Structure

Physi-Chem Properties

Molecular Weight:  337.13
Volume:  339.396
LogP:  4.984
LogD:  3.51
LogS:  -6.812
# Rotatable Bonds:  2
TPSA:  40.16
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.667
Synthetic Accessibility Score:  2.704
Fsp3:  0.3
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.076
MDCK Permeability:  4.143876867601648e-05
Pgp-inhibitor:  0.795
Pgp-substrate:  0.952
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.266
Plasma Protein Binding (PPB):  84.8412094116211%
Volume Distribution (VD):  0.922
Pgp-substrate:  4.609837055206299%

ADMET: Metabolism

CYP1A2-inhibitor:  0.954
CYP1A2-substrate:  0.902
CYP2C19-inhibitor:  0.95
CYP2C19-substrate:  0.814
CYP2C9-inhibitor:  0.358
CYP2C9-substrate:  0.927
CYP2D6-inhibitor:  0.931
CYP2D6-substrate:  0.938
CYP3A4-inhibitor:  0.719
CYP3A4-substrate:  0.294

ADMET: Excretion

Clearance (CL):  11.718
Half-life (T1/2):  0.256

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.259
Drug-inuced Liver Injury (DILI):  0.916
AMES Toxicity:  0.748
Rat Oral Acute Toxicity:  0.071
Maximum Recommended Daily Dose:  0.897
Skin Sensitization:  0.942
Carcinogencity:  0.909
Eye Corrosion:  0.011
Eye Irritation:  0.237
Respiratory Toxicity:  0.937

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

  Natural Product: NPC312531

Natural Product ID:  NPC312531
Common Name*:   Dehydrodicentrine
IUPAC Name:   n.a.
Synonyms:   Dehydrodicentrine
Standard InCHIKey:  HIZKFQOZVOUKDP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H19NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h6-9H,4-5,10H2,1-3H3
SMILES:  COc1cc2c(cc1OC)cc1c3c2c2OCOc2cc3CCN1C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL456942
PubChem CID:   3084326
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

*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
NPO24769 Baptisia australis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24769 Baptisia australis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23531 Valeriana ficariifolia Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24002 Nassauvia uniflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24803 Hymenothrix wislizeni Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24769 Baptisia australis Species Fabaceae 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
NPT177 Tissue Aorta Rattus norvegicus Activity = 95.5 % PMID[538853]
NPT177 Tissue Aorta Rattus norvegicus Activity = 108.0 % PMID[538853]

☑ 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 NPC312531 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
0.9645 High Similarity NPC249405
0.9583 High Similarity NPC190461
0.9471 High Similarity NPC179704
0.9408 High Similarity NPC287588
0.931 High Similarity NPC474904
0.929 High Similarity NPC285941
0.9143 High Similarity NPC320088
0.9045 High Similarity NPC302001
0.8967 High Similarity NPC244606
0.8967 High Similarity NPC156728
0.8935 High Similarity NPC16805
0.8935 High Similarity NPC302527
0.8935 High Similarity NPC167546
0.892 High Similarity NPC33902
0.892 High Similarity NPC276674
0.8901 High Similarity NPC212163
0.8882 High Similarity NPC476432
0.8882 High Similarity NPC24264
0.8846 High Similarity NPC23080
0.8846 High Similarity NPC193906
0.884 High Similarity NPC162653
0.8833 High Similarity NPC78284
0.883 High Similarity NPC210918
0.883 High Similarity NPC247389
0.8824 High Similarity NPC225774
0.8817 High Similarity NPC24954
0.8804 High Similarity NPC295676
0.8772 High Similarity NPC219341
0.8678 High Similarity NPC19520
0.8678 High Similarity NPC149090
0.8647 High Similarity NPC266753
0.8647 High Similarity NPC306902
0.8647 High Similarity NPC232924
0.8647 High Similarity NPC477559
0.8647 High Similarity NPC160298
0.8621 High Similarity NPC6152
0.858 High Similarity NPC199465
0.858 High Similarity NPC128560
0.858 High Similarity NPC229166
0.8521 High Similarity NPC325871
0.8521 High Similarity NPC99659
0.8483 Intermediate Similarity NPC114364
0.8483 Intermediate Similarity NPC320223
0.8421 Intermediate Similarity NPC476572
0.84 Intermediate Similarity NPC298979
0.8361 Intermediate Similarity NPC296742
0.8359 Intermediate Similarity NPC55470
0.8352 Intermediate Similarity NPC241055
0.8343 Intermediate Similarity NPC248642
0.8343 Intermediate Similarity NPC116284
0.8343 Intermediate Similarity NPC304659
0.8343 Intermediate Similarity NPC86144
0.8333 Intermediate Similarity NPC258695
0.8333 Intermediate Similarity NPC470879
0.8333 Intermediate Similarity NPC126284
0.8306 Intermediate Similarity NPC224293
0.8304 Intermediate Similarity NPC244112
0.8297 Intermediate Similarity NPC156576
0.8287 Intermediate Similarity NPC476574
0.8287 Intermediate Similarity NPC155442
0.8287 Intermediate Similarity NPC474506
0.8287 Intermediate Similarity NPC477561
0.8287 Intermediate Similarity NPC32413
0.8287 Intermediate Similarity NPC312918
0.8286 Intermediate Similarity NPC168409
0.8278 Intermediate Similarity NPC23219
0.8261 Intermediate Similarity NPC112676
0.8251 Intermediate Similarity NPC69213
0.8235 Intermediate Similarity NPC326316
0.8235 Intermediate Similarity NPC81733
0.8232 Intermediate Similarity NPC267408
0.8229 Intermediate Similarity NPC189470
0.8225 Intermediate Similarity NPC211296
0.8222 Intermediate Similarity NPC112575
0.8198 Intermediate Similarity NPC93593
0.8197 Intermediate Similarity NPC135772
0.8182 Intermediate Similarity NPC78222
0.8182 Intermediate Similarity NPC196447
0.8182 Intermediate Similarity NPC253043
0.8182 Intermediate Similarity NPC212794
0.8182 Intermediate Similarity NPC306843
0.8182 Intermediate Similarity NPC13504
0.8182 Intermediate Similarity NPC29472
0.8182 Intermediate Similarity NPC136508
0.8182 Intermediate Similarity NPC477563
0.8182 Intermediate Similarity NPC96603
0.8177 Intermediate Similarity NPC118633
0.8177 Intermediate Similarity NPC294790
0.8177 Intermediate Similarity NPC148693
0.8167 Intermediate Similarity NPC477558
0.8162 Intermediate Similarity NPC237579
0.8148 Intermediate Similarity NPC17677
0.8125 Intermediate Similarity NPC324144
0.8118 Intermediate Similarity NPC82763
0.8108 Intermediate Similarity NPC57036
0.8108 Intermediate Similarity NPC214116
0.8092 Intermediate Similarity NPC138487
0.8092 Intermediate Similarity NPC76079
0.8092 Intermediate Similarity NPC41178
0.8092 Intermediate Similarity NPC216459
0.809 Intermediate Similarity NPC158376
0.809 Intermediate Similarity NPC12053
0.809 Intermediate Similarity NPC205421
0.809 Intermediate Similarity NPC81218
0.809 Intermediate Similarity NPC474931
0.809 Intermediate Similarity NPC306555
0.809 Intermediate Similarity NPC117188
0.809 Intermediate Similarity NPC145832
0.8077 Intermediate Similarity NPC260118
0.8065 Intermediate Similarity NPC476576
0.8065 Intermediate Similarity NPC186546
0.8059 Intermediate Similarity NPC130941
0.8059 Intermediate Similarity NPC475959
0.8057 Intermediate Similarity NPC477080
0.805 Intermediate Similarity NPC100079
0.805 Intermediate Similarity NPC23614
0.8046 Intermediate Similarity NPC146288
0.8041 Intermediate Similarity NPC261388
0.8033 Intermediate Similarity NPC192939
0.8033 Intermediate Similarity NPC215747
0.8031 Intermediate Similarity NPC159101
0.803 Intermediate Similarity NPC149471
0.803 Intermediate Similarity NPC271215
0.8022 Intermediate Similarity NPC265383
0.8012 Intermediate Similarity NPC219162
0.8011 Intermediate Similarity NPC477186
0.801 Intermediate Similarity NPC5374
0.8 Intermediate Similarity NPC152212
0.8 Intermediate Similarity NPC308943
0.799 Intermediate Similarity NPC235076
0.7989 Intermediate Similarity NPC204947
0.7988 Intermediate Similarity NPC145304
0.798 Intermediate Similarity NPC251160
0.7977 Intermediate Similarity NPC233029
0.7977 Intermediate Similarity NPC210148
0.797 Intermediate Similarity NPC188420
0.7966 Intermediate Similarity NPC60186
0.7956 Intermediate Similarity NPC239775
0.7946 Intermediate Similarity NPC28425
0.7946 Intermediate Similarity NPC476575
0.7943 Intermediate Similarity NPC126519
0.7943 Intermediate Similarity NPC203784
0.7943 Intermediate Similarity NPC31311
0.7943 Intermediate Similarity NPC170503
0.7943 Intermediate Similarity NPC234392
0.7927 Intermediate Similarity NPC471489
0.7921 Intermediate Similarity NPC46451
0.7921 Intermediate Similarity NPC1229
0.791 Intermediate Similarity NPC166014
0.791 Intermediate Similarity NPC27410
0.7901 Intermediate Similarity NPC26240
0.7901 Intermediate Similarity NPC477562
0.7901 Intermediate Similarity NPC69712
0.7895 Intermediate Similarity NPC253883
0.7895 Intermediate Similarity NPC90844
0.7895 Intermediate Similarity NPC95075
0.7892 Intermediate Similarity NPC119579
0.7889 Intermediate Similarity NPC150879
0.7884 Intermediate Similarity NPC79213
0.7865 Intermediate Similarity NPC71124
0.7861 Intermediate Similarity NPC219170
0.7861 Intermediate Similarity NPC180253
0.7849 Intermediate Similarity NPC275132
0.7849 Intermediate Similarity NPC276060
0.7842 Intermediate Similarity NPC117717
0.7838 Intermediate Similarity NPC311936
0.7838 Intermediate Similarity NPC220961
0.7814 Intermediate Similarity NPC192135
0.7814 Intermediate Similarity NPC66341
0.7814 Intermediate Similarity NPC2314
0.7814 Intermediate Similarity NPC477020
0.7803 Intermediate Similarity NPC92541
0.7802 Intermediate Similarity NPC168753
0.7802 Intermediate Similarity NPC118274
0.7789 Intermediate Similarity NPC475754
0.7778 Intermediate Similarity NPC276944
0.7778 Intermediate Similarity NPC207873
0.7778 Intermediate Similarity NPC232514
0.7778 Intermediate Similarity NPC100573
0.7778 Intermediate Similarity NPC238530
0.7755 Intermediate Similarity NPC207971
0.7754 Intermediate Similarity NPC73492
0.7754 Intermediate Similarity NPC299990
0.7753 Intermediate Similarity NPC111485
0.7749 Intermediate Similarity NPC254957
0.774 Intermediate Similarity NPC186063
0.7727 Intermediate Similarity NPC222561
0.7725 Intermediate Similarity NPC22928
0.7722 Intermediate Similarity NPC233650
0.7718 Intermediate Similarity NPC118121
0.7716 Intermediate Similarity NPC38961
0.7716 Intermediate Similarity NPC268077
0.7713 Intermediate Similarity NPC302275
0.7696 Intermediate Similarity NPC204446
0.7692 Intermediate Similarity NPC474324
0.7692 Intermediate Similarity NPC57812
0.7692 Intermediate Similarity NPC471604
0.7688 Intermediate Similarity NPC51957
0.7688 Intermediate Similarity NPC476144
0.7688 Intermediate Similarity NPC144863

  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 NPC312531 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 NPD3763 Approved
0.7868 Intermediate Similarity NPD4859 Phase 1
0.7688 Intermediate Similarity NPD4584 Approved
0.7656 Intermediate Similarity NPD7262 Phase 1
0.7647 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD3815 Phase 1
0.7624 Intermediate Similarity NPD3816 Phase 1
0.7606 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7577 Intermediate Similarity NPD5582 Discontinued
0.7554 Intermediate Similarity NPD4481 Phase 3
0.7541 Intermediate Similarity NPD3051 Approved
0.7514 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7479 Phase 2
0.7432 Intermediate Similarity NPD6037 Discontinued
0.7414 Intermediate Similarity NPD3301 Approved
0.7405 Intermediate Similarity NPD2970 Approved
0.7405 Intermediate Similarity NPD2969 Approved
0.738 Intermediate Similarity NPD8099 Discontinued
0.738 Intermediate Similarity NPD8252 Approved
0.738 Intermediate Similarity NPD8251 Approved
0.7371 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD8156 Discontinued
0.7303 Intermediate Similarity NPD6030 Approved
0.7303 Intermediate Similarity NPD6031 Approved
0.7302 Intermediate Similarity NPD3920 Phase 2
0.7273 Intermediate Similarity NPD27 Approved
0.7273 Intermediate Similarity NPD2489 Approved
0.7273 Intermediate Similarity NPD7238 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD6788 Approved
0.7268 Intermediate Similarity NPD3349 Phase 2
0.7263 Intermediate Similarity NPD6496 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD6493 Phase 3
0.7249 Intermediate Similarity NPD5810 Discontinued
0.7245 Intermediate Similarity NPD3921 Approved
0.7245 Intermediate Similarity NPD3924 Approved
0.7245 Intermediate Similarity NPD3922 Approved
0.7245 Intermediate Similarity NPD3923 Approved
0.7243 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD6723 Discontinued
0.7234 Intermediate Similarity NPD5938 Phase 3
0.7232 Intermediate Similarity NPD2420 Approved
0.7232 Intermediate Similarity NPD2421 Approved
0.7211 Intermediate Similarity NPD5900 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD7298 Approved
0.7194 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD6607 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7906 Approved
0.7178 Intermediate Similarity NPD3515 Approved
0.7178 Intermediate Similarity NPD3516 Approved
0.7164 Intermediate Similarity NPD6612 Phase 2
0.7158 Intermediate Similarity NPD5521 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD5600 Discontinued
0.715 Intermediate Similarity NPD2971 Approved
0.715 Intermediate Similarity NPD2968 Approved
0.7143 Intermediate Similarity NPD3408 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5966 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4083 Discontinued
0.7127 Intermediate Similarity NPD6357 Discontinued
0.7127 Intermediate Similarity NPD4017 Approved
0.712 Intermediate Similarity NPD2358 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD8053 Approved
0.7113 Intermediate Similarity NPD8054 Approved
0.7112 Intermediate Similarity NPD3984 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD3983 Phase 3
0.71 Intermediate Similarity NPD7034 Discontinued
0.709 Intermediate Similarity NPD6365 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD4420 Approved
0.7065 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7310 Approved
0.7062 Intermediate Similarity NPD7312 Approved
0.7062 Intermediate Similarity NPD7313 Approved
0.7062 Intermediate Similarity NPD7311 Approved
0.7062 Intermediate Similarity NPD4577 Approved
0.7062 Intermediate Similarity NPD4578 Approved
0.7056 Intermediate Similarity NPD5896 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD7858 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD4663 Approved
0.7026 Intermediate Similarity NPD7309 Approved
0.7021 Intermediate Similarity NPD4986 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD3640 Phase 3
0.7017 Intermediate Similarity NPD3639 Approved
0.7017 Intermediate Similarity NPD3641 Approved
0.7016 Intermediate Similarity NPD4498 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD6621 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD8149 Discontinued
0.7005 Intermediate Similarity NPD5658 Approved
0.7005 Intermediate Similarity NPD3398 Discontinued
0.7 Intermediate Similarity NPD7922 Phase 1
0.6995 Remote Similarity NPD6996 Clinical (unspecified phase)
0.699 Remote Similarity NPD5530 Phase 1
0.6984 Remote Similarity NPD6071 Discontinued
0.698 Remote Similarity NPD5071 Phase 2
0.6971 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6971 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6952 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6952 Remote Similarity NPD7833 Phase 2
0.6952 Remote Similarity NPD7831 Phase 2
0.6952 Remote Similarity NPD7225 Discontinued
0.695 Remote Similarity NPD6526 Approved
0.694 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6936 Remote Similarity NPD3109 Approved
0.6936 Remote Similarity NPD3110 Approved
0.6935 Remote Similarity NPD2560 Approved
0.6935 Remote Similarity NPD2563 Approved
0.6931 Remote Similarity NPD7802 Discontinued
0.6927 Remote Similarity NPD5005 Approved
0.6927 Remote Similarity NPD5006 Approved
0.6927 Remote Similarity NPD5241 Discontinued
0.6923 Remote Similarity NPD6625 Approved
0.6923 Remote Similarity NPD4727 Phase 1
0.6915 Remote Similarity NPD4796 Discontinued
0.6911 Remote Similarity NPD2898 Approved
0.6898 Remote Similarity NPD1743 Approved
0.6898 Remote Similarity NPD1742 Approved
0.6898 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6898 Remote Similarity NPD19 Approved
0.6897 Remote Similarity NPD6877 Discontinued
0.6881 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6881 Remote Similarity NPD7224 Discontinued
0.6881 Remote Similarity NPD7223 Discontinued
0.6878 Remote Similarity NPD4885 Approved
0.6872 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6866 Remote Similarity NPD7278 Phase 2
0.6866 Remote Similarity NPD7279 Phase 2
0.6866 Remote Similarity NPD6046 Clinical (unspecified phase)
0.6865 Remote Similarity NPD4773 Phase 2
0.6865 Remote Similarity NPD4772 Phase 2
0.6862 Remote Similarity NPD6533 Clinical (unspecified phase)
0.686 Remote Similarity NPD2669 Clinical (unspecified phase)
0.6857 Remote Similarity NPD4997 Clinical (unspecified phase)
0.685 Remote Similarity NPD2490 Approved
0.685 Remote Similarity NPD5641 Discontinued
0.685 Remote Similarity NPD2488 Approved
0.6847 Remote Similarity NPD2974 Approved
0.6847 Remote Similarity NPD2973 Approved
0.6847 Remote Similarity NPD6494 Phase 2
0.6847 Remote Similarity NPD2975 Approved
0.6847 Remote Similarity NPD6527 Approved
0.684 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6837 Remote Similarity NPD8453 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7255 Clinical (unspecified phase)
0.6825 Remote Similarity NPD7400 Phase 3
0.6821 Remote Similarity NPD5718 Phase 2
0.6806 Remote Similarity NPD4010 Discontinued
0.6806 Remote Similarity NPD5930 Phase 3
0.68 Remote Similarity NPD2845 Phase 2
0.68 Remote Similarity NPD2843 Phase 2
0.6797 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6793 Remote Similarity NPD2883 Discontinued
0.6778 Remote Similarity NPD5754 Discontinued
0.6772 Remote Similarity NPD5604 Discontinued
0.6771 Remote Similarity NPD5680 Clinical (unspecified phase)
0.6771 Remote Similarity NPD3975 Discontinued
0.6765 Remote Similarity NPD6284 Clinical (unspecified phase)
0.6754 Remote Similarity NPD6457 Approved
0.6754 Remote Similarity NPD6107 Approved
0.6749 Remote Similarity NPD4418 Discontinued
0.6748 Remote Similarity NPD4580 Approved
0.674 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6739 Remote Similarity NPD5976 Discontinued
0.6734 Remote Similarity NPD5087 Clinical (unspecified phase)
0.6728 Remote Similarity NPD5070 Clinical (unspecified phase)
0.6721 Remote Similarity NPD1424 Approved
0.6719 Remote Similarity NPD4166 Phase 2
0.6715 Remote Similarity NPD3452 Approved
0.6715 Remote Similarity NPD2494 Approved
0.6715 Remote Similarity NPD3450 Approved
0.6715 Remote Similarity NPD2493 Approved
0.6714 Remote Similarity NPD7222 Phase 2
0.6703 Remote Similarity NPD3845 Phase 1
0.6703 Remote Similarity NPD814 Clinical (unspecified phase)
0.6702 Remote Similarity NPD6737 Phase 2
0.6702 Remote Similarity NPD6738 Phase 2
0.6702 Remote Similarity NPD2977 Approved
0.6702 Remote Similarity NPD2978 Approved
0.67 Remote Similarity NPD7125 Discontinued
0.6699 Remote Similarity NPD8095 Phase 1
0.6686 Remote Similarity NPD4474 Approved
0.6686 Remote Similarity NPD4475 Approved
0.6686 Remote Similarity NPD554 Clinical (unspecified phase)
0.6684 Remote Similarity NPD4055 Discovery
0.6683 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6683 Remote Similarity NPD6021 Clinical (unspecified phase)
0.6683 Remote Similarity NPD956 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4107 Approved
0.6667 Remote Similarity NPD4597 Approved
0.6667 Remote Similarity NPD4598 Approved
0.6667 Remote Similarity NPD6063 Approved
0.665 Remote Similarity NPD6340 Approved
0.665 Remote Similarity NPD6339 Approved
0.665 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6635 Remote Similarity NPD7263 Phase 2
0.6634 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6633 Remote Similarity NPD7281 Phase 3
0.6633 Remote Similarity NPD7280 Phase 3
0.6633 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6632 Remote Similarity NPD5186 Approved
0.6632 Remote Similarity NPD5183 Approved
0.6632 Remote Similarity NPD5847 Phase 1

  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