Structure

Physi-Chem Properties

Molecular Weight:  809.3
Volume:  810.067
LogP:  3.614
LogD:  2.274
LogS:  -4.474
# Rotatable Bonds:  13
TPSA:  212.06
# H-Bond Aceptor:  14
# H-Bond Donor:  4
# Rings:  7
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.139
Synthetic Accessibility Score:  5.816
Fsp3:  0.422
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.473
MDCK Permeability:  5.08191624248866e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.086
20% Bioavailability (F20%):  0.959
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.159
Plasma Protein Binding (PPB):  91.0848617553711%
Volume Distribution (VD):  1.385
Pgp-substrate:  6.723836898803711%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.048
CYP2C19-inhibitor:  0.14
CYP2C19-substrate:  0.08
CYP2C9-inhibitor:  0.872
CYP2C9-substrate:  0.049
CYP2D6-inhibitor:  0.077
CYP2D6-substrate:  0.065
CYP3A4-inhibitor:  0.788
CYP3A4-substrate:  0.558

ADMET: Excretion

Clearance (CL):  4.767
Half-life (T1/2):  0.023

ADMET: Toxicity

hERG Blockers:  0.679
Human Hepatotoxicity (H-HT):  0.941
Drug-inuced Liver Injury (DILI):  0.951
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.365
Maximum Recommended Daily Dose:  0.94
Skin Sensitization:  0.057
Carcinogencity:  0.028
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.871

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

  Natural Product: NPC191193

Natural Product ID:  NPC191193
Common Name*:   CJCYABFPESVRKC-QRTSWCPHSA-N
IUPAC Name:   n.a.
Synonyms:   10-Oxotaxol
Standard InCHIKey:  CJCYABFPESVRKC-QRTSWCPHSA-N
Standard InCHI:  InChI=1S/C45H47NO13/c1-24-29(57-41(54)35(50)33(26-15-9-6-10-16-26)46-39(52)27-17-11-7-12-18-27)22-45(55)38(58-40(53)28-19-13-8-14-20-28)36-43(5,37(51)34(49)32(24)42(45,3)4)30(48)21-31-44(36,23-56-31)59-25(2)47/h6-20,29-31,33,35-36,38,48,50,55H,21-23H2,1-5H3,(H,46,52)/t29-,30-,31+,33-,35+,36-,38-,43+,44-,45+/m0/s1
SMILES:  CC(=O)O[C@@]12CO[C@@H]1C[C@@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@@H]([C@H](c3ccccc3)N=C(c3ccccc3)O)O)C(=C(C2(C)C)C(=O)C1=O)C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL507766
PubChem CID:   10581238
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
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. twig n.a. DOI[10.1016/j.tet.2004.10.110]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. leaf n.a. DOI[10.1016/j.tet.2004.10.110]
NPO13290 Taxus canadensis Species Taxaceae Eukaryota Needles n.a. n.a. PMID[11325226]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota leaves and twigs n.a. n.a. PMID[12502326]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. leaf n.a. PMID[15679325]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[15679325]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. twig n.a. PMID[15679325]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[18220355]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[1955887]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[2878063]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[7130988]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota bark n.a. n.a. PMID[7623034]
NPO13290 Taxus canadensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15125.1 Taxus wallichiana var. chinensis Varieties Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13290 Taxus canadensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13290 Taxus canadensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15125.1 Taxus wallichiana var. chinensis Varieties Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13290 Taxus canadensis Species Taxaceae 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
NPT91 Cell Line KB Homo sapiens ED50 = 2.0 10'-2 ug/ml PMID[483614]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 64.0 nM PMID[483615]
NPT91 Cell Line KB Homo sapiens ED50 = 2.0 10'-2 ug/ml PMID[483616]

☑ 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 NPC191193 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 NPC215892
1.0 High Similarity NPC242662
1.0 High Similarity NPC321072
0.9943 High Similarity NPC181964
0.9943 High Similarity NPC471606
0.9943 High Similarity NPC208553
0.9886 High Similarity NPC473558
0.9773 High Similarity NPC473490
0.9769 High Similarity NPC475336
0.9769 High Similarity NPC453583
0.9769 High Similarity NPC473300
0.9713 High Similarity NPC67246
0.9713 High Similarity NPC33372
0.9655 High Similarity NPC471754
0.9655 High Similarity NPC317882
0.9653 High Similarity NPC327699
0.9611 High Similarity NPC289383
0.9558 High Similarity NPC116862
0.9543 High Similarity NPC306001
0.9543 High Similarity NPC206211
0.9543 High Similarity NPC324251
0.9543 High Similarity NPC275170
0.9543 High Similarity NPC471629
0.9543 High Similarity NPC473400
0.9444 High Similarity NPC472392
0.9392 High Similarity NPC472391
0.9375 High Similarity NPC471623
0.9337 High Similarity NPC472375
0.8859 High Similarity NPC36607
0.8266 Intermediate Similarity NPC134685
0.8266 Intermediate Similarity NPC11588
0.8266 Intermediate Similarity NPC229545
0.8266 Intermediate Similarity NPC248265
0.8218 Intermediate Similarity NPC259144
0.8218 Intermediate Similarity NPC228204
0.8218 Intermediate Similarity NPC26033
0.8218 Intermediate Similarity NPC114357
0.8218 Intermediate Similarity NPC155329
0.8161 Intermediate Similarity NPC219419
0.8161 Intermediate Similarity NPC472005
0.8161 Intermediate Similarity NPC265395
0.8161 Intermediate Similarity NPC237549
0.8161 Intermediate Similarity NPC158333
0.8161 Intermediate Similarity NPC473414
0.8161 Intermediate Similarity NPC242262
0.8161 Intermediate Similarity NPC472030
0.8161 Intermediate Similarity NPC304876
0.8161 Intermediate Similarity NPC249471
0.8161 Intermediate Similarity NPC256142
0.8161 Intermediate Similarity NPC257213
0.8161 Intermediate Similarity NPC1173
0.8161 Intermediate Similarity NPC472022
0.815 Intermediate Similarity NPC197037
0.8125 Intermediate Similarity NPC472393
0.8114 Intermediate Similarity NPC112523
0.8114 Intermediate Similarity NPC114410
0.8092 Intermediate Similarity NPC91730
0.8092 Intermediate Similarity NPC7095
0.8079 Intermediate Similarity NPC471102
0.8068 Intermediate Similarity NPC217091
0.8068 Intermediate Similarity NPC106895
0.8057 Intermediate Similarity NPC77719
0.8056 Intermediate Similarity NPC471493
0.8035 Intermediate Similarity NPC250046
0.8035 Intermediate Similarity NPC60509
0.8035 Intermediate Similarity NPC81698
0.8023 Intermediate Similarity NPC469771
0.8011 Intermediate Similarity NPC472549
0.8011 Intermediate Similarity NPC21410
0.8011 Intermediate Similarity NPC473670
0.8011 Intermediate Similarity NPC282239
0.7989 Intermediate Similarity NPC161239
0.7989 Intermediate Similarity NPC165260
0.7989 Intermediate Similarity NPC112216
0.7989 Intermediate Similarity NPC198455
0.7989 Intermediate Similarity NPC476077
0.7977 Intermediate Similarity NPC217918
0.7943 Intermediate Similarity NPC470153
0.7898 Intermediate Similarity NPC477905
0.7898 Intermediate Similarity NPC472548
0.7861 Intermediate Similarity NPC127857
0.7841 Intermediate Similarity NPC101043
0.7841 Intermediate Similarity NPC471103
0.7841 Intermediate Similarity NPC306799
0.7841 Intermediate Similarity NPC51602
0.7809 Intermediate Similarity NPC469730
0.7809 Intermediate Similarity NPC132599
0.7809 Intermediate Similarity NPC473632
0.7809 Intermediate Similarity NPC473611
0.7803 Intermediate Similarity NPC38696
0.7784 Intermediate Similarity NPC470245
0.7784 Intermediate Similarity NPC254558
0.7784 Intermediate Similarity NPC473214
0.7727 Intermediate Similarity NPC270590
0.7727 Intermediate Similarity NPC301556
0.7727 Intermediate Similarity NPC473215
0.7727 Intermediate Similarity NPC476975
0.7727 Intermediate Similarity NPC92293
0.7727 Intermediate Similarity NPC471101
0.7727 Intermediate Similarity NPC266265
0.7714 Intermediate Similarity NPC474935
0.7688 Intermediate Similarity NPC34012
0.767 Intermediate Similarity NPC281717
0.7657 Intermediate Similarity NPC174982
0.7657 Intermediate Similarity NPC473088
0.7657 Intermediate Similarity NPC472575
0.7657 Intermediate Similarity NPC184817
0.7657 Intermediate Similarity NPC470157
0.7657 Intermediate Similarity NPC29704
0.7657 Intermediate Similarity NPC158663
0.7657 Intermediate Similarity NPC472572
0.7657 Intermediate Similarity NPC472568
0.7657 Intermediate Similarity NPC171525
0.7657 Intermediate Similarity NPC472571
0.7657 Intermediate Similarity NPC471104
0.7657 Intermediate Similarity NPC177940
0.7657 Intermediate Similarity NPC200471
0.7657 Intermediate Similarity NPC476973
0.7657 Intermediate Similarity NPC70403
0.7657 Intermediate Similarity NPC470159
0.7657 Intermediate Similarity NPC472556
0.7657 Intermediate Similarity NPC96903
0.7657 Intermediate Similarity NPC469349
0.7622 Intermediate Similarity NPC30171
0.76 Intermediate Similarity NPC472573
0.76 Intermediate Similarity NPC472570
0.76 Intermediate Similarity NPC188865
0.76 Intermediate Similarity NPC25768
0.76 Intermediate Similarity NPC95810
0.76 Intermediate Similarity NPC70716
0.76 Intermediate Similarity NPC11685
0.76 Intermediate Similarity NPC163719
0.76 Intermediate Similarity NPC125106
0.76 Intermediate Similarity NPC241951
0.76 Intermediate Similarity NPC475759
0.76 Intermediate Similarity NPC475122
0.76 Intermediate Similarity NPC57628
0.76 Intermediate Similarity NPC470152
0.76 Intermediate Similarity NPC472569
0.76 Intermediate Similarity NPC476974
0.76 Intermediate Similarity NPC95265
0.7586 Intermediate Similarity NPC182869
0.7582 Intermediate Similarity NPC469399
0.7569 Intermediate Similarity NPC11410
0.7568 Intermediate Similarity NPC471134
0.7557 Intermediate Similarity NPC471107
0.7557 Intermediate Similarity NPC471100
0.7557 Intermediate Similarity NPC277053
0.7557 Intermediate Similarity NPC301946
0.7543 Intermediate Similarity NPC477894
0.7543 Intermediate Similarity NPC163087
0.754 Intermediate Similarity NPC102465
0.7529 Intermediate Similarity NPC213567
0.7527 Intermediate Similarity NPC469417
0.7514 Intermediate Similarity NPC329960
0.7514 Intermediate Similarity NPC295408
0.7514 Intermediate Similarity NPC472371
0.7514 Intermediate Similarity NPC66193
0.7514 Intermediate Similarity NPC472395
0.7514 Intermediate Similarity NPC94602
0.7514 Intermediate Similarity NPC150893
0.7514 Intermediate Similarity NPC251139
0.75 Intermediate Similarity NPC471912
0.75 Intermediate Similarity NPC477473
0.75 Intermediate Similarity NPC80895
0.75 Intermediate Similarity NPC278272
0.75 Intermediate Similarity NPC477466
0.75 Intermediate Similarity NPC477469
0.75 Intermediate Similarity NPC470231
0.75 Intermediate Similarity NPC120667
0.75 Intermediate Similarity NPC477471
0.7486 Intermediate Similarity NPC31829
0.7474 Intermediate Similarity NPC469421
0.7459 Intermediate Similarity NPC253738
0.7458 Intermediate Similarity NPC473541
0.7454 Intermediate Similarity NPC150698
0.7454 Intermediate Similarity NPC96801
0.745 Intermediate Similarity NPC42286
0.7448 Intermediate Similarity NPC475649
0.7447 Intermediate Similarity NPC469420
0.7443 Intermediate Similarity NPC246480
0.7443 Intermediate Similarity NPC139067
0.7443 Intermediate Similarity NPC473673
0.7443 Intermediate Similarity NPC270498
0.7443 Intermediate Similarity NPC147217
0.7443 Intermediate Similarity NPC177340
0.7443 Intermediate Similarity NPC191082
0.7443 Intermediate Similarity NPC477468
0.7443 Intermediate Similarity NPC475429
0.7438 Intermediate Similarity NPC314941
0.7433 Intermediate Similarity NPC61891
0.7429 Intermediate Similarity NPC87448
0.7429 Intermediate Similarity NPC16912
0.7429 Intermediate Similarity NPC41481
0.7429 Intermediate Similarity NPC472576
0.7429 Intermediate Similarity NPC27377
0.7429 Intermediate Similarity NPC224491
0.7429 Intermediate Similarity NPC97947
0.7429 Intermediate Similarity NPC291599
0.7429 Intermediate Similarity NPC118080

  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 NPC191193 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
0.9943 High Similarity NPD8485 Approved
0.9774 High Similarity NPD8486 Clinical (unspecified phase)
0.9486 High Similarity NPD8360 Approved
0.9486 High Similarity NPD8361 Approved
0.9375 High Similarity NPD8435 Approved
0.9045 High Similarity NPD8424 Clinical (unspecified phase)
0.8764 High Similarity NPD8368 Discontinued
0.8722 High Similarity NPD8407 Phase 2
0.8492 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD8462 Phase 1
0.8159 Intermediate Similarity NPD8404 Phase 2
0.7656 Intermediate Similarity NPD8150 Discontinued
0.7512 Intermediate Similarity NPD7874 Approved
0.7512 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7476 Intermediate Similarity NPD7801 Approved
0.7474 Intermediate Similarity NPD8434 Phase 2
0.7438 Intermediate Similarity NPD8319 Approved
0.7438 Intermediate Similarity NPD8320 Phase 1
0.7406 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD7699 Phase 2
0.74 Intermediate Similarity NPD7700 Phase 2
0.7337 Intermediate Similarity NPD6534 Approved
0.7337 Intermediate Similarity NPD6535 Approved
0.7295 Intermediate Similarity NPD8151 Discontinued
0.7184 Intermediate Similarity NPD7871 Phase 2
0.7184 Intermediate Similarity NPD7870 Phase 2
0.7171 Intermediate Similarity NPD6823 Phase 2
0.7163 Intermediate Similarity NPD7701 Phase 2
0.7157 Intermediate Similarity NPD6780 Approved
0.7157 Intermediate Similarity NPD6778 Approved
0.7157 Intermediate Similarity NPD6781 Approved
0.7157 Intermediate Similarity NPD6782 Approved
0.7157 Intermediate Similarity NPD6779 Approved
0.7157 Intermediate Similarity NPD6777 Approved
0.7157 Intermediate Similarity NPD6776 Approved
0.7136 Intermediate Similarity NPD7696 Phase 3
0.7136 Intermediate Similarity NPD7698 Approved
0.7136 Intermediate Similarity NPD7697 Approved
0.7128 Intermediate Similarity NPD5030 Phase 2
0.7111 Intermediate Similarity NPD7274 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD7799 Discontinued
0.7092 Intermediate Similarity NPD5026 Approved
0.7092 Intermediate Similarity NPD4954 Approved
0.7092 Intermediate Similarity NPD4955 Approved
0.7092 Intermediate Similarity NPD5034 Approved
0.7092 Intermediate Similarity NPD36 Approved
0.7092 Intermediate Similarity NPD5028 Approved
0.7071 Intermediate Similarity NPD5036 Approved
0.7053 Intermediate Similarity NPD7435 Discontinued
0.7035 Intermediate Similarity NPD5038 Approved
0.7035 Intermediate Similarity NPD5037 Approved
0.699 Remote Similarity NPD3823 Discontinued
0.6987 Remote Similarity NPD8468 Phase 2
0.6978 Remote Similarity NPD7236 Approved
0.6973 Remote Similarity NPD7239 Suspended
0.6905 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7879 Clinical (unspecified phase)
0.689 Remote Similarity NPD7497 Discontinued
0.6847 Remote Similarity NPD8059 Phase 3
0.6847 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6822 Remote Similarity NPD7783 Phase 2
0.6822 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6811 Remote Similarity NPD8389 Clinical (unspecified phase)
0.68 Remote Similarity NPD5035 Approved
0.6796 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6784 Remote Similarity NPD5031 Approved
0.6784 Remote Similarity NPD5029 Approved
0.6784 Remote Similarity NPD5027 Approved
0.6763 Remote Similarity NPD7282 Approved
0.6732 Remote Similarity NPD5968 Phase 3
0.6716 Remote Similarity NPD6836 Approved
0.6699 Remote Similarity NPD6212 Phase 3
0.6699 Remote Similarity NPD6213 Phase 3
0.6699 Remote Similarity NPD6214 Clinical (unspecified phase)
0.665 Remote Similarity NPD8055 Clinical (unspecified phase)
0.665 Remote Similarity NPD3819 Phase 2
0.6634 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6622 Remote Similarity NPD7907 Approved
0.6619 Remote Similarity NPD7811 Phase 3
0.6619 Remote Similarity NPD7810 Phase 3
0.6615 Remote Similarity NPD7972 Discontinued
0.6588 Remote Similarity NPD4914 Approved
0.6579 Remote Similarity NPD6591 Clinical (unspecified phase)
0.657 Remote Similarity NPD8146 Phase 2
0.6566 Remote Similarity NPD7997 Clinical (unspecified phase)
0.6558 Remote Similarity NPD6973 Clinical (unspecified phase)
0.6552 Remote Similarity NPD8312 Approved
0.6552 Remote Similarity NPD8313 Approved
0.6546 Remote Similarity NPD7058 Phase 2
0.6546 Remote Similarity NPD7057 Phase 3
0.654 Remote Similarity NPD7565 Approved
0.654 Remote Similarity NPD8285 Discontinued
0.6535 Remote Similarity NPD8067 Phase 3
0.6532 Remote Similarity NPD4665 Approved
0.6531 Remote Similarity NPD6746 Phase 2
0.6505 Remote Similarity NPD2575 Approved
0.6502 Remote Similarity NPD5032 Approved
0.6485 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6473 Remote Similarity NPD8366 Approved
0.6471 Remote Similarity NPD6190 Approved
0.6462 Remote Similarity NPD5544 Approved
0.6457 Remote Similarity NPD4111 Phase 1
0.645 Remote Similarity NPD7473 Discontinued
0.6449 Remote Similarity NPD4387 Approved
0.6449 Remote Similarity NPD4386 Approved
0.6436 Remote Similarity NPD3300 Phase 2
0.6432 Remote Similarity NPD8491 Approved
0.6432 Remote Similarity NPD5242 Approved
0.6429 Remote Similarity NPD7075 Discontinued
0.6418 Remote Similarity NPD7177 Discontinued
0.6417 Remote Similarity NPD8166 Discontinued
0.6416 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6409 Remote Similarity NPD7713 Phase 3
0.6409 Remote Similarity NPD7714 Approved
0.6409 Remote Similarity NPD7715 Approved
0.64 Remote Similarity NPD6166 Phase 2
0.64 Remote Similarity NPD6168 Clinical (unspecified phase)
0.64 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6393 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6386 Remote Similarity NPD5844 Phase 1
0.6381 Remote Similarity NPD4466 Phase 1
0.6376 Remote Similarity NPD7654 Discontinued
0.6374 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6359 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6359 Remote Similarity NPD7460 Discontinued
0.6355 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6351 Remote Similarity NPD7930 Approved
0.634 Remote Similarity NPD6385 Approved
0.634 Remote Similarity NPD6386 Approved
0.6337 Remote Similarity NPD3751 Discontinued
0.633 Remote Similarity NPD3400 Discontinued
0.633 Remote Similarity NPD4628 Phase 3
0.633 Remote Similarity NPD7584 Approved
0.633 Remote Similarity NPD7583 Approved
0.6327 Remote Similarity NPD5402 Approved
0.6326 Remote Similarity NPD2493 Approved
0.6326 Remote Similarity NPD3452 Approved
0.6326 Remote Similarity NPD2494 Approved
0.6326 Remote Similarity NPD3450 Approved
0.6321 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6321 Remote Similarity NPD7458 Discontinued
0.6318 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6318 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6313 Remote Similarity NPD4583 Approved
0.6313 Remote Similarity NPD4582 Approved
0.6311 Remote Similarity NPD7546 Discontinued
0.6308 Remote Similarity NPD6801 Discontinued
0.6308 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6308 Remote Similarity NPD7029 Discontinued
0.6307 Remote Similarity NPD6287 Discontinued
0.6305 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6304 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6301 Remote Similarity NPD7585 Approved
0.63 Remote Similarity NPD7315 Approved
0.63 Remote Similarity NPD6232 Discontinued
0.6298 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6298 Remote Similarity NPD7008 Discontinued
0.6294 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6293 Remote Similarity NPD7038 Approved
0.6293 Remote Similarity NPD7039 Approved
0.6291 Remote Similarity NPD2973 Approved
0.6291 Remote Similarity NPD2974 Approved
0.6291 Remote Similarity NPD2975 Approved
0.6289 Remote Similarity NPD6502 Phase 2
0.6289 Remote Similarity NPD4380 Phase 2
0.6289 Remote Similarity NPD6599 Discontinued
0.6286 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6284 Remote Similarity NPD7999 Approved
0.6279 Remote Similarity NPD4580 Approved
0.6276 Remote Similarity NPD7819 Suspended
0.6268 Remote Similarity NPD7693 Approved
0.6267 Remote Similarity NPD4004 Approved
0.6267 Remote Similarity NPD4002 Approved
0.6263 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6262 Remote Similarity NPD4974 Approved
0.6262 Remote Similarity NPD7962 Phase 2
0.6262 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6262 Remote Similarity NPD4975 Approved
0.6256 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6255 Remote Similarity NPD7048 Phase 3
0.625 Remote Similarity NPD8127 Discontinued
0.6244 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6243 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6238 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6238 Remote Similarity NPD6894 Phase 1
0.6237 Remote Similarity NPD3455 Phase 2
0.6233 Remote Similarity NPD5608 Approved
0.6233 Remote Similarity NPD6874 Approved
0.6233 Remote Similarity NPD5609 Approved
0.623 Remote Similarity NPD7961 Discontinued
0.6228 Remote Similarity NPD6997 Phase 2
0.6224 Remote Similarity NPD7011 Discontinued
0.6221 Remote Similarity NPD3057 Approved
0.622 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6219 Remote Similarity NPD3787 Discontinued
0.6216 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6214 Remote Similarity NPD8014 Clinical (unspecified phase)
0.6214 Remote Similarity NPD5039 Approved
0.6209 Remote Similarity NPD4738 Phase 2
0.6198 Remote Similarity NPD8367 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