Structure

Physi-Chem Properties

Molecular Weight:  704.23
Volume:  656.277
LogP:  0.651
LogD:  0.23
LogS:  -3.4
# Rotatable Bonds:  8
TPSA:  245.04
# H-Bond Aceptor:  16
# H-Bond Donor:  6
# Rings:  7
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.138
Synthetic Accessibility Score:  6.801
Fsp3:  0.647
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:  -6.091
MDCK Permeability:  0.0001754891563905403
Pgp-inhibitor:  0.944
Pgp-substrate:  0.988
Human Intestinal Absorption (HIA):  0.802
20% Bioavailability (F20%):  0.509
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.094
Plasma Protein Binding (PPB):  44.781822204589844%
Volume Distribution (VD):  0.681
Pgp-substrate:  17.29210090637207%

ADMET: Metabolism

CYP1A2-inhibitor:  0.011
CYP1A2-substrate:  0.103
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.197
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.017
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.075
CYP3A4-inhibitor:  0.168
CYP3A4-substrate:  0.083

ADMET: Excretion

Clearance (CL):  1.889
Half-life (T1/2):  0.493

ADMET: Toxicity

hERG Blockers:  0.293
Human Hepatotoxicity (H-HT):  0.525
Drug-inuced Liver Injury (DILI):  0.95
AMES Toxicity:  0.044
Rat Oral Acute Toxicity:  0.1
Maximum Recommended Daily Dose:  0.077
Skin Sensitization:  0.107
Carcinogencity:  0.056
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.313

Download Data

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

  Natural Product: NPC102465

Natural Product ID:  NPC102465
Common Name*:   Yadanzioside-M
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QHFGKHHBXLUOJV-ROCAPRSOSA-N
Standard InCHI:  InChI=1S/C34H40O16/c1-13-15-9-18-33-12-46-34(31(44)45-3,26(33)24(29(43)49-18)50-28(42)14-7-5-4-6-8-14)27(41)23(40)25(33)32(15,2)10-16(19(13)36)47-30-22(39)21(38)20(37)17(11-35)48-30/h4-8,10,13,15,17-18,20-27,30,35,37-41H,9,11-12H2,1-3H3/t13-,15-,17+,18+,20+,21-,22+,23+,24+,25+,26+,27-,30+,32-,33+,34-/m0/s1
SMILES:  OC[C@H]1O[C@@H](OC2=C[C@@]3(C)[C@H]([C@@H](C2=O)C)C[C@@H]2[C@@]45[C@@H]3[C@@H](O)[C@H](O)[C@]([C@@H]5[C@H](C(=O)O2)OC(=O)c2ccccc2)(OC4)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2368274
PubChem CID:   21115200
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0002119] Quassinoids

*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
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. seed n.a. DOI[10.1016/0031-9422(96)00258-0]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S1383-5769(99)00023-9]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[10086989]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[1512598]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[15165151]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[15949825]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota fruit Indonesia n.a. PMID[17896817]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[18723353]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. Vietnam n.a. PMID[19026551]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota seeds n.a. n.a. PMID[20050684]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[22506620]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[26522747]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6481366]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[7561896]
NPO211 Aplysina cauliformis Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[8350091]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12089 Trifolium alexandrinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11432 Centrolobium tomentosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12717 Parmelia metastrigosa Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9203 Cephalonomia gallicola Species Bethylidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26718 Chelidonura fulvipunctata Species Aglajidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO211 Aplysina cauliformis Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11084 Asplenium normale Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14749 Lippia carviodora Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14150 Solanum jamaicense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11637 Psilostrophe cooperi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5303 Castanea crenata Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12944 Sideritis tragoriganum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14528 Pneumatospora obcoronata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3164 Yponomeuta malinellus Species Yponomeutidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14845 Ceratophyllum submersum Species Ceratophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10818 Carpobrotus edulis Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1641 Amycolatopsis azurea Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12089 Trifolium alexandrinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11873 Oecophylla smaragdina Species Formicidae 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
NPT759 Cell Line H9 Homo sapiens IC50 = 7000.0 nM PMID[515221]

☑ 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 NPC102465 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
0.949 High Similarity NPC150893
0.949 High Similarity NPC329960
0.949 High Similarity NPC295408
0.9295 High Similarity NPC477735
0.9236 High Similarity NPC477736
0.9198 High Similarity NPC477473
0.9198 High Similarity NPC477466
0.9198 High Similarity NPC477471
0.9198 High Similarity NPC477469
0.9167 High Similarity NPC472549
0.9097 High Similarity NPC306799
0.9097 High Similarity NPC101043
0.9068 High Similarity NPC471493
0.9051 High Similarity NPC469417
0.9038 High Similarity NPC472548
0.9018 High Similarity NPC469420
0.8994 High Similarity NPC469399
0.8987 High Similarity NPC106895
0.8981 High Similarity NPC69425
0.8974 High Similarity NPC51602
0.8974 High Similarity NPC471103
0.8924 High Similarity NPC282239
0.8924 High Similarity NPC21410
0.8924 High Similarity NPC473670
0.8924 High Similarity NPC5115
0.8917 High Similarity NPC477905
0.8916 High Similarity NPC469421
0.891 High Similarity NPC7095
0.8875 High Similarity NPC471102
0.8868 High Similarity NPC217091
0.8861 High Similarity NPC257213
0.8861 High Similarity NPC158333
0.8861 High Similarity NPC265395
0.8861 High Similarity NPC133430
0.8861 High Similarity NPC472005
0.8861 High Similarity NPC249471
0.8861 High Similarity NPC256142
0.8861 High Similarity NPC237549
0.8861 High Similarity NPC242262
0.8861 High Similarity NPC472030
0.8861 High Similarity NPC1173
0.8861 High Similarity NPC304876
0.8861 High Similarity NPC472022
0.8861 High Similarity NPC473414
0.8861 High Similarity NPC469477
0.8854 High Similarity NPC329657
0.8846 High Similarity NPC81698
0.8846 High Similarity NPC60509
0.8846 High Similarity NPC250046
0.8839 High Similarity NPC477737
0.8812 High Similarity NPC472393
0.8805 High Similarity NPC228204
0.8805 High Similarity NPC26033
0.8805 High Similarity NPC112523
0.8805 High Similarity NPC114410
0.879 High Similarity NPC165260
0.879 High Similarity NPC161239
0.879 High Similarity NPC112216
0.879 High Similarity NPC198455
0.878 High Similarity NPC477491
0.8774 High Similarity NPC127857
0.8773 High Similarity NPC66193
0.8758 High Similarity NPC476784
0.8758 High Similarity NPC477467
0.8742 High Similarity NPC77719
0.8735 High Similarity NPC477488
0.872 High Similarity NPC471134
0.8704 High Similarity NPC477623
0.8696 High Similarity NPC477470
0.8696 High Similarity NPC469771
0.8696 High Similarity NPC477474
0.8696 High Similarity NPC477472
0.8671 High Similarity NPC469448
0.8671 High Similarity NPC473214
0.8671 High Similarity NPC254558
0.8671 High Similarity NPC470245
0.8667 High Similarity NPC61891
0.8654 High Similarity NPC471107
0.8654 High Similarity NPC471100
0.8625 High Similarity NPC219419
0.8623 High Similarity NPC469419
0.8616 High Similarity NPC470153
0.8608 High Similarity NPC473215
0.8608 High Similarity NPC476975
0.8599 High Similarity NPC469513
0.8598 High Similarity NPC43304
0.8598 High Similarity NPC475536
0.8598 High Similarity NPC165234
0.8598 High Similarity NPC477188
0.8598 High Similarity NPC477190
0.8581 High Similarity NPC182869
0.8571 High Similarity NPC469398
0.8571 High Similarity NPC259144
0.8571 High Similarity NPC34066
0.8571 High Similarity NPC114357
0.8571 High Similarity NPC469422
0.8571 High Similarity NPC155329
0.8563 High Similarity NPC40138
0.8554 High Similarity NPC475567
0.8554 High Similarity NPC473468
0.8554 High Similarity NPC473557
0.8545 High Similarity NPC475464
0.8545 High Similarity NPC473641
0.8545 High Similarity NPC475300
0.8545 High Similarity NPC475437
0.8545 High Similarity NPC475505
0.8545 High Similarity NPC322420
0.8545 High Similarity NPC473797
0.8535 High Similarity NPC301946
0.8535 High Similarity NPC277053
0.8529 High Similarity NPC477617
0.8516 High Similarity NPC77493
0.8509 High Similarity NPC248265
0.8509 High Similarity NPC229545
0.8509 High Similarity NPC11588
0.8509 High Similarity NPC134685
0.8503 High Similarity NPC475531
0.8503 High Similarity NPC475175
0.8503 High Similarity NPC475198
0.85 High Similarity NPC469415
0.8494 Intermediate Similarity NPC477627
0.8485 Intermediate Similarity NPC275477
0.848 Intermediate Similarity NPC124828
0.848 Intermediate Similarity NPC195972
0.8471 Intermediate Similarity NPC80895
0.8471 Intermediate Similarity NPC471912
0.8462 Intermediate Similarity NPC472546
0.8457 Intermediate Similarity NPC473611
0.8457 Intermediate Similarity NPC473632
0.8457 Intermediate Similarity NPC469730
0.8457 Intermediate Similarity NPC132599
0.8452 Intermediate Similarity NPC183270
0.8452 Intermediate Similarity NPC477904
0.8443 Intermediate Similarity NPC324769
0.8443 Intermediate Similarity NPC325732
0.8438 Intermediate Similarity NPC91730
0.8438 Intermediate Similarity NPC222102
0.8438 Intermediate Similarity NPC303429
0.8434 Intermediate Similarity NPC478073
0.8421 Intermediate Similarity NPC13989
0.8418 Intermediate Similarity NPC470157
0.8418 Intermediate Similarity NPC158663
0.8418 Intermediate Similarity NPC70403
0.8418 Intermediate Similarity NPC470159
0.8418 Intermediate Similarity NPC96903
0.8418 Intermediate Similarity NPC174982
0.8418 Intermediate Similarity NPC171525
0.8418 Intermediate Similarity NPC177940
0.8418 Intermediate Similarity NPC476973
0.8418 Intermediate Similarity NPC469349
0.8418 Intermediate Similarity NPC184817
0.8418 Intermediate Similarity NPC471104
0.8418 Intermediate Similarity NPC29704
0.8418 Intermediate Similarity NPC473088
0.8418 Intermediate Similarity NPC200471
0.8418 Intermediate Similarity NPC472575
0.8418 Intermediate Similarity NPC472568
0.8418 Intermediate Similarity NPC472571
0.8418 Intermediate Similarity NPC472572
0.8415 Intermediate Similarity NPC49297
0.8409 Intermediate Similarity NPC96194
0.8409 Intermediate Similarity NPC299855
0.8397 Intermediate Similarity NPC27377
0.8397 Intermediate Similarity NPC97947
0.8397 Intermediate Similarity NPC41481
0.8397 Intermediate Similarity NPC16912
0.8397 Intermediate Similarity NPC472576
0.8397 Intermediate Similarity NPC291599
0.8397 Intermediate Similarity NPC118080
0.8397 Intermediate Similarity NPC87448
0.8395 Intermediate Similarity NPC472657
0.8395 Intermediate Similarity NPC472658
0.8385 Intermediate Similarity NPC197037
0.8382 Intermediate Similarity NPC475613
0.8375 Intermediate Similarity NPC301556
0.8375 Intermediate Similarity NPC92293
0.8375 Intermediate Similarity NPC471101
0.8375 Intermediate Similarity NPC270590
0.8375 Intermediate Similarity NPC266265
0.8365 Intermediate Similarity NPC474935
0.8362 Intermediate Similarity NPC189704
0.8354 Intermediate Similarity NPC475122
0.8354 Intermediate Similarity NPC188865
0.8354 Intermediate Similarity NPC470152
0.8354 Intermediate Similarity NPC476974
0.8354 Intermediate Similarity NPC470231
0.8354 Intermediate Similarity NPC472573
0.8354 Intermediate Similarity NPC11685
0.8354 Intermediate Similarity NPC95810
0.8354 Intermediate Similarity NPC95265
0.8354 Intermediate Similarity NPC25768
0.8354 Intermediate Similarity NPC472569
0.8354 Intermediate Similarity NPC57628
0.8354 Intermediate Similarity NPC125106
0.8354 Intermediate Similarity NPC475759
0.8354 Intermediate Similarity NPC241951
0.8354 Intermediate Similarity NPC70716
0.8354 Intermediate Similarity NPC163719
0.8354 Intermediate Similarity NPC472570
0.8354 Intermediate Similarity NPC181924

  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 NPC102465 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
0.8571 High Similarity NPD7799 Discontinued
0.8333 Intermediate Similarity NPD8407 Phase 2
0.8266 Intermediate Similarity NPD8368 Discontinued
0.8136 Intermediate Similarity NPD8434 Phase 2
0.8056 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD7236 Approved
0.7949 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7944 Intermediate Similarity NPD8435 Approved
0.7845 Intermediate Similarity NPD8360 Approved
0.7845 Intermediate Similarity NPD8361 Approved
0.7831 Intermediate Similarity NPD7239 Suspended
0.7778 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD8312 Approved
0.7765 Intermediate Similarity NPD8313 Approved
0.7754 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD8320 Phase 1
0.7684 Intermediate Similarity NPD8319 Approved
0.7684 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7637 Intermediate Similarity NPD8150 Discontinued
0.7611 Intermediate Similarity NPD7808 Phase 3
0.7594 Intermediate Similarity NPD8485 Approved
0.7556 Intermediate Similarity NPD7251 Discontinued
0.7553 Intermediate Similarity NPD7699 Phase 2
0.7553 Intermediate Similarity NPD7700 Phase 2
0.7539 Intermediate Similarity NPD7435 Discontinued
0.75 Intermediate Similarity NPD6797 Phase 2
0.743 Intermediate Similarity NPD7228 Approved
0.7414 Intermediate Similarity NPD7058 Phase 2
0.7414 Intermediate Similarity NPD7057 Phase 3
0.7398 Intermediate Similarity NPD7874 Approved
0.7398 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD6535 Approved
0.7394 Intermediate Similarity NPD6534 Approved
0.7363 Intermediate Similarity NPD7240 Approved
0.7358 Intermediate Similarity NPD7698 Approved
0.7358 Intermediate Similarity NPD7696 Phase 3
0.7358 Intermediate Similarity NPD7697 Approved
0.7348 Intermediate Similarity NPD7074 Phase 3
0.7348 Intermediate Similarity NPD7472 Approved
0.7333 Intermediate Similarity NPD3751 Discontinued
0.7322 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD8455 Phase 2
0.7296 Intermediate Similarity NPD7701 Phase 2
0.7293 Intermediate Similarity NPD7054 Approved
0.7292 Intermediate Similarity NPD6781 Approved
0.7292 Intermediate Similarity NPD6777 Approved
0.7292 Intermediate Similarity NPD6776 Approved
0.7292 Intermediate Similarity NPD6782 Approved
0.7292 Intermediate Similarity NPD6778 Approved
0.7292 Intermediate Similarity NPD6779 Approved
0.7292 Intermediate Similarity NPD6780 Approved
0.7273 Intermediate Similarity NPD7075 Discontinued
0.7273 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD7685 Pre-registration
0.7267 Intermediate Similarity NPD7458 Discontinued
0.7259 Intermediate Similarity NPD8151 Discontinued
0.7238 Intermediate Similarity NPD3818 Discontinued
0.7232 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD7871 Phase 2
0.7231 Intermediate Similarity NPD7870 Phase 2
0.7213 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD3787 Discontinued
0.7186 Intermediate Similarity NPD7801 Approved
0.7179 Intermediate Similarity NPD8328 Phase 3
0.7178 Intermediate Similarity NPD8404 Phase 2
0.7174 Intermediate Similarity NPD6559 Discontinued
0.715 Intermediate Similarity NPD8462 Phase 1
0.7143 Intermediate Similarity NPD37 Approved
0.7135 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD6166 Phase 2
0.7126 Intermediate Similarity NPD6599 Discontinued
0.7119 Intermediate Similarity NPD4965 Approved
0.7119 Intermediate Similarity NPD4967 Phase 2
0.7119 Intermediate Similarity NPD4966 Approved
0.7102 Intermediate Similarity NPD7819 Suspended
0.7081 Intermediate Similarity NPD6764 Approved
0.7081 Intermediate Similarity NPD6765 Approved
0.7059 Intermediate Similarity NPD6190 Approved
0.7045 Intermediate Similarity NPD6801 Discontinued
0.7039 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD6234 Discontinued
0.7029 Intermediate Similarity NPD4380 Phase 2
0.7012 Intermediate Similarity NPD7961 Discontinued
0.7 Intermediate Similarity NPD5494 Approved
0.7 Intermediate Similarity NPD8166 Discontinued
0.7 Intermediate Similarity NPD4628 Phase 3
0.6995 Remote Similarity NPD7473 Discontinued
0.6978 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6971 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6966 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6966 Remote Similarity NPD3817 Phase 2
0.6966 Remote Similarity NPD5402 Approved
0.6961 Remote Similarity NPD8127 Discontinued
0.6954 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6954 Remote Similarity NPD6823 Phase 2
0.6931 Remote Similarity NPD6785 Approved
0.6931 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6931 Remote Similarity NPD6784 Approved
0.6931 Remote Similarity NPD7783 Phase 2
0.6927 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7266 Discontinued
0.6919 Remote Similarity NPD5844 Phase 1
0.691 Remote Similarity NPD5761 Phase 2
0.691 Remote Similarity NPD5760 Phase 2
0.6893 Remote Similarity NPD7411 Suspended
0.6891 Remote Similarity NPD6212 Phase 3
0.6891 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6891 Remote Similarity NPD6213 Phase 3
0.6879 Remote Similarity NPD6799 Approved
0.6868 Remote Similarity NPD7199 Phase 2
0.6857 Remote Similarity NPD5403 Approved
0.685 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6848 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6839 Remote Similarity NPD5401 Approved
0.6835 Remote Similarity NPD8516 Approved
0.6835 Remote Similarity NPD8517 Approved
0.6835 Remote Similarity NPD8515 Approved
0.6835 Remote Similarity NPD8513 Phase 3
0.6833 Remote Similarity NPD3882 Suspended
0.6831 Remote Similarity NPD6232 Discontinued
0.681 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6795 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6795 Remote Similarity NPD4198 Discontinued
0.6792 Remote Similarity NPD5125 Phase 3
0.6792 Remote Similarity NPD5126 Approved
0.6792 Remote Similarity NPD3412 Clinical (unspecified phase)
0.679 Remote Similarity NPD7736 Approved
0.6782 Remote Similarity NPD6143 Clinical (unspecified phase)
0.678 Remote Similarity NPD3226 Approved
0.6776 Remote Similarity NPD6959 Discontinued
0.675 Remote Similarity NPD7497 Discontinued
0.675 Remote Similarity NPD7680 Approved
0.6743 Remote Similarity NPD2532 Approved
0.6743 Remote Similarity NPD2534 Approved
0.6743 Remote Similarity NPD2533 Approved
0.6743 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6731 Remote Similarity NPD2629 Approved
0.6722 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6717 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6273 Approved
0.6703 Remote Similarity NPD3749 Approved
0.6667 Remote Similarity NPD1934 Approved
0.6648 Remote Similarity NPD7028 Phase 2
0.6647 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6647 Remote Similarity NPD7097 Phase 1
0.6647 Remote Similarity NPD3764 Approved
0.6646 Remote Similarity NPD7319 Approved
0.6628 Remote Similarity NPD2346 Discontinued
0.6624 Remote Similarity NPD690 Clinical (unspecified phase)
0.6609 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6601 Remote Similarity NPD7999 Approved
0.6587 Remote Similarity NPD7930 Approved
0.6587 Remote Similarity NPD7008 Discontinued
0.6562 Remote Similarity NPD7741 Discontinued
0.6558 Remote Similarity NPD8059 Phase 3
0.6558 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6557 Remote Similarity NPD7768 Phase 2
0.6554 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6554 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6552 Remote Similarity NPD6674 Discontinued
0.655 Remote Similarity NPD8285 Discontinued
0.6538 Remote Similarity NPD1465 Phase 2
0.6533 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6532 Remote Similarity NPD1471 Phase 3
0.6532 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6529 Remote Similarity NPD6355 Discontinued
0.6522 Remote Similarity NPD7503 Approved
0.6514 Remote Similarity NPD7003 Approved
0.6514 Remote Similarity NPD1878 Clinical (unspecified phase)
0.65 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6486 Remote Similarity NPD919 Approved
0.6481 Remote Similarity NPD6370 Approved
0.6479 Remote Similarity NPD7907 Approved
0.6474 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6463 Remote Similarity NPD7507 Approved
0.6457 Remote Similarity NPD2800 Approved
0.6448 Remote Similarity NPD2801 Approved
0.6442 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6437 Remote Similarity NPD5763 Approved
0.6437 Remote Similarity NPD5762 Approved
0.6433 Remote Similarity NPD969 Suspended
0.6433 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6433 Remote Similarity NPD230 Phase 1
0.6424 Remote Similarity NPD8293 Discontinued
0.642 Remote Similarity NPD3750 Approved
0.6417 Remote Similarity NPD1247 Approved
0.6416 Remote Similarity NPD2799 Discontinued
0.641 Remote Similarity NPD2067 Discontinued
0.6409 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6408 Remote Similarity NPD7584 Approved
0.6402 Remote Similarity NPD7492 Approved
0.6402 Remote Similarity NPD8366 Approved
0.64 Remote Similarity NPD1549 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