Structure

Physi-Chem Properties

Molecular Weight:  954.52
Volume:  943.843
LogP:  4.059
LogD:  3.443
LogS:  -4.192
# Rotatable Bonds:  17
TPSA:  272.98
# H-Bond Aceptor:  18
# H-Bond Donor:  9
# Rings:  7
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.107
Synthetic Accessibility Score:  6.135
Fsp3:  0.857
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:  -6.175
MDCK Permeability:  0.00021601283515337855
Pgp-inhibitor:  0.716
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.758
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.936

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.026
Plasma Protein Binding (PPB):  57.29716491699219%
Volume Distribution (VD):  0.431
Pgp-substrate:  12.867437362670898%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.495
CYP2C19-inhibitor:  0.004
CYP2C19-substrate:  0.664
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.022
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.088
CYP3A4-inhibitor:  0.162
CYP3A4-substrate:  0.151

ADMET: Excretion

Clearance (CL):  3.736
Half-life (T1/2):  0.873

ADMET: Toxicity

hERG Blockers:  0.812
Human Hepatotoxicity (H-HT):  0.219
Drug-inuced Liver Injury (DILI):  0.042
AMES Toxicity:  0.073
Rat Oral Acute Toxicity:  0.027
Maximum Recommended Daily Dose:  0.093
Skin Sensitization:  0.944
Carcinogencity:  0.127
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.916

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

  Natural Product: NPC473205

Natural Product ID:  NPC473205
Common Name*:   (22S)-16Beta-[(Beta-D-Glucopyranosyl)Oxy]-3Beta,22-Dihydroxy-5Alphacholestan-1Beta-Yl 6-O-(3,4,5-Trimethoxybenzoyl)-Beta-D-Glucopyranoside
IUPAC Name:   [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1R,3R,5S,8S,9S,10S,13S,14S,16S,17R)-3-hydroxy-17-[(2S,3S)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-16-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]oxy]oxan-2-yl]methyl 3,4,5-trimethoxybenzoate
Synonyms:  
Standard InCHIKey:  CJAONFHPXWHKGS-AQRANOECSA-N
Standard InCHI:  InChI=1S/C49H78O18/c1-22(2)9-12-30(52)23(3)37-31(64-46-42(57)40(55)38(53)34(20-50)65-46)19-29-27-11-10-25-17-26(51)18-36(49(25,5)28(27)13-14-48(29,37)4)67-47-43(58)41(56)39(54)35(66-47)21-63-45(59)24-15-32(60-6)44(62-8)33(16-24)61-7/h15-16,22-23,25-31,34-43,46-47,50-58H,9-14,17-21H2,1-8H3/t23-,25+,26-,27-,28+,29+,30+,31+,34-,35-,36-,37+,38-,39-,40+,41+,42-,43-,46-,47+,48+,49+/m1/s1
SMILES:  OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3[C@]([C@H]2[C@@H]([C@H](CCC(C)C)O)C)(C)CC[C@H]2[C@H]3CC[C@@H]3[C@]2(C)[C@@H](C[C@@H](C3)O)O[C@@H]2O[C@H](COC(=O)c3cc(OC)c(c(c3)OC)OC)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL364824
PubChem CID:   11491537
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
NPO29813 Ornithogalum thyrsoides Species Hyacinthaceae Eukaryota bulbs n.a. n.a. PMID[12398536]
NPO29813 Ornithogalum thyrsoides Species Hyacinthaceae Eukaryota n.a. bulb n.a. PMID[12398536]
NPO29813 Ornithogalum thyrsoides Species Hyacinthaceae Eukaryota bulbs n.a. n.a. PMID[15497941]

☑ 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 5.0 ug.mL-1 PMID[450024]
NPT924 Cell Line HSC-2 Homo sapiens IC50 > 100.0 ug.mL-1 PMID[450024]

☑ 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 NPC473205 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 NPC473776
0.9483 High Similarity NPC71385
0.9483 High Similarity NPC230670
0.9429 High Similarity NPC112708
0.9375 High Similarity NPC473711
0.92 High Similarity NPC299855
0.92 High Similarity NPC96194
0.9148 High Similarity NPC189704
0.9096 High Similarity NPC476067
0.9096 High Similarity NPC475121
0.8944 High Similarity NPC475299
0.8908 High Similarity NPC469354
0.8902 High Similarity NPC470685
0.8851 High Similarity NPC195972
0.8791 High Similarity NPC476358
0.8786 High Similarity NPC266545
0.8786 High Similarity NPC202428
0.8779 High Similarity NPC306475
0.8779 High Similarity NPC200726
0.875 High Similarity NPC472723
0.8728 High Similarity NPC177362
0.8678 High Similarity NPC21956
0.8671 High Similarity NPC282551
0.8629 High Similarity NPC179240
0.8621 High Similarity NPC286809
0.8603 High Similarity NPC188217
0.8596 High Similarity NPC474936
0.8588 High Similarity NPC471878
0.858 High Similarity NPC469775
0.858 High Similarity NPC295941
0.858 High Similarity NPC38438
0.858 High Similarity NPC100925
0.858 High Similarity NPC469778
0.858 High Similarity NPC469774
0.858 High Similarity NPC469772
0.858 High Similarity NPC469773
0.858 High Similarity NPC469776
0.858 High Similarity NPC32723
0.858 High Similarity NPC135334
0.858 High Similarity NPC469777
0.8571 High Similarity NPC142291
0.8571 High Similarity NPC7839
0.8571 High Similarity NPC197708
0.8571 High Similarity NPC658
0.8555 High Similarity NPC100420
0.8547 High Similarity NPC80956
0.8547 High Similarity NPC100465
0.8547 High Similarity NPC266365
0.8547 High Similarity NPC195114
0.8547 High Similarity NPC152424
0.8539 High Similarity NPC79736
0.8539 High Similarity NPC67629
0.8539 High Similarity NPC297574
0.8514 High Similarity NPC185498
0.85 High Similarity NPC102367
0.8497 Intermediate Similarity NPC477491
0.8497 Intermediate Similarity NPC145847
0.8492 Intermediate Similarity NPC267549
0.8492 Intermediate Similarity NPC469418
0.8492 Intermediate Similarity NPC80360
0.8492 Intermediate Similarity NPC260300
0.8483 Intermediate Similarity NPC469438
0.8478 Intermediate Similarity NPC264302
0.8475 Intermediate Similarity NPC102851
0.8475 Intermediate Similarity NPC5786
0.847 Intermediate Similarity NPC173872
0.847 Intermediate Similarity NPC119094
0.8457 Intermediate Similarity NPC477488
0.8453 Intermediate Similarity NPC123259
0.8453 Intermediate Similarity NPC129533
0.8448 Intermediate Similarity NPC109990
0.8444 Intermediate Similarity NPC161609
0.8444 Intermediate Similarity NPC275690
0.8436 Intermediate Similarity NPC475613
0.8436 Intermediate Similarity NPC469397
0.843 Intermediate Similarity NPC179914
0.8427 Intermediate Similarity NPC316539
0.8427 Intermediate Similarity NPC166674
0.8427 Intermediate Similarity NPC219600
0.8427 Intermediate Similarity NPC473550
0.8427 Intermediate Similarity NPC46640
0.8427 Intermediate Similarity NPC473467
0.8427 Intermediate Similarity NPC263119
0.8427 Intermediate Similarity NPC475197
0.8427 Intermediate Similarity NPC34436
0.8424 Intermediate Similarity NPC469652
0.8424 Intermediate Similarity NPC472724
0.8424 Intermediate Similarity NPC160543
0.8424 Intermediate Similarity NPC93065
0.8424 Intermediate Similarity NPC31208
0.8424 Intermediate Similarity NPC472720
0.8424 Intermediate Similarity NPC472721
0.8418 Intermediate Similarity NPC470272
0.8418 Intermediate Similarity NPC52598
0.8418 Intermediate Similarity NPC472803
0.8409 Intermediate Similarity NPC311389
0.8409 Intermediate Similarity NPC470271
0.8402 Intermediate Similarity NPC228662
0.84 Intermediate Similarity NPC475738
0.84 Intermediate Similarity NPC222531
0.8398 Intermediate Similarity NPC53680
0.8398 Intermediate Similarity NPC208797
0.8391 Intermediate Similarity NPC476011
0.8391 Intermediate Similarity NPC206815
0.8391 Intermediate Similarity NPC148273
0.8391 Intermediate Similarity NPC41009
0.8382 Intermediate Similarity NPC24627
0.838 Intermediate Similarity NPC146803
0.8372 Intermediate Similarity NPC472860
0.8371 Intermediate Similarity NPC477617
0.8371 Intermediate Similarity NPC100251
0.8371 Intermediate Similarity NPC148185
0.8371 Intermediate Similarity NPC65333
0.837 Intermediate Similarity NPC269046
0.837 Intermediate Similarity NPC240200
0.837 Intermediate Similarity NPC290289
0.837 Intermediate Similarity NPC223534
0.837 Intermediate Similarity NPC158214
0.8363 Intermediate Similarity NPC476784
0.8362 Intermediate Similarity NPC61791
0.8362 Intermediate Similarity NPC149300
0.8361 Intermediate Similarity NPC229817
0.8361 Intermediate Similarity NPC473686
0.8361 Intermediate Similarity NPC221140
0.8361 Intermediate Similarity NPC111490
0.8361 Intermediate Similarity NPC475220
0.8361 Intermediate Similarity NPC261623
0.8361 Intermediate Similarity NPC475352
0.8352 Intermediate Similarity NPC175793
0.8352 Intermediate Similarity NPC473883
0.8343 Intermediate Similarity NPC472726
0.8343 Intermediate Similarity NPC120012
0.8343 Intermediate Similarity NPC472725
0.8343 Intermediate Similarity NPC198902
0.8343 Intermediate Similarity NPC14294
0.8343 Intermediate Similarity NPC116759
0.8333 Intermediate Similarity NPC475054
0.8333 Intermediate Similarity NPC115624
0.8333 Intermediate Similarity NPC473713
0.8324 Intermediate Similarity NPC201814
0.8324 Intermediate Similarity NPC98583
0.8324 Intermediate Similarity NPC187632
0.8324 Intermediate Similarity NPC124828
0.8324 Intermediate Similarity NPC163165
0.8315 Intermediate Similarity NPC260521
0.8315 Intermediate Similarity NPC52353
0.8315 Intermediate Similarity NPC65489
0.8315 Intermediate Similarity NPC237202
0.8315 Intermediate Similarity NPC469649
0.8315 Intermediate Similarity NPC181778
0.8315 Intermediate Similarity NPC105591
0.8306 Intermediate Similarity NPC114120
0.8306 Intermediate Similarity NPC231254
0.8306 Intermediate Similarity NPC167045
0.8305 Intermediate Similarity NPC190204
0.8305 Intermediate Similarity NPC43918
0.8305 Intermediate Similarity NPC261411
0.8297 Intermediate Similarity NPC170203
0.8297 Intermediate Similarity NPC477860
0.8297 Intermediate Similarity NPC8940
0.8297 Intermediate Similarity NPC469371
0.8297 Intermediate Similarity NPC475161
0.8295 Intermediate Similarity NPC15358
0.8287 Intermediate Similarity NPC475261
0.8287 Intermediate Similarity NPC472387
0.8287 Intermediate Similarity NPC477882
0.8287 Intermediate Similarity NPC477880
0.8286 Intermediate Similarity NPC33298
0.8286 Intermediate Similarity NPC285108
0.8286 Intermediate Similarity NPC14030
0.8286 Intermediate Similarity NPC291957
0.8286 Intermediate Similarity NPC473468
0.8286 Intermediate Similarity NPC475567
0.8286 Intermediate Similarity NPC473557
0.828 Intermediate Similarity NPC471091
0.828 Intermediate Similarity NPC97924
0.828 Intermediate Similarity NPC40078
0.8278 Intermediate Similarity NPC475244
0.8276 Intermediate Similarity NPC239966
0.8276 Intermediate Similarity NPC203020
0.827 Intermediate Similarity NPC477081
0.827 Intermediate Similarity NPC477083
0.8268 Intermediate Similarity NPC475155
0.8266 Intermediate Similarity NPC4747
0.8266 Intermediate Similarity NPC187205
0.8266 Intermediate Similarity NPC238419
0.8266 Intermediate Similarity NPC172419
0.8266 Intermediate Similarity NPC1913
0.8266 Intermediate Similarity NPC104275
0.8261 Intermediate Similarity NPC87583
0.8261 Intermediate Similarity NPC469650
0.8258 Intermediate Similarity NPC95421
0.8258 Intermediate Similarity NPC198125
0.8256 Intermediate Similarity NPC156624
0.8256 Intermediate Similarity NPC172920
0.8251 Intermediate Similarity NPC473631
0.8251 Intermediate Similarity NPC293227
0.8251 Intermediate Similarity NPC35924
0.8251 Intermediate Similarity NPC132111
0.8251 Intermediate Similarity NPC473717

  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 NPC473205 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
0.8514 High Similarity NPD7228 Approved
0.8427 Intermediate Similarity NPD7685 Pre-registration
0.8427 Intermediate Similarity NPD7240 Approved
0.8246 Intermediate Similarity NPD37 Approved
0.8242 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8208 Intermediate Similarity NPD4966 Approved
0.8208 Intermediate Similarity NPD4965 Approved
0.8208 Intermediate Similarity NPD4967 Phase 2
0.8125 Intermediate Similarity NPD7199 Phase 2
0.8125 Intermediate Similarity NPD8127 Discontinued
0.8114 Intermediate Similarity NPD6234 Discontinued
0.8111 Intermediate Similarity NPD7074 Phase 3
0.8111 Intermediate Similarity NPD7472 Approved
0.8077 Intermediate Similarity NPD7808 Phase 3
0.8066 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8056 Intermediate Similarity NPD7054 Approved
0.8 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7956 Intermediate Similarity NPD5844 Phase 1
0.7935 Intermediate Similarity NPD8313 Approved
0.7935 Intermediate Similarity NPD8312 Approved
0.7933 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7926 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7923 Intermediate Similarity NPD7251 Discontinued
0.7901 Intermediate Similarity NPD3818 Discontinued
0.7869 Intermediate Similarity NPD6797 Phase 2
0.7868 Intermediate Similarity NPD8151 Discontinued
0.7849 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD8455 Phase 2
0.7784 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7747 Intermediate Similarity NPD7473 Discontinued
0.7725 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6166 Phase 2
0.7692 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD6273 Approved
0.7684 Intermediate Similarity NPD1465 Phase 2
0.768 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD6232 Discontinued
0.7667 Intermediate Similarity NPD5494 Approved
0.7657 Intermediate Similarity NPD7458 Discontinued
0.7654 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD7680 Approved
0.7584 Intermediate Similarity NPD7819 Suspended
0.754 Intermediate Similarity NPD6559 Discontinued
0.7525 Intermediate Similarity NPD7497 Discontinued
0.7514 Intermediate Similarity NPD7799 Discontinued
0.7514 Intermediate Similarity NPD7028 Phase 2
0.7471 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD3817 Phase 2
0.7437 Intermediate Similarity NPD7435 Discontinued
0.7435 Intermediate Similarity NPD8434 Phase 2
0.7432 Intermediate Similarity NPD6959 Discontinued
0.743 Intermediate Similarity NPD1934 Approved
0.7416 Intermediate Similarity NPD4380 Phase 2
0.7399 Intermediate Similarity NPD4628 Phase 3
0.7389 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD7075 Discontinued
0.735 Intermediate Similarity NPD7697 Approved
0.735 Intermediate Similarity NPD7696 Phase 3
0.735 Intermediate Similarity NPD7698 Approved
0.7341 Intermediate Similarity NPD6674 Discontinued
0.733 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7266 Discontinued
0.7313 Intermediate Similarity NPD8319 Approved
0.7313 Intermediate Similarity NPD8320 Phase 1
0.7304 Intermediate Similarity NPD7874 Approved
0.7304 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD1653 Approved
0.7299 Intermediate Similarity NPD8166 Discontinued
0.7293 Intermediate Similarity NPD5760 Phase 2
0.7293 Intermediate Similarity NPD5761 Phase 2
0.7291 Intermediate Similarity NPD7701 Phase 2
0.7286 Intermediate Similarity NPD6779 Approved
0.7286 Intermediate Similarity NPD6780 Approved
0.7286 Intermediate Similarity NPD6778 Approved
0.7286 Intermediate Similarity NPD6776 Approved
0.7286 Intermediate Similarity NPD6777 Approved
0.7286 Intermediate Similarity NPD6781 Approved
0.7286 Intermediate Similarity NPD6782 Approved
0.7268 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD7783 Phase 2
0.7253 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD5353 Approved
0.724 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD230 Phase 1
0.7232 Intermediate Similarity NPD2532 Approved
0.7232 Intermediate Similarity NPD2534 Approved
0.7232 Intermediate Similarity NPD2533 Approved
0.7228 Intermediate Similarity NPD7870 Phase 2
0.7228 Intermediate Similarity NPD7871 Phase 2
0.7222 Intermediate Similarity NPD6599 Discontinued
0.7219 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD7236 Approved
0.7213 Intermediate Similarity NPD3882 Suspended
0.7204 Intermediate Similarity NPD3787 Discontinued
0.72 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD2801 Approved
0.7186 Intermediate Similarity NPD7700 Phase 2
0.7186 Intermediate Similarity NPD7699 Phase 2
0.7184 Intermediate Similarity NPD7801 Approved
0.7182 Intermediate Similarity NPD7411 Suspended
0.7165 Intermediate Similarity NPD8150 Discontinued
0.7143 Intermediate Similarity NPD3751 Discontinued
0.7143 Intermediate Similarity NPD6801 Discontinued
0.7129 Intermediate Similarity NPD6823 Phase 2
0.712 Intermediate Similarity NPD7768 Phase 2
0.7111 Intermediate Similarity NPD7239 Suspended
0.7086 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD3620 Phase 2
0.7076 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD5402 Approved
0.7062 Intermediate Similarity NPD6190 Approved
0.7052 Intermediate Similarity NPD7097 Phase 1
0.7035 Intermediate Similarity NPD6534 Approved
0.7035 Intermediate Similarity NPD6535 Approved
0.7029 Intermediate Similarity NPD5763 Approved
0.7029 Intermediate Similarity NPD5762 Approved
0.7016 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD4110 Phase 3
0.7006 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7003 Approved
0.6995 Remote Similarity NPD6765 Approved
0.6995 Remote Similarity NPD6764 Approved
0.6984 Remote Similarity NPD5242 Approved
0.6983 Remote Similarity NPD6799 Approved
0.6978 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6977 Remote Similarity NPD4140 Approved
0.6977 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6971 Remote Similarity NPD6099 Approved
0.6971 Remote Similarity NPD6100 Approved
0.6963 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6942 Remote Similarity NPD7999 Approved
0.6931 Remote Similarity NPD7229 Phase 3
0.6919 Remote Similarity NPD7930 Approved
0.691 Remote Similarity NPD3750 Approved
0.6907 Remote Similarity NPD8368 Discontinued
0.6898 Remote Similarity NPD3749 Approved
0.6889 Remote Similarity NPD1511 Approved
0.6888 Remote Similarity NPD8407 Phase 2
0.6868 Remote Similarity NPD5403 Approved
0.6862 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6862 Remote Similarity NPD919 Approved
0.686 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6854 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6853 Remote Similarity NPD6785 Approved
0.6853 Remote Similarity NPD6784 Approved
0.6851 Remote Similarity NPD5401 Approved
0.6842 Remote Similarity NPD5710 Approved
0.6842 Remote Similarity NPD5711 Approved
0.6839 Remote Similarity NPD5735 Approved
0.6827 Remote Similarity NPD7583 Approved
0.6821 Remote Similarity NPD8032 Phase 2
0.6821 Remote Similarity NPD6663 Approved
0.6818 Remote Similarity NPD3748 Approved
0.6816 Remote Similarity NPD6213 Phase 3
0.6816 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6816 Remote Similarity NPD6212 Phase 3
0.6816 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6813 Remote Similarity NPD1512 Approved
0.6811 Remote Similarity NPD6386 Approved
0.6811 Remote Similarity NPD6385 Approved
0.6806 Remote Similarity NPD3926 Phase 2
0.6802 Remote Similarity NPD3027 Phase 3
0.6798 Remote Similarity NPD1549 Phase 2
0.6794 Remote Similarity NPD7585 Approved
0.6793 Remote Similarity NPD3226 Approved
0.6784 Remote Similarity NPD5736 Approved
0.678 Remote Similarity NPD2796 Approved
0.6758 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6758 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6755 Remote Similarity NPD7057 Phase 3
0.6755 Remote Similarity NPD7058 Phase 2
0.6743 Remote Similarity NPD1933 Approved
0.6743 Remote Similarity NPD6355 Discontinued
0.6742 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6742 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6727 Remote Similarity NPD8059 Phase 3
0.6727 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6723 Remote Similarity NPD1510 Phase 2
0.6715 Remote Similarity NPD5006 Approved
0.6715 Remote Similarity NPD5005 Approved
0.6705 Remote Similarity NPD6653 Approved
0.6703 Remote Similarity NPD7390 Discontinued
0.6702 Remote Similarity NPD1247 Approved
0.67 Remote Similarity NPD6841 Approved
0.67 Remote Similarity NPD6843 Phase 3
0.67 Remote Similarity NPD6842 Approved
0.6698 Remote Similarity NPD8404 Phase 2
0.6686 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6686 Remote Similarity NPD1613 Approved
0.6685 Remote Similarity NPD2935 Discontinued
0.6667 Remote Similarity NPD8361 Approved
0.6667 Remote Similarity NPD7584 Approved
0.6667 Remote Similarity NPD8360 Approved
0.6667 Remote Similarity NPD8435 Approved
0.6667 Remote Similarity NPD2800 Approved
0.6667 Remote Similarity NPD7422 Clinical (unspecified phase)
0.665 Remote Similarity NPD8424 Clinical (unspecified phase)

  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