Structure

Physi-Chem Properties

Molecular Weight:  532.38
Volume:  572.634
LogP:  3.972
LogD:  3.296
LogS:  -4.285
# Rotatable Bonds:  7
TPSA:  104.06
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.314
Synthetic Accessibility Score:  5.193
Fsp3:  0.875
Lipinski Rule-of-5:  Accepted
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:  -5.215
MDCK Permeability:  1.80344759428408e-05
Pgp-inhibitor:  0.987
Pgp-substrate:  0.295
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.784
30% Bioavailability (F30%):  0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.717
Plasma Protein Binding (PPB):  89.21283721923828%
Volume Distribution (VD):  0.95
Pgp-substrate:  4.706972599029541%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.248
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.915
CYP2C9-inhibitor:  0.161
CYP2C9-substrate:  0.289
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.081
CYP3A4-inhibitor:  0.796
CYP3A4-substrate:  0.753

ADMET: Excretion

Clearance (CL):  4.778
Half-life (T1/2):  0.264

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.26
Drug-inuced Liver Injury (DILI):  0.123
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.083
Maximum Recommended Daily Dose:  0.822
Skin Sensitization:  0.035
Carcinogencity:  0.232
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.961

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

  Natural Product: NPC473415

Natural Product ID:  NPC473415
Common Name*:   [(3R,4S,6R)-2,4-Dihydroxy-6-[(8S,10S,11S,14R)-11-Hydroxy-4,4,8,10,14-Pentamethyl-3-Oxo-1,2,5,6,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-17-Yl]-2-Methylheptan-3-Yl] Acetate
IUPAC Name:   [(3R,4S,6R)-2,4-dihydroxy-6-[(8S,10S,11S,14R)-11-hydroxy-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-yl] acetate
Synonyms:  
Standard InCHIKey:  WXHUQVMHWUQNTG-CPQDFQMASA-N
Standard InCHI:  InChI=1S/C32H52O6/c1-18(16-23(35)27(29(5,6)37)38-19(2)33)20-10-14-31(8)21(20)17-22(34)26-30(7)13-12-25(36)28(3,4)24(30)11-15-32(26,31)9/h18,22-24,26-27,34-35,37H,10-17H2,1-9H3/t18-,22+,23+,24?,26?,27-,30+,31+,32+/m1/s1
SMILES:  CC(CC(C(C(C)(C)O)OC(=O)C)O)C1=C2CC(C3C4(CCC(=O)C(C4CCC3(C2(CC1)C)C)(C)C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL421397
PubChem CID:   10075759
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO30648 Alisma orientale Species Alismataceae Eukaryota rhizome n.a. n.a. PMID[10560729]
NPO30648 Alisma orientale Species Alismataceae Eukaryota n.a. rhizome n.a. PMID[17541191]
NPO30648 Alisma orientale Species Alismataceae Eukaryota Rhizome n.a. n.a. PMID[26425784]
NPO30648 Alisma orientale Species Alismataceae Eukaryota n.a. tuber n.a. PMID[26666273]
NPO30648 Alisma orientale Species Alismataceae Eukaryota n.a. n.a. n.a. Database[HerDing]

☑ 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
NPT32 Organism Mus musculus Mus musculus Inhibition = -2.9 % PMID[544607]
NPT32 Organism Mus musculus Mus musculus Inhibition = 6.4 % PMID[544607]
NPT32 Organism Mus musculus Mus musculus Inhibition = 13.4 % PMID[544607]
NPT32 Organism Mus musculus Mus musculus Inhibition = 71.0 % PMID[544607]
NPT32 Organism Mus musculus Mus musculus Inhibition = 111.5 % PMID[544607]
NPT32 Organism Mus musculus Mus musculus IC50 > 10000.0 nM PMID[544607]

☑ 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 NPC473415 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 NPC37787
1.0 High Similarity NPC469329
1.0 High Similarity NPC30677
1.0 High Similarity NPC180557
0.9667 High Similarity NPC471777
0.9659 High Similarity NPC473166
0.9362 High Similarity NPC469316
0.9333 High Similarity NPC198074
0.9333 High Similarity NPC274046
0.9263 High Similarity NPC324001
0.9255 High Similarity NPC469327
0.9231 High Similarity NPC240617
0.9205 High Similarity NPC241875
0.9205 High Similarity NPC469317
0.9205 High Similarity NPC469314
0.9032 High Similarity NPC471822
0.898 High Similarity NPC469318
0.898 High Similarity NPC473173
0.898 High Similarity NPC471783
0.898 High Similarity NPC9457
0.8878 High Similarity NPC470587
0.8842 High Similarity NPC471784
0.8842 High Similarity NPC303777
0.8778 High Similarity NPC469322
0.875 High Similarity NPC86370
0.871 High Similarity NPC469315
0.8687 High Similarity NPC472655
0.8614 High Similarity NPC41405
0.8602 High Similarity NPC473167
0.8587 High Similarity NPC469319
0.8587 High Similarity NPC229871
0.8529 High Similarity NPC5284
0.8526 High Similarity NPC279974
0.8485 Intermediate Similarity NPC264048
0.8469 Intermediate Similarity NPC54909
0.8469 Intermediate Similarity NPC476897
0.8469 Intermediate Similarity NPC233012
0.8454 Intermediate Similarity NPC470066
0.8454 Intermediate Similarity NPC119036
0.8454 Intermediate Similarity NPC470068
0.8454 Intermediate Similarity NPC470067
0.8438 Intermediate Similarity NPC230151
0.8431 Intermediate Similarity NPC218853
0.8421 Intermediate Similarity NPC159410
0.8404 Intermediate Similarity NPC235704
0.8384 Intermediate Similarity NPC473163
0.8367 Intermediate Similarity NPC473176
0.8367 Intermediate Similarity NPC167974
0.8365 Intermediate Similarity NPC470063
0.8365 Intermediate Similarity NPC234042
0.8365 Intermediate Similarity NPC152117
0.835 Intermediate Similarity NPC250956
0.8333 Intermediate Similarity NPC473170
0.8317 Intermediate Similarity NPC475414
0.8317 Intermediate Similarity NPC173172
0.8316 Intermediate Similarity NPC107674
0.8316 Intermediate Similarity NPC86368
0.8316 Intermediate Similarity NPC141497
0.8316 Intermediate Similarity NPC170220
0.8298 Intermediate Similarity NPC471896
0.8298 Intermediate Similarity NPC473269
0.8286 Intermediate Similarity NPC255017
0.8283 Intermediate Similarity NPC470054
0.8261 Intermediate Similarity NPC73038
0.8261 Intermediate Similarity NPC56588
0.8261 Intermediate Similarity NPC325594
0.8252 Intermediate Similarity NPC5475
0.8252 Intermediate Similarity NPC173905
0.8252 Intermediate Similarity NPC475065
0.8252 Intermediate Similarity NPC284828
0.8252 Intermediate Similarity NPC472216
0.8247 Intermediate Similarity NPC120708
0.8247 Intermediate Similarity NPC327179
0.8247 Intermediate Similarity NPC327788
0.8235 Intermediate Similarity NPC475176
0.8235 Intermediate Similarity NPC473165
0.8235 Intermediate Similarity NPC473284
0.8235 Intermediate Similarity NPC255387
0.8235 Intermediate Similarity NPC131665
0.8229 Intermediate Similarity NPC296164
0.8218 Intermediate Similarity NPC471293
0.8211 Intermediate Similarity NPC26888
0.8211 Intermediate Similarity NPC189520
0.8211 Intermediate Similarity NPC212301
0.8211 Intermediate Similarity NPC470590
0.8211 Intermediate Similarity NPC86266
0.8211 Intermediate Similarity NPC77099
0.8211 Intermediate Similarity NPC110657
0.8211 Intermediate Similarity NPC60755
0.8211 Intermediate Similarity NPC285184
0.82 Intermediate Similarity NPC296879
0.82 Intermediate Similarity NPC473928
0.82 Intermediate Similarity NPC470053
0.82 Intermediate Similarity NPC477054
0.82 Intermediate Similarity NPC471119
0.8191 Intermediate Similarity NPC474704
0.8191 Intermediate Similarity NPC250592
0.8191 Intermediate Similarity NPC32830
0.8191 Intermediate Similarity NPC475921
0.8191 Intermediate Similarity NPC77263
0.8191 Intermediate Similarity NPC474889
0.8191 Intermediate Similarity NPC30522
0.8173 Intermediate Similarity NPC470065
0.8172 Intermediate Similarity NPC138756
0.8163 Intermediate Similarity NPC259788
0.8163 Intermediate Similarity NPC255589
0.8163 Intermediate Similarity NPC247139
0.8163 Intermediate Similarity NPC9613
0.8155 Intermediate Similarity NPC472217
0.8155 Intermediate Similarity NPC472219
0.8155 Intermediate Similarity NPC258323
0.8155 Intermediate Similarity NPC475418
0.8155 Intermediate Similarity NPC318363
0.8155 Intermediate Similarity NPC472218
0.8155 Intermediate Similarity NPC473482
0.8144 Intermediate Similarity NPC195715
0.8144 Intermediate Similarity NPC32118
0.8144 Intermediate Similarity NPC473648
0.8137 Intermediate Similarity NPC477877
0.8137 Intermediate Similarity NPC475494
0.8125 Intermediate Similarity NPC473690
0.8125 Intermediate Similarity NPC287118
0.8125 Intermediate Similarity NPC136313
0.8125 Intermediate Similarity NPC471902
0.8125 Intermediate Similarity NPC275809
0.8125 Intermediate Similarity NPC477435
0.8125 Intermediate Similarity NPC307335
0.8125 Intermediate Similarity NPC133579
0.8125 Intermediate Similarity NPC477436
0.8125 Intermediate Similarity NPC474806
0.8125 Intermediate Similarity NPC74855
0.8119 Intermediate Similarity NPC471005
0.8119 Intermediate Similarity NPC222153
0.8119 Intermediate Similarity NPC218513
0.8119 Intermediate Similarity NPC55954
0.8105 Intermediate Similarity NPC175628
0.8105 Intermediate Similarity NPC111110
0.8105 Intermediate Similarity NPC111585
0.8105 Intermediate Similarity NPC472307
0.8105 Intermediate Similarity NPC474728
0.8105 Intermediate Similarity NPC120840
0.8105 Intermediate Similarity NPC113989
0.8105 Intermediate Similarity NPC49320
0.8105 Intermediate Similarity NPC126369
0.8105 Intermediate Similarity NPC148414
0.8105 Intermediate Similarity NPC470589
0.81 Intermediate Similarity NPC477052
0.81 Intermediate Similarity NPC477051
0.81 Intermediate Similarity NPC289670
0.81 Intermediate Similarity NPC115899
0.81 Intermediate Similarity NPC477053
0.8085 Intermediate Similarity NPC242864
0.8085 Intermediate Similarity NPC255176
0.8085 Intermediate Similarity NPC4309
0.8077 Intermediate Similarity NPC477070
0.8077 Intermediate Similarity NPC477069
0.8065 Intermediate Similarity NPC324063
0.8065 Intermediate Similarity NPC471737
0.8061 Intermediate Similarity NPC73004
0.8061 Intermediate Similarity NPC204961
0.8061 Intermediate Similarity NPC158371
0.8061 Intermediate Similarity NPC88847
0.8061 Intermediate Similarity NPC173744
0.8061 Intermediate Similarity NPC259733
0.8061 Intermediate Similarity NPC207922
0.8061 Intermediate Similarity NPC471039
0.8058 Intermediate Similarity NPC329048
0.8058 Intermediate Similarity NPC330011
0.8043 Intermediate Similarity NPC473157
0.8043 Intermediate Similarity NPC171789
0.8041 Intermediate Similarity NPC231063
0.8041 Intermediate Similarity NPC191412
0.8041 Intermediate Similarity NPC263548
0.8041 Intermediate Similarity NPC88116
0.8041 Intermediate Similarity NPC49670
0.8041 Intermediate Similarity NPC114159
0.8041 Intermediate Similarity NPC78580
0.8041 Intermediate Similarity NPC145667
0.8041 Intermediate Similarity NPC74751
0.8041 Intermediate Similarity NPC282395
0.8041 Intermediate Similarity NPC174051
0.8041 Intermediate Similarity NPC6818
0.8041 Intermediate Similarity NPC23621
0.8041 Intermediate Similarity NPC184006
0.8041 Intermediate Similarity NPC20235
0.8041 Intermediate Similarity NPC67831
0.8041 Intermediate Similarity NPC299996
0.8041 Intermediate Similarity NPC32407
0.8039 Intermediate Similarity NPC473175
0.8039 Intermediate Similarity NPC470060
0.8039 Intermediate Similarity NPC65523
0.8039 Intermediate Similarity NPC470064
0.8039 Intermediate Similarity NPC470061
0.8039 Intermediate Similarity NPC470062
0.8039 Intermediate Similarity NPC470043
0.8039 Intermediate Similarity NPC470059
0.8039 Intermediate Similarity NPC470057
0.8039 Intermediate Similarity NPC470058
0.8037 Intermediate Similarity NPC284915
0.8021 Intermediate Similarity NPC71074

  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 NPC473415 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
0.8041 Intermediate Similarity NPD7748 Approved
0.7938 Intermediate Similarity NPD6399 Phase 3
0.785 Intermediate Similarity NPD8297 Approved
0.7835 Intermediate Similarity NPD8035 Phase 2
0.7835 Intermediate Similarity NPD7515 Phase 2
0.7835 Intermediate Similarity NPD8034 Phase 2
0.78 Intermediate Similarity NPD7902 Approved
0.7788 Intermediate Similarity NPD7128 Approved
0.7788 Intermediate Similarity NPD5739 Approved
0.7788 Intermediate Similarity NPD6675 Approved
0.7788 Intermediate Similarity NPD6402 Approved
0.7766 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD7115 Discovery
0.766 Intermediate Similarity NPD4786 Approved
0.7642 Intermediate Similarity NPD7320 Approved
0.7642 Intermediate Similarity NPD6881 Approved
0.7642 Intermediate Similarity NPD6899 Approved
0.7634 Intermediate Similarity NPD3667 Approved
0.7624 Intermediate Similarity NPD6084 Phase 2
0.7624 Intermediate Similarity NPD6083 Phase 2
0.7593 Intermediate Similarity NPD8130 Phase 1
0.757 Intermediate Similarity NPD6372 Approved
0.757 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.757 Intermediate Similarity NPD6373 Approved
0.7556 Intermediate Similarity NPD6117 Approved
0.7549 Intermediate Similarity NPD7638 Approved
0.7547 Intermediate Similarity NPD5701 Approved
0.7547 Intermediate Similarity NPD5697 Approved
0.75 Intermediate Similarity NPD7290 Approved
0.75 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6883 Approved
0.75 Intermediate Similarity NPD3618 Phase 1
0.75 Intermediate Similarity NPD7102 Approved
0.75 Intermediate Similarity NPD7900 Approved
0.7476 Intermediate Similarity NPD7640 Approved
0.7476 Intermediate Similarity NPD7639 Approved
0.7473 Intermediate Similarity NPD6116 Phase 1
0.7449 Intermediate Similarity NPD5328 Approved
0.7431 Intermediate Similarity NPD6617 Approved
0.7431 Intermediate Similarity NPD6869 Approved
0.7431 Intermediate Similarity NPD6847 Approved
0.7431 Intermediate Similarity NPD6649 Approved
0.7431 Intermediate Similarity NPD6650 Approved
0.7411 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD6012 Approved
0.7407 Intermediate Similarity NPD6013 Approved
0.7407 Intermediate Similarity NPD6014 Approved
0.7391 Intermediate Similarity NPD6118 Approved
0.7391 Intermediate Similarity NPD6115 Approved
0.7391 Intermediate Similarity NPD6114 Approved
0.7391 Intermediate Similarity NPD6697 Approved
0.7379 Intermediate Similarity NPD4225 Approved
0.7364 Intermediate Similarity NPD6882 Approved
0.7347 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7632 Discontinued
0.7333 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD6409 Approved
0.732 Intermediate Similarity NPD6684 Approved
0.732 Intermediate Similarity NPD7521 Approved
0.732 Intermediate Similarity NPD5330 Approved
0.732 Intermediate Similarity NPD7334 Approved
0.732 Intermediate Similarity NPD7146 Approved
0.7315 Intermediate Similarity NPD6011 Approved
0.73 Intermediate Similarity NPD6079 Approved
0.7297 Intermediate Similarity NPD4632 Approved
0.7282 Intermediate Similarity NPD4755 Approved
0.7273 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD5695 Phase 3
0.7234 Intermediate Similarity NPD7525 Registered
0.7228 Intermediate Similarity NPD4202 Approved
0.7222 Intermediate Similarity NPD6412 Phase 2
0.7217 Intermediate Similarity NPD6319 Approved
0.7212 Intermediate Similarity NPD5696 Approved
0.7182 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD6672 Approved
0.7172 Intermediate Similarity NPD6903 Approved
0.7172 Intermediate Similarity NPD5737 Approved
0.7156 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5285 Approved
0.7143 Intermediate Similarity NPD4700 Approved
0.7143 Intermediate Similarity NPD5286 Approved
0.7143 Intermediate Similarity NPD4696 Approved
0.7143 Intermediate Similarity NPD8133 Approved
0.7129 Intermediate Similarity NPD6411 Approved
0.7113 Intermediate Similarity NPD3668 Phase 3
0.7113 Intermediate Similarity NPD3133 Approved
0.7113 Intermediate Similarity NPD3665 Phase 1
0.7113 Intermediate Similarity NPD3666 Approved
0.7111 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD4753 Phase 2
0.7087 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7736 Approved
0.7079 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7507 Approved
0.7034 Intermediate Similarity NPD8328 Phase 3
0.7019 Intermediate Similarity NPD4697 Phase 3
0.7019 Intermediate Similarity NPD5222 Approved
0.7019 Intermediate Similarity NPD5221 Approved
0.7019 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD6274 Approved
0.701 Intermediate Similarity NPD4788 Approved
0.7009 Intermediate Similarity NPD4633 Approved
0.7009 Intermediate Similarity NPD5226 Approved
0.7009 Intermediate Similarity NPD5225 Approved
0.7009 Intermediate Similarity NPD5224 Approved
0.7009 Intermediate Similarity NPD5211 Phase 2
0.7 Intermediate Similarity NPD8293 Discontinued
0.7 Intermediate Similarity NPD6686 Approved
0.6983 Remote Similarity NPD7101 Approved
0.6983 Remote Similarity NPD7100 Approved
0.6975 Remote Similarity NPD7492 Approved
0.6972 Remote Similarity NPD6008 Approved
0.697 Remote Similarity NPD6098 Approved
0.697 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6009 Approved
0.6952 Remote Similarity NPD5173 Approved
0.6947 Remote Similarity NPD7645 Phase 2
0.6944 Remote Similarity NPD5174 Approved
0.6944 Remote Similarity NPD5175 Approved
0.6931 Remote Similarity NPD6673 Approved
0.6931 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6931 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6931 Remote Similarity NPD6080 Approved
0.6931 Remote Similarity NPD6101 Approved
0.6931 Remote Similarity NPD6904 Approved
0.6923 Remote Similarity NPD5777 Approved
0.6923 Remote Similarity NPD6054 Approved
0.6923 Remote Similarity NPD6059 Approved
0.6917 Remote Similarity NPD6616 Approved
0.6916 Remote Similarity NPD5223 Approved
0.6909 Remote Similarity NPD5954 Clinical (unspecified phase)
0.69 Remote Similarity NPD3573 Approved
0.6897 Remote Similarity NPD6335 Approved
0.6891 Remote Similarity NPD7604 Phase 2
0.6889 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6885 Remote Similarity NPD7319 Approved
0.6882 Remote Similarity NPD3703 Phase 2
0.6881 Remote Similarity NPD5141 Approved
0.6875 Remote Similarity NPD4634 Approved
0.687 Remote Similarity NPD6868 Approved
0.6864 Remote Similarity NPD8033 Approved
0.6864 Remote Similarity NPD6909 Approved
0.6864 Remote Similarity NPD5983 Phase 2
0.6864 Remote Similarity NPD6908 Approved
0.686 Remote Similarity NPD7078 Approved
0.6842 Remote Similarity NPD3617 Approved
0.6818 Remote Similarity NPD4767 Approved
0.6818 Remote Similarity NPD4768 Approved
0.6813 Remote Similarity NPD4244 Approved
0.6813 Remote Similarity NPD4245 Approved
0.681 Remote Similarity NPD6317 Approved
0.6807 Remote Similarity NPD6370 Approved
0.6789 Remote Similarity NPD4754 Approved
0.678 Remote Similarity NPD8294 Approved
0.678 Remote Similarity NPD8377 Approved
0.6778 Remote Similarity NPD5360 Phase 3
0.6778 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6777 Remote Similarity NPD6336 Discontinued
0.6762 Remote Similarity NPD5210 Approved
0.6762 Remote Similarity NPD4629 Approved
0.6752 Remote Similarity NPD7327 Approved
0.6752 Remote Similarity NPD7328 Approved
0.6752 Remote Similarity NPD6313 Approved
0.6752 Remote Similarity NPD6314 Approved
0.6739 Remote Similarity NPD6081 Approved
0.6735 Remote Similarity NPD4221 Approved
0.6735 Remote Similarity NPD4223 Phase 3
0.6733 Remote Similarity NPD7524 Approved
0.6723 Remote Similarity NPD8379 Approved
0.6723 Remote Similarity NPD8296 Approved
0.6723 Remote Similarity NPD6015 Approved
0.6723 Remote Similarity NPD8378 Approved
0.6723 Remote Similarity NPD8380 Approved
0.6723 Remote Similarity NPD8335 Approved
0.6723 Remote Similarity NPD6016 Approved
0.6703 Remote Similarity NPD3698 Phase 2
0.6702 Remote Similarity NPD3702 Approved
0.6702 Remote Similarity NPD7339 Approved
0.6702 Remote Similarity NPD6942 Approved
0.67 Remote Similarity NPD5329 Approved
0.6696 Remote Similarity NPD4730 Approved
0.6696 Remote Similarity NPD4729 Approved
0.6696 Remote Similarity NPD5128 Approved
0.6695 Remote Similarity NPD7516 Approved
0.6667 Remote Similarity NPD5208 Approved
0.6667 Remote Similarity NPD5988 Approved
0.6667 Remote Similarity NPD6001 Approved
0.6667 Remote Similarity NPD7154 Phase 3
0.6635 Remote Similarity NPD7637 Suspended
0.6635 Remote Similarity NPD5693 Phase 1
0.6635 Remote Similarity NPD5284 Approved
0.6635 Remote Similarity NPD5281 Approved
0.6635 Remote Similarity NPD6050 Approved
0.6634 Remote Similarity NPD5279 Phase 3
0.6633 Remote Similarity NPD4139 Approved
0.6633 Remote Similarity NPD5369 Approved
0.6633 Remote Similarity NPD4692 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