermediate Similarity NPC477467
0.8235 Intermediate Similarity NPC475484
0.8229 Intermediate Similarity NPC477469
0.8229 Intermediate Similarity NPC477466
0.8229 Intermediate Similarity NPC477471
0.8229 Intermediate Similarity NPC477473
0.8222 Intermediate Similarity NPC195114
0.8222 Intermediate Similarity NPC187441
0.8222 Intermediate Similarity NPC283980
0.8222 Intermediate Similarity NPC93685
0.8222 Intermediate Similarity NPC108191
0.8218 Intermediate Similarity NPC109990
0.8204 Intermediate Similarity NPC473719
0.8182 Intermediate Similarity NPC286809
0.8182 Intermediate Similarity NPC471860
0.8176 Intermediate Similarity NPC477474
0.8176 Intermediate Similarity NPC477470
0.8176 Intermediate Similarity NPC477472
0.8171 Intermediate Similarity NPC265600
0.8171 Intermediate Similarity NPC329647
0.8171 Intermediate Similarity NPC470735
0.8167 Intermediate Similarity NPC115447
0.8167 Intermediate Similarity NPC470581
0.8167 Intermediate Similarity NPC80360
0.8167 Intermediate Similarity NPC83331
0.8167 Intermediate Similarity NPC260300
0.8167 Intermediate Similarity NPC470582
0.8167 Intermediate Similarity NPC469418
0.8166 Intermediate Similarity NPC469456
0.8166 Intermediate Similarity NPC478235
0.8161 Intermediate Similarity NPC145847
0.8161 Intermediate Similarity NPC471850
0.8155 Intermediate Similarity NPC267469
0.8155 Intermediate Similarity NPC35160
0.8155 Intermediate Similarity NPC87630
0.8155 Intermediate Similarity NPC116292
0.8155 Intermediate Similarity NPC179128
0.8155 Intermediate Similarity NPC162569
0.815 Intermediate Similarity NPC130489
0.815 Intermediate Similarity NPC295408
0.815 Intermediate Similarity NPC208676
0.815 Intermediate Similarity NPC150893
0.815 Intermediate Similarity NPC329960
0.8132 Intermediate Similarity NPC186746
0.8129 Intermediate Similarity NPC477736
0.8129 Intermediate Similarity NPC319404
0.8121 Intermediate Similarity NPC96447
0.8121 Intermediate Similarity NPC202391
0.8121 Intermediate Similarity NPC25491
0.8121 Intermediate Similarity NPC296659
0.8118 Intermediate Similarity NPC87403
0.8118 Intermediate Similarity NPC471874
0.8118 Intermediate Similarity NPC229354
0.8118 Intermediate Similarity NPC257847
0.8114 Intermediate Similarity NPC327694
0.8111 Intermediate Similarity NPC176246
0.8107 Intermediate Similarity NPC289021
0.8107 Intermediate Similarity NPC69425
0.8107 Intermediate Similarity NPC158546
0.8103 Intermediate Similarity NPC471493
0.8103 Intermediate Similarity NPC471858
0.8095 Intermediate Similarity NPC131405
0.8095 Intermediate Similarity NPC329657
0.8084 Intermediate Similarity NPC472936
0.8084 Intermediate Similarity NPC472938
0.8084 Intermediate Similarity NPC472937
0.8081 Intermediate Similarity NPC475378
0.8077 Intermediate Similarity NPC188217
0.807 Intermediate Similarity NPC477735
0.8068 Intermediate Similarity NPC40138
0.8068 Intermediate Similarity NPC318472
0.8066 Intermediate Similarity NPC266513
0.8061 Intermediate Similarity NPC111466
0.8059 Intermediate Similarity NPC132599
0.8059 Intermediate Similarity NPC469730
0.8059 Intermediate Similarity NPC473632
0.8059 Intermediate Similarity NPC106818
0.8059 Intermediate Similarity NPC473611
0.8059 Intermediate Similarity NPC471176
0.8057 Intermediate Similarity NPC471873
0.8057 Intermediate Similarity NPC326278
0.8056 Intermediate Similarity NPC469354
0.8056 Intermediate Similarity NPC470583
0.8056 Intermediate Similarity NPC19056
0.8047 Intermediate Similarity NPC35097
0.8047 Intermediate Similarity NPC472939
0.8045 Intermediate Similarity NPC183441
0.8045 Intermediate Similarity NPC270027
0.8034 Intermediate Similarity NPC21956
0.8012 Intermediate Similarity NPC264270
0.8012 Intermediate Similarity NPC251062
0.8012 Intermediate Similarity NPC40085
0.8012 Intermediate Similarity NPC184464
0.8011 Intermediate Similarity NPC120012
0.8 Intermediate Similarity NPC65118
0.8 Intermediate Similarity NPC473467
0.8 Intermediate Similarity NPC471134
0.8 Intermediate Similarity NPC119252
0.8 Intermediate Similarity NPC475197
0.8 Intermediate Similarity NPC471869
0.8 Intermediate Similarity NPC475379
0.7989 Intermediate Similarity NPC275477
0.7989 Intermediate Similarity NPC475058
0.7989 Intermediate Similarity NPC179914
0.7988 Intermediate Similarity NPC161955
0.7988 Intermediate Similarity NPC478234
0.7988 Intermediate Similarity NPC279442
0.7988 Intermediate Similarity NPC478123
0.7988 Intermediate Similarity NPC478236
0.7988 Intermediate Similarity NPC470617
0.7988 Intermediate Similarity NPC470616
0.7978 Intermediate Similarity NPC471859
0.7977 Intermediate Similarity NPC477623
0.7956 Intermediate Similarity NPC469438
0.7955 Intermediate Similarity NPC324769
0.7955 Intermediate Similarity NPC325732
0.7953 Intermediate Similarity NPC472549
0.7952 Intermediate Similarity NPC293154
0.7952 Intermediate Similarity NPC186296
0.7943 Intermediate Similarity NPC478125
0.7943 Intermediate Similarity NPC66193
0.7941 Intermediate Similarity NPC327962
0.7941 Intermediate Similarity NPC69367
0.7939 Intermediate Similarity NPC172311
0.7939 Intermediate Similarity NPC304110
0.7939 Intermediate Similarity NPC27518

  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 NPC475613 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
0.8222 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD7685 Pre-registration
0.7877 Intermediate Similarity NPD7799 Discontinued
0.7807 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD7228 Approved
0.7633 Intermediate Similarity NPD6190 Approved
0.7594 Intermediate Similarity NPD8434 Phase 2
0.7594 Intermediate Similarity NPD8150 Discontinued
0.7588 Intermediate Similarity NPD7236 Approved
0.7574 Intermediate Similarity NPD8166 Discontinued
0.7551 Intermediate Similarity NPD8320 Phase 1
0.7551 Intermediate Similarity NPD8319 Approved
0.7527 Intermediate Similarity NPD8313 Approved
0.7527 Intermediate Similarity NPD8312 Approved
0.75 Intermediate Similarity NPD7266 Discontinued
0.7471 Intermediate Similarity NPD7239 Suspended
0.7446 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7699 Phase 2
0.7423 Intermediate Similarity NPD7700 Phase 2
0.7419 Intermediate Similarity NPD7240 Approved
0.7403 Intermediate Similarity NPD8127 Discontinued
0.738 Intermediate Similarity NPD7808 Phase 3
0.736 Intermediate Similarity NPD8455 Phase 2
0.7351 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7251 Discontinued
0.7326 Intermediate Similarity NPD8368 Discontinued
0.7323 Intermediate Similarity NPD7435 Discontinued
0.7312 Intermediate Similarity NPD7074 Phase 3
0.7303 Intermediate Similarity NPD37 Approved
0.7302 Intermediate Similarity NPD8407 Phase 2
0.7297 Intermediate Similarity NPD3751 Discontinued
0.7293 Intermediate Similarity NPD6234 Discontinued
0.7278 Intermediate Similarity NPD4967 Phase 2
0.7278 Intermediate Similarity NPD4965 Approved
0.7278 Intermediate Similarity NPD4966 Approved
0.7273 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6797 Phase 2
0.7268 Intermediate Similarity NPD6535 Approved
0.7268 Intermediate Similarity NPD6534 Approved
0.724 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD7697 Approved
0.7236 Intermediate Similarity NPD7698 Approved
0.7236 Intermediate Similarity NPD7696 Phase 3
0.7232 Intermediate Similarity NPD7458 Discontinued
0.7228 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7472 Approved
0.7213 Intermediate Similarity NPD7199 Phase 2
0.7196 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD7874 Approved
0.7192 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD7028 Phase 2
0.7186 Intermediate Similarity NPD6663 Approved
0.7178 Intermediate Similarity NPD7701 Phase 2
0.7172 Intermediate Similarity NPD6782 Approved
0.7172 Intermediate Similarity NPD6777 Approved
0.7172 Intermediate Similarity NPD6778 Approved
0.7172 Intermediate Similarity NPD6781 Approved
0.7172 Intermediate Similarity NPD6779 Approved
0.7172 Intermediate Similarity NPD6776 Approved
0.7172 Intermediate Similarity NPD6780 Approved
0.7166 Intermediate Similarity NPD7054 Approved
0.7152 Intermediate Similarity NPD5736 Approved
0.715 Intermediate Similarity NPD8360 Approved
0.715 Intermediate Similarity NPD7497 Discontinued
0.715 Intermediate Similarity NPD8361 Approved
0.7143 Intermediate Similarity NPD8151 Discontinued
0.7143 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD7871 Phase 2
0.7114 Intermediate Similarity NPD7870 Phase 2
0.7088 Intermediate Similarity NPD7058 Phase 2
0.7088 Intermediate Similarity NPD7057 Phase 3
0.7081 Intermediate Similarity NPD3787 Discontinued
0.7073 Intermediate Similarity NPD7801 Approved
0.7073 Intermediate Similarity NPD7783 Phase 2
0.7073 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD8435 Approved
0.7049 Intermediate Similarity NPD7075 Discontinued
0.7041 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD3818 Discontinued
0.7005 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD6166 Phase 2
0.7 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.6995 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6984 Remote Similarity NPD5844 Phase 1
0.698 Remote Similarity NPD7680 Approved
0.6978 Remote Similarity NPD5760 Phase 2
0.6978 Remote Similarity NPD5761 Phase 2
0.6971 Remote Similarity NPD4628 Phase 3
0.6966 Remote Similarity NPD6273 Approved
0.6963 Remote Similarity NPD6764 Approved
0.6963 Remote Similarity NPD6765 Approved
0.6963 Remote Similarity NPD6559 Discontinued
0.6959 Remote Similarity NPD8424 Clinical (unspecified phase)
0.695 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6928 Remote Similarity NPD3094 Phase 2
0.691 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6906 Remote Similarity NPD4380 Phase 2
0.6897 Remote Similarity NPD5763 Approved
0.6897 Remote Similarity NPD5762 Approved
0.6885 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6878 Remote Similarity NPD7473 Discontinued
0.6875 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6854 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6854 Remote Similarity NPD6143 Clinical (unspecified phase)
0.685 Remote Similarity NPD8485 Approved
0.6847 Remote Similarity NPD6823 Phase 2
0.6825 Remote Similarity NPD8404 Phase 2
0.6821 Remote Similarity NPD6784 Approved
0.6821 Remote Similarity NPD6785 Approved
0.6821 Remote Similarity NPD7097 Phase 1
0.6793 Remote Similarity NPD7819 Suspended
0.6784 Remote Similarity NPD6213 Phase 3
0.6784 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6784 Remote Similarity NPD6212 Phase 3
0.6757 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7211 Clinical (unspecified phase)
0.674 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6739 Remote Similarity NPD6801 Discontinued
0.6725 Remote Similarity NPD3764 Approved
0.6721 Remote Similarity NPD6599 Discontinued
0.672 Remote Similarity NPD6232 Discontinued
0.6713 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6355 Discontinued
0.6703 Remote Similarity NPD1653 Approved
0.6702 Remote Similarity NPD5494 Approved
0.6687 Remote Similarity NPD3092 Approved
0.6667 Remote Similarity NPD3019 Approved
0.6667 Remote Similarity NPD5402 Approved
0.6667 Remote Similarity NPD2932 Approved
0.6667 Remote Similarity NPD6959 Discontinued
0.6649 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6648 Remote Similarity NPD6100 Approved
0.6648 Remote Similarity NPD6099 Approved
0.6647 Remote Similarity NPD7507 Approved
0.6647 Remote Similarity NPD4140 Approved
0.6629 Remote Similarity NPD6674 Discontinued
0.6627 Remote Similarity NPD7319 Approved
0.6613 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6613 Remote Similarity NPD1465 Phase 2
0.661 Remote Similarity NPD6002 Phase 3
0.661 Remote Similarity NPD6003 Clinical (unspecified phase)
0.661 Remote Similarity NPD6006 Clinical (unspecified phase)
0.661 Remote Similarity NPD6005 Phase 3
0.661 Remote Similarity NPD6004 Phase 3
0.6609 Remote Similarity NPD230 Phase 1
0.6606 Remote Similarity NPD8296 Approved
0.6606 Remote Similarity NPD8335 Approved
0.6606 Remote Similarity NPD8379 Approved
0.6606 Remote Similarity NPD8033 Approved
0.6606 Remote Similarity NPD8378 Approved
0.6606 Remote Similarity NPD8380 Approved
0.6606 Remote Similarity NPD7503 Approved
0.6595 Remote Similarity NPD7411 Suspended
0.659 Remote Similarity NPD7961 Discontinued
0.659 Remote Similarity NPD8032 Phase 2
0.6588 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6578 Remote Similarity NPD3817 Phase 2
0.6573 Remote Similarity NPD7930 Approved
0.6571 Remote Similarity NPD6653 Approved
0.657 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6568 Remote Similarity NPD7736 Approved
0.6561 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6559 Remote Similarity NPD1934 Approved
0.6552 Remote Similarity NPD3620 Phase 2
0.6552 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6545 Remote Similarity NPD7741 Discontinued
0.6545 Remote Similarity NPD8294 Approved
0.6545 Remote Similarity NPD3091 Approved
0.6545 Remote Similarity NPD8377 Approved
0.6543 Remote Similarity NPD3882 Suspended
0.6538 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6536 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6527 Remote Similarity NPD8328 Phase 3
0.6515 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6514 Remote Similarity NPD5735 Approved
0.6508 Remote Similarity NPD3749 Approved
0.6507 Remote Similarity NPD7999 Approved
0.6506 Remote Similarity NPD8517 Approved
0.6506 Remote Similarity NPD8515 Approved
0.6506 Remote Similarity NPD8516 Approved
0.65 Remote Similarity NPD7003 Approved
0.65 Remote Similarity NPD3750 Approved
0.6494 Remote Similarity NPD6233 Phase 2
0.6485 Remote Similarity NPD7516 Approved
0.6484 Remote Similarity NPD6799 Approved
0.6474 Remote Similarity NPD7095 Approved
0.6473 Remote Similarity NPD2493 Approved
0.6473 Remote Similarity NPD2494 Approved
0.6471 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6471 Remote Similarity NPD8059 Phase 3
0.6467 Remote Similarity NPD5403 Approved
0.6464 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6459 Remote Similarity NPD4583 Approved
0.6459 Remote Similarity NPD4582 Approved
0.6455 Remote Similarity NPD7768 Phase 2
0.6448 Remote Similarity NPD2532 Approved
0.6448 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6448 Remote Similarity NPD2534 Approved
0.6448 Remote Similarity NPD2533 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