Structure

Physi-Chem Properties

Molecular Weight:  366.17
Volume:  381.227
LogP:  4.399
LogD:  3.575
LogS:  -5.375
# Rotatable Bonds:  4
TPSA:  40.8
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.661
Synthetic Accessibility Score:  2.744
Fsp3:  0.318
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:  -5.34
MDCK Permeability:  3.8894791941856965e-05
Pgp-inhibitor:  0.226
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.813
30% Bioavailability (F30%):  0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.874
Plasma Protein Binding (PPB):  79.76998138427734%
Volume Distribution (VD):  1.06
Pgp-substrate:  6.087217330932617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.1
CYP1A2-substrate:  0.975
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.923
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.81
CYP2D6-inhibitor:  0.231
CYP2D6-substrate:  0.931
CYP3A4-inhibitor:  0.034
CYP3A4-substrate:  0.79

ADMET: Excretion

Clearance (CL):  8.761
Half-life (T1/2):  0.47

ADMET: Toxicity

hERG Blockers:  0.138
Human Hepatotoxicity (H-HT):  0.092
Drug-inuced Liver Injury (DILI):  0.864
AMES Toxicity:  0.253
Rat Oral Acute Toxicity:  0.221
Maximum Recommended Daily Dose:  0.38
Skin Sensitization:  0.719
Carcinogencity:  0.082
Eye Corrosion:  0.003
Eye Irritation:  0.029
Respiratory Toxicity:  0.512

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Similar NPs/Drugs  

  Natural Product: NPC31930

Natural Product ID:  NPC31930
Common Name*:   Dehydrocorydaline
IUPAC Name:   2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium
Synonyms:   Dehydrocorydaline
Standard InCHIKey:  RFKQJTRWODZPHF-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C22H24NO4/c1-13-15-6-7-18(24-2)22(27-5)17(15)12-23-9-8-14-10-19(25-3)20(26-4)11-16(14)21(13)23/h6-7,10-12H,8-9H2,1-5H3/q+1
SMILES:  COc1cc2CC[n+]3c(c2cc1OC)c(C)c1c(c3)c(OC)c(cc1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1917176
PubChem CID:   34781
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001909] Protoberberine alkaloids 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
NPO29263 Tylopilus plumbeoviolaceus Species Boletaceae Eukaryota n.a. fruit body n.a. PMID[10785434]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[18078747]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota tubers n.a. n.a. PMID[20594848]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22737858]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23194502]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. rhizome n.a. PMID[25277281]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. tuber n.a. PMID[25670016]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[32058719]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[8882438]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28926 Corydalis tuberosa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10461 Corydalis adunca Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15929 Corydalis ledebouriana Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28638 Corydalis longicalcarata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28372.1 Corydalis pallida var. tenuis Varieties Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6027.1 Corydalis ambigua var. amurensis Varieties Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15929 Corydalis ledebouriana Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28372.1 Corydalis pallida var. tenuis Varieties Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28638 Corydalis longicalcarata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10461 Corydalis adunca Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28926 Corydalis tuberosa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6027.1 Corydalis ambigua var. amurensis Varieties Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15929 Corydalis ledebouriana Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29246 Ixeris repens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15929 Corydalis ledebouriana Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29263 Tylopilus plumbeoviolaceus Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17311 Penicillium vulpinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28926 Corydalis tuberosa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29206 Lycopodium chinense Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29347 Hydnum aurantiacum Species Hydnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29441 Eremophila oppositifolia Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29490 Taxillus yadoriki Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29086 Dovyalis hebecarpa Species Salicaceae 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
NPT317 Uncleic Acid Nucleic Acid Ratio = 0.34 n.a. PMID[494693]

☑ 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 NPC31930 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
0.9834 High Similarity NPC36229
0.9834 High Similarity NPC476581
0.9834 High Similarity NPC16452
0.9558 High Similarity NPC476582
0.9558 High Similarity NPC4071
0.9558 High Similarity NPC476578
0.9468 High Similarity NPC202768
0.9468 High Similarity NPC112206
0.9468 High Similarity NPC53069
0.9468 High Similarity NPC202605
0.9468 High Similarity NPC296482
0.9263 High Similarity NPC96405
0.9263 High Similarity NPC171409
0.9227 High Similarity NPC195268
0.9227 High Similarity NPC133140
0.9202 High Similarity NPC313189
0.9026 High Similarity NPC100079
0.9026 High Similarity NPC23614
0.9 High Similarity NPC135549
0.8958 High Similarity NPC290689
0.8883 High Similarity NPC46451
0.8883 High Similarity NPC477019
0.8872 High Similarity NPC235076
0.8821 High Similarity NPC271215
0.8821 High Similarity NPC149471
0.8684 High Similarity NPC234197
0.8667 High Similarity NPC188420
0.8579 High Similarity NPC251160
0.8564 High Similarity NPC118121
0.8458 Intermediate Similarity NPC473822
0.8454 Intermediate Similarity NPC201508
0.8374 Intermediate Similarity NPC174049
0.8366 Intermediate Similarity NPC204446
0.835 Intermediate Similarity NPC236668
0.8308 Intermediate Similarity NPC146976
0.8293 Intermediate Similarity NPC122463
0.8286 Intermediate Similarity NPC255800
0.8286 Intermediate Similarity NPC96584
0.8251 Intermediate Similarity NPC312872
0.8247 Intermediate Similarity NPC287437
0.8137 Intermediate Similarity NPC473513
0.8116 Intermediate Similarity NPC210434
0.809 Intermediate Similarity NPC323345
0.809 Intermediate Similarity NPC470164
0.8079 Intermediate Similarity NPC162530
0.8057 Intermediate Similarity NPC24019
0.8053 Intermediate Similarity NPC204385
0.8037 Intermediate Similarity NPC295228
0.801 Intermediate Similarity NPC173080
0.8009 Intermediate Similarity NPC476997
0.799 Intermediate Similarity NPC266931
0.7972 Intermediate Similarity NPC476996
0.7972 Intermediate Similarity NPC476998
0.7959 Intermediate Similarity NPC224928
0.795 Intermediate Similarity NPC285558
0.7934 Intermediate Similarity NPC476999
0.7931 Intermediate Similarity NPC470020
0.7925 Intermediate Similarity NPC476994
0.7915 Intermediate Similarity NPC214980
0.786 Intermediate Similarity NPC22481
0.7857 Intermediate Similarity NPC280272
0.7846 Intermediate Similarity NPC280964
0.7846 Intermediate Similarity NPC114335
0.7846 Intermediate Similarity NPC141915
0.7843 Intermediate Similarity NPC123976
0.7843 Intermediate Similarity NPC167860
0.7842 Intermediate Similarity NPC206201
0.7838 Intermediate Similarity NPC270515
0.7824 Intermediate Similarity NPC90875
0.782 Intermediate Similarity NPC322482
0.7814 Intermediate Similarity NPC233334
0.7804 Intermediate Similarity NPC278525
0.7804 Intermediate Similarity NPC469792
0.7788 Intermediate Similarity NPC108342
0.7772 Intermediate Similarity NPC118832
0.7772 Intermediate Similarity NPC329708
0.7772 Intermediate Similarity NPC165349
0.7772 Intermediate Similarity NPC274291
0.7772 Intermediate Similarity NPC264166
0.7772 Intermediate Similarity NPC47059
0.7767 Intermediate Similarity NPC316981
0.7756 Intermediate Similarity NPC11464
0.7752 Intermediate Similarity NPC189903
0.7752 Intermediate Similarity NPC182907
0.7749 Intermediate Similarity NPC470474
0.7742 Intermediate Similarity NPC253675
0.7734 Intermediate Similarity NPC304183
0.7727 Intermediate Similarity NPC119134
0.7727 Intermediate Similarity NPC473053
0.7718 Intermediate Similarity NPC208284
0.7717 Intermediate Similarity NPC166722
0.7714 Intermediate Similarity NPC213530
0.7714 Intermediate Similarity NPC193267
0.7707 Intermediate Similarity NPC174672
0.7707 Intermediate Similarity NPC174758
0.768 Intermediate Similarity NPC476568
0.7671 Intermediate Similarity NPC476995
0.7662 Intermediate Similarity NPC11017
0.7659 Intermediate Similarity NPC82548
0.7654 Intermediate Similarity NPC106295
0.7654 Intermediate Similarity NPC476144
0.7654 Intermediate Similarity NPC51957
0.7654 Intermediate Similarity NPC16107
0.7654 Intermediate Similarity NPC210437
0.765 Intermediate Similarity NPC26850
0.7647 Intermediate Similarity NPC472111
0.7635 Intermediate Similarity NPC475774
0.7624 Intermediate Similarity NPC232727
0.7622 Intermediate Similarity NPC177404
0.7621 Intermediate Similarity NPC469589
0.7614 Intermediate Similarity NPC92111
0.7611 Intermediate Similarity NPC7467
0.7593 Intermediate Similarity NPC246381
0.7592 Intermediate Similarity NPC285941
0.7586 Intermediate Similarity NPC66815
0.7578 Intermediate Similarity NPC15406
0.7577 Intermediate Similarity NPC179704
0.7574 Intermediate Similarity NPC315957
0.7574 Intermediate Similarity NPC176538
0.7573 Intermediate Similarity NPC470931
0.7571 Intermediate Similarity NPC170114
0.7568 Intermediate Similarity NPC210296
0.7563 Intermediate Similarity NPC76748
0.7549 Intermediate Similarity NPC469440
0.7547 Intermediate Similarity NPC148409
0.7545 Intermediate Similarity NPC124313
0.7538 Intermediate Similarity NPC307963
0.7538 Intermediate Similarity NPC329541
0.7534 Intermediate Similarity NPC207283
0.7534 Intermediate Similarity NPC84164
0.7527 Intermediate Similarity NPC216816
0.7524 Intermediate Similarity NPC470549
0.7513 Intermediate Similarity NPC296527
0.7512 Intermediate Similarity NPC164374
0.7512 Intermediate Similarity NPC137929
0.7512 Intermediate Similarity NPC26679
0.75 Intermediate Similarity NPC199277
0.75 Intermediate Similarity NPC135887
0.75 Intermediate Similarity NPC200888
0.7489 Intermediate Similarity NPC217554
0.7488 Intermediate Similarity NPC274982
0.7487 Intermediate Similarity NPC284559
0.7486 Intermediate Similarity NPC26872
0.7474 Intermediate Similarity NPC190461
0.7467 Intermediate Similarity NPC284141
0.7465 Intermediate Similarity NPC17565
0.7463 Intermediate Similarity NPC251090
0.7463 Intermediate Similarity NPC13880
0.7452 Intermediate Similarity NPC185782
0.7447 Intermediate Similarity NPC471178
0.7437 Intermediate Similarity NPC469390
0.7436 Intermediate Similarity NPC132385
0.7432 Intermediate Similarity NPC473183
0.7431 Intermediate Similarity NPC314954
0.743 Intermediate Similarity NPC136860
0.743 Intermediate Similarity NPC128019
0.743 Intermediate Similarity NPC476567
0.7429 Intermediate Similarity NPC264176
0.7426 Intermediate Similarity NPC267928
0.7423 Intermediate Similarity NPC287588
0.7421 Intermediate Similarity NPC476518
0.7419 Intermediate Similarity NPC470018
0.7413 Intermediate Similarity NPC131017
0.7409 Intermediate Similarity NPC469554
0.7402 Intermediate Similarity NPC329747
0.7402 Intermediate Similarity NPC329793
0.7399 Intermediate Similarity NPC11408
0.7389 Intermediate Similarity NPC127085
0.7385 Intermediate Similarity NPC74575
0.7382 Intermediate Similarity NPC14651
0.7382 Intermediate Similarity NPC121658
0.738 Intermediate Similarity NPC183537
0.7379 Intermediate Similarity NPC162484
0.7371 Intermediate Similarity NPC472168
0.7368 Intermediate Similarity NPC201697
0.7366 Intermediate Similarity NPC184026
0.7366 Intermediate Similarity NPC39701
0.7366 Intermediate Similarity NPC127674
0.7366 Intermediate Similarity NPC5238
0.7366 Intermediate Similarity NPC469817
0.7366 Intermediate Similarity NPC295691
0.7366 Intermediate Similarity NPC278799
0.7366 Intermediate Similarity NPC207757
0.7366 Intermediate Similarity NPC276588
0.7366 Intermediate Similarity NPC54379
0.7366 Intermediate Similarity NPC138487
0.7366 Intermediate Similarity NPC193949
0.7366 Intermediate Similarity NPC216459
0.7366 Intermediate Similarity NPC204828
0.7366 Intermediate Similarity NPC41178
0.7366 Intermediate Similarity NPC249797
0.7366 Intermediate Similarity NPC110416
0.7366 Intermediate Similarity NPC2413
0.7366 Intermediate Similarity NPC189266
0.7366 Intermediate Similarity NPC172765
0.736 Intermediate Similarity NPC20249
0.7356 Intermediate Similarity NPC193777
0.7354 Intermediate Similarity NPC24954
0.7346 Intermediate Similarity NPC472098
0.7342 Intermediate Similarity NPC473184

  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 NPC31930 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
0.9468 High Similarity NPD3816 Phase 1
0.9468 High Similarity NPD3815 Phase 1
0.9227 High Similarity NPD3924 Approved
0.9227 High Similarity NPD3921 Approved
0.9227 High Similarity NPD3922 Approved
0.9227 High Similarity NPD3923 Approved
0.8883 High Similarity NPD3763 Approved
0.8619 High Similarity NPD3920 Phase 2
0.8201 Intermediate Similarity NPD6257 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD6230 Discontinued
0.8125 Intermediate Similarity NPD6569 Phase 2
0.8113 Intermediate Similarity NPD6494 Phase 2
0.81 Intermediate Similarity NPD5658 Approved
0.8032 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.803 Intermediate Similarity NPD7069 Discontinued
0.8019 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.801 Intermediate Similarity NPD5863 Clinical (unspecified phase)
0.7906 Intermediate Similarity NPD4889 Approved
0.788 Intermediate Similarity NPD7729 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD1923 Clinical (unspecified phase)
0.7772 Intermediate Similarity NPD4035 Approved
0.7772 Intermediate Similarity NPD4795 Phase 2
0.7772 Intermediate Similarity NPD4038 Approved
0.7772 Intermediate Similarity NPD4036 Approved
0.7772 Intermediate Similarity NPD31 Approved
0.7772 Intermediate Similarity NPD4037 Approved
0.7772 Intermediate Similarity NPD4033 Approved
0.7772 Intermediate Similarity NPD4034 Approved
0.7772 Intermediate Similarity NPD32 Approved
0.7772 Intermediate Similarity NPD4039 Approved
0.7772 Intermediate Similarity NPD4122 Approved
0.7766 Intermediate Similarity NPD4418 Discontinued
0.7766 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7761 Intermediate Similarity NPD6477 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD6219 Discontinued
0.7746 Intermediate Similarity NPD7674 Phase 3
0.7746 Intermediate Similarity NPD7675 Phase 3
0.7746 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD6964 Approved
0.7742 Intermediate Similarity NPD6963 Approved
0.7734 Intermediate Similarity NPD5530 Phase 1
0.7727 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD3477 Phase 2
0.7696 Intermediate Similarity NPD7222 Phase 2
0.7675 Intermediate Similarity NPD8091 Phase 3
0.7662 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD3386 Phase 2
0.7654 Intermediate Similarity NPD4584 Approved
0.7647 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7626 Intermediate Similarity NPD4551 Phase 2
0.7621 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7594 Intermediate Similarity NPD5930 Phase 3
0.7581 Intermediate Similarity NPD7426 Phase 1
0.7574 Intermediate Similarity NPD1739 Approved
0.7574 Intermediate Similarity NPD1740 Approved
0.754 Intermediate Similarity NPD2782 Approved
0.754 Intermediate Similarity NPD2780 Approved
0.7538 Intermediate Similarity NPD1038 Approved
0.7538 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD7558 Phase 2
0.7524 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7512 Intermediate Similarity NPD3397 Phase 2
0.75 Intermediate Similarity NPD4920 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6568 Discontinued
0.75 Intermediate Similarity NPD4921 Phase 3
0.75 Intermediate Similarity NPD7859 Phase 2
0.75 Intermediate Similarity NPD4919 Phase 3
0.75 Intermediate Similarity NPD4375 Approved
0.7489 Intermediate Similarity NPD4885 Approved
0.7488 Intermediate Similarity NPD5612 Discontinued
0.7487 Intermediate Similarity NPD4372 Phase 1
0.7487 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD4131 Phase 3
0.7463 Intermediate Similarity NPD2482 Clinical (unspecified phase)
0.746 Intermediate Similarity NPD2781 Approved
0.7455 Intermediate Similarity NPD4876 Phase 3
0.7455 Intermediate Similarity NPD4875 Phase 3
0.7453 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7441 Intermediate Similarity NPD5902 Approved
0.7441 Intermediate Similarity NPD5903 Approved
0.744 Intermediate Similarity NPD7453 Approved
0.744 Intermediate Similarity NPD7452 Approved
0.7438 Intermediate Similarity NPD3837 Clinical (unspecified phase)
0.7437 Intermediate Similarity NPD2334 Discontinued
0.7409 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7404 Intermediate Similarity NPD2739 Clinical (unspecified phase)
0.7393 Intermediate Similarity NPD7571 Clinical (unspecified phase)
0.7373 Intermediate Similarity NPD7719 Discontinued
0.7371 Intermediate Similarity NPD7169 Suspended
0.7368 Intermediate Similarity NPD4437 Phase 3
0.7361 Intermediate Similarity NPD1954 Phase 1
0.7353 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD8052 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5601 Phase 2
0.7306 Intermediate Similarity NPD6553 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD6500 Approved
0.7302 Intermediate Similarity NPD6501 Approved
0.7299 Intermediate Similarity NPD4502 Phase 2
0.7296 Intermediate Similarity NPD4203 Approved
0.7296 Intermediate Similarity NPD4204 Approved
0.7292 Intermediate Similarity NPD1078 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD1034 Phase 3
0.7286 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD4996 Approved
0.7285 Intermediate Similarity NPD4995 Approved
0.7281 Intermediate Similarity NPD1856 Discontinued
0.7273 Intermediate Similarity NPD1392 Approved
0.7273 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7555 Discontinued
0.7269 Intermediate Similarity NPD7620 Phase 2
0.7268 Intermediate Similarity NPD3825 Phase 3
0.7257 Intermediate Similarity NPD6790 Phase 1
0.7241 Intermediate Similarity NPD3396 Approved
0.7241 Intermediate Similarity NPD3395 Approved
0.724 Intermediate Similarity NPD4724 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD4925 Approved
0.7238 Intermediate Similarity NPD5528 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD5529 Phase 1
0.7236 Intermediate Similarity NPD2917 Approved
0.7235 Intermediate Similarity NPD5147 Discontinued
0.7231 Intermediate Similarity NPD1032 Phase 2
0.723 Intermediate Similarity NPD5944 Phase 1
0.723 Intermediate Similarity NPD5945 Phase 1
0.7225 Intermediate Similarity NPD3003 Approved
0.7225 Intermediate Similarity NPD2060 Approved
0.7222 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD5067 Phase 2
0.7217 Intermediate Similarity NPD5066 Phase 2
0.7194 Intermediate Similarity NPD1620 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD6361 Phase 2
0.7189 Intermediate Similarity NPD6242 Discontinued
0.7186 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD3541 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD3354 Phase 2
0.7172 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD2952 Discontinued
0.7162 Intermediate Similarity NPD7567 Approved
0.7162 Intermediate Similarity NPD1900 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD2600 Approved
0.7157 Intermediate Similarity NPD2599 Approved
0.7157 Intermediate Similarity NPD2601 Approved
0.7156 Intermediate Similarity NPD7672 Approved
0.7156 Intermediate Similarity NPD7671 Approved
0.7143 Intermediate Similarity NPD5007 Approved
0.7143 Intermediate Similarity NPD4071 Approved
0.7143 Intermediate Similarity NPD4072 Approved
0.7137 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.7137 Intermediate Similarity NPD5905 Phase 1
0.713 Intermediate Similarity NPD8100 Phase 3
0.7129 Intermediate Similarity NPD6991 Approved
0.7129 Intermediate Similarity NPD6281 Approved
0.7129 Intermediate Similarity NPD8063 Discontinued
0.7119 Intermediate Similarity NPD7956 Approved
0.7119 Intermediate Similarity NPD7955 Approved
0.7108 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD802 Phase 2
0.7105 Intermediate Similarity NPD112 Approved
0.7105 Intermediate Similarity NPD9705 Discontinued
0.7097 Intermediate Similarity NPD4429 Discontinued
0.7095 Intermediate Similarity NPD3946 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD2582 Approved
0.709 Intermediate Similarity NPD2581 Approved
0.7087 Intermediate Similarity NPD6769 Clinical (unspecified phase)
0.7082 Intermediate Similarity NPD5008 Approved
0.7081 Intermediate Similarity NPD6975 Discontinued
0.7079 Intermediate Similarity NPD4021 Phase 2
0.7075 Intermediate Similarity NPD2187 Approved
0.7075 Intermediate Similarity NPD2189 Approved
0.7074 Intermediate Similarity NPD5051 Phase 1
0.7073 Intermediate Similarity NPD1602 Discontinued
0.7073 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD6590 Discontinued
0.7067 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD5256 Discontinued
0.7064 Intermediate Similarity NPD7194 Discontinued
0.7061 Intermediate Similarity NPD7885 Phase 2
0.7061 Intermediate Similarity NPD7886 Phase 2
0.7048 Intermediate Similarity NPD4044 Discontinued
0.7047 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD5559 Phase 2
0.7039 Intermediate Similarity NPD6244 Phase 3
0.7039 Intermediate Similarity NPD6243 Phase 3
0.7039 Intermediate Similarity NPD6550 Discontinued
0.7039 Intermediate Similarity NPD8101 Phase 3
0.7035 Intermediate Similarity NPD2757 Phase 2
0.7032 Intermediate Similarity NPD8479 Phase 2
0.7028 Intermediate Similarity NPD5429 Discontinued
0.7026 Intermediate Similarity NPD4083 Discontinued
0.7021 Intermediate Similarity NPD5539 Phase 2
0.7019 Intermediate Similarity NPD4548 Discontinued
0.7019 Intermediate Similarity NPD5999 Phase 2
0.7009 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6262 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD5100 Phase 3
0.7005 Intermediate Similarity NPD7034 Discontinued
0.7005 Intermediate Similarity NPD8251 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