Structure

Physi-Chem Properties

Molecular Weight:  768.3
Volume:  757.829
LogP:  2.382
LogD:  1.63
LogS:  -4.964
# Rotatable Bonds:  16
TPSA:  204.33
# H-Bond Aceptor:  15
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.157
Synthetic Accessibility Score:  6.624
Fsp3:  0.575
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:  -5.345
MDCK Permeability:  0.0001307719066971913
Pgp-inhibitor:  0.998
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.815
20% Bioavailability (F20%):  0.843
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.534
Plasma Protein Binding (PPB):  50.282371520996094%
Volume Distribution (VD):  1.596
Pgp-substrate:  26.491283416748047%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.017
CYP2C19-inhibitor:  0.025
CYP2C19-substrate:  0.064
CYP2C9-inhibitor:  0.094
CYP2C9-substrate:  0.008
CYP2D6-inhibitor:  0.679
CYP2D6-substrate:  0.027
CYP3A4-inhibitor:  0.654
CYP3A4-substrate:  0.428

ADMET: Excretion

Clearance (CL):  2.976
Half-life (T1/2):  0.294

ADMET: Toxicity

hERG Blockers:  0.053
Human Hepatotoxicity (H-HT):  0.97
Drug-inuced Liver Injury (DILI):  0.947
AMES Toxicity:  0.063
Rat Oral Acute Toxicity:  0.561
Maximum Recommended Daily Dose:  0.746
Skin Sensitization:  0.359
Carcinogencity:  0.103
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.965

Download Data

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

  Natural Product: NPC471912

Natural Product ID:  NPC471912
Common Name*:   AECANJMDROLQQG-OOIPFWLNSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  AECANJMDROLQQG-OOIPFWLNSA-N
Standard InCHI:  InChI=1S/C40H48O15/c1-21-29(55-32(47)15-14-27-12-10-9-11-13-27)19-31(51-23(3)42)39(16-17-49-22(2)41)33(21)34(52-24(4)43)28-18-30(46)38(8)40(48,37(28,7)20-50-38)36(54-26(6)45)35(39)53-25(5)44/h9-15,28-29,31,33-36,48H,1,16-20H2,2-8H3/b15-14+/t28-,29-,31-,33-,34+,35-,36-,37-,38+,39+,40-/m0/s1
SMILES:  CC(=O)OCCC12C(CC(C(=C)C1C(C3CC(=O)C4(C(C3(CO4)C)(C(C2OC(=O)C)OC(=O)C)O)C)OC(=O)C)OC(=O)C=CC5=CC=CC=C5)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL329348
PubChem CID:   44327230
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002967] Hexacarboxylic acids 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]
NPO31343 Taxus chinensis 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]
NPO31343 Taxus chinensis 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]
NPO31343 Taxus chinensis 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
NPT1178 Cell Line KB 3-1 Homo sapiens ED50 = 17.0 ug ml-1 PMID[511796]
NPT1178 Cell Line KB 3-1 Homo sapiens ED50 = 4.6 ug ml-1 PMID[511796]
NPT27 Others Unspecified ED50 = 6.2 ug ml-1 PMID[511796]

☑ 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 NPC471912 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 NPC80895
0.9926 High Similarity NPC301946
0.9926 High Similarity NPC277053
0.9375 High Similarity NPC21410
0.9375 High Similarity NPC473670
0.931 High Similarity NPC217091
0.9301 High Similarity NPC51602
0.927 High Similarity NPC184109
0.9247 High Similarity NPC472393
0.9167 High Similarity NPC471103
0.911 High Similarity NPC282239
0.9085 High Similarity NPC127857
0.9048 High Similarity NPC106895
0.9044 High Similarity NPC209851
0.8971 High Similarity NPC476977
0.8966 High Similarity NPC112216
0.8966 High Similarity NPC7095
0.8951 High Similarity NPC471100
0.8951 High Similarity NPC471107
0.8926 High Similarity NPC471102
0.8912 High Similarity NPC219419
0.8905 High Similarity NPC476976
0.8905 High Similarity NPC80599
0.8904 High Similarity NPC306799
0.8904 High Similarity NPC101043
0.8897 High Similarity NPC60509
0.8897 High Similarity NPC81698
0.8897 High Similarity NPC250046
0.8851 High Similarity NPC472549
0.8851 High Similarity NPC155329
0.8851 High Similarity NPC114357
0.8851 High Similarity NPC259144
0.8836 High Similarity NPC165260
0.8836 High Similarity NPC198455
0.8836 High Similarity NPC254558
0.8836 High Similarity NPC161239
0.8815 High Similarity NPC473423
0.8784 High Similarity NPC11588
0.8784 High Similarity NPC472022
0.8784 High Similarity NPC265395
0.8784 High Similarity NPC229545
0.8784 High Similarity NPC77719
0.8784 High Similarity NPC249471
0.8784 High Similarity NPC248265
0.8784 High Similarity NPC257213
0.8784 High Similarity NPC1173
0.8784 High Similarity NPC158333
0.8784 High Similarity NPC237549
0.8784 High Similarity NPC242262
0.8784 High Similarity NPC473414
0.8784 High Similarity NPC304876
0.8784 High Similarity NPC472005
0.8784 High Similarity NPC256142
0.8784 High Similarity NPC134685
0.8784 High Similarity NPC472030
0.8759 High Similarity NPC473443
0.875 High Similarity NPC195224
0.8741 High Similarity NPC182869
0.8725 High Similarity NPC26033
0.8725 High Similarity NPC114410
0.8725 High Similarity NPC112523
0.8725 High Similarity NPC228204
0.8716 High Similarity NPC477905
0.8716 High Similarity NPC472548
0.8707 High Similarity NPC473214
0.8707 High Similarity NPC470245
0.8707 High Similarity NPC91730
0.8696 High Similarity NPC472418
0.8686 High Similarity NPC225103
0.8671 High Similarity NPC16912
0.8658 High Similarity NPC69425
0.8649 High Similarity NPC197037
0.8649 High Similarity NPC470153
0.8639 High Similarity NPC476975
0.8639 High Similarity NPC473215
0.863 High Similarity NPC474935
0.8623 High Similarity NPC472388
0.8611 High Similarity NPC472546
0.8611 High Similarity NPC63737
0.8609 High Similarity NPC469771
0.8603 High Similarity NPC473082
0.8603 High Similarity NPC476970
0.8601 High Similarity NPC171207
0.8601 High Similarity NPC97667
0.8571 High Similarity NPC15850
0.8571 High Similarity NPC217918
0.8553 High Similarity NPC477467
0.8542 High Similarity NPC291599
0.8542 High Similarity NPC118080
0.8542 High Similarity NPC87448
0.8542 High Similarity NPC97947
0.8542 High Similarity NPC27377
0.8542 High Similarity NPC41481
0.8542 High Similarity NPC472576
0.854 High Similarity NPC476971
0.854 High Similarity NPC476972
0.8529 High Similarity NPC473083
0.8523 High Similarity NPC329657
0.8516 High Similarity NPC471493
0.8506 High Similarity NPC55744
0.8503 High Similarity NPC477737
0.8493 Intermediate Similarity NPC163719
0.8493 Intermediate Similarity NPC472569
0.8493 Intermediate Similarity NPC70716
0.8493 Intermediate Similarity NPC57628
0.8493 Intermediate Similarity NPC125106
0.8493 Intermediate Similarity NPC25768
0.8493 Intermediate Similarity NPC95265
0.8493 Intermediate Similarity NPC472570
0.8493 Intermediate Similarity NPC470231
0.8493 Intermediate Similarity NPC188865
0.8493 Intermediate Similarity NPC11685
0.8493 Intermediate Similarity NPC476974
0.8493 Intermediate Similarity NPC95810
0.8493 Intermediate Similarity NPC472573
0.8487 Intermediate Similarity NPC477474
0.8487 Intermediate Similarity NPC477470
0.8487 Intermediate Similarity NPC477472
0.8483 Intermediate Similarity NPC34012
0.8477 Intermediate Similarity NPC473611
0.8472 Intermediate Similarity NPC275592
0.8472 Intermediate Similarity NPC90614
0.8472 Intermediate Similarity NPC473440
0.8472 Intermediate Similarity NPC100913
0.8471 Intermediate Similarity NPC102465
0.8467 Intermediate Similarity NPC470158
0.8467 Intermediate Similarity NPC475933
0.8456 Intermediate Similarity NPC469742
0.8435 Intermediate Similarity NPC472572
0.8435 Intermediate Similarity NPC158663
0.8435 Intermediate Similarity NPC470157
0.8435 Intermediate Similarity NPC470159
0.8435 Intermediate Similarity NPC70403
0.8435 Intermediate Similarity NPC96903
0.8435 Intermediate Similarity NPC200471
0.8435 Intermediate Similarity NPC471162
0.8435 Intermediate Similarity NPC174982
0.8435 Intermediate Similarity NPC29704
0.8435 Intermediate Similarity NPC171525
0.8435 Intermediate Similarity NPC177940
0.8435 Intermediate Similarity NPC471104
0.8435 Intermediate Similarity NPC476973
0.8435 Intermediate Similarity NPC469349
0.8435 Intermediate Similarity NPC473088
0.8435 Intermediate Similarity NPC472568
0.8435 Intermediate Similarity NPC184817
0.8435 Intermediate Similarity NPC472575
0.8435 Intermediate Similarity NPC472571
0.8431 Intermediate Similarity NPC49297
0.8425 Intermediate Similarity NPC477894
0.8421 Intermediate Similarity NPC11410
0.8417 Intermediate Similarity NPC93632
0.8394 Intermediate Similarity NPC471758
0.8387 Intermediate Similarity NPC275477
0.8369 Intermediate Similarity NPC475493
0.8367 Intermediate Similarity NPC241951
0.8367 Intermediate Similarity NPC470152
0.8367 Intermediate Similarity NPC475759
0.8367 Intermediate Similarity NPC475122
0.8366 Intermediate Similarity NPC469417
0.8366 Intermediate Similarity NPC181924
0.8356 Intermediate Similarity NPC140021
0.8355 Intermediate Similarity NPC473632
0.8355 Intermediate Similarity NPC469730
0.8355 Intermediate Similarity NPC251139
0.8355 Intermediate Similarity NPC132599
0.8345 Intermediate Similarity NPC477904
0.8345 Intermediate Similarity NPC472547
0.8345 Intermediate Similarity NPC183270
0.8333 Intermediate Similarity NPC66193
0.8333 Intermediate Similarity NPC45821
0.8333 Intermediate Similarity NPC329960
0.8333 Intermediate Similarity NPC295408
0.8333 Intermediate Similarity NPC150893
0.8322 Intermediate Similarity NPC281717
0.8322 Intermediate Similarity NPC195647
0.8322 Intermediate Similarity NPC17877
0.8322 Intermediate Similarity NPC66761
0.8322 Intermediate Similarity NPC291638
0.8322 Intermediate Similarity NPC472577
0.8312 Intermediate Similarity NPC469399
0.8311 Intermediate Similarity NPC472556
0.8309 Intermediate Similarity NPC473889
0.8309 Intermediate Similarity NPC70973
0.8301 Intermediate Similarity NPC70344
0.8299 Intermediate Similarity NPC163087
0.8298 Intermediate Similarity NPC472361
0.8289 Intermediate Similarity NPC133430
0.8289 Intermediate Similarity NPC469477
0.8288 Intermediate Similarity NPC224491
0.828 Intermediate Similarity NPC471134
0.8269 Intermediate Similarity NPC43304
0.8269 Intermediate Similarity NPC165234
0.8269 Intermediate Similarity NPC475536
0.8269 Intermediate Similarity NPC477190
0.8269 Intermediate Similarity NPC477188
0.8267 Intermediate Similarity NPC471101
0.8267 Intermediate Similarity NPC270590
0.8267 Intermediate Similarity NPC266265
0.8267 Intermediate Similarity NPC92293

  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 NPC471912 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
0.831 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD8407 Phase 2
0.8049 Intermediate Similarity NPD8368 Discontinued
0.7917 Intermediate Similarity NPD8434 Phase 2
0.7914 Intermediate Similarity NPD7799 Discontinued
0.7829 Intermediate Similarity NPD7236 Approved
0.7824 Intermediate Similarity NPD8435 Approved
0.7719 Intermediate Similarity NPD8360 Approved
0.7719 Intermediate Similarity NPD8361 Approved
0.7692 Intermediate Similarity NPD7239 Suspended
0.7602 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD8485 Approved
0.75 Intermediate Similarity NPD7961 Discontinued
0.7442 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.743 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6190 Approved
0.7286 Intermediate Similarity NPD4198 Discontinued
0.7256 Intermediate Similarity NPD7058 Phase 2
0.7256 Intermediate Similarity NPD7057 Phase 3
0.72 Intermediate Similarity NPD8150 Discontinued
0.7135 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD8166 Discontinued
0.7134 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7075 Discontinued
0.7092 Intermediate Similarity NPD2629 Approved
0.709 Intermediate Similarity NPD8462 Phase 1
0.7055 Intermediate Similarity NPD6599 Discontinued
0.6982 Remote Similarity NPD8127 Discontinued
0.6981 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6978 Remote Similarity NPD2067 Discontinued
0.6957 Remote Similarity NPD5345 Clinical (unspecified phase)
0.695 Remote Similarity NPD6858 Approved
0.695 Remote Similarity NPD7094 Approved
0.6928 Remote Similarity NPD7819 Suspended
0.6919 Remote Similarity NPD7473 Discontinued
0.6901 Remote Similarity NPD6010 Discontinued
0.6897 Remote Similarity NPD7741 Discontinued
0.6897 Remote Similarity NPD6319 Approved
0.6886 Remote Similarity NPD3817 Phase 2
0.6867 Remote Similarity NPD37 Approved
0.6867 Remote Similarity NPD6801 Discontinued
0.6864 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6234 Discontinued
0.6856 Remote Similarity NPD8404 Phase 2
0.6845 Remote Similarity NPD4967 Phase 2
0.6845 Remote Similarity NPD4966 Approved
0.6845 Remote Similarity NPD4965 Approved
0.6815 Remote Similarity NPD7305 Phase 1
0.6813 Remote Similarity NPD4628 Phase 3
0.6812 Remote Similarity NPD5048 Discontinued
0.6809 Remote Similarity NPD8320 Phase 1
0.6809 Remote Similarity NPD8319 Approved
0.6802 Remote Similarity NPD7184 Clinical (unspecified phase)
0.68 Remote Similarity NPD7736 Approved
0.679 Remote Similarity NPD6799 Approved
0.6782 Remote Similarity NPD3751 Discontinued
0.6761 Remote Similarity NPD8297 Approved
0.6757 Remote Similarity NPD8328 Phase 3
0.6757 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6748 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6746 Remote Similarity NPD3882 Suspended
0.6744 Remote Similarity NPD6232 Discontinued
0.6744 Remote Similarity NPD3787 Discontinued
0.6736 Remote Similarity NPD690 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6355 Discontinued
0.6726 Remote Similarity NPD5760 Phase 2
0.6726 Remote Similarity NPD5761 Phase 2
0.6723 Remote Similarity NPD6765 Approved
0.6723 Remote Similarity NPD6764 Approved
0.6711 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6711 Remote Similarity NPD7492 Approved
0.669 Remote Similarity NPD3317 Approved
0.669 Remote Similarity NPD7115 Discovery
0.6689 Remote Similarity NPD5125 Phase 3
0.6689 Remote Similarity NPD5126 Approved
0.6686 Remote Similarity NPD7228 Approved
0.6686 Remote Similarity NPD5402 Approved
0.6667 Remote Similarity NPD6054 Approved
0.6667 Remote Similarity NPD6647 Phase 2
0.6667 Remote Similarity NPD7435 Discontinued
0.6667 Remote Similarity NPD6616 Approved
0.6667 Remote Similarity NPD7699 Phase 2
0.6667 Remote Similarity NPD7700 Phase 2
0.6648 Remote Similarity NPD8313 Approved
0.6648 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6648 Remote Similarity NPD8312 Approved
0.6648 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6647 Remote Similarity NPD4380 Phase 2
0.6647 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6646 Remote Similarity NPD2534 Approved
0.6646 Remote Similarity NPD2532 Approved
0.6646 Remote Similarity NPD2533 Approved
0.6645 Remote Similarity NPD7319 Approved
0.6645 Remote Similarity NPD3764 Approved
0.6628 Remote Similarity NPD5494 Approved
0.6623 Remote Similarity NPD7078 Approved
0.6605 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6603 Remote Similarity NPD6663 Approved
0.6599 Remote Similarity NPD7610 Discontinued
0.6595 Remote Similarity NPD6534 Approved
0.6595 Remote Similarity NPD6535 Approved
0.6591 Remote Similarity NPD3818 Discontinued
0.659 Remote Similarity NPD7199 Phase 2
0.6588 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6587 Remote Similarity NPD7458 Discontinued
0.6587 Remote Similarity NPD3226 Approved
0.6581 Remote Similarity NPD7008 Discontinued
0.6581 Remote Similarity NPD7095 Approved
0.6577 Remote Similarity NPD6370 Approved
0.6577 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6575 Remote Similarity NPD6784 Approved
0.6575 Remote Similarity NPD6785 Approved
0.6573 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6573 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6573 Remote Similarity NPD6649 Approved
0.6573 Remote Similarity NPD6650 Approved
0.6573 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6571 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6571 Remote Similarity NPD6166 Phase 2
0.6571 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6569 Remote Similarity NPD7798 Approved
0.6566 Remote Similarity NPD5403 Approved
0.6558 Remote Similarity NPD5736 Approved
0.6554 Remote Similarity NPD5844 Phase 1
0.6546 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6546 Remote Similarity NPD7874 Approved
0.6545 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6545 Remote Similarity NPD5401 Approved
0.6538 Remote Similarity NPD6798 Discontinued
0.6536 Remote Similarity NPD7240 Approved
0.6529 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6685 Approved
0.6522 Remote Similarity NPD5762 Approved
0.6522 Remote Similarity NPD5763 Approved
0.6513 Remote Similarity NPD8293 Discontinued
0.651 Remote Similarity NPD8513 Phase 3
0.651 Remote Similarity NPD8515 Approved
0.651 Remote Similarity NPD6016 Approved
0.651 Remote Similarity NPD8517 Approved
0.651 Remote Similarity NPD6921 Approved
0.651 Remote Similarity NPD8516 Approved
0.651 Remote Similarity NPD6015 Approved
0.6509 Remote Similarity NPD7411 Suspended
0.6507 Remote Similarity NPD5951 Approved
0.6503 Remote Similarity NPD5955 Clinical (unspecified phase)
0.65 Remote Similarity NPD5909 Discontinued
0.65 Remote Similarity NPD7808 Phase 3
0.65 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6497 Remote Similarity NPD6233 Phase 2
0.6496 Remote Similarity NPD4225 Approved
0.6485 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6483 Remote Similarity NPD4632 Approved
0.6479 Remote Similarity NPD6899 Approved
0.6479 Remote Similarity NPD6881 Approved
0.6471 Remote Similarity NPD1934 Approved
0.6467 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6467 Remote Similarity NPD5988 Approved
0.6463 Remote Similarity NPD8295 Clinical (unspecified phase)
0.646 Remote Similarity NPD6100 Approved
0.646 Remote Similarity NPD6099 Approved
0.6458 Remote Similarity NPD8130 Phase 1
0.6457 Remote Similarity NPD7229 Phase 3
0.6449 Remote Similarity NPD2066 Phase 3
0.6447 Remote Similarity NPD7507 Approved
0.6447 Remote Similarity NPD6637 Approved
0.6446 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6444 Remote Similarity NPD6559 Discontinued
0.6444 Remote Similarity NPD7251 Discontinued
0.6444 Remote Similarity NPD7685 Pre-registration
0.6443 Remote Similarity NPD6059 Approved
0.6442 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6434 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6434 Remote Similarity NPD6372 Approved
0.6434 Remote Similarity NPD6373 Approved
0.6421 Remote Similarity NPD6780 Approved
0.6421 Remote Similarity NPD6777 Approved
0.6421 Remote Similarity NPD6778 Approved
0.6421 Remote Similarity NPD6776 Approved
0.6421 Remote Similarity NPD6781 Approved
0.6421 Remote Similarity NPD6779 Approved
0.6421 Remote Similarity NPD6782 Approved
0.642 Remote Similarity NPD2346 Discontinued
0.642 Remote Similarity NPD7266 Discontinued
0.642 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6416 Remote Similarity NPD3749 Approved
0.6416 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6415 Remote Similarity NPD230 Phase 1
0.6414 Remote Similarity NPD6882 Approved
0.6408 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6408 Remote Similarity NPD5697 Approved
0.6407 Remote Similarity NPD6273 Approved
0.6406 Remote Similarity NPD7698 Approved
0.6406 Remote Similarity NPD7696 Phase 3
0.6406 Remote Similarity NPD7497 Discontinued
0.6406 Remote Similarity NPD7697 Approved
0.6402 Remote Similarity NPD2575 Approved
0.6398 Remote Similarity NPD7033 Discontinued
0.6392 Remote Similarity NPD8032 Phase 2

  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