Structure

Physi-Chem Properties

Molecular Weight:  545.2
Volume:  545.711
LogP:  4.286
LogD:  3.501
LogS:  -5.936
# Rotatable Bonds:  7
TPSA:  89.77
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.317
Synthetic Accessibility Score:  3.054
Fsp3:  0.29
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.481
MDCK Permeability:  5.1076927775284275e-05
Pgp-inhibitor:  0.975
Pgp-substrate:  0.758
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  75.1065444946289%
Volume Distribution (VD):  0.48
Pgp-substrate:  6.930362224578857%

ADMET: Metabolism

CYP1A2-inhibitor:  0.074
CYP1A2-substrate:  0.987
CYP2C19-inhibitor:  0.673
CYP2C19-substrate:  0.868
CYP2C9-inhibitor:  0.747
CYP2C9-substrate:  0.933
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.963
CYP3A4-inhibitor:  0.321
CYP3A4-substrate:  0.916

ADMET: Excretion

Clearance (CL):  9.33
Half-life (T1/2):  0.48

ADMET: Toxicity

hERG Blockers:  0.17
Human Hepatotoxicity (H-HT):  0.123
Drug-inuced Liver Injury (DILI):  0.933
AMES Toxicity:  0.351
Rat Oral Acute Toxicity:  0.103
Maximum Recommended Daily Dose:  0.736
Skin Sensitization:  0.03
Carcinogencity:  0.047
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.497

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

  Natural Product: NPC476998

Natural Product ID:  NPC476998
Common Name*:   12-(3,4-Dimethoxyphenyl)-8,16,17,18-tetramethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaen-7-ol
IUPAC Name:   12-(3,4-dimethoxyphenyl)-8,16,17,18-tetramethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaen-7-ol
Synonyms:   Lamellarin I
Standard InCHIKey:  DJAQGPQDRCRBFP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C31H31NO8/c1-34-22-8-7-16(11-25(22)36-3)27-28-19-13-24(35-2)21(33)14-23(19)40-15-20(28)32-10-9-17-18(29(27)32)12-26(37-4)31(39-6)30(17)38-5/h7-8,11-14,33H,9-10,15H2,1-6H3
SMILES:  COC1=C(C=C(C=C1)C2=C3C4=CC(=C(C(=C4CCN3C5=C2C6=CC(=C(C=C6OC5)O)OC)OC)OC)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   44559516
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000090] Pyrroles
        • [CHEMONTID:0002257] Substituted pyrroles
          • [CHEMONTID:0002334] Phenylpyrroles

*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
NPO16570 Didemnum obscurum Species Didemnidae Eukaryota n.a. Tiruchandur coast in the Gulf of Mannar, Tamilnadu, India 2002-FEB PMID[15270574]
NPO16570 Didemnum obscurum Species Didemnidae 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
NPT1 Others Radical scavenging activity Activity = 1.93 % PMID[15270574]
NPT1 Others Radical scavenging activity Activity = 75.11 % PMID[15270574]
NPT1 Others Radical scavenging activity Activity = 159.2 % PMID[15270574]
NPT1 Others Radical scavenging activity Activity = 237.81 % PMID[15270574]
NPT1 Others Radical scavenging activity Activity = 316.41 % PMID[15270574]
NPT1 Others Radical scavenging activity IC50 = 2960000 nM PMID[15270574]
NPT2 Others Unspecified Ratio IC50 = 0.02 n.a. PMID[15270574]

☑ 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 NPC476998 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 NPC476996
0.9951 High Similarity NPC476997
0.9951 High Similarity NPC476994
0.9619 High Similarity NPC476995
0.9289 High Similarity NPC476999
0.8652 High Similarity NPC129897
0.8591 High Similarity NPC96584
0.8591 High Similarity NPC255800
0.8584 High Similarity NPC201508
0.8419 Intermediate Similarity NPC473822
0.8271 Intermediate Similarity NPC202605
0.8271 Intermediate Similarity NPC112206
0.8265 Intermediate Similarity NPC122463
0.8257 Intermediate Similarity NPC174049
0.8248 Intermediate Similarity NPC318068
0.8211 Intermediate Similarity NPC148409
0.8113 Intermediate Similarity NPC164374
0.8113 Intermediate Similarity NPC137929
0.8095 Intermediate Similarity NPC284141
0.8065 Intermediate Similarity NPC474594
0.8043 Intermediate Similarity NPC217554
0.8018 Intermediate Similarity NPC203168
0.8009 Intermediate Similarity NPC219664
0.7991 Intermediate Similarity NPC200888
0.7981 Intermediate Similarity NPC469440
0.7972 Intermediate Similarity NPC31930
0.7957 Intermediate Similarity NPC11408
0.7944 Intermediate Similarity NPC16452
0.7944 Intermediate Similarity NPC36229
0.7944 Intermediate Similarity NPC476581
0.7926 Intermediate Similarity NPC290689
0.7885 Intermediate Similarity NPC469390
0.7885 Intermediate Similarity NPC469792
0.7877 Intermediate Similarity NPC4071
0.7877 Intermediate Similarity NPC476578
0.7877 Intermediate Similarity NPC476582
0.787 Intermediate Similarity NPC474595
0.7857 Intermediate Similarity NPC118121
0.7857 Intermediate Similarity NPC85381
0.7854 Intermediate Similarity NPC202768
0.7854 Intermediate Similarity NPC53069
0.7854 Intermediate Similarity NPC296482
0.785 Intermediate Similarity NPC66815
0.7838 Intermediate Similarity NPC204446
0.7824 Intermediate Similarity NPC304183
0.7788 Intermediate Similarity NPC313189
0.7762 Intermediate Similarity NPC318805
0.7762 Intermediate Similarity NPC41122
0.7759 Intermediate Similarity NPC473183
0.77 Intermediate Similarity NPC234318
0.7699 Intermediate Similarity NPC280272
0.7692 Intermediate Similarity NPC61350
0.7692 Intermediate Similarity NPC96405
0.7692 Intermediate Similarity NPC171409
0.7679 Intermediate Similarity NPC100079
0.7679 Intermediate Similarity NPC23614
0.7678 Intermediate Similarity NPC280964
0.7678 Intermediate Similarity NPC133140
0.7678 Intermediate Similarity NPC114335
0.7678 Intermediate Similarity NPC195268
0.7678 Intermediate Similarity NPC141915
0.7672 Intermediate Similarity NPC473184
0.7672 Intermediate Similarity NPC277351
0.7671 Intermediate Similarity NPC470931
0.7658 Intermediate Similarity NPC149471
0.7658 Intermediate Similarity NPC271215
0.7626 Intermediate Similarity NPC135549
0.7619 Intermediate Similarity NPC212237
0.7619 Intermediate Similarity NPC116465
0.7595 Intermediate Similarity NPC15406
0.7593 Intermediate Similarity NPC477019
0.7585 Intermediate Similarity NPC49672
0.758 Intermediate Similarity NPC472111
0.7566 Intermediate Similarity NPC46451
0.756 Intermediate Similarity NPC30779
0.7559 Intermediate Similarity NPC79293
0.7559 Intermediate Similarity NPC279401
0.7552 Intermediate Similarity NPC302807
0.7545 Intermediate Similarity NPC235076
0.7535 Intermediate Similarity NPC224928
0.7523 Intermediate Similarity NPC188420
0.7512 Intermediate Similarity NPC286119
0.75 Intermediate Similarity NPC22115
0.75 Intermediate Similarity NPC266931
0.75 Intermediate Similarity NPC275680
0.7489 Intermediate Similarity NPC295228
0.7488 Intermediate Similarity NPC249996
0.7479 Intermediate Similarity NPC77878
0.7479 Intermediate Similarity NPC473182
0.7479 Intermediate Similarity NPC183537
0.7477 Intermediate Similarity NPC469589
0.7476 Intermediate Similarity NPC181796
0.7476 Intermediate Similarity NPC182052
0.7476 Intermediate Similarity NPC290005
0.7476 Intermediate Similarity NPC311973
0.7476 Intermediate Similarity NPC42663
0.7476 Intermediate Similarity NPC271013
0.7476 Intermediate Similarity NPC49075
0.7476 Intermediate Similarity NPC8836
0.7476 Intermediate Similarity NPC104196
0.7476 Intermediate Similarity NPC239824
0.7476 Intermediate Similarity NPC290582
0.7476 Intermediate Similarity NPC328155
0.7476 Intermediate Similarity NPC222661
0.7476 Intermediate Similarity NPC251735
0.7476 Intermediate Similarity NPC90998
0.7476 Intermediate Similarity NPC7715
0.7476 Intermediate Similarity NPC476202
0.7476 Intermediate Similarity NPC54654
0.7476 Intermediate Similarity NPC229373
0.7476 Intermediate Similarity NPC15414
0.7476 Intermediate Similarity NPC258657
0.7476 Intermediate Similarity NPC217748
0.7476 Intermediate Similarity NPC185639
0.7476 Intermediate Similarity NPC279228
0.7476 Intermediate Similarity NPC223690
0.7476 Intermediate Similarity NPC285931
0.7455 Intermediate Similarity NPC251160
0.7441 Intermediate Similarity NPC167116
0.7441 Intermediate Similarity NPC274716
0.7441 Intermediate Similarity NPC254441
0.744 Intermediate Similarity NPC232386
0.744 Intermediate Similarity NPC152680
0.744 Intermediate Similarity NPC190783
0.7439 Intermediate Similarity NPC284685
0.7438 Intermediate Similarity NPC134637
0.7437 Intermediate Similarity NPC119134
0.7431 Intermediate Similarity NPC234197
0.7429 Intermediate Similarity NPC195538
0.7414 Intermediate Similarity NPC473185
0.7409 Intermediate Similarity NPC191489
0.7407 Intermediate Similarity NPC473053
0.7406 Intermediate Similarity NPC16357
0.7406 Intermediate Similarity NPC95426
0.7406 Intermediate Similarity NPC302245
0.7395 Intermediate Similarity NPC24260
0.7383 Intermediate Similarity NPC206900
0.738 Intermediate Similarity NPC132642
0.738 Intermediate Similarity NPC469439
0.738 Intermediate Similarity NPC54066
0.7371 Intermediate Similarity NPC139783
0.7371 Intermediate Similarity NPC65312
0.7364 Intermediate Similarity NPC135887
0.7364 Intermediate Similarity NPC199277
0.7361 Intermediate Similarity NPC473589
0.7361 Intermediate Similarity NPC478092
0.7361 Intermediate Similarity NPC478091
0.7361 Intermediate Similarity NPC30182
0.7358 Intermediate Similarity NPC472589
0.7352 Intermediate Similarity NPC11017
0.7343 Intermediate Similarity NPC312872
0.7315 Intermediate Similarity NPC478093
0.7314 Intermediate Similarity NPC107123
0.7302 Intermediate Similarity NPC175890
0.7302 Intermediate Similarity NPC274661
0.7302 Intermediate Similarity NPC11296
0.7302 Intermediate Similarity NPC48490
0.7302 Intermediate Similarity NPC82457
0.73 Intermediate Similarity NPC90875
0.7297 Intermediate Similarity NPC210256
0.7296 Intermediate Similarity NPC214980
0.7295 Intermediate Similarity NPC204908
0.7295 Intermediate Similarity NPC83198
0.7293 Intermediate Similarity NPC173080
0.7293 Intermediate Similarity NPC469594
0.7291 Intermediate Similarity NPC315634
0.7291 Intermediate Similarity NPC88923
0.7291 Intermediate Similarity NPC100734
0.7288 Intermediate Similarity NPC233334
0.7286 Intermediate Similarity NPC293093
0.7282 Intermediate Similarity NPC13916
0.7282 Intermediate Similarity NPC264850
0.7276 Intermediate Similarity NPC472588
0.7273 Intermediate Similarity NPC124313
0.7269 Intermediate Similarity NPC191132
0.7269 Intermediate Similarity NPC60295
0.7265 Intermediate Similarity NPC67401
0.7264 Intermediate Similarity NPC62069
0.7257 Intermediate Similarity NPC329631
0.7253 Intermediate Similarity NPC473449
0.7252 Intermediate Similarity NPC475774
0.7246 Intermediate Similarity NPC475253
0.7244 Intermediate Similarity NPC101312
0.7243 Intermediate Similarity NPC66083
0.7235 Intermediate Similarity NPC78284
0.7234 Intermediate Similarity NPC252251
0.7233 Intermediate Similarity NPC24465
0.7231 Intermediate Similarity NPC160100
0.722 Intermediate Similarity NPC47059
0.722 Intermediate Similarity NPC165349
0.722 Intermediate Similarity NPC210296
0.722 Intermediate Similarity NPC274291
0.722 Intermediate Similarity NPC329708
0.722 Intermediate Similarity NPC264166
0.722 Intermediate Similarity NPC118832
0.7209 Intermediate Similarity NPC477186
0.7209 Intermediate Similarity NPC320088
0.7202 Intermediate Similarity NPC256124
0.7196 Intermediate Similarity NPC204385
0.7195 Intermediate Similarity NPC475654

  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 NPC476998 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
0.8294 Intermediate Similarity NPD7222 Phase 2
0.8233 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD7452 Approved
0.8037 Intermediate Similarity NPD7453 Approved
0.7983 Intermediate Similarity NPD7169 Suspended
0.7939 Intermediate Similarity NPD6494 Phase 2
0.7854 Intermediate Similarity NPD3816 Phase 1
0.7854 Intermediate Similarity NPD3815 Phase 1
0.7828 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD5902 Approved
0.7703 Intermediate Similarity NPD5903 Approved
0.7678 Intermediate Similarity NPD3921 Approved
0.7678 Intermediate Similarity NPD3923 Approved
0.7678 Intermediate Similarity NPD3922 Approved
0.7678 Intermediate Similarity NPD3924 Approved
0.766 Intermediate Similarity NPD7417 Discontinued
0.7659 Intermediate Similarity NPD3920 Phase 2
0.7566 Intermediate Similarity NPD3763 Approved
0.7565 Intermediate Similarity NPD6553 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD7558 Phase 2
0.7512 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.751 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7476 Intermediate Similarity NPD8054 Approved
0.7476 Intermediate Similarity NPD8053 Approved
0.7442 Intermediate Similarity NPD4418 Discontinued
0.7439 Intermediate Similarity NPD7955 Approved
0.7439 Intermediate Similarity NPD7956 Approved
0.7434 Intermediate Similarity NPD5612 Discontinued
0.743 Intermediate Similarity NPD6569 Phase 2
0.7411 Intermediate Similarity NPD4502 Phase 2
0.7409 Intermediate Similarity NPD7708 Approved
0.7377 Intermediate Similarity NPD7859 Phase 2
0.7361 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD5658 Approved
0.7342 Intermediate Similarity NPD5530 Phase 1
0.7309 Intermediate Similarity NPD7862 Clinical (unspecified phase)
0.7309 Intermediate Similarity NPD5429 Discontinued
0.7308 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD7395 Discontinued
0.7291 Intermediate Similarity NPD7803 Approved
0.7277 Intermediate Similarity NPD5256 Discontinued
0.7265 Intermediate Similarity NPD3003 Approved
0.7265 Intermediate Similarity NPD4305 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD7194 Discontinued
0.7257 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD7719 Discontinued
0.7251 Intermediate Similarity NPD4203 Approved
0.7251 Intermediate Similarity NPD4204 Approved
0.7248 Intermediate Similarity NPD6550 Discontinued
0.7243 Intermediate Similarity NPD6257 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD6361 Phase 2
0.7227 Intermediate Similarity NPD3837 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD7069 Discontinued
0.7222 Intermediate Similarity NPD7675 Phase 3
0.7222 Intermediate Similarity NPD7674 Phase 3
0.7222 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.722 Intermediate Similarity NPD32 Approved
0.722 Intermediate Similarity NPD4038 Approved
0.722 Intermediate Similarity NPD4122 Approved
0.722 Intermediate Similarity NPD4034 Approved
0.722 Intermediate Similarity NPD4037 Approved
0.722 Intermediate Similarity NPD4033 Approved
0.722 Intermediate Similarity NPD4039 Approved
0.722 Intermediate Similarity NPD4036 Approved
0.722 Intermediate Similarity NPD4035 Approved
0.722 Intermediate Similarity NPD31 Approved
0.7217 Intermediate Similarity NPD6985 Discontinued
0.7202 Intermediate Similarity NPD6590 Discontinued
0.7202 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD6716 Phase 1
0.719 Intermediate Similarity NPD1483 Discontinued
0.719 Intermediate Similarity NPD8156 Discontinued
0.7188 Intermediate Similarity NPD3842 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD5930 Phase 3
0.715 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8251 Approved
0.7143 Intermediate Similarity NPD8099 Discontinued
0.7143 Intermediate Similarity NPD8252 Approved
0.7143 Intermediate Similarity NPD8109 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD7906 Approved
0.7121 Intermediate Similarity NPD7682 Approved
0.7121 Intermediate Similarity NPD7684 Approved
0.7118 Intermediate Similarity NPD5945 Phase 1
0.7118 Intermediate Similarity NPD5944 Phase 1
0.7113 Intermediate Similarity NPD4080 Discontinued
0.7112 Intermediate Similarity NPD3875 Discontinued
0.7105 Intermediate Similarity NPD4131 Phase 3
0.71 Intermediate Similarity NPD5164 Discontinued
0.7091 Intermediate Similarity NPD5512 Phase 3
0.7083 Intermediate Similarity NPD6963 Approved
0.7083 Intermediate Similarity NPD6964 Approved
0.7082 Intermediate Similarity NPD7678 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7426 Phase 1
0.7059 Intermediate Similarity NPD6988 Phase 1
0.7054 Intermediate Similarity NPD6477 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD5863 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD7571 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD8442 Discontinued
0.7031 Intermediate Similarity NPD6220 Phase 3
0.7028 Intermediate Similarity NPD6159 Phase 2
0.7021 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD3477 Phase 2
0.7014 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD3386 Phase 2
0.7009 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.7004 Intermediate Similarity NPD6290 Phase 2
0.7 Intermediate Similarity NPD4551 Phase 2
0.6996 Remote Similarity NPD1768 Approved
0.6975 Remote Similarity NPD6327 Phase 1
0.6975 Remote Similarity NPD6326 Phase 2
0.6974 Remote Similarity NPD7672 Approved
0.6974 Remote Similarity NPD7671 Approved
0.6964 Remote Similarity NPD8359 Phase 2
0.6961 Remote Similarity NPD4678 Approved
0.6961 Remote Similarity NPD4675 Approved
0.6951 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6948 Remote Similarity NPD8101 Phase 3
0.6944 Remote Similarity NPD8244 Phase 2
0.694 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6929 Remote Similarity NPD4885 Approved
0.6927 Remote Similarity NPD4663 Approved
0.6926 Remote Similarity NPD4927 Discontinued
0.6923 Remote Similarity NPD6568 Discontinued
0.692 Remote Similarity NPD2177 Approved
0.692 Remote Similarity NPD2175 Phase 3
0.692 Remote Similarity NPD2176 Approved
0.6917 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6916 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6911 Remote Similarity NPD4875 Phase 3
0.6911 Remote Similarity NPD4876 Phase 3
0.6906 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6904 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6898 Remote Similarity NPD5522 Clinical (unspecified phase)
0.6898 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6898 Remote Similarity NPD8016 Phase 3
0.6894 Remote Similarity NPD3514 Clinical (unspecified phase)
0.6889 Remote Similarity NPD6219 Discontinued
0.6883 Remote Similarity NPD5066 Phase 2
0.6883 Remote Similarity NPD5936 Approved
0.6883 Remote Similarity NPD5939 Approved
0.6883 Remote Similarity NPD5067 Phase 2
0.6881 Remote Similarity NPD4375 Approved
0.688 Remote Similarity NPD6243 Phase 3
0.688 Remote Similarity NPD6244 Phase 3
0.6878 Remote Similarity NPD1856 Discontinued
0.6875 Remote Similarity NPD7555 Discontinued
0.6872 Remote Similarity NPD4724 Clinical (unspecified phase)
0.6872 Remote Similarity NPD6991 Approved
0.6867 Remote Similarity NPD7868 Clinical (unspecified phase)
0.6866 Remote Similarity NPD4578 Approved
0.6866 Remote Similarity NPD4577 Approved
0.6864 Remote Similarity NPD7180 Phase 3
0.6862 Remote Similarity NPD3263 Phase 3
0.6857 Remote Similarity NPD7729 Clinical (unspecified phase)
0.6856 Remote Similarity NPD1392 Approved
0.6856 Remote Similarity NPD7263 Phase 2
0.6855 Remote Similarity NPD6230 Discontinued
0.6854 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6853 Remote Similarity NPD5866 Approved
0.6852 Remote Similarity NPD3037 Phase 1
0.685 Remote Similarity NPD8091 Phase 3
0.6846 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6846 Remote Similarity NPD7567 Approved
0.6844 Remote Similarity NPD4118 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6517 Phase 3
0.6842 Remote Similarity NPD3397 Phase 2
0.6838 Remote Similarity NPD6147 Clinical (unspecified phase)
0.6835 Remote Similarity NPD4889 Approved
0.6835 Remote Similarity NPD5506 Approved
0.6835 Remote Similarity NPD5507 Approved
0.683 Remote Similarity NPD6769 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7885 Phase 2
0.6829 Remote Similarity NPD7886 Phase 2
0.6828 Remote Similarity NPD6975 Discontinued
0.6827 Remote Similarity NPD8100 Phase 3
0.6822 Remote Similarity NPD6974 Phase 3
0.682 Remote Similarity NPD6246 Approved
0.6816 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6814 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6807 Remote Similarity NPD6736 Discontinued
0.6803 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6797 Remote Similarity NPD4437 Phase 3
0.6793 Remote Similarity NPD3590 Clinical (unspecified phase)
0.6793 Remote Similarity NPD6856 Discontinued
0.6784 Remote Similarity NPD6592 Clinical (unspecified phase)
0.6777 Remote Similarity NPD7201 Clinical (unspecified phase)
0.6776 Remote Similarity NPD5938 Phase 3
0.6773 Remote Similarity NPD1034 Phase 3
0.6773 Remote Similarity NPD1033 Clinical (unspecified phase)
0.6761 Remote Similarity NPD4083 Discontinued
0.6756 Remote Similarity NPD4604 Approved
0.6756 Remote Similarity NPD4605 Approved
0.6756 Remote Similarity NPD1229 Phase 2
0.6751 Remote Similarity NPD6501 Approved
0.6751 Remote Similarity NPD2899 Discontinued
0.6751 Remote Similarity NPD6500 Approved
0.6749 Remote Similarity NPD6962 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