Structure

Physi-Chem Properties

Molecular Weight:  152.08
Volume:  165.335
LogP:  1.364
LogD:  1.231
LogS:  -1.344
# Rotatable Bonds:  2
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.678
Synthetic Accessibility Score:  2.24
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.289
MDCK Permeability:  1.5987099686753936e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.159
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.899
30% Bioavailability (F30%):  0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.154
Plasma Protein Binding (PPB):  38.77593231201172%
Volume Distribution (VD):  2.322
Pgp-substrate:  56.2577018737793%

ADMET: Metabolism

CYP1A2-inhibitor:  0.3
CYP1A2-substrate:  0.711
CYP2C19-inhibitor:  0.19
CYP2C19-substrate:  0.624
CYP2C9-inhibitor:  0.072
CYP2C9-substrate:  0.899
CYP2D6-inhibitor:  0.071
CYP2D6-substrate:  0.773
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.366

ADMET: Excretion

Clearance (CL):  14.723
Half-life (T1/2):  0.774

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.027
Drug-inuced Liver Injury (DILI):  0.026
AMES Toxicity:  0.06
Rat Oral Acute Toxicity:  0.719
Maximum Recommended Daily Dose:  0.308
Skin Sensitization:  0.613
Carcinogencity:  0.097
Eye Corrosion:  0.033
Eye Irritation:  0.928
Respiratory Toxicity:  0.1

Download Data

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

  Natural Product: NPC313650

Natural Product ID:  NPC313650
Common Name*:   4-(1-Hydroxypropyl)Phenol
IUPAC Name:   4-(1-hydroxypropyl)phenol
Synonyms:  
Standard InCHIKey:  WEKMUBUZJDWJIR-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H12O2/c1-2-9(11)7-3-5-8(10)6-4-7/h3-6,9-11H,2H2,1H3
SMILES:  CCC(C1=CC=C(C=C1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL181890
PubChem CID:   13055557
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0002811] Phenylpropanes

*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
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10606602]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7463094]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8201313]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8699182]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO28841 Fructus aurantii n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6001 Fructus evodiae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6001 Fructus evodiae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO28841 Fructus aurantii n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19584 Pericarpium citri reticulatae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7317 Citrus aurantium 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
NPT32 Organism Mus musculus Mus musculus IC50 > 100000.0 nM PMID[537003]
NPT32 Organism Mus musculus Mus musculus Inhibition = 11.0 % PMID[537003]

☑ 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 NPC313650 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
0.9775 High Similarity NPC325292
0.9775 High Similarity NPC138117
0.9551 High Similarity NPC300478
0.9551 High Similarity NPC300017
0.9326 High Similarity NPC104216
0.9213 High Similarity NPC23167
0.9111 High Similarity NPC25493
0.9111 High Similarity NPC113460
0.9101 High Similarity NPC197783
0.9053 High Similarity NPC132078
0.9053 High Similarity NPC78119
0.9053 High Similarity NPC51333
0.9053 High Similarity NPC128723
0.9053 High Similarity NPC216468
0.9011 High Similarity NPC280347
0.9011 High Similarity NPC123273
0.9011 High Similarity NPC318325
0.9011 High Similarity NPC177420
0.9011 High Similarity NPC242240
0.9011 High Similarity NPC258219
0.8989 High Similarity NPC248817
0.8989 High Similarity NPC175313
0.8958 High Similarity NPC213730
0.8947 High Similarity NPC474073
0.8913 High Similarity NPC55561
0.8878 High Similarity NPC12278
0.8876 High Similarity NPC124436
0.8876 High Similarity NPC265146
0.8866 High Similarity NPC40258
0.8866 High Similarity NPC7686
0.8866 High Similarity NPC91461
0.8854 High Similarity NPC80027
0.8817 High Similarity NPC45040
0.8817 High Similarity NPC304541
0.88 High Similarity NPC251306
0.8791 High Similarity NPC184169
0.8791 High Similarity NPC307235
0.8791 High Similarity NPC407
0.8788 High Similarity NPC233396
0.8788 High Similarity NPC154899
0.8788 High Similarity NPC471350
0.8776 High Similarity NPC305205
0.8763 High Similarity NPC130103
0.8737 High Similarity NPC26244
0.871 High Similarity NPC312304
0.871 High Similarity NPC47950
0.87 High Similarity NPC135464
0.87 High Similarity NPC92623
0.8696 High Similarity NPC27974
0.8681 High Similarity NPC155393
0.8673 High Similarity NPC471578
0.8673 High Similarity NPC101025
0.8673 High Similarity NPC110764
0.866 High Similarity NPC100870
0.8646 High Similarity NPC473388
0.8632 High Similarity NPC128062
0.8632 High Similarity NPC316301
0.8632 High Similarity NPC151715
0.8632 High Similarity NPC27323
0.8627 High Similarity NPC290566
0.8627 High Similarity NPC145638
0.8617 High Similarity NPC204210
0.8617 High Similarity NPC155908
0.8617 High Similarity NPC270547
0.8614 High Similarity NPC305603
0.8614 High Similarity NPC61033
0.8602 High Similarity NPC98772
0.8571 High Similarity NPC174911
0.8571 High Similarity NPC294741
0.8571 High Similarity NPC286904
0.8557 High Similarity NPC260000
0.8544 High Similarity NPC475018
0.8542 High Similarity NPC274678
0.8542 High Similarity NPC8392
0.8542 High Similarity NPC286006
0.8539 High Similarity NPC99394
0.8539 High Similarity NPC103326
0.8539 High Similarity NPC329319
0.8539 High Similarity NPC87299
0.8529 High Similarity NPC317305
0.8526 High Similarity NPC181709
0.8469 Intermediate Similarity NPC280869
0.8469 Intermediate Similarity NPC131587
0.8469 Intermediate Similarity NPC92730
0.8469 Intermediate Similarity NPC171843
0.8447 Intermediate Similarity NPC265211
0.8447 Intermediate Similarity NPC306045
0.8447 Intermediate Similarity NPC473524
0.8427 Intermediate Similarity NPC117180
0.8421 Intermediate Similarity NPC306074
0.8416 Intermediate Similarity NPC8302
0.8404 Intermediate Similarity NPC70436
0.84 Intermediate Similarity NPC62351
0.84 Intermediate Similarity NPC235762
0.84 Intermediate Similarity NPC471228
0.8396 Intermediate Similarity NPC12656
0.8384 Intermediate Similarity NPC166761
0.8381 Intermediate Similarity NPC473521
0.8381 Intermediate Similarity NPC290353
0.8381 Intermediate Similarity NPC153795
0.8381 Intermediate Similarity NPC42911
0.837 Intermediate Similarity NPC150837
0.8367 Intermediate Similarity NPC225464
0.8367 Intermediate Similarity NPC77492
0.8367 Intermediate Similarity NPC107619
0.8367 Intermediate Similarity NPC109955
0.8365 Intermediate Similarity NPC63345
0.8352 Intermediate Similarity NPC304538
0.835 Intermediate Similarity NPC262365
0.8333 Intermediate Similarity NPC306884
0.8333 Intermediate Similarity NPC94139
0.8333 Intermediate Similarity NPC147284
0.8333 Intermediate Similarity NPC55903
0.8333 Intermediate Similarity NPC162314
0.8333 Intermediate Similarity NPC3358
0.8333 Intermediate Similarity NPC210497
0.8318 Intermediate Similarity NPC213
0.8318 Intermediate Similarity NPC10286
0.8317 Intermediate Similarity NPC30506
0.8317 Intermediate Similarity NPC475225
0.8317 Intermediate Similarity NPC108875
0.8317 Intermediate Similarity NPC38079
0.8317 Intermediate Similarity NPC119860
0.8316 Intermediate Similarity NPC192
0.8302 Intermediate Similarity NPC176730
0.8302 Intermediate Similarity NPC123175
0.8283 Intermediate Similarity NPC252821
0.8283 Intermediate Similarity NPC245561
0.8283 Intermediate Similarity NPC122005
0.8269 Intermediate Similarity NPC62258
0.8269 Intermediate Similarity NPC55617
0.8269 Intermediate Similarity NPC326187
0.8265 Intermediate Similarity NPC292730
0.8265 Intermediate Similarity NPC132271
0.8265 Intermediate Similarity NPC216520
0.8265 Intermediate Similarity NPC82664
0.8265 Intermediate Similarity NPC283711
0.8265 Intermediate Similarity NPC202986
0.8247 Intermediate Similarity NPC245187
0.8247 Intermediate Similarity NPC81010
0.8247 Intermediate Similarity NPC32977
0.8247 Intermediate Similarity NPC152415
0.8241 Intermediate Similarity NPC148055
0.8235 Intermediate Similarity NPC470393
0.8235 Intermediate Similarity NPC474839
0.8229 Intermediate Similarity NPC231150
0.8224 Intermediate Similarity NPC157338
0.8224 Intermediate Similarity NPC473137
0.8224 Intermediate Similarity NPC120280
0.8224 Intermediate Similarity NPC235250
0.8218 Intermediate Similarity NPC53051
0.8218 Intermediate Similarity NPC85479
0.8218 Intermediate Similarity NPC24404
0.8218 Intermediate Similarity NPC222522
0.8218 Intermediate Similarity NPC168303
0.8218 Intermediate Similarity NPC302219
0.8218 Intermediate Similarity NPC242342
0.8218 Intermediate Similarity NPC71002
0.8218 Intermediate Similarity NPC304638
0.8218 Intermediate Similarity NPC94351
0.8218 Intermediate Similarity NPC106396
0.8218 Intermediate Similarity NPC196479
0.8218 Intermediate Similarity NPC313030
0.8218 Intermediate Similarity NPC249828
0.8218 Intermediate Similarity NPC146798
0.8208 Intermediate Similarity NPC228425
0.82 Intermediate Similarity NPC52472
0.82 Intermediate Similarity NPC275053
0.82 Intermediate Similarity NPC10588
0.82 Intermediate Similarity NPC253746
0.82 Intermediate Similarity NPC161571
0.82 Intermediate Similarity NPC248573
0.82 Intermediate Similarity NPC225506
0.819 Intermediate Similarity NPC252544
0.819 Intermediate Similarity NPC120982
0.819 Intermediate Similarity NPC79793
0.819 Intermediate Similarity NPC44732
0.819 Intermediate Similarity NPC321252
0.819 Intermediate Similarity NPC174096
0.819 Intermediate Similarity NPC226401
0.819 Intermediate Similarity NPC147634
0.8182 Intermediate Similarity NPC32674
0.8182 Intermediate Similarity NPC152097
0.8182 Intermediate Similarity NPC88420
0.8173 Intermediate Similarity NPC61885
0.8173 Intermediate Similarity NPC63698
0.8173 Intermediate Similarity NPC31274
0.8165 Intermediate Similarity NPC476266
0.8163 Intermediate Similarity NPC144682
0.8163 Intermediate Similarity NPC107522
0.8155 Intermediate Similarity NPC113457
0.8155 Intermediate Similarity NPC248904
0.8144 Intermediate Similarity NPC271440
0.8144 Intermediate Similarity NPC295295
0.8144 Intermediate Similarity NPC29373
0.8137 Intermediate Similarity NPC323810
0.8137 Intermediate Similarity NPC120719
0.8131 Intermediate Similarity NPC264558
0.8131 Intermediate Similarity NPC471485
0.8119 Intermediate Similarity NPC192032

  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 NPC313650 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
0.8876 High Similarity NPD111 Approved
0.883 High Similarity NPD2933 Approved
0.883 High Similarity NPD2934 Approved
0.8737 High Similarity NPD2859 Approved
0.8737 High Similarity NPD2860 Approved
0.8673 High Similarity NPD846 Approved
0.8673 High Similarity NPD940 Approved
0.8632 High Similarity NPD1432 Clinical (unspecified phase)
0.8627 High Similarity NPD9380 Clinical (unspecified phase)
0.8469 Intermediate Similarity NPD3020 Approved
0.82 Intermediate Similarity NPD1242 Phase 1
0.8165 Intermediate Similarity NPD856 Approved
0.8165 Intermediate Similarity NPD318 Approved
0.8165 Intermediate Similarity NPD317 Approved
0.8165 Intermediate Similarity NPD16 Approved
0.8163 Intermediate Similarity NPD1809 Phase 2
0.8163 Intermediate Similarity NPD844 Approved
0.8144 Intermediate Similarity NPD845 Approved
0.8081 Intermediate Similarity NPD288 Approved
0.802 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7978 Intermediate Similarity NPD9294 Approved
0.7961 Intermediate Similarity NPD9608 Approved
0.7961 Intermediate Similarity NPD9610 Approved
0.7946 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.783 Intermediate Similarity NPD2684 Approved
0.7788 Intermediate Similarity NPD9384 Approved
0.7788 Intermediate Similarity NPD9381 Approved
0.7778 Intermediate Similarity NPD228 Approved
0.7768 Intermediate Similarity NPD3091 Approved
0.7757 Intermediate Similarity NPD3021 Approved
0.7757 Intermediate Similarity NPD3022 Approved
0.7739 Intermediate Similarity NPD2561 Approved
0.7739 Intermediate Similarity NPD2562 Approved
0.7736 Intermediate Similarity NPD290 Approved
0.7727 Intermediate Similarity NPD9618 Approved
0.7727 Intermediate Similarity NPD9614 Approved
0.7672 Intermediate Similarity NPD9622 Approved
0.7672 Intermediate Similarity NPD4659 Approved
0.767 Intermediate Similarity NPD3028 Approved
0.7652 Intermediate Similarity NPD3092 Approved
0.7642 Intermediate Similarity NPD968 Approved
0.764 Intermediate Similarity NPD9087 Approved
0.7636 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7615 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD1548 Phase 1
0.7611 Intermediate Similarity NPD9545 Approved
0.7593 Intermediate Similarity NPD4750 Phase 3
0.757 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD9089 Approved
0.7545 Intermediate Similarity NPD821 Approved
0.7545 Intermediate Similarity NPD7843 Approved
0.7542 Intermediate Similarity NPD1133 Approved
0.7542 Intermediate Similarity NPD1134 Approved
0.7542 Intermediate Similarity NPD4103 Phase 2
0.7542 Intermediate Similarity NPD1135 Approved
0.7542 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD1129 Approved
0.7542 Intermediate Similarity NPD1131 Approved
0.7522 Intermediate Similarity NPD9615 Approved
0.7522 Intermediate Similarity NPD9613 Approved
0.7522 Intermediate Similarity NPD9616 Approved
0.75 Intermediate Similarity NPD9088 Approved
0.7479 Intermediate Similarity NPD9619 Approved
0.7479 Intermediate Similarity NPD9620 Approved
0.7479 Intermediate Similarity NPD9621 Approved
0.7477 Intermediate Similarity NPD1444 Approved
0.7477 Intermediate Similarity NPD2228 Approved
0.7477 Intermediate Similarity NPD1445 Approved
0.7477 Intermediate Similarity NPD2234 Approved
0.7477 Intermediate Similarity NPD2229 Approved
0.7476 Intermediate Similarity NPD9273 Approved
0.7456 Intermediate Similarity NPD316 Approved
0.7447 Intermediate Similarity NPD9093 Approved
0.7395 Intermediate Similarity NPD3094 Phase 2
0.7387 Intermediate Similarity NPD9377 Approved
0.7387 Intermediate Similarity NPD9379 Approved
0.7364 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.735 Intermediate Similarity NPD1610 Phase 2
0.7345 Intermediate Similarity NPD7157 Approved
0.7345 Intermediate Similarity NPD256 Approved
0.7345 Intermediate Similarity NPD255 Approved
0.7328 Intermediate Similarity NPD3095 Discontinued
0.7308 Intermediate Similarity NPD9609 Approved
0.7308 Intermediate Similarity NPD9611 Approved
0.7308 Intermediate Similarity NPD9495 Approved
0.7308 Intermediate Similarity NPD9612 Approved
0.7295 Intermediate Similarity NPD3027 Phase 3
0.7273 Intermediate Similarity NPD1792 Phase 2
0.7257 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD1357 Approved
0.7236 Intermediate Similarity NPD601 Approved
0.7236 Intermediate Similarity NPD598 Approved
0.7236 Intermediate Similarity NPD597 Approved
0.7203 Intermediate Similarity NPD422 Phase 1
0.7203 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD9295 Approved
0.7196 Intermediate Similarity NPD9500 Approved
0.7177 Intermediate Similarity NPD1130 Approved
0.7177 Intermediate Similarity NPD1136 Approved
0.7177 Intermediate Similarity NPD1132 Approved
0.7177 Intermediate Similarity NPD829 Discontinued
0.7156 Intermediate Similarity NPD3134 Approved
0.7131 Intermediate Similarity NPD2861 Phase 2
0.713 Intermediate Similarity NPD9568 Approved
0.7119 Intermediate Similarity NPD3421 Phase 3
0.7117 Intermediate Similarity NPD5451 Approved
0.7105 Intermediate Similarity NPD475 Phase 2
0.7103 Intermediate Similarity NPD855 Approved
0.7103 Intermediate Similarity NPD854 Approved
0.71 Intermediate Similarity NPD9094 Approved
0.7091 Intermediate Similarity NPD2342 Discontinued
0.7091 Intermediate Similarity NPD1358 Approved
0.7083 Intermediate Similarity NPD6583 Phase 3
0.7083 Intermediate Similarity NPD3685 Discontinued
0.7083 Intermediate Similarity NPD6582 Phase 2
0.708 Intermediate Similarity NPD7635 Approved
0.7073 Intermediate Similarity NPD4908 Phase 1
0.7059 Intermediate Similarity NPD1091 Approved
0.7049 Intermediate Similarity NPD602 Approved
0.7049 Intermediate Similarity NPD858 Approved
0.7049 Intermediate Similarity NPD599 Approved
0.7049 Intermediate Similarity NPD859 Approved
0.7043 Intermediate Similarity NPD6671 Approved
0.704 Intermediate Similarity NPD6405 Approved
0.704 Intermediate Similarity NPD6407 Approved
0.7037 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD3019 Approved
0.7034 Intermediate Similarity NPD4059 Approved
0.7034 Intermediate Similarity NPD2932 Approved
0.7018 Intermediate Similarity NPD1241 Discontinued
0.7009 Intermediate Similarity NPD5303 Approved
0.7009 Intermediate Similarity NPD5304 Approved
0.7008 Intermediate Similarity NPD2568 Approved
0.7008 Intermediate Similarity NPD3052 Approved
0.7008 Intermediate Similarity NPD3054 Approved
0.6992 Remote Similarity NPD5736 Approved
0.6984 Remote Similarity NPD3059 Approved
0.6984 Remote Similarity NPD3061 Approved
0.6984 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6984 Remote Similarity NPD3062 Approved
0.6984 Remote Similarity NPD1613 Approved
0.6983 Remote Similarity NPD9493 Approved
0.6972 Remote Similarity NPD10 Approved
0.6972 Remote Similarity NPD314 Approved
0.6972 Remote Similarity NPD315 Approved
0.6972 Remote Similarity NPD1237 Approved
0.6972 Remote Similarity NPD310 Approved
0.6972 Remote Similarity NPD311 Approved
0.6972 Remote Similarity NPD309 Approved
0.6967 Remote Similarity NPD4339 Clinical (unspecified phase)
0.696 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6957 Remote Similarity NPD1791 Approved
0.6957 Remote Similarity NPD1793 Approved
0.6953 Remote Similarity NPD3555 Approved
0.6953 Remote Similarity NPD3554 Approved
0.6953 Remote Similarity NPD3553 Approved
0.6953 Remote Similarity NPD3552 Approved
0.6949 Remote Similarity NPD4093 Discontinued
0.6942 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6911 Remote Similarity NPD6584 Phase 3
0.6907 Remote Similarity NPD9250 Approved
0.6893 Remote Similarity NPD9365 Approved
0.6891 Remote Similarity NPD4589 Approved
0.6891 Remote Similarity NPD2286 Discontinued
0.6891 Remote Similarity NPD1751 Approved
0.6891 Remote Similarity NPD4626 Approved
0.6891 Remote Similarity NPD2668 Approved
0.6891 Remote Similarity NPD6516 Phase 2
0.6891 Remote Similarity NPD2667 Approved
0.6891 Remote Similarity NPD5846 Approved
0.688 Remote Similarity NPD3136 Phase 2
0.6875 Remote Similarity NPD823 Approved
0.6875 Remote Similarity NPD74 Approved
0.6875 Remote Similarity NPD9266 Approved
0.6875 Remote Similarity NPD5314 Approved
0.6875 Remote Similarity NPD817 Approved
0.687 Remote Similarity NPD5283 Phase 1
0.6864 Remote Similarity NPD1894 Discontinued
0.686 Remote Similarity NPD2235 Phase 2
0.686 Remote Similarity NPD2231 Phase 2
0.6857 Remote Similarity NPD9296 Approved
0.685 Remote Similarity NPD2238 Phase 2
0.6833 Remote Similarity NPD3847 Discontinued
0.6829 Remote Similarity NPD1818 Approved
0.6829 Remote Similarity NPD1817 Approved
0.6829 Remote Similarity NPD1819 Approved
0.6829 Remote Similarity NPD1820 Approved
0.6807 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6807 Remote Similarity NPD4235 Clinical (unspecified phase)
0.68 Remote Similarity NPD9073 Approved
0.6794 Remote Similarity NPD7266 Discontinued
0.6789 Remote Similarity NPD291 Approved
0.6786 Remote Similarity NPD9267 Approved
0.6786 Remote Similarity NPD9264 Approved
0.6786 Remote Similarity NPD9263 Approved
0.6786 Remote Similarity NPD9532 Phase 3
0.6783 Remote Similarity NPD5535 Approved
0.6777 Remote Similarity NPD1535 Discovery
0.6777 Remote Similarity NPD1201 Approved

  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