Structure

Physi-Chem Properties

Molecular Weight:  742.38
Volume:  744.793
LogP:  4.664
LogD:  3.042
LogS:  -5.071
# Rotatable Bonds:  24
TPSA:  207.49
# H-Bond Aceptor:  15
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.152
Synthetic Accessibility Score:  5.393
Fsp3:  0.784
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.711
MDCK Permeability:  0.0001134744961746037
Pgp-inhibitor:  1.0
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.063
20% Bioavailability (F20%):  0.098
30% Bioavailability (F30%):  0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.371
Plasma Protein Binding (PPB):  83.36251068115234%
Volume Distribution (VD):  0.859
Pgp-substrate:  6.427700996398926%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.013
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.314
CYP2C9-inhibitor:  0.151
CYP2C9-substrate:  0.059
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.015
CYP3A4-inhibitor:  0.355
CYP3A4-substrate:  0.476

ADMET: Excretion

Clearance (CL):  4.748
Half-life (T1/2):  0.042

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.901
Drug-inuced Liver Injury (DILI):  0.953
AMES Toxicity:  0.869
Rat Oral Acute Toxicity:  0.251
Maximum Recommended Daily Dose:  0.164
Skin Sensitization:  0.296
Carcinogencity:  0.827
Eye Corrosion:  0.01
Eye Irritation:  0.054
Respiratory Toxicity:  0.029

Download Data

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

  Natural Product: NPC476230

Natural Product ID:  NPC476230
Common Name*:   Valeriotetrate A
IUPAC Name:   [(1S,4aR,6S,7R,7aS)-6-acetyloxy-4a,7-dihydroxy-1-(3-methylbutanoyloxy)-7-[[3-methyl-2-(3-methylbutanoyloxy)butanoyl]oxymethyl]-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-yl]methyl 3-methyl-2-(3-methylbutanoyloxy)butanoate
Synonyms:   Valeriotetrate A
Standard InCHIKey:  MEOWJLHAENRYDE-LDWOCZHXSA-N
Standard InCHI:  InChI=1S/C37H58O15/c1-19(2)12-27(39)50-30(22(7)8)33(42)46-16-25-17-47-35(52-29(41)14-21(5)6)32-36(25,44)15-26(49-24(11)38)37(32,45)18-48-34(43)31(23(9)10)51-28(40)13-20(3)4/h17,19-23,26,30-32,35,44-45H,12-16,18H2,1-11H3/t26-,30?,31?,32-,35-,36-,37+/m0/s1
SMILES:  CC(CC(=O)OC(C(=O)OCC1=CO[C@H]([C@H]2[C@]1(O)C[C@@H]([C@]2(O)COC(=O)C(C(C)C)OC(=O)CC(C)C)OC(=O)C)OC(=O)CC(C)C)C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL556744
PubChem CID:   45271351
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002967] Hexacarboxylic acids and derivatives

*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
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[19245261]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[20151678]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[20853876]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29016 Valeriana jatamansi Species Caprifoliaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[470523]
NPT180 Cell Line HCT-8 Homo sapiens IC50 = 8200.0 nM PMID[470523]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 9900.0 nM PMID[470523]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3100.0 nM PMID[470523]

☑ 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 NPC476230 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 NPC27474
0.9892 High Similarity NPC476320
0.9892 High Similarity NPC476211
0.9789 High Similarity NPC329704
0.9787 High Similarity NPC216911
0.9583 High Similarity NPC329834
0.9579 High Similarity NPC476228
0.9355 High Similarity NPC274588
0.9263 High Similarity NPC86843
0.9255 High Similarity NPC93869
0.9255 High Similarity NPC6765
0.9158 High Similarity NPC284063
0.9158 High Similarity NPC170527
0.9109 High Similarity NPC208307
0.8737 High Similarity NPC66504
0.8737 High Similarity NPC235051
0.8252 Intermediate Similarity NPC37240
0.819 Intermediate Similarity NPC197813
0.819 Intermediate Similarity NPC80338
0.819 Intermediate Similarity NPC148270
0.8155 Intermediate Similarity NPC177013
0.8155 Intermediate Similarity NPC474730
0.8155 Intermediate Similarity NPC4899
0.8155 Intermediate Similarity NPC35185
0.8131 Intermediate Similarity NPC193741
0.8113 Intermediate Similarity NPC110701
0.8095 Intermediate Similarity NPC127235
0.8095 Intermediate Similarity NPC170432
0.8081 Intermediate Similarity NPC470187
0.8077 Intermediate Similarity NPC475928
0.8058 Intermediate Similarity NPC287539
0.8058 Intermediate Similarity NPC3488
0.8058 Intermediate Similarity NPC20673
0.8039 Intermediate Similarity NPC151093
0.7982 Intermediate Similarity NPC475851
0.7982 Intermediate Similarity NPC475924
0.798 Intermediate Similarity NPC294643
0.798 Intermediate Similarity NPC274274
0.798 Intermediate Similarity NPC473150
0.7961 Intermediate Similarity NPC244878
0.7959 Intermediate Similarity NPC93190
0.7885 Intermediate Similarity NPC98859
0.7885 Intermediate Similarity NPC219038
0.7885 Intermediate Similarity NPC4637
0.781 Intermediate Similarity NPC106668
0.781 Intermediate Similarity NPC471599
0.7778 Intermediate Similarity NPC50464
0.7736 Intermediate Similarity NPC27687
0.7736 Intermediate Similarity NPC473148
0.7692 Intermediate Similarity NPC96399
0.7692 Intermediate Similarity NPC117066
0.7692 Intermediate Similarity NPC469919
0.7692 Intermediate Similarity NPC469918
0.7642 Intermediate Similarity NPC304163
0.7596 Intermediate Similarity NPC236580
0.7596 Intermediate Similarity NPC261372
0.7596 Intermediate Similarity NPC263674
0.7596 Intermediate Similarity NPC304445
0.7596 Intermediate Similarity NPC58267
0.7547 Intermediate Similarity NPC67296
0.7524 Intermediate Similarity NPC223700
0.75 Intermediate Similarity NPC161293
0.75 Intermediate Similarity NPC474297
0.7475 Intermediate Similarity NPC149018
0.7475 Intermediate Similarity NPC171484
0.7426 Intermediate Similarity NPC22918
0.7414 Intermediate Similarity NPC219656
0.7404 Intermediate Similarity NPC291709
0.7404 Intermediate Similarity NPC241407
0.7383 Intermediate Similarity NPC471767
0.7358 Intermediate Similarity NPC90819
0.7358 Intermediate Similarity NPC124181
0.7358 Intermediate Similarity NPC249171
0.7358 Intermediate Similarity NPC49833
0.7327 Intermediate Similarity NPC148534
0.7315 Intermediate Similarity NPC250594
0.7315 Intermediate Similarity NPC200672
0.7315 Intermediate Similarity NPC78127
0.7315 Intermediate Similarity NPC471757
0.7315 Intermediate Similarity NPC214714
0.7315 Intermediate Similarity NPC80144
0.7311 Intermediate Similarity NPC219804
0.7308 Intermediate Similarity NPC63897
0.7288 Intermediate Similarity NPC233500
0.7282 Intermediate Similarity NPC276298
0.7273 Intermediate Similarity NPC259296
0.7273 Intermediate Similarity NPC98276
0.7264 Intermediate Similarity NPC153559
0.7264 Intermediate Similarity NPC470683
0.7264 Intermediate Similarity NPC470684
0.7264 Intermediate Similarity NPC472290
0.7238 Intermediate Similarity NPC167893
0.7238 Intermediate Similarity NPC472873
0.7236 Intermediate Similarity NPC213634
0.7228 Intermediate Similarity NPC258501
0.7227 Intermediate Similarity NPC196130
0.7222 Intermediate Similarity NPC26557
0.7212 Intermediate Similarity NPC472196
0.7212 Intermediate Similarity NPC320089
0.7212 Intermediate Similarity NPC472195
0.7212 Intermediate Similarity NPC238090
0.7196 Intermediate Similarity NPC37866
0.7196 Intermediate Similarity NPC473307
0.7184 Intermediate Similarity NPC246173
0.7182 Intermediate Similarity NPC86095
0.7168 Intermediate Similarity NPC106760
0.7156 Intermediate Similarity NPC475956
0.7156 Intermediate Similarity NPC49393
0.7156 Intermediate Similarity NPC252242
0.7156 Intermediate Similarity NPC94919
0.7143 Intermediate Similarity NPC472198
0.7143 Intermediate Similarity NPC159698
0.713 Intermediate Similarity NPC186861
0.713 Intermediate Similarity NPC22149
0.713 Intermediate Similarity NPC306344
0.713 Intermediate Similarity NPC473146
0.713 Intermediate Similarity NPC130792
0.713 Intermediate Similarity NPC255677
0.7129 Intermediate Similarity NPC322922
0.7129 Intermediate Similarity NPC321812
0.7119 Intermediate Similarity NPC477092
0.7117 Intermediate Similarity NPC475290
0.7117 Intermediate Similarity NPC44004
0.7117 Intermediate Similarity NPC470980
0.7115 Intermediate Similarity NPC472197
0.7115 Intermediate Similarity NPC472199
0.7103 Intermediate Similarity NPC474313
0.7103 Intermediate Similarity NPC181151
0.7103 Intermediate Similarity NPC474182
0.7103 Intermediate Similarity NPC471150
0.7091 Intermediate Similarity NPC232515
0.7091 Intermediate Similarity NPC284929
0.7091 Intermediate Similarity NPC474783
0.7091 Intermediate Similarity NPC118761
0.7091 Intermediate Similarity NPC234304
0.7091 Intermediate Similarity NPC260809
0.7091 Intermediate Similarity NPC267869
0.7091 Intermediate Similarity NPC197541
0.7069 Intermediate Similarity NPC106446
0.7064 Intermediate Similarity NPC28304
0.7064 Intermediate Similarity NPC298255
0.7059 Intermediate Similarity NPC31349
0.7054 Intermediate Similarity NPC470170
0.7054 Intermediate Similarity NPC470169
0.7048 Intermediate Similarity NPC475788
0.7048 Intermediate Similarity NPC474835
0.7043 Intermediate Similarity NPC98038
0.7043 Intermediate Similarity NPC313921
0.7037 Intermediate Similarity NPC472015
0.7037 Intermediate Similarity NPC45125
0.7037 Intermediate Similarity NPC274458
0.7037 Intermediate Similarity NPC79449
0.7037 Intermediate Similarity NPC474957
0.7034 Intermediate Similarity NPC475401
0.7034 Intermediate Similarity NPC472080
0.7027 Intermediate Similarity NPC473577
0.7027 Intermediate Similarity NPC201144
0.7027 Intermediate Similarity NPC103298
0.7027 Intermediate Similarity NPC80809
0.7027 Intermediate Similarity NPC475585
0.7027 Intermediate Similarity NPC475331
0.7027 Intermediate Similarity NPC475335
0.7027 Intermediate Similarity NPC474550
0.7027 Intermediate Similarity NPC121518
0.7027 Intermediate Similarity NPC288502
0.7027 Intermediate Similarity NPC181104
0.7019 Intermediate Similarity NPC471184
0.7019 Intermediate Similarity NPC120021
0.7019 Intermediate Similarity NPC270908
0.7019 Intermediate Similarity NPC117596
0.7019 Intermediate Similarity NPC470573
0.7019 Intermediate Similarity NPC65665
0.7019 Intermediate Similarity NPC231710
0.7019 Intermediate Similarity NPC216826
0.7018 Intermediate Similarity NPC27551
0.7018 Intermediate Similarity NPC114961
0.7009 Intermediate Similarity NPC288350
0.7009 Intermediate Similarity NPC113433
0.7009 Intermediate Similarity NPC277583
0.7009 Intermediate Similarity NPC173329
0.7009 Intermediate Similarity NPC98165
0.7009 Intermediate Similarity NPC54731
0.7 Intermediate Similarity NPC222062
0.7 Intermediate Similarity NPC133506
0.7 Intermediate Similarity NPC13171
0.7 Intermediate Similarity NPC475986
0.7 Intermediate Similarity NPC42675
0.7 Intermediate Similarity NPC40749
0.7 Intermediate Similarity NPC105725
0.7 Intermediate Similarity NPC195510
0.6992 Remote Similarity NPC152091
0.6991 Remote Similarity NPC224414
0.6991 Remote Similarity NPC473517
0.6991 Remote Similarity NPC117604
0.699 Remote Similarity NPC233997
0.6983 Remote Similarity NPC102619
0.6983 Remote Similarity NPC101400
0.6983 Remote Similarity NPC101965
0.6983 Remote Similarity NPC287075
0.6981 Remote Similarity NPC281775

  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 NPC476230 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
0.713 Intermediate Similarity NPD8133 Approved
0.7 Intermediate Similarity NPD7503 Approved
0.6957 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7899 Clinical (unspecified phase)
0.686 Remote Similarity NPD8033 Approved
0.6777 Remote Similarity NPD8377 Approved
0.6777 Remote Similarity NPD8294 Approved
0.675 Remote Similarity NPD7327 Approved
0.675 Remote Similarity NPD7328 Approved
0.6731 Remote Similarity NPD4250 Approved
0.6731 Remote Similarity NPD4251 Approved
0.6721 Remote Similarity NPD8379 Approved
0.6721 Remote Similarity NPD8378 Approved
0.6721 Remote Similarity NPD8380 Approved
0.6721 Remote Similarity NPD8296 Approved
0.6721 Remote Similarity NPD8335 Approved
0.6696 Remote Similarity NPD6686 Approved
0.6694 Remote Similarity NPD7516 Approved
0.664 Remote Similarity NPD7507 Approved
0.6635 Remote Similarity NPD4249 Approved
0.661 Remote Similarity NPD6053 Discontinued
0.6587 Remote Similarity NPD8293 Discontinued
0.6579 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6579 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6577 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6535 Remote Similarity NPD7736 Approved
0.6484 Remote Similarity NPD7319 Approved
0.6466 Remote Similarity NPD6412 Phase 2
0.6452 Remote Similarity NPD8513 Phase 3
0.64 Remote Similarity NPD6370 Approved
0.6389 Remote Similarity NPD46 Approved
0.6389 Remote Similarity NPD6698 Approved
0.6389 Remote Similarity NPD7838 Discovery
0.6381 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6373 Remote Similarity NPD4821 Approved
0.6373 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6373 Remote Similarity NPD4819 Approved
0.6373 Remote Similarity NPD4822 Approved
0.6373 Remote Similarity NPD4820 Approved
0.632 Remote Similarity NPD8515 Approved
0.632 Remote Similarity NPD8517 Approved
0.632 Remote Similarity NPD8516 Approved
0.6303 Remote Similarity NPD6371 Approved
0.6299 Remote Similarity NPD7492 Approved
0.625 Remote Similarity NPD6616 Approved
0.624 Remote Similarity NPD6054 Approved
0.624 Remote Similarity NPD6059 Approved
0.624 Remote Similarity NPD6319 Approved
0.6202 Remote Similarity NPD7078 Approved
0.6198 Remote Similarity NPD6882 Approved
0.6198 Remote Similarity NPD8297 Approved
0.619 Remote Similarity NPD8274 Clinical (unspecified phase)
0.619 Remote Similarity NPD7154 Phase 3
0.6182 Remote Similarity NPD7983 Approved
0.6176 Remote Similarity NPD4271 Approved
0.6176 Remote Similarity NPD4268 Approved
0.6142 Remote Similarity NPD8080 Discontinued
0.6129 Remote Similarity NPD6009 Approved
0.6106 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6095 Remote Similarity NPD6435 Approved
0.6087 Remote Similarity NPD7640 Approved
0.6087 Remote Similarity NPD7639 Approved
0.6063 Remote Similarity NPD6016 Approved
0.6063 Remote Similarity NPD6015 Approved
0.6053 Remote Similarity NPD6083 Phase 2
0.6053 Remote Similarity NPD6084 Phase 2
0.6038 Remote Similarity NPD5362 Discontinued
0.6034 Remote Similarity NPD5344 Discontinued
0.6018 Remote Similarity NPD5695 Phase 3
0.6016 Remote Similarity NPD5988 Approved
0.6 Remote Similarity NPD7638 Approved
0.6 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5969 Remote Similarity NPD8328 Phase 3
0.5966 Remote Similarity NPD6402 Approved
0.5966 Remote Similarity NPD7128 Approved
0.5966 Remote Similarity NPD6675 Approved
0.5966 Remote Similarity NPD5739 Approved
0.5963 Remote Similarity NPD7524 Approved
0.595 Remote Similarity NPD6373 Approved
0.595 Remote Similarity NPD6372 Approved
0.595 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5905 Remote Similarity NPD5368 Approved
0.5893 Remote Similarity NPD7637 Suspended
0.5888 Remote Similarity NPD5332 Approved
0.5888 Remote Similarity NPD6110 Phase 1
0.5888 Remote Similarity NPD5331 Approved
0.5887 Remote Similarity NPD4632 Approved
0.5882 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5868 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5868 Remote Similarity NPD7320 Approved
0.5868 Remote Similarity NPD6899 Approved
0.5868 Remote Similarity NPD6881 Approved
0.5862 Remote Similarity NPD5696 Approved
0.5856 Remote Similarity NPD1695 Approved
0.5854 Remote Similarity NPD6649 Approved
0.5854 Remote Similarity NPD8130 Phase 1
0.5854 Remote Similarity NPD6650 Approved
0.5849 Remote Similarity NPD4790 Discontinued
0.5841 Remote Similarity NPD8171 Discontinued
0.5833 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5833 Remote Similarity NPD8074 Phase 3
0.5833 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5812 Remote Similarity NPD6648 Approved
0.5797 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6033 Approved
0.5789 Remote Similarity NPD5282 Discontinued
0.5785 Remote Similarity NPD5701 Approved
0.5785 Remote Similarity NPD5697 Approved
0.5772 Remote Similarity NPD7102 Approved
0.5772 Remote Similarity NPD6883 Approved
0.5772 Remote Similarity NPD7290 Approved
0.5758 Remote Similarity NPD8451 Approved
0.5752 Remote Similarity NPD8035 Phase 2
0.5752 Remote Similarity NPD8034 Phase 2
0.5752 Remote Similarity NPD5693 Phase 1
0.5748 Remote Similarity NPD7115 Discovery
0.5741 Remote Similarity NPD3669 Approved
0.5741 Remote Similarity NPD6695 Phase 3
0.5741 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5726 Remote Similarity NPD4225 Approved
0.5726 Remote Similarity NPD6617 Approved
0.5726 Remote Similarity NPD6869 Approved
0.5726 Remote Similarity NPD6847 Approved
0.5725 Remote Similarity NPD7604 Phase 2
0.5714 Remote Similarity NPD4802 Phase 2
0.5714 Remote Similarity NPD6051 Approved
0.5714 Remote Similarity NPD7632 Discontinued
0.5714 Remote Similarity NPD8448 Approved
0.5714 Remote Similarity NPD4238 Approved
0.5704 Remote Similarity NPD5956 Approved
0.5701 Remote Similarity NPD5369 Approved
0.5692 Remote Similarity NPD5983 Phase 2
0.5692 Remote Similarity NPD8444 Approved
0.5691 Remote Similarity NPD6012 Approved
0.5691 Remote Similarity NPD6013 Approved
0.5691 Remote Similarity NPD6014 Approved
0.569 Remote Similarity NPD7839 Suspended
0.5682 Remote Similarity NPD8340 Approved
0.5682 Remote Similarity NPD8341 Approved
0.5682 Remote Similarity NPD8342 Approved
0.5682 Remote Similarity NPD8299 Approved
0.5676 Remote Similarity NPD7750 Discontinued
0.5664 Remote Similarity NPD5785 Approved
0.5656 Remote Similarity NPD6685 Approved
0.5648 Remote Similarity NPD4269 Approved
0.5648 Remote Similarity NPD4270 Approved
0.5644 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5639 Remote Similarity NPD6336 Discontinued
0.563 Remote Similarity NPD1700 Approved
0.561 Remote Similarity NPD6011 Approved
0.5606 Remote Similarity NPD7829 Approved
0.5606 Remote Similarity NPD7830 Approved
0.5606 Remote Similarity NPD6067 Discontinued
0.56 Remote Similarity NPD6401 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