Structure

Physi-Chem Properties

Molecular Weight:  852.38
Volume:  811.578
LogP:  0.21
LogD:  -0.153
LogS:  -3.332
# Rotatable Bonds:  9
TPSA:  284.73
# H-Bond Aceptor:  18
# H-Bond Donor:  9
# Rings:  8
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.105
Synthetic Accessibility Score:  6.241
Fsp3:  0.81
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.501
MDCK Permeability:  0.00013191960169933736
Pgp-inhibitor:  0.009
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.999
20% Bioavailability (F20%):  0.477
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.185
Plasma Protein Binding (PPB):  48.16033172607422%
Volume Distribution (VD):  0.55
Pgp-substrate:  19.473241806030273%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.87
CYP2C19-inhibitor:  0.006
CYP2C19-substrate:  0.117
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.016
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.043
CYP3A4-inhibitor:  0.202
CYP3A4-substrate:  0.031

ADMET: Excretion

Clearance (CL):  0.648
Half-life (T1/2):  0.617

ADMET: Toxicity

hERG Blockers:  0.268
Human Hepatotoxicity (H-HT):  0.203
Drug-inuced Liver Injury (DILI):  0.079
AMES Toxicity:  0.083
Rat Oral Acute Toxicity:  0.754
Maximum Recommended Daily Dose:  0.467
Skin Sensitization:  0.303
Carcinogencity:  0.448
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.977

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

  Natural Product: NPC127656

Natural Product ID:  NPC127656
Common Name*:   14Beta-Hydroxy-19Beta-Oxobufa-4,20,22-Trienolide-3Beta-O-{Alpha-L-Rhamnopyranosyl-[(1->4)-Beta-D-Glucopyranosyl]-(1->3)-Alpha-L-Rhamnopyranoside}
IUPAC Name:   (3S,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[(2R,3R,4S,5S,6S)-3-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(6-oxopyran-3-yl)-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms:  
Standard InCHIKey:  YLZRFBHMEILVSF-RESWNAECSA-N
Standard InCHI:  InChI=1S/C42H60O18/c1-18-28(46)30(48)32(50)37(55-18)60-36-34(52)39(56-19(2)35(36)59-38-33(51)31(49)29(47)26(15-43)58-38)57-22-8-12-41(17-44)21(14-22)5-6-25-24(41)9-11-40(3)23(10-13-42(25,40)53)20-4-7-27(45)54-16-20/h4,7,14,16-19,22-26,28-39,43,46-53H,5-6,8-13,15H2,1-3H3/t18-,19-,22-,23+,24-,25+,26+,28-,29+,30+,31-,32+,33+,34+,35-,36-,37-,38-,39-,40+,41+,42-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@H]([C@@H](O[C@@H](C)[C@@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1CC[C@@]2(C=O)C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](CC[C@]12O)c1ccc(=O)oc1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2375663
PubChem CID:   71713251
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001125] Steroid lactones
          • [CHEMONTID:0001557] Bufanolides and derivatives

*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
NPO27354 Urginea depressa Species Hyacinthaceae Eukaryota n.a. n.a. n.a. PMID[23659371]
NPO27354 Urginea depressa Species Hyacinthaceae 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
NPT179 Cell Line A2780 Homo sapiens IC50 = 41.0 nM PMID[520724]
NPT1383 Cell Line A2058 Homo sapiens IC50 = 76.0 nM PMID[520724]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 51.0 nM PMID[520724]

☑ 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 NPC127656 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
0.9677 High Similarity NPC155529
0.9603 High Similarity NPC158350
0.9274 High Similarity NPC179261
0.9225 High Similarity NPC62172
0.9225 High Similarity NPC289700
0.9084 High Similarity NPC75616
0.8906 High Similarity NPC125077
0.8906 High Similarity NPC329986
0.8906 High Similarity NPC276838
0.8906 High Similarity NPC232785
0.8906 High Similarity NPC188234
0.8906 High Similarity NPC140092
0.8855 High Similarity NPC194716
0.8846 High Similarity NPC477709
0.8846 High Similarity NPC476221
0.8788 High Similarity NPC329675
0.8779 High Similarity NPC248703
0.8779 High Similarity NPC329636
0.875 High Similarity NPC329784
0.875 High Similarity NPC240070
0.8702 High Similarity NPC247190
0.8702 High Similarity NPC32793
0.8702 High Similarity NPC469749
0.8702 High Similarity NPC146857
0.8702 High Similarity NPC116075
0.8692 High Similarity NPC16569
0.8692 High Similarity NPC253456
0.8692 High Similarity NPC159338
0.8692 High Similarity NPC173347
0.8672 High Similarity NPC250556
0.8672 High Similarity NPC469750
0.8647 High Similarity NPC59288
0.8626 High Similarity NPC471855
0.8626 High Similarity NPC42670
0.8626 High Similarity NPC19124
0.8626 High Similarity NPC93416
0.8615 High Similarity NPC91
0.8605 High Similarity NPC471356
0.8605 High Similarity NPC179412
0.8561 High Similarity NPC157817
0.8561 High Similarity NPC225385
0.8561 High Similarity NPC142756
0.8561 High Similarity NPC104585
0.8561 High Similarity NPC298783
0.855 High Similarity NPC213634
0.8538 High Similarity NPC245094
0.8519 High Similarity NPC290746
0.8519 High Similarity NPC79250
0.8516 High Similarity NPC27363
0.8516 High Similarity NPC219804
0.8473 Intermediate Similarity NPC476966
0.8473 Intermediate Similarity NPC469752
0.8473 Intermediate Similarity NPC471407
0.8473 Intermediate Similarity NPC86159
0.8473 Intermediate Similarity NPC471359
0.8473 Intermediate Similarity NPC9499
0.8473 Intermediate Similarity NPC471358
0.8473 Intermediate Similarity NPC89514
0.8473 Intermediate Similarity NPC180079
0.8473 Intermediate Similarity NPC471360
0.8473 Intermediate Similarity NPC469751
0.8473 Intermediate Similarity NPC10823
0.8473 Intermediate Similarity NPC219085
0.8473 Intermediate Similarity NPC469753
0.8473 Intermediate Similarity NPC17896
0.8473 Intermediate Similarity NPC284406
0.8473 Intermediate Similarity NPC251866
0.8473 Intermediate Similarity NPC70542
0.8473 Intermediate Similarity NPC471361
0.8473 Intermediate Similarity NPC469754
0.8473 Intermediate Similarity NPC6108
0.8473 Intermediate Similarity NPC471352
0.8473 Intermediate Similarity NPC197707
0.8473 Intermediate Similarity NPC469755
0.8425 Intermediate Similarity NPC135369
0.8421 Intermediate Similarity NPC316915
0.8397 Intermediate Similarity NPC220838
0.8397 Intermediate Similarity NPC45606
0.8397 Intermediate Similarity NPC311534
0.8385 Intermediate Similarity NPC297950
0.8372 Intermediate Similarity NPC55602
0.8372 Intermediate Similarity NPC41129
0.8359 Intermediate Similarity NPC120390
0.8359 Intermediate Similarity NPC475590
0.8359 Intermediate Similarity NPC475419
0.8359 Intermediate Similarity NPC474908
0.8346 Intermediate Similarity NPC231240
0.8321 Intermediate Similarity NPC117702
0.8321 Intermediate Similarity NPC146456
0.8321 Intermediate Similarity NPC469757
0.8321 Intermediate Similarity NPC471357
0.8308 Intermediate Similarity NPC318135
0.8296 Intermediate Similarity NPC110700
0.8296 Intermediate Similarity NPC279915
0.8295 Intermediate Similarity NPC28532
0.8295 Intermediate Similarity NPC474423
0.8295 Intermediate Similarity NPC74259
0.8284 Intermediate Similarity NPC476779
0.8281 Intermediate Similarity NPC145074
0.8281 Intermediate Similarity NPC470312
0.8281 Intermediate Similarity NPC41123
0.8281 Intermediate Similarity NPC476150
0.8281 Intermediate Similarity NPC114939
0.8281 Intermediate Similarity NPC72260
0.8281 Intermediate Similarity NPC476127
0.8271 Intermediate Similarity NPC311178
0.8271 Intermediate Similarity NPC241008
0.8271 Intermediate Similarity NPC300655
0.8271 Intermediate Similarity NPC477493
0.8271 Intermediate Similarity NPC43589
0.8271 Intermediate Similarity NPC222951
0.8268 Intermediate Similarity NPC473617
0.8268 Intermediate Similarity NPC45475
0.8268 Intermediate Similarity NPC473828
0.8258 Intermediate Similarity NPC472269
0.8258 Intermediate Similarity NPC23020
0.8258 Intermediate Similarity NPC473888
0.8258 Intermediate Similarity NPC472268
0.8258 Intermediate Similarity NPC112492
0.8258 Intermediate Similarity NPC472270
0.8244 Intermediate Similarity NPC159499
0.8235 Intermediate Similarity NPC190065
0.8235 Intermediate Similarity NPC141215
0.8235 Intermediate Similarity NPC471089
0.8231 Intermediate Similarity NPC308262
0.8231 Intermediate Similarity NPC117445
0.8231 Intermediate Similarity NPC208193
0.8222 Intermediate Similarity NPC476777
0.8222 Intermediate Similarity NPC476778
0.8217 Intermediate Similarity NPC170084
0.8217 Intermediate Similarity NPC173555
0.8217 Intermediate Similarity NPC202051
0.8217 Intermediate Similarity NPC314535
0.8217 Intermediate Similarity NPC476204
0.8209 Intermediate Similarity NPC233223
0.8209 Intermediate Similarity NPC475444
0.8209 Intermediate Similarity NPC477195
0.8209 Intermediate Similarity NPC473679
0.8209 Intermediate Similarity NPC183816
0.8209 Intermediate Similarity NPC475177
0.8209 Intermediate Similarity NPC322904
0.8209 Intermediate Similarity NPC319719
0.8209 Intermediate Similarity NPC324933
0.8209 Intermediate Similarity NPC196874
0.8203 Intermediate Similarity NPC469756
0.8203 Intermediate Similarity NPC236973
0.8203 Intermediate Similarity NPC5292
0.8203 Intermediate Similarity NPC219656
0.8203 Intermediate Similarity NPC55532
0.8203 Intermediate Similarity NPC270850
0.8203 Intermediate Similarity NPC292467
0.8203 Intermediate Similarity NPC470897
0.8203 Intermediate Similarity NPC305260
0.8203 Intermediate Similarity NPC32177
0.8203 Intermediate Similarity NPC30483
0.8182 Intermediate Similarity NPC152091
0.8175 Intermediate Similarity NPC140045
0.8175 Intermediate Similarity NPC295885
0.8175 Intermediate Similarity NPC596
0.8168 Intermediate Similarity NPC471090
0.8168 Intermediate Similarity NPC190846
0.8168 Intermediate Similarity NPC277191
0.8168 Intermediate Similarity NPC473505
0.8162 Intermediate Similarity NPC171619
0.8162 Intermediate Similarity NPC262813
0.8154 Intermediate Similarity NPC264336
0.8154 Intermediate Similarity NPC193893
0.814 Intermediate Similarity NPC184555
0.814 Intermediate Similarity NPC475556
0.814 Intermediate Similarity NPC107607
0.814 Intermediate Similarity NPC475629
0.814 Intermediate Similarity NPC79579
0.8125 Intermediate Similarity NPC218093
0.8125 Intermediate Similarity NPC13710
0.8125 Intermediate Similarity NPC471548
0.8125 Intermediate Similarity NPC153440
0.812 Intermediate Similarity NPC477490
0.812 Intermediate Similarity NPC293623
0.812 Intermediate Similarity NPC168899
0.812 Intermediate Similarity NPC69273
0.812 Intermediate Similarity NPC114306
0.811 Intermediate Similarity NPC190286
0.811 Intermediate Similarity NPC207637
0.8102 Intermediate Similarity NPC477236
0.8102 Intermediate Similarity NPC251998
0.8095 Intermediate Similarity NPC73050
0.8095 Intermediate Similarity NPC260665
0.8092 Intermediate Similarity NPC6193
0.8077 Intermediate Similarity NPC233500
0.8077 Intermediate Similarity NPC42675
0.8077 Intermediate Similarity NPC231518
0.8077 Intermediate Similarity NPC40749
0.8077 Intermediate Similarity NPC475182
0.8077 Intermediate Similarity NPC475219
0.8077 Intermediate Similarity NPC46570
0.8074 Intermediate Similarity NPC478154
0.8074 Intermediate Similarity NPC476776
0.8074 Intermediate Similarity NPC473805
0.8074 Intermediate Similarity NPC473519
0.8074 Intermediate Similarity NPC312650

  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 NPC127656 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
0.8952 High Similarity NPD7503 Approved
0.8672 High Similarity NPD7507 Approved
0.8473 Intermediate Similarity NPD7319 Approved
0.8281 Intermediate Similarity NPD8377 Approved
0.8281 Intermediate Similarity NPD8294 Approved
0.8217 Intermediate Similarity NPD8378 Approved
0.8217 Intermediate Similarity NPD8380 Approved
0.8217 Intermediate Similarity NPD8296 Approved
0.8217 Intermediate Similarity NPD8379 Approved
0.8217 Intermediate Similarity NPD8335 Approved
0.8095 Intermediate Similarity NPD8133 Approved
0.8077 Intermediate Similarity NPD8033 Approved
0.7939 Intermediate Similarity NPD8513 Phase 3
0.7852 Intermediate Similarity NPD7736 Approved
0.7846 Intermediate Similarity NPD7328 Approved
0.7846 Intermediate Similarity NPD7327 Approved
0.784 Intermediate Similarity NPD6686 Approved
0.7803 Intermediate Similarity NPD8517 Approved
0.7803 Intermediate Similarity NPD8516 Approved
0.7803 Intermediate Similarity NPD8515 Approved
0.7786 Intermediate Similarity NPD7516 Approved
0.776 Intermediate Similarity NPD6412 Phase 2
0.7687 Intermediate Similarity NPD8328 Phase 3
0.7612 Intermediate Similarity NPD6370 Approved
0.7597 Intermediate Similarity NPD8297 Approved
0.7597 Intermediate Similarity NPD6882 Approved
0.7518 Intermediate Similarity NPD8293 Discontinued
0.75 Intermediate Similarity NPD7492 Approved
0.75 Intermediate Similarity NPD6009 Approved
0.7463 Intermediate Similarity NPD6054 Approved
0.7463 Intermediate Similarity NPD6319 Approved
0.7445 Intermediate Similarity NPD6616 Approved
0.7405 Intermediate Similarity NPD4632 Approved
0.7391 Intermediate Similarity NPD7078 Approved
0.7368 Intermediate Similarity NPD7115 Discovery
0.7328 Intermediate Similarity NPD6053 Discontinued
0.7287 Intermediate Similarity NPD6881 Approved
0.7287 Intermediate Similarity NPD6899 Approved
0.7279 Intermediate Similarity NPD6015 Approved
0.7279 Intermediate Similarity NPD6016 Approved
0.7252 Intermediate Similarity NPD6650 Approved
0.7252 Intermediate Similarity NPD8130 Phase 1
0.7252 Intermediate Similarity NPD6649 Approved
0.7239 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD5988 Approved
0.7209 Intermediate Similarity NPD5697 Approved
0.7206 Intermediate Similarity NPD6059 Approved
0.7176 Intermediate Similarity NPD7102 Approved
0.7176 Intermediate Similarity NPD7290 Approved
0.7176 Intermediate Similarity NPD6883 Approved
0.7132 Intermediate Similarity NPD5739 Approved
0.7132 Intermediate Similarity NPD6402 Approved
0.7132 Intermediate Similarity NPD7128 Approved
0.7132 Intermediate Similarity NPD6675 Approved
0.7121 Intermediate Similarity NPD6847 Approved
0.7121 Intermediate Similarity NPD6617 Approved
0.7121 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD6869 Approved
0.7099 Intermediate Similarity NPD6012 Approved
0.7099 Intermediate Similarity NPD6373 Approved
0.7099 Intermediate Similarity NPD6372 Approved
0.7099 Intermediate Similarity NPD6013 Approved
0.7099 Intermediate Similarity NPD6014 Approved
0.7063 Intermediate Similarity NPD7638 Approved
0.7054 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD7604 Phase 2
0.7029 Intermediate Similarity NPD5983 Phase 2
0.7023 Intermediate Similarity NPD7320 Approved
0.7023 Intermediate Similarity NPD6011 Approved
0.7008 Intermediate Similarity NPD7640 Approved
0.7008 Intermediate Similarity NPD7639 Approved
0.695 Remote Similarity NPD6336 Discontinued
0.6947 Remote Similarity NPD5701 Approved
0.6917 Remote Similarity NPD4634 Approved
0.6901 Remote Similarity NPD8074 Phase 3
0.6899 Remote Similarity NPD5211 Phase 2
0.6875 Remote Similarity NPD5285 Approved
0.6875 Remote Similarity NPD5286 Approved
0.6875 Remote Similarity NPD4696 Approved
0.6842 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6828 Remote Similarity NPD7260 Phase 2
0.6797 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6794 Remote Similarity NPD5141 Approved
0.6769 Remote Similarity NPD5225 Approved
0.6769 Remote Similarity NPD5226 Approved
0.6769 Remote Similarity NPD4633 Approved
0.6769 Remote Similarity NPD5224 Approved
0.6763 Remote Similarity NPD7101 Approved
0.6763 Remote Similarity NPD7100 Approved
0.6742 Remote Similarity NPD6008 Approved
0.6741 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6736 Remote Similarity NPD6033 Approved
0.6726 Remote Similarity NPD7799 Discontinued
0.6719 Remote Similarity NPD4755 Approved
0.6719 Remote Similarity NPD6084 Phase 2
0.6719 Remote Similarity NPD6083 Phase 2
0.6718 Remote Similarity NPD5175 Approved
0.6718 Remote Similarity NPD5174 Approved
0.6692 Remote Similarity NPD5223 Approved
0.6691 Remote Similarity NPD6335 Approved
0.669 Remote Similarity NPD6067 Discontinued
0.6667 Remote Similarity NPD8448 Approved
0.6667 Remote Similarity NPD6274 Approved
0.6667 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6645 Remote Similarity NPD7625 Phase 1
0.6644 Remote Similarity NPD8391 Approved
0.6644 Remote Similarity NPD8392 Approved
0.6644 Remote Similarity NPD8390 Approved
0.6642 Remote Similarity NPD4730 Approved
0.6642 Remote Similarity NPD4729 Approved
0.6642 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6619 Remote Similarity NPD6317 Approved
0.6615 Remote Similarity NPD4700 Approved
0.6597 Remote Similarity NPD8451 Approved
0.6587 Remote Similarity NPD6079 Approved
0.6573 Remote Similarity NPD7830 Approved
0.6573 Remote Similarity NPD7829 Approved
0.6571 Remote Similarity NPD6313 Approved
0.6571 Remote Similarity NPD6314 Approved
0.6544 Remote Similarity NPD5251 Approved
0.6544 Remote Similarity NPD5249 Phase 3
0.6544 Remote Similarity NPD5248 Approved
0.6544 Remote Similarity NPD5250 Approved
0.6544 Remote Similarity NPD5247 Approved
0.6515 Remote Similarity NPD7632 Discontinued
0.6493 Remote Similarity NPD4767 Approved
0.6493 Remote Similarity NPD4768 Approved
0.6484 Remote Similarity NPD7748 Approved
0.6462 Remote Similarity NPD7902 Approved
0.6457 Remote Similarity NPD5281 Approved
0.6457 Remote Similarity NPD5284 Approved
0.6444 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6444 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6443 Remote Similarity NPD6845 Suspended
0.6434 Remote Similarity NPD6909 Approved
0.6434 Remote Similarity NPD6908 Approved
0.6434 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6434 Remote Similarity NPD5695 Phase 3
0.6429 Remote Similarity NPD5328 Approved
0.6423 Remote Similarity NPD6371 Approved
0.6419 Remote Similarity NPD5956 Approved
0.6414 Remote Similarity NPD8340 Approved
0.6414 Remote Similarity NPD8341 Approved
0.6414 Remote Similarity NPD8342 Approved
0.6414 Remote Similarity NPD8299 Approved
0.6412 Remote Similarity NPD5696 Approved
0.6412 Remote Similarity NPD4225 Approved
0.6406 Remote Similarity NPD4202 Approved
0.6406 Remote Similarity NPD8171 Discontinued
0.6397 Remote Similarity NPD5128 Approved
0.6395 Remote Similarity NPD8337 Approved
0.6395 Remote Similarity NPD8336 Approved
0.6385 Remote Similarity NPD5222 Approved
0.6385 Remote Similarity NPD5221 Approved
0.6385 Remote Similarity NPD4697 Phase 3
0.6385 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6382 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6378 Remote Similarity NPD46 Approved
0.6378 Remote Similarity NPD6698 Approved
0.6378 Remote Similarity NPD7838 Discovery
0.6377 Remote Similarity NPD5217 Approved
0.6377 Remote Similarity NPD5215 Approved
0.6377 Remote Similarity NPD5216 Approved
0.6352 Remote Similarity NPD7236 Approved
0.6349 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6343 Remote Similarity NPD4754 Approved
0.6338 Remote Similarity NPD7641 Discontinued
0.6336 Remote Similarity NPD5173 Approved
0.6328 Remote Similarity NPD6411 Approved
0.6328 Remote Similarity NPD7515 Phase 2
0.6328 Remote Similarity NPD7983 Approved
0.6328 Remote Similarity NPD5693 Phase 1
0.632 Remote Similarity NPD6684 Approved
0.632 Remote Similarity NPD6409 Approved
0.632 Remote Similarity NPD7146 Approved
0.632 Remote Similarity NPD5330 Approved
0.632 Remote Similarity NPD7521 Approved
0.632 Remote Similarity NPD7334 Approved
0.6312 Remote Similarity NPD6868 Approved
0.6308 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6308 Remote Similarity NPD5210 Approved
0.6308 Remote Similarity NPD4629 Approved
0.6304 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6304 Remote Similarity NPD5135 Approved
0.6304 Remote Similarity NPD5169 Approved
0.6299 Remote Similarity NPD4753 Phase 2
0.6291 Remote Similarity NPD8450 Suspended
0.6279 Remote Similarity NPD5778 Approved
0.6279 Remote Similarity NPD6399 Phase 3
0.6279 Remote Similarity NPD5779 Approved
0.627 Remote Similarity NPD3573 Approved
0.6259 Remote Similarity NPD5127 Approved
0.6258 Remote Similarity NPD7239 Suspended
0.6233 Remote Similarity NPD7642 Approved
0.6231 Remote Similarity NPD7900 Approved
0.6231 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6225 Remote Similarity NPD8449 Approved
0.6225 Remote Similarity NPD8338 Approved
0.622 Remote Similarity NPD6903 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