Structure

Physi-Chem Properties

Molecular Weight:  697.16
Volume:  686.904
LogP:  6.132
LogD:  2.438
LogS:  -4.999
# Rotatable Bonds:  5
TPSA:  221.14
# H-Bond Aceptor:  12
# H-Bond Donor:  9
# Rings:  8
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.054
Synthetic Accessibility Score:  3.716
Fsp3:  0.05
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  3

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.486
MDCK Permeability:  5.936832621955546e-06
Pgp-inhibitor:  0.092
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  1.0
20% Bioavailability (F20%):  0.994
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  94.87886047363281%
Volume Distribution (VD):  -0.005
Pgp-substrate:  11.118158340454102%

ADMET: Metabolism

CYP1A2-inhibitor:  0.934
CYP1A2-substrate:  0.066
CYP2C19-inhibitor:  0.463
CYP2C19-substrate:  0.029
CYP2C9-inhibitor:  0.654
CYP2C9-substrate:  0.552
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.235
CYP3A4-inhibitor:  0.047
CYP3A4-substrate:  0.026

ADMET: Excretion

Clearance (CL):  10.758
Half-life (T1/2):  0.74

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.051
Drug-inuced Liver Injury (DILI):  0.99
AMES Toxicity:  0.319
Rat Oral Acute Toxicity:  0.056
Maximum Recommended Daily Dose:  0.985
Skin Sensitization:  0.985
Carcinogencity:  0.814
Eye Corrosion:  0.003
Eye Irritation:  0.941
Respiratory Toxicity:  0.014

Download Data

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

  Natural Product: NPC124086

Natural Product ID:  NPC124086
Common Name*:   Purpurone
IUPAC Name:   n.a.
Synonyms:   Purpurone
Standard InCHIKey:  USHRRYVVGLGHAL-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C40H27NO11/c42-20-5-1-17(2-6-20)9-10-41-37-33(18-3-7-25(43)27(45)11-18)39(51)23-15-31(49)29(47)13-21(23)35(37)36-22-14-30(48)32(50)16-24(22)40(52)34(38(36)41)19-4-8-26(44)28(46)12-19/h1-8,11-16,42-50H,9-10H2
SMILES:  Oc1ccc(cc1)CCn1c2=C(c3ccc(c(c3)O)O)C(=O)c3c(c2c2c1=C(c1ccc(c(c1)O)O)C(=O)c1c2cc(c(c1)O)O)cc(c(c3)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1214277
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0002044] Phenylnaphthalenes

*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
NPO20091 Iotrochota baculifera Species Iotrochotidae Eukaryota Chinese n.a. n.a. PMID[20624681]
NPO20091 Iotrochota baculifera Species Iotrochotidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20091 Iotrochota baculifera Species Iotrochotidae 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
NPT477 Individual Protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens RU = -26.3 pg/mm2 PMID[566407]
NPT20 Organism Candida albicans Candida albicans MIC = 12.5 ug.mL-1 PMID[566407]
NPT20 Organism Candida albicans Candida albicans MIC = 25.0 ug.mL-1 PMID[566407]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 > 25.0 ug.mL-1 PMID[566407]
NPT2 Others Unspecified RU = -25.7 pg/mm2 PMID[566407]
NPT2 Others Unspecified RU = -23.0 pg/mm2 PMID[566407]
NPT945 Individual Protein ATP-citrate synthase Rattus norvegicus IC50 = 7000.0 nM PMID[566408]
NPT946 Individual Protein ATP-citrate synthase Homo sapiens IC50 = 7000.0 nM PMID[566409]

☑ 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 NPC124086 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
0.9789 High Similarity NPC239763
0.9789 High Similarity NPC190401
0.9688 High Similarity NPC268393
0.9688 High Similarity NPC13599
0.9688 High Similarity NPC3214
0.9688 High Similarity NPC191088
0.9688 High Similarity NPC298840
0.9688 High Similarity NPC303384
0.9585 High Similarity NPC246658
0.9391 High Similarity NPC121069
0.7917 Intermediate Similarity NPC256935
0.7653 Intermediate Similarity NPC271792
0.7437 Intermediate Similarity NPC73555
0.7407 Intermediate Similarity NPC146976
0.7391 Intermediate Similarity NPC15406
0.7384 Intermediate Similarity NPC129897
0.738 Intermediate Similarity NPC210296
0.7379 Intermediate Similarity NPC146724
0.7361 Intermediate Similarity NPC236668
0.7356 Intermediate Similarity NPC472284
0.7289 Intermediate Similarity NPC24019
0.7282 Intermediate Similarity NPC471448
0.7277 Intermediate Similarity NPC77878
0.7277 Intermediate Similarity NPC302807
0.7269 Intermediate Similarity NPC22481
0.7256 Intermediate Similarity NPC61038
0.7252 Intermediate Similarity NPC210434
0.724 Intermediate Similarity NPC276657
0.7225 Intermediate Similarity NPC473814
0.7225 Intermediate Similarity NPC78767
0.7222 Intermediate Similarity NPC470020
0.7212 Intermediate Similarity NPC93390
0.7212 Intermediate Similarity NPC278525
0.7203 Intermediate Similarity NPC183537
0.7198 Intermediate Similarity NPC56170
0.7196 Intermediate Similarity NPC175602
0.7174 Intermediate Similarity NPC189903
0.7174 Intermediate Similarity NPC182907
0.7171 Intermediate Similarity NPC206186
0.7168 Intermediate Similarity NPC246381
0.7162 Intermediate Similarity NPC253675
0.7157 Intermediate Similarity NPC241025
0.7137 Intermediate Similarity NPC208522
0.7131 Intermediate Similarity NPC181081
0.713 Intermediate Similarity NPC108342
0.7123 Intermediate Similarity NPC207866
0.7119 Intermediate Similarity NPC132385
0.7118 Intermediate Similarity NPC329631
0.7116 Intermediate Similarity NPC472287
0.7116 Intermediate Similarity NPC472286
0.7087 Intermediate Similarity NPC208898
0.7087 Intermediate Similarity NPC90875
0.7085 Intermediate Similarity NPC14686
0.7083 Intermediate Similarity NPC53344
0.7078 Intermediate Similarity NPC110182
0.7067 Intermediate Similarity NPC94842
0.7064 Intermediate Similarity NPC160898
0.7062 Intermediate Similarity NPC74153
0.7045 Intermediate Similarity NPC232225
0.704 Intermediate Similarity NPC269270
0.7032 Intermediate Similarity NPC220337
0.7032 Intermediate Similarity NPC9894
0.7027 Intermediate Similarity NPC293151
0.7027 Intermediate Similarity NPC27041
0.7012 Intermediate Similarity NPC318068
0.7 Intermediate Similarity NPC473821
0.7 Intermediate Similarity NPC233334
0.6996 Remote Similarity NPC166722
0.6996 Remote Similarity NPC204446
0.6995 Remote Similarity NPC164340
0.6992 Remote Similarity NPC124313
0.699 Remote Similarity NPC295158
0.6987 Remote Similarity NPC476998
0.6987 Remote Similarity NPC476996
0.6979 Remote Similarity NPC84164
0.6979 Remote Similarity NPC207283
0.6978 Remote Similarity NPC253314
0.6972 Remote Similarity NPC207873
0.6972 Remote Similarity NPC100573
0.6957 Remote Similarity NPC316065
0.6957 Remote Similarity NPC289905
0.6953 Remote Similarity NPC476995
0.6946 Remote Similarity NPC51854
0.6943 Remote Similarity NPC476997
0.6943 Remote Similarity NPC476994
0.6937 Remote Similarity NPC237740
0.6933 Remote Similarity NPC469439
0.693 Remote Similarity NPC214980
0.6929 Remote Similarity NPC472588
0.6923 Remote Similarity NPC202605
0.6923 Remote Similarity NPC219087
0.6923 Remote Similarity NPC112206
0.6916 Remote Similarity NPC51388
0.6906 Remote Similarity NPC322064
0.6904 Remote Similarity NPC270515
0.6904 Remote Similarity NPC9729
0.6895 Remote Similarity NPC171787
0.6894 Remote Similarity NPC41501
0.689 Remote Similarity NPC183805
0.6883 Remote Similarity NPC316841
0.6883 Remote Similarity NPC475303
0.6883 Remote Similarity NPC475596
0.6883 Remote Similarity NPC474701
0.6878 Remote Similarity NPC23294
0.6878 Remote Similarity NPC475648
0.6877 Remote Similarity NPC279589
0.6872 Remote Similarity NPC220851
0.6872 Remote Similarity NPC118121
0.6872 Remote Similarity NPC127026
0.6872 Remote Similarity NPC472589
0.6872 Remote Similarity NPC127720
0.6869 Remote Similarity NPC17677
0.6869 Remote Similarity NPC102008
0.6864 Remote Similarity NPC325297
0.6858 Remote Similarity NPC54066
0.6857 Remote Similarity NPC191489
0.6857 Remote Similarity NPC89549
0.6856 Remote Similarity NPC470018
0.6853 Remote Similarity NPC30456
0.6853 Remote Similarity NPC207686
0.685 Remote Similarity NPC45048
0.6849 Remote Similarity NPC283117
0.6847 Remote Similarity NPC139763
0.6842 Remote Similarity NPC471980
0.6833 Remote Similarity NPC303951
0.6833 Remote Similarity NPC290689
0.6831 Remote Similarity NPC478045
0.6826 Remote Similarity NPC211920
0.6826 Remote Similarity NPC124029
0.6826 Remote Similarity NPC74575
0.6822 Remote Similarity NPC90229
0.682 Remote Similarity NPC107123
0.6818 Remote Similarity NPC39679
0.6818 Remote Similarity NPC210828
0.6818 Remote Similarity NPC90185
0.6818 Remote Similarity NPC86834
0.6816 Remote Similarity NPC271215
0.6816 Remote Similarity NPC149471
0.6814 Remote Similarity NPC48317
0.681 Remote Similarity NPC44354
0.6805 Remote Similarity NPC134637
0.6802 Remote Similarity NPC294375
0.6795 Remote Similarity NPC475406
0.6795 Remote Similarity NPC39370
0.6793 Remote Similarity NPC49672
0.6793 Remote Similarity NPC475844
0.6792 Remote Similarity NPC114335
0.6792 Remote Similarity NPC280964
0.6792 Remote Similarity NPC141915
0.6783 Remote Similarity NPC473506
0.6781 Remote Similarity NPC132329
0.6781 Remote Similarity NPC49547
0.6774 Remote Similarity NPC155792
0.6774 Remote Similarity NPC471489
0.6773 Remote Similarity NPC270918
0.6767 Remote Similarity NPC326363
0.6766 Remote Similarity NPC477549
0.6766 Remote Similarity NPC327904
0.6766 Remote Similarity NPC38959
0.6759 Remote Similarity NPC5374
0.6759 Remote Similarity NPC280714
0.6753 Remote Similarity NPC228377
0.6753 Remote Similarity NPC477787
0.6753 Remote Similarity NPC122968
0.6753 Remote Similarity NPC476110
0.6753 Remote Similarity NPC328186
0.6753 Remote Similarity NPC87152
0.6753 Remote Similarity NPC475631
0.6753 Remote Similarity NPC475600
0.6752 Remote Similarity NPC255800
0.6752 Remote Similarity NPC172222
0.6752 Remote Similarity NPC96584
0.6751 Remote Similarity NPC253482
0.6747 Remote Similarity NPC88923
0.6747 Remote Similarity NPC100734
0.6747 Remote Similarity NPC315634
0.674 Remote Similarity NPC216428
0.674 Remote Similarity NPC84815
0.674 Remote Similarity NPC301368
0.6739 Remote Similarity NPC477902
0.6739 Remote Similarity NPC473449
0.6739 Remote Similarity NPC328154
0.6738 Remote Similarity NPC150698
0.6738 Remote Similarity NPC96801
0.6738 Remote Similarity NPC201508
0.6725 Remote Similarity NPC122463
0.6724 Remote Similarity NPC274640
0.6724 Remote Similarity NPC471190
0.6724 Remote Similarity NPC475644
0.6724 Remote Similarity NPC470486
0.6724 Remote Similarity NPC471977
0.6723 Remote Similarity NPC327769
0.6716 Remote Similarity NPC477185
0.6716 Remote Similarity NPC471294
0.6714 Remote Similarity NPC195268
0.6714 Remote Similarity NPC99666
0.6714 Remote Similarity NPC133140
0.6712 Remote Similarity NPC134848
0.6711 Remote Similarity NPC118228
0.6709 Remote Similarity NPC473186

  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 NPC124086 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
0.743 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD6138 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD7395 Discontinued
0.7171 Intermediate Similarity NPD4948 Discontinued
0.7137 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD6376 Discontinued
0.7125 Intermediate Similarity NPD8091 Phase 3
0.7124 Intermediate Similarity NPD4845 Discontinued
0.7118 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD5866 Approved
0.7073 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.6974 Remote Similarity NPD7994 Phase 2
0.6972 Remote Similarity NPD2916 Discontinued
0.697 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6962 Phase 2
0.6907 Remote Similarity NPD6716 Phase 1
0.6907 Remote Similarity NPD1483 Discontinued
0.6893 Remote Similarity NPD5522 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7777 Approved
0.6869 Remote Similarity NPD53 Approved
0.6869 Remote Similarity NPD7778 Approved
0.6864 Remote Similarity NPD7417 Discontinued
0.6857 Remote Similarity NPD7708 Approved
0.6844 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6456 Discontinued
0.6822 Remote Similarity NPD7948 Phase 1
0.6797 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6781 Remote Similarity NPD3746 Discontinued
0.6773 Remote Similarity NPD7222 Phase 2
0.6758 Remote Similarity NPD6987 Phase 1
0.6756 Remote Similarity NPD8149 Discontinued
0.6753 Remote Similarity NPD3259 Approved
0.6752 Remote Similarity NPD4373 Phase 2
0.6747 Remote Similarity NPD7803 Approved
0.6743 Remote Similarity NPD6975 Discontinued
0.6741 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6729 Remote Similarity NPD5975 Clinical (unspecified phase)
0.6714 Remote Similarity NPD3923 Approved
0.6714 Remote Similarity NPD3922 Approved
0.6714 Remote Similarity NPD3921 Approved
0.6714 Remote Similarity NPD3924 Approved
0.6711 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6711 Remote Similarity NPD7180 Phase 3
0.6709 Remote Similarity NPD5151 Clinical (unspecified phase)
0.6697 Remote Similarity NPD5429 Discontinued
0.6697 Remote Similarity NPD7452 Approved
0.6697 Remote Similarity NPD7453 Approved
0.6696 Remote Similarity NPD7878 Phase 2
0.6682 Remote Similarity NPD5901 Discontinued
0.6681 Remote Similarity NPD8016 Phase 3
0.6681 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5805 Approved
0.6667 Remote Similarity NPD3258 Approved
0.6667 Remote Similarity NPD3920 Phase 2
0.6653 Remote Similarity NPD8463 Approved
0.6651 Remote Similarity NPD4418 Discontinued
0.6651 Remote Similarity NPD5497 Clinical (unspecified phase)
0.6638 Remote Similarity NPD6242 Discontinued
0.6636 Remote Similarity NPD5968 Phase 3
0.6635 Remote Similarity NPD1643 Phase 3
0.6627 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6625 Remote Similarity NPD6517 Phase 3
0.6624 Remote Similarity NPD4952 Phase 3
0.6624 Remote Similarity NPD7853 Phase 2
0.6623 Remote Similarity NPD7547 Clinical (unspecified phase)
0.662 Remote Similarity NPD6836 Approved
0.6612 Remote Similarity NPD5488 Discontinued
0.6609 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6607 Remote Similarity NPD5914 Approved
0.6606 Remote Similarity NPD5608 Approved
0.6606 Remote Similarity NPD5609 Approved
0.6606 Remote Similarity NPD8395 Approved
0.6606 Remote Similarity NPD8396 Approved
0.6605 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6603 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6598 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6595 Remote Similarity NPD7586 Clinical (unspecified phase)
0.6594 Remote Similarity NPD7203 Clinical (unspecified phase)
0.6594 Remote Similarity NPD3763 Approved
0.6587 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6585 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6584 Remote Similarity NPD1631 Approved
0.6581 Remote Similarity NPD7654 Discontinued
0.658 Remote Similarity NPD6995 Phase 1
0.6579 Remote Similarity NPD4989 Phase 2
0.6575 Remote Similarity NPD484 Approved
0.657 Remote Similarity NPD7921 Approved
0.6561 Remote Similarity NPD7924 Phase 2
0.6561 Remote Similarity NPD7925 Phase 2
0.6557 Remote Similarity NPD8350 Clinical (unspecified phase)
0.6555 Remote Similarity NPD5445 Approved
0.6549 Remote Similarity NPD3815 Phase 1
0.6549 Remote Similarity NPD7069 Discontinued
0.6549 Remote Similarity NPD8093 Discontinued
0.6549 Remote Similarity NPD3816 Phase 1
0.6546 Remote Similarity NPD7955 Approved
0.6546 Remote Similarity NPD7956 Approved
0.6545 Remote Similarity NPD4511 Phase 1
0.6542 Remote Similarity NPD4561 Discontinued
0.6538 Remote Similarity NPD4328 Approved
0.6535 Remote Similarity NPD6733 Discontinued
0.6533 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7449 Clinical (unspecified phase)
0.6522 Remote Similarity NPD4736 Clinical (unspecified phase)
0.652 Remote Similarity NPD8094 Discontinued
0.6515 Remote Similarity NPD6790 Phase 1
0.6502 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6496 Remote Similarity NPD3263 Phase 3
0.6494 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6491 Remote Similarity NPD4897 Phase 2
0.6491 Remote Similarity NPD3257 Approved
0.649 Remote Similarity NPD8102 Discontinued
0.6488 Remote Similarity NPD2781 Approved
0.6484 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6482 Remote Similarity NPD3229 Phase 2
0.6476 Remote Similarity NPD6452 Discontinued
0.6473 Remote Similarity NPD7886 Phase 2
0.6473 Remote Similarity NPD7885 Phase 2
0.6471 Remote Similarity NPD2782 Approved
0.6471 Remote Similarity NPD2780 Approved
0.6471 Remote Similarity NPD7922 Phase 1
0.6466 Remote Similarity NPD5506 Approved
0.6466 Remote Similarity NPD5507 Approved
0.6465 Remote Similarity NPD5928 Phase 1
0.6463 Remote Similarity NPD7588 Discontinued
0.6462 Remote Similarity NPD7181 Phase 3
0.6462 Remote Similarity NPD7546 Discontinued
0.6459 Remote Similarity NPD6159 Phase 2
0.6456 Remote Similarity NPD1575 Approved
0.6456 Remote Similarity NPD8238 Clinical (unspecified phase)
0.6456 Remote Similarity NPD1573 Approved
0.6455 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6455 Remote Similarity NPD6999 Discontinued
0.6453 Remote Similarity NPD3925 Approved
0.645 Remote Similarity NPD6974 Phase 3
0.6447 Remote Similarity NPD3243 Approved
0.6445 Remote Similarity NPD5031 Approved
0.6445 Remote Similarity NPD5029 Approved
0.6445 Remote Similarity NPD5027 Approved
0.6444 Remote Similarity NPD7300 Phase 3
0.6444 Remote Similarity NPD7302 Phase 3
0.6444 Remote Similarity NPD4859 Phase 1
0.6441 Remote Similarity NPD7767 Approved
0.6438 Remote Similarity NPD8356 Approved
0.6438 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6436 Remote Similarity NPD1630 Approved
0.6435 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4885 Approved
0.6429 Remote Similarity NPD6807 Phase 3
0.6426 Remote Similarity NPD7603 Discontinued
0.6425 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6423 Remote Similarity NPD7658 Phase 2
0.6419 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6409 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6407 Remote Similarity NPD3354 Phase 2
0.6407 Remote Similarity NPD8109 Clinical (unspecified phase)
0.6406 Remote Similarity NPD4941 Clinical (unspecified phase)
0.6406 Remote Similarity NPD5937 Approved
0.6404 Remote Similarity NPD7301 Phase 3
0.6402 Remote Similarity NPD5809 Phase 3
0.6396 Remote Similarity NPD2420 Approved
0.6396 Remote Similarity NPD2421 Approved
0.6393 Remote Similarity NPD5512 Phase 3
0.6391 Remote Similarity NPD2433 Clinical (unspecified phase)
0.6384 Remote Similarity NPD6323 Clinical (unspecified phase)
0.638 Remote Similarity NPD6137 Clinical (unspecified phase)
0.6379 Remote Similarity NPD4312 Approved
0.6375 Remote Similarity NPD5050 Approved
0.6372 Remote Similarity NPD7665 Phase 2
0.6372 Remote Similarity NPD7666 Phase 3
0.6371 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6368 Remote Similarity NPD7187 Phase 2
0.6368 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6367 Remote Similarity NPD3962 Phase 2
0.6367 Remote Similarity NPD3959 Phase 2
0.636 Remote Similarity NPD7703 Clinical (unspecified phase)
0.636 Remote Similarity NPD5416 Discontinued
0.636 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6359 Remote Similarity NPD5849 Approved
0.6356 Remote Similarity NPD7568 Phase 1
0.6352 Remote Similarity NPD5850 Phase 3
0.6345 Remote Similarity NPD3845 Phase 1
0.6345 Remote Similarity NPD5022 Discontinued
0.6343 Remote Similarity NPD6965 Clinical (unspecified phase)
0.6336 Remote Similarity NPD4429 Discontinued
0.6333 Remote Similarity NPD5471 Phase 3
0.6332 Remote Similarity NPD7225 Discontinued
0.6331 Remote Similarity NPD3986 Discontinued
0.6331 Remote Similarity NPD3809 Discontinued
0.6329 Remote Similarity NPD8430 Approved
0.6329 Remote Similarity NPD7694 Discontinued
0.6325 Remote Similarity NPD4923 Phase 1
0.6325 Remote Similarity NPD7556 Discontinued
0.6324 Remote Similarity NPD5978 Approved
0.6324 Remote Similarity NPD5977 Approved
0.6321 Remote Similarity NPD5897 Approved
0.6321 Remote Similarity NPD5899 Approved
0.6321 Remote Similarity NPD5898 Approved
0.632 Remote Similarity NPD5612 Discontinued
0.6318 Remote Similarity NPD1505 Phase 2

  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