Structure

Physi-Chem Properties

Molecular Weight:  1268.62
Volume:  1225.366
LogP:  2.257
LogD:  1.86
LogS:  -3.53
# Rotatable Bonds:  20
TPSA:  368.82
# H-Bond Aceptor:  26
# H-Bond Donor:  11
# Rings:  10
# Heavy Atoms:  26

MedChem Properties

QED Drug-Likeness Score:  0.05
Synthetic Accessibility Score:  7.428
Fsp3:  0.825
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:  -6.347
MDCK Permeability:  0.00022701786656398326
Pgp-inhibitor:  0.001
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.843
20% Bioavailability (F20%):  0.137
30% Bioavailability (F30%):  0.462

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.073
Plasma Protein Binding (PPB):  53.252891540527344%
Volume Distribution (VD):  -0.076
Pgp-substrate:  15.338507652282715%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.928
CYP2C19-inhibitor:  0.002
CYP2C19-substrate:  0.132
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.001
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.044
CYP3A4-inhibitor:  0.102
CYP3A4-substrate:  0.428

ADMET: Excretion

Clearance (CL):  0.108
Half-life (T1/2):  0.681

ADMET: Toxicity

hERG Blockers:  0.647
Human Hepatotoxicity (H-HT):  0.168
Drug-inuced Liver Injury (DILI):  0.064
AMES Toxicity:  0.298
Rat Oral Acute Toxicity:  0.312
Maximum Recommended Daily Dose:  0.953
Skin Sensitization:  0.944
Carcinogencity:  0.123
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.678

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

  Natural Product: NPC476092

Natural Product ID:  NPC476092
Common Name*:   12-O-Cinnamoylsarcostin 3-O-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranosyl-(1->4)-Beta-D-Oleandropyranosyl-(1->4)-Beta-D-Cymaropyranosyl-(1->4)-Beta-D-Cymaropyranoside
IUPAC Name:   [(3S,8S,9R,10R,12R,13R,14R,17R)-8,14,17-trihydroxy-17-[(1S)-1-hydroxyethyl]-3-[(2R,4S,5R,6R)-4-methoxy-5-[(2S,4S,5R,6R)-4-methoxy-5-[(2S,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] (E)-3-phenylprop-2-enoate
Synonyms:  
Standard InCHIKey:  QWEWFZFRJSUURV-WPIJPPRUSA-N
Standard InCHI:  InChI=1S/C63H96O26/c1-30-54(87-46-25-38(77-8)55(31(2)81-46)88-47-26-39(78-9)56(32(3)82-47)89-58-53(72)51(70)49(68)41(85-58)29-79-57-52(71)50(69)48(67)40(28-64)84-57)37(76-7)24-45(80-30)83-36-18-19-59(5)35(23-36)17-20-62(74)42(59)27-43(86-44(66)16-15-34-13-11-10-12-14-34)60(6)61(73,33(4)65)21-22-63(60,62)75/h10-17,30-33,36-43,45-58,64-65,67-75H,18-29H2,1-9H3/b16-15+/t30-,31-,32-,33+,36+,37+,38+,39+,40-,41-,42-,43-,45+,46+,47+,48-,49-,50+,51+,52-,53-,54-,55-,56-,57-,58+,59+,60-,61+,62+,63-/m1/s1
SMILES:  CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C(=CC[C@@]4([C@@H]3C[C@@H](OC(=O)/C=C/c3ccccc3)[C@]3([C@]4(O)CC[C@]3(O)[C@@H](O)C)C)O)C2)C)O[C@@H]([C@H]1O[C@H]1C[C@H](OC)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](OC)[C@@H]([C@H](O1)C)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL525771
PubChem CID:   44575252
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO32487 leptadenia pyrotechnica Species Apocynaceae Eukaryota whole plant Dogon region, Mali 2002-Apr PMID[16643040]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
UNPD: Universal Natural Products Database [PMID: 23638153].
StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
MetaboLights: a metabolomics database [PMID: 27010336].
FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT3470 Cell Line WEHI-164 Mus musculus IC50 = 940.0 nM PMID[456517]
NPT1182 Cell Line J774.A1 Mus musculus IC50 = 910.0 nM PMID[456517]

☑ 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 NPC476092 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 NPC475447
1.0 High Similarity NPC70236
1.0 High Similarity NPC475218
0.9929 High Similarity NPC474564
0.9272 High Similarity NPC473641
0.9272 High Similarity NPC475300
0.9272 High Similarity NPC475505
0.9272 High Similarity NPC475464
0.9272 High Similarity NPC475437
0.9272 High Similarity NPC473797
0.9205 High Similarity NPC165234
0.9205 High Similarity NPC475536
0.9091 High Similarity NPC475198
0.9091 High Similarity NPC475531
0.9091 High Similarity NPC475175
0.9026 High Similarity NPC473468
0.9026 High Similarity NPC475567
0.9026 High Similarity NPC473557
0.8882 High Similarity NPC476784
0.8828 High Similarity NPC473755
0.8828 High Similarity NPC475513
0.8649 High Similarity NPC264270
0.8649 High Similarity NPC40085
0.8616 High Similarity NPC477488
0.8609 High Similarity NPC478123
0.8581 High Similarity NPC111466
0.8476 Intermediate Similarity NPC475613
0.8456 Intermediate Similarity NPC471139
0.8452 Intermediate Similarity NPC477474
0.8452 Intermediate Similarity NPC477472
0.8452 Intermediate Similarity NPC477470
0.8428 Intermediate Similarity NPC477491
0.8418 Intermediate Similarity NPC269668
0.8397 Intermediate Similarity NPC477467
0.8369 Intermediate Similarity NPC476972
0.8369 Intermediate Similarity NPC476971
0.8366 Intermediate Similarity NPC62792
0.8366 Intermediate Similarity NPC298072
0.831 Intermediate Similarity NPC230331
0.8298 Intermediate Similarity NPC470158
0.8298 Intermediate Similarity NPC476970
0.8298 Intermediate Similarity NPC475933
0.828 Intermediate Similarity NPC319404
0.8258 Intermediate Similarity NPC69425
0.8247 Intermediate Similarity NPC329657
0.8228 Intermediate Similarity NPC477623
0.8207 Intermediate Similarity NPC476976
0.8205 Intermediate Similarity NPC471176
0.8187 Intermediate Similarity NPC478125
0.8182 Intermediate Similarity NPC476173
0.8138 Intermediate Similarity NPC476977
0.8133 Intermediate Similarity NPC325078
0.8125 Intermediate Similarity NPC478124
0.8101 Intermediate Similarity NPC318447
0.8101 Intermediate Similarity NPC322048
0.8099 Intermediate Similarity NPC471758
0.8089 Intermediate Similarity NPC469398
0.8085 Intermediate Similarity NPC473871
0.8085 Intermediate Similarity NPC473870
0.8065 Intermediate Similarity NPC475417
0.8065 Intermediate Similarity NPC475561
0.8056 Intermediate Similarity NPC58061
0.8049 Intermediate Similarity NPC477471
0.8049 Intermediate Similarity NPC477469
0.8049 Intermediate Similarity NPC477466
0.8049 Intermediate Similarity NPC477473
0.8042 Intermediate Similarity NPC473110
0.8042 Intermediate Similarity NPC45821
0.8042 Intermediate Similarity NPC473111
0.8038 Intermediate Similarity NPC323001
0.8038 Intermediate Similarity NPC326235
0.8028 Intermediate Similarity NPC470815
0.8026 Intermediate Similarity NPC284957
0.8025 Intermediate Similarity NPC472657
0.8025 Intermediate Similarity NPC471135
0.8025 Intermediate Similarity NPC77310
0.8025 Intermediate Similarity NPC472658
0.8014 Intermediate Similarity NPC70973
0.8014 Intermediate Similarity NPC473889
0.8 Intermediate Similarity NPC309991
0.8 Intermediate Similarity NPC93632
0.8 Intermediate Similarity NPC326328
0.8 Intermediate Similarity NPC323356
0.8 Intermediate Similarity NPC471138
0.7975 Intermediate Similarity NPC469422
0.7975 Intermediate Similarity NPC34066
0.7975 Intermediate Similarity NPC469456
0.7974 Intermediate Similarity NPC204644
0.7972 Intermediate Similarity NPC145287
0.7972 Intermediate Similarity NPC284022
0.7972 Intermediate Similarity NPC114927
0.7972 Intermediate Similarity NPC473083
0.7958 Intermediate Similarity NPC12016
0.7949 Intermediate Similarity NPC469448
0.7943 Intermediate Similarity NPC37641
0.7943 Intermediate Similarity NPC311175
0.7925 Intermediate Similarity NPC475548
0.7925 Intermediate Similarity NPC290683
0.7925 Intermediate Similarity NPC475638
0.7902 Intermediate Similarity NPC472373
0.7898 Intermediate Similarity NPC469415
0.7892 Intermediate Similarity NPC286809
0.7879 Intermediate Similarity NPC102465
0.7877 Intermediate Similarity NPC471024
0.7862 Intermediate Similarity NPC198918
0.7862 Intermediate Similarity NPC290276
0.7862 Intermediate Similarity NPC276047
0.7862 Intermediate Similarity NPC63404
0.7862 Intermediate Similarity NPC92283
0.7862 Intermediate Similarity NPC204214
0.7862 Intermediate Similarity NPC10121
0.7862 Intermediate Similarity NPC124878
0.7862 Intermediate Similarity NPC10883
0.7862 Intermediate Similarity NPC267733
0.7862 Intermediate Similarity NPC35338
0.7862 Intermediate Similarity NPC231888
0.7857 Intermediate Similarity NPC135369
0.7857 Intermediate Similarity NPC473566
0.7857 Intermediate Similarity NPC475358
0.7853 Intermediate Similarity NPC295408
0.7853 Intermediate Similarity NPC329960
0.7853 Intermediate Similarity NPC150893
0.7834 Intermediate Similarity NPC222102
0.7834 Intermediate Similarity NPC303429
0.7832 Intermediate Similarity NPC179261
0.7829 Intermediate Similarity NPC473440
0.7826 Intermediate Similarity NPC469399
0.7823 Intermediate Similarity NPC475138
0.7821 Intermediate Similarity NPC320734
0.7817 Intermediate Similarity NPC300827
0.7817 Intermediate Similarity NPC473439
0.7817 Intermediate Similarity NPC117445
0.7817 Intermediate Similarity NPC208193
0.7817 Intermediate Similarity NPC308262
0.7808 Intermediate Similarity NPC175333
0.7808 Intermediate Similarity NPC471025
0.7806 Intermediate Similarity NPC472575
0.7806 Intermediate Similarity NPC200471
0.7806 Intermediate Similarity NPC177940
0.7806 Intermediate Similarity NPC174982
0.7806 Intermediate Similarity NPC472572
0.7806 Intermediate Similarity NPC96447
0.7806 Intermediate Similarity NPC470157
0.7806 Intermediate Similarity NPC476973
0.7806 Intermediate Similarity NPC472571
0.7806 Intermediate Similarity NPC473088
0.7806 Intermediate Similarity NPC184817
0.7806 Intermediate Similarity NPC471104
0.7806 Intermediate Similarity NPC29704
0.7806 Intermediate Similarity NPC158663
0.7806 Intermediate Similarity NPC171525
0.7806 Intermediate Similarity NPC469349
0.7806 Intermediate Similarity NPC70403
0.7806 Intermediate Similarity NPC470159
0.7806 Intermediate Similarity NPC472568
0.7806 Intermediate Similarity NPC96903
0.7801 Intermediate Similarity NPC470814
0.7793 Intermediate Similarity NPC473082
0.7793 Intermediate Similarity NPC28069
0.7793 Intermediate Similarity NPC77651
0.7785 Intermediate Similarity NPC96308
0.7778 Intermediate Similarity NPC291599
0.7778 Intermediate Similarity NPC118080
0.7778 Intermediate Similarity NPC41481
0.7778 Intermediate Similarity NPC27377
0.7778 Intermediate Similarity NPC16912
0.7778 Intermediate Similarity NPC97947
0.7778 Intermediate Similarity NPC87448
0.7778 Intermediate Similarity NPC472576
0.7771 Intermediate Similarity NPC475121
0.7771 Intermediate Similarity NPC301556
0.7771 Intermediate Similarity NPC92293
0.7771 Intermediate Similarity NPC471101
0.7771 Intermediate Similarity NPC266265
0.7771 Intermediate Similarity NPC270590
0.7771 Intermediate Similarity NPC476067
0.7762 Intermediate Similarity NPC473749
0.7762 Intermediate Similarity NPC475328
0.7756 Intermediate Similarity NPC478263
0.7756 Intermediate Similarity NPC312393
0.7756 Intermediate Similarity NPC474935
0.7756 Intermediate Similarity NPC473602
0.775 Intermediate Similarity NPC5115
0.7746 Intermediate Similarity NPC474423
0.7746 Intermediate Similarity NPC193893
0.7746 Intermediate Similarity NPC264336
0.7746 Intermediate Similarity NPC74259
0.7742 Intermediate Similarity NPC57628
0.7742 Intermediate Similarity NPC470152
0.7742 Intermediate Similarity NPC25768
0.7742 Intermediate Similarity NPC95265
0.7742 Intermediate Similarity NPC163719
0.7742 Intermediate Similarity NPC475122
0.7742 Intermediate Similarity NPC472569
0.7742 Intermediate Similarity NPC11685
0.7742 Intermediate Similarity NPC70716
0.7742 Intermediate Similarity NPC188865
0.7742 Intermediate Similarity NPC125106
0.7742 Intermediate Similarity NPC95810
0.7742 Intermediate Similarity NPC475759

  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 NPC476092 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
0.7676 Intermediate Similarity NPD8033 Approved
0.7676 Intermediate Similarity NPD8379 Approved
0.7676 Intermediate Similarity NPD8296 Approved
0.7676 Intermediate Similarity NPD8378 Approved
0.7676 Intermediate Similarity NPD8380 Approved
0.7676 Intermediate Similarity NPD8335 Approved
0.7606 Intermediate Similarity NPD8294 Approved
0.7606 Intermediate Similarity NPD8377 Approved
0.7574 Intermediate Similarity NPD7799 Discontinued
0.7552 Intermediate Similarity NPD7503 Approved
0.7535 Intermediate Similarity NPD7516 Approved
0.7465 Intermediate Similarity NPD7327 Approved
0.7465 Intermediate Similarity NPD7328 Approved
0.7326 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD7236 Approved
0.7152 Intermediate Similarity NPD7266 Discontinued
0.7134 Intermediate Similarity NPD7239 Suspended
0.7123 Intermediate Similarity NPD7741 Discontinued
0.6987 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6913 Remote Similarity NPD5126 Approved
0.6913 Remote Similarity NPD5125 Phase 3
0.691 Remote Similarity NPD8368 Discontinued
0.6889 Remote Similarity NPD8407 Phase 2
0.6887 Remote Similarity NPD7507 Approved
0.6871 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6863 Remote Similarity NPD7319 Approved
0.6851 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6828 Remote Similarity NPD8133 Approved
0.6816 Remote Similarity NPD7685 Pre-registration
0.6782 Remote Similarity NPD8127 Discontinued
0.678 Remote Similarity NPD7228 Approved
0.6744 Remote Similarity NPD7058 Phase 2
0.6744 Remote Similarity NPD7057 Phase 3
0.6725 Remote Similarity NPD8455 Phase 2
0.6722 Remote Similarity NPD7240 Approved
0.6712 Remote Similarity NPD7094 Approved
0.6712 Remote Similarity NPD6858 Approved
0.6649 Remote Similarity NPD8361 Approved
0.6649 Remote Similarity NPD8360 Approved
0.6649 Remote Similarity NPD8435 Approved
0.6648 Remote Similarity NPD8313 Approved
0.6648 Remote Similarity NPD8312 Approved
0.6643 Remote Similarity NPD6685 Approved
0.6626 Remote Similarity NPD5763 Approved
0.6626 Remote Similarity NPD5762 Approved
0.6606 Remote Similarity NPD8166 Discontinued
0.6604 Remote Similarity NPD7961 Discontinued
0.6582 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6578 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6577 Remote Similarity NPD4198 Discontinued
0.6545 Remote Similarity NPD6674 Discontinued
0.6541 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6541 Remote Similarity NPD8434 Phase 2
0.6538 Remote Similarity NPD3094 Phase 2
0.6536 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6513 Remote Similarity NPD8516 Approved
0.6513 Remote Similarity NPD8515 Approved
0.6513 Remote Similarity NPD8517 Approved
0.651 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6497 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6474 Remote Similarity NPD37 Approved
0.6474 Remote Similarity NPD7736 Approved
0.646 Remote Similarity NPD4140 Approved
0.6457 Remote Similarity NPD4967 Phase 2
0.6457 Remote Similarity NPD4966 Approved
0.6457 Remote Similarity NPD4965 Approved
0.6456 Remote Similarity NPD5736 Approved
0.6453 Remote Similarity NPD7028 Phase 2
0.645 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6434 Remote Similarity NPD5765 Approved
0.6419 Remote Similarity NPD6912 Phase 3
0.641 Remote Similarity NPD7497 Discontinued
0.6405 Remote Similarity NPD8513 Phase 3
0.6404 Remote Similarity NPD7199 Phase 2
0.6384 Remote Similarity NPD6234 Discontinued
0.6378 Remote Similarity NPD8320 Phase 1
0.6378 Remote Similarity NPD8319 Approved
0.637 Remote Similarity NPD6686 Approved
0.6364 Remote Similarity NPD8150 Discontinued
0.6354 Remote Similarity NPD8485 Approved
0.6341 Remote Similarity NPD7097 Phase 1
0.6337 Remote Similarity NPD1653 Approved
0.6323 Remote Similarity NPD8328 Phase 3
0.6321 Remote Similarity NPD7700 Phase 2
0.6321 Remote Similarity NPD7699 Phase 2
0.6319 Remote Similarity NPD5735 Approved
0.6319 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6273 Approved
0.631 Remote Similarity NPD7625 Phase 1
0.6301 Remote Similarity NPD6412 Phase 2
0.6296 Remote Similarity NPD6663 Approved
0.6282 Remote Similarity NPD3092 Approved
0.6272 Remote Similarity NPD6190 Approved
0.625 Remote Similarity NPD7074 Phase 3
0.6243 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6225 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6211 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6207 Remote Similarity NPD7458 Discontinued
0.62 Remote Similarity NPD969 Suspended
0.6196 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6184 Remote Similarity NPD2629 Approved
0.6169 Remote Similarity NPD7610 Discontinued
0.6166 Remote Similarity NPD6534 Approved
0.6166 Remote Similarity NPD6535 Approved
0.6162 Remote Similarity NPD7435 Discontinued
0.6162 Remote Similarity NPD7680 Approved
0.6162 Remote Similarity NPD7472 Approved
0.6159 Remote Similarity NPD3620 Phase 2
0.6159 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6158 Remote Similarity NPD5760 Phase 2
0.6158 Remote Similarity NPD5761 Phase 2
0.6154 Remote Similarity NPD6370 Approved
0.6154 Remote Similarity NPD7638 Approved
0.6154 Remote Similarity NPD3095 Discontinued
0.615 Remote Similarity NPD7808 Phase 3
0.6144 Remote Similarity NPD7115 Discovery
0.6141 Remote Similarity NPD3751 Discontinued
0.6129 Remote Similarity NPD3091 Approved
0.6127 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6122 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6118 Remote Similarity NPD6010 Discontinued
0.6118 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6111 Remote Similarity NPD7640 Approved
0.6111 Remote Similarity NPD7055 Discontinued
0.6111 Remote Similarity NPD7639 Approved
0.6108 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6108 Remote Similarity NPD5844 Phase 1
0.6108 Remote Similarity NPD7783 Phase 2
0.6108 Remote Similarity NPD7054 Approved
0.6107 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6101 Remote Similarity NPD8293 Discontinued
0.6096 Remote Similarity NPD6647 Phase 2
0.6096 Remote Similarity NPD6559 Discontinued
0.6096 Remote Similarity NPD6764 Approved
0.6096 Remote Similarity NPD6765 Approved
0.6096 Remote Similarity NPD7251 Discontinued
0.6093 Remote Similarity NPD8297 Approved
0.6093 Remote Similarity NPD6882 Approved
0.6089 Remote Similarity NPD8151 Discontinued
0.6084 Remote Similarity NPD6653 Approved
0.6084 Remote Similarity NPD6353 Approved
0.608 Remote Similarity NPD7697 Approved
0.608 Remote Similarity NPD7696 Phase 3
0.608 Remote Similarity NPD7698 Approved
0.6076 Remote Similarity NPD7492 Approved
0.6069 Remote Similarity NPD5344 Discontinued
0.6069 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6059 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6059 Remote Similarity NPD7874 Approved
0.6056 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6049 Remote Similarity NPD7084 Phase 3
0.6043 Remote Similarity NPD6797 Phase 2
0.604 Remote Similarity NPD7701 Phase 2
0.6039 Remote Similarity NPD6009 Approved
0.6039 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6038 Remote Similarity NPD6616 Approved
0.6036 Remote Similarity NPD6002 Phase 3
0.6036 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6036 Remote Similarity NPD6004 Phase 3
0.6036 Remote Similarity NPD6005 Phase 3
0.6036 Remote Similarity NPD6003 Clinical (unspecified phase)
0.603 Remote Similarity NPD6823 Phase 2
0.6026 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6026 Remote Similarity NPD6319 Approved
0.6026 Remote Similarity NPD7009 Phase 2
0.6026 Remote Similarity NPD6054 Approved
0.6024 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6024 Remote Similarity NPD5124 Phase 1
0.6023 Remote Similarity NPD4628 Phase 3
0.6023 Remote Similarity NPD7982 Clinical (unspecified phase)
0.6011 Remote Similarity NPD3787 Discontinued
0.601 Remote Similarity NPD6776 Approved
0.601 Remote Similarity NPD6781 Approved
0.601 Remote Similarity NPD6779 Approved
0.601 Remote Similarity NPD6780 Approved
0.601 Remote Similarity NPD6778 Approved
0.601 Remote Similarity NPD6777 Approved
0.601 Remote Similarity NPD6782 Approved
0.6 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6 Remote Similarity NPD6648 Approved
0.6 Remote Similarity NPD8462 Phase 1
0.6 Remote Similarity NPD5327 Phase 3
0.6 Remote Similarity NPD7078 Approved
0.5988 Remote Similarity NPD4624 Approved
0.5979 Remote Similarity NPD8658 Clinical (unspecified phase)
0.5976 Remote Similarity NPD8450 Suspended
0.5976 Remote Similarity NPD7008 Discontinued
0.597 Remote Similarity NPD7870 Phase 2
0.597 Remote Similarity NPD7871 Phase 2
0.5969 Remote Similarity NPD6785 Approved
0.5969 Remote Similarity NPD6784 Approved
0.5957 Remote Similarity NPD7993 Clinical (unspecified phase)
0.5951 Remote Similarity NPD7801 Approved
0.5948 Remote Similarity NPD4632 Approved
0.5939 Remote Similarity NPD6410 Clinical (unspecified phase)
0.5931 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5921 Remote Similarity NPD4141 Clinical (unspecified phase)
0.592 Remote Similarity NPD6143 Clinical (unspecified phase)
0.5915 Remote Similarity NPD8449 Approved
0.5915 Remote Similarity NPD8171 Discontinued

  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