Structure

Physi-Chem Properties

Molecular Weight:  450.17
Volume:  460.293
LogP:  4.714
LogD:  3.755
LogS:  -6.146
# Rotatable Bonds:  6
TPSA:  92.89
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.323
Synthetic Accessibility Score:  2.87
Fsp3:  0.148
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.295
MDCK Permeability:  9.286857675760984e-06
Pgp-inhibitor:  0.93
Pgp-substrate:  0.281
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.078
Plasma Protein Binding (PPB):  94.83328247070312%
Volume Distribution (VD):  0.919
Pgp-substrate:  3.874763011932373%

ADMET: Metabolism

CYP1A2-inhibitor:  0.982
CYP1A2-substrate:  0.971
CYP2C19-inhibitor:  0.958
CYP2C19-substrate:  0.179
CYP2C9-inhibitor:  0.958
CYP2C9-substrate:  0.912
CYP2D6-inhibitor:  0.878
CYP2D6-substrate:  0.898
CYP3A4-inhibitor:  0.855
CYP3A4-substrate:  0.673

ADMET: Excretion

Clearance (CL):  3.897
Half-life (T1/2):  0.259

ADMET: Toxicity

hERG Blockers:  0.329
Human Hepatotoxicity (H-HT):  0.964
Drug-inuced Liver Injury (DILI):  0.986
AMES Toxicity:  0.724
Rat Oral Acute Toxicity:  0.988
Maximum Recommended Daily Dose:  0.906
Skin Sensitization:  0.569
Carcinogencity:  0.505
Eye Corrosion:  0.003
Eye Irritation:  0.055
Respiratory Toxicity:  0.992

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  Natural Product: NPC53534

Natural Product ID:  NPC53534
Common Name*:   Beta-Carboline-1-Yl-4,8-Dimethoxy-Beta-Carboline-1-Ylethyl Ketone
IUPAC Name:   3-(4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-1-(9H-pyrido[3,4-b]indol-1-yl)propan-1-one
Synonyms:  
Standard InCHIKey:  MSRXRROCBIUJCG-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C27H22N4O3/c1-33-21-9-5-7-17-23-22(34-2)14-29-19(26(23)31-24(17)21)10-11-20(32)27-25-16(12-13-28-27)15-6-3-4-8-18(15)30-25/h3-9,12-14,30-31H,10-11H2,1-2H3
SMILES:  COc1cccc2c1[nH]c1c2c(OC)cnc1CCC(=O)c1nccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2229722
PubChem CID:   5315686
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001140] Harmala alkaloids

*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
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. seed n.a. DOI[10.1016/S0031-9422(99)00216-2]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19586051]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota stems n.a. n.a. PMID[20095629]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[25506718]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota seeds and root bark Henan, China n.a. PMID[26295746]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[27494664]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[30917277]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8372 Picrasma quassioides Species Simaroubaceae 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
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus EC50 = 78000.0 nM PMID[528276]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus EC50 = 131000.0 nM PMID[528276]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 68.3 % PMID[528276]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 45.5 % PMID[528276]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 64.8 % PMID[528276]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 28.9 % PMID[528276]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 52.4 % PMID[528276]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 39.4 % PMID[528276]

☑ 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 NPC53534 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
0.9654 High Similarity NPC152620
0.8899 High Similarity NPC469554
0.8899 High Similarity NPC101543
0.8874 High Similarity NPC148889
0.8788 High Similarity NPC101350
0.8771 High Similarity NPC26543
0.8745 High Similarity NPC235685
0.8554 High Similarity NPC258048
0.8494 Intermediate Similarity NPC91868
0.8494 Intermediate Similarity NPC63971
0.8448 Intermediate Similarity NPC260434
0.8428 Intermediate Similarity NPC122436
0.8362 Intermediate Similarity NPC314954
0.834 Intermediate Similarity NPC182222
0.8311 Intermediate Similarity NPC26679
0.8259 Intermediate Similarity NPC185782
0.8178 Intermediate Similarity NPC207686
0.8178 Intermediate Similarity NPC473186
0.8178 Intermediate Similarity NPC196718
0.8109 Intermediate Similarity NPC39370
0.8101 Intermediate Similarity NPC102593
0.806 Intermediate Similarity NPC323969
0.8043 Intermediate Similarity NPC8022
0.8043 Intermediate Similarity NPC470799
0.8042 Intermediate Similarity NPC15801
0.8036 Intermediate Similarity NPC476138
0.8036 Intermediate Similarity NPC245816
0.8034 Intermediate Similarity NPC229893
0.8008 Intermediate Similarity NPC165964
0.7992 Intermediate Similarity NPC141053
0.7974 Intermediate Similarity NPC266249
0.794 Intermediate Similarity NPC288987
0.7904 Intermediate Similarity NPC167860
0.7904 Intermediate Similarity NPC123839
0.7904 Intermediate Similarity NPC123976
0.7902 Intermediate Similarity NPC19872
0.7886 Intermediate Similarity NPC178858
0.7879 Intermediate Similarity NPC476287
0.7875 Intermediate Similarity NPC49547
0.7872 Intermediate Similarity NPC60621
0.7857 Intermediate Similarity NPC478078
0.7842 Intermediate Similarity NPC329631
0.7835 Intermediate Similarity NPC118940
0.7811 Intermediate Similarity NPC36405
0.7795 Intermediate Similarity NPC196449
0.7795 Intermediate Similarity NPC314222
0.7787 Intermediate Similarity NPC213530
0.7787 Intermediate Similarity NPC193267
0.7782 Intermediate Similarity NPC74575
0.7778 Intermediate Similarity NPC27041
0.7764 Intermediate Similarity NPC216612
0.7746 Intermediate Similarity NPC240384
0.7741 Intermediate Similarity NPC470018
0.7717 Intermediate Similarity NPC74619
0.7708 Intermediate Similarity NPC257851
0.7702 Intermediate Similarity NPC208522
0.7702 Intermediate Similarity NPC305984
0.7692 Intermediate Similarity NPC473312
0.7686 Intermediate Similarity NPC132539
0.7682 Intermediate Similarity NPC94157
0.7679 Intermediate Similarity NPC276657
0.7676 Intermediate Similarity NPC194740
0.7665 Intermediate Similarity NPC176538
0.7657 Intermediate Similarity NPC322482
0.7639 Intermediate Similarity NPC187501
0.7638 Intermediate Similarity NPC478083
0.759 Intermediate Similarity NPC142385
0.7586 Intermediate Similarity NPC287208
0.7574 Intermediate Similarity NPC39500
0.7565 Intermediate Similarity NPC317701
0.7565 Intermediate Similarity NPC475774
0.7563 Intermediate Similarity NPC208084
0.7562 Intermediate Similarity NPC157931
0.7561 Intermediate Similarity NPC477549
0.7555 Intermediate Similarity NPC232727
0.7542 Intermediate Similarity NPC477979
0.754 Intermediate Similarity NPC270515
0.7533 Intermediate Similarity NPC267928
0.7532 Intermediate Similarity NPC285558
0.7531 Intermediate Similarity NPC225279
0.753 Intermediate Similarity NPC472061
0.7511 Intermediate Similarity NPC322064
0.75 Intermediate Similarity NPC161801
0.75 Intermediate Similarity NPC41679
0.75 Intermediate Similarity NPC310118
0.749 Intermediate Similarity NPC78609
0.749 Intermediate Similarity NPC292958
0.749 Intermediate Similarity NPC74360
0.748 Intermediate Similarity NPC137353
0.7479 Intermediate Similarity NPC304926
0.7479 Intermediate Similarity NPC476041
0.7479 Intermediate Similarity NPC21638
0.7478 Intermediate Similarity NPC326422
0.7469 Intermediate Similarity NPC144452
0.7462 Intermediate Similarity NPC132385
0.746 Intermediate Similarity NPC184680
0.7459 Intermediate Similarity NPC471762
0.7458 Intermediate Similarity NPC132642
0.7458 Intermediate Similarity NPC472099
0.7449 Intermediate Similarity NPC97902
0.7448 Intermediate Similarity NPC184408
0.7447 Intermediate Similarity NPC5145
0.7437 Intermediate Similarity NPC152768
0.7437 Intermediate Similarity NPC148183
0.743 Intermediate Similarity NPC470785
0.7426 Intermediate Similarity NPC234078
0.7426 Intermediate Similarity NPC221100
0.7418 Intermediate Similarity NPC473185
0.7412 Intermediate Similarity NPC473800
0.741 Intermediate Similarity NPC72905
0.7398 Intermediate Similarity NPC477112
0.7398 Intermediate Similarity NPC474688
0.7398 Intermediate Similarity NPC267853
0.7391 Intermediate Similarity NPC476167
0.739 Intermediate Similarity NPC470022
0.7384 Intermediate Similarity NPC110182
0.7384 Intermediate Similarity NPC472098
0.7375 Intermediate Similarity NPC264285
0.7375 Intermediate Similarity NPC303658
0.7373 Intermediate Similarity NPC471304
0.7373 Intermediate Similarity NPC199667
0.7373 Intermediate Similarity NPC470020
0.7371 Intermediate Similarity NPC477066
0.7368 Intermediate Similarity NPC279189
0.7368 Intermediate Similarity NPC200553
0.7368 Intermediate Similarity NPC244897
0.7364 Intermediate Similarity NPC170114
0.7362 Intermediate Similarity NPC471891
0.7362 Intermediate Similarity NPC82548
0.736 Intermediate Similarity NPC470784
0.7357 Intermediate Similarity NPC315499
0.7349 Intermediate Similarity NPC295228
0.7349 Intermediate Similarity NPC470017
0.7348 Intermediate Similarity NPC192315
0.7347 Intermediate Similarity NPC110151
0.7344 Intermediate Similarity NPC473188
0.7342 Intermediate Similarity NPC146418
0.7342 Intermediate Similarity NPC208284
0.7342 Intermediate Similarity NPC82370
0.7341 Intermediate Similarity NPC478082
0.7341 Intermediate Similarity NPC478081
0.7341 Intermediate Similarity NPC477067
0.7339 Intermediate Similarity NPC180504
0.7336 Intermediate Similarity NPC63109
0.7336 Intermediate Similarity NPC179287
0.7333 Intermediate Similarity NPC312645
0.7331 Intermediate Similarity NPC473181
0.7331 Intermediate Similarity NPC477861
0.7328 Intermediate Similarity NPC476451
0.7328 Intermediate Similarity NPC475253
0.7325 Intermediate Similarity NPC84853
0.7322 Intermediate Similarity NPC470549
0.7319 Intermediate Similarity NPC321428
0.7317 Intermediate Similarity NPC66777
0.7317 Intermediate Similarity NPC274640
0.7316 Intermediate Similarity NPC74413
0.7316 Intermediate Similarity NPC187558
0.7311 Intermediate Similarity NPC473180
0.7309 Intermediate Similarity NPC316411
0.7308 Intermediate Similarity NPC470500
0.7303 Intermediate Similarity NPC96321
0.7296 Intermediate Similarity NPC260900
0.7294 Intermediate Similarity NPC17437
0.7283 Intermediate Similarity NPC81939
0.728 Intermediate Similarity NPC236668
0.728 Intermediate Similarity NPC473187
0.728 Intermediate Similarity NPC162002
0.728 Intermediate Similarity NPC89508
0.7277 Intermediate Similarity NPC300156
0.7277 Intermediate Similarity NPC45190
0.7277 Intermediate Similarity NPC472064
0.7276 Intermediate Similarity NPC192712
0.7273 Intermediate Similarity NPC171393
0.7273 Intermediate Similarity NPC295452
0.7273 Intermediate Similarity NPC473179
0.7265 Intermediate Similarity NPC223427
0.7258 Intermediate Similarity NPC315062
0.7257 Intermediate Similarity NPC174672
0.7257 Intermediate Similarity NPC174758
0.7256 Intermediate Similarity NPC473639
0.7255 Intermediate Similarity NPC475666
0.7254 Intermediate Similarity NPC16352
0.725 Intermediate Similarity NPC237740
0.725 Intermediate Similarity NPC146976
0.7246 Intermediate Similarity NPC193238
0.7241 Intermediate Similarity NPC81535
0.724 Intermediate Similarity NPC174489
0.7238 Intermediate Similarity NPC264176
0.7234 Intermediate Similarity NPC475070
0.7234 Intermediate Similarity NPC472259
0.7231 Intermediate Similarity NPC469594
0.7218 Intermediate Similarity NPC326363
0.7218 Intermediate Similarity NPC24019
0.7216 Intermediate Similarity NPC472434
0.7214 Intermediate Similarity NPC207620
0.7209 Intermediate Similarity NPC67401
0.7208 Intermediate Similarity NPC469592
0.7208 Intermediate Similarity NPC227824
0.7208 Intermediate Similarity NPC471080
0.7202 Intermediate Similarity NPC269270

  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 NPC53534 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
0.8536 High Similarity NPD5482 Discontinued
0.8523 High Similarity NPD5483 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.8305 Intermediate Similarity NPD3006 Discontinued
0.8289 Intermediate Similarity NPD4429 Discontinued
0.827 Intermediate Similarity NPD4958 Clinical (unspecified phase)
0.8127 Intermediate Similarity NPD5450 Discontinued
0.7941 Intermediate Similarity NPD5022 Discontinued
0.7895 Intermediate Similarity NPD4558 Phase 2
0.7842 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.783 Intermediate Similarity NPD6242 Discontinued
0.7718 Intermediate Similarity NPD5479 Discontinued
0.7698 Intermediate Similarity NPD2311 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD7603 Discontinued
0.7615 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7577 Intermediate Similarity NPD7924 Phase 2
0.7577 Intermediate Similarity NPD7925 Phase 2
0.7564 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7549 Intermediate Similarity NPD6531 Approved
0.7549 Intermediate Similarity NPD6530 Approved
0.7544 Intermediate Similarity NPD8279 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD7690 Clinical (unspecified phase)
0.7511 Intermediate Similarity NPD3389 Approved
0.7511 Intermediate Similarity NPD3393 Approved
0.7511 Intermediate Similarity NPD3394 Approved
0.751 Intermediate Similarity NPD4885 Approved
0.751 Intermediate Similarity NPD7393 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6961 Discontinued
0.7479 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD6790 Phase 1
0.7436 Intermediate Similarity NPD2510 Approved
0.7436 Intermediate Similarity NPD2509 Approved
0.7414 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD4442 Phase 2
0.7379 Intermediate Similarity NPD2951 Discontinued
0.7373 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD4368 Phase 2
0.7294 Intermediate Similarity NPD8358 Approved
0.7287 Intermediate Similarity NPD1659 Phase 1
0.7287 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7269 Intermediate Similarity NPD8091 Phase 3
0.7269 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD5559 Phase 2
0.7244 Intermediate Similarity NPD4440 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD5632 Approved
0.7218 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD7853 Phase 2
0.7206 Intermediate Similarity NPD7994 Phase 2
0.7201 Intermediate Similarity NPD5018 Phase 3
0.72 Intermediate Similarity NPD7558 Phase 2
0.7197 Intermediate Similarity NPD6456 Discontinued
0.7197 Intermediate Similarity NPD5416 Discontinued
0.7194 Intermediate Similarity NPD1927 Discontinued
0.7188 Intermediate Similarity NPD8100 Phase 3
0.7184 Intermediate Similarity NPD1856 Discontinued
0.7178 Intermediate Similarity NPD5293 Phase 2
0.7178 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD1038 Approved
0.7174 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD7803 Approved
0.7169 Intermediate Similarity NPD6231 Phase 3
0.7165 Intermediate Similarity NPD8049 Phase 2
0.7161 Intermediate Similarity NPD4795 Phase 2
0.7149 Intermediate Similarity NPD4952 Phase 3
0.7149 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.7148 Intermediate Similarity NPD8349 Phase 1
0.7148 Intermediate Similarity NPD6228 Discontinued
0.7148 Intermediate Similarity NPD7708 Approved
0.7143 Intermediate Similarity NPD5658 Approved
0.7137 Intermediate Similarity NPD3945 Discontinued
0.7132 Intermediate Similarity NPD6172 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD7956 Approved
0.711 Intermediate Similarity NPD7955 Approved
0.7105 Intermediate Similarity NPD3343 Phase 3
0.7104 Intermediate Similarity NPD8101 Phase 3
0.7102 Intermediate Similarity NPD1996 Discontinued
0.7097 Intermediate Similarity NPD7426 Phase 1
0.7092 Intermediate Similarity NPD3746 Discontinued
0.7088 Intermediate Similarity NPD1480 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5116 Phase 1
0.7071 Intermediate Similarity NPD7665 Phase 2
0.7071 Intermediate Similarity NPD7666 Phase 3
0.7068 Intermediate Similarity NPD3259 Approved
0.7064 Intermediate Similarity NPD1740 Approved
0.7064 Intermediate Similarity NPD1739 Approved
0.7063 Intermediate Similarity NPD4373 Phase 2
0.7063 Intermediate Similarity NPD5459 Phase 2
0.7063 Intermediate Similarity NPD6223 Clinical (unspecified phase)
0.7061 Intermediate Similarity NPD7404 Approved
0.7059 Intermediate Similarity NPD7198 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD6247 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD5850 Phase 3
0.7028 Intermediate Similarity NPD8289 Discontinued
0.7028 Intermediate Similarity NPD5640 Discontinued
0.7028 Intermediate Similarity NPD3263 Phase 3
0.7023 Intermediate Similarity NPD8463 Approved
0.7021 Intermediate Similarity NPD3825 Phase 3
0.702 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6568 Discontinued
0.7019 Intermediate Similarity NPD5867 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD4039 Approved
0.7017 Intermediate Similarity NPD4033 Approved
0.7017 Intermediate Similarity NPD4122 Approved
0.7017 Intermediate Similarity NPD4035 Approved
0.7017 Intermediate Similarity NPD4037 Approved
0.7017 Intermediate Similarity NPD4034 Approved
0.7017 Intermediate Similarity NPD4038 Approved
0.7017 Intermediate Similarity NPD32 Approved
0.7017 Intermediate Similarity NPD4036 Approved
0.7017 Intermediate Similarity NPD31 Approved
0.7008 Intermediate Similarity NPD5612 Discontinued
0.7 Intermediate Similarity NPD4845 Discontinued
0.6996 Remote Similarity NPD8247 Approved
0.6996 Remote Similarity NPD8246 Approved
0.6992 Remote Similarity NPD3402 Phase 1
0.6988 Remote Similarity NPD5488 Discontinued
0.6987 Remote Similarity NPD7001 Phase 3
0.6985 Remote Similarity NPD3811 Discontinued
0.6983 Remote Similarity NPD7470 Discontinued
0.6983 Remote Similarity NPD5475 Discontinued
0.6981 Remote Similarity NPD3801 Clinical (unspecified phase)
0.698 Remote Similarity NPD946 Discontinued
0.6979 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6977 Remote Similarity NPD7067 Approved
0.6977 Remote Similarity NPD7068 Approved
0.6972 Remote Similarity NPD7176 Clinical (unspecified phase)
0.6969 Remote Similarity NPD6963 Approved
0.6969 Remote Similarity NPD6964 Approved
0.6949 Remote Similarity NPD4118 Clinical (unspecified phase)
0.6948 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6944 Remote Similarity NPD6968 Phase 2
0.6944 Remote Similarity NPD5924 Discontinued
0.6944 Remote Similarity NPD6969 Phase 2
0.6941 Remote Similarity NPD5891 Approved
0.6939 Remote Similarity NPD2412 Clinical (unspecified phase)
0.6938 Remote Similarity NPD6716 Phase 1
0.6932 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6931 Remote Similarity NPD3781 Phase 2
0.6929 Remote Similarity NPD4850 Phase 1
0.6923 Remote Similarity NPD6770 Approved
0.692 Remote Similarity NPD4501 Approved
0.692 Remote Similarity NPD4500 Approved
0.692 Remote Similarity NPD484 Approved
0.692 Remote Similarity NPD7859 Phase 2
0.692 Remote Similarity NPD7416 Clinical (unspecified phase)
0.6917 Remote Similarity NPD3507 Phase 2
0.6914 Remote Similarity NPD4502 Phase 2
0.6914 Remote Similarity NPD8284 Discontinued
0.6911 Remote Similarity NPD4989 Phase 2
0.6908 Remote Similarity NPD8356 Approved
0.6908 Remote Similarity NPD2285 Clinical (unspecified phase)
0.6908 Remote Similarity NPD3986 Discontinued
0.6894 Remote Similarity NPD3477 Phase 2
0.6894 Remote Similarity NPD3478 Clinical (unspecified phase)
0.6894 Remote Similarity NPD5532 Phase 2
0.689 Remote Similarity NPD6263 Clinical (unspecified phase)
0.6888 Remote Similarity NPD6838 Clinical (unspecified phase)
0.6878 Remote Similarity NPD6999 Discontinued
0.6878 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6878 Remote Similarity NPD4548 Discontinued
0.6877 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5426 Phase 3
0.6875 Remote Similarity NPD3947 Discontinued
0.6865 Remote Similarity NPD6165 Phase 2
0.6865 Remote Similarity NPD8430 Approved
0.6865 Remote Similarity NPD6164 Phase 2
0.6863 Remote Similarity NPD6494 Phase 2
0.686 Remote Similarity NPD2187 Approved
0.686 Remote Similarity NPD7467 Discontinued
0.686 Remote Similarity NPD2189 Approved
0.6855 Remote Similarity NPD7194 Discontinued
0.6851 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6846 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6844 Remote Similarity NPD5066 Phase 2
0.6844 Remote Similarity NPD5067 Phase 2
0.684 Remote Similarity NPD6209 Approved
0.6838 Remote Similarity NPD4372 Phase 1
0.6838 Remote Similarity NPD8364 Approved
0.6838 Remote Similarity NPD6569 Phase 2
0.6838 Remote Similarity NPD8363 Approved
0.6834 Remote Similarity NPD7417 Discontinued
0.6832 Remote Similarity NPD6276 Discontinued
0.6825 Remote Similarity NPD5499 Approved
0.6823 Remote Similarity NPD7181 Phase 3
0.6818 Remote Similarity NPD1392 Approved
0.6818 Remote Similarity NPD7222 Phase 2
0.6816 Remote Similarity NPD3816 Phase 1
0.6816 Remote Similarity NPD3815 Phase 1
0.6815 Remote Similarity NPD7395 Discontinued
0.6815 Remote Similarity NPD3354 Phase 2
0.6813 Remote Similarity NPD7408 Phase 2
0.6809 Remote Similarity NPD4454 Phase 2
0.6806 Remote Similarity NPD4896 Clinical (unspecified phase)
0.6806 Remote Similarity NPD5644 Phase 1
0.6805 Remote Similarity NPD5901 Discontinued
0.6805 Remote Similarity NPD8442 Discontinued
0.6803 Remote Similarity NPD1166 Clinical (unspecified phase)
0.68 Remote Similarity NPD4881 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
A: chemistry similarity;
B: biological targets similarity;
C: networks similarity;
D: cell-based bioactivity similarity;
E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data