Structure

Physi-Chem Properties

Molecular Weight:  542.22
Volume:  540.088
LogP:  2.588
LogD:  1.833
LogS:  -3.457
# Rotatable Bonds:  9
TPSA:  162.98
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.244
Synthetic Accessibility Score:  4.532
Fsp3:  0.448
Lipinski Rule-of-5:  Accepted
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:  -6.009
MDCK Permeability:  1.7004173059831373e-05
Pgp-inhibitor:  0.028
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.861
20% Bioavailability (F20%):  0.434
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  95.38330078125%
Volume Distribution (VD):  1.172
Pgp-substrate:  1.965928316116333%

ADMET: Metabolism

CYP1A2-inhibitor:  0.073
CYP1A2-substrate:  0.054
CYP2C19-inhibitor:  0.074
CYP2C19-substrate:  0.206
CYP2C9-inhibitor:  0.15
CYP2C9-substrate:  0.26
CYP2D6-inhibitor:  0.042
CYP2D6-substrate:  0.164
CYP3A4-inhibitor:  0.372
CYP3A4-substrate:  0.301

ADMET: Excretion

Clearance (CL):  5.821
Half-life (T1/2):  0.425

ADMET: Toxicity

hERG Blockers:  0.406
Human Hepatotoxicity (H-HT):  0.739
Drug-inuced Liver Injury (DILI):  0.827
AMES Toxicity:  0.783
Rat Oral Acute Toxicity:  0.143
Maximum Recommended Daily Dose:  0.099
Skin Sensitization:  0.903
Carcinogencity:  0.045
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.045

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Similar NPs/Drugs  

  Natural Product: NPC130489

Natural Product ID:  NPC130489
Common Name*:   (2S,3S)-Pterosin C 3-O-Beta-(4'-P-Coumaroyl)-Glucopyranoside
IUPAC Name:   [(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-[[(1S,2S)-5-(2-hydroxyethyl)-2,4,6-trimethyl-3-oxo-1,2-dihydroinden-1-yl]oxy]-2-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  XHAHKCFIMDRADG-XAPQBWADSA-N
Standard InCHI:  InChI=1S/C29H34O10/c1-14-12-20-23(15(2)19(14)10-11-30)24(34)16(3)27(20)39-29-26(36)25(35)28(21(13-31)37-29)38-22(33)9-6-17-4-7-18(32)8-5-17/h4-9,12,16,21,25-32,35-36H,10-11,13H2,1-3H3/b9-6+/t16-,21-,25-,26-,27+,28-,29+/m1/s1
SMILES:  Cc1cc2c(c(C)c1CCO)C(=O)[C@@H](C)[C@@H]2O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)OC(=O)/C=C/c1ccc(cc1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL401732
PubChem CID:   24800714
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0003002] Hydroxycinnamic acid esters
            • [CHEMONTID:0000465] Coumaric acid esters

*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
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[10556916]
NPO19369 Bacillus thuringiensis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[11087590]
NPO26770 Pteris multifida Species Pteridaceae Eukaryota Whole plant n.a. n.a. PMID[18181575]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[19406895]
NPO3494 Swietenia mahagoni Species Meliaceae Eukaryota fruits n.a. n.a. PMID[19902967]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[19917748]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[20932054]
NPO14077 Chamaecyparis lawsoniana Species Cupressaceae Eukaryota n.a. stem n.a. PMID[23157017]
NPO14077 Chamaecyparis lawsoniana Species Cupressaceae Eukaryota n.a. leaf n.a. PMID[23157017]
NPO11601 Chandonanthus hirtellus Species Anastrophyllaceae Eukaryota n.a. Chinese liverworts n.a. PMID[24491225]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25043228]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25960261]
NPO13626 Aconitum karakolicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Europe PMC[305622]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[32603106]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. Antarctic n.a. PMID[8882433]
NPO26770 Pteris multifida Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13626 Aconitum karakolicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2756 Emerita analoga Species Hippidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2756 Emerita analoga Species Hippidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15094 Coriaria myrtifolia Species Coriariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13626 Aconitum karakolicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26770 Pteris multifida Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13626 Aconitum karakolicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8611 Cornutia grandifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27787 Pseudocentrotus depressus Species Echinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14630 Boronia ramosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14077 Chamaecyparis lawsoniana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15726 Rudbeckia subtomentosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7056 Pedinophyllum interruptum Species Plagiochilaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19369 Bacillus thuringiensis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13626 Aconitum karakolicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11601 Chandonanthus hirtellus Species Anastrophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26770 Pteris multifida Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13236 Viguiera multiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9155 Kageneckia angustifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7868 Xeromphis obovata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13360 Passiflora racemosa Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO3494 Swietenia mahagoni Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8866 Papaver atlanticum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16170 Xerula longipes Species Physalacriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2756 Emerita analoga Species Hippidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2312 Encephalosphaera lasiandra Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15306 Smilax japonica Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15818 Lycianthes marlipoensis Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11567 Picradeniopsis absinthifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15094 Coriaria myrtifolia Species Coriariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1890 Lidbeckia pectinata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12517 Tylophora cordifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12294 Kydia calycina Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10624 Solidago wrightii Species Asteraceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 14160.0 nM PMID[473774]
NPT114 Cell Line LoVo Homo sapiens IC50 = 11280.0 nM PMID[473774]
NPT111 Cell Line K562 Homo sapiens IC50 = 10630.0 nM PMID[473774]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 8690.0 nM PMID[473774]

☑ 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 NPC130489 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 NPC208676
0.9603 High Similarity NPC257847
0.8846 High Similarity NPC289021
0.8846 High Similarity NPC158546
0.872 High Similarity NPC469419
0.8718 High Similarity NPC96599
0.8704 High Similarity NPC477627
0.8688 High Similarity NPC148323
0.8688 High Similarity NPC283480
0.8683 High Similarity NPC195972
0.8671 High Similarity NPC478235
0.8662 High Similarity NPC117346
0.8662 High Similarity NPC35097
0.8662 High Similarity NPC240592
0.8654 High Similarity NPC120728
0.865 High Similarity NPC187934
0.865 High Similarity NPC97637
0.865 High Similarity NPC145847
0.8636 High Similarity NPC202391
0.8636 High Similarity NPC296659
0.8634 High Similarity NPC206641
0.8634 High Similarity NPC208651
0.8625 High Similarity NPC174599
0.8625 High Similarity NPC82190
0.8625 High Similarity NPC192219
0.8616 High Similarity NPC229354
0.8609 High Similarity NPC156393
0.8599 High Similarity NPC478234
0.8599 High Similarity NPC478236
0.8598 High Similarity NPC109990
0.858 High Similarity NPC53139
0.8562 High Similarity NPC205172
0.8562 High Similarity NPC209393
0.8545 High Similarity NPC178281
0.8543 High Similarity NPC471345
0.8516 High Similarity NPC184464
0.8516 High Similarity NPC194938
0.8516 High Similarity NPC251062
0.8509 High Similarity NPC3449
0.8491 Intermediate Similarity NPC475379
0.8481 Intermediate Similarity NPC161955
0.8457 Intermediate Similarity NPC475378
0.8452 Intermediate Similarity NPC478250
0.8452 Intermediate Similarity NPC186296
0.8438 Intermediate Similarity NPC194705
0.8434 Intermediate Similarity NPC478020
0.8434 Intermediate Similarity NPC478022
0.8428 Intermediate Similarity NPC179128
0.8428 Intermediate Similarity NPC267469
0.8428 Intermediate Similarity NPC87630
0.8428 Intermediate Similarity NPC116292
0.8424 Intermediate Similarity NPC146837
0.8424 Intermediate Similarity NPC278329
0.8408 Intermediate Similarity NPC208293
0.8408 Intermediate Similarity NPC473147
0.8405 Intermediate Similarity NPC187205
0.8397 Intermediate Similarity NPC77922
0.8397 Intermediate Similarity NPC473281
0.8395 Intermediate Similarity NPC475484
0.8393 Intermediate Similarity NPC21956
0.8385 Intermediate Similarity NPC474533
0.8385 Intermediate Similarity NPC474534
0.8375 Intermediate Similarity NPC474620
0.8344 Intermediate Similarity NPC10945
0.8333 Intermediate Similarity NPC474622
0.8333 Intermediate Similarity NPC474621
0.8333 Intermediate Similarity NPC63470
0.8324 Intermediate Similarity NPC475161
0.8324 Intermediate Similarity NPC477860
0.8323 Intermediate Similarity NPC137501
0.8323 Intermediate Similarity NPC154262
0.8323 Intermediate Similarity NPC7518
0.8323 Intermediate Similarity NPC469456
0.8323 Intermediate Similarity NPC478026
0.8323 Intermediate Similarity NPC159387
0.8314 Intermediate Similarity NPC469418
0.8313 Intermediate Similarity NPC162569
0.8313 Intermediate Similarity NPC212099
0.8313 Intermediate Similarity NPC101116
0.8313 Intermediate Similarity NPC247219
0.8313 Intermediate Similarity NPC35160
0.8304 Intermediate Similarity NPC68381
0.8302 Intermediate Similarity NPC189631
0.8294 Intermediate Similarity NPC183441
0.8293 Intermediate Similarity NPC329997
0.8293 Intermediate Similarity NPC177742
0.8286 Intermediate Similarity NPC96194
0.8286 Intermediate Similarity NPC299855
0.8274 Intermediate Similarity NPC149002
0.8274 Intermediate Similarity NPC469458
0.8274 Intermediate Similarity NPC88176
0.8274 Intermediate Similarity NPC469396
0.8274 Intermediate Similarity NPC469459
0.8263 Intermediate Similarity NPC161151
0.8258 Intermediate Similarity NPC475299
0.8256 Intermediate Similarity NPC92403
0.8256 Intermediate Similarity NPC76112
0.8256 Intermediate Similarity NPC170018
0.8256 Intermediate Similarity NPC66820
0.8246 Intermediate Similarity NPC199357
0.8246 Intermediate Similarity NPC472054
0.8242 Intermediate Similarity NPC179914
0.8239 Intermediate Similarity NPC473149
0.8239 Intermediate Similarity NPC189704
0.8235 Intermediate Similarity NPC478021
0.8235 Intermediate Similarity NPC298778
0.8221 Intermediate Similarity NPC185103
0.8221 Intermediate Similarity NPC478232
0.8204 Intermediate Similarity NPC471850
0.8204 Intermediate Similarity NPC476011
0.8204 Intermediate Similarity NPC216752
0.8198 Intermediate Similarity NPC474345
0.8194 Intermediate Similarity NPC31745
0.8194 Intermediate Similarity NPC220936
0.8193 Intermediate Similarity NPC138993
0.8193 Intermediate Similarity NPC474936
0.8192 Intermediate Similarity NPC475121
0.8192 Intermediate Similarity NPC476067
0.8187 Intermediate Similarity NPC13989
0.8187 Intermediate Similarity NPC5029
0.8187 Intermediate Similarity NPC76128
0.8187 Intermediate Similarity NPC294501
0.8187 Intermediate Similarity NPC30432
0.8187 Intermediate Similarity NPC111536
0.8187 Intermediate Similarity NPC271385
0.8182 Intermediate Similarity NPC49173
0.8182 Intermediate Similarity NPC257309
0.8182 Intermediate Similarity NPC29552
0.8176 Intermediate Similarity NPC291153
0.8176 Intermediate Similarity NPC246274
0.8176 Intermediate Similarity NPC475539
0.8176 Intermediate Similarity NPC212808
0.8176 Intermediate Similarity NPC119773
0.8176 Intermediate Similarity NPC474268
0.8176 Intermediate Similarity NPC320734
0.8176 Intermediate Similarity NPC143246
0.8171 Intermediate Similarity NPC186746
0.8166 Intermediate Similarity NPC178851
0.8158 Intermediate Similarity NPC471066
0.8158 Intermediate Similarity NPC471095
0.8155 Intermediate Similarity NPC17432
0.8155 Intermediate Similarity NPC327694
0.8153 Intermediate Similarity NPC469623
0.8153 Intermediate Similarity NPC148080
0.815 Intermediate Similarity NPC176246
0.815 Intermediate Similarity NPC475613
0.815 Intermediate Similarity NPC475233
0.815 Intermediate Similarity NPC46958
0.815 Intermediate Similarity NPC475246
0.8148 Intermediate Similarity NPC77310
0.8146 Intermediate Similarity NPC469705
0.8146 Intermediate Similarity NPC17968
0.8146 Intermediate Similarity NPC470122
0.8144 Intermediate Similarity NPC117943
0.8144 Intermediate Similarity NPC471858
0.8144 Intermediate Similarity NPC293568
0.814 Intermediate Similarity NPC203751
0.814 Intermediate Similarity NPC98776
0.8133 Intermediate Similarity NPC314795
0.8125 Intermediate Similarity NPC120536
0.8125 Intermediate Similarity NPC470330
0.8113 Intermediate Similarity NPC475528
0.8113 Intermediate Similarity NPC103910
0.811 Intermediate Similarity NPC469417
0.8107 Intermediate Similarity NPC475738
0.8107 Intermediate Similarity NPC318472
0.8107 Intermediate Similarity NPC99216
0.8107 Intermediate Similarity NPC474301
0.8105 Intermediate Similarity NPC164172
0.8105 Intermediate Similarity NPC114116
0.8101 Intermediate Similarity NPC475213
0.8101 Intermediate Similarity NPC152796
0.8101 Intermediate Similarity NPC204644
0.8095 Intermediate Similarity NPC56735
0.8095 Intermediate Similarity NPC326278
0.8095 Intermediate Similarity NPC61594
0.8095 Intermediate Similarity NPC22324
0.8092 Intermediate Similarity NPC199533
0.8092 Intermediate Similarity NPC193377
0.8092 Intermediate Similarity NPC281798
0.8092 Intermediate Similarity NPC223735
0.8092 Intermediate Similarity NPC470667
0.8092 Intermediate Similarity NPC470454
0.8092 Intermediate Similarity NPC63105
0.8092 Intermediate Similarity NPC307754
0.8092 Intermediate Similarity NPC3718
0.8084 Intermediate Similarity NPC470358
0.8084 Intermediate Similarity NPC328093
0.8081 Intermediate Similarity NPC315619
0.8081 Intermediate Similarity NPC477617
0.8081 Intermediate Similarity NPC148185
0.8077 Intermediate Similarity NPC49597
0.8075 Intermediate Similarity NPC28776
0.8075 Intermediate Similarity NPC471734
0.8075 Intermediate Similarity NPC476173
0.8075 Intermediate Similarity NPC473138
0.8075 Intermediate Similarity NPC81835
0.8072 Intermediate Similarity NPC226759
0.8072 Intermediate Similarity NPC104275
0.8072 Intermediate Similarity NPC43638

  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 NPC130489 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
0.8256 Intermediate Similarity NPD8312 Approved
0.8256 Intermediate Similarity NPD8313 Approved
0.814 Intermediate Similarity NPD7685 Pre-registration
0.8035 Intermediate Similarity NPD6559 Discontinued
0.8034 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD7799 Discontinued
0.7759 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7753 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD7075 Discontinued
0.7736 Intermediate Similarity NPD7266 Discontinued
0.7722 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD4380 Phase 2
0.7709 Intermediate Similarity NPD8150 Discontinued
0.7702 Intermediate Similarity NPD4628 Phase 3
0.7701 Intermediate Similarity NPD7228 Approved
0.7677 Intermediate Similarity NPD3764 Approved
0.766 Intermediate Similarity NPD8320 Phase 1
0.766 Intermediate Similarity NPD8319 Approved
0.7651 Intermediate Similarity NPD7458 Discontinued
0.7644 Intermediate Similarity NPD7473 Discontinued
0.7619 Intermediate Similarity NPD37 Approved
0.7613 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD7435 Discontinued
0.7602 Intermediate Similarity NPD6234 Discontinued
0.76 Intermediate Similarity NPD3818 Discontinued
0.7588 Intermediate Similarity NPD4966 Approved
0.7588 Intermediate Similarity NPD4967 Phase 2
0.7588 Intermediate Similarity NPD4965 Approved
0.7576 Intermediate Similarity NPD6273 Approved
0.7574 Intermediate Similarity NPD7819 Suspended
0.7574 Intermediate Similarity NPD8455 Phase 2
0.7574 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD6535 Approved
0.7554 Intermediate Similarity NPD6534 Approved
0.7527 Intermediate Similarity NPD7699 Phase 2
0.7527 Intermediate Similarity NPD7700 Phase 2
0.7514 Intermediate Similarity NPD7074 Phase 3
0.7471 Intermediate Similarity NPD6232 Discontinued
0.746 Intermediate Similarity NPD6823 Phase 2
0.7458 Intermediate Similarity NPD7054 Approved
0.7447 Intermediate Similarity NPD6778 Approved
0.7447 Intermediate Similarity NPD6782 Approved
0.7447 Intermediate Similarity NPD6781 Approved
0.7447 Intermediate Similarity NPD6776 Approved
0.7447 Intermediate Similarity NPD6777 Approved
0.7447 Intermediate Similarity NPD6780 Approved
0.7447 Intermediate Similarity NPD6779 Approved
0.744 Intermediate Similarity NPD3226 Approved
0.7419 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD7472 Approved
0.7412 Intermediate Similarity NPD6801 Discontinued
0.7409 Intermediate Similarity NPD8151 Discontinued
0.7407 Intermediate Similarity NPD2346 Discontinued
0.7405 Intermediate Similarity NPD6213 Phase 3
0.7405 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD6212 Phase 3
0.7405 Intermediate Similarity NPD6663 Approved
0.7389 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD5736 Approved
0.7371 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7874 Approved
0.736 Intermediate Similarity NPD5844 Phase 1
0.7333 Intermediate Similarity NPD7251 Discontinued
0.7333 Intermediate Similarity NPD7240 Approved
0.733 Intermediate Similarity NPD7697 Approved
0.733 Intermediate Similarity NPD7696 Phase 3
0.733 Intermediate Similarity NPD7698 Approved
0.7326 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7322 Intermediate Similarity NPD8434 Phase 2
0.7314 Intermediate Similarity NPD7199 Phase 2
0.7305 Intermediate Similarity NPD2532 Approved
0.7305 Intermediate Similarity NPD2534 Approved
0.7305 Intermediate Similarity NPD2533 Approved
0.7303 Intermediate Similarity NPD5126 Approved
0.7303 Intermediate Similarity NPD5125 Phase 3
0.7293 Intermediate Similarity NPD7808 Phase 3
0.7292 Intermediate Similarity NPD7871 Phase 2
0.7292 Intermediate Similarity NPD7870 Phase 2
0.7289 Intermediate Similarity NPD7236 Approved
0.7284 Intermediate Similarity NPD2799 Discontinued
0.7278 Intermediate Similarity NPD7239 Suspended
0.7278 Intermediate Similarity NPD6797 Phase 2
0.7268 Intermediate Similarity NPD7701 Phase 2
0.7267 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD7411 Suspended
0.7245 Intermediate Similarity NPD7801 Approved
0.7245 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD7783 Phase 2
0.7239 Intermediate Similarity NPD5404 Approved
0.7239 Intermediate Similarity NPD2935 Discontinued
0.7239 Intermediate Similarity NPD5405 Approved
0.7239 Intermediate Similarity NPD5408 Approved
0.7239 Intermediate Similarity NPD5406 Approved
0.7235 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD6190 Approved
0.7222 Intermediate Similarity NPD7930 Approved
0.7216 Intermediate Similarity NPD8127 Discontinued
0.7216 Intermediate Similarity NPD6959 Discontinued
0.7212 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD5647 Approved
0.7195 Intermediate Similarity NPD5762 Approved
0.7195 Intermediate Similarity NPD5763 Approved
0.7193 Intermediate Similarity NPD6599 Discontinued
0.7184 Intermediate Similarity NPD7768 Phase 2
0.7184 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD8166 Discontinued
0.7169 Intermediate Similarity NPD3750 Approved
0.7169 Intermediate Similarity NPD7003 Approved
0.7168 Intermediate Similarity NPD5761 Phase 2
0.7168 Intermediate Similarity NPD5760 Phase 2
0.7165 Intermediate Similarity NPD7999 Approved
0.7143 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD2438 Suspended
0.7126 Intermediate Similarity NPD5402 Approved
0.7118 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD5403 Approved
0.711 Intermediate Similarity NPD1934 Approved
0.7101 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD6355 Discontinued
0.7095 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD7028 Phase 2
0.7091 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6002 Phase 3
0.7091 Intermediate Similarity NPD6004 Phase 3
0.7091 Intermediate Similarity NPD6005 Phase 3
0.7091 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD1876 Approved
0.7062 Intermediate Similarity NPD5494 Approved
0.7059 Intermediate Similarity NPD9545 Approved
0.7048 Intermediate Similarity NPD1549 Phase 2
0.7045 Intermediate Similarity NPD3749 Approved
0.7041 Intermediate Similarity NPD6799 Approved
0.7025 Intermediate Similarity NPD3094 Phase 2
0.7025 Intermediate Similarity NPD1470 Approved
0.7019 Intermediate Similarity NPD2313 Discontinued
0.701 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6674 Discontinued
0.7 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6166 Phase 2
0.7 Intermediate Similarity NPD5401 Approved
0.7 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.6994 Remote Similarity NPD230 Phase 1
0.699 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6988 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6988 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6981 Remote Similarity NPD2798 Approved
0.6978 Remote Similarity NPD8470 Clinical (unspecified phase)
0.697 Remote Similarity NPD1510 Phase 2
0.6962 Remote Similarity NPD1283 Approved
0.6957 Remote Similarity NPD8368 Discontinued
0.6951 Remote Similarity NPD1607 Approved
0.6951 Remote Similarity NPD6653 Approved
0.6946 Remote Similarity NPD970 Clinical (unspecified phase)
0.6943 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6941 Remote Similarity NPD7390 Discontinued
0.6936 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6935 Remote Similarity NPD8407 Phase 2
0.6933 Remote Similarity NPD2979 Phase 3
0.6933 Remote Similarity NPD4140 Approved
0.6932 Remote Similarity NPD3817 Phase 2
0.6928 Remote Similarity NPD1551 Phase 2
0.6923 Remote Similarity NPD3751 Discontinued
0.6909 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6909 Remote Similarity NPD7097 Phase 1
0.6902 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6901 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6893 Remote Similarity NPD3882 Suspended
0.6889 Remote Similarity NPD5710 Approved
0.6889 Remote Similarity NPD5711 Approved
0.6888 Remote Similarity NPD7680 Approved
0.6886 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1201 Approved
0.6879 Remote Similarity NPD3092 Approved
0.6875 Remote Similarity NPD2801 Approved
0.6875 Remote Similarity NPD1465 Phase 2
0.6875 Remote Similarity NPD6085 Phase 2
0.6875 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7584 Approved
0.6867 Remote Similarity NPD7033 Discontinued
0.6867 Remote Similarity NPD3748 Approved
0.6865 Remote Similarity NPD6764 Approved
0.6865 Remote Similarity NPD6765 Approved
0.6864 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6859 Remote Similarity NPD2932 Approved
0.6859 Remote Similarity NPD3019 Approved
0.6852 Remote Similarity NPD7008 Discontinued
0.6845 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6829 Remote Similarity NPD4060 Phase 1
0.6829 Remote Similarity NPD1240 Approved
0.6826 Remote Similarity NPD2796 Approved
0.6813 Remote Similarity NPD1164 Approved
0.6802 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6802 Remote Similarity NPD7497 Discontinued

  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