Structure

Physi-Chem Properties

Molecular Weight:  566.24
Volume:  542.362
LogP:  1.033
LogD:  0.125
LogS:  -3.011
# Rotatable Bonds:  6
TPSA:  189.28
# H-Bond Aceptor:  12
# H-Bond Donor:  5
# Rings:  5
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.123
Synthetic Accessibility Score:  6.803
Fsp3:  0.75
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:  -5.621
MDCK Permeability:  0.00012562285701278597
Pgp-inhibitor:  0.989
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.914
20% Bioavailability (F20%):  0.475
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.103
Plasma Protein Binding (PPB):  32.16447067260742%
Volume Distribution (VD):  0.411
Pgp-substrate:  40.41945266723633%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.704
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.478
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.023
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.104
CYP3A4-inhibitor:  0.043
CYP3A4-substrate:  0.14

ADMET: Excretion

Clearance (CL):  2.202
Half-life (T1/2):  0.638

ADMET: Toxicity

hERG Blockers:  0.06
Human Hepatotoxicity (H-HT):  0.686
Drug-inuced Liver Injury (DILI):  0.527
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.4
Maximum Recommended Daily Dose:  0.183
Skin Sensitization:  0.184
Carcinogencity:  0.054
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.975

Download Data

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

  Natural Product: NPC67251

Natural Product ID:  NPC67251
Common Name*:   Javanicolide D
IUPAC Name:   n.a.
Synonyms:   Javanicolide D
Standard InCHIKey:  BYOUNBVBMRXOLD-PVSFWKLVSA-N
Standard InCHI:  InChI=1S/C28H38O12/c1-11-7-14(29)21(32)26(5)13(11)9-15-27-10-38-28(24(35)37-6,22(33)17(31)19(26)27)20(27)18(23(34)39-15)40-16(30)8-12(2)25(3,4)36/h7-8,13-15,17-22,29,31-33,36H,9-10H2,1-6H3/b12-8+/t13-,14-,15+,17+,18+,19+,20+,21+,22-,26-,27+,28-/m0/s1
SMILES:  COC(=O)[C@@]12OC[C@]34[C@H]2[C@@H](OC(=O)/C=C(/C(O)(C)C)C)C(=O)O[C@@H]4C[C@@H]2[C@]([C@H]3[C@H]([C@@H]1O)O)(C)[C@H](O)[C@@H](O)C=C2C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL503843
PubChem CID:   11455840
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]
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]
NPO12089 Trifolium alexandrinum Species Fabaceae 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]
NPO12944 Sideritis tragoriganum 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]
NPO3164 Yponomeuta malinellus Species Yponomeutidae 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]
NPO10818 Carpobrotus edulis Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14845 Ceratophyllum submersum Species Ceratophyllaceae 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]
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]
NPO11084 Asplenium normale Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14150 Solanum jamaicense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14749 Lippia carviodora Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11637 Psilostrophe cooperi Species Asteraceae 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
NPT168 Cell Line P388 Mus musculus IC50 = 18.0 ug.mL-1 PMID[555745]

☑ 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 NPC67251 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
0.9739 High Similarity NPC476729
0.9652 High Similarity NPC18945
0.9652 High Similarity NPC105926
0.9652 High Similarity NPC91693
0.9652 High Similarity NPC265557
0.9569 High Similarity NPC24651
0.9565 High Similarity NPC312833
0.9558 High Similarity NPC470776
0.9478 High Similarity NPC470779
0.9469 High Similarity NPC473590
0.9402 High Similarity NPC470922
0.9386 High Similarity NPC17772
0.9381 High Similarity NPC474734
0.9298 High Similarity NPC470775
0.9298 High Similarity NPC176513
0.9244 High Similarity NPC476008
0.9217 High Similarity NPC251310
0.9211 High Similarity NPC328374
0.9211 High Similarity NPC96312
0.9211 High Similarity NPC40632
0.9211 High Similarity NPC251236
0.9211 High Similarity NPC89929
0.9204 High Similarity NPC94509
0.916 High Similarity NPC477745
0.9138 High Similarity NPC470777
0.913 High Similarity NPC470854
0.913 High Similarity NPC287343
0.913 High Similarity NPC474654
0.913 High Similarity NPC470778
0.913 High Similarity NPC146432
0.913 High Similarity NPC97908
0.913 High Similarity NPC122033
0.9123 High Similarity NPC473798
0.906 High Similarity NPC112038
0.906 High Similarity NPC109607
0.906 High Similarity NPC107338
0.9052 High Similarity NPC297179
0.9043 High Similarity NPC259306
0.9043 High Similarity NPC16081
0.9043 High Similarity NPC173686
0.9043 High Similarity NPC474046
0.9043 High Similarity NPC213084
0.9043 High Similarity NPC190185
0.9043 High Similarity NPC470628
0.9035 High Similarity NPC49451
0.8974 High Similarity NPC476529
0.8974 High Similarity NPC475775
0.8966 High Similarity NPC473968
0.896 High Similarity NPC251998
0.8957 High Similarity NPC323821
0.8957 High Similarity NPC469877
0.8957 High Similarity NPC45218
0.8957 High Similarity NPC268238
0.8957 High Similarity NPC470919
0.8957 High Similarity NPC143268
0.8957 High Similarity NPC299849
0.8947 High Similarity NPC269530
0.8926 High Similarity NPC470780
0.8889 High Similarity NPC140045
0.8889 High Similarity NPC204552
0.8889 High Similarity NPC188667
0.8889 High Similarity NPC596
0.8889 High Similarity NPC295885
0.888 High Similarity NPC262813
0.8879 High Similarity NPC134869
0.8879 High Similarity NPC235539
0.8879 High Similarity NPC152199
0.8871 High Similarity NPC168879
0.887 High Similarity NPC208998
0.887 High Similarity NPC7921
0.8824 High Similarity NPC477046
0.8824 High Similarity NPC102822
0.881 High Similarity NPC141215
0.881 High Similarity NPC471089
0.881 High Similarity NPC190065
0.8803 High Similarity NPC469684
0.8793 High Similarity NPC18547
0.8793 High Similarity NPC474906
0.879 High Similarity NPC102316
0.8783 High Similarity NPC302146
0.875 High Similarity NPC269642
0.872 High Similarity NPC478151
0.8718 High Similarity NPC207217
0.871 High Similarity NPC301639
0.871 High Similarity NPC45346
0.871 High Similarity NPC475377
0.871 High Similarity NPC478065
0.871 High Similarity NPC475167
0.871 High Similarity NPC173435
0.871 High Similarity NPC134914
0.871 High Similarity NPC262796
0.871 High Similarity NPC172374
0.871 High Similarity NPC478064
0.871 High Similarity NPC329993
0.871 High Similarity NPC476074
0.871 High Similarity NPC264566
0.8707 High Similarity NPC51978
0.8707 High Similarity NPC477126
0.8696 High Similarity NPC171888
0.8696 High Similarity NPC146945
0.8689 High Similarity NPC181999
0.8689 High Similarity NPC293112
0.8655 High Similarity NPC469488
0.8655 High Similarity NPC77689
0.8655 High Similarity NPC473636
0.8644 High Similarity NPC134430
0.8644 High Similarity NPC58662
0.8644 High Similarity NPC53396
0.8644 High Similarity NPC98249
0.864 High Similarity NPC478150
0.864 High Similarity NPC478153
0.864 High Similarity NPC478154
0.864 High Similarity NPC478152
0.8632 High Similarity NPC117712
0.8629 High Similarity NPC476851
0.8621 High Similarity NPC474516
0.8621 High Similarity NPC472002
0.8621 High Similarity NPC317687
0.8621 High Similarity NPC11252
0.8621 High Similarity NPC289312
0.8618 High Similarity NPC470882
0.8609 High Similarity NPC5103
0.8607 High Similarity NPC81736
0.8607 High Similarity NPC172154
0.8596 High Similarity NPC293850
0.8595 High Similarity NPC222688
0.8571 High Similarity NPC284707
0.856 High Similarity NPC476852
0.856 High Similarity NPC477197
0.856 High Similarity NPC25998
0.856 High Similarity NPC478155
0.8559 High Similarity NPC179626
0.8548 High Similarity NPC188291
0.8548 High Similarity NPC476859
0.8548 High Similarity NPC329923
0.8548 High Similarity NPC477075
0.8548 High Similarity NPC475281
0.8548 High Similarity NPC477078
0.8547 High Similarity NPC469496
0.8547 High Similarity NPC469454
0.8547 High Similarity NPC469463
0.8547 High Similarity NPC25909
0.8537 High Similarity NPC225049
0.8537 High Similarity NPC473635
0.8534 High Similarity NPC469656
0.8534 High Similarity NPC474846
0.8534 High Similarity NPC157476
0.8534 High Similarity NPC201992
0.8534 High Similarity NPC317107
0.8534 High Similarity NPC469655
0.8525 High Similarity NPC469789
0.8525 High Similarity NPC11895
0.8522 High Similarity NPC143706
0.8522 High Similarity NPC141350
0.8522 High Similarity NPC42662
0.8522 High Similarity NPC472534
0.8516 High Similarity NPC243014
0.8512 High Similarity NPC4021
0.8512 High Similarity NPC159456
0.8509 High Similarity NPC144854
0.8509 High Similarity NPC67321
0.8509 High Similarity NPC3316
0.8509 High Similarity NPC187435
0.85 High Similarity NPC473839
0.85 High Similarity NPC122971
0.85 High Similarity NPC230513
0.85 High Similarity NPC211093
0.85 High Similarity NPC475041
0.85 High Similarity NPC268958
0.8496 Intermediate Similarity NPC258532
0.8492 Intermediate Similarity NPC100390
0.8492 Intermediate Similarity NPC254614
0.8492 Intermediate Similarity NPC476193
0.8487 Intermediate Similarity NPC27999
0.8487 Intermediate Similarity NPC55296
0.8487 Intermediate Similarity NPC477116
0.8487 Intermediate Similarity NPC475809
0.8487 Intermediate Similarity NPC476713
0.8487 Intermediate Similarity NPC476712
0.848 Intermediate Similarity NPC470912
0.848 Intermediate Similarity NPC476854
0.848 Intermediate Similarity NPC470913
0.848 Intermediate Similarity NPC477077
0.848 Intermediate Similarity NPC477196
0.848 Intermediate Similarity NPC477076
0.848 Intermediate Similarity NPC231529
0.848 Intermediate Similarity NPC477079
0.8468 Intermediate Similarity NPC473265
0.8462 Intermediate Similarity NPC473877
0.8455 Intermediate Similarity NPC8369
0.8443 Intermediate Similarity NPC470265
0.8443 Intermediate Similarity NPC23786
0.8443 Intermediate Similarity NPC170538
0.8435 Intermediate Similarity NPC275539
0.8435 Intermediate Similarity NPC154608
0.8435 Intermediate Similarity NPC192813
0.8435 Intermediate Similarity NPC189075
0.8435 Intermediate Similarity NPC277017
0.843 Intermediate Similarity NPC251226
0.843 Intermediate Similarity NPC478051

  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 NPC67251 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
0.8276 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.808 Intermediate Similarity NPD8328 Phase 3
0.8047 Intermediate Similarity NPD7319 Approved
0.8033 Intermediate Similarity NPD7115 Discovery
0.7984 Intermediate Similarity NPD6319 Approved
0.7899 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD4225 Approved
0.7886 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD7507 Approved
0.7778 Intermediate Similarity NPD8513 Phase 3
0.7778 Intermediate Similarity NPD8516 Approved
0.7778 Intermediate Similarity NPD8515 Approved
0.7778 Intermediate Similarity NPD8517 Approved
0.775 Intermediate Similarity NPD6372 Approved
0.775 Intermediate Similarity NPD6373 Approved
0.7734 Intermediate Similarity NPD7492 Approved
0.7705 Intermediate Similarity NPD8297 Approved
0.7698 Intermediate Similarity NPD6059 Approved
0.7698 Intermediate Similarity NPD6054 Approved
0.7692 Intermediate Similarity NPD7736 Approved
0.7674 Intermediate Similarity NPD6616 Approved
0.7667 Intermediate Similarity NPD6686 Approved
0.7647 Intermediate Similarity NPD6675 Approved
0.7647 Intermediate Similarity NPD5739 Approved
0.7647 Intermediate Similarity NPD6402 Approved
0.7647 Intermediate Similarity NPD7128 Approved
0.7638 Intermediate Similarity NPD6921 Approved
0.7623 Intermediate Similarity NPD6649 Approved
0.7623 Intermediate Similarity NPD6650 Approved
0.7615 Intermediate Similarity NPD8293 Discontinued
0.7615 Intermediate Similarity NPD7078 Approved
0.7583 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD6370 Approved
0.7521 Intermediate Similarity NPD7640 Approved
0.7521 Intermediate Similarity NPD7639 Approved
0.7521 Intermediate Similarity NPD6899 Approved
0.7521 Intermediate Similarity NPD6881 Approved
0.7521 Intermediate Similarity NPD7320 Approved
0.75 Intermediate Similarity NPD4632 Approved
0.75 Intermediate Similarity NPD6016 Approved
0.75 Intermediate Similarity NPD6015 Approved
0.748 Intermediate Similarity NPD7516 Approved
0.7442 Intermediate Similarity NPD5988 Approved
0.7438 Intermediate Similarity NPD5701 Approved
0.7438 Intermediate Similarity NPD5697 Approved
0.7436 Intermediate Similarity NPD7638 Approved
0.7419 Intermediate Similarity NPD6882 Approved
0.7402 Intermediate Similarity NPD7328 Approved
0.7402 Intermediate Similarity NPD7327 Approved
0.7398 Intermediate Similarity NPD6883 Approved
0.7398 Intermediate Similarity NPD7102 Approved
0.7398 Intermediate Similarity NPD7290 Approved
0.7348 Intermediate Similarity NPD8074 Phase 3
0.7339 Intermediate Similarity NPD6869 Approved
0.7339 Intermediate Similarity NPD8130 Phase 1
0.7339 Intermediate Similarity NPD6617 Approved
0.7339 Intermediate Similarity NPD6847 Approved
0.7339 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD6009 Approved
0.7317 Intermediate Similarity NPD6012 Approved
0.7317 Intermediate Similarity NPD6013 Approved
0.7317 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD6014 Approved
0.7295 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD4634 Approved
0.7252 Intermediate Similarity NPD7604 Phase 2
0.7236 Intermediate Similarity NPD6011 Approved
0.7231 Intermediate Similarity NPD5983 Phase 2
0.7231 Intermediate Similarity NPD8378 Approved
0.7231 Intermediate Similarity NPD8380 Approved
0.7231 Intermediate Similarity NPD8335 Approved
0.7231 Intermediate Similarity NPD8033 Approved
0.7231 Intermediate Similarity NPD8379 Approved
0.7231 Intermediate Similarity NPD8296 Approved
0.7213 Intermediate Similarity NPD6008 Approved
0.72 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD5344 Discontinued
0.7164 Intermediate Similarity NPD6033 Approved
0.7154 Intermediate Similarity NPD8294 Approved
0.7154 Intermediate Similarity NPD6412 Phase 2
0.7154 Intermediate Similarity NPD8377 Approved
0.7143 Intermediate Similarity NPD6336 Discontinued
0.7132 Intermediate Similarity NPD7260 Phase 2
0.713 Intermediate Similarity NPD46 Approved
0.713 Intermediate Similarity NPD6698 Approved
0.712 Intermediate Similarity NPD6371 Approved
0.7107 Intermediate Similarity NPD5211 Phase 2
0.7099 Intermediate Similarity NPD7503 Approved
0.7087 Intermediate Similarity NPD8133 Approved
0.7059 Intermediate Similarity NPD6084 Phase 2
0.7059 Intermediate Similarity NPD6083 Phase 2
0.7059 Intermediate Similarity NPD7902 Approved
0.7059 Intermediate Similarity NPD4755 Approved
0.7009 Intermediate Similarity NPD5778 Approved
0.7009 Intermediate Similarity NPD5779 Approved
0.7008 Intermediate Similarity NPD6053 Discontinued
0.7 Intermediate Similarity NPD5696 Approved
0.6992 Remote Similarity NPD5141 Approved
0.6977 Remote Similarity NPD6274 Approved
0.6967 Remote Similarity NPD7632 Discontinued
0.6957 Remote Similarity NPD6845 Suspended
0.6949 Remote Similarity NPD7748 Approved
0.6947 Remote Similarity NPD7100 Approved
0.6947 Remote Similarity NPD7101 Approved
0.6942 Remote Similarity NPD4700 Approved
0.6942 Remote Similarity NPD4696 Approved
0.6942 Remote Similarity NPD5285 Approved
0.6942 Remote Similarity NPD5286 Approved
0.6923 Remote Similarity NPD6411 Approved
0.6923 Remote Similarity NPD7515 Phase 2
0.6923 Remote Similarity NPD7983 Approved
0.6879 Remote Similarity NPD7966 Clinical (unspecified phase)
0.687 Remote Similarity NPD6335 Approved
0.6864 Remote Similarity NPD6399 Phase 3
0.6842 Remote Similarity NPD6909 Approved
0.6842 Remote Similarity NPD6908 Approved
0.6833 Remote Similarity NPD4697 Phase 3
0.6829 Remote Similarity NPD5225 Approved
0.6829 Remote Similarity NPD5224 Approved
0.6829 Remote Similarity NPD4633 Approved
0.6829 Remote Similarity NPD5226 Approved
0.6807 Remote Similarity NPD5282 Discontinued
0.6807 Remote Similarity NPD7900 Approved
0.6807 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6803 Remote Similarity NPD6648 Approved
0.68 Remote Similarity NPD4767 Approved
0.68 Remote Similarity NPD4768 Approved
0.6794 Remote Similarity NPD6317 Approved
0.6774 Remote Similarity NPD5174 Approved
0.6774 Remote Similarity NPD5175 Approved
0.6752 Remote Similarity NPD6101 Approved
0.6752 Remote Similarity NPD5328 Approved
0.6752 Remote Similarity NPD5764 Clinical (unspecified phase)
0.675 Remote Similarity NPD1698 Clinical (unspecified phase)
0.675 Remote Similarity NPD5695 Phase 3
0.6748 Remote Similarity NPD5223 Approved
0.6742 Remote Similarity NPD6314 Approved
0.6742 Remote Similarity NPD6313 Approved
0.6724 Remote Similarity NPD3573 Approved
0.6718 Remote Similarity NPD6868 Approved
0.6716 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6694 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6694 Remote Similarity NPD5222 Approved
0.6694 Remote Similarity NPD5221 Approved
0.6693 Remote Similarity NPD4730 Approved
0.6693 Remote Similarity NPD4729 Approved
0.6667 Remote Similarity NPD6672 Approved
0.6667 Remote Similarity NPD5737 Approved
0.664 Remote Similarity NPD4754 Approved
0.6639 Remote Similarity NPD5173 Approved
0.6639 Remote Similarity NPD7637 Suspended
0.6639 Remote Similarity NPD5693 Phase 1
0.6639 Remote Similarity NPD6079 Approved
0.6638 Remote Similarity NPD3618 Phase 1
0.6589 Remote Similarity NPD5247 Approved
0.6589 Remote Similarity NPD5249 Phase 3
0.6589 Remote Similarity NPD5250 Approved
0.6589 Remote Similarity NPD5251 Approved
0.6589 Remote Similarity NPD5248 Approved
0.6585 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6573 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6562 Remote Similarity NPD5128 Approved
0.6552 Remote Similarity NPD1694 Approved
0.6509 Remote Similarity NPD8434 Phase 2
0.65 Remote Similarity NPD8034 Phase 2
0.65 Remote Similarity NPD8035 Phase 2
0.6488 Remote Similarity NPD8407 Phase 2
0.648 Remote Similarity NPD1700 Approved
0.6475 Remote Similarity NPD5210 Approved
0.6475 Remote Similarity NPD4629 Approved
0.6475 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6673 Approved
0.6471 Remote Similarity NPD4753 Phase 2
0.6471 Remote Similarity NPD6904 Approved
0.6471 Remote Similarity NPD6080 Approved
0.6463 Remote Similarity NPD7799 Discontinued
0.6454 Remote Similarity NPD5956 Approved
0.6446 Remote Similarity NPD4202 Approved
0.6441 Remote Similarity NPD7524 Approved
0.6435 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6417 Remote Similarity NPD5785 Approved
0.6417 Remote Similarity NPD7838 Discovery
0.6412 Remote Similarity NPD5216 Approved
0.6412 Remote Similarity NPD5215 Approved
0.6412 Remote Similarity NPD5217 Approved
0.6407 Remote Similarity NPD8368 Discontinued
0.6389 Remote Similarity NPD8415 Approved
0.6387 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6382 Remote Similarity NPD7236 Approved
0.6379 Remote Similarity NPD6110 Phase 1
0.6377 Remote Similarity NPD6067 Discontinued
0.637 Remote Similarity NPD6334 Approved
0.637 Remote Similarity NPD6333 Approved
0.6356 Remote Similarity NPD7334 Approved
0.6356 Remote Similarity NPD6409 Approved
0.6356 Remote Similarity NPD5330 Approved
0.6356 Remote Similarity NPD7146 Approved
0.6356 Remote Similarity NPD6684 Approved
0.6356 Remote Similarity NPD7521 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