Structure

Physi-Chem Properties

Molecular Weight:  594.27
Volume:  582.874
LogP:  1.694
LogD:  1.839
LogS:  -2.91
# Rotatable Bonds:  14
TPSA:  198.76
# H-Bond Aceptor:  12
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.137
Synthetic Accessibility Score:  4.612
Fsp3:  0.6
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:  -6.157
MDCK Permeability:  6.838553872512421e-06
Pgp-inhibitor:  0.005
Pgp-substrate:  0.343
Human Intestinal Absorption (HIA):  0.99
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.046
Plasma Protein Binding (PPB):  94.63513946533203%
Volume Distribution (VD):  0.169
Pgp-substrate:  2.796140193939209%

ADMET: Metabolism

CYP1A2-inhibitor:  0.024
CYP1A2-substrate:  0.029
CYP2C19-inhibitor:  0.052
CYP2C19-substrate:  0.092
CYP2C9-inhibitor:  0.036
CYP2C9-substrate:  0.265
CYP2D6-inhibitor:  0.055
CYP2D6-substrate:  0.154
CYP3A4-inhibitor:  0.026
CYP3A4-substrate:  0.124

ADMET: Excretion

Clearance (CL):  1.38
Half-life (T1/2):  0.8

ADMET: Toxicity

hERG Blockers:  0.308
Human Hepatotoxicity (H-HT):  0.068
Drug-inuced Liver Injury (DILI):  0.023
AMES Toxicity:  0.411
Rat Oral Acute Toxicity:  0.103
Maximum Recommended Daily Dose:  0.182
Skin Sensitization:  0.961
Carcinogencity:  0.089
Eye Corrosion:  0.003
Eye Irritation:  0.026
Respiratory Toxicity:  0.029

Download Data

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

  Natural Product: NPC178449

Natural Product ID:  NPC178449
Common Name*:   (2R,3R,4S,5S,6R)-2-[(3R)-1,7-Bis(4-Hydroxyphenyl)Heptan-3-Yl]Oxy-6-[[(2R,3R,4R)-3,4-Dihydroxy-4-(Hydroxymethyl)Oxolan-2-Yl]Oxymethyl]Oxane-3,4,5-Triol
IUPAC Name:   (2R,3R,4S,5S,6R)-2-[(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  JLMGCBFIPZDHLZ-GYOMMSMMSA-N
Standard InCHI:  InChI=1S/C30H42O12/c31-16-30(38)17-40-29(27(30)37)39-15-23-24(34)25(35)26(36)28(42-23)41-22(14-9-19-7-12-21(33)13-8-19)4-2-1-3-18-5-10-20(32)11-6-18/h5-8,10-13,22-29,31-38H,1-4,9,14-17H2/t22-,23-,24-,25+,26-,27+,28-,29-,30-/m1/s1
SMILES:  C(CC[C@H](CCc1ccc(cc1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@@](CO)(CO2)O)O)O1)O)O)O)Cc1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1774773
PubChem CID:   21637600
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002650] Diarylheptanoids
        • [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO4971 Alnus firma Species Betulaceae Eukaryota n.a. n.a. n.a. PMID[21504848]
NPO4971 Alnus firma Species Betulaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 22.7 % PMID[565977]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 39100.0 nM PMID[565977]

☑ 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 NPC178449 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 NPC470907
1.0 High Similarity NPC232454
0.9914 High Similarity NPC471067
0.9741 High Similarity NPC469703
0.9741 High Similarity NPC201402
0.9741 High Similarity NPC469704
0.9741 High Similarity NPC160854
0.9667 High Similarity NPC469687
0.9658 High Similarity NPC469686
0.9573 High Similarity NPC476445
0.9573 High Similarity NPC476448
0.9573 High Similarity NPC469548
0.9487 High Similarity NPC282409
0.9487 High Similarity NPC469702
0.9206 High Similarity NPC164172
0.92 High Similarity NPC478255
0.9187 High Similarity NPC264900
0.9187 High Similarity NPC79715
0.9187 High Similarity NPC108659
0.9187 High Similarity NPC231607
0.9167 High Similarity NPC55608
0.9145 High Similarity NPC148055
0.9138 High Similarity NPC157338
0.9127 High Similarity NPC471095
0.9127 High Similarity NPC471066
0.9106 High Similarity NPC94179
0.904 High Similarity NPC184092
0.9024 High Similarity NPC90318
0.8968 High Similarity NPC469705
0.8968 High Similarity NPC17968
0.8968 High Similarity NPC470122
0.896 High Similarity NPC225307
0.8923 High Similarity NPC469696
0.888 High Similarity NPC288416
0.8828 High Similarity NPC254275
0.8824 High Similarity NPC175771
0.8824 High Similarity NPC301651
0.8824 High Similarity NPC473556
0.8814 High Similarity NPC313193
0.881 High Similarity NPC158673
0.881 High Similarity NPC148982
0.875 High Similarity NPC235294
0.875 High Similarity NPC46137
0.8712 High Similarity NPC171134
0.8712 High Similarity NPC321638
0.8712 High Similarity NPC328273
0.8712 High Similarity NPC321184
0.8699 High Similarity NPC266045
0.864 High Similarity NPC287429
0.8615 High Similarity NPC28637
0.8605 High Similarity NPC138777
0.8605 High Similarity NPC476407
0.8605 High Similarity NPC225384
0.8605 High Similarity NPC246869
0.8594 High Similarity NPC469549
0.8593 High Similarity NPC46092
0.8583 High Similarity NPC173150
0.8583 High Similarity NPC106677
0.8583 High Similarity NPC471882
0.8583 High Similarity NPC45224
0.8583 High Similarity NPC471881
0.8583 High Similarity NPC35288
0.8583 High Similarity NPC156692
0.8582 High Similarity NPC472711
0.8571 High Similarity NPC83218
0.8571 High Similarity NPC126991
0.8561 High Similarity NPC199459
0.8561 High Similarity NPC177035
0.8561 High Similarity NPC52277
0.8529 High Similarity NPC129417
0.8529 High Similarity NPC283995
0.8529 High Similarity NPC470235
0.8529 High Similarity NPC84181
0.8519 High Similarity NPC472353
0.8504 High Similarity NPC61181
0.8504 High Similarity NPC471157
0.8504 High Similarity NPC252114
0.8487 Intermediate Similarity NPC153795
0.8487 Intermediate Similarity NPC290353
0.8487 Intermediate Similarity NPC42911
0.8485 Intermediate Similarity NPC79957
0.8485 Intermediate Similarity NPC263829
0.848 Intermediate Similarity NPC476142
0.848 Intermediate Similarity NPC52097
0.8467 Intermediate Similarity NPC18979
0.8462 Intermediate Similarity NPC475824
0.8456 Intermediate Similarity NPC477898
0.8456 Intermediate Similarity NPC105005
0.8456 Intermediate Similarity NPC185307
0.8456 Intermediate Similarity NPC470950
0.8456 Intermediate Similarity NPC478250
0.8456 Intermediate Similarity NPC40305
0.8438 Intermediate Similarity NPC103533
0.8433 Intermediate Similarity NPC156376
0.8425 Intermediate Similarity NPC470510
0.8413 Intermediate Similarity NPC212176
0.8409 Intermediate Similarity NPC470881
0.8409 Intermediate Similarity NPC476411
0.8409 Intermediate Similarity NPC287597
0.8409 Intermediate Similarity NPC886
0.8409 Intermediate Similarity NPC34293
0.8406 Intermediate Similarity NPC112861
0.84 Intermediate Similarity NPC11724
0.8394 Intermediate Similarity NPC300894
0.8394 Intermediate Similarity NPC141455
0.8394 Intermediate Similarity NPC196063
0.8394 Intermediate Similarity NPC296954
0.8382 Intermediate Similarity NPC476356
0.837 Intermediate Similarity NPC106944
0.8358 Intermediate Similarity NPC87777
0.8358 Intermediate Similarity NPC470413
0.8358 Intermediate Similarity NPC138738
0.8358 Intermediate Similarity NPC260425
0.8358 Intermediate Similarity NPC304152
0.8358 Intermediate Similarity NPC262328
0.8346 Intermediate Similarity NPC158325
0.8346 Intermediate Similarity NPC103398
0.8346 Intermediate Similarity NPC123988
0.8346 Intermediate Similarity NPC180171
0.8333 Intermediate Similarity NPC22150
0.8333 Intermediate Similarity NPC469586
0.8333 Intermediate Similarity NPC38041
0.8333 Intermediate Similarity NPC279298
0.8333 Intermediate Similarity NPC6836
0.8333 Intermediate Similarity NPC215037
0.8321 Intermediate Similarity NPC475067
0.832 Intermediate Similarity NPC269242
0.832 Intermediate Similarity NPC476872
0.832 Intermediate Similarity NPC198734
0.832 Intermediate Similarity NPC469412
0.8319 Intermediate Similarity NPC264784
0.8309 Intermediate Similarity NPC471908
0.8296 Intermediate Similarity NPC89105
0.8296 Intermediate Similarity NPC205195
0.8296 Intermediate Similarity NPC197316
0.8296 Intermediate Similarity NPC81515
0.8296 Intermediate Similarity NPC64141
0.8296 Intermediate Similarity NPC476383
0.8296 Intermediate Similarity NPC472350
0.8296 Intermediate Similarity NPC68092
0.8293 Intermediate Similarity NPC476266
0.8284 Intermediate Similarity NPC471345
0.8284 Intermediate Similarity NPC469383
0.8276 Intermediate Similarity NPC47286
0.8273 Intermediate Similarity NPC229505
0.8271 Intermediate Similarity NPC35731
0.8271 Intermediate Similarity NPC169398
0.8271 Intermediate Similarity NPC187194
0.8261 Intermediate Similarity NPC473046
0.8261 Intermediate Similarity NPC187774
0.8261 Intermediate Similarity NPC118385
0.8261 Intermediate Similarity NPC472713
0.8261 Intermediate Similarity NPC472712
0.8258 Intermediate Similarity NPC473924
0.8258 Intermediate Similarity NPC26080
0.8258 Intermediate Similarity NPC165686
0.8258 Intermediate Similarity NPC303422
0.8258 Intermediate Similarity NPC252833
0.8258 Intermediate Similarity NPC85799
0.8248 Intermediate Similarity NPC148080
0.8248 Intermediate Similarity NPC469623
0.8248 Intermediate Similarity NPC246947
0.824 Intermediate Similarity NPC60589
0.824 Intermediate Similarity NPC469708
0.8222 Intermediate Similarity NPC100558
0.8222 Intermediate Similarity NPC302583
0.8222 Intermediate Similarity NPC84789
0.8222 Intermediate Similarity NPC310252
0.8222 Intermediate Similarity NPC78363
0.8214 Intermediate Similarity NPC224674
0.8214 Intermediate Similarity NPC114505
0.8214 Intermediate Similarity NPC193473
0.8214 Intermediate Similarity NPC31325
0.8214 Intermediate Similarity NPC15956
0.8214 Intermediate Similarity NPC275284
0.8214 Intermediate Similarity NPC213074
0.8214 Intermediate Similarity NPC39657
0.8209 Intermediate Similarity NPC184938
0.8209 Intermediate Similarity NPC101624
0.8201 Intermediate Similarity NPC43508
0.8201 Intermediate Similarity NPC476301
0.8195 Intermediate Similarity NPC115022
0.8195 Intermediate Similarity NPC254398
0.8195 Intermediate Similarity NPC294166
0.8195 Intermediate Similarity NPC25821
0.8188 Intermediate Similarity NPC278961
0.8188 Intermediate Similarity NPC113680
0.8182 Intermediate Similarity NPC65942
0.8182 Intermediate Similarity NPC281798
0.8182 Intermediate Similarity NPC121376
0.8182 Intermediate Similarity NPC248307
0.8182 Intermediate Similarity NPC254819
0.8182 Intermediate Similarity NPC219677
0.8175 Intermediate Similarity NPC476385
0.8175 Intermediate Similarity NPC134405
0.8175 Intermediate Similarity NPC469661
0.8175 Intermediate Similarity NPC229600
0.8175 Intermediate Similarity NPC476377
0.8175 Intermediate Similarity NPC210192
0.8175 Intermediate Similarity NPC108674

  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 NPC178449 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
0.8296 Intermediate Similarity NPD7266 Discontinued
0.7969 Intermediate Similarity NPD1091 Approved
0.7812 Intermediate Similarity NPD5125 Phase 3
0.7812 Intermediate Similarity NPD5126 Approved
0.7746 Intermediate Similarity NPD5058 Phase 3
0.7521 Intermediate Similarity NPD2859 Approved
0.7521 Intermediate Similarity NPD2860 Approved
0.75 Intermediate Similarity NPD3027 Phase 3
0.7464 Intermediate Similarity NPD1613 Approved
0.7464 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD2934 Approved
0.7436 Intermediate Similarity NPD2933 Approved
0.7429 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD5588 Approved
0.7353 Intermediate Similarity NPD2861 Phase 2
0.7351 Intermediate Similarity NPD8455 Phase 2
0.7333 Intermediate Similarity NPD3094 Phase 2
0.7333 Intermediate Similarity NPD3020 Approved
0.7323 Intermediate Similarity NPD7843 Approved
0.732 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD3021 Approved
0.7222 Intermediate Similarity NPD3022 Approved
0.7192 Intermediate Similarity NPD6190 Approved
0.7183 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD4538 Approved
0.7183 Intermediate Similarity NPD4536 Approved
0.7183 Intermediate Similarity NPD7097 Phase 1
0.7174 Intermediate Similarity NPD4908 Phase 1
0.7174 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD6674 Discontinued
0.717 Intermediate Similarity NPD7228 Approved
0.7164 Intermediate Similarity NPD1610 Phase 2
0.7164 Intermediate Similarity NPD3092 Approved
0.7164 Intermediate Similarity NPD3705 Approved
0.7154 Intermediate Similarity NPD7157 Approved
0.7143 Intermediate Similarity NPD2684 Approved
0.7133 Intermediate Similarity NPD5960 Phase 3
0.7133 Intermediate Similarity NPD1653 Approved
0.7121 Intermediate Similarity NPD1548 Phase 1
0.7101 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD4103 Phase 2
0.708 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD940 Approved
0.7073 Intermediate Similarity NPD846 Approved
0.7071 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD1357 Approved
0.7063 Intermediate Similarity NPD3818 Discontinued
0.7059 Intermediate Similarity NPD37 Approved
0.7059 Intermediate Similarity NPD4659 Approved
0.7051 Intermediate Similarity NPD6234 Discontinued
0.7032 Intermediate Similarity NPD4966 Approved
0.7032 Intermediate Similarity NPD4965 Approved
0.7032 Intermediate Similarity NPD4967 Phase 2
0.7021 Intermediate Similarity NPD6405 Approved
0.7021 Intermediate Similarity NPD6407 Approved
0.7019 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD5846 Approved
0.7015 Intermediate Similarity NPD6516 Phase 2
0.6994 Remote Similarity NPD6559 Discontinued
0.6992 Remote Similarity NPD1242 Phase 1
0.6992 Remote Similarity NPD3091 Approved
0.698 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6977 Remote Similarity NPD969 Suspended
0.6975 Remote Similarity NPD7074 Phase 3
0.695 Remote Similarity NPD3764 Approved
0.6939 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6928 Remote Similarity NPD4380 Phase 2
0.6918 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6914 Remote Similarity NPD7054 Approved
0.6901 Remote Similarity NPD6233 Phase 2
0.6897 Remote Similarity NPD7033 Discontinued
0.689 Remote Similarity NPD7685 Pre-registration
0.6884 Remote Similarity NPD8651 Approved
0.6871 Remote Similarity NPD7472 Approved
0.6866 Remote Similarity NPD7741 Discontinued
0.686 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5736 Approved
0.6855 Remote Similarity NPD3028 Approved
0.685 Remote Similarity NPD968 Approved
0.6835 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6831 Remote Similarity NPD6798 Discontinued
0.6822 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6806 Remote Similarity NPD4340 Discontinued
0.6806 Remote Similarity NPD6355 Discontinued
0.6797 Remote Similarity NPD290 Approved
0.6795 Remote Similarity NPD2978 Approved
0.6795 Remote Similarity NPD2977 Approved
0.6788 Remote Similarity NPD7251 Discontinued
0.6788 Remote Similarity NPD7240 Approved
0.6781 Remote Similarity NPD4108 Discontinued
0.6779 Remote Similarity NPD4628 Phase 3
0.6767 Remote Similarity NPD6671 Approved
0.6765 Remote Similarity NPD3095 Discontinued
0.6761 Remote Similarity NPD7095 Approved
0.6759 Remote Similarity NPD5314 Approved
0.675 Remote Similarity NPD7199 Phase 2
0.6747 Remote Similarity NPD7808 Phase 3
0.6739 Remote Similarity NPD2561 Approved
0.6739 Remote Similarity NPD2562 Approved
0.6736 Remote Similarity NPD4060 Phase 1
0.6736 Remote Similarity NPD3059 Approved
0.6736 Remote Similarity NPD3062 Approved
0.6736 Remote Similarity NPD3061 Approved
0.6727 Remote Similarity NPD6797 Phase 2
0.6726 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6713 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6713 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6711 Remote Similarity NPD1652 Phase 2
0.6691 Remote Similarity NPD6582 Phase 2
0.6691 Remote Similarity NPD6583 Phase 3
0.6691 Remote Similarity NPD3685 Discontinued
0.669 Remote Similarity NPD5124 Phase 1
0.669 Remote Similarity NPD5123 Clinical (unspecified phase)
0.669 Remote Similarity NPD5735 Approved
0.6667 Remote Similarity NPD6663 Approved
0.6667 Remote Similarity NPD111 Approved
0.6667 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7075 Discontinued
0.6667 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4535 Phase 3
0.6667 Remote Similarity NPD5535 Approved
0.6647 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6644 Remote Similarity NPD2424 Discontinued
0.6643 Remote Similarity NPD4625 Phase 3
0.6642 Remote Similarity NPD9381 Approved
0.6642 Remote Similarity NPD9384 Approved
0.6621 Remote Similarity NPD3620 Phase 2
0.6621 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6621 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6617 Remote Similarity NPD2228 Approved
0.6617 Remote Similarity NPD7159 Clinical (unspecified phase)
0.6617 Remote Similarity NPD2234 Approved
0.6617 Remote Similarity NPD2229 Approved
0.6617 Remote Similarity NPD5283 Phase 1
0.6607 Remote Similarity NPD8313 Approved
0.6607 Remote Similarity NPD8312 Approved
0.6604 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6601 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6591 Remote Similarity NPD6124 Clinical (unspecified phase)
0.6591 Remote Similarity NPD228 Approved
0.6577 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6577 Remote Similarity NPD5763 Approved
0.6577 Remote Similarity NPD5762 Approved
0.6577 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6571 Remote Similarity NPD4749 Approved
0.6565 Remote Similarity NPD5451 Approved
0.6565 Remote Similarity NPD4750 Phase 3
0.6564 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6556 Remote Similarity NPD3400 Discontinued
0.6552 Remote Similarity NPD4404 Approved
0.6552 Remote Similarity NPD4062 Phase 3
0.6549 Remote Similarity NPD6584 Phase 3
0.6549 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6544 Remote Similarity NPD856 Approved
0.6544 Remote Similarity NPD16 Approved
0.6541 Remote Similarity NPD7635 Approved
0.6536 Remote Similarity NPD7212 Phase 2
0.6536 Remote Similarity NPD7213 Phase 3
0.6533 Remote Similarity NPD1549 Phase 2
0.6532 Remote Similarity NPD1809 Phase 2
0.6532 Remote Similarity NPD844 Approved
0.6532 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6531 Remote Similarity NPD2568 Approved
0.6531 Remote Similarity NPD6653 Approved
0.6527 Remote Similarity NPD7007 Discovery
0.6522 Remote Similarity NPD4059 Approved
0.6519 Remote Similarity NPD4198 Discontinued
0.6519 Remote Similarity NPD1934 Approved
0.6516 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6512 Remote Similarity NPD5048 Discontinued
0.6507 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6507 Remote Similarity NPD2238 Phase 2
0.6504 Remote Similarity NPD845 Approved
0.6503 Remote Similarity NPD3787 Discontinued
0.6496 Remote Similarity NPD9545 Approved
0.6494 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6494 Remote Similarity NPD7447 Phase 1
0.6494 Remote Similarity NPD3536 Discontinued
0.6494 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6493 Remote Similarity NPD4869 Clinical (unspecified phase)
0.649 Remote Similarity NPD4236 Phase 3
0.649 Remote Similarity NPD4237 Approved
0.6478 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6478 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6475 Remote Similarity NPD3847 Discontinued
0.6471 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6467 Remote Similarity NPD1375 Discontinued
0.6457 Remote Similarity NPD289 Clinical (unspecified phase)
0.6456 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6454 Remote Similarity NPD2982 Phase 2
0.6454 Remote Similarity NPD9622 Approved
0.6454 Remote Similarity NPD7876 Discontinued
0.6454 Remote Similarity NPD2983 Phase 2
0.6454 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6454 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6444 Remote Similarity NPD2629 Approved
0.6433 Remote Similarity NPD6056 Approved
0.6433 Remote Similarity NPD6057 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