Structure

Physi-Chem Properties

Molecular Weight:  1030.37
Volume:  987.282
LogP:  -0.359
LogD:  -0.427
LogS:  -2.53
# Rotatable Bonds:  21
TPSA:  386.65
# H-Bond Aceptor:  23
# H-Bond Donor:  13
# Rings:  6
# Heavy Atoms:  23

MedChem Properties

QED Drug-Likeness Score:  0.019
Synthetic Accessibility Score:  6.767
Fsp3:  0.52
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:  -6.811
MDCK Permeability:  2.5145525796688162e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.998
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.177
Plasma Protein Binding (PPB):  67.97826385498047%
Volume Distribution (VD):  0.342
Pgp-substrate:  21.46982765197754%

ADMET: Metabolism

CYP1A2-inhibitor:  0.119
CYP1A2-substrate:  0.044
CYP2C19-inhibitor:  0.006
CYP2C19-substrate:  0.044
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.049
CYP2D6-inhibitor:  0.056
CYP2D6-substrate:  0.027
CYP3A4-inhibitor:  0.38
CYP3A4-substrate:  0.026

ADMET: Excretion

Clearance (CL):  1.092
Half-life (T1/2):  0.838

ADMET: Toxicity

hERG Blockers:  0.187
Human Hepatotoxicity (H-HT):  0.419
Drug-inuced Liver Injury (DILI):  0.026
AMES Toxicity:  0.069
Rat Oral Acute Toxicity:  0.011
Maximum Recommended Daily Dose:  0.962
Skin Sensitization:  0.961
Carcinogencity:  0.533
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.834

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

  Natural Product: NPC471869

Natural Product ID:  NPC471869
Common Name*:   Canangalignan I
IUPAC Name:   bis[[(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] (2E,3E)-2-[(3,4-dihydroxyphenyl)methylidene]-3-[(4-hydroxyphenyl)methylidene]butanedioate
Synonyms:  
Standard InCHIKey:  SIQDQQORHFTLPF-FHCSODAXSA-N
Standard InCHI:  InChI=1S/C50H62O23/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/h1-6,11-17,24-25,28-29,35-44,47-48,51-52,55-65H,7-10,18-23H2/b13-11-,14-12-,31-15+,32-16+/t28-,29-,35+,36+,37-,38-,39+,40+,41-,42-,43+,44+,47+,48+,49+,50+/m0/s1
SMILES:  OC[C@H]1O[C@@H](O/C=C[C@@]2(C=O)CC[C@@H](C[C@@H]2O)COC(=O)/C(=C/c2ccc(c(c2)O)O)/C(=Cc2ccc(cc2)O)/C(=O)OC[C@H]2CC[C@]([C@H](C2)O)(C=O)/C=CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3262191
PubChem CID:   90676277
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 = 28.6 % PMID[489565]
NPT2 Others Unspecified Inhibition = 30.2 % PMID[489565]
NPT2 Others Unspecified Inhibition = 31.8 % PMID[489565]
NPT2 Others Unspecified Inhibition = 34.8 % PMID[489565]
NPT2 Others Unspecified Inhibition = 16.7 % PMID[489565]
NPT2 Others Unspecified Inhibition > 100.0 % PMID[489565]
NPT27 Others Unspecified Activity > 95.2 % PMID[489565]

☑ 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 NPC471869 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 NPC471873
0.962 High Similarity NPC471870
0.9441 High Similarity NPC471871
0.9412 High Similarity NPC471874
0.9342 High Similarity NPC12006
0.9038 High Similarity NPC87403
0.8974 High Similarity NPC106818
0.8931 High Similarity NPC471878
0.8839 High Similarity NPC473138
0.8839 High Similarity NPC28776
0.8683 High Similarity NPC469773
0.8683 High Similarity NPC32723
0.8683 High Similarity NPC469778
0.8683 High Similarity NPC469772
0.8683 High Similarity NPC100925
0.8683 High Similarity NPC469776
0.8683 High Similarity NPC469775
0.8683 High Similarity NPC135334
0.8683 High Similarity NPC295941
0.8683 High Similarity NPC469774
0.8683 High Similarity NPC469777
0.8571 High Similarity NPC131532
0.8562 High Similarity NPC471875
0.8516 High Similarity NPC476380
0.8516 High Similarity NPC298257
0.8516 High Similarity NPC476378
0.8516 High Similarity NPC476384
0.8516 High Similarity NPC119537
0.8516 High Similarity NPC205864
0.8516 High Similarity NPC247032
0.8516 High Similarity NPC476375
0.8516 High Similarity NPC476381
0.8516 High Similarity NPC112
0.8516 High Similarity NPC269141
0.8516 High Similarity NPC96795
0.8516 High Similarity NPC264632
0.8516 High Similarity NPC476397
0.8516 High Similarity NPC175214
0.8516 High Similarity NPC76406
0.8506 High Similarity NPC47471
0.8506 High Similarity NPC476377
0.8503 High Similarity NPC128403
0.8497 Intermediate Similarity NPC205195
0.8481 Intermediate Similarity NPC23677
0.8471 Intermediate Similarity NPC473630
0.8462 Intermediate Similarity NPC64195
0.8442 Intermediate Similarity NPC475530
0.8442 Intermediate Similarity NPC473799
0.8434 Intermediate Similarity NPC227297
0.8431 Intermediate Similarity NPC260425
0.8412 Intermediate Similarity NPC124828
0.8397 Intermediate Similarity NPC105005
0.8387 Intermediate Similarity NPC476385
0.8387 Intermediate Similarity NPC134405
0.8377 Intermediate Similarity NPC81515
0.8377 Intermediate Similarity NPC197316
0.8377 Intermediate Similarity NPC472350
0.8377 Intermediate Similarity NPC89105
0.8377 Intermediate Similarity NPC64141
0.8377 Intermediate Similarity NPC476383
0.8377 Intermediate Similarity NPC68092
0.8375 Intermediate Similarity NPC69367
0.8373 Intermediate Similarity NPC246024
0.8364 Intermediate Similarity NPC44507
0.8354 Intermediate Similarity NPC229505
0.8354 Intermediate Similarity NPC172419
0.8354 Intermediate Similarity NPC238419
0.8344 Intermediate Similarity NPC296954
0.8344 Intermediate Similarity NPC300894
0.8344 Intermediate Similarity NPC141455
0.8344 Intermediate Similarity NPC196063
0.8343 Intermediate Similarity NPC472133
0.8333 Intermediate Similarity NPC265648
0.8333 Intermediate Similarity NPC222433
0.8313 Intermediate Similarity NPC470933
0.8313 Intermediate Similarity NPC476398
0.8313 Intermediate Similarity NPC259347
0.8313 Intermediate Similarity NPC476386
0.8313 Intermediate Similarity NPC94871
0.8313 Intermediate Similarity NPC473427
0.8313 Intermediate Similarity NPC132737
0.8313 Intermediate Similarity NPC471062
0.8313 Intermediate Similarity NPC306890
0.8312 Intermediate Similarity NPC78363
0.8312 Intermediate Similarity NPC476376
0.8303 Intermediate Similarity NPC318826
0.8303 Intermediate Similarity NPC210501
0.8303 Intermediate Similarity NPC104222
0.8303 Intermediate Similarity NPC114791
0.8303 Intermediate Similarity NPC141331
0.8303 Intermediate Similarity NPC469654
0.8301 Intermediate Similarity NPC476870
0.8294 Intermediate Similarity NPC43434
0.8294 Intermediate Similarity NPC472129
0.8293 Intermediate Similarity NPC247629
0.8293 Intermediate Similarity NPC239019
0.8282 Intermediate Similarity NPC472127
0.8282 Intermediate Similarity NPC160882
0.8282 Intermediate Similarity NPC472128
0.8266 Intermediate Similarity NPC469418
0.8261 Intermediate Similarity NPC476871
0.8261 Intermediate Similarity NPC470927
0.8261 Intermediate Similarity NPC257970
0.8258 Intermediate Similarity NPC220942
0.8258 Intermediate Similarity NPC324262
0.8258 Intermediate Similarity NPC62800
0.8247 Intermediate Similarity NPC470572
0.8246 Intermediate Similarity NPC13989
0.8242 Intermediate Similarity NPC187205
0.8242 Intermediate Similarity NPC40920
0.8242 Intermediate Similarity NPC223335
0.8235 Intermediate Similarity NPC658
0.8235 Intermediate Similarity NPC287597
0.8235 Intermediate Similarity NPC34293
0.8235 Intermediate Similarity NPC886
0.8235 Intermediate Similarity NPC197708
0.8228 Intermediate Similarity NPC476867
0.8228 Intermediate Similarity NPC183824
0.8225 Intermediate Similarity NPC469419
0.8221 Intermediate Similarity NPC61152
0.8221 Intermediate Similarity NPC473544
0.8221 Intermediate Similarity NPC16024
0.8221 Intermediate Similarity NPC83663
0.8221 Intermediate Similarity NPC205037
0.8221 Intermediate Similarity NPC266084
0.8221 Intermediate Similarity NPC475162
0.8221 Intermediate Similarity NPC3746
0.8221 Intermediate Similarity NPC44260
0.8221 Intermediate Similarity NPC475216
0.8221 Intermediate Similarity NPC475595
0.8221 Intermediate Similarity NPC475145
0.8217 Intermediate Similarity NPC296643
0.8214 Intermediate Similarity NPC121290
0.8214 Intermediate Similarity NPC25889
0.821 Intermediate Similarity NPC125823
0.821 Intermediate Similarity NPC7145
0.821 Intermediate Similarity NPC85192
0.821 Intermediate Similarity NPC143480
0.8199 Intermediate Similarity NPC478242
0.8187 Intermediate Similarity NPC232992
0.8187 Intermediate Similarity NPC322660
0.8187 Intermediate Similarity NPC472803
0.8187 Intermediate Similarity NPC179240
0.8182 Intermediate Similarity NPC123988
0.8182 Intermediate Similarity NPC103398
0.8182 Intermediate Similarity NPC180171
0.8182 Intermediate Similarity NPC158325
0.8176 Intermediate Similarity NPC34587
0.8176 Intermediate Similarity NPC100998
0.8176 Intermediate Similarity NPC476866
0.8176 Intermediate Similarity NPC476868
0.8176 Intermediate Similarity NPC476382
0.8176 Intermediate Similarity NPC476864
0.8176 Intermediate Similarity NPC311389
0.8176 Intermediate Similarity NPC476869
0.8176 Intermediate Similarity NPC252292
0.8176 Intermediate Similarity NPC470271
0.8176 Intermediate Similarity NPC34927
0.8176 Intermediate Similarity NPC53520
0.8171 Intermediate Similarity NPC469371
0.8166 Intermediate Similarity NPC472130
0.8166 Intermediate Similarity NPC472131
0.8165 Intermediate Similarity NPC285550
0.8165 Intermediate Similarity NPC40305
0.816 Intermediate Similarity NPC478268
0.8155 Intermediate Similarity NPC145847
0.8148 Intermediate Similarity NPC188393
0.8148 Intermediate Similarity NPC470934
0.8141 Intermediate Similarity NPC321184
0.8141 Intermediate Similarity NPC321638
0.8141 Intermediate Similarity NPC328273
0.8141 Intermediate Similarity NPC171134
0.814 Intermediate Similarity NPC47140
0.814 Intermediate Similarity NPC477617
0.814 Intermediate Similarity NPC5786
0.814 Intermediate Similarity NPC102851
0.814 Intermediate Similarity NPC67134
0.8137 Intermediate Similarity NPC192763
0.8137 Intermediate Similarity NPC215095
0.8137 Intermediate Similarity NPC28651
0.8137 Intermediate Similarity NPC261122
0.8137 Intermediate Similarity NPC116229
0.8137 Intermediate Similarity NPC199311
0.8137 Intermediate Similarity NPC80732
0.8137 Intermediate Similarity NPC300262
0.8137 Intermediate Similarity NPC201148
0.8137 Intermediate Similarity NPC210611
0.8137 Intermediate Similarity NPC3460
0.8133 Intermediate Similarity NPC133984
0.8129 Intermediate Similarity NPC95421
0.8129 Intermediate Similarity NPC198125
0.8125 Intermediate Similarity NPC320734
0.8125 Intermediate Similarity NPC476865
0.8121 Intermediate Similarity NPC475484
0.8118 Intermediate Similarity NPC175793
0.8114 Intermediate Similarity NPC195114
0.8113 Intermediate Similarity NPC471876
0.8111 Intermediate Similarity NPC475299
0.811 Intermediate Similarity NPC245615
0.811 Intermediate Similarity NPC115466

  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 NPC471869 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
0.8377 Intermediate Similarity NPD7266 Discontinued
0.8103 Intermediate Similarity NPD8312 Approved
0.8103 Intermediate Similarity NPD8313 Approved
0.807 Intermediate Similarity NPD7228 Approved
0.7937 Intermediate Similarity NPD6190 Approved
0.7875 Intermediate Similarity NPD8166 Discontinued
0.7874 Intermediate Similarity NPD7074 Phase 3
0.7874 Intermediate Similarity NPD7472 Approved
0.7844 Intermediate Similarity NPD8455 Phase 2
0.7816 Intermediate Similarity NPD7054 Approved
0.7784 Intermediate Similarity NPD7251 Discontinued
0.7784 Intermediate Similarity NPD7685 Pre-registration
0.774 Intermediate Similarity NPD7808 Phase 3
0.7727 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD6797 Phase 2
0.7709 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD7240 Approved
0.768 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD6234 Discontinued
0.7657 Intermediate Similarity NPD3818 Discontinued
0.7647 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD37 Approved
0.7544 Intermediate Similarity NPD4965 Approved
0.7544 Intermediate Similarity NPD4966 Approved
0.7544 Intermediate Similarity NPD4967 Phase 2
0.75 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD6559 Discontinued
0.7471 Intermediate Similarity NPD8127 Discontinued
0.7443 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD6166 Phase 2
0.7443 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD1653 Approved
0.7416 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD8151 Discontinued
0.7344 Intermediate Similarity NPD8320 Phase 1
0.7344 Intermediate Similarity NPD8319 Approved
0.7305 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD7458 Discontinued
0.7292 Intermediate Similarity NPD7680 Approved
0.7283 Intermediate Similarity NPD8434 Phase 2
0.7263 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD7700 Phase 2
0.7211 Intermediate Similarity NPD7699 Phase 2
0.7207 Intermediate Similarity NPD7473 Discontinued
0.7202 Intermediate Similarity NPD7435 Discontinued
0.7189 Intermediate Similarity NPD8150 Discontinued
0.7178 Intermediate Similarity NPD7097 Phase 1
0.7168 Intermediate Similarity NPD1934 Approved
0.7167 Intermediate Similarity NPD3751 Discontinued
0.7151 Intermediate Similarity NPD4380 Phase 2
0.7135 Intermediate Similarity NPD6232 Discontinued
0.7126 Intermediate Similarity NPD4628 Phase 3
0.7126 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD7696 Phase 3
0.7113 Intermediate Similarity NPD7698 Approved
0.7113 Intermediate Similarity NPD7697 Approved
0.7079 Intermediate Similarity NPD7199 Phase 2
0.7071 Intermediate Similarity NPD7874 Approved
0.7071 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7701 Phase 2
0.7055 Intermediate Similarity NPD230 Phase 1
0.7053 Intermediate Similarity NPD6535 Approved
0.7053 Intermediate Similarity NPD6534 Approved
0.7047 Intermediate Similarity NPD6777 Approved
0.7047 Intermediate Similarity NPD6776 Approved
0.7047 Intermediate Similarity NPD6779 Approved
0.7047 Intermediate Similarity NPD6778 Approved
0.7047 Intermediate Similarity NPD6780 Approved
0.7047 Intermediate Similarity NPD6781 Approved
0.7047 Intermediate Similarity NPD6782 Approved
0.7039 Intermediate Similarity NPD3787 Discontinued
0.7033 Intermediate Similarity NPD5844 Phase 1
0.7029 Intermediate Similarity NPD1465 Phase 2
0.7006 Intermediate Similarity NPD7075 Discontinued
0.699 Remote Similarity NPD7870 Phase 2
0.699 Remote Similarity NPD7871 Phase 2
0.6989 Remote Similarity NPD5402 Approved
0.6977 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6974 Remote Similarity NPD6823 Phase 2
0.6964 Remote Similarity NPD6674 Discontinued
0.695 Remote Similarity NPD7783 Phase 2
0.695 Remote Similarity NPD7801 Approved
0.695 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6932 Remote Similarity NPD2801 Approved
0.6911 Remote Similarity NPD6212 Phase 3
0.6911 Remote Similarity NPD6213 Phase 3
0.6911 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6906 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6893 Remote Similarity NPD3817 Phase 2
0.689 Remote Similarity NPD1612 Clinical (unspecified phase)
0.689 Remote Similarity NPD7966 Clinical (unspecified phase)
0.689 Remote Similarity NPD1613 Approved
0.6854 Remote Similarity NPD3882 Suspended
0.6854 Remote Similarity NPD7768 Phase 2
0.6836 Remote Similarity NPD7819 Suspended
0.6836 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6833 Remote Similarity NPD5494 Approved
0.6827 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6824 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6273 Approved
0.681 Remote Similarity NPD3027 Phase 3
0.6809 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6802 Remote Similarity NPD1511 Approved
0.6798 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6796 Remote Similarity NPD6959 Discontinued
0.6793 Remote Similarity NPD7799 Discontinued
0.6788 Remote Similarity NPD943 Approved
0.6786 Remote Similarity NPD5406 Approved
0.6786 Remote Similarity NPD1551 Phase 2
0.6786 Remote Similarity NPD5408 Approved
0.6786 Remote Similarity NPD5404 Approved
0.6786 Remote Similarity NPD5405 Approved
0.6786 Remote Similarity NPD2935 Discontinued
0.6782 Remote Similarity NPD5403 Approved
0.6776 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6768 Remote Similarity NPD3764 Approved
0.6766 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6757 Remote Similarity NPD8470 Clinical (unspecified phase)
0.675 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6747 Remote Similarity NPD1933 Approved
0.6731 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6663 Approved
0.6725 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6725 Remote Similarity NPD4110 Phase 3
0.6725 Remote Similarity NPD7003 Approved
0.6725 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6724 Remote Similarity NPD1512 Approved
0.6723 Remote Similarity NPD7411 Suspended
0.6705 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6705 Remote Similarity NPD3226 Approved
0.6687 Remote Similarity NPD5736 Approved
0.6687 Remote Similarity NPD9494 Approved
0.6685 Remote Similarity NPD6801 Discontinued
0.6667 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7028 Phase 2
0.6667 Remote Similarity NPD6599 Discontinued
0.6667 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6798 Discontinued
0.6667 Remote Similarity NPD5401 Approved
0.6649 Remote Similarity NPD8368 Discontinued
0.6647 Remote Similarity NPD6355 Discontinued
0.6647 Remote Similarity NPD447 Suspended
0.6646 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6627 Remote Similarity NPD6233 Phase 2
0.6625 Remote Similarity NPD1091 Approved
0.661 Remote Similarity NPD3455 Phase 2
0.6608 Remote Similarity NPD1549 Phase 2
0.6606 Remote Similarity NPD7095 Approved
0.6585 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6584 Remote Similarity NPD9269 Phase 2
0.658 Remote Similarity NPD8361 Approved
0.658 Remote Similarity NPD8360 Approved
0.657 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6564 Remote Similarity NPD1470 Approved
0.655 Remote Similarity NPD1550 Clinical (unspecified phase)
0.655 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6545 Remote Similarity NPD8407 Phase 2
0.6538 Remote Similarity NPD8404 Phase 2
0.6535 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6533 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6532 Remote Similarity NPD3750 Approved
0.6529 Remote Similarity NPD1510 Phase 2
0.6529 Remote Similarity NPD7033 Discontinued
0.6514 Remote Similarity NPD6799 Approved
0.6506 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6495 Remote Similarity NPD8435 Approved
0.6491 Remote Similarity NPD9570 Approved
0.6488 Remote Similarity NPD3620 Phase 2
0.6488 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6478 Remote Similarity NPD9545 Approved
0.6474 Remote Similarity NPD7039 Approved
0.6474 Remote Similarity NPD7038 Approved
0.6467 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6464 Remote Similarity NPD5761 Phase 2
0.6464 Remote Similarity NPD5760 Phase 2
0.6453 Remote Similarity NPD2346 Discontinued
0.6448 Remote Similarity NPD3749 Approved
0.6444 Remote Similarity NPD6385 Approved
0.6444 Remote Similarity NPD6386 Approved
0.6444 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6442 Remote Similarity NPD7930 Approved
0.6438 Remote Similarity NPD1357 Approved
0.6433 Remote Similarity NPD2799 Discontinued
0.6429 Remote Similarity NPD5353 Approved
0.642 Remote Similarity NPD7390 Discontinued
0.6419 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6419 Remote Similarity NPD8059 Phase 3
0.6416 Remote Similarity NPD970 Clinical (unspecified phase)
0.6395 Remote Similarity NPD2438 Suspended
0.6395 Remote Similarity NPD6100 Approved
0.6395 Remote Similarity NPD6099 Approved
0.6392 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6391 Remote Similarity NPD4060 Phase 1
0.6386 Remote Similarity NPD2861 Phase 2
0.6384 Remote Similarity NPD2533 Approved
0.6384 Remote Similarity NPD2534 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