Structure

Physi-Chem Properties

Molecular Weight:  564.35
Volume:  600.6
LogP:  3.5
LogD:  2.837
LogS:  -3.628
# Rotatable Bonds:  1
TPSA:  72.46
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  8
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.342
Synthetic Accessibility Score:  6.506
Fsp3:  0.556
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.231
MDCK Permeability:  2.186429628636688e-05
Pgp-inhibitor:  0.972
Pgp-substrate:  0.841
Human Intestinal Absorption (HIA):  0.066
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.796

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.93
Plasma Protein Binding (PPB):  88.76469421386719%
Volume Distribution (VD):  4.662
Pgp-substrate:  10.33343505859375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.058
CYP1A2-substrate:  0.44
CYP2C19-inhibitor:  0.051
CYP2C19-substrate:  0.124
CYP2C9-inhibitor:  0.042
CYP2C9-substrate:  0.072
CYP2D6-inhibitor:  0.985
CYP2D6-substrate:  0.934
CYP3A4-inhibitor:  0.755
CYP3A4-substrate:  0.796

ADMET: Excretion

Clearance (CL):  6.698
Half-life (T1/2):  0.204

ADMET: Toxicity

hERG Blockers:  0.954
Human Hepatotoxicity (H-HT):  0.986
Drug-inuced Liver Injury (DILI):  0.054
AMES Toxicity:  0.122
Rat Oral Acute Toxicity:  0.228
Maximum Recommended Daily Dose:  0.946
Skin Sensitization:  0.931
Carcinogencity:  0.437
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.956

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

  Natural Product: NPC473310

Natural Product ID:  NPC473310
Common Name*:   Manzamine E
IUPAC Name:   n.a.
Synonyms:   Manzamine E
Standard InCHIKey:  LTHULOBARTYAMF-ASQXKTFQSA-N
Standard InCHI:  InChI=1S/C36H44N4O2/c41-26-10-9-20-40-25(13-14-26)22-35-24-39-19-8-4-2-1-3-7-17-36(42,34(35)40)23-29(30(35)16-21-39)32-33-28(15-18-37-32)27-11-5-6-12-31(27)38-33/h1,3,5-6,11-12,15,18,23,25,30,34,38,42H,2,4,7-10,13-14,16-17,19-22,24H2/b3-1-/t25-,30?,34+,35-,36-/m0/s1
SMILES:  C1=CCC[C@@]2(C=C(C3CCN(CCCC1)C[C@]13C[C@@H]3CCC(=O)CCCN3[C@@H]21)c1c2c(ccn1)c1ccccc1[nH]2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL399493
PubChem CID:   44445401
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
NPO32531 sponge sp. Species n.a. n.a. n.a. collected from vertical slopes between 33 and 40 m from Knife Cape, Manado Bay, Indonesia 2011-MAR PMID[12828469]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[15332848]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia n.a. PMID[16872140]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia 2004-Mar PMID[16872140]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. Indonesian n.a. PMID[16872140]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia 2002-May PMID[16872140]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[28452477]
NPO33515 xestospongia ashmorica Species Petrosiidae Eukaryota n.a. Philippine n.a. PMID[8946747]

☑ 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
NPT591 Individual Protein Glycogen synthase kinase-3 beta Homo sapiens Inhibition = 53.6 % PMID[455811]
NPT591 Individual Protein Glycogen synthase kinase-3 beta Homo sapiens IC50 = 25000.0 nM PMID[455811]
NPT1864 Cell Line L5178Y Mus musculus ED50 = 6.6 ug ml-1 PMID[455812]
NPT591 Individual Protein Glycogen synthase kinase-3 beta Homo sapiens Inhibition = 53.6 % PMID[455815]
NPT86 Organism Mycobacterium intracellulare Mycobacterium intracellulare IC50 = 12.5 ug.mL-1 PMID[455810]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 13100.0 nM PMID[455810]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis Inhibition = 0.0 % PMID[455812]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 3.76 ug.mL-1 PMID[455813]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 3.4 ug.mL-1 PMID[455813]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 4.76 ug.mL-1 PMID[455813]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 3.8 ug.mL-1 PMID[455813]
NPT633 Organism Leishmania donovani Leishmania donovani IC90 = 6.8 ug.mL-1 PMID[455813]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 3.4 ug.mL-1 PMID[455814]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 4.76 ug.mL-1 PMID[455814]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 3.8 ug.mL-1 PMID[455814]
NPT86 Organism Mycobacterium intracellulare Mycobacterium intracellulare IC50 = 12.5 ug.mL-1 PMID[455814]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 13100.0 nM PMID[455814]
NPT633 Organism Leishmania donovani Leishmania donovani IC90 = 6.8 ug.mL-1 PMID[455814]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 3.8 ug.mL-1 PMID[455814]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 3.8 ug.mL-1 PMID[455815]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 3.4 ug.mL-1 PMID[455815]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 4.76 ug.mL-1 PMID[455815]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 3.8 ug.mL-1 PMID[455815]
NPT86 Organism Mycobacterium intracellulare Mycobacterium intracellulare IC50 = 12.5 ug.mL-1 PMID[455815]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 = 13.1 ug.mL-1 PMID[455815]
NPT633 Organism Leishmania donovani Leishmania donovani IC90 = 6.8 ug.mL-1 PMID[455815]

☑ 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 NPC473310 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
0.9282 High Similarity NPC473362
0.9282 High Similarity NPC166492
0.9265 High Similarity NPC475338
0.9265 High Similarity NPC909
0.922 High Similarity NPC475258
0.919 High Similarity NPC41679
0.9126 High Similarity NPC476491
0.9055 High Similarity NPC250835
0.8972 High Similarity NPC473312
0.8969 High Similarity NPC265576
0.875 High Similarity NPC475288
0.8702 High Similarity NPC471506
0.8634 High Similarity NPC473757
0.8585 High Similarity NPC6215
0.8551 High Similarity NPC472027
0.8498 Intermediate Similarity NPC476492
0.838 Intermediate Similarity NPC476451
0.8259 Intermediate Similarity NPC232130
0.8106 Intermediate Similarity NPC471564
0.8081 Intermediate Similarity NPC62749
0.808 Intermediate Similarity NPC81175
0.8037 Intermediate Similarity NPC477714
0.8 Intermediate Similarity NPC476493
0.7991 Intermediate Similarity NPC477715
0.7982 Intermediate Similarity NPC471891
0.798 Intermediate Similarity NPC157828
0.798 Intermediate Similarity NPC195239
0.7944 Intermediate Similarity NPC251936
0.7941 Intermediate Similarity NPC11445
0.7933 Intermediate Similarity NPC98715
0.7915 Intermediate Similarity NPC271862
0.7874 Intermediate Similarity NPC252338
0.785 Intermediate Similarity NPC15102
0.7822 Intermediate Similarity NPC321708
0.7822 Intermediate Similarity NPC213629
0.782 Intermediate Similarity NPC46225
0.782 Intermediate Similarity NPC225821
0.7804 Intermediate Similarity NPC151976
0.7804 Intermediate Similarity NPC87856
0.7793 Intermediate Similarity NPC475422
0.7783 Intermediate Similarity NPC258062
0.7783 Intermediate Similarity NPC127677
0.7773 Intermediate Similarity NPC229893
0.7772 Intermediate Similarity NPC17059
0.7767 Intermediate Similarity NPC267965
0.7751 Intermediate Similarity NPC300183
0.7746 Intermediate Similarity NPC162860
0.7742 Intermediate Similarity NPC476041
0.7742 Intermediate Similarity NPC304926
0.7736 Intermediate Similarity NPC54420
0.7729 Intermediate Similarity NPC227582
0.7723 Intermediate Similarity NPC94752
0.77 Intermediate Similarity NPC87755
0.7696 Intermediate Similarity NPC132211
0.7692 Intermediate Similarity NPC131887
0.7692 Intermediate Similarity NPC171317
0.7664 Intermediate Similarity NPC478158
0.7659 Intermediate Similarity NPC117244
0.7659 Intermediate Similarity NPC473763
0.7656 Intermediate Similarity NPC293917
0.7638 Intermediate Similarity NPC59269
0.7634 Intermediate Similarity NPC33949
0.7615 Intermediate Similarity NPC204491
0.7615 Intermediate Similarity NPC203614
0.7604 Intermediate Similarity NPC234078
0.7604 Intermediate Similarity NPC221100
0.76 Intermediate Similarity NPC326363
0.76 Intermediate Similarity NPC477175
0.76 Intermediate Similarity NPC213468
0.76 Intermediate Similarity NPC470730
0.7583 Intermediate Similarity NPC475506
0.7571 Intermediate Similarity NPC100321
0.7569 Intermediate Similarity NPC478157
0.7566 Intermediate Similarity NPC477177
0.7566 Intermediate Similarity NPC475969
0.7566 Intermediate Similarity NPC475859
0.7565 Intermediate Similarity NPC477861
0.7559 Intermediate Similarity NPC475070
0.7559 Intermediate Similarity NPC473376
0.7558 Intermediate Similarity NPC75634
0.7556 Intermediate Similarity NPC191382
0.7556 Intermediate Similarity NPC56109
0.7549 Intermediate Similarity NPC478077
0.7548 Intermediate Similarity NPC133366
0.7547 Intermediate Similarity NPC155143
0.7547 Intermediate Similarity NPC328318
0.7547 Intermediate Similarity NPC260900
0.7547 Intermediate Similarity NPC328596
0.7545 Intermediate Similarity NPC281049
0.7544 Intermediate Similarity NPC325976
0.7537 Intermediate Similarity NPC228835
0.7537 Intermediate Similarity NPC472294
0.7533 Intermediate Similarity NPC165743
0.7524 Intermediate Similarity NPC473640
0.7524 Intermediate Similarity NPC50503
0.7523 Intermediate Similarity NPC2395
0.7523 Intermediate Similarity NPC474896
0.75 Intermediate Similarity NPC280852
0.75 Intermediate Similarity NPC476818
0.7489 Intermediate Similarity NPC155444
0.7489 Intermediate Similarity NPC31097
0.7488 Intermediate Similarity NPC477065
0.7488 Intermediate Similarity NPC48938
0.7476 Intermediate Similarity NPC175474
0.7465 Intermediate Similarity NPC476073
0.7463 Intermediate Similarity NPC235684
0.7462 Intermediate Similarity NPC160105
0.7456 Intermediate Similarity NPC207686
0.7454 Intermediate Similarity NPC314957
0.7453 Intermediate Similarity NPC49196
0.7453 Intermediate Similarity NPC195461
0.7453 Intermediate Similarity NPC79129
0.7453 Intermediate Similarity NPC81654
0.7453 Intermediate Similarity NPC249150
0.7453 Intermediate Similarity NPC313985
0.7452 Intermediate Similarity NPC47190
0.745 Intermediate Similarity NPC203468
0.745 Intermediate Similarity NPC110500
0.745 Intermediate Similarity NPC149155
0.7449 Intermediate Similarity NPC21174
0.7449 Intermediate Similarity NPC271797
0.7443 Intermediate Similarity NPC475602
0.7442 Intermediate Similarity NPC317373
0.7441 Intermediate Similarity NPC52557
0.744 Intermediate Similarity NPC472112
0.7437 Intermediate Similarity NPC6982
0.7431 Intermediate Similarity NPC320968
0.7426 Intermediate Similarity NPC126709
0.7426 Intermediate Similarity NPC283219
0.7426 Intermediate Similarity NPC248041
0.7425 Intermediate Similarity NPC295452
0.7425 Intermediate Similarity NPC171393
0.7424 Intermediate Similarity NPC63751
0.7424 Intermediate Similarity NPC317430
0.7422 Intermediate Similarity NPC141428
0.7419 Intermediate Similarity NPC223791
0.7419 Intermediate Similarity NPC107077
0.7416 Intermediate Similarity NPC474177
0.7416 Intermediate Similarity NPC326422
0.7415 Intermediate Similarity NPC99939
0.7415 Intermediate Similarity NPC308931
0.7413 Intermediate Similarity NPC267885
0.7406 Intermediate Similarity NPC74413
0.74 Intermediate Similarity NPC314603
0.7399 Intermediate Similarity NPC272174
0.7397 Intermediate Similarity NPC31385
0.7397 Intermediate Similarity NPC75726
0.7397 Intermediate Similarity NPC110602
0.7395 Intermediate Similarity NPC327592
0.7389 Intermediate Similarity NPC15840
0.7389 Intermediate Similarity NPC91179
0.7385 Intermediate Similarity NPC126066
0.7385 Intermediate Similarity NPC5145
0.7383 Intermediate Similarity NPC476874
0.7383 Intermediate Similarity NPC193761
0.7376 Intermediate Similarity NPC64436
0.7376 Intermediate Similarity NPC145885
0.7376 Intermediate Similarity NPC14113
0.7376 Intermediate Similarity NPC111275
0.7376 Intermediate Similarity NPC183662
0.7376 Intermediate Similarity NPC84827
0.7376 Intermediate Similarity NPC15573
0.7376 Intermediate Similarity NPC217372
0.7374 Intermediate Similarity NPC49954
0.7374 Intermediate Similarity NPC474561
0.7371 Intermediate Similarity NPC106771
0.7371 Intermediate Similarity NPC205254
0.7371 Intermediate Similarity NPC23420
0.7371 Intermediate Similarity NPC303820
0.7368 Intermediate Similarity NPC477176
0.7368 Intermediate Similarity NPC470729
0.7364 Intermediate Similarity NPC54744
0.7364 Intermediate Similarity NPC317752
0.7364 Intermediate Similarity NPC282247
0.7358 Intermediate Similarity NPC67288
0.7357 Intermediate Similarity NPC57690
0.7356 Intermediate Similarity NPC95783
0.7352 Intermediate Similarity NPC72956
0.7345 Intermediate Similarity NPC235885
0.7342 Intermediate Similarity NPC472285
0.734 Intermediate Similarity NPC55772
0.734 Intermediate Similarity NPC219336
0.734 Intermediate Similarity NPC11126
0.7337 Intermediate Similarity NPC78020
0.7336 Intermediate Similarity NPC94211
0.7336 Intermediate Similarity NPC474877
0.7336 Intermediate Similarity NPC475935
0.7336 Intermediate Similarity NPC52909
0.7325 Intermediate Similarity NPC314954
0.7318 Intermediate Similarity NPC318299
0.7318 Intermediate Similarity NPC6865
0.7318 Intermediate Similarity NPC153980
0.7313 Intermediate Similarity NPC24370
0.7313 Intermediate Similarity NPC319232
0.7313 Intermediate Similarity NPC472123
0.7308 Intermediate Similarity NPC65215
0.7308 Intermediate Similarity NPC173028
0.7308 Intermediate Similarity NPC63199
0.7308 Intermediate Similarity NPC111602
0.7308 Intermediate Similarity NPC102338

  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 NPC473310 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
0.7952 Intermediate Similarity NPD7666 Phase 3
0.7952 Intermediate Similarity NPD7665 Phase 2
0.7887 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.785 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD7824 Approved
0.782 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD7953 Approved
0.7812 Intermediate Similarity NPD7951 Approved
0.7812 Intermediate Similarity NPD7791 Approved
0.7812 Intermediate Similarity NPD7952 Approved
0.7812 Intermediate Similarity NPD7950 Approved
0.7812 Intermediate Similarity NPD7789 Approved
0.7812 Intermediate Similarity NPD7790 Approved
0.781 Intermediate Similarity NPD5426 Phase 3
0.775 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD7730 Approved
0.7748 Intermediate Similarity NPD7731 Approved
0.7658 Intermediate Similarity NPD7271 Approved
0.7656 Intermediate Similarity NPD6999 Discontinued
0.7656 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7653 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD8093 Discontinued
0.7638 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD7619 Phase 3
0.7633 Intermediate Similarity NPD7618 Phase 3
0.7556 Intermediate Similarity NPD7780 Approved
0.7556 Intermediate Similarity NPD7781 Approved
0.7545 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD5065 Approved
0.7537 Intermediate Similarity NPD2096 Phase 2
0.7537 Intermediate Similarity NPD6178 Phase 3
0.7537 Intermediate Similarity NPD2091 Phase 2
0.7512 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7512 Intermediate Similarity NPD4886 Phase 2
0.7512 Intermediate Similarity NPD7470 Discontinued
0.7511 Intermediate Similarity NPD6164 Phase 2
0.7511 Intermediate Similarity NPD6165 Phase 2
0.7488 Intermediate Similarity NPD2094 Phase 2
0.7488 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7488 Intermediate Similarity NPD2095 Phase 2
0.7488 Intermediate Similarity NPD2092 Phase 2
0.7477 Intermediate Similarity NPD7712 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD6595 Phase 3
0.7465 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD4601 Approved
0.7453 Intermediate Similarity NPD4600 Approved
0.745 Intermediate Similarity NPD482 Approved
0.7443 Intermediate Similarity NPD8094 Discontinued
0.7431 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD8431 Approved
0.7395 Intermediate Similarity NPD5901 Discontinued
0.7373 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD8488 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD7957 Phase 1
0.7361 Intermediate Similarity NPD7001 Phase 3
0.7361 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD7415 Suspended
0.7343 Intermediate Similarity NPD3961 Discontinued
0.7327 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD8458 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD6664 Approved
0.7306 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7944 Discontinued
0.7265 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD8406 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD5017 Discontinued
0.7252 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD7603 Discontinued
0.7236 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD7948 Phase 1
0.7228 Intermediate Similarity NPD750 Phase 2
0.7227 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.722 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.722 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD4602 Approved
0.7188 Intermediate Similarity NPD8000 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD7971 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD7970 Approved
0.7162 Intermediate Similarity NPD3330 Phase 1
0.7156 Intermediate Similarity NPD8272 Phase 2
0.7143 Intermediate Similarity NPD3393 Approved
0.7143 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8073 Approved
0.7143 Intermediate Similarity NPD3389 Approved
0.7143 Intermediate Similarity NPD3394 Approved
0.7136 Intermediate Similarity NPD5473 Discontinued
0.7136 Intermediate Similarity NPD2510 Approved
0.7136 Intermediate Similarity NPD2509 Approved
0.713 Intermediate Similarity NPD8248 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD484 Approved
0.713 Intermediate Similarity NPD4500 Approved
0.713 Intermediate Similarity NPD4501 Approved
0.7123 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD3404 Approved
0.7122 Intermediate Similarity NPD4181 Approved
0.7109 Intermediate Similarity NPD4499 Approved
0.7103 Intermediate Similarity NPD6449 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD2837 Discontinued
0.7091 Intermediate Similarity NPD8410 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD8322 Phase 2
0.7087 Intermediate Similarity NPD4076 Approved
0.7087 Intermediate Similarity NPD4079 Approved
0.7087 Intermediate Similarity NPD7711 Discontinued
0.7087 Intermediate Similarity NPD6352 Phase 2
0.7087 Intermediate Similarity NPD8289 Discontinued
0.7085 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD4852 Phase 2
0.7083 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD5003 Discontinued
0.7064 Intermediate Similarity NPD7187 Phase 2
0.7051 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD6976 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD6665 Discontinued
0.7039 Intermediate Similarity NPD3506 Approved
0.7039 Intermediate Similarity NPD3505 Approved
0.7039 Intermediate Similarity NPD2144 Approved
0.7035 Intermediate Similarity NPD5255 Approved
0.7033 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD8072 Approved
0.7021 Intermediate Similarity NPD6970 Phase 2
0.7019 Intermediate Similarity NPD3038 Discontinued
0.7015 Intermediate Similarity NPD3323 Discontinued
0.7014 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD8386 Phase 2
0.7 Intermediate Similarity NPD8114 Approved
0.7 Intermediate Similarity NPD6987 Phase 1
0.7 Intermediate Similarity NPD8115 Approved
0.6995 Remote Similarity NPD6180 Clinical (unspecified phase)
0.6991 Remote Similarity NPD2880 Discontinued
0.699 Remote Similarity NPD4075 Phase 2
0.6987 Remote Similarity NPD6615 Clinical (unspecified phase)
0.6983 Remote Similarity NPD6978 Phase 2
0.6983 Remote Similarity NPD6977 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6964 Remote Similarity NPD4614 Clinical (unspecified phase)
0.6952 Remote Similarity NPD7564 Discontinued
0.6942 Remote Similarity NPD4128 Approved
0.6942 Remote Similarity NPD8358 Approved
0.6933 Remote Similarity NPD7455 Approved
0.6933 Remote Similarity NPD7454 Approved
0.6933 Remote Similarity NPD2411 Approved
0.6927 Remote Similarity NPD5934 Clinical (unspecified phase)
0.6926 Remote Similarity NPD7716 Approved
0.6926 Remote Similarity NPD6850 Phase 2
0.6926 Remote Similarity NPD7717 Approved
0.6926 Remote Similarity NPD6849 Phase 2
0.6923 Remote Similarity NPD7469 Discontinued
0.692 Remote Similarity NPD4051 Discontinued
0.6916 Remote Similarity NPD5592 Clinical (unspecified phase)
0.6912 Remote Similarity NPD4779 Clinical (unspecified phase)
0.6912 Remote Similarity NPD2844 Phase 3
0.6911 Remote Similarity NPD8246 Approved
0.6911 Remote Similarity NPD8247 Approved
0.6904 Remote Similarity NPD2172 Phase 1
0.6903 Remote Similarity NPD7557 Clinical (unspecified phase)
0.6901 Remote Similarity NPD6965 Clinical (unspecified phase)
0.69 Remote Similarity NPD7168 Phase 3
0.6898 Remote Similarity NPD7024 Clinical (unspecified phase)
0.6892 Remote Similarity NPD2008 Discontinued
0.6887 Remote Similarity NPD706 Phase 1
0.6887 Remote Similarity NPD4426 Clinical (unspecified phase)
0.6884 Remote Similarity NPD5505 Discontinued
0.6878 Remote Similarity NPD1326 Approved
0.6878 Remote Similarity NPD1325 Approved
0.6875 Remote Similarity NPD6545 Clinical (unspecified phase)
0.6869 Remote Similarity NPD6281 Approved
0.6867 Remote Similarity NPD6531 Approved
0.6867 Remote Similarity NPD6530 Approved
0.6863 Remote Similarity NPD4554 Clinical (unspecified phase)
0.6861 Remote Similarity NPD3905 Phase 3
0.686 Remote Similarity NPD7921 Approved
0.686 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6857 Remote Similarity NPD7867 Phase 1
0.6854 Remote Similarity NPD8021 Approved
0.6854 Remote Similarity NPD8020 Approved
0.6853 Remote Similarity NPD7202 Clinical (unspecified phase)
0.6849 Remote Similarity NPD6137 Clinical (unspecified phase)
0.6847 Remote Similarity NPD8283 Approved
0.6847 Remote Similarity NPD6288 Clinical (unspecified phase)
0.6847 Remote Similarity NPD56 Approved
0.6847 Remote Similarity NPD8098 Approved
0.6847 Remote Similarity NPD8282 Approved
0.6844 Remote Similarity NPD3014 Clinical (unspecified phase)
0.6844 Remote Similarity NPD3013 Phase 3
0.6842 Remote Similarity NPD7112 Discontinued
0.684 Remote Similarity NPD3082 Discontinued
0.683 Remote Similarity NPD2443 Approved
0.683 Remote Similarity NPD2442 Approved
0.683 Remote Similarity NPD2916 Discontinued
0.6824 Remote Similarity NPD7269 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