Structure

Physi-Chem Properties

Molecular Weight:  1064.52
Volume:  1040.228
LogP:  3.303
LogD:  2.443
LogS:  -4.152
# Rotatable Bonds:  19
TPSA:  305.35
# H-Bond Aceptor:  21
# H-Bond Donor:  8
# Rings:  8
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.082
Synthetic Accessibility Score:  6.489
Fsp3:  0.796
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:  -5.695
MDCK Permeability:  0.0002042547130258754
Pgp-inhibitor:  0.999
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.898
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.124
Plasma Protein Binding (PPB):  80.13201141357422%
Volume Distribution (VD):  0.463
Pgp-substrate:  13.797445297241211%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.515
CYP2C19-inhibitor:  0.002
CYP2C19-substrate:  0.195
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.005
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.052
CYP3A4-inhibitor:  0.276
CYP3A4-substrate:  0.086

ADMET: Excretion

Clearance (CL):  1.159
Half-life (T1/2):  0.873

ADMET: Toxicity

hERG Blockers:  0.698
Human Hepatotoxicity (H-HT):  0.216
Drug-inuced Liver Injury (DILI):  0.263
AMES Toxicity:  0.071
Rat Oral Acute Toxicity:  0.086
Maximum Recommended Daily Dose:  0.288
Skin Sensitization:  0.139
Carcinogencity:  0.327
Eye Corrosion:  0.003
Eye Irritation:  0.006
Respiratory Toxicity:  0.837

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

  Natural Product: NPC96194

Natural Product ID:  NPC96194
Common Name*:   3Beta,17Alpha-Dihydroxy-16Beta-[(O-Beta-D-Glucopyranosyl-(1->4)-O-(2-O-3,4-Dimethoxybenzoyl-Beta-D-Xylopyranosyl)-(1->3)-2-O-Acetyl-Alpha-L-Arabinopyranosyl)Oxy]Cholest-5-En-22-One
IUPAC Name:   [(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-3,17-dihydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] 3,4-dimethoxybenzoate
Synonyms:  
Standard InCHIKey:  HNJIRKJOLJDINX-HHBUYJSASA-N
Standard InCHI:  InChI=1S/C54H80O21/c1-25(2)9-13-34(58)26(3)54(65)40(21-33-31-12-11-29-20-30(57)15-17-52(29,5)32(31)16-18-53(33,54)6)73-51-47(70-27(4)56)45(35(59)23-68-51)75-50-46(74-48(64)28-10-14-36(66-7)37(19-28)67-8)42(61)39(24-69-50)72-49-44(63)43(62)41(60)38(22-55)71-49/h10-11,14,19,25-26,30-33,35,38-47,49-51,55,57,59-63,65H,9,12-13,15-18,20-24H2,1-8H3/t26-,30+,31-,32+,33+,35+,38-,39-,40+,41-,42+,43+,44-,45+,46-,47-,49+,50+,51+,52+,53+,54-/m1/s1
SMILES:  CC(C)CCC(=O)[C@@H](C)[C@]1([C@H](C[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)OC(=O)c1ccc(c(c1)OC)OC)OC(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL452643
PubChem CID:   10677624
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
NPO28180 Ornithogalum saundersiae Species Hyacinthaceae Eukaryota n.a. bulb n.a. DOI[10.1016/S0960-894X(97)00071-1]
NPO28180 Ornithogalum saundersiae Species Hyacinthaceae Eukaryota bulbs n.a. n.a. PMID[11170674]
NPO28180 Ornithogalum saundersiae Species Hyacinthaceae Eukaryota n.a. bulb n.a. PMID[7586067]
NPO28180 Ornithogalum saundersiae Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28180 Ornithogalum saundersiae Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28180 Ornithogalum saundersiae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 16.0 nM PMID[481381]

☑ 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 NPC96194 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 NPC299855
0.9941 High Similarity NPC189704
0.9883 High Similarity NPC475121
0.9883 High Similarity NPC476067
0.9713 High Similarity NPC475299
0.9711 High Similarity NPC71385
0.9711 High Similarity NPC230670
0.9655 High Similarity NPC112708
0.96 High Similarity NPC473711
0.9527 High Similarity NPC195972
0.92 High Similarity NPC473776
0.92 High Similarity NPC473205
0.8793 High Similarity NPC21956
0.8786 High Similarity NPC282551
0.8713 High Similarity NPC474936
0.8671 High Similarity NPC100420
0.8652 High Similarity NPC475613
0.8613 High Similarity NPC206815
0.8596 High Similarity NPC475244
0.8588 High Similarity NPC470685
0.8588 High Similarity NPC135334
0.8588 High Similarity NPC469776
0.8588 High Similarity NPC469778
0.8588 High Similarity NPC295941
0.8588 High Similarity NPC469774
0.8588 High Similarity NPC469773
0.8588 High Similarity NPC469777
0.8588 High Similarity NPC469772
0.8588 High Similarity NPC100925
0.8588 High Similarity NPC32723
0.8588 High Similarity NPC469775
0.858 High Similarity NPC266545
0.858 High Similarity NPC202428
0.8571 High Similarity NPC200726
0.8563 High Similarity NPC109990
0.8539 High Similarity NPC473467
0.8539 High Similarity NPC124828
0.8539 High Similarity NPC475197
0.8531 High Similarity NPC472803
0.8523 High Similarity NPC177362
0.8523 High Similarity NPC286809
0.8514 High Similarity NPC318472
0.8508 High Similarity NPC188217
0.8506 High Similarity NPC145847
0.8506 High Similarity NPC476011
0.8492 Intermediate Similarity NPC469354
0.848 Intermediate Similarity NPC476784
0.8466 Intermediate Similarity NPC301910
0.8466 Intermediate Similarity NPC477488
0.8466 Intermediate Similarity NPC130730
0.8466 Intermediate Similarity NPC469419
0.8457 Intermediate Similarity NPC327694
0.8439 Intermediate Similarity NPC179914
0.8421 Intermediate Similarity NPC476364
0.8409 Intermediate Similarity NPC102465
0.84 Intermediate Similarity NPC326278
0.84 Intermediate Similarity NPC477491
0.8398 Intermediate Similarity NPC469418
0.8389 Intermediate Similarity NPC469438
0.8382 Intermediate Similarity NPC471878
0.8361 Intermediate Similarity NPC473883
0.8361 Intermediate Similarity NPC186746
0.8353 Intermediate Similarity NPC475379
0.8343 Intermediate Similarity NPC469397
0.8343 Intermediate Similarity NPC477627
0.8343 Intermediate Similarity NPC475054
0.8333 Intermediate Similarity NPC471871
0.8333 Intermediate Similarity NPC316539
0.8324 Intermediate Similarity NPC52598
0.8305 Intermediate Similarity NPC180586
0.8295 Intermediate Similarity NPC473468
0.8295 Intermediate Similarity NPC475567
0.8295 Intermediate Similarity NPC473557
0.8295 Intermediate Similarity NPC246024
0.8286 Intermediate Similarity NPC130489
0.8286 Intermediate Similarity NPC208676
0.8286 Intermediate Similarity NPC476337
0.8278 Intermediate Similarity NPC477617
0.8278 Intermediate Similarity NPC13989
0.8278 Intermediate Similarity NPC148185
0.8276 Intermediate Similarity NPC226759
0.8276 Intermediate Similarity NPC187205
0.8276 Intermediate Similarity NPC268602
0.8268 Intermediate Similarity NPC61791
0.8268 Intermediate Similarity NPC471870
0.8266 Intermediate Similarity NPC475484
0.8256 Intermediate Similarity NPC137813
0.8251 Intermediate Similarity NPC108191
0.8251 Intermediate Similarity NPC161609
0.8251 Intermediate Similarity NPC93685
0.8251 Intermediate Similarity NPC275690
0.8249 Intermediate Similarity NPC475531
0.8249 Intermediate Similarity NPC120012
0.8249 Intermediate Similarity NPC475175
0.8249 Intermediate Similarity NPC161151
0.8249 Intermediate Similarity NPC475198
0.8232 Intermediate Similarity NPC199357
0.8229 Intermediate Similarity NPC68619
0.8225 Intermediate Similarity NPC476338
0.8225 Intermediate Similarity NPC476359
0.8222 Intermediate Similarity NPC472129
0.8222 Intermediate Similarity NPC43434
0.8216 Intermediate Similarity NPC167045
0.8216 Intermediate Similarity NPC114120
0.8212 Intermediate Similarity NPC471860
0.8212 Intermediate Similarity NPC471859
0.8208 Intermediate Similarity NPC478232
0.8207 Intermediate Similarity NPC469371
0.8202 Intermediate Similarity NPC475738
0.8197 Intermediate Similarity NPC475261
0.8191 Intermediate Similarity NPC264302
0.8187 Intermediate Similarity NPC294149
0.8182 Intermediate Similarity NPC329960
0.8182 Intermediate Similarity NPC295408
0.8182 Intermediate Similarity NPC150893
0.8182 Intermediate Similarity NPC138993
0.8167 Intermediate Similarity NPC197708
0.8167 Intermediate Similarity NPC658
0.8167 Intermediate Similarity NPC472133
0.8162 Intermediate Similarity NPC35924
0.8162 Intermediate Similarity NPC199172
0.8161 Intermediate Similarity NPC131532
0.8161 Intermediate Similarity NPC10205
0.8156 Intermediate Similarity NPC306475
0.8156 Intermediate Similarity NPC476277
0.8152 Intermediate Similarity NPC195114
0.8152 Intermediate Similarity NPC473895
0.8152 Intermediate Similarity NPC254588
0.815 Intermediate Similarity NPC87403
0.8146 Intermediate Similarity NPC100425
0.814 Intermediate Similarity NPC289021
0.814 Intermediate Similarity NPC158546
0.8132 Intermediate Similarity NPC477881
0.8128 Intermediate Similarity NPC286301
0.8128 Intermediate Similarity NPC313063
0.8125 Intermediate Similarity NPC475536
0.8125 Intermediate Similarity NPC165234
0.8125 Intermediate Similarity NPC469384
0.8125 Intermediate Similarity NPC131405
0.8122 Intermediate Similarity NPC52353
0.8122 Intermediate Similarity NPC293004
0.8122 Intermediate Similarity NPC194483
0.8114 Intermediate Similarity NPC10945
0.8114 Intermediate Similarity NPC478248
0.8114 Intermediate Similarity NPC471405
0.8111 Intermediate Similarity NPC298847
0.8108 Intermediate Similarity NPC102367
0.8108 Intermediate Similarity NPC477860
0.8108 Intermediate Similarity NPC475161
0.8108 Intermediate Similarity NPC170203
0.8105 Intermediate Similarity NPC476358
0.8103 Intermediate Similarity NPC469417
0.8101 Intermediate Similarity NPC469420
0.8101 Intermediate Similarity NPC472130
0.8101 Intermediate Similarity NPC99216
0.8101 Intermediate Similarity NPC472131
0.8098 Intermediate Similarity NPC472387
0.8098 Intermediate Similarity NPC120952
0.8098 Intermediate Similarity NPC477882
0.8098 Intermediate Similarity NPC477880
0.8098 Intermediate Similarity NPC267549
0.8098 Intermediate Similarity NPC80360
0.8098 Intermediate Similarity NPC260300
0.8092 Intermediate Similarity NPC36130
0.8092 Intermediate Similarity NPC469456
0.8092 Intermediate Similarity NPC134905
0.8092 Intermediate Similarity NPC476335
0.809 Intermediate Similarity NPC41009
0.809 Intermediate Similarity NPC148273
0.809 Intermediate Similarity NPC471873
0.8087 Intermediate Similarity NPC146803
0.8087 Intermediate Similarity NPC102028
0.8087 Intermediate Similarity NPC473630
0.8085 Intermediate Similarity NPC205721
0.8081 Intermediate Similarity NPC147224
0.8079 Intermediate Similarity NPC269668
0.8079 Intermediate Similarity NPC473797
0.8079 Intermediate Similarity NPC239818
0.8079 Intermediate Similarity NPC475464
0.8079 Intermediate Similarity NPC475437
0.8079 Intermediate Similarity NPC473641
0.8079 Intermediate Similarity NPC475300
0.8079 Intermediate Similarity NPC475505
0.8079 Intermediate Similarity NPC478265
0.8079 Intermediate Similarity NPC218471
0.8077 Intermediate Similarity NPC475155
0.8077 Intermediate Similarity NPC102851
0.8077 Intermediate Similarity NPC472638
0.8077 Intermediate Similarity NPC472639
0.8077 Intermediate Similarity NPC38438
0.8077 Intermediate Similarity NPC5786
0.8077 Intermediate Similarity NPC472620
0.8075 Intermediate Similarity NPC473554
0.8075 Intermediate Similarity NPC470719
0.8075 Intermediate Similarity NPC295625
0.807 Intermediate Similarity NPC308178
0.8068 Intermediate Similarity NPC133984
0.8068 Intermediate Similarity NPC286919
0.8068 Intermediate Similarity NPC475663
0.8066 Intermediate Similarity NPC293629

  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 NPC96194 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
0.8644 High Similarity NPD7685 Pre-registration
0.8251 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8043 Intermediate Similarity NPD8312 Approved
0.8043 Intermediate Similarity NPD8313 Approved
0.8022 Intermediate Similarity NPD7074 Phase 3
0.8011 Intermediate Similarity NPD7799 Discontinued
0.7937 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD8127 Discontinued
0.7926 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7923 Intermediate Similarity NPD7472 Approved
0.7912 Intermediate Similarity NPD7228 Approved
0.7892 Intermediate Similarity NPD7808 Phase 3
0.7869 Intermediate Similarity NPD7054 Approved
0.7838 Intermediate Similarity NPD7240 Approved
0.7829 Intermediate Similarity NPD7028 Phase 2
0.7742 Intermediate Similarity NPD7251 Discontinued
0.7725 Intermediate Similarity NPD8434 Phase 2
0.7717 Intermediate Similarity NPD3818 Discontinued
0.7688 Intermediate Similarity NPD6797 Phase 2
0.764 Intermediate Similarity NPD37 Approved
0.7637 Intermediate Similarity NPD7199 Phase 2
0.7611 Intermediate Similarity NPD4967 Phase 2
0.7611 Intermediate Similarity NPD4965 Approved
0.7611 Intermediate Similarity NPD4966 Approved
0.7606 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD6273 Approved
0.7598 Intermediate Similarity NPD8455 Phase 2
0.7581 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD7458 Discontinued
0.7568 Intermediate Similarity NPD7473 Discontinued
0.7557 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD6234 Discontinued
0.7525 Intermediate Similarity NPD8151 Discontinued
0.7514 Intermediate Similarity NPD6166 Phase 2
0.7514 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD5844 Phase 1
0.7486 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD5494 Approved
0.7473 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD7497 Discontinued
0.745 Intermediate Similarity NPD7435 Discontinued
0.7448 Intermediate Similarity NPD8150 Discontinued
0.7429 Intermediate Similarity NPD7236 Approved
0.7418 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD8166 Discontinued
0.7414 Intermediate Similarity NPD4628 Phase 3
0.7413 Intermediate Similarity NPD8320 Phase 1
0.7413 Intermediate Similarity NPD8319 Approved
0.7405 Intermediate Similarity NPD6232 Discontinued
0.7403 Intermediate Similarity NPD5760 Phase 2
0.7403 Intermediate Similarity NPD5761 Phase 2
0.7403 Intermediate Similarity NPD7819 Suspended
0.7368 Intermediate Similarity NPD6559 Discontinued
0.7366 Intermediate Similarity NPD7783 Phase 2
0.7366 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD7698 Approved
0.7363 Intermediate Similarity NPD7696 Phase 3
0.7363 Intermediate Similarity NPD7697 Approved
0.7341 Intermediate Similarity NPD7266 Discontinued
0.7318 Intermediate Similarity NPD7239 Suspended
0.7317 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD7874 Approved
0.7304 Intermediate Similarity NPD7701 Phase 2
0.73 Intermediate Similarity NPD6781 Approved
0.73 Intermediate Similarity NPD6776 Approved
0.73 Intermediate Similarity NPD6780 Approved
0.73 Intermediate Similarity NPD6778 Approved
0.73 Intermediate Similarity NPD6779 Approved
0.73 Intermediate Similarity NPD6782 Approved
0.73 Intermediate Similarity NPD6777 Approved
0.7268 Intermediate Similarity NPD3817 Phase 2
0.7253 Intermediate Similarity NPD1934 Approved
0.7249 Intermediate Similarity NPD3751 Discontinued
0.7241 Intermediate Similarity NPD7870 Phase 2
0.7241 Intermediate Similarity NPD7871 Phase 2
0.7238 Intermediate Similarity NPD4380 Phase 2
0.723 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7699 Phase 2
0.72 Intermediate Similarity NPD7700 Phase 2
0.7198 Intermediate Similarity NPD7801 Approved
0.7192 Intermediate Similarity NPD7680 Approved
0.7189 Intermediate Similarity NPD7075 Discontinued
0.7188 Intermediate Similarity NPD8368 Discontinued
0.7188 Intermediate Similarity NPD6764 Approved
0.7188 Intermediate Similarity NPD6765 Approved
0.7165 Intermediate Similarity NPD8407 Phase 2
0.7164 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD6674 Discontinued
0.7151 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6823 Phase 2
0.7128 Intermediate Similarity NPD3787 Discontinued
0.712 Intermediate Similarity NPD1465 Phase 2
0.7081 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD6190 Approved
0.7074 Intermediate Similarity NPD6959 Discontinued
0.705 Intermediate Similarity NPD6534 Approved
0.705 Intermediate Similarity NPD6535 Approved
0.7049 Intermediate Similarity NPD6599 Discontinued
0.7043 Intermediate Similarity NPD3882 Suspended
0.7041 Intermediate Similarity NPD6785 Approved
0.7041 Intermediate Similarity NPD6784 Approved
0.7039 Intermediate Similarity NPD7999 Approved
0.7031 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD2801 Approved
0.7022 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD4110 Phase 3
0.7014 Intermediate Similarity NPD7930 Approved
0.7011 Intermediate Similarity NPD7411 Suspended
0.6995 Remote Similarity NPD3226 Approved
0.6994 Remote Similarity NPD3620 Phase 2
0.6994 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6994 Remote Similarity NPD4140 Approved
0.6977 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6973 Remote Similarity NPD6801 Discontinued
0.6971 Remote Similarity NPD7097 Phase 1
0.6968 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6963 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6954 Remote Similarity NPD5735 Approved
0.6952 Remote Similarity NPD7058 Phase 2
0.6952 Remote Similarity NPD7057 Phase 3
0.6949 Remote Similarity NPD5762 Approved
0.6949 Remote Similarity NPD5763 Approved
0.6948 Remote Similarity NPD8404 Phase 2
0.6936 Remote Similarity NPD8032 Phase 2
0.6935 Remote Similarity NPD8435 Approved
0.6935 Remote Similarity NPD8360 Approved
0.6935 Remote Similarity NPD8361 Approved
0.6898 Remote Similarity NPD5402 Approved
0.6872 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6868 Remote Similarity NPD2533 Approved
0.6868 Remote Similarity NPD2534 Approved
0.6868 Remote Similarity NPD2532 Approved
0.6854 Remote Similarity NPD2346 Discontinued
0.6848 Remote Similarity NPD1653 Approved
0.6839 Remote Similarity NPD6663 Approved
0.6834 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6833 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6833 Remote Similarity NPD7003 Approved
0.6832 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6832 Remote Similarity NPD6213 Phase 3
0.6832 Remote Similarity NPD6212 Phase 3
0.6828 Remote Similarity NPD6386 Approved
0.6828 Remote Similarity NPD6385 Approved
0.6825 Remote Similarity NPD3749 Approved
0.6818 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6799 Approved
0.6811 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6809 Remote Similarity NPD5353 Approved
0.6802 Remote Similarity NPD5736 Approved
0.68 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6796 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6772 Remote Similarity NPD7768 Phase 2
0.6761 Remote Similarity NPD230 Phase 1
0.6761 Remote Similarity NPD1933 Approved
0.6744 Remote Similarity NPD5647 Approved
0.6742 Remote Similarity NPD2799 Discontinued
0.6742 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6742 Remote Similarity NPD8059 Phase 3
0.6723 Remote Similarity NPD6653 Approved
0.6722 Remote Similarity NPD970 Clinical (unspecified phase)
0.6721 Remote Similarity NPD1511 Approved
0.672 Remote Similarity NPD5977 Approved
0.672 Remote Similarity NPD5978 Approved
0.6704 Remote Similarity NPD2935 Discontinued
0.6703 Remote Similarity NPD5403 Approved
0.6702 Remote Similarity NPD919 Approved
0.67 Remote Similarity NPD7296 Approved
0.6686 Remote Similarity NPD3764 Approved
0.6685 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6685 Remote Similarity NPD5401 Approved
0.6667 Remote Similarity NPD6355 Discontinued
0.6667 Remote Similarity NPD7907 Approved
0.6667 Remote Similarity NPD8285 Discontinued
0.6667 Remote Similarity NPD447 Suspended
0.665 Remote Similarity NPD8485 Approved
0.6649 Remote Similarity NPD1512 Approved
0.6649 Remote Similarity NPD5242 Approved
0.6649 Remote Similarity NPD3926 Phase 2
0.6648 Remote Similarity NPD7033 Discontinued
0.6648 Remote Similarity NPD3750 Approved
0.6648 Remote Similarity NPD1878 Clinical (unspecified phase)
0.663 Remote Similarity NPD1549 Phase 2
0.6629 Remote Similarity NPD7095 Approved
0.6629 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6629 Remote Similarity NPD6353 Approved
0.6618 Remote Similarity NPD4420 Approved
0.6611 Remote Similarity NPD2438 Suspended
0.6611 Remote Similarity NPD2796 Approved
0.6611 Remote Similarity NPD6099 Approved
0.6611 Remote Similarity NPD6100 Approved
0.6609 Remote Similarity NPD9494 Approved
0.6604 Remote Similarity NPD7584 Approved
0.6598 Remote Similarity NPD7315 Approved
0.6595 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6595 Remote Similarity NPD8389 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