Structure

Physi-Chem Properties

Molecular Weight:  332.24
Volume:  370.484
LogP:  4.717
LogD:  3.981
LogS:  -4.534
# Rotatable Bonds:  6
TPSA:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.312
Synthetic Accessibility Score:  4.248
Fsp3:  0.714
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.585
MDCK Permeability:  2.6234041797579266e-05
Pgp-inhibitor:  0.918
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.162
30% Bioavailability (F30%):  0.102

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.671
Plasma Protein Binding (PPB):  56.2685661315918%
Volume Distribution (VD):  0.84
Pgp-substrate:  50.85582733154297%

ADMET: Metabolism

CYP1A2-inhibitor:  0.088
CYP1A2-substrate:  0.301
CYP2C19-inhibitor:  0.396
CYP2C19-substrate:  0.771
CYP2C9-inhibitor:  0.455
CYP2C9-substrate:  0.225
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.68
CYP3A4-inhibitor:  0.679
CYP3A4-substrate:  0.285

ADMET: Excretion

Clearance (CL):  9.222
Half-life (T1/2):  0.292

ADMET: Toxicity

hERG Blockers:  0.043
Human Hepatotoxicity (H-HT):  0.327
Drug-inuced Liver Injury (DILI):  0.095
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.645
Maximum Recommended Daily Dose:  0.872
Skin Sensitization:  0.937
Carcinogencity:  0.84
Eye Corrosion:  0.97
Eye Irritation:  0.604
Respiratory Toxicity:  0.982

Download Data

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

  Natural Product: NPC144947

Natural Product ID:  NPC144947
Common Name*:   Pahangensin B
IUPAC Name:   methyl (E)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-formylpent-3-enoate
Synonyms:  
Standard InCHIKey:  AAXFYBBSIXCIRH-MEVJKDFFSA-N
Standard InCHI:  InChI=1S/C21H32O3/c1-15-7-10-18-20(2,3)11-6-12-21(18,4)17(15)9-8-16(14-22)13-19(23)24-5/h8,14,17-18H,1,6-7,9-13H2,2-5H3/b16-8+/t17-,18-,21+/m0/s1
SMILES:  C=C1CC[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1C/C=C(CC(=O)OC)/C=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3087227
PubChem CID:   72543921
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

*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
NPO32724 Alpinia pahangensis Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[24144849]

☑ 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
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 52.08 ug.mL-1 PMID[550278]

☑ 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 NPC144947 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
0.9286 High Similarity NPC168975
0.9286 High Similarity NPC75485
0.9014 High Similarity NPC238146
0.8806 High Similarity NPC169275
0.8806 High Similarity NPC52449
0.8052 Intermediate Similarity NPC59436
0.8028 Intermediate Similarity NPC185587
0.8025 Intermediate Similarity NPC2709
0.8 Intermediate Similarity NPC469
0.8 Intermediate Similarity NPC211641
0.8 Intermediate Similarity NPC128346
0.8 Intermediate Similarity NPC219232
0.7917 Intermediate Similarity NPC290350
0.7917 Intermediate Similarity NPC4370
0.7875 Intermediate Similarity NPC142683
0.7808 Intermediate Similarity NPC155198
0.7792 Intermediate Similarity NPC4509
0.7792 Intermediate Similarity NPC19907
0.7792 Intermediate Similarity NPC474463
0.7765 Intermediate Similarity NPC159748
0.7765 Intermediate Similarity NPC101651
0.7763 Intermediate Similarity NPC20025
0.775 Intermediate Similarity NPC90055
0.7722 Intermediate Similarity NPC283789
0.7647 Intermediate Similarity NPC469546
0.7639 Intermediate Similarity NPC107258
0.7595 Intermediate Similarity NPC115515
0.759 Intermediate Similarity NPC217394
0.759 Intermediate Similarity NPC30984
0.7586 Intermediate Similarity NPC474185
0.7586 Intermediate Similarity NPC151722
0.7532 Intermediate Similarity NPC166797
0.75 Intermediate Similarity NPC474562
0.75 Intermediate Similarity NPC329698
0.75 Intermediate Similarity NPC269729
0.7468 Intermediate Similarity NPC472300
0.7442 Intermediate Similarity NPC471654
0.7442 Intermediate Similarity NPC477973
0.7439 Intermediate Similarity NPC94200
0.7439 Intermediate Similarity NPC200513
0.7439 Intermediate Similarity NPC470813
0.7436 Intermediate Similarity NPC65650
0.7416 Intermediate Similarity NPC274417
0.7407 Intermediate Similarity NPC474956
0.7397 Intermediate Similarity NPC268039
0.7356 Intermediate Similarity NPC328141
0.7349 Intermediate Similarity NPC22611
0.7349 Intermediate Similarity NPC307258
0.7342 Intermediate Similarity NPC469796
0.7342 Intermediate Similarity NPC469793
0.7326 Intermediate Similarity NPC473229
0.7317 Intermediate Similarity NPC40228
0.7317 Intermediate Similarity NPC149237
0.7297 Intermediate Similarity NPC259156
0.7297 Intermediate Similarity NPC242945
0.7294 Intermediate Similarity NPC168248
0.7286 Intermediate Similarity NPC60772
0.7284 Intermediate Similarity NPC190211
0.7284 Intermediate Similarity NPC476177
0.7284 Intermediate Similarity NPC470429
0.7273 Intermediate Similarity NPC230064
0.7273 Intermediate Similarity NPC72343
0.7273 Intermediate Similarity NPC257618
0.7273 Intermediate Similarity NPC21944
0.7273 Intermediate Similarity NPC476187
0.7273 Intermediate Similarity NPC474539
0.7273 Intermediate Similarity NPC133253
0.725 Intermediate Similarity NPC470428
0.7241 Intermediate Similarity NPC474396
0.7241 Intermediate Similarity NPC79027
0.7241 Intermediate Similarity NPC50488
0.7229 Intermediate Similarity NPC15910
0.7229 Intermediate Similarity NPC186276
0.7195 Intermediate Similarity NPC474509
0.7191 Intermediate Similarity NPC476416
0.7179 Intermediate Similarity NPC472813
0.7176 Intermediate Similarity NPC65661
0.7176 Intermediate Similarity NPC329738
0.7176 Intermediate Similarity NPC86316
0.7176 Intermediate Similarity NPC106416
0.716 Intermediate Similarity NPC105197
0.716 Intermediate Similarity NPC239098
0.716 Intermediate Similarity NPC228911
0.716 Intermediate Similarity NPC35574
0.716 Intermediate Similarity NPC476949
0.716 Intermediate Similarity NPC198240
0.716 Intermediate Similarity NPC4827
0.7159 Intermediate Similarity NPC253186
0.7143 Intermediate Similarity NPC474976
0.7143 Intermediate Similarity NPC42476
0.7143 Intermediate Similarity NPC474790
0.7143 Intermediate Similarity NPC118423
0.7126 Intermediate Similarity NPC291665
0.7125 Intermediate Similarity NPC899
0.7125 Intermediate Similarity NPC41017
0.7111 Intermediate Similarity NPC476415
0.7108 Intermediate Similarity NPC229584
0.7108 Intermediate Similarity NPC474955
0.7108 Intermediate Similarity NPC278459
0.7108 Intermediate Similarity NPC170303
0.7108 Intermediate Similarity NPC159148
0.7108 Intermediate Similarity NPC475665
0.7108 Intermediate Similarity NPC14203
0.7097 Intermediate Similarity NPC475392
0.7097 Intermediate Similarity NPC475385
0.7097 Intermediate Similarity NPC470906
0.7097 Intermediate Similarity NPC475202
0.7093 Intermediate Similarity NPC220478
0.7093 Intermediate Similarity NPC195640
0.7089 Intermediate Similarity NPC104644
0.7089 Intermediate Similarity NPC309852
0.7089 Intermediate Similarity NPC306928
0.7089 Intermediate Similarity NPC78527
0.7079 Intermediate Similarity NPC72845
0.7073 Intermediate Similarity NPC476438
0.7073 Intermediate Similarity NPC192999
0.7073 Intermediate Similarity NPC327674
0.7073 Intermediate Similarity NPC170793
0.7073 Intermediate Similarity NPC153987
0.7073 Intermediate Similarity NPC44083
0.7073 Intermediate Similarity NPC90965
0.7073 Intermediate Similarity NPC100906
0.7059 Intermediate Similarity NPC96055
0.7059 Intermediate Similarity NPC139566
0.7059 Intermediate Similarity NPC312660
0.7051 Intermediate Similarity NPC160817
0.7051 Intermediate Similarity NPC304983
0.7045 Intermediate Similarity NPC177141
0.7045 Intermediate Similarity NPC168131
0.7045 Intermediate Similarity NPC474844
0.7045 Intermediate Similarity NPC174342
0.7037 Intermediate Similarity NPC219809
0.7037 Intermediate Similarity NPC165711
0.7037 Intermediate Similarity NPC61952
0.7033 Intermediate Similarity NPC476519
0.7033 Intermediate Similarity NPC139459
0.7024 Intermediate Similarity NPC327969
0.7024 Intermediate Similarity NPC240302
0.7024 Intermediate Similarity NPC321289
0.7024 Intermediate Similarity NPC471218
0.7024 Intermediate Similarity NPC178676
0.7024 Intermediate Similarity NPC268122
0.7024 Intermediate Similarity NPC100297
0.7024 Intermediate Similarity NPC16321
0.7011 Intermediate Similarity NPC264546
0.7 Intermediate Similarity NPC476346
0.7 Intermediate Similarity NPC476844
0.6989 Remote Similarity NPC194196
0.6988 Remote Similarity NPC2482
0.6988 Remote Similarity NPC195424
0.6988 Remote Similarity NPC104545
0.6988 Remote Similarity NPC281880
0.6988 Remote Similarity NPC267517
0.6977 Remote Similarity NPC470223
0.6977 Remote Similarity NPC189311
0.6977 Remote Similarity NPC474680
0.6977 Remote Similarity NPC476602
0.6977 Remote Similarity NPC323765
0.6974 Remote Similarity NPC193770
0.6966 Remote Similarity NPC273199
0.6966 Remote Similarity NPC474842
0.6966 Remote Similarity NPC475965
0.6962 Remote Similarity NPC56747
0.6962 Remote Similarity NPC180015
0.6962 Remote Similarity NPC276336
0.6962 Remote Similarity NPC109576
0.6962 Remote Similarity NPC303613
0.6962 Remote Similarity NPC474228
0.6962 Remote Similarity NPC130016
0.6957 Remote Similarity NPC122324
0.6957 Remote Similarity NPC151725
0.6957 Remote Similarity NPC106425
0.6957 Remote Similarity NPC471039
0.6951 Remote Similarity NPC321514
0.6941 Remote Similarity NPC470165
0.6941 Remote Similarity NPC476927
0.6933 Remote Similarity NPC183422
0.6932 Remote Similarity NPC215831
0.6932 Remote Similarity NPC474474
0.6932 Remote Similarity NPC226863
0.6932 Remote Similarity NPC224145
0.6932 Remote Similarity NPC472870
0.6932 Remote Similarity NPC206060
0.6932 Remote Similarity NPC104560
0.6923 Remote Similarity NPC251929
0.6923 Remote Similarity NPC265782
0.6923 Remote Similarity NPC91369
0.6923 Remote Similarity NPC2634
0.6923 Remote Similarity NPC469660
0.6923 Remote Similarity NPC294266
0.6923 Remote Similarity NPC470697
0.6923 Remote Similarity NPC57117
0.6923 Remote Similarity NPC260040
0.6923 Remote Similarity NPC471040
0.6914 Remote Similarity NPC26504
0.6914 Remote Similarity NPC27205
0.6914 Remote Similarity NPC69143
0.6914 Remote Similarity NPC40353
0.6914 Remote Similarity NPC180886
0.6914 Remote Similarity NPC476601

  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 NPC144947 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
0.7439 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD7521 Approved
0.7093 Intermediate Similarity NPD7334 Approved
0.7093 Intermediate Similarity NPD7146 Approved
0.7093 Intermediate Similarity NPD6409 Approved
0.7093 Intermediate Similarity NPD6684 Approved
0.7093 Intermediate Similarity NPD5330 Approved
0.6932 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6932 Remote Similarity NPD6903 Approved
0.6932 Remote Similarity NPD6672 Approved
0.6932 Remote Similarity NPD5737 Approved
0.6923 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4691 Approved
0.6923 Remote Similarity NPD7900 Approved
0.6813 Remote Similarity NPD6399 Phase 3
0.6795 Remote Similarity NPD4137 Phase 3
0.6709 Remote Similarity NPD4747 Approved
0.6702 Remote Similarity NPD7902 Approved
0.6667 Remote Similarity NPD4058 Approved
0.6632 Remote Similarity NPD4225 Approved
0.6629 Remote Similarity NPD3573 Approved
0.6588 Remote Similarity NPD4695 Discontinued
0.6579 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6559 Remote Similarity NPD7748 Approved
0.6522 Remote Similarity NPD7515 Phase 2
0.6489 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6484 Remote Similarity NPD6080 Approved
0.6484 Remote Similarity NPD6904 Approved
0.6484 Remote Similarity NPD6673 Approved
0.6463 Remote Similarity NPD5733 Approved
0.642 Remote Similarity NPD5276 Approved
0.6404 Remote Similarity NPD1694 Approved
0.6386 Remote Similarity NPD8039 Approved
0.6374 Remote Similarity NPD5208 Approved
0.6354 Remote Similarity NPD6084 Phase 2
0.6354 Remote Similarity NPD6083 Phase 2
0.6344 Remote Similarity NPD7637 Suspended
0.6333 Remote Similarity NPD6098 Approved
0.6333 Remote Similarity NPD3618 Phase 1
0.6316 Remote Similarity NPD4194 Approved
0.6316 Remote Similarity NPD4193 Approved
0.6316 Remote Similarity NPD4191 Approved
0.6316 Remote Similarity NPD4192 Approved
0.6304 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6292 Remote Similarity NPD3666 Approved
0.6292 Remote Similarity NPD4786 Approved
0.6292 Remote Similarity NPD3133 Approved
0.6292 Remote Similarity NPD3665 Phase 1
0.6289 Remote Similarity NPD5696 Approved
0.6289 Remote Similarity NPD7638 Approved
0.6265 Remote Similarity NPD4687 Approved
0.625 Remote Similarity NPD4697 Phase 3
0.625 Remote Similarity NPD3621 Clinical (unspecified phase)
0.625 Remote Similarity NPD7732 Phase 3
0.625 Remote Similarity NPD3667 Approved
0.6237 Remote Similarity NPD5207 Approved
0.6224 Remote Similarity NPD7639 Approved
0.6224 Remote Similarity NPD7640 Approved
0.6211 Remote Similarity NPD6001 Approved
0.6173 Remote Similarity NPD6923 Approved
0.6173 Remote Similarity NPD6922 Approved
0.617 Remote Similarity NPD5693 Phase 1
0.617 Remote Similarity NPD6050 Approved
0.617 Remote Similarity NPD6079 Approved
0.6146 Remote Similarity NPD5695 Phase 3
0.6136 Remote Similarity NPD8028 Phase 2
0.6133 Remote Similarity NPD287 Approved
0.6129 Remote Similarity NPD6051 Approved
0.6129 Remote Similarity NPD5328 Approved
0.6111 Remote Similarity NPD3668 Phase 3
0.6111 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6098 Remote Similarity NPD7143 Approved
0.6098 Remote Similarity NPD7144 Approved
0.6095 Remote Similarity NPD6650 Approved
0.6095 Remote Similarity NPD6649 Approved
0.6092 Remote Similarity NPD4195 Approved
0.6078 Remote Similarity NPD6008 Approved
0.6076 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6071 Remote Similarity NPD6926 Approved
0.6071 Remote Similarity NPD6924 Approved
0.6067 Remote Similarity NPD4223 Phase 3
0.6067 Remote Similarity NPD4221 Approved
0.6067 Remote Similarity NPD5209 Approved
0.6064 Remote Similarity NPD5692 Phase 3
0.6064 Remote Similarity NPD5785 Approved
0.6058 Remote Similarity NPD6372 Approved
0.6058 Remote Similarity NPD6373 Approved
0.6044 Remote Similarity NPD5329 Approved
0.6024 Remote Similarity NPD7152 Approved
0.6024 Remote Similarity NPD7150 Approved
0.6024 Remote Similarity NPD7151 Approved
0.6023 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6 Remote Similarity NPD5694 Approved
0.6 Remote Similarity NPD6411 Approved
0.6 Remote Similarity NPD5284 Approved
0.6 Remote Similarity NPD6942 Approved
0.6 Remote Similarity NPD8035 Phase 2
0.6 Remote Similarity NPD8034 Phase 2
0.6 Remote Similarity NPD7339 Approved
0.6 Remote Similarity NPD5281 Approved
0.5979 Remote Similarity NPD4629 Approved
0.5979 Remote Similarity NPD5210 Approved
0.5978 Remote Similarity NPD5279 Phase 3
0.5978 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5962 Remote Similarity NPD6686 Approved
0.5962 Remote Similarity NPD6881 Approved
0.5962 Remote Similarity NPD6899 Approved
0.5957 Remote Similarity NPD4753 Phase 2
0.5934 Remote Similarity NPD4197 Approved
0.593 Remote Similarity NPD3701 Clinical (unspecified phase)
0.593 Remote Similarity NPD6933 Approved
0.5922 Remote Similarity NPD5739 Approved
0.5922 Remote Similarity NPD6675 Approved
0.5922 Remote Similarity NPD7128 Approved
0.5922 Remote Similarity NPD6402 Approved
0.5918 Remote Similarity NPD7614 Phase 1
0.5909 Remote Similarity NPD7645 Phase 2
0.5882 Remote Similarity NPD6052 Approved
0.587 Remote Similarity NPD7520 Clinical (unspecified phase)
0.587 Remote Similarity NPD5363 Approved
0.5865 Remote Similarity NPD5697 Approved
0.5865 Remote Similarity NPD6614 Approved
0.5862 Remote Similarity NPD5776 Phase 2
0.5862 Remote Similarity NPD6925 Approved
0.5862 Remote Similarity NPD6932 Approved
0.5849 Remote Similarity NPD6883 Approved
0.5849 Remote Similarity NPD7102 Approved
0.5849 Remote Similarity NPD7290 Approved
0.5833 Remote Similarity NPD6927 Phase 3
0.5824 Remote Similarity NPD3527 Clinical (unspecified phase)
0.5824 Remote Similarity NPD4788 Approved
0.5818 Remote Similarity NPD7115 Discovery
0.5814 Remote Similarity NPD8264 Approved
0.581 Remote Similarity NPD6011 Approved
0.581 Remote Similarity NPD7320 Approved
0.5806 Remote Similarity NPD4688 Approved
0.5806 Remote Similarity NPD5690 Phase 2
0.5806 Remote Similarity NPD4689 Approved
0.5806 Remote Similarity NPD5205 Approved
0.5806 Remote Similarity NPD4138 Approved
0.5806 Remote Similarity NPD4519 Discontinued
0.5806 Remote Similarity NPD4690 Approved
0.5806 Remote Similarity NPD4623 Approved
0.5806 Remote Similarity NPD4693 Phase 3
0.58 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5795 Remote Similarity NPD7145 Approved
0.5795 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5795 Remote Similarity NPD3617 Approved
0.5795 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5794 Remote Similarity NPD6869 Approved
0.5794 Remote Similarity NPD6847 Approved
0.5794 Remote Similarity NPD6617 Approved
0.5794 Remote Similarity NPD8130 Phase 1
0.5789 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6101 Approved
0.5778 Remote Similarity NPD5369 Approved
0.5773 Remote Similarity NPD4202 Approved
0.5758 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5758 Remote Similarity NPD5222 Approved
0.5758 Remote Similarity NPD5221 Approved
0.5758 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5755 Remote Similarity NPD6012 Approved
0.5755 Remote Similarity NPD6013 Approved
0.5755 Remote Similarity NPD6014 Approved
0.5743 Remote Similarity NPD6404 Discontinued
0.5741 Remote Similarity NPD6882 Approved
0.5741 Remote Similarity NPD8297 Approved
0.573 Remote Similarity NPD6683 Phase 2
0.573 Remote Similarity NPD6929 Approved
0.5714 Remote Similarity NPD5701 Approved
0.57 Remote Similarity NPD5173 Approved
0.5698 Remote Similarity NPD4785 Approved
0.5698 Remote Similarity NPD4784 Approved
0.5667 Remote Similarity NPD7332 Phase 2
0.5667 Remote Similarity NPD7509 Discontinued
0.5667 Remote Similarity NPD7525 Registered
0.5667 Remote Similarity NPD6931 Approved
0.5667 Remote Similarity NPD7514 Phase 3
0.5667 Remote Similarity NPD6930 Phase 2
0.5657 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5657 Remote Similarity NPD5654 Approved
0.5652 Remote Similarity NPD6097 Approved
0.5652 Remote Similarity NPD5362 Discontinued
0.5652 Remote Similarity NPD6695 Phase 3
0.5652 Remote Similarity NPD6096 Approved
0.5648 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5647 Remote Similarity NPD4243 Approved
0.5638 Remote Similarity NPD6422 Discontinued
0.5638 Remote Similarity NPD5280 Approved
0.5638 Remote Similarity NPD4694 Approved
0.5638 Remote Similarity NPD5786 Approved
0.5634 Remote Similarity NPD5343 Approved
0.5631 Remote Similarity NPD7632 Discontinued
0.5612 Remote Similarity NPD5779 Approved
0.5612 Remote Similarity NPD5778 Approved
0.561 Remote Similarity NPD6108 Clinical (unspecified phase)
0.561 Remote Similarity NPD7331 Phase 2
0.5604 Remote Similarity NPD6898 Phase 1
0.5604 Remote Similarity NPD6902 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