Structure

Physi-Chem Properties

Molecular Weight:  855.35
Volume:  856.086
LogP:  3.975
LogD:  2.456
LogS:  -4.513
# Rotatable Bonds:  15
TPSA:  224.45
# H-Bond Aceptor:  15
# H-Bond Donor:  5
# Rings:  7
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.112
Synthetic Accessibility Score:  6.039
Fsp3:  0.468
Lipinski Rule-of-5:  Rejected
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:  -5.632
MDCK Permeability:  6.136758747743443e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.379
20% Bioavailability (F20%):  0.971
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.062
Plasma Protein Binding (PPB):  93.23454284667969%
Volume Distribution (VD):  1.546
Pgp-substrate:  8.319557189941406%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.02
CYP2C19-inhibitor:  0.037
CYP2C19-substrate:  0.072
CYP2C9-inhibitor:  0.251
CYP2C9-substrate:  0.047
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.078
CYP3A4-inhibitor:  0.678
CYP3A4-substrate:  0.649

ADMET: Excretion

Clearance (CL):  4.304
Half-life (T1/2):  0.019

ADMET: Toxicity

hERG Blockers:  0.562
Human Hepatotoxicity (H-HT):  0.976
Drug-inuced Liver Injury (DILI):  0.977
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.088
Maximum Recommended Daily Dose:  0.804
Skin Sensitization:  0.039
Carcinogencity:  0.008
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.95

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

  Natural Product: NPC327699

Natural Product ID:  NPC327699
Common Name*:   RIYRAFARMCGSSW-UWNPAEFKSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  RIYRAFARMCGSSW-UWNPAEFKSA-N
Standard InCHI:  InChI=1S/C47H53NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-40,51-53,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,39-,40-,45+,46-,47+/m0/s1
SMILES:  CC(=O)O[C@H]1[C@H](O)[C@]2(C)[C@@H](O)C[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)N=C(c1ccccc1)O)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL37109
PubChem CID:   3081887
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0000676] Taxanes and derivatives

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

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[12217376]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota wood n.a. n.a. PMID[12444707]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota wood Yunnang Province, China 2000-OCT PMID[21138310]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. xylem n.a. PMID[21138310]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT81 Cell Line A549 Homo sapiens IC50 = 0.019 ug.mL-1 PMID[515224]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 0.08 ug.mL-1 PMID[515224]
NPT319 Cell Line B16 Mus musculus IC50 = 0.025 ug.mL-1 PMID[515224]
NPT168 Cell Line P388 Mus musculus IC50 = 0.053 ug.mL-1 PMID[515224]
NPT81 Cell Line A549 Homo sapiens Cytotoxicity = 22.0 ng ml-1 PMID[515225]
NPT139 Cell Line HT-29 Homo sapiens Cytotoxicity = 9.6 ng ml-1 PMID[515225]
NPT319 Cell Line B16 Mus musculus Cytotoxicity = 25.0 ng ml-1 PMID[515225]
NPT168 Cell Line P388 Mus musculus Cytotoxicity = 57.0 ng ml-1 PMID[515225]
NPT81 Cell Line A549 Homo sapiens Cytotoxicity = 11.0 ng ml-1 PMID[515226]
NPT139 Cell Line HT-29 Homo sapiens Cytotoxicity = 1.9 ng ml-1 PMID[515226]
NPT319 Cell Line B16 Mus musculus Cytotoxicity = 39.0 ng ml-1 PMID[515226]
NPT168 Cell Line P388 Mus musculus Cytotoxicity = 140.0 ng ml-1 PMID[515226]
NPT2 Others Unspecified Ratio = 0.86 n.a. PMID[515224]
NPT2 Others Unspecified Ratio = 0.75 n.a. PMID[515225]
NPT2 Others Unspecified Ratio = 0.83 n.a. PMID[515226]
NPT2 Others Unspecified EC50 = 749894209.33 nM PMID[515227]

☑ 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 NPC327699 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9653 High Similarity NPC321072
0.9653 High Similarity NPC215892
0.9653 High Similarity NPC242662
0.9653 High Similarity NPC191193
0.9598 High Similarity NPC471606
0.9598 High Similarity NPC208553
0.9598 High Similarity NPC181964
0.9543 High Similarity NPC473558
0.9432 High Similarity NPC473490
0.9422 High Similarity NPC453583
0.9422 High Similarity NPC475336
0.9422 High Similarity NPC473300
0.9368 High Similarity NPC33372
0.9368 High Similarity NPC67246
0.931 High Similarity NPC471754
0.931 High Similarity NPC317882
0.9278 High Similarity NPC289383
0.9227 High Similarity NPC116862
0.92 High Similarity NPC324251
0.92 High Similarity NPC473400
0.92 High Similarity NPC275170
0.92 High Similarity NPC306001
0.92 High Similarity NPC471629
0.92 High Similarity NPC206211
0.9111 High Similarity NPC472392
0.9061 High Similarity NPC472391
0.9034 High Similarity NPC471623
0.9006 High Similarity NPC472375
0.8533 High Similarity NPC36607
0.8084 Intermediate Similarity NPC38696
0.8012 Intermediate Similarity NPC470153
0.8 Intermediate Similarity NPC471101
0.8 Intermediate Similarity NPC476975
0.8 Intermediate Similarity NPC266265
0.8 Intermediate Similarity NPC92293
0.8 Intermediate Similarity NPC301556
0.8 Intermediate Similarity NPC270590
0.7988 Intermediate Similarity NPC474935
0.7964 Intermediate Similarity NPC34012
0.7955 Intermediate Similarity NPC476077
0.7953 Intermediate Similarity NPC470245
0.7953 Intermediate Similarity NPC473214
0.7941 Intermediate Similarity NPC281717
0.7929 Intermediate Similarity NPC174982
0.7929 Intermediate Similarity NPC70403
0.7929 Intermediate Similarity NPC470159
0.7929 Intermediate Similarity NPC472572
0.7929 Intermediate Similarity NPC473088
0.7929 Intermediate Similarity NPC472568
0.7929 Intermediate Similarity NPC184817
0.7929 Intermediate Similarity NPC177940
0.7929 Intermediate Similarity NPC472575
0.7929 Intermediate Similarity NPC200471
0.7929 Intermediate Similarity NPC471104
0.7929 Intermediate Similarity NPC158663
0.7929 Intermediate Similarity NPC171525
0.7929 Intermediate Similarity NPC472571
0.7929 Intermediate Similarity NPC470157
0.7929 Intermediate Similarity NPC476973
0.7929 Intermediate Similarity NPC469349
0.7929 Intermediate Similarity NPC96903
0.7929 Intermediate Similarity NPC29704
0.7929 Intermediate Similarity NPC472556
0.7919 Intermediate Similarity NPC134685
0.7919 Intermediate Similarity NPC248265
0.7919 Intermediate Similarity NPC11588
0.7919 Intermediate Similarity NPC229545
0.7895 Intermediate Similarity NPC473215
0.7877 Intermediate Similarity NPC30171
0.7874 Intermediate Similarity NPC259144
0.7874 Intermediate Similarity NPC26033
0.7874 Intermediate Similarity NPC114357
0.7874 Intermediate Similarity NPC155329
0.7874 Intermediate Similarity NPC228204
0.787 Intermediate Similarity NPC70716
0.787 Intermediate Similarity NPC25768
0.787 Intermediate Similarity NPC241951
0.787 Intermediate Similarity NPC475759
0.787 Intermediate Similarity NPC125106
0.787 Intermediate Similarity NPC475122
0.787 Intermediate Similarity NPC476974
0.787 Intermediate Similarity NPC11685
0.787 Intermediate Similarity NPC95265
0.787 Intermediate Similarity NPC188865
0.787 Intermediate Similarity NPC472570
0.787 Intermediate Similarity NPC95810
0.787 Intermediate Similarity NPC472573
0.787 Intermediate Similarity NPC163719
0.787 Intermediate Similarity NPC57628
0.787 Intermediate Similarity NPC472569
0.787 Intermediate Similarity NPC470152
0.7836 Intermediate Similarity NPC217918
0.7816 Intermediate Similarity NPC257213
0.7816 Intermediate Similarity NPC304876
0.7816 Intermediate Similarity NPC249471
0.7816 Intermediate Similarity NPC472005
0.7816 Intermediate Similarity NPC265395
0.7816 Intermediate Similarity NPC237549
0.7816 Intermediate Similarity NPC219419
0.7816 Intermediate Similarity NPC256142
0.7816 Intermediate Similarity NPC472030
0.7816 Intermediate Similarity NPC472022
0.7816 Intermediate Similarity NPC473414
0.7816 Intermediate Similarity NPC1173
0.7816 Intermediate Similarity NPC242262
0.7816 Intermediate Similarity NPC158333
0.7811 Intermediate Similarity NPC163087
0.7803 Intermediate Similarity NPC197037
0.7784 Intermediate Similarity NPC472393
0.7778 Intermediate Similarity NPC94602
0.7771 Intermediate Similarity NPC469730
0.7771 Intermediate Similarity NPC473611
0.7771 Intermediate Similarity NPC472549
0.7771 Intermediate Similarity NPC114410
0.7771 Intermediate Similarity NPC112523
0.7771 Intermediate Similarity NPC473632
0.7771 Intermediate Similarity NPC132599
0.7746 Intermediate Similarity NPC31829
0.7746 Intermediate Similarity NPC91730
0.7746 Intermediate Similarity NPC7095
0.774 Intermediate Similarity NPC471102
0.7727 Intermediate Similarity NPC106895
0.7727 Intermediate Similarity NPC217091
0.7722 Intermediate Similarity NPC471493
0.7714 Intermediate Similarity NPC77719
0.7709 Intermediate Similarity NPC253738
0.7706 Intermediate Similarity NPC191082
0.7706 Intermediate Similarity NPC139067
0.7706 Intermediate Similarity NPC475429
0.7706 Intermediate Similarity NPC147217
0.7706 Intermediate Similarity NPC246480
0.7706 Intermediate Similarity NPC270498
0.7706 Intermediate Similarity NPC473673
0.7706 Intermediate Similarity NPC177340
0.7692 Intermediate Similarity NPC224491
0.7692 Intermediate Similarity NPC41481
0.7692 Intermediate Similarity NPC87448
0.7692 Intermediate Similarity NPC472576
0.7692 Intermediate Similarity NPC27377
0.7692 Intermediate Similarity NPC291599
0.7692 Intermediate Similarity NPC16912
0.7692 Intermediate Similarity NPC97947
0.7692 Intermediate Similarity NPC118080
0.7688 Intermediate Similarity NPC250046
0.7688 Intermediate Similarity NPC60509
0.7688 Intermediate Similarity NPC81698
0.7684 Intermediate Similarity NPC469771
0.767 Intermediate Similarity NPC473670
0.767 Intermediate Similarity NPC21410
0.767 Intermediate Similarity NPC282239
0.7665 Intermediate Similarity NPC472372
0.7665 Intermediate Similarity NPC472374
0.7661 Intermediate Similarity NPC51314
0.7661 Intermediate Similarity NPC470231
0.7661 Intermediate Similarity NPC67777
0.7661 Intermediate Similarity NPC260194
0.7657 Intermediate Similarity NPC472548
0.7657 Intermediate Similarity NPC477905
0.7647 Intermediate Similarity NPC472546
0.7644 Intermediate Similarity NPC198455
0.7644 Intermediate Similarity NPC112216
0.7644 Intermediate Similarity NPC165260
0.7644 Intermediate Similarity NPC161239
0.7633 Intermediate Similarity NPC48017
0.7633 Intermediate Similarity NPC200592
0.7633 Intermediate Similarity NPC4341
0.7633 Intermediate Similarity NPC90614
0.7633 Intermediate Similarity NPC211137
0.7633 Intermediate Similarity NPC97667
0.7633 Intermediate Similarity NPC43241
0.7633 Intermediate Similarity NPC473112
0.7633 Intermediate Similarity NPC476094
0.7633 Intermediate Similarity NPC171207
0.7633 Intermediate Similarity NPC472547
0.7633 Intermediate Similarity NPC275592
0.7633 Intermediate Similarity NPC473081
0.7633 Intermediate Similarity NPC147880
0.7633 Intermediate Similarity NPC473109
0.7633 Intermediate Similarity NPC473060
0.7633 Intermediate Similarity NPC473085
0.7633 Intermediate Similarity NPC473758
0.7633 Intermediate Similarity NPC184747
0.7633 Intermediate Similarity NPC473613
0.7633 Intermediate Similarity NPC100913
0.763 Intermediate Similarity NPC473760
0.7602 Intermediate Similarity NPC91703
0.7574 Intermediate Similarity NPC210591
0.7574 Intermediate Similarity NPC472395
0.7574 Intermediate Similarity NPC214550
0.7574 Intermediate Similarity NPC472371
0.7574 Intermediate Similarity NPC475652
0.7572 Intermediate Similarity NPC48599
0.7572 Intermediate Similarity NPC20255
0.7572 Intermediate Similarity NPC473602
0.7572 Intermediate Similarity NPC209592
0.7515 Intermediate Similarity NPC283375
0.7515 Intermediate Similarity NPC39549
0.7515 Intermediate Similarity NPC183122
0.7514 Intermediate Similarity NPC127857
0.7514 Intermediate Similarity NPC125882

  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 NPC327699 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
0.9598 High Similarity NPD8485 Approved
0.9435 High Similarity NPD8486 Clinical (unspecified phase)
0.9143 High Similarity NPD8360 Approved
0.9143 High Similarity NPD8361 Approved
0.9034 High Similarity NPD8435 Approved
0.892 High Similarity NPD8424 Clinical (unspecified phase)
0.8786 High Similarity NPD8470 Clinical (unspecified phase)
0.8427 Intermediate Similarity NPD8368 Discontinued
0.8389 Intermediate Similarity NPD8407 Phase 2
0.7929 Intermediate Similarity NPD8462 Phase 1
0.7861 Intermediate Similarity NPD8404 Phase 2
0.7356 Intermediate Similarity NPD7274 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD8150 Discontinued
0.722 Intermediate Similarity NPD7874 Approved
0.722 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD7801 Approved
0.7175 Intermediate Similarity NPD8468 Phase 2
0.7165 Intermediate Similarity NPD8434 Phase 2
0.7143 Intermediate Similarity NPD8320 Phase 1
0.7143 Intermediate Similarity NPD8319 Approved
0.7123 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD7699 Phase 2
0.71 Intermediate Similarity NPD7700 Phase 2
0.7044 Intermediate Similarity NPD6823 Phase 2
0.7035 Intermediate Similarity NPD6534 Approved
0.7035 Intermediate Similarity NPD6535 Approved
0.7005 Intermediate Similarity NPD8151 Discontinued
0.6943 Remote Similarity NPD3823 Discontinued
0.6932 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6927 Remote Similarity NPD7236 Approved
0.6927 Remote Similarity NPD7497 Discontinued
0.6923 Remote Similarity NPD7239 Suspended
0.6907 Remote Similarity NPD5030 Phase 2
0.6893 Remote Similarity NPD7870 Phase 2
0.6893 Remote Similarity NPD7871 Phase 2
0.6875 Remote Similarity NPD7701 Phase 2
0.6875 Remote Similarity NPD7799 Discontinued
0.6872 Remote Similarity NPD5034 Approved
0.6872 Remote Similarity NPD4954 Approved
0.6872 Remote Similarity NPD36 Approved
0.6872 Remote Similarity NPD5026 Approved
0.6872 Remote Similarity NPD5028 Approved
0.6872 Remote Similarity NPD4955 Approved
0.6863 Remote Similarity NPD6779 Approved
0.6863 Remote Similarity NPD6777 Approved
0.6863 Remote Similarity NPD6782 Approved
0.6863 Remote Similarity NPD6780 Approved
0.6863 Remote Similarity NPD6778 Approved
0.6863 Remote Similarity NPD6781 Approved
0.6863 Remote Similarity NPD6776 Approved
0.6853 Remote Similarity NPD5036 Approved
0.6845 Remote Similarity NPD7697 Approved
0.6845 Remote Similarity NPD7696 Phase 3
0.6845 Remote Similarity NPD7698 Approved
0.6818 Remote Similarity NPD5038 Approved
0.6818 Remote Similarity NPD5037 Approved
0.6771 Remote Similarity NPD7997 Clinical (unspecified phase)
0.6763 Remote Similarity NPD7435 Discontinued
0.6737 Remote Similarity NPD6746 Phase 2
0.6703 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6629 Remote Similarity NPD7714 Approved
0.6629 Remote Similarity NPD7715 Approved
0.662 Remote Similarity NPD7783 Phase 2
0.662 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6619 Remote Similarity NPD7211 Clinical (unspecified phase)
0.661 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6601 Remote Similarity NPD8146 Phase 2
0.6601 Remote Similarity NPD3819 Phase 2
0.6601 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6601 Remote Similarity NPD5968 Phase 3
0.6583 Remote Similarity NPD5035 Approved
0.6577 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6577 Remote Similarity NPD8059 Phase 3
0.657 Remote Similarity NPD7565 Approved
0.6566 Remote Similarity NPD5029 Approved
0.6566 Remote Similarity NPD5031 Approved
0.6566 Remote Similarity NPD5027 Approved
0.6553 Remote Similarity NPD7282 Approved
0.6538 Remote Similarity NPD8166 Discontinued
0.6538 Remote Similarity NPD2575 Approved
0.6534 Remote Similarity NPD7713 Phase 3
0.6517 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6517 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6514 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6514 Remote Similarity NPD7008 Discontinued
0.6502 Remote Similarity NPD6836 Approved
0.65 Remote Similarity NPD7546 Discontinued
0.6492 Remote Similarity NPD7057 Phase 3
0.6492 Remote Similarity NPD7058 Phase 2
0.649 Remote Similarity NPD7810 Phase 3
0.649 Remote Similarity NPD7811 Phase 3
0.6489 Remote Similarity NPD6502 Phase 2
0.6482 Remote Similarity NPD7039 Approved
0.6482 Remote Similarity NPD7038 Approved
0.6471 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6458 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6457 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6453 Remote Similarity NPD7693 Approved
0.6447 Remote Similarity NPD7177 Discontinued
0.6443 Remote Similarity NPD8127 Discontinued
0.6436 Remote Similarity NPD3455 Phase 2
0.6433 Remote Similarity NPD6287 Discontinued
0.6429 Remote Similarity NPD6894 Phase 1
0.6422 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6421 Remote Similarity NPD7011 Discontinued
0.642 Remote Similarity NPD4738 Phase 2
0.6418 Remote Similarity NPD8313 Approved
0.6418 Remote Similarity NPD8312 Approved
0.6414 Remote Similarity NPD5844 Phase 1
0.6413 Remote Similarity NPD6190 Approved
0.6411 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6408 Remote Similarity NPD6213 Phase 3
0.6408 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6408 Remote Similarity NPD6212 Phase 3
0.6404 Remote Similarity NPD5119 Approved
0.6404 Remote Similarity NPD5120 Approved
0.6404 Remote Similarity NPD5121 Approved
0.64 Remote Similarity NPD8014 Clinical (unspecified phase)
0.6396 Remote Similarity NPD6997 Phase 2
0.6387 Remote Similarity NPD7972 Discontinued
0.6382 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6381 Remote Similarity NPD4914 Approved
0.6378 Remote Similarity NPD5242 Approved
0.6368 Remote Similarity NPD6677 Suspended
0.6368 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4617 Approved
0.6364 Remote Similarity NPD4620 Approved
0.6364 Remote Similarity NPD5201 Approved
0.6364 Remote Similarity NPD5203 Approved
0.6359 Remote Similarity NPD3400 Discontinued
0.6359 Remote Similarity NPD4628 Phase 3
0.6355 Remote Similarity NPD7583 Approved
0.6351 Remote Similarity NPD7907 Approved
0.635 Remote Similarity NPD7959 Clinical (unspecified phase)
0.635 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6347 Remote Similarity NPD2629 Approved
0.6346 Remote Similarity NPD7667 Clinical (unspecified phase)
0.634 Remote Similarity NPD7793 Clinical (unspecified phase)
0.6337 Remote Similarity NPD4807 Approved
0.6337 Remote Similarity NPD4806 Approved
0.6329 Remote Similarity NPD4466 Phase 1
0.6326 Remote Similarity NPD7585 Approved
0.6322 Remote Similarity NPD5667 Approved
0.6316 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6313 Remote Similarity NPD6309 Approved
0.6313 Remote Similarity NPD6311 Approved
0.6313 Remote Similarity NPD6310 Approved
0.6308 Remote Similarity NPD7999 Approved
0.6307 Remote Similarity NPD5204 Approved
0.6302 Remote Similarity NPD7460 Discontinued
0.6294 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6292 Remote Similarity NPD4621 Approved
0.6292 Remote Similarity NPD4619 Approved
0.629 Remote Similarity NPD3300 Phase 2
0.6289 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6287 Remote Similarity NPD5032 Approved
0.6287 Remote Similarity NPD8658 Clinical (unspecified phase)
0.6284 Remote Similarity NPD7827 Phase 1
0.6283 Remote Similarity NPD6386 Approved
0.6283 Remote Similarity NPD6385 Approved
0.6279 Remote Similarity NPD4106 Approved
0.6279 Remote Similarity NPD4136 Approved
0.6279 Remote Similarity NPD4135 Approved
0.6279 Remote Similarity NPD6973 Clinical (unspecified phase)
0.6272 Remote Similarity NPD8067 Phase 3
0.627 Remote Similarity NPD7253 Phase 3
0.627 Remote Similarity NPD7003 Approved
0.6264 Remote Similarity NPD182 Clinical (unspecified phase)
0.6264 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6264 Remote Similarity NPD5157 Phase 1
0.6264 Remote Similarity NPD5159 Phase 2
0.6263 Remote Similarity NPD7458 Discontinued
0.6263 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6263 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6261 Remote Similarity NPD4665 Approved
0.6257 Remote Similarity NPD7961 Discontinued
0.6256 Remote Similarity NPD5544 Approved
0.6256 Remote Similarity NPD8285 Discontinued
0.6256 Remote Similarity NPD6874 Approved
0.625 Remote Similarity NPD7596 Clinical (unspecified phase)
0.625 Remote Similarity NPD7029 Discontinued
0.6244 Remote Similarity NPD5848 Clinical (unspecified phase)
0.6244 Remote Similarity NPD7315 Approved
0.6244 Remote Similarity NPD4386 Approved
0.6244 Remote Similarity NPD4387 Approved
0.6238 Remote Similarity NPD5039 Approved
0.6237 Remote Similarity NPD7773 Phase 2
0.6237 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6237 Remote Similarity NPD7740 Clinical (unspecified phase)
0.6227 Remote Similarity NPD7930 Approved
0.6225 Remote Similarity NPD5946 Clinical (unspecified phase)
0.6223 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6221 Remote Similarity NPD5306 Approved
0.6221 Remote Similarity NPD5305 Approved
0.6219 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6218 Remote Similarity NPD4335 Clinical (unspecified phase)
0.6218 Remote Similarity NPD8455 Phase 2
0.6214 Remote Similarity NPD7291 Discontinued
0.6214 Remote Similarity NPD7906 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