Structure

Physi-Chem Properties

Molecular Weight:  432.32
Volume:  459.37
LogP:  5.1
LogD:  4.742
LogS:  -4.844
# Rotatable Bonds:  0
TPSA:  58.92
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.579
Synthetic Accessibility Score:  5.415
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.771
MDCK Permeability:  1.997284016397316e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.772
30% Bioavailability (F30%):  0.651

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.356
Plasma Protein Binding (PPB):  81.58032989501953%
Volume Distribution (VD):  1.651
Pgp-substrate:  6.267909526824951%

ADMET: Metabolism

CYP1A2-inhibitor:  0.034
CYP1A2-substrate:  0.671
CYP2C19-inhibitor:  0.025
CYP2C19-substrate:  0.801
CYP2C9-inhibitor:  0.099
CYP2C9-substrate:  0.02
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.144
CYP3A4-inhibitor:  0.601
CYP3A4-substrate:  0.258

ADMET: Excretion

Clearance (CL):  13.601
Half-life (T1/2):  0.272

ADMET: Toxicity

hERG Blockers:  0.988
Human Hepatotoxicity (H-HT):  0.279
Drug-inuced Liver Injury (DILI):  0.767
AMES Toxicity:  0.045
Rat Oral Acute Toxicity:  0.062
Maximum Recommended Daily Dose:  0.67
Skin Sensitization:  0.973
Carcinogencity:  0.43
Eye Corrosion:  0.945
Eye Irritation:  0.489
Respiratory Toxicity:  0.965

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  Natural Product: NPC296734

Natural Product ID:  NPC296734
Common Name*:   Chlorogenin
IUPAC Name:   n.a.
Synonyms:   Chlorogenin
Standard InCHIKey:  PZNPHSFXILSZTM-JUGSJECZSA-N
Standard InCHI:  InChI=1S/C27H44O4/c1-15-5-10-27(30-14-15)16(2)24-23(31-27)13-20-18-12-22(29)21-11-17(28)6-8-25(21,3)19(18)7-9-26(20,24)4/h15-24,28-29H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21-,22+,23+,24+,25-,26+,27-/m1/s1
SMILES:  C[C@@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5C[C@@H]([C@H]6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O)O)O2)OC1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2047364
PubChem CID:   12303065
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO19920 Yucca gloriosa Species Asparagaceae Eukaryota n.a. stem n.a. DOI[10.1016/0031-9422(89)80212-2]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. bark n.a. PMID[11045899]
NPO21106 Isatis costata Species Brassicaceae Eukaryota n.a. whole plant n.a. PMID[17846565]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. bark n.a. PMID[19555186]
NPO19108 Arthrinium sacchari Species Apiosporaceae Eukaryota n.a. n.a. n.a. PMID[21718054]
NPO22631 Actinopolyspora erythraea Species Actinopolysporaceae Bacteria n.a. mycelium n.a. PMID[21870828]
NPO40931 Solanum macaonense Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[25036668]
NPO21735 Clausena anisum-olens Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[28368606]
NPO21635 Pandalus borealis Species Pandalidae Eukaryota n.a. n.a. n.a. PMID[3349210]
NPO22060 Hippomane mancinella Species Euphorbiaceae Eukaryota Latex n.a. n.a. PMID[6481361]
NPO22060 Hippomane mancinella Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22578 Speranskia tuberculata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19070 Cassia dentata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20952 Dioscorea cirrhosa Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22578 Speranskia tuberculata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22060 Hippomane mancinella Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20952 Dioscorea cirrhosa Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19070 Cassia dentata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19070 Cassia dentata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20032 Prunus sibirica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22453 Befaria racemosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23475 Psoralea acaulis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17819 Ferula transiliensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19108 Arthrinium sacchari Species Apiosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21635 Pandalus borealis Species Pandalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22578 Speranskia tuberculata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22321 Euphorbia lamprocarpa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25227 Senecio roseus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23176 Schefflera bodinieri Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5927 Cortinarius venetus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20358 Streptomyces maritimus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15934 Rhododendron ponticum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19920 Yucca gloriosa Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22119 Echinops bannaticus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22060 Hippomane mancinella Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9972 Angostura granulosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22881 Cryptotermes brevis Species Termitoidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21874 Cercospora melonis Species Mycosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22697 Licaria mahuba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14364 Alisma plantago-aquatica Species Alismataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27833 Xerotus discolor Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7217 Plakobranchus ocellatus Species Placobranchidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17898 Buckiella undulata Species Hypnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19380 Styela plicata Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20506 Batatas edulis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21106 Isatis costata Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21246 Helichrysum anomalum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19693 Lobaria oregana Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17092 Viguiera dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14211 Acinetobacter junii Species Moraxellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO23056 Isaria japonica Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19070 Cassia dentata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22631 Actinopolyspora erythraea Species Actinopolysporaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO23133 Gypsophila patrini Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20677 Fraxinus angustifolia Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12005 Amomum zambesiacum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22246 Aplidium longithorax Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18197 Cadlina luteomarginata Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22187 Ostrea virginica Species Ostreidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20952 Dioscorea cirrhosa Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20182 Euonymus pendulus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22993 Veronica hederifolia Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18568 Artemisia aucheri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22938 Genista hystrix Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21997 Benzoin trilobum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21735 Clausena anisum-olens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23094 Pectinophora gossypiella Species Gelechiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20032 Prunus sibirica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20042 Ambrosia cumanensis Species Asteraceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 50000.0 nM PMID[515272]
NPT2 Others Unspecified IC50 = 6100.0 nM PMID[515273]
NPT2 Others Unspecified IC50 > 10000.0 nM PMID[515273]

☑ 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 NPC296734 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
0.9737 High Similarity NPC257296
0.9737 High Similarity NPC7479
0.9737 High Similarity NPC248944
0.962 High Similarity NPC232044
0.962 High Similarity NPC273290
0.9494 High Similarity NPC227260
0.9487 High Similarity NPC470611
0.9048 High Similarity NPC473542
0.8941 High Similarity NPC149966
0.8941 High Similarity NPC5632
0.8941 High Similarity NPC59006
0.8929 High Similarity NPC228059
0.8916 High Similarity NPC210658
0.8916 High Similarity NPC161928
0.8837 High Similarity NPC167644
0.8837 High Similarity NPC149400
0.8837 High Similarity NPC311246
0.8837 High Similarity NPC144790
0.8837 High Similarity NPC88962
0.881 High Similarity NPC281004
0.881 High Similarity NPC128475
0.8795 High Similarity NPC471240
0.8736 High Similarity NPC174024
0.8736 High Similarity NPC473774
0.8736 High Similarity NPC30687
0.8736 High Similarity NPC253268
0.8736 High Similarity NPC477224
0.8736 High Similarity NPC252253
0.8736 High Similarity NPC473851
0.8736 High Similarity NPC312678
0.8736 High Similarity NPC3538
0.8736 High Similarity NPC179859
0.8736 High Similarity NPC291547
0.8736 High Similarity NPC24960
0.8736 High Similarity NPC131693
0.8736 High Similarity NPC45959
0.8736 High Similarity NPC475436
0.8736 High Similarity NPC113500
0.8736 High Similarity NPC175
0.8706 High Similarity NPC473472
0.8706 High Similarity NPC82955
0.8706 High Similarity NPC102725
0.8706 High Similarity NPC20822
0.8675 High Similarity NPC290612
0.8659 High Similarity NPC470070
0.8636 High Similarity NPC473067
0.8636 High Similarity NPC473064
0.8636 High Similarity NPC473065
0.8636 High Similarity NPC305808
0.8621 High Similarity NPC234352
0.8621 High Similarity NPC161035
0.8621 High Similarity NPC297348
0.8621 High Similarity NPC48339
0.8621 High Similarity NPC477451
0.8621 High Similarity NPC177834
0.8621 High Similarity NPC477547
0.8621 High Similarity NPC250393
0.8621 High Similarity NPC141769
0.8621 High Similarity NPC249204
0.8621 High Similarity NPC325828
0.8605 High Similarity NPC223143
0.8605 High Similarity NPC65550
0.8605 High Similarity NPC279329
0.8553 High Similarity NPC232925
0.8553 High Similarity NPC251201
0.8553 High Similarity NPC63588
0.8539 High Similarity NPC304011
0.8539 High Similarity NPC139271
0.8539 High Similarity NPC142264
0.8539 High Similarity NPC156377
0.8539 High Similarity NPC476510
0.8539 High Similarity NPC121453
0.8523 High Similarity NPC471464
0.8523 High Similarity NPC222731
0.8523 High Similarity NPC217205
0.8523 High Similarity NPC264101
0.8523 High Similarity NPC294686
0.8523 High Similarity NPC291203
0.8506 High Similarity NPC307167
0.8506 High Similarity NPC473830
0.8506 High Similarity NPC204881
0.8506 High Similarity NPC36372
0.8506 High Similarity NPC229801
0.8506 High Similarity NPC476668
0.8506 High Similarity NPC473637
0.8506 High Similarity NPC293609
0.8506 High Similarity NPC210759
0.8471 Intermediate Similarity NPC140446
0.8471 Intermediate Similarity NPC43912
0.8444 Intermediate Similarity NPC475207
0.8444 Intermediate Similarity NPC477222
0.8444 Intermediate Similarity NPC476112
0.8444 Intermediate Similarity NPC233649
0.8444 Intermediate Similarity NPC477223
0.8444 Intermediate Similarity NPC307534
0.8444 Intermediate Similarity NPC470028
0.8442 Intermediate Similarity NPC157422
0.8442 Intermediate Similarity NPC187471
0.8442 Intermediate Similarity NPC470071
0.8442 Intermediate Similarity NPC1340
0.8442 Intermediate Similarity NPC100586
0.8442 Intermediate Similarity NPC109457
0.8442 Intermediate Similarity NPC252182
0.8427 Intermediate Similarity NPC6295
0.8427 Intermediate Similarity NPC19400
0.8427 Intermediate Similarity NPC473610
0.8427 Intermediate Similarity NPC211354
0.8427 Intermediate Similarity NPC475351
0.8427 Intermediate Similarity NPC206003
0.8427 Intermediate Similarity NPC107188
0.8427 Intermediate Similarity NPC474399
0.8427 Intermediate Similarity NPC107962
0.8427 Intermediate Similarity NPC473727
0.8421 Intermediate Similarity NPC477820
0.8409 Intermediate Similarity NPC211845
0.8409 Intermediate Similarity NPC256104
0.8409 Intermediate Similarity NPC182740
0.8409 Intermediate Similarity NPC473726
0.8409 Intermediate Similarity NPC122083
0.8409 Intermediate Similarity NPC172838
0.8409 Intermediate Similarity NPC277774
0.8409 Intermediate Similarity NPC137004
0.8409 Intermediate Similarity NPC476669
0.8395 Intermediate Similarity NPC476176
0.8375 Intermediate Similarity NPC474574
0.8375 Intermediate Similarity NPC64081
0.8375 Intermediate Similarity NPC476233
0.8352 Intermediate Similarity NPC473518
0.8352 Intermediate Similarity NPC473638
0.8352 Intermediate Similarity NPC473616
0.8333 Intermediate Similarity NPC128572
0.8333 Intermediate Similarity NPC287483
0.8333 Intermediate Similarity NPC84111
0.8333 Intermediate Similarity NPC195297
0.8333 Intermediate Similarity NPC184617
0.8333 Intermediate Similarity NPC475643
0.8333 Intermediate Similarity NPC98018
0.8333 Intermediate Similarity NPC132080
0.8333 Intermediate Similarity NPC470863
0.8333 Intermediate Similarity NPC116756
0.8333 Intermediate Similarity NPC103616
0.8333 Intermediate Similarity NPC473601
0.8333 Intermediate Similarity NPC470866
0.8333 Intermediate Similarity NPC470865
0.8333 Intermediate Similarity NPC97700
0.8333 Intermediate Similarity NPC30856
0.8333 Intermediate Similarity NPC475625
0.8333 Intermediate Similarity NPC470610
0.8333 Intermediate Similarity NPC160426
0.8333 Intermediate Similarity NPC470864
0.8333 Intermediate Similarity NPC232037
0.8333 Intermediate Similarity NPC284104
0.8315 Intermediate Similarity NPC475325
0.8315 Intermediate Similarity NPC309866
0.8315 Intermediate Similarity NPC305418
0.8315 Intermediate Similarity NPC473503
0.8313 Intermediate Similarity NPC475388
0.8312 Intermediate Similarity NPC282454
0.8276 Intermediate Similarity NPC131466
0.8272 Intermediate Similarity NPC471045
0.8261 Intermediate Similarity NPC470030
0.8256 Intermediate Similarity NPC472396
0.8242 Intermediate Similarity NPC51520
0.8242 Intermediate Similarity NPC470862
0.8242 Intermediate Similarity NPC83137
0.8242 Intermediate Similarity NPC470861
0.8242 Intermediate Similarity NPC274200
0.8242 Intermediate Similarity NPC232611
0.8242 Intermediate Similarity NPC303069
0.8242 Intermediate Similarity NPC115165
0.8228 Intermediate Similarity NPC304499
0.8228 Intermediate Similarity NPC48795
0.8228 Intermediate Similarity NPC477508
0.8222 Intermediate Similarity NPC21897
0.8222 Intermediate Similarity NPC469710
0.8222 Intermediate Similarity NPC92196
0.8214 Intermediate Similarity NPC474346
0.8214 Intermediate Similarity NPC475820
0.8214 Intermediate Similarity NPC474284
0.8214 Intermediate Similarity NPC474253
0.8214 Intermediate Similarity NPC213737
0.8205 Intermediate Similarity NPC127094
0.8193 Intermediate Similarity NPC73515
0.8182 Intermediate Similarity NPC66407
0.8172 Intermediate Similarity NPC476512
0.8172 Intermediate Similarity NPC472081
0.8172 Intermediate Similarity NPC475574
0.8172 Intermediate Similarity NPC108227
0.8172 Intermediate Similarity NPC477225
0.8171 Intermediate Similarity NPC477282
0.8171 Intermediate Similarity NPC81074
0.8152 Intermediate Similarity NPC291548
0.8148 Intermediate Similarity NPC133596
0.8148 Intermediate Similarity NPC11907
0.8132 Intermediate Similarity NPC238796
0.8132 Intermediate Similarity NPC296936
0.8132 Intermediate Similarity NPC203434
0.8132 Intermediate Similarity NPC473287
0.8132 Intermediate Similarity NPC476728
0.8132 Intermediate Similarity NPC237071

  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 NPC296734 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
0.9737 High Similarity NPD6928 Phase 2
0.8621 High Similarity NPD8171 Discontinued
0.8222 Intermediate Similarity NPD7991 Discontinued
0.7732 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD6115 Approved
0.7412 Intermediate Similarity NPD6118 Approved
0.7412 Intermediate Similarity NPD6114 Approved
0.7412 Intermediate Similarity NPD6697 Approved
0.7407 Intermediate Similarity NPD4787 Phase 1
0.7294 Intermediate Similarity NPD6116 Phase 1
0.7176 Intermediate Similarity NPD6117 Approved
0.6941 Remote Similarity NPD1811 Approved
0.6941 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6941 Remote Similarity NPD1810 Approved
0.6905 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6881 Remote Similarity NPD7327 Approved
0.6881 Remote Similarity NPD7328 Approved
0.686 Remote Similarity NPD3703 Phase 2
0.6854 Remote Similarity NPD7525 Registered
0.6818 Remote Similarity NPD7516 Approved
0.6786 Remote Similarity NPD4244 Approved
0.6786 Remote Similarity NPD4245 Approved
0.6757 Remote Similarity NPD8377 Approved
0.6757 Remote Similarity NPD8294 Approved
0.6696 Remote Similarity NPD8033 Approved
0.6696 Remote Similarity NPD8380 Approved
0.6696 Remote Similarity NPD8296 Approved
0.6696 Remote Similarity NPD8379 Approved
0.6696 Remote Similarity NPD8335 Approved
0.6696 Remote Similarity NPD8378 Approved
0.6667 Remote Similarity NPD3702 Approved
0.6667 Remote Similarity NPD3698 Phase 2
0.6667 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6598 Remote Similarity NPD8035 Phase 2
0.6598 Remote Similarity NPD8034 Phase 2
0.6588 Remote Similarity NPD2254 Approved
0.6588 Remote Similarity NPD2686 Approved
0.6588 Remote Similarity NPD2687 Approved
0.6571 Remote Similarity NPD6412 Phase 2
0.6535 Remote Similarity NPD7638 Approved
0.6514 Remote Similarity NPD8133 Approved
0.6512 Remote Similarity NPD5777 Approved
0.6489 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7639 Approved
0.6471 Remote Similarity NPD7640 Approved
0.6466 Remote Similarity NPD7507 Approved
0.646 Remote Similarity NPD6059 Approved
0.646 Remote Similarity NPD6054 Approved
0.6396 Remote Similarity NPD6940 Discontinued
0.6395 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6395 Remote Similarity NPD4789 Approved
0.6356 Remote Similarity NPD7736 Approved
0.6355 Remote Similarity NPD8174 Phase 2
0.6353 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6353 Remote Similarity NPD5360 Phase 3
0.6348 Remote Similarity NPD6370 Approved
0.6346 Remote Similarity NPD7632 Discontinued
0.6327 Remote Similarity NPD6701 Clinical (unspecified phase)
0.6327 Remote Similarity NPD6700 Approved
0.6303 Remote Similarity NPD7319 Approved
0.6277 Remote Similarity NPD3669 Approved
0.6277 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6265 Remote Similarity NPD371 Approved
0.6263 Remote Similarity NPD6703 Approved
0.6263 Remote Similarity NPD6702 Approved
0.6261 Remote Similarity NPD6016 Approved
0.6261 Remote Similarity NPD6015 Approved
0.6261 Remote Similarity NPD7503 Approved
0.625 Remote Similarity NPD8308 Discontinued
0.6239 Remote Similarity NPD7492 Approved
0.6222 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6207 Remote Similarity NPD5988 Approved
0.6196 Remote Similarity NPD7645 Phase 2
0.619 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6186 Remote Similarity NPD6616 Approved
0.6154 Remote Similarity NPD6067 Discontinued
0.6147 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6136 Remote Similarity NPD6081 Approved
0.6134 Remote Similarity NPD8293 Discontinued
0.6134 Remote Similarity NPD7078 Approved
0.6129 Remote Similarity NPD4748 Discontinued
0.6126 Remote Similarity NPD6882 Approved
0.6111 Remote Similarity NPD6942 Approved
0.6111 Remote Similarity NPD7339 Approved
0.6095 Remote Similarity NPD1700 Approved
0.6087 Remote Similarity NPD3671 Phase 1
0.6083 Remote Similarity NPD6033 Approved
0.6055 Remote Similarity NPD7320 Approved
0.6053 Remote Similarity NPD6009 Approved
0.6042 Remote Similarity NPD7338 Clinical (unspecified phase)
0.602 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6008 Approved
0.6019 Remote Similarity NPD5739 Approved
0.6019 Remote Similarity NPD6675 Approved
0.6019 Remote Similarity NPD7128 Approved
0.6019 Remote Similarity NPD6402 Approved
0.6 Remote Similarity NPD8418 Phase 2
0.5977 Remote Similarity NPD6705 Phase 1
0.5963 Remote Similarity NPD7646 Clinical (unspecified phase)
0.5955 Remote Similarity NPD4758 Discontinued
0.5938 Remote Similarity NPD4788 Approved
0.5938 Remote Similarity NPD6695 Phase 3
0.593 Remote Similarity NPD4224 Phase 2
0.5914 Remote Similarity NPD4238 Approved
0.5914 Remote Similarity NPD5364 Discontinued
0.5914 Remote Similarity NPD4802 Phase 2
0.5913 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5909 Remote Similarity NPD6881 Approved
0.5909 Remote Similarity NPD6899 Approved
0.5887 Remote Similarity NPD8449 Approved
0.5882 Remote Similarity NPD4202 Approved
0.5882 Remote Similarity NPD6399 Phase 3
0.5856 Remote Similarity NPD6372 Approved
0.5856 Remote Similarity NPD6373 Approved
0.584 Remote Similarity NPD8450 Suspended
0.5826 Remote Similarity NPD7755 Approved
0.5826 Remote Similarity NPD7754 Approved
0.5818 Remote Similarity NPD5697 Approved
0.5818 Remote Similarity NPD5701 Approved
0.581 Remote Similarity NPD4755 Approved
0.5804 Remote Similarity NPD7290 Approved
0.5804 Remote Similarity NPD7102 Approved
0.5804 Remote Similarity NPD6883 Approved
0.5789 Remote Similarity NPD4632 Approved
0.5778 Remote Similarity NPD4243 Approved
0.5766 Remote Similarity NPD6011 Approved
0.5752 Remote Similarity NPD6617 Approved
0.5752 Remote Similarity NPD6650 Approved
0.5752 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5752 Remote Similarity NPD6869 Approved
0.5752 Remote Similarity NPD8130 Phase 1
0.5752 Remote Similarity NPD6649 Approved
0.5752 Remote Similarity NPD6847 Approved
0.5743 Remote Similarity NPD5328 Approved
0.5729 Remote Similarity NPD1780 Approved
0.5729 Remote Similarity NPD1779 Approved
0.5727 Remote Similarity NPD6920 Discontinued
0.5714 Remote Similarity NPD6014 Approved
0.5714 Remote Similarity NPD6012 Approved
0.5714 Remote Similarity NPD4786 Approved
0.5714 Remote Similarity NPD6013 Approved
0.5702 Remote Similarity NPD8297 Approved
0.5701 Remote Similarity NPD5285 Approved
0.5701 Remote Similarity NPD4700 Approved
0.5701 Remote Similarity NPD5286 Approved
0.5701 Remote Similarity NPD4696 Approved
0.57 Remote Similarity NPD7524 Approved
0.57 Remote Similarity NPD7750 Discontinued
0.5684 Remote Similarity NPD6929 Approved
0.5673 Remote Similarity NPD7748 Approved
0.566 Remote Similarity NPD7920 Phase 3
0.566 Remote Similarity NPD7919 Phase 3
0.566 Remote Similarity NPD6084 Phase 2
0.566 Remote Similarity NPD6083 Phase 2
0.566 Remote Similarity NPD7902 Approved
0.5658 Remote Similarity NPD385 Approved
0.5658 Remote Similarity NPD384 Approved
0.5652 Remote Similarity NPD6926 Approved
0.5652 Remote Similarity NPD4785 Approved
0.5652 Remote Similarity NPD4784 Approved
0.5652 Remote Similarity NPD6924 Approved
0.5648 Remote Similarity NPD5223 Approved
0.5644 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5631 Remote Similarity NPD7515 Phase 2
0.5631 Remote Similarity NPD6079 Approved
0.563 Remote Similarity NPD6319 Approved
0.5625 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5625 Remote Similarity NPD6931 Approved
0.5625 Remote Similarity NPD6930 Phase 2
0.5625 Remote Similarity NPD6686 Approved
0.562 Remote Similarity NPD7604 Phase 2
0.562 Remote Similarity NPD8328 Phase 3
0.5619 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5607 Remote Similarity NPD8088 Phase 1
0.56 Remote Similarity NPD3618 Phase 1

  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