Structure

Physi-Chem Properties

Molecular Weight:  633.27
Volume:  640.222
LogP:  1.247
LogD:  2.175
LogS:  -4.952
# Rotatable Bonds:  16
TPSA:  189.84
# H-Bond Aceptor:  12
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.058
Synthetic Accessibility Score:  3.594
Fsp3:  0.294
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.221
MDCK Permeability:  4.118693141208496e-06
Pgp-inhibitor:  0.015
Pgp-substrate:  0.978
Human Intestinal Absorption (HIA):  0.884
20% Bioavailability (F20%):  0.983
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  94.84403228759766%
Volume Distribution (VD):  1.38
Pgp-substrate:  7.180513381958008%

ADMET: Metabolism

CYP1A2-inhibitor:  0.443
CYP1A2-substrate:  0.688
CYP2C19-inhibitor:  0.142
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.073
CYP2C9-substrate:  0.408
CYP2D6-inhibitor:  0.266
CYP2D6-substrate:  0.259
CYP3A4-inhibitor:  0.083
CYP3A4-substrate:  0.115

ADMET: Excretion

Clearance (CL):  4.743
Half-life (T1/2):  0.908

ADMET: Toxicity

hERG Blockers:  0.224
Human Hepatotoxicity (H-HT):  0.307
Drug-inuced Liver Injury (DILI):  0.427
AMES Toxicity:  0.538
Rat Oral Acute Toxicity:  0.015
Maximum Recommended Daily Dose:  0.671
Skin Sensitization:  0.502
Carcinogencity:  0.008
Eye Corrosion:  0.003
Eye Irritation:  0.006
Respiratory Toxicity:  0.036

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

  Natural Product: NPC281629

Natural Product ID:  NPC281629
Common Name*:   (1,2-Trans)-N3-(4-Acetamidobutyl)-1-(3,4-Dihydroxyphenyl)-7-Hydroxy-N2-(4-Hydroxyphenethyl)-6,8-Dimethoxy-1,2-Dihydronaphthalene-2,3-Dicarboxamide
IUPAC Name:   (1S,2R)-3-N-(4-acetamidobutyl)-1-(3,4-dihydroxyphenyl)-7-hydroxy-2-N-[2-(4-hydroxyphenyl)ethyl]-6,8-dimethoxy-1,2-dihydronaphthalene-2,3-dicarboxamide
Synonyms:  
Standard InCHIKey:  GJSJUEUKMKVQLE-JDXGNMNLSA-N
Standard InCHI:  InChI=1S/C34H39N3O9/c1-19(38)35-13-4-5-14-36-33(43)24-16-22-18-27(45-2)31(42)32(46-3)29(22)28(21-8-11-25(40)26(41)17-21)30(24)34(44)37-15-12-20-6-9-23(39)10-7-20/h6-11,16-18,28,30,39-42H,4-5,12-15H2,1-3H3,(H,35,38)(H,36,43)(H,37,44)/t28-,30-/m0/s1
SMILES:  COc1cc2C=C(C(=O)NCCCCN=C(O)C)[C@@H]([C@H](c2c(c1O)OC)c1ccc(c(c1)O)O)C(=NCCc1ccc(cc1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2337117
PubChem CID:   71524310
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO17823 Lycium chinense Species Solanaceae Eukaryota fruits n.a. n.a. PMID[12467621]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. root n.a. PMID[16212233]
NPO17823 Lycium chinense Species Solanaceae Eukaryota root bark n.a. n.a. PMID[23282106]
NPO17823 Lycium chinense Species Solanaceae Eukaryota Root Bark n.a. n.a. PMID[26982999]
NPO17823 Lycium chinense Species Solanaceae Eukaryota fruits n.a. n.a. PMID[9090870]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17823 Lycium chinense Species Solanaceae 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. IC50 = 58000.0 nM PMID[466623]
NPT1 Others Radical scavenging activity IC50 = 67000.0 nM PMID[466623]

☑ 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 NPC281629 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
0.9831 High Similarity NPC469689
0.9831 High Similarity NPC471031
0.9266 High Similarity NPC124626
0.8057 Intermediate Similarity NPC127402
0.8023 Intermediate Similarity NPC107602
0.8 Intermediate Similarity NPC29531
0.7927 Intermediate Similarity NPC471563
0.788 Intermediate Similarity NPC473748
0.7816 Intermediate Similarity NPC82056
0.7778 Intermediate Similarity NPC474507
0.7772 Intermediate Similarity NPC149389
0.7714 Intermediate Similarity NPC5462
0.7709 Intermediate Similarity NPC114124
0.7696 Intermediate Similarity NPC138083
0.7684 Intermediate Similarity NPC99723
0.768 Intermediate Similarity NPC11296
0.768 Intermediate Similarity NPC48490
0.768 Intermediate Similarity NPC175890
0.768 Intermediate Similarity NPC274661
0.768 Intermediate Similarity NPC82457
0.7672 Intermediate Similarity NPC173416
0.7672 Intermediate Similarity NPC476577
0.7672 Intermediate Similarity NPC148709
0.7641 Intermediate Similarity NPC318805
0.7641 Intermediate Similarity NPC60295
0.7641 Intermediate Similarity NPC41122
0.7641 Intermediate Similarity NPC191132
0.7633 Intermediate Similarity NPC38964
0.7611 Intermediate Similarity NPC275027
0.7606 Intermediate Similarity NPC231371
0.7581 Intermediate Similarity NPC90984
0.7579 Intermediate Similarity NPC32064
0.7576 Intermediate Similarity NPC234318
0.7569 Intermediate Similarity NPC78505
0.7542 Intermediate Similarity NPC77598
0.7526 Intermediate Similarity NPC329969
0.7513 Intermediate Similarity NPC30779
0.7513 Intermediate Similarity NPC476565
0.75 Intermediate Similarity NPC329837
0.7487 Intermediate Similarity NPC53146
0.7487 Intermediate Similarity NPC473445
0.7487 Intermediate Similarity NPC286790
0.7487 Intermediate Similarity NPC188120
0.7475 Intermediate Similarity NPC85381
0.7475 Intermediate Similarity NPC256124
0.7474 Intermediate Similarity NPC192135
0.7474 Intermediate Similarity NPC66341
0.7474 Intermediate Similarity NPC477020
0.7463 Intermediate Similarity NPC475654
0.7462 Intermediate Similarity NPC259350
0.7462 Intermediate Similarity NPC223236
0.7461 Intermediate Similarity NPC286119
0.746 Intermediate Similarity NPC26240
0.746 Intermediate Similarity NPC477562
0.746 Intermediate Similarity NPC69712
0.7449 Intermediate Similarity NPC476576
0.7449 Intermediate Similarity NPC208890
0.7449 Intermediate Similarity NPC186546
0.7447 Intermediate Similarity NPC291977
0.7427 Intermediate Similarity NPC46990
0.7423 Intermediate Similarity NPC90998
0.7423 Intermediate Similarity NPC229373
0.7423 Intermediate Similarity NPC8836
0.7423 Intermediate Similarity NPC182052
0.7423 Intermediate Similarity NPC222661
0.7423 Intermediate Similarity NPC49075
0.7423 Intermediate Similarity NPC279228
0.7423 Intermediate Similarity NPC223690
0.7423 Intermediate Similarity NPC271013
0.7423 Intermediate Similarity NPC285931
0.7423 Intermediate Similarity NPC15414
0.7423 Intermediate Similarity NPC328155
0.7423 Intermediate Similarity NPC185639
0.7423 Intermediate Similarity NPC290582
0.7423 Intermediate Similarity NPC104196
0.7423 Intermediate Similarity NPC54654
0.7423 Intermediate Similarity NPC258657
0.7423 Intermediate Similarity NPC311973
0.7423 Intermediate Similarity NPC42663
0.7423 Intermediate Similarity NPC239824
0.7423 Intermediate Similarity NPC251735
0.7423 Intermediate Similarity NPC181796
0.7423 Intermediate Similarity NPC217748
0.7423 Intermediate Similarity NPC7715
0.7423 Intermediate Similarity NPC290005
0.7421 Intermediate Similarity NPC239775
0.7419 Intermediate Similarity NPC60186
0.7419 Intermediate Similarity NPC50380
0.7419 Intermediate Similarity NPC179250
0.7416 Intermediate Similarity NPC16353
0.7411 Intermediate Similarity NPC470642
0.7403 Intermediate Similarity NPC478189
0.7401 Intermediate Similarity NPC472088
0.7401 Intermediate Similarity NPC472087
0.7398 Intermediate Similarity NPC474009
0.7394 Intermediate Similarity NPC223077
0.7394 Intermediate Similarity NPC68328
0.7394 Intermediate Similarity NPC13916
0.7394 Intermediate Similarity NPC193853
0.7394 Intermediate Similarity NPC56887
0.7394 Intermediate Similarity NPC42797
0.7394 Intermediate Similarity NPC264850
0.7387 Intermediate Similarity NPC478092
0.7387 Intermediate Similarity NPC478091
0.7387 Intermediate Similarity NPC30182
0.7387 Intermediate Similarity NPC473589
0.7386 Intermediate Similarity NPC472092
0.7386 Intermediate Similarity NPC472090
0.7386 Intermediate Similarity NPC472091
0.7385 Intermediate Similarity NPC276120
0.7385 Intermediate Similarity NPC254441
0.7385 Intermediate Similarity NPC167116
0.7385 Intermediate Similarity NPC274716
0.7383 Intermediate Similarity NPC252156
0.7382 Intermediate Similarity NPC188079
0.7377 Intermediate Similarity NPC476434
0.7376 Intermediate Similarity NPC242728
0.7371 Intermediate Similarity NPC296898
0.7368 Intermediate Similarity NPC168753
0.7368 Intermediate Similarity NPC118274
0.7368 Intermediate Similarity NPC164608
0.7366 Intermediate Similarity NPC199463
0.7366 Intermediate Similarity NPC37543
0.7366 Intermediate Similarity NPC475768
0.7366 Intermediate Similarity NPC202839
0.7366 Intermediate Similarity NPC178976
0.7366 Intermediate Similarity NPC66678
0.7363 Intermediate Similarity NPC50548
0.736 Intermediate Similarity NPC275680
0.736 Intermediate Similarity NPC283207
0.736 Intermediate Similarity NPC174122
0.736 Intermediate Similarity NPC64140
0.736 Intermediate Similarity NPC22115
0.7356 Intermediate Similarity NPC313081
0.7354 Intermediate Similarity NPC204947
0.735 Intermediate Similarity NPC470646
0.7345 Intermediate Similarity NPC472089
0.734 Intermediate Similarity NPC24465
0.734 Intermediate Similarity NPC209377
0.7337 Intermediate Similarity NPC149889
0.7337 Intermediate Similarity NPC65591
0.7337 Intermediate Similarity NPC178574
0.7337 Intermediate Similarity NPC312338
0.7337 Intermediate Similarity NPC475141
0.7337 Intermediate Similarity NPC478093
0.7326 Intermediate Similarity NPC104876
0.7326 Intermediate Similarity NPC245891
0.7323 Intermediate Similarity NPC206900
0.7323 Intermediate Similarity NPC82763
0.732 Intermediate Similarity NPC243454
0.732 Intermediate Similarity NPC475479
0.7316 Intermediate Similarity NPC26386
0.7313 Intermediate Similarity NPC144314
0.7312 Intermediate Similarity NPC279605
0.7312 Intermediate Similarity NPC470762
0.7312 Intermediate Similarity NPC77807
0.7312 Intermediate Similarity NPC14561
0.7312 Intermediate Similarity NPC474167
0.7312 Intermediate Similarity NPC5379
0.731 Intermediate Similarity NPC212237
0.731 Intermediate Similarity NPC116465
0.731 Intermediate Similarity NPC57036
0.731 Intermediate Similarity NPC234069
0.7308 Intermediate Similarity NPC197125
0.7308 Intermediate Similarity NPC14390
0.7304 Intermediate Similarity NPC244191
0.7303 Intermediate Similarity NPC472410
0.7302 Intermediate Similarity NPC3906
0.7302 Intermediate Similarity NPC475349
0.7302 Intermediate Similarity NPC475565
0.7302 Intermediate Similarity NPC81247
0.7302 Intermediate Similarity NPC476573
0.7302 Intermediate Similarity NPC35627
0.7302 Intermediate Similarity NPC475292
0.7299 Intermediate Similarity NPC209199
0.7297 Intermediate Similarity NPC473736
0.7293 Intermediate Similarity NPC30720
0.7293 Intermediate Similarity NPC262297
0.7292 Intermediate Similarity NPC474051
0.7283 Intermediate Similarity NPC2295
0.7283 Intermediate Similarity NPC477564
0.7283 Intermediate Similarity NPC272566
0.7282 Intermediate Similarity NPC298339
0.7282 Intermediate Similarity NPC239584
0.7282 Intermediate Similarity NPC195538
0.7282 Intermediate Similarity NPC257269
0.7278 Intermediate Similarity NPC207732
0.7277 Intermediate Similarity NPC83019
0.7277 Intermediate Similarity NPC293624
0.7277 Intermediate Similarity NPC43065
0.7273 Intermediate Similarity NPC115281
0.7273 Intermediate Similarity NPC181168
0.7273 Intermediate Similarity NPC163527
0.7269 Intermediate Similarity NPC475624
0.7268 Intermediate Similarity NPC52475
0.7264 Intermediate Similarity NPC149962
0.726 Intermediate Similarity NPC293347
0.7259 Intermediate Similarity NPC16357
0.7259 Intermediate Similarity NPC302245
0.7259 Intermediate Similarity NPC18306

  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 NPC281629 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
0.7921 Intermediate Similarity NPD7827 Phase 1
0.7638 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7604 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7472 Intermediate Similarity NPD4357 Discontinued
0.7423 Intermediate Similarity NPD8054 Approved
0.7423 Intermediate Similarity NPD8053 Approved
0.7421 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD8059 Phase 3
0.736 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD8051 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6618 Phase 2
0.7282 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD7473 Discontinued
0.7273 Intermediate Similarity NPD7801 Approved
0.724 Intermediate Similarity NPD7177 Discontinued
0.7231 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD7047 Phase 3
0.7216 Intermediate Similarity NPD6297 Approved
0.7211 Intermediate Similarity NPD6232 Discontinued
0.7198 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD6146 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7038 Approved
0.7179 Intermediate Similarity NPD7039 Approved
0.7178 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD6973 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD6851 Approved
0.7157 Intermediate Similarity NPD6853 Approved
0.715 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7549 Discontinued
0.7143 Intermediate Similarity NPD6234 Discontinued
0.7136 Intermediate Similarity NPD7291 Discontinued
0.7136 Intermediate Similarity NPD8149 Discontinued
0.7136 Intermediate Similarity NPD7693 Approved
0.7136 Intermediate Similarity NPD6823 Phase 2
0.7112 Intermediate Similarity NPD4585 Approved
0.7097 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD5089 Approved
0.7097 Intermediate Similarity NPD6997 Phase 2
0.7097 Intermediate Similarity NPD5090 Approved
0.7097 Intermediate Similarity NPD7110 Phase 1
0.709 Intermediate Similarity NPD4055 Discovery
0.7081 Intermediate Similarity NPD824 Approved
0.7072 Intermediate Similarity NPD2219 Phase 1
0.7065 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD8252 Approved
0.7062 Intermediate Similarity NPD7228 Approved
0.7062 Intermediate Similarity NPD8251 Approved
0.7062 Intermediate Similarity NPD8099 Discontinued
0.7059 Intermediate Similarity NPD37 Approved
0.7051 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD7906 Approved
0.7047 Intermediate Similarity NPD3451 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD6894 Phase 1
0.7043 Intermediate Similarity NPD6876 Approved
0.7043 Intermediate Similarity NPD6875 Approved
0.704 Intermediate Similarity NPD6723 Discontinued
0.7037 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD7608 Discontinued
0.7026 Intermediate Similarity NPD8156 Discontinued
0.702 Intermediate Similarity NPD5035 Approved
0.7016 Intermediate Similarity NPD6746 Phase 2
0.7014 Intermediate Similarity NPD8151 Discontinued
0.7005 Intermediate Similarity NPD2494 Approved
0.7005 Intermediate Similarity NPD2493 Approved
0.7005 Intermediate Similarity NPD3452 Approved
0.7005 Intermediate Similarity NPD3450 Approved
0.7 Intermediate Similarity NPD7584 Approved
0.6989 Remote Similarity NPD4005 Discontinued
0.6989 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6986 Remote Similarity NPD4582 Approved
0.6986 Remote Similarity NPD4583 Approved
0.698 Remote Similarity NPD2490 Approved
0.698 Remote Similarity NPD2488 Approved
0.6961 Remote Similarity NPD3060 Approved
0.6959 Remote Similarity NPD8318 Clinical (unspecified phase)
0.6947 Remote Similarity NPD4966 Approved
0.6947 Remote Similarity NPD4967 Phase 2
0.6947 Remote Similarity NPD4965 Approved
0.694 Remote Similarity NPD7124 Phase 2
0.6939 Remote Similarity NPD42 Phase 2
0.6939 Remote Similarity NPD6042 Phase 2
0.6939 Remote Similarity NPD5844 Phase 1
0.6938 Remote Similarity NPD4002 Approved
0.6938 Remote Similarity NPD4004 Approved
0.6931 Remote Similarity NPD7861 Discontinued
0.6927 Remote Similarity NPD4666 Phase 3
0.6927 Remote Similarity NPD7201 Clinical (unspecified phase)
0.6915 Remote Similarity NPD6385 Approved
0.6915 Remote Similarity NPD6072 Discontinued
0.6915 Remote Similarity NPD8150 Discontinued
0.6915 Remote Similarity NPD6386 Approved
0.6915 Remote Similarity NPD6873 Phase 2
0.6911 Remote Similarity NPD7831 Phase 2
0.6911 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6911 Remote Similarity NPD7833 Phase 2
0.6907 Remote Similarity NPD5242 Approved
0.6902 Remote Similarity NPD5297 Approved
0.6895 Remote Similarity NPD5978 Approved
0.6895 Remote Similarity NPD5977 Approved
0.6895 Remote Similarity NPD7907 Approved
0.6887 Remote Similarity NPD7585 Approved
0.6884 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6884 Remote Similarity NPD5032 Approved
0.6878 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6878 Remote Similarity NPD7248 Discontinued
0.6875 Remote Similarity NPD5709 Phase 3
0.6872 Remote Similarity NPD2898 Approved
0.6872 Remote Similarity NPD6166 Phase 2
0.6872 Remote Similarity NPD27 Approved
0.6872 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6872 Remote Similarity NPD2489 Approved
0.6872 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6869 Remote Similarity NPD6996 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7783 Phase 2
0.6866 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6865 Remote Similarity NPD1424 Approved
0.6862 Remote Similarity NPD4675 Approved
0.6862 Remote Similarity NPD4678 Approved
0.6861 Remote Similarity NPD7654 Discontinued
0.6859 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6859 Remote Similarity NPD6788 Approved
0.685 Remote Similarity NPD7312 Approved
0.685 Remote Similarity NPD7313 Approved
0.685 Remote Similarity NPD7310 Approved
0.685 Remote Similarity NPD7311 Approved
0.6847 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6842 Remote Similarity NPD1465 Phase 2
0.6842 Remote Similarity NPD2801 Approved
0.684 Remote Similarity NPD7583 Approved
0.6836 Remote Similarity NPD2674 Phase 3
0.6825 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6825 Remote Similarity NPD4040 Phase 1
0.6825 Remote Similarity NPD7871 Phase 2
0.6825 Remote Similarity NPD7870 Phase 2
0.6821 Remote Similarity NPD2970 Approved
0.6821 Remote Similarity NPD2969 Approved
0.6816 Remote Similarity NPD7309 Approved
0.6812 Remote Similarity NPD2975 Approved
0.6812 Remote Similarity NPD2973 Approved
0.6812 Remote Similarity NPD2974 Approved
0.6804 Remote Similarity NPD7199 Phase 2
0.68 Remote Similarity NPD4955 Approved
0.68 Remote Similarity NPD4954 Approved
0.68 Remote Similarity NPD5028 Approved
0.68 Remote Similarity NPD5026 Approved
0.68 Remote Similarity NPD4419 Clinical (unspecified phase)
0.68 Remote Similarity NPD5034 Approved
0.68 Remote Similarity NPD36 Approved
0.68 Remote Similarity NPD7190 Clinical (unspecified phase)
0.6798 Remote Similarity NPD7048 Phase 3
0.6796 Remote Similarity NPD3473 Clinical (unspecified phase)
0.6794 Remote Similarity NPD4580 Approved
0.6794 Remote Similarity NPD6782 Approved
0.6794 Remote Similarity NPD6776 Approved
0.6794 Remote Similarity NPD6780 Approved
0.6794 Remote Similarity NPD6781 Approved
0.6794 Remote Similarity NPD6778 Approved
0.6794 Remote Similarity NPD6779 Approved
0.6794 Remote Similarity NPD6777 Approved
0.6789 Remote Similarity NPD1934 Approved
0.6789 Remote Similarity NPD7298 Approved
0.6789 Remote Similarity NPD5722 Discontinued
0.6789 Remote Similarity NPD7945 Clinical (unspecified phase)
0.678 Remote Similarity NPD3145 Approved
0.678 Remote Similarity NPD3144 Approved
0.6777 Remote Similarity NPD7697 Approved
0.6777 Remote Similarity NPD7696 Phase 3
0.6777 Remote Similarity NPD7698 Approved
0.6774 Remote Similarity NPD7447 Phase 1
0.6774 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6772 Remote Similarity NPD6502 Phase 2
0.6771 Remote Similarity NPD3882 Suspended
0.6769 Remote Similarity NPD3051 Approved
0.6768 Remote Similarity NPD6020 Phase 2
0.6766 Remote Similarity NPD4577 Approved
0.6766 Remote Similarity NPD4578 Approved
0.6761 Remote Similarity NPD7263 Phase 2
0.6758 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6754 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6751 Remote Similarity NPD3489 Phase 3
0.675 Remote Similarity NPD5029 Approved
0.675 Remote Similarity NPD5192 Clinical (unspecified phase)
0.675 Remote Similarity NPD5027 Approved
0.675 Remote Similarity NPD5031 Approved
0.675 Remote Similarity NPD5030 Phase 2
0.6749 Remote Similarity NPD4663 Approved
0.6749 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6749 Remote Similarity NPD5037 Approved
0.6749 Remote Similarity NPD5038 Approved
0.6748 Remote Similarity NPD4466 Phase 1
0.674 Remote Similarity NPD7922 Phase 1
0.6737 Remote Similarity NPD7193 Clinical (unspecified phase)
0.6736 Remote Similarity NPD6971 Discontinued
0.6735 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6732 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6731 Remote Similarity NPD7282 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