Structure

Physi-Chem Properties

Molecular Weight:  847.38
Volume:  852.619
LogP:  3.943
LogD:  1.805
LogS:  -3.594
# Rotatable Bonds:  18
TPSA:  221.29
# H-Bond Aceptor:  15
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.091
Synthetic Accessibility Score:  6.215
Fsp3:  0.565
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:  -5.362
MDCK Permeability:  4.728056228486821e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.057
20% Bioavailability (F20%):  0.977
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.13
Plasma Protein Binding (PPB):  96.22176361083984%
Volume Distribution (VD):  1.092
Pgp-substrate:  6.3348188400268555%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.067
CYP2C19-inhibitor:  0.174
CYP2C19-substrate:  0.159
CYP2C9-inhibitor:  0.761
CYP2C9-substrate:  0.029
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.047
CYP3A4-inhibitor:  0.92
CYP3A4-substrate:  0.784

ADMET: Excretion

Clearance (CL):  3.714
Half-life (T1/2):  0.038

ADMET: Toxicity

hERG Blockers:  0.241
Human Hepatotoxicity (H-HT):  0.704
Drug-inuced Liver Injury (DILI):  0.941
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.937
Maximum Recommended Daily Dose:  0.931
Skin Sensitization:  0.273
Carcinogencity:  0.063
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.981

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

  Natural Product: NPC306001

Natural Product ID:  NPC306001
Common Name*:   BEHTXUBGUDGCNQ-QJUJXNPASA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  BEHTXUBGUDGCNQ-QJUJXNPASA-N
Standard InCHI:  InChI=1S/C46H57NO14/c1-8-9-12-21-33(51)47-35(28-17-13-10-14-18-28)36(52)42(55)59-30-23-46(56)40(60-41(54)29-19-15-11-16-20-29)38-44(7,31(50)22-32-45(38,24-57-32)61-27(4)49)39(53)37(58-26(3)48)34(25(30)2)43(46,5)6/h10-11,13-20,30-32,35-38,40,50,52,56H,8-9,12,21-24H2,1-7H3,(H,47,51)/t30-,31-,32+,35-,36+,37+,38?,40-,44+,45-,46+/m0/s1
SMILES:  CCCCCC(=N[C@H]([C@H](C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)C3[C@@](C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)(C)[C@@H](O)C[C@@H]1[C@]3(CO1)OC(=O)C)O)c1ccccc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1479301
PubChem CID:   24791028
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]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. Japan n.a. PMID[14987066]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[15844936]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[15974623]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. Japan n.a. PMID[15974623]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota needles Himalayan n.a. PMID[16480866]
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]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[23265441]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota Stem Bark n.a. n.a. PMID[28240909]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota Roots n.a. n.a. PMID[28581744]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[7264680]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[7561894]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[7908950]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23840 Taxus x media Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15125.2 Taxus wallichiana var. wallichiana Varieties Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23840 Taxus x media Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23840 Taxus x media Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15125.2 Taxus wallichiana var. wallichiana Varieties Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23840 Taxus x media Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23720 Taxus wallichiana 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
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency = 35.5 nM PMID[497388]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 12589.3 nM PMID[497388]
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 794.3 nM PMID[497388]
NPT538 Individual Protein Niemann-Pick C1 protein Homo sapiens Potency = 8912.5 nM PMID[497388]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 11220.2 nM PMID[497388]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 29092.9 nM PMID[497388]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 79432.8 nM PMID[497388]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 22387.2 nM PMID[497388]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 11220.2 nM PMID[497388]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 183.6 nM PMID[497388]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 6309.6 nM PMID[497388]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 103.2 nM PMID[497388]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 115.8 nM PMID[497388]
NPT2 Others Unspecified EC50 = 402.0 nM PMID[497388]
NPT2 Others Unspecified EC50 < 100.0 nM PMID[497388]
NPT2 Others Unspecified EC50 = 229.0 nM PMID[497388]
NPT2 Others Unspecified IC50 = 61.84 nM PMID[497388]
NPT2 Others Unspecified EC50 = 253.0 nM PMID[497388]
NPT2 Others Unspecified IC50 > 80000.0 nM PMID[497388]
NPT2 Others Unspecified IC50 = 32300.0 nM PMID[497388]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 73.8 nM PMID[497388]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 261.7 nM PMID[497388]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[497388]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 89125.1 nM PMID[497388]
NPT2 Others Unspecified Potency n.a. 5.8 nM PMID[497388]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 5.2 nM PMID[497388]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[497388]
NPT2 Others Unspecified Potency n.a. 7943.3 nM PMID[497388]
NPT2 Others Unspecified Potency n.a. 25118.9 nM PMID[497388]

☑ 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 NPC306001 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 NPC275170
1.0 High Similarity NPC473400
1.0 High Similarity NPC206211
1.0 High Similarity NPC471629
1.0 High Similarity NPC324251
0.9882 High Similarity NPC317882
0.9882 High Similarity NPC471754
0.9825 High Similarity NPC33372
0.9825 High Similarity NPC67246
0.9766 High Similarity NPC453583
0.9766 High Similarity NPC473300
0.9766 High Similarity NPC475336
0.9708 High Similarity NPC471623
0.96 High Similarity NPC471606
0.96 High Similarity NPC208553
0.96 High Similarity NPC181964
0.9545 High Similarity NPC473558
0.9543 High Similarity NPC215892
0.9543 High Similarity NPC242662
0.9543 High Similarity NPC321072
0.9543 High Similarity NPC191193
0.9438 High Similarity NPC472375
0.9435 High Similarity NPC473490
0.9385 High Similarity NPC472391
0.933 High Similarity NPC472392
0.9231 High Similarity NPC116862
0.92 High Similarity NPC327699
0.9176 High Similarity NPC289383
0.9162 High Similarity NPC36607
0.8462 Intermediate Similarity NPC219419
0.8412 Intermediate Similarity NPC259144
0.8412 Intermediate Similarity NPC114357
0.8412 Intermediate Similarity NPC155329
0.8353 Intermediate Similarity NPC229545
0.8353 Intermediate Similarity NPC134685
0.8353 Intermediate Similarity NPC248265
0.8353 Intermediate Similarity NPC11588
0.8314 Intermediate Similarity NPC472393
0.8284 Intermediate Similarity NPC91730
0.8256 Intermediate Similarity NPC217091
0.8256 Intermediate Similarity NPC106895
0.8239 Intermediate Similarity NPC471493
0.8235 Intermediate Similarity NPC197037
0.8198 Intermediate Similarity NPC473670
0.8198 Intermediate Similarity NPC228204
0.8198 Intermediate Similarity NPC21410
0.8198 Intermediate Similarity NPC282239
0.8198 Intermediate Similarity NPC26033
0.8176 Intermediate Similarity NPC7095
0.8166 Intermediate Similarity NPC217918
0.814 Intermediate Similarity NPC472005
0.814 Intermediate Similarity NPC249471
0.814 Intermediate Similarity NPC304876
0.814 Intermediate Similarity NPC256142
0.814 Intermediate Similarity NPC1173
0.814 Intermediate Similarity NPC265395
0.814 Intermediate Similarity NPC472030
0.814 Intermediate Similarity NPC242262
0.814 Intermediate Similarity NPC237549
0.814 Intermediate Similarity NPC257213
0.814 Intermediate Similarity NPC473414
0.814 Intermediate Similarity NPC158333
0.814 Intermediate Similarity NPC472022
0.8129 Intermediate Similarity NPC306799
0.8129 Intermediate Similarity NPC101043
0.8129 Intermediate Similarity NPC471103
0.8129 Intermediate Similarity NPC51602
0.8118 Intermediate Similarity NPC81698
0.8118 Intermediate Similarity NPC60509
0.8118 Intermediate Similarity NPC250046
0.8092 Intermediate Similarity NPC472549
0.8092 Intermediate Similarity NPC112523
0.8092 Intermediate Similarity NPC114410
0.807 Intermediate Similarity NPC198455
0.807 Intermediate Similarity NPC112216
0.807 Intermediate Similarity NPC165260
0.807 Intermediate Similarity NPC161239
0.8057 Intermediate Similarity NPC471102
0.8047 Intermediate Similarity NPC127857
0.8035 Intermediate Similarity NPC77719
0.8 Intermediate Similarity NPC469771
0.7977 Intermediate Similarity NPC472548
0.7965 Intermediate Similarity NPC470245
0.7965 Intermediate Similarity NPC254558
0.7965 Intermediate Similarity NPC473214
0.7919 Intermediate Similarity NPC470153
0.7907 Intermediate Similarity NPC476975
0.7907 Intermediate Similarity NPC473215
0.7895 Intermediate Similarity NPC474935
0.7886 Intermediate Similarity NPC473632
0.7886 Intermediate Similarity NPC473611
0.7886 Intermediate Similarity NPC469730
0.7886 Intermediate Similarity NPC132599
0.7882 Intermediate Similarity NPC38696
0.7874 Intermediate Similarity NPC477905
0.787 Intermediate Similarity NPC182869
0.787 Intermediate Similarity NPC34012
0.7836 Intermediate Similarity NPC471107
0.7836 Intermediate Similarity NPC277053
0.7836 Intermediate Similarity NPC471100
0.7836 Intermediate Similarity NPC301946
0.7778 Intermediate Similarity NPC471912
0.7778 Intermediate Similarity NPC80895
0.7765 Intermediate Similarity NPC476077
0.7753 Intermediate Similarity NPC469399
0.7733 Intermediate Similarity NPC472572
0.7733 Intermediate Similarity NPC158663
0.7733 Intermediate Similarity NPC470159
0.7733 Intermediate Similarity NPC70403
0.7733 Intermediate Similarity NPC184817
0.7733 Intermediate Similarity NPC200471
0.7733 Intermediate Similarity NPC473088
0.7733 Intermediate Similarity NPC472575
0.7733 Intermediate Similarity NPC472571
0.7733 Intermediate Similarity NPC470157
0.7733 Intermediate Similarity NPC174982
0.7733 Intermediate Similarity NPC471104
0.7733 Intermediate Similarity NPC171525
0.7733 Intermediate Similarity NPC29704
0.7733 Intermediate Similarity NPC469349
0.7733 Intermediate Similarity NPC96903
0.7733 Intermediate Similarity NPC472568
0.7733 Intermediate Similarity NPC476973
0.7733 Intermediate Similarity NPC177940
0.7705 Intermediate Similarity NPC102465
0.7697 Intermediate Similarity NPC469417
0.7688 Intermediate Similarity NPC94602
0.768 Intermediate Similarity NPC66193
0.7674 Intermediate Similarity NPC470152
0.7674 Intermediate Similarity NPC475122
0.7674 Intermediate Similarity NPC241951
0.7674 Intermediate Similarity NPC472573
0.7674 Intermediate Similarity NPC70716
0.7674 Intermediate Similarity NPC188865
0.7674 Intermediate Similarity NPC125106
0.7674 Intermediate Similarity NPC95810
0.7674 Intermediate Similarity NPC475759
0.7674 Intermediate Similarity NPC11685
0.7674 Intermediate Similarity NPC476974
0.7674 Intermediate Similarity NPC25768
0.7674 Intermediate Similarity NPC472570
0.7674 Intermediate Similarity NPC472569
0.7674 Intermediate Similarity NPC163719
0.7674 Intermediate Similarity NPC95265
0.7674 Intermediate Similarity NPC470231
0.7674 Intermediate Similarity NPC57628
0.7661 Intermediate Similarity NPC472546
0.764 Intermediate Similarity NPC11410
0.7637 Intermediate Similarity NPC471134
0.763 Intermediate Similarity NPC473541
0.763 Intermediate Similarity NPC472556
0.7624 Intermediate Similarity NPC253738
0.7624 Intermediate Similarity NPC55744
0.7616 Intermediate Similarity NPC163087
0.7616 Intermediate Similarity NPC477894
0.7602 Intermediate Similarity NPC213567
0.7602 Intermediate Similarity NPC16912
0.7602 Intermediate Similarity NPC97947
0.7602 Intermediate Similarity NPC118080
0.7602 Intermediate Similarity NPC87448
0.7602 Intermediate Similarity NPC41481
0.7602 Intermediate Similarity NPC224491
0.7602 Intermediate Similarity NPC472576
0.7602 Intermediate Similarity NPC27377
0.7602 Intermediate Similarity NPC291599
0.76 Intermediate Similarity NPC301556
0.76 Intermediate Similarity NPC92293
0.76 Intermediate Similarity NPC266265
0.76 Intermediate Similarity NPC471101
0.76 Intermediate Similarity NPC270590
0.7596 Intermediate Similarity NPC61891
0.7596 Intermediate Similarity NPC30171
0.7594 Intermediate Similarity NPC96801
0.7594 Intermediate Similarity NPC150698
0.7584 Intermediate Similarity NPC251139
0.7582 Intermediate Similarity NPC150893
0.7582 Intermediate Similarity NPC295408
0.7582 Intermediate Similarity NPC329960
0.7572 Intermediate Similarity NPC260194
0.7568 Intermediate Similarity NPC278272
0.7568 Intermediate Similarity NPC477469
0.7568 Intermediate Similarity NPC120667
0.7568 Intermediate Similarity NPC477473
0.7568 Intermediate Similarity NPC477471
0.7568 Intermediate Similarity NPC477466
0.7544 Intermediate Similarity NPC275592
0.7544 Intermediate Similarity NPC472547
0.7544 Intermediate Similarity NPC97667
0.7544 Intermediate Similarity NPC171207
0.7544 Intermediate Similarity NPC100913
0.7544 Intermediate Similarity NPC90614
0.7543 Intermediate Similarity NPC281717
0.7543 Intermediate Similarity NPC473760
0.7528 Intermediate Similarity NPC133430
0.7528 Intermediate Similarity NPC469477
0.7514 Intermediate Similarity NPC40138
0.7486 Intermediate Similarity NPC209592
0.7486 Intermediate Similarity NPC5115
0.7486 Intermediate Similarity NPC48599
0.7486 Intermediate Similarity NPC477737

  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 NPC306001 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
0.9708 High Similarity NPD8435 Approved
0.96 High Similarity NPD8485 Approved
0.9593 High Similarity NPD8361 Approved
0.9593 High Similarity NPD8360 Approved
0.9438 High Similarity NPD8486 Clinical (unspecified phase)
0.9364 High Similarity NPD8424 Clinical (unspecified phase)
0.9075 High Similarity NPD8368 Discontinued
0.9029 High Similarity NPD8407 Phase 2
0.8686 High Similarity NPD8470 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD8462 Phase 1
0.8232 Intermediate Similarity NPD8404 Phase 2
0.7539 Intermediate Similarity NPD8150 Discontinued
0.7539 Intermediate Similarity NPD8434 Phase 2
0.7488 Intermediate Similarity NPD7874 Approved
0.7488 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD7801 Approved
0.7413 Intermediate Similarity NPD8320 Phase 1
0.7413 Intermediate Similarity NPD8319 Approved
0.734 Intermediate Similarity NPD7799 Discontinued
0.7299 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD7700 Phase 2
0.7286 Intermediate Similarity NPD7699 Phase 2
0.7232 Intermediate Similarity NPD7236 Approved
0.7222 Intermediate Similarity NPD6534 Approved
0.7222 Intermediate Similarity NPD6535 Approved
0.7222 Intermediate Similarity NPD7239 Suspended
0.7175 Intermediate Similarity NPD7274 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD5030 Phase 2
0.7062 Intermediate Similarity NPD36 Approved
0.7062 Intermediate Similarity NPD5026 Approved
0.7062 Intermediate Similarity NPD5034 Approved
0.7062 Intermediate Similarity NPD4954 Approved
0.7062 Intermediate Similarity NPD5028 Approved
0.7062 Intermediate Similarity NPD4955 Approved
0.7053 Intermediate Similarity NPD7701 Phase 2
0.7044 Intermediate Similarity NPD6777 Approved
0.7044 Intermediate Similarity NPD6781 Approved
0.7044 Intermediate Similarity NPD6776 Approved
0.7044 Intermediate Similarity NPD6779 Approved
0.7044 Intermediate Similarity NPD6780 Approved
0.7044 Intermediate Similarity NPD6778 Approved
0.7044 Intermediate Similarity NPD6782 Approved
0.7041 Intermediate Similarity NPD5036 Approved
0.7035 Intermediate Similarity NPD8468 Phase 2
0.7024 Intermediate Similarity NPD7698 Approved
0.7024 Intermediate Similarity NPD7697 Approved
0.7024 Intermediate Similarity NPD7696 Phase 3
0.7024 Intermediate Similarity NPD7435 Discontinued
0.7019 Intermediate Similarity NPD8151 Discontinued
0.7005 Intermediate Similarity NPD5038 Approved
0.7005 Intermediate Similarity NPD5037 Approved
0.699 Remote Similarity NPD7870 Phase 2
0.699 Remote Similarity NPD7871 Phase 2
0.6976 Remote Similarity NPD6823 Phase 2
0.6961 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6872 Remote Similarity NPD3823 Discontinued
0.6866 Remote Similarity NPD7879 Clinical (unspecified phase)
0.686 Remote Similarity NPD7497 Discontinued
0.6854 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7972 Discontinued
0.6818 Remote Similarity NPD8059 Phase 3
0.6818 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6794 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6772 Remote Similarity NPD7058 Phase 2
0.6772 Remote Similarity NPD7057 Phase 3
0.6768 Remote Similarity NPD5035 Approved
0.6751 Remote Similarity NPD5027 Approved
0.6751 Remote Similarity NPD5031 Approved
0.6751 Remote Similarity NPD5029 Approved
0.6743 Remote Similarity NPD7907 Approved
0.6732 Remote Similarity NPD7282 Approved
0.6714 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6714 Remote Similarity NPD7783 Phase 2
0.67 Remote Similarity NPD5968 Phase 3
0.67 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6683 Remote Similarity NPD6836 Approved
0.6667 Remote Similarity NPD7460 Discontinued
0.6631 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6615 Remote Similarity NPD7997 Clinical (unspecified phase)
0.6614 Remote Similarity NPD7029 Discontinued
0.6612 Remote Similarity NPD6190 Approved
0.661 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6587 Remote Similarity NPD7811 Phase 3
0.6587 Remote Similarity NPD7810 Phase 3
0.6587 Remote Similarity NPD8285 Discontinued
0.6587 Remote Similarity NPD7565 Approved
0.6585 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6585 Remote Similarity NPD6213 Phase 3
0.6585 Remote Similarity NPD6212 Phase 3
0.6579 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6578 Remote Similarity NPD8067 Phase 3
0.6575 Remote Similarity NPD4665 Approved
0.6564 Remote Similarity NPD5242 Approved
0.6562 Remote Similarity NPD7075 Discontinued
0.6557 Remote Similarity NPD2575 Approved
0.6555 Remote Similarity NPD4914 Approved
0.6537 Remote Similarity NPD3819 Phase 2
0.6531 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6526 Remote Similarity NPD6973 Clinical (unspecified phase)
0.6516 Remote Similarity NPD8366 Approved
0.6508 Remote Similarity NPD6599 Discontinued
0.65 Remote Similarity NPD4111 Phase 1
0.649 Remote Similarity NPD2975 Approved
0.649 Remote Similarity NPD2974 Approved
0.649 Remote Similarity NPD2973 Approved
0.6476 Remote Similarity NPD4580 Approved
0.6474 Remote Similarity NPD6386 Approved
0.6474 Remote Similarity NPD6385 Approved
0.6473 Remote Similarity NPD8491 Approved
0.6468 Remote Similarity NPD7962 Phase 2
0.6468 Remote Similarity NPD5032 Approved
0.6461 Remote Similarity NPD7713 Phase 3
0.6458 Remote Similarity NPD5402 Approved
0.6457 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6445 Remote Similarity NPD2494 Approved
0.6445 Remote Similarity NPD2493 Approved
0.6445 Remote Similarity NPD3450 Approved
0.6445 Remote Similarity NPD3452 Approved
0.6444 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6441 Remote Similarity NPD4738 Phase 2
0.644 Remote Similarity NPD6801 Discontinued
0.6439 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6432 Remote Similarity NPD4583 Approved
0.6432 Remote Similarity NPD4582 Approved
0.6429 Remote Similarity NPD7315 Approved
0.6429 Remote Similarity NPD5544 Approved
0.6415 Remote Similarity NPD4386 Approved
0.6415 Remote Similarity NPD4387 Approved
0.6414 Remote Similarity NPD7473 Discontinued
0.641 Remote Similarity NPD6746 Phase 2
0.6408 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6406 Remote Similarity NPD7819 Suspended
0.6402 Remote Similarity NPD7999 Approved
0.64 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6398 Remote Similarity NPD3300 Phase 2
0.6393 Remote Similarity NPD7930 Approved
0.6385 Remote Similarity NPD4002 Approved
0.6385 Remote Similarity NPD4004 Approved
0.6382 Remote Similarity NPD3751 Discontinued
0.6378 Remote Similarity NPD3400 Discontinued
0.6378 Remote Similarity NPD4628 Phase 3
0.6373 Remote Similarity NPD3817 Phase 2
0.6372 Remote Similarity NPD7584 Approved
0.6372 Remote Similarity NPD7583 Approved
0.6369 Remote Similarity NPD7714 Approved
0.6369 Remote Similarity NPD7961 Discontinued
0.6369 Remote Similarity NPD7715 Approved
0.6355 Remote Similarity NPD8313 Approved
0.6355 Remote Similarity NPD8312 Approved
0.6351 Remote Similarity NPD6874 Approved
0.635 Remote Similarity NPD7804 Clinical (unspecified phase)
0.635 Remote Similarity NPD5844 Phase 1
0.6348 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6343 Remote Similarity NPD5667 Approved
0.6343 Remote Similarity NPD7585 Approved
0.6341 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6338 Remote Similarity NPD3057 Approved
0.6337 Remote Similarity NPD8014 Clinical (unspecified phase)
0.6335 Remote Similarity NPD4380 Phase 2
0.6321 Remote Similarity NPD4107 Approved
0.6311 Remote Similarity NPD7693 Approved
0.6308 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6305 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6305 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6301 Remote Similarity NPD7827 Phase 1
0.63 Remote Similarity NPD7177 Discontinued
0.6298 Remote Similarity NPD8146 Phase 2
0.6296 Remote Similarity NPD6296 Discontinued
0.6294 Remote Similarity NPD8127 Discontinued
0.6293 Remote Similarity NPD7048 Phase 3
0.6292 Remote Similarity NPD5202 Clinical (unspecified phase)
0.629 Remote Similarity NPD8166 Discontinued
0.6287 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6287 Remote Similarity NPD7959 Clinical (unspecified phase)
0.6283 Remote Similarity NPD3455 Phase 2
0.6281 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6281 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6281 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6281 Remote Similarity NPD6166 Phase 2
0.6277 Remote Similarity NPD6799 Approved
0.6275 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6274 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6269 Remote Similarity NPD6844 Discontinued
0.6269 Remote Similarity NPD7011 Discontinued
0.6268 Remote Similarity NPD4466 Phase 1
0.6264 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6264 Remote Similarity NPD6287 Discontinued
0.6263 Remote Similarity NPD3787 Discontinued
0.6263 Remote Similarity NPD5403 Approved
0.6263 Remote Similarity NPD6232 Discontinued
0.6262 Remote Similarity NPD7683 Discontinued
0.6262 Remote Similarity NPD5006 Approved
0.6262 Remote Similarity NPD2972 Approved
0.6262 Remote Similarity NPD3533 Approved
0.6262 Remote Similarity NPD8162 Phase 2
0.6262 Remote Similarity NPD5005 Approved
0.6262 Remote Similarity NPD8163 Clinical (unspecified phase)
0.6256 Remote Similarity NPD6104 Discontinued
0.6256 Remote Similarity NPD7038 Approved
0.6256 Remote Similarity NPD7039 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