Structure

Physi-Chem Properties

Molecular Weight:  1032.38
Volume:  989.918
LogP:  -0.383
LogD:  -0.41
LogS:  -2.877
# Rotatable Bonds:  22
TPSA:  386.65
# H-Bond Aceptor:  23
# H-Bond Donor:  13
# Rings:  6
# Heavy Atoms:  23

MedChem Properties

QED Drug-Likeness Score:  0.018
Synthetic Accessibility Score:  6.64
Fsp3:  0.56
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.818
MDCK Permeability:  1.6316551409545355e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.999
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.234
Plasma Protein Binding (PPB):  68.34972381591797%
Volume Distribution (VD):  0.394
Pgp-substrate:  22.02947235107422%

ADMET: Metabolism

CYP1A2-inhibitor:  0.031
CYP1A2-substrate:  0.047
CYP2C19-inhibitor:  0.005
CYP2C19-substrate:  0.045
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.032
CYP2D6-inhibitor:  0.035
CYP2D6-substrate:  0.028
CYP3A4-inhibitor:  0.424
CYP3A4-substrate:  0.024

ADMET: Excretion

Clearance (CL):  1.011
Half-life (T1/2):  0.851

ADMET: Toxicity

hERG Blockers:  0.21
Human Hepatotoxicity (H-HT):  0.349
Drug-inuced Liver Injury (DILI):  0.024
AMES Toxicity:  0.071
Rat Oral Acute Toxicity:  0.004
Maximum Recommended Daily Dose:  0.954
Skin Sensitization:  0.966
Carcinogencity:  0.261
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.666

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

  Natural Product: NPC471873

Natural Product ID:  NPC471873
Common Name*:   4-((1S,3S,4S)-4-Formyl-3-Hydroxy-4-(2-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-2-Yloxy)Vinyl)Cyclohexyl)Methyl 1-((1S,3S,4S)-4-Formyl-3-Hydroxy-4-(2-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-2-Yloxy)Ethyl)Cyclohexyl)Methyl 2-(3,4-Dihydroxybenzylidene)-3-(4-Hydroxybenzylidene)Succinate
IUPAC Name:   1-O-[[(1S,3S,4S)-4-formyl-3-hydroxy-4-[(Z)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethenyl]cyclohexyl]methyl] 4-O-[[(1S,3S,4S)-4-formyl-3-hydroxy-4-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]cyclohexyl]methyl] (2E,3E)-3-[(3,4-dihydroxyphenyl)methylidene]-2-[(4-hydroxyphenyl)methylidene]butanedioate
Synonyms:  
Standard InCHIKey:  JLQIKEINPHHAHG-NFJSBNHXSA-N
Standard InCHI:  InChI=1S/C50H64O23/c51-20-35-39(60)41(62)43(64)47(72-35)68-13-11-49(24-53)9-7-28(18-37(49)58)22-70-45(66)31(15-26-1-4-30(55)5-2-26)32(16-27-3-6-33(56)34(57)17-27)46(67)71-23-29-8-10-50(25-54,38(59)19-29)12-14-69-48-44(65)42(63)40(61)36(21-52)73-48/h1-6,11,13,15-17,24-25,28-29,35-44,47-48,51-52,55-65H,7-10,12,14,18-23H2/b13-11-,31-15+,32-16+/t28-,29-,35+,36+,37-,38-,39+,40+,41-,42-,43+,44+,47+,48+,49+,50+/m0/s1
SMILES:  C1CC(C(CC1COC(=O)C(=CC2=CC(=C(C=C2)O)O)C(=CC3=CC=C(C=C3)O)C(=O)OCC4CCC(C(C4)O)(C=COC5C(C(C(C(O5)CO)O)O)O)C=O)O)(CCOC6C(C(C(C(O6)CO)O)O)O)C=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3262202
PubChem CID:   90676285
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001511] Lignan glycosides

*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
NPO9348 Cananga odorata Species Annonaceae Eukaryota fruits n.a. n.a. PMID[11374955]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21504145]
NPO9348 Cananga odorata Species Annonaceae Eukaryota flower buds Thailand n.a. PMID[24601675]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9348 Cananga odorata Species Annonaceae 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
NPT2 Others Unspecified Inhibition = 8.1 % PMID[478681]
NPT2 Others Unspecified Inhibition = 18.0 % PMID[478681]
NPT2 Others Unspecified Inhibition = 18.4 % PMID[478681]
NPT2 Others Unspecified Inhibition = 24.2 % PMID[478681]
NPT2 Others Unspecified Inhibition = 29.8 % PMID[478681]
NPT2 Others Unspecified Inhibition > 100.0 % PMID[478681]
NPT27 Others Unspecified Activity > 95.2 % PMID[478681]

☑ 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 NPC471873 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
0.9935 High Similarity NPC471869
0.9684 High Similarity NPC471870
0.9503 High Similarity NPC471871
0.9477 High Similarity NPC471874
0.9281 High Similarity NPC12006
0.9103 High Similarity NPC87403
0.9038 High Similarity NPC106818
0.8994 High Similarity NPC471878
0.8903 High Similarity NPC28776
0.8903 High Similarity NPC473138
0.8743 High Similarity NPC469776
0.8743 High Similarity NPC469773
0.8743 High Similarity NPC469775
0.8743 High Similarity NPC469772
0.8743 High Similarity NPC469778
0.8743 High Similarity NPC295941
0.8743 High Similarity NPC100925
0.8743 High Similarity NPC469774
0.8743 High Similarity NPC32723
0.8743 High Similarity NPC469777
0.8743 High Similarity NPC135334
0.8634 High Similarity NPC131532
0.8627 High Similarity NPC471875
0.8581 High Similarity NPC264632
0.8581 High Similarity NPC476397
0.8581 High Similarity NPC476375
0.8581 High Similarity NPC76406
0.8581 High Similarity NPC112
0.8581 High Similarity NPC476381
0.8581 High Similarity NPC96795
0.8581 High Similarity NPC269141
0.8581 High Similarity NPC298257
0.8581 High Similarity NPC175214
0.8581 High Similarity NPC119537
0.8581 High Similarity NPC476378
0.8581 High Similarity NPC247032
0.8581 High Similarity NPC205864
0.8581 High Similarity NPC476380
0.8581 High Similarity NPC476384
0.8571 High Similarity NPC476377
0.8571 High Similarity NPC47471
0.8562 High Similarity NPC205195
0.8544 High Similarity NPC23677
0.8529 High Similarity NPC473630
0.8526 High Similarity NPC64195
0.8506 High Similarity NPC475530
0.8506 High Similarity NPC473799
0.8497 Intermediate Similarity NPC260425
0.8471 Intermediate Similarity NPC124828
0.8462 Intermediate Similarity NPC105005
0.8452 Intermediate Similarity NPC476385
0.8452 Intermediate Similarity NPC134405
0.8452 Intermediate Similarity NPC128403
0.8442 Intermediate Similarity NPC89105
0.8442 Intermediate Similarity NPC476383
0.8442 Intermediate Similarity NPC81515
0.8442 Intermediate Similarity NPC64141
0.8442 Intermediate Similarity NPC68092
0.8442 Intermediate Similarity NPC472350
0.8442 Intermediate Similarity NPC197316
0.8424 Intermediate Similarity NPC44507
0.8418 Intermediate Similarity NPC229505
0.8408 Intermediate Similarity NPC300894
0.8408 Intermediate Similarity NPC296954
0.8408 Intermediate Similarity NPC196063
0.8408 Intermediate Similarity NPC141455
0.8397 Intermediate Similarity NPC222433
0.8397 Intermediate Similarity NPC265648
0.8383 Intermediate Similarity NPC227297
0.8377 Intermediate Similarity NPC78363
0.8375 Intermediate Similarity NPC259347
0.8375 Intermediate Similarity NPC476386
0.8375 Intermediate Similarity NPC470933
0.8375 Intermediate Similarity NPC476398
0.8375 Intermediate Similarity NPC94871
0.8375 Intermediate Similarity NPC471062
0.8375 Intermediate Similarity NPC473427
0.8375 Intermediate Similarity NPC306890
0.8364 Intermediate Similarity NPC469654
0.8344 Intermediate Similarity NPC160882
0.8324 Intermediate Similarity NPC469418
0.8323 Intermediate Similarity NPC69367
0.8323 Intermediate Similarity NPC62800
0.8323 Intermediate Similarity NPC324262
0.8323 Intermediate Similarity NPC470927
0.8323 Intermediate Similarity NPC246024
0.8323 Intermediate Similarity NPC257970
0.8304 Intermediate Similarity NPC13989
0.8303 Intermediate Similarity NPC40920
0.8303 Intermediate Similarity NPC187205
0.8303 Intermediate Similarity NPC238419
0.8303 Intermediate Similarity NPC223335
0.8303 Intermediate Similarity NPC172419
0.8301 Intermediate Similarity NPC34293
0.8301 Intermediate Similarity NPC287597
0.8301 Intermediate Similarity NPC886
0.8294 Intermediate Similarity NPC472133
0.8291 Intermediate Similarity NPC183824
0.8284 Intermediate Similarity NPC469419
0.8282 Intermediate Similarity NPC266084
0.8282 Intermediate Similarity NPC475595
0.8282 Intermediate Similarity NPC83663
0.8282 Intermediate Similarity NPC473544
0.8282 Intermediate Similarity NPC475162
0.8282 Intermediate Similarity NPC475216
0.8282 Intermediate Similarity NPC475145
0.828 Intermediate Similarity NPC296643
0.8274 Intermediate Similarity NPC121290
0.8274 Intermediate Similarity NPC25889
0.8263 Intermediate Similarity NPC132737
0.8261 Intermediate Similarity NPC478242
0.8258 Intermediate Similarity NPC476376
0.8253 Intermediate Similarity NPC141331
0.8253 Intermediate Similarity NPC104222
0.8253 Intermediate Similarity NPC114791
0.8253 Intermediate Similarity NPC210501
0.8253 Intermediate Similarity NPC318826
0.825 Intermediate Similarity NPC232992
0.8247 Intermediate Similarity NPC476870
0.8247 Intermediate Similarity NPC123988
0.8247 Intermediate Similarity NPC180171
0.8247 Intermediate Similarity NPC158325
0.8247 Intermediate Similarity NPC103398
0.8246 Intermediate Similarity NPC472129
0.8246 Intermediate Similarity NPC179240
0.8246 Intermediate Similarity NPC43434
0.8246 Intermediate Similarity NPC472803
0.8242 Intermediate Similarity NPC239019
0.8242 Intermediate Similarity NPC247629
0.8239 Intermediate Similarity NPC100998
0.8239 Intermediate Similarity NPC476382
0.8239 Intermediate Similarity NPC53520
0.8239 Intermediate Similarity NPC252292
0.8239 Intermediate Similarity NPC34587
0.8239 Intermediate Similarity NPC34927
0.8235 Intermediate Similarity NPC470271
0.8235 Intermediate Similarity NPC311389
0.8232 Intermediate Similarity NPC472128
0.8232 Intermediate Similarity NPC472127
0.8229 Intermediate Similarity NPC469371
0.8228 Intermediate Similarity NPC285550
0.8228 Intermediate Similarity NPC40305
0.8221 Intermediate Similarity NPC478268
0.8214 Intermediate Similarity NPC145847
0.821 Intermediate Similarity NPC470934
0.821 Intermediate Similarity NPC476871
0.821 Intermediate Similarity NPC188393
0.8205 Intermediate Similarity NPC328273
0.8205 Intermediate Similarity NPC321184
0.8205 Intermediate Similarity NPC321638
0.8205 Intermediate Similarity NPC171134
0.8205 Intermediate Similarity NPC220942
0.8199 Intermediate Similarity NPC116229
0.8198 Intermediate Similarity NPC477617
0.8198 Intermediate Similarity NPC47140
0.8198 Intermediate Similarity NPC67134
0.8194 Intermediate Similarity NPC470572
0.8187 Intermediate Similarity NPC197708
0.8187 Intermediate Similarity NPC658
0.8187 Intermediate Similarity NPC320734
0.8182 Intermediate Similarity NPC475484
0.8176 Intermediate Similarity NPC471876
0.8176 Intermediate Similarity NPC476867
0.8176 Intermediate Similarity NPC175793
0.8171 Intermediate Similarity NPC61604
0.8171 Intermediate Similarity NPC299706
0.8171 Intermediate Similarity NPC3746
0.8171 Intermediate Similarity NPC115466
0.8171 Intermediate Similarity NPC195114
0.8171 Intermediate Similarity NPC16024
0.8171 Intermediate Similarity NPC205037
0.8171 Intermediate Similarity NPC44260
0.8171 Intermediate Similarity NPC61152
0.8171 Intermediate Similarity NPC245615
0.8167 Intermediate Similarity NPC475299
0.8166 Intermediate Similarity NPC109990
0.8165 Intermediate Similarity NPC469623
0.8165 Intermediate Similarity NPC148080
0.8161 Intermediate Similarity NPC76112
0.8161 Intermediate Similarity NPC469397
0.8161 Intermediate Similarity NPC92403
0.8161 Intermediate Similarity NPC170018
0.8161 Intermediate Similarity NPC66820
0.816 Intermediate Similarity NPC140151
0.816 Intermediate Similarity NPC7145
0.816 Intermediate Similarity NPC85192
0.816 Intermediate Similarity NPC143480
0.816 Intermediate Similarity NPC125823
0.8155 Intermediate Similarity NPC7191
0.8155 Intermediate Similarity NPC149873
0.8155 Intermediate Similarity NPC478267
0.8153 Intermediate Similarity NPC156709
0.8153 Intermediate Similarity NPC179505
0.815 Intermediate Similarity NPC316539
0.8146 Intermediate Similarity NPC65489
0.8141 Intermediate Similarity NPC302583
0.8141 Intermediate Similarity NPC84789
0.8141 Intermediate Similarity NPC310252
0.8141 Intermediate Similarity NPC100558
0.814 Intermediate Similarity NPC470272

  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 NPC471873 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
0.8442 Intermediate Similarity NPD7266 Discontinued
0.8161 Intermediate Similarity NPD8312 Approved
0.8161 Intermediate Similarity NPD8313 Approved
0.8129 Intermediate Similarity NPD7228 Approved
0.7937 Intermediate Similarity NPD8166 Discontinued
0.7931 Intermediate Similarity NPD7074 Phase 3
0.7931 Intermediate Similarity NPD7472 Approved
0.7904 Intermediate Similarity NPD8455 Phase 2
0.7888 Intermediate Similarity NPD6190 Approved
0.7874 Intermediate Similarity NPD7054 Approved
0.7841 Intermediate Similarity NPD7251 Discontinued
0.7797 Intermediate Similarity NPD7808 Phase 3
0.7784 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD6797 Phase 2
0.7765 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7747 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD7240 Approved
0.774 Intermediate Similarity NPD7685 Pre-registration
0.7735 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD6234 Discontinued
0.7714 Intermediate Similarity NPD3818 Discontinued
0.7706 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD37 Approved
0.7602 Intermediate Similarity NPD4967 Phase 2
0.7602 Intermediate Similarity NPD4965 Approved
0.7602 Intermediate Similarity NPD4966 Approved
0.7558 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD6559 Discontinued
0.7529 Intermediate Similarity NPD8127 Discontinued
0.75 Intermediate Similarity NPD6166 Phase 2
0.75 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7472 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD8151 Discontinued
0.7396 Intermediate Similarity NPD8319 Approved
0.7396 Intermediate Similarity NPD8320 Phase 1
0.7396 Intermediate Similarity NPD1653 Approved
0.7365 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7458 Discontinued
0.7344 Intermediate Similarity NPD7680 Approved
0.7337 Intermediate Similarity NPD8434 Phase 2
0.7321 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7699 Phase 2
0.7263 Intermediate Similarity NPD7473 Discontinued
0.7263 Intermediate Similarity NPD7700 Phase 2
0.7254 Intermediate Similarity NPD7435 Discontinued
0.7243 Intermediate Similarity NPD8150 Discontinued
0.7239 Intermediate Similarity NPD7097 Phase 1
0.7225 Intermediate Similarity NPD1934 Approved
0.7222 Intermediate Similarity NPD3751 Discontinued
0.7209 Intermediate Similarity NPD4380 Phase 2
0.7191 Intermediate Similarity NPD6232 Discontinued
0.7186 Intermediate Similarity NPD4628 Phase 3
0.7184 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD7698 Approved
0.7165 Intermediate Similarity NPD7696 Phase 3
0.7165 Intermediate Similarity NPD7697 Approved
0.7135 Intermediate Similarity NPD7199 Phase 2
0.7121 Intermediate Similarity NPD7874 Approved
0.7121 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD7701 Phase 2
0.7105 Intermediate Similarity NPD6534 Approved
0.7105 Intermediate Similarity NPD6535 Approved
0.7098 Intermediate Similarity NPD6782 Approved
0.7098 Intermediate Similarity NPD6779 Approved
0.7098 Intermediate Similarity NPD6781 Approved
0.7098 Intermediate Similarity NPD6776 Approved
0.7098 Intermediate Similarity NPD6780 Approved
0.7098 Intermediate Similarity NPD6777 Approved
0.7098 Intermediate Similarity NPD6778 Approved
0.7095 Intermediate Similarity NPD3787 Discontinued
0.7088 Intermediate Similarity NPD5844 Phase 1
0.7086 Intermediate Similarity NPD1465 Phase 2
0.7062 Intermediate Similarity NPD7075 Discontinued
0.7045 Intermediate Similarity NPD5402 Approved
0.7041 Intermediate Similarity NPD7871 Phase 2
0.7041 Intermediate Similarity NPD7870 Phase 2
0.7035 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD6823 Phase 2
0.7024 Intermediate Similarity NPD6674 Discontinued
0.7012 Intermediate Similarity NPD230 Phase 1
0.7 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7783 Phase 2
0.7 Intermediate Similarity NPD7801 Approved
0.6989 Remote Similarity NPD2801 Approved
0.6963 Remote Similarity NPD6213 Phase 3
0.6963 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6963 Remote Similarity NPD6212 Phase 3
0.6961 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6951 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6951 Remote Similarity NPD1613 Approved
0.6951 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6949 Remote Similarity NPD3817 Phase 2
0.691 Remote Similarity NPD7768 Phase 2
0.691 Remote Similarity NPD3882 Suspended
0.6893 Remote Similarity NPD7819 Suspended
0.6893 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6889 Remote Similarity NPD5494 Approved
0.6882 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6273 Approved
0.6875 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6871 Remote Similarity NPD3027 Phase 3
0.6862 Remote Similarity NPD7090 Clinical (unspecified phase)
0.686 Remote Similarity NPD1511 Approved
0.6854 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6851 Remote Similarity NPD6959 Discontinued
0.6848 Remote Similarity NPD943 Approved
0.6848 Remote Similarity NPD7799 Discontinued
0.6845 Remote Similarity NPD5406 Approved
0.6845 Remote Similarity NPD2935 Discontinued
0.6845 Remote Similarity NPD5404 Approved
0.6845 Remote Similarity NPD5408 Approved
0.6845 Remote Similarity NPD5405 Approved
0.6839 Remote Similarity NPD5403 Approved
0.6831 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6829 Remote Similarity NPD3764 Approved
0.6826 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6811 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6788 Remote Similarity NPD6663 Approved
0.6784 Remote Similarity NPD7003 Approved
0.6784 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6784 Remote Similarity NPD4110 Phase 3
0.6784 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6782 Remote Similarity NPD1512 Approved
0.678 Remote Similarity NPD7411 Suspended
0.6779 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6761 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6761 Remote Similarity NPD3226 Approved
0.6748 Remote Similarity NPD5736 Approved
0.6746 Remote Similarity NPD1551 Phase 2
0.6742 Remote Similarity NPD6801 Discontinued
0.6727 Remote Similarity NPD6798 Discontinued
0.6724 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6724 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6724 Remote Similarity NPD5401 Approved
0.6723 Remote Similarity NPD7028 Phase 2
0.6723 Remote Similarity NPD6599 Discontinued
0.6708 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6355 Discontinued
0.6707 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6707 Remote Similarity NPD1933 Approved
0.6702 Remote Similarity NPD8368 Discontinued
0.6687 Remote Similarity NPD6233 Phase 2
0.6667 Remote Similarity NPD7095 Approved
0.6667 Remote Similarity NPD1549 Phase 2
0.6667 Remote Similarity NPD3455 Phase 2
0.6646 Remote Similarity NPD9494 Approved
0.6646 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6632 Remote Similarity NPD8360 Approved
0.6632 Remote Similarity NPD8361 Approved
0.6628 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6626 Remote Similarity NPD1470 Approved
0.6608 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6608 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6607 Remote Similarity NPD447 Suspended
0.6597 Remote Similarity NPD8407 Phase 2
0.659 Remote Similarity NPD3750 Approved
0.6588 Remote Similarity NPD7033 Discontinued
0.6588 Remote Similarity NPD1510 Phase 2
0.6587 Remote Similarity NPD8404 Phase 2
0.6584 Remote Similarity NPD1091 Approved
0.6584 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6583 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6571 Remote Similarity NPD6799 Approved
0.6566 Remote Similarity NPD5952 Clinical (unspecified phase)
0.655 Remote Similarity NPD9570 Approved
0.6548 Remote Similarity NPD3620 Phase 2
0.6548 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6546 Remote Similarity NPD8435 Approved
0.6543 Remote Similarity NPD9269 Phase 2
0.6527 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6526 Remote Similarity NPD7039 Approved
0.6526 Remote Similarity NPD7038 Approved
0.6519 Remote Similarity NPD5761 Phase 2
0.6519 Remote Similarity NPD5760 Phase 2
0.6512 Remote Similarity NPD2346 Discontinued
0.6503 Remote Similarity NPD3749 Approved
0.65 Remote Similarity NPD6386 Approved
0.65 Remote Similarity NPD7615 Clinical (unspecified phase)
0.65 Remote Similarity NPD6385 Approved
0.6491 Remote Similarity NPD2799 Discontinued
0.649 Remote Similarity NPD7930 Approved
0.6477 Remote Similarity NPD7390 Discontinued
0.6474 Remote Similarity NPD970 Clinical (unspecified phase)
0.6465 Remote Similarity NPD8059 Phase 3
0.6465 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6453 Remote Similarity NPD2438 Suspended
0.6453 Remote Similarity NPD6100 Approved
0.6453 Remote Similarity NPD6099 Approved
0.645 Remote Similarity NPD4060 Phase 1
0.6446 Remote Similarity NPD2861 Phase 2
0.6443 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6441 Remote Similarity NPD2532 Approved
0.6441 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6441 Remote Similarity NPD2534 Approved
0.6441 Remote Similarity NPD2533 Approved
0.6441 Remote Similarity NPD7410 Clinical (unspecified phase)

  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