Structure

Physi-Chem Properties

Molecular Weight:  241.07
Volume:  243.943
LogP:  3.491
LogD:  3.495
LogS:  -4.163
# Rotatable Bonds:  2
TPSA:  62.32
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.644
Synthetic Accessibility Score:  2.031
Fsp3:  0.071
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.035
MDCK Permeability:  1.4543747965944931e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.35

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.523
Plasma Protein Binding (PPB):  94.58495330810547%
Volume Distribution (VD):  0.589
Pgp-substrate:  4.284355640411377%

ADMET: Metabolism

CYP1A2-inhibitor:  0.991
CYP1A2-substrate:  0.909
CYP2C19-inhibitor:  0.727
CYP2C19-substrate:  0.088
CYP2C9-inhibitor:  0.705
CYP2C9-substrate:  0.871
CYP2D6-inhibitor:  0.824
CYP2D6-substrate:  0.618
CYP3A4-inhibitor:  0.543
CYP3A4-substrate:  0.161

ADMET: Excretion

Clearance (CL):  7.197
Half-life (T1/2):  0.81

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.212
Drug-inuced Liver Injury (DILI):  0.954
AMES Toxicity:  0.06
Rat Oral Acute Toxicity:  0.029
Maximum Recommended Daily Dose:  0.27
Skin Sensitization:  0.69
Carcinogencity:  0.074
Eye Corrosion:  0.007
Eye Irritation:  0.949
Respiratory Toxicity:  0.934

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General Info & Identifiers & Properties  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC118228

Natural Product ID:  NPC118228
Common Name*:   Clausine E
IUPAC Name:   methyl 1-hydroxy-9H-carbazole-3-carboxylate
Synonyms:   Clausine E
Standard InCHIKey:  ZWPODTIRGFOENJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H11NO3/c1-18-14(17)8-6-10-9-4-2-3-5-11(9)15-13(10)12(16)7-8/h2-7,15-16H,1H3
SMILES:  COC(=O)c1cc2c3ccccc3[nH]c2c(c1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL235934
PubChem CID:   5315951
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000210] Carbazoles

*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
NPO29109 Clausena anisata Species Rutaceae Eukaryota n.a. leaf n.a. DOI[10.1080/10412905.1999.9701119]
NPO29109 Clausena anisata Species Rutaceae Eukaryota n.a. seed n.a. DOI[10.1080/10412905.1999.9701119]
NPO29109 Clausena anisata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10650093]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11000023]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO29109 Clausena anisata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19459693]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. root n.a. PMID[21302964]
NPO18135 Clausena vestita Species Rutaceae Eukaryota whole plants Yunnan Province, China 2008-JAN PMID[22093759]
NPO29109 Clausena anisata Species Rutaceae Eukaryota leaf oil n.a. n.a. PMID[22472691]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota Root barks n.a. n.a. PMID[3236015]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29109 Clausena anisata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29109 Clausena anisata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29109 Clausena anisata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18135 Clausena vestita Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19266 Clausena excavata Species Rutaceae 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
NPT83 Cell Line MCF7 Homo sapiens IC50 = 600.0 nM PMID[508359]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 1900.0 nM PMID[508359]
NPT2338 Cell Line SW48 Homo sapiens IC50 = 21000.0 nM PMID[508359]
NPT660 Cell Line SW480 Homo sapiens IC50 = 4800.0 nM PMID[508359]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 60.0 % PMID[508359]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 12.1 % PMID[508359]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 28.0 % PMID[508359]
NPT2338 Cell Line SW48 Homo sapiens Activity = 65.6 % PMID[508359]
NPT2338 Cell Line SW48 Homo sapiens Activity = 12.5 % PMID[508359]
NPT2338 Cell Line SW48 Homo sapiens Activity = 21.9 % PMID[508359]
NPT660 Cell Line SW480 Homo sapiens Activity = 59.9 % PMID[508359]
NPT660 Cell Line SW480 Homo sapiens Activity = 17.5 % PMID[508359]
NPT660 Cell Line SW480 Homo sapiens Activity = 25.7 % PMID[508359]
NPT80 Cell Line Raji Homo sapiens Activity = 60.0 % PMID[508360]
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[508360]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 94590.0 nM PMID[508361]
NPT91 Cell Line KB Homo sapiens IC50 = 107560.0 nM PMID[508361]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 152050.0 nM PMID[508361]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 15800.0 nM PMID[508362]
NPT165 Cell Line HeLa Homo sapiens IC50 = 13300.0 nM PMID[508362]
NPT1125 Cell Line T98G Homo sapiens IC50 = 71600.0 nM PMID[508362]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 37100.0 nM PMID[508362]
NPT65 Cell Line HepG2 Homo sapiens Activity = 55.9 % PMID[508362]
NPT65 Cell Line HepG2 Homo sapiens Activity = 31.1 % PMID[508362]
NPT65 Cell Line HepG2 Homo sapiens Activity = 13.1 % PMID[508362]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 35000.0 nM PMID[508359]
NPT2 Others Unspecified Activity = 27.4 % PMID[508360]
NPT2 Others Unspecified Activity = 42.4 % PMID[508360]
NPT2 Others Unspecified Activity = 74.6 % PMID[508360]
NPT2 Others Unspecified Activity = 100.0 % PMID[508360]
NPT27 Others Unspecified IC50 > 160000.0 nM PMID[508362]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 16900.0 nM PMID[508362]

☑ 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 NPC118228 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
0.9641 High Similarity NPC184408
0.9596 High Similarity NPC51388
0.9436 High Similarity NPC39500
0.9326 High Similarity NPC283117
0.9314 High Similarity NPC474701
0.9235 High Similarity NPC294375
0.9163 High Similarity NPC179287
0.9122 High Similarity NPC274640
0.9082 High Similarity NPC39679
0.9064 High Similarity NPC144452
0.904 High Similarity NPC187501
0.9005 High Similarity NPC293151
0.8883 High Similarity NPC300156
0.885 High Similarity NPC87413
0.8824 High Similarity NPC208084
0.8768 High Similarity NPC3207
0.8762 High Similarity NPC474688
0.8698 High Similarity NPC475844
0.8689 High Similarity NPC225279
0.8684 High Similarity NPC160381
0.865 High Similarity NPC321428
0.865 High Similarity NPC4687
0.86 High Similarity NPC45190
0.8579 High Similarity NPC128823
0.851 High Similarity NPC174760
0.848 Intermediate Similarity NPC9894
0.8418 Intermediate Similarity NPC230403
0.8413 Intermediate Similarity NPC247803
0.8374 Intermediate Similarity NPC249583
0.8357 Intermediate Similarity NPC116238
0.8333 Intermediate Similarity NPC150239
0.8333 Intermediate Similarity NPC210828
0.8333 Intermediate Similarity NPC86834
0.8308 Intermediate Similarity NPC242928
0.8301 Intermediate Similarity NPC23294
0.8295 Intermediate Similarity NPC39370
0.8294 Intermediate Similarity NPC280799
0.8278 Intermediate Similarity NPC169402
0.8252 Intermediate Similarity NPC303951
0.8203 Intermediate Similarity NPC473186
0.8173 Intermediate Similarity NPC310211
0.8173 Intermediate Similarity NPC308137
0.8152 Intermediate Similarity NPC46561
0.81 Intermediate Similarity NPC276517
0.8083 Intermediate Similarity NPC88363
0.8081 Intermediate Similarity NPC144381
0.8054 Intermediate Similarity NPC15801
0.805 Intermediate Similarity NPC475190
0.8049 Intermediate Similarity NPC476098
0.803 Intermediate Similarity NPC280714
0.802 Intermediate Similarity NPC141454
0.802 Intermediate Similarity NPC194040
0.8 Intermediate Similarity NPC474798
0.798 Intermediate Similarity NPC306376
0.7973 Intermediate Similarity NPC6786
0.7962 Intermediate Similarity NPC89508
0.7961 Intermediate Similarity NPC165599
0.7949 Intermediate Similarity NPC478032
0.7944 Intermediate Similarity NPC74360
0.7943 Intermediate Similarity NPC325297
0.7923 Intermediate Similarity NPC132539
0.7902 Intermediate Similarity NPC213308
0.7887 Intermediate Similarity NPC469928
0.787 Intermediate Similarity NPC198503
0.786 Intermediate Similarity NPC473179
0.7857 Intermediate Similarity NPC209769
0.785 Intermediate Similarity NPC312645
0.7847 Intermediate Similarity NPC270918
0.7843 Intermediate Similarity NPC70956
0.7843 Intermediate Similarity NPC243834
0.7824 Intermediate Similarity NPC132642
0.7811 Intermediate Similarity NPC83111
0.7788 Intermediate Similarity NPC134848
0.7778 Intermediate Similarity NPC212535
0.7762 Intermediate Similarity NPC244741
0.7761 Intermediate Similarity NPC246700
0.7748 Intermediate Similarity NPC477112
0.7744 Intermediate Similarity NPC303225
0.7729 Intermediate Similarity NPC315491
0.7729 Intermediate Similarity NPC45459
0.7723 Intermediate Similarity NPC182222
0.7721 Intermediate Similarity NPC330009
0.7717 Intermediate Similarity NPC205372
0.77 Intermediate Similarity NPC94943
0.7696 Intermediate Similarity NPC288987
0.7689 Intermediate Similarity NPC473187
0.7678 Intermediate Similarity NPC193777
0.7673 Intermediate Similarity NPC221873
0.7672 Intermediate Similarity NPC473800
0.7672 Intermediate Similarity NPC473188
0.7664 Intermediate Similarity NPC94157
0.7659 Intermediate Similarity NPC131017
0.7653 Intermediate Similarity NPC309845
0.7653 Intermediate Similarity NPC199667
0.765 Intermediate Similarity NPC96321
0.765 Intermediate Similarity NPC190007
0.7647 Intermediate Similarity NPC470018
0.7614 Intermediate Similarity NPC84347
0.7613 Intermediate Similarity NPC473185
0.7609 Intermediate Similarity NPC208522
0.7606 Intermediate Similarity NPC473181
0.7604 Intermediate Similarity NPC314552
0.7594 Intermediate Similarity NPC88008
0.7586 Intermediate Similarity NPC128751
0.7585 Intermediate Similarity NPC156704
0.7585 Intermediate Similarity NPC153042
0.7583 Intermediate Similarity NPC470930
0.7581 Intermediate Similarity NPC219087
0.7581 Intermediate Similarity NPC473180
0.7581 Intermediate Similarity NPC118940
0.758 Intermediate Similarity NPC276657
0.7571 Intermediate Similarity NPC475112
0.7571 Intermediate Similarity NPC475085
0.7571 Intermediate Similarity NPC291535
0.7569 Intermediate Similarity NPC174576
0.7559 Intermediate Similarity NPC171787
0.7558 Intermediate Similarity NPC74969
0.7554 Intermediate Similarity NPC165964
0.7549 Intermediate Similarity NPC469497
0.7549 Intermediate Similarity NPC106833
0.7513 Intermediate Similarity NPC474409
0.7512 Intermediate Similarity NPC476167
0.75 Intermediate Similarity NPC194740
0.7489 Intermediate Similarity NPC202503
0.7489 Intermediate Similarity NPC473041
0.7488 Intermediate Similarity NPC135887
0.7488 Intermediate Similarity NPC199277
0.7488 Intermediate Similarity NPC471304
0.7478 Intermediate Similarity NPC474192
0.7478 Intermediate Similarity NPC49547
0.7478 Intermediate Similarity NPC475720
0.7478 Intermediate Similarity NPC132329
0.7477 Intermediate Similarity NPC36405
0.7466 Intermediate Similarity NPC60621
0.7465 Intermediate Similarity NPC476106
0.7465 Intermediate Similarity NPC250448
0.7464 Intermediate Similarity NPC192315
0.7455 Intermediate Similarity NPC257851
0.7455 Intermediate Similarity NPC74575
0.7455 Intermediate Similarity NPC478078
0.7454 Intermediate Similarity NPC82370
0.7453 Intermediate Similarity NPC223427
0.7453 Intermediate Similarity NPC317572
0.7448 Intermediate Similarity NPC89549
0.7445 Intermediate Similarity NPC473182
0.7438 Intermediate Similarity NPC42591
0.7434 Intermediate Similarity NPC260434
0.743 Intermediate Similarity NPC183777
0.7426 Intermediate Similarity NPC176127
0.7419 Intermediate Similarity NPC48353
0.7419 Intermediate Similarity NPC12344
0.7416 Intermediate Similarity NPC90229
0.7409 Intermediate Similarity NPC131885
0.7409 Intermediate Similarity NPC303658
0.7399 Intermediate Similarity NPC314633
0.7397 Intermediate Similarity NPC148183
0.7397 Intermediate Similarity NPC152768
0.7385 Intermediate Similarity NPC476287
0.7381 Intermediate Similarity NPC72211
0.738 Intermediate Similarity NPC57453
0.7378 Intermediate Similarity NPC157931
0.7373 Intermediate Similarity NPC220337
0.7371 Intermediate Similarity NPC162484
0.7368 Intermediate Similarity NPC284888
0.7363 Intermediate Similarity NPC72980
0.7359 Intermediate Similarity NPC475816
0.7358 Intermediate Similarity NPC76982
0.7358 Intermediate Similarity NPC116573
0.7352 Intermediate Similarity NPC477979
0.7349 Intermediate Similarity NPC53344
0.7349 Intermediate Similarity NPC193238
0.7348 Intermediate Similarity NPC473183
0.7345 Intermediate Similarity NPC311906
0.7343 Intermediate Similarity NPC138370
0.7342 Intermediate Similarity NPC472099
0.7336 Intermediate Similarity NPC473184
0.7333 Intermediate Similarity NPC24370
0.7333 Intermediate Similarity NPC319232
0.733 Intermediate Similarity NPC264285
0.7328 Intermediate Similarity NPC148889
0.7318 Intermediate Similarity NPC8022
0.7318 Intermediate Similarity NPC322064
0.7318 Intermediate Similarity NPC470799
0.7313 Intermediate Similarity NPC95240
0.7308 Intermediate Similarity NPC160898
0.7306 Intermediate Similarity NPC31700
0.7301 Intermediate Similarity NPC34580
0.7301 Intermediate Similarity NPC118559
0.7301 Intermediate Similarity NPC261251
0.7301 Intermediate Similarity NPC304307
0.7301 Intermediate Similarity NPC124920
0.73 Intermediate Similarity NPC181081
0.73 Intermediate Similarity NPC67401
0.7294 Intermediate Similarity NPC146418
0.729 Intermediate Similarity NPC245816
0.729 Intermediate Similarity NPC476138
0.7286 Intermediate Similarity NPC70259
0.7286 Intermediate Similarity NPC251090
0.7282 Intermediate Similarity NPC322644
0.7277 Intermediate Similarity NPC471944

  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 NPC118228 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
0.8786 High Similarity NPD6160 Clinical (unspecified phase)
0.7955 Intermediate Similarity NPD3746 Discontinued
0.7843 Intermediate Similarity NPD5003 Discontinued
0.7837 Intermediate Similarity NPD5901 Discontinued
0.7729 Intermediate Similarity NPD484 Approved
0.7723 Intermediate Similarity NPD2564 Approved
0.7723 Intermediate Similarity NPD2565 Phase 2
0.7696 Intermediate Similarity NPD3258 Approved
0.7674 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7668 Intermediate Similarity NPD1467 Approved
0.7668 Intermediate Similarity NPD1466 Phase 3
0.765 Intermediate Similarity NPD5632 Approved
0.7609 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7604 Intermediate Similarity NPD5164 Discontinued
0.7593 Intermediate Similarity NPD3257 Approved
0.7554 Intermediate Similarity NPD3986 Discontinued
0.7535 Intermediate Similarity NPD5416 Discontinued
0.7511 Intermediate Similarity NPD1867 Approved
0.75 Intermediate Similarity NPD6242 Discontinued
0.7489 Intermediate Similarity NPD7603 Discontinued
0.7489 Intermediate Similarity NPD7395 Discontinued
0.7489 Intermediate Similarity NPD4429 Discontinued
0.7477 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD2715 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD5512 Phase 3
0.743 Intermediate Similarity NPD5429 Discontinued
0.7418 Intermediate Similarity NPD2721 Clinical (unspecified phase)
0.7406 Intermediate Similarity NPD2779 Approved
0.7389 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD4328 Approved
0.7366 Intermediate Similarity NPD4948 Discontinued
0.736 Intermediate Similarity NPD2844 Phase 3
0.7359 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6456 Discontinued
0.7336 Intermediate Similarity NPD2951 Discontinued
0.7331 Intermediate Similarity NPD5482 Discontinued
0.7327 Intermediate Similarity NPD1166 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD6376 Discontinued
0.7313 Intermediate Similarity NPD5022 Discontinued
0.7306 Intermediate Similarity NPD3243 Approved
0.7304 Intermediate Similarity NPD7853 Phase 2
0.7304 Intermediate Similarity NPD3006 Discontinued
0.729 Intermediate Similarity NPD2920 Discontinued
0.7281 Intermediate Similarity NPD1505 Phase 2
0.7264 Intermediate Similarity NPD2778 Approved
0.7256 Intermediate Similarity NPD6138 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD648 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD7547 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD5479 Discontinued
0.7236 Intermediate Similarity NPD1325 Approved
0.7236 Intermediate Similarity NPD1326 Approved
0.7225 Intermediate Similarity NPD3259 Approved
0.7222 Intermediate Similarity NPD6716 Phase 1
0.7217 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD7470 Discontinued
0.7215 Intermediate Similarity NPD5939 Approved
0.7215 Intermediate Similarity NPD5936 Approved
0.7215 Intermediate Similarity NPD7703 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD4502 Phase 2
0.7202 Intermediate Similarity NPD4506 Discontinued
0.719 Intermediate Similarity NPD1038 Approved
0.7183 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD2175 Phase 3
0.7183 Intermediate Similarity NPD2176 Approved
0.7183 Intermediate Similarity NPD2177 Approved
0.7182 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD8363 Approved
0.7166 Intermediate Similarity NPD8364 Approved
0.7165 Intermediate Similarity NPD3684 Discontinued
0.7163 Intermediate Similarity NPD1534 Approved
0.716 Intermediate Similarity NPD7708 Approved
0.7149 Intermediate Similarity NPD3945 Discontinued
0.7149 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6770 Approved
0.7143 Intermediate Similarity NPD4373 Phase 2
0.7136 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7131 Intermediate Similarity NPD5488 Discontinued
0.713 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD6995 Phase 1
0.7124 Intermediate Similarity NPD5805 Approved
0.7117 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.7116 Intermediate Similarity NPD4511 Phase 1
0.7109 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD3354 Phase 2
0.7097 Intermediate Similarity NPD3947 Discontinued
0.7087 Intermediate Similarity NPD4952 Phase 3
0.7085 Intermediate Similarity NPD5612 Discontinued
0.7078 Intermediate Similarity NPD2916 Discontinued
0.7075 Intermediate Similarity NPD4418 Discontinued
0.7074 Intermediate Similarity NPD4845 Discontinued
0.7064 Intermediate Similarity NPD3003 Approved
0.7061 Intermediate Similarity NPD6247 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7688 Phase 1
0.7056 Intermediate Similarity NPD6962 Phase 2
0.7051 Intermediate Similarity NPD6176 Phase 1
0.7045 Intermediate Similarity NPD7803 Approved
0.7039 Intermediate Similarity NPD3178 Discontinued
0.7033 Intermediate Similarity NPD5399 Discovery
0.7032 Intermediate Similarity NPD6290 Phase 2
0.7031 Intermediate Similarity NPD3263 Phase 3
0.7028 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD5866 Approved
0.7026 Intermediate Similarity NPD4885 Approved
0.7025 Intermediate Similarity NPD8463 Approved
0.7024 Intermediate Similarity NPD5398 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6531 Approved
0.702 Intermediate Similarity NPD6530 Approved
0.7019 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7948 Phase 1
0.7009 Intermediate Similarity NPD4454 Phase 2
0.7 Intermediate Similarity NPD2510 Approved
0.7 Intermediate Similarity NPD2509 Approved
0.7 Intermediate Similarity NPD7994 Phase 2
0.6996 Remote Similarity NPD8467 Approved
0.6996 Remote Similarity NPD8465 Approved
0.6996 Remote Similarity NPD8427 Approved
0.6996 Remote Similarity NPD8429 Approved
0.6996 Remote Similarity NPD8466 Approved
0.6996 Remote Similarity NPD8428 Approved
0.6995 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6991 Remote Similarity NPD4600 Approved
0.6991 Remote Similarity NPD4601 Approved
0.698 Remote Similarity NPD7955 Approved
0.698 Remote Similarity NPD7956 Approved
0.6979 Remote Similarity NPD4368 Phase 2
0.6977 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6976 Remote Similarity NPD6159 Phase 2
0.6976 Remote Similarity NPD5450 Discontinued
0.6974 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6974 Remote Similarity NPD2285 Clinical (unspecified phase)
0.6962 Remote Similarity NPD7417 Discontinued
0.6961 Remote Similarity NPD482 Approved
0.696 Remote Similarity NPD7180 Phase 3
0.696 Remote Similarity NPD5850 Phase 3
0.6958 Remote Similarity NPD8358 Approved
0.6955 Remote Similarity NPD7452 Approved
0.6955 Remote Similarity NPD7222 Phase 2
0.6955 Remote Similarity NPD7453 Approved
0.6944 Remote Similarity NPD8396 Approved
0.6944 Remote Similarity NPD8395 Approved
0.6941 Remote Similarity NPD56 Approved
0.6941 Remote Similarity NPD6987 Phase 1
0.6941 Remote Similarity NPD8282 Approved
0.6941 Remote Similarity NPD8283 Approved
0.6934 Remote Similarity NPD5912 Clinical (unspecified phase)
0.6934 Remote Similarity NPD5913 Phase 3
0.6923 Remote Similarity NPD5658 Approved
0.692 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6916 Remote Similarity NPD4312 Approved
0.6916 Remote Similarity NPD6974 Phase 3
0.6913 Remote Similarity NPD3925 Approved
0.6912 Remote Similarity NPD4501 Approved
0.6912 Remote Similarity NPD4500 Approved
0.6908 Remote Similarity NPD5445 Approved
0.6898 Remote Similarity NPD7946 Pre-registration
0.6889 Remote Similarity NPD3757 Clinical (unspecified phase)
0.6887 Remote Similarity NPD8459 Approved
0.6887 Remote Similarity NPD4499 Approved
0.6887 Remote Similarity NPD8425 Approved
0.6887 Remote Similarity NPD8426 Approved
0.6887 Remote Similarity NPD5928 Phase 1
0.6887 Remote Similarity NPD8460 Approved
0.688 Remote Similarity NPD6263 Clinical (unspecified phase)
0.6875 Remote Similarity NPD8097 Phase 3
0.6875 Remote Similarity NPD8096 Phase 3
0.6872 Remote Similarity NPD8109 Clinical (unspecified phase)
0.6866 Remote Similarity NPD1768 Approved
0.6864 Remote Similarity NPD6323 Clinical (unspecified phase)
0.686 Remote Similarity NPD8102 Discontinued
0.6858 Remote Similarity NPD8160 Phase 2
0.6852 Remote Similarity NPD6162 Approved
0.6852 Remote Similarity NPD6161 Approved
0.6831 Remote Similarity NPD3809 Discontinued
0.682 Remote Similarity NPD6790 Phase 1
0.6818 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6814 Remote Similarity NPD5902 Approved
0.6814 Remote Similarity NPD5903 Approved
0.6814 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6814 Remote Similarity NPD4897 Phase 2
0.6813 Remote Similarity NPD4442 Phase 2
0.6809 Remote Similarity NPD5151 Clinical (unspecified phase)
0.68 Remote Similarity NPD7069 Discontinued
0.6798 Remote Similarity NPD7878 Phase 2
0.6797 Remote Similarity NPD7542 Phase 3
0.6796 Remote Similarity NPD9690 Approved
0.6795 Remote Similarity NPD6199 Discontinued
0.6792 Remote Similarity NPD6517 Phase 3
0.6792 Remote Similarity NPD6141 Clinical (unspecified phase)
0.679 Remote Similarity NPD4558 Phase 2
0.6787 Remote Similarity NPD8098 Approved
0.6784 Remote Similarity NPD3393 Approved
0.6784 Remote Similarity NPD3394 Approved
0.6784 Remote Similarity NPD3389 Approved
0.6778 Remote Similarity NPD4561 Discontinued

  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