Structure

Physi-Chem Properties

Molecular Weight:  216.08
Volume:  226.843
LogP:  3.186
LogD:  3.205
LogS:  -2.749
# Rotatable Bonds:  2
TPSA:  49.69
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.811
Synthetic Accessibility Score:  1.858
Fsp3:  0.077
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:  -4.709
MDCK Permeability:  1.5643676306353882e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.02
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.713
30% Bioavailability (F30%):  0.796

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.117
Plasma Protein Binding (PPB):  96.37877655029297%
Volume Distribution (VD):  0.823
Pgp-substrate:  3.0287249088287354%

ADMET: Metabolism

CYP1A2-inhibitor:  0.986
CYP1A2-substrate:  0.863
CYP2C19-inhibitor:  0.836
CYP2C19-substrate:  0.073
CYP2C9-inhibitor:  0.375
CYP2C9-substrate:  0.949
CYP2D6-inhibitor:  0.955
CYP2D6-substrate:  0.917
CYP3A4-inhibitor:  0.899
CYP3A4-substrate:  0.18

ADMET: Excretion

Clearance (CL):  11.479
Half-life (T1/2):  0.87

ADMET: Toxicity

hERG Blockers:  0.048
Human Hepatotoxicity (H-HT):  0.057
Drug-inuced Liver Injury (DILI):  0.091
AMES Toxicity:  0.114
Rat Oral Acute Toxicity:  0.175
Maximum Recommended Daily Dose:  0.3
Skin Sensitization:  0.931
Carcinogencity:  0.097
Eye Corrosion:  0.401
Eye Irritation:  0.978
Respiratory Toxicity:  0.362

Download Data

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

  Natural Product: NPC50521

Natural Product ID:  NPC50521
Common Name*:   2',3-Dihydroxy-5-Methoxybiphenyl
IUPAC Name:   3-(2-hydroxyphenyl)-5-methoxyphenol
Synonyms:  
Standard InCHIKey:  XBBDTINCHJPZGW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H12O3/c1-16-11-7-9(6-10(14)8-11)12-4-2-3-5-13(12)15/h2-8,14-15H,1H3
SMILES:  COc1cc(O)cc(c1)c1ccccc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1269114
PubChem CID:   49831391
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000325] Biphenols

*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
NPO5061.1 Rhaphiolepis indica var. tashiroi Varieties Rosaceae Eukaryota n.a. root n.a. DOI[10.1021/np100200s]
NPO5061.1 Rhaphiolepis indica var. tashiroi Varieties Rosaceae Eukaryota Roots Wutai, Pingtung County, Taiwan 2007-SEP PMID[20839880]

☑ 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 = 2040.0 nM PMID[465309]

☑ 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 NPC50521 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
1.0 High Similarity NPC244816
1.0 High Similarity NPC221549
0.9817 High Similarity NPC167934
0.9727 High Similarity NPC150624
0.964 High Similarity NPC69261
0.964 High Similarity NPC195466
0.964 High Similarity NPC33270
0.9636 High Similarity NPC808
0.9545 High Similarity NPC276737
0.9545 High Similarity NPC22610
0.9469 High Similarity NPC184302
0.9459 High Similarity NPC53906
0.9381 High Similarity NPC190514
0.9375 High Similarity NPC141090
0.9375 High Similarity NPC203113
0.9358 High Similarity NPC303521
0.9358 High Similarity NPC94045
0.9316 High Similarity NPC228503
0.9316 High Similarity NPC138248
0.9304 High Similarity NPC102639
0.9292 High Similarity NPC15860
0.9292 High Similarity NPC474933
0.9292 High Similarity NPC470759
0.9292 High Similarity NPC219070
0.9292 High Similarity NPC127894
0.9237 High Similarity NPC278955
0.9237 High Similarity NPC105718
0.9224 High Similarity NPC476633
0.9204 High Similarity NPC229147
0.9204 High Similarity NPC54507
0.9204 High Similarity NPC114064
0.9204 High Similarity NPC85292
0.9189 High Similarity NPC280606
0.9182 High Similarity NPC168657
0.916 High Similarity NPC223953
0.916 High Similarity NPC170485
0.9145 High Similarity NPC77789
0.9145 High Similarity NPC18128
0.9115 High Similarity NPC185541
0.9115 High Similarity NPC464
0.9099 High Similarity NPC296920
0.9099 High Similarity NPC90520
0.9083 High Similarity NPC266555
0.9083 High Similarity NPC473221
0.9083 High Similarity NPC53781
0.9076 High Similarity NPC105031
0.9076 High Similarity NPC113495
0.9068 High Similarity NPC84086
0.9043 High Similarity NPC63010
0.9043 High Similarity NPC131118
0.9027 High Similarity NPC228287
0.9027 High Similarity NPC180508
0.9009 High Similarity NPC2682
0.9008 High Similarity NPC215300
0.9008 High Similarity NPC38017
0.9008 High Similarity NPC154866
0.9 High Similarity NPC82299
0.8992 High Similarity NPC206487
0.8992 High Similarity NPC5796
0.8991 High Similarity NPC164576
0.8929 High Similarity NPC255068
0.8926 High Similarity NPC46978
0.8917 High Similarity NPC105925
0.8908 High Similarity NPC121115
0.8898 High Similarity NPC193364
0.8898 High Similarity NPC75713
0.8814 High Similarity NPC100108
0.8814 High Similarity NPC277798
0.8814 High Similarity NPC218753
0.8807 High Similarity NPC102216
0.879 High Similarity NPC282508
0.878 High Similarity NPC190144
0.878 High Similarity NPC471518
0.878 High Similarity NPC16577
0.878 High Similarity NPC471519
0.877 High Similarity NPC74817
0.877 High Similarity NPC236760
0.877 High Similarity NPC246620
0.877 High Similarity NPC82679
0.877 High Similarity NPC124452
0.877 High Similarity NPC324112
0.877 High Similarity NPC293054
0.877 High Similarity NPC169474
0.877 High Similarity NPC236791
0.877 High Similarity NPC282000
0.877 High Similarity NPC159968
0.876 High Similarity NPC234400
0.876 High Similarity NPC60885
0.875 High Similarity NPC282496
0.875 High Similarity NPC95168
0.875 High Similarity NPC233526
0.875 High Similarity NPC474160
0.875 High Similarity NPC136319
0.8739 High Similarity NPC35543
0.8729 High Similarity NPC258979
0.8729 High Similarity NPC8283
0.8729 High Similarity NPC93398
0.872 High Similarity NPC218884
0.8718 High Similarity NPC74821
0.871 High Similarity NPC224157
0.871 High Similarity NPC254000
0.871 High Similarity NPC192687
0.871 High Similarity NPC126836
0.8699 High Similarity NPC266691
0.8699 High Similarity NPC63179
0.8689 High Similarity NPC28730
0.8689 High Similarity NPC50315
0.8689 High Similarity NPC214406
0.8689 High Similarity NPC44748
0.8689 High Similarity NPC230479
0.8689 High Similarity NPC26879
0.8689 High Similarity NPC78974
0.8689 High Similarity NPC223136
0.8689 High Similarity NPC283049
0.8689 High Similarity NPC18924
0.8689 High Similarity NPC103823
0.8678 High Similarity NPC270030
0.8667 High Similarity NPC57199
0.8667 High Similarity NPC74137
0.8667 High Similarity NPC100099
0.8667 High Similarity NPC36016
0.8667 High Similarity NPC41562
0.8661 High Similarity NPC75440
0.8661 High Similarity NPC174981
0.8661 High Similarity NPC245115
0.8651 High Similarity NPC32778
0.8644 High Similarity NPC85895
0.8644 High Similarity NPC137294
0.8644 High Similarity NPC15805
0.8644 High Similarity NPC295259
0.8644 High Similarity NPC226629
0.864 High Similarity NPC471517
0.864 High Similarity NPC15543
0.864 High Similarity NPC12275
0.864 High Similarity NPC45715
0.864 High Similarity NPC472590
0.864 High Similarity NPC473309
0.864 High Similarity NPC474356
0.8629 High Similarity NPC222108
0.8629 High Similarity NPC96719
0.8624 High Similarity NPC100340
0.8624 High Similarity NPC143659
0.8618 High Similarity NPC127587
0.8609 High Similarity NPC35344
0.8609 High Similarity NPC141003
0.8607 High Similarity NPC476254
0.8607 High Similarity NPC82483
0.8607 High Similarity NPC472093
0.8607 High Similarity NPC203133
0.8607 High Similarity NPC57490
0.8607 High Similarity NPC17943
0.8607 High Similarity NPC251855
0.8607 High Similarity NPC221077
0.8607 High Similarity NPC265483
0.8607 High Similarity NPC117214
0.8607 High Similarity NPC233410
0.8607 High Similarity NPC293801
0.8607 High Similarity NPC116907
0.8607 High Similarity NPC298757
0.8607 High Similarity NPC131397
0.8607 High Similarity NPC193544
0.8607 High Similarity NPC475169
0.8607 High Similarity NPC299584
0.8607 High Similarity NPC208950
0.8596 High Similarity NPC224527
0.8595 High Similarity NPC197757
0.8595 High Similarity NPC228922
0.8595 High Similarity NPC76465
0.8595 High Similarity NPC38761
0.8595 High Similarity NPC96940
0.8584 High Similarity NPC19808
0.8584 High Similarity NPC202647
0.8584 High Similarity NPC33728
0.8584 High Similarity NPC82016
0.8583 High Similarity NPC212965
0.8583 High Similarity NPC103967
0.8583 High Similarity NPC285289
0.8583 High Similarity NPC54972
0.8583 High Similarity NPC160697
0.8571 High Similarity NPC6451
0.856 High Similarity NPC299221
0.856 High Similarity NPC51840
0.856 High Similarity NPC311680
0.856 High Similarity NPC234488
0.8548 High Similarity NPC38664
0.8548 High Similarity NPC53986
0.8548 High Similarity NPC28765
0.8548 High Similarity NPC39064
0.8548 High Similarity NPC47283
0.8537 High Similarity NPC262573
0.8537 High Similarity NPC471215
0.8537 High Similarity NPC76451
0.8534 High Similarity NPC470837
0.8525 High Similarity NPC140521
0.8525 High Similarity NPC134195
0.8525 High Similarity NPC246648
0.8525 High Similarity NPC197351
0.8525 High Similarity NPC106914
0.8525 High Similarity NPC86502
0.8516 High Similarity NPC294884

  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 NPC50521 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
0.8898 High Similarity NPD1610 Phase 2
0.878 High Similarity NPD4625 Phase 3
0.8718 High Similarity NPD1548 Phase 1
0.8595 High Similarity NPD4749 Approved
0.8548 High Similarity NPD4908 Phase 1
0.8413 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.84 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8387 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD3027 Phase 3
0.832 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8281 Intermediate Similarity NPD1613 Approved
0.8281 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8268 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD4750 Phase 3
0.8198 Intermediate Similarity NPD1242 Phase 1
0.813 Intermediate Similarity NPD422 Phase 1
0.8125 Intermediate Similarity NPD940 Approved
0.8125 Intermediate Similarity NPD846 Approved
0.8031 Intermediate Similarity NPD2861 Phase 2
0.8 Intermediate Similarity NPD6671 Approved
0.8 Intermediate Similarity NPD709 Approved
0.8 Intermediate Similarity NPD1240 Approved
0.8 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD3018 Phase 2
0.7879 Intermediate Similarity NPD1607 Approved
0.7845 Intermediate Similarity NPD968 Approved
0.7836 Intermediate Similarity NPD6099 Approved
0.7836 Intermediate Similarity NPD6100 Approved
0.7815 Intermediate Similarity NPD228 Approved
0.7778 Intermediate Similarity NPD1608 Approved
0.7768 Intermediate Similarity NPD288 Approved
0.7761 Intermediate Similarity NPD1510 Phase 2
0.7719 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD2982 Phase 2
0.7717 Intermediate Similarity NPD2983 Phase 2
0.771 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7686 Intermediate Similarity NPD5283 Phase 1
0.7679 Intermediate Similarity NPD844 Approved
0.7638 Intermediate Similarity NPD2232 Approved
0.7638 Intermediate Similarity NPD2233 Approved
0.7638 Intermediate Similarity NPD2981 Phase 2
0.7638 Intermediate Similarity NPD2230 Approved
0.7632 Intermediate Similarity NPD3020 Approved
0.7627 Intermediate Similarity NPD290 Approved
0.7609 Intermediate Similarity NPD3892 Phase 2
0.7594 Intermediate Similarity NPD2238 Phase 2
0.7591 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD17 Approved
0.754 Intermediate Similarity NPD4626 Approved
0.7522 Intermediate Similarity NPD2860 Approved
0.7522 Intermediate Similarity NPD2859 Approved
0.7519 Intermediate Similarity NPD6696 Suspended
0.7519 Intermediate Similarity NPD1283 Approved
0.7518 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD3750 Approved
0.7479 Intermediate Similarity NPD2342 Discontinued
0.7464 Intermediate Similarity NPD1549 Phase 2
0.7463 Intermediate Similarity NPD4060 Phase 1
0.7462 Intermediate Similarity NPD2797 Approved
0.746 Intermediate Similarity NPD1651 Approved
0.7459 Intermediate Similarity NPD7635 Approved
0.7445 Intermediate Similarity NPD1551 Phase 2
0.7442 Intermediate Similarity NPD1669 Approved
0.7434 Intermediate Similarity NPD2933 Approved
0.7434 Intermediate Similarity NPD2934 Approved
0.7422 Intermediate Similarity NPD1611 Approved
0.7422 Intermediate Similarity NPD1091 Approved
0.7405 Intermediate Similarity NPD6584 Phase 3
0.7402 Intermediate Similarity NPD1778 Approved
0.7394 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7447 Phase 1
0.7355 Intermediate Similarity NPD3021 Approved
0.7355 Intermediate Similarity NPD3022 Approved
0.7355 Intermediate Similarity NPD5451 Approved
0.7353 Intermediate Similarity NPD4097 Suspended
0.7345 Intermediate Similarity NPD845 Approved
0.7324 Intermediate Similarity NPD1511 Approved
0.7324 Intermediate Similarity NPD7213 Phase 3
0.7324 Intermediate Similarity NPD7212 Phase 2
0.7319 Intermediate Similarity NPD2935 Discontinued
0.7287 Intermediate Similarity NPD1281 Approved
0.7286 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7281 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD1934 Approved
0.7273 Intermediate Similarity NPD2684 Approved
0.7273 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD2667 Approved
0.7266 Intermediate Similarity NPD2668 Approved
0.7266 Intermediate Similarity NPD3540 Phase 1
0.7258 Intermediate Similarity NPD1398 Phase 1
0.7252 Intermediate Similarity NPD3225 Approved
0.7234 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD1512 Approved
0.7209 Intermediate Similarity NPD3496 Discontinued
0.7206 Intermediate Similarity NPD1558 Phase 1
0.7194 Intermediate Similarity NPD3539 Phase 1
0.7194 Intermediate Similarity NPD2796 Approved
0.7188 Intermediate Similarity NPD3444 Approved
0.7188 Intermediate Similarity NPD5691 Approved
0.7188 Intermediate Similarity NPD3443 Approved
0.7188 Intermediate Similarity NPD3445 Approved
0.7185 Intermediate Similarity NPD3268 Approved
0.7177 Intermediate Similarity NPD1138 Approved
0.7176 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6583 Phase 3
0.7176 Intermediate Similarity NPD6582 Phase 2
0.7164 Intermediate Similarity NPD596 Approved
0.7164 Intermediate Similarity NPD600 Approved
0.7153 Intermediate Similarity NPD5124 Phase 1
0.7153 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6387 Discontinued
0.7143 Intermediate Similarity NPD2557 Approved
0.7143 Intermediate Similarity NPD7157 Approved
0.7143 Intermediate Similarity NPD4624 Approved
0.7143 Intermediate Similarity NPD9295 Approved
0.7133 Intermediate Similarity NPD7768 Phase 2
0.7124 Intermediate Similarity NPD6232 Discontinued
0.7122 Intermediate Similarity NPD7033 Discontinued
0.7122 Intermediate Similarity NPD3748 Approved
0.7121 Intermediate Similarity NPD8651 Approved
0.7114 Intermediate Similarity NPD7819 Suspended
0.7114 Intermediate Similarity NPD2801 Approved
0.7113 Intermediate Similarity NPD7466 Approved
0.7105 Intermediate Similarity NPD6746 Phase 2
0.7099 Intermediate Similarity NPD2235 Phase 2
0.7099 Intermediate Similarity NPD2231 Phase 2
0.7097 Intermediate Similarity NPD1139 Approved
0.7097 Intermediate Similarity NPD1137 Approved
0.709 Intermediate Similarity NPD1712 Approved
0.7087 Intermediate Similarity NPD7340 Approved
0.7077 Intermediate Similarity NPD3847 Discontinued
0.7073 Intermediate Similarity NPD1792 Phase 2
0.7069 Intermediate Similarity NPD1809 Phase 2
0.7068 Intermediate Similarity NPD1203 Approved
0.7067 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD5585 Approved
0.705 Intermediate Similarity NPD2200 Suspended
0.7047 Intermediate Similarity NPD37 Approved
0.7042 Intermediate Similarity NPD5177 Phase 3
0.704 Intermediate Similarity NPD821 Approved
0.704 Intermediate Similarity NPD7843 Approved
0.704 Intermediate Similarity NPD5535 Approved
0.7037 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD4380 Phase 2
0.7023 Intermediate Similarity NPD1201 Approved
0.7021 Intermediate Similarity NPD5763 Approved
0.7021 Intermediate Similarity NPD5762 Approved
0.702 Intermediate Similarity NPD3882 Suspended
0.7015 Intermediate Similarity NPD2798 Approved
0.7014 Intermediate Similarity NPD7124 Phase 2
0.7007 Intermediate Similarity NPD840 Approved
0.7007 Intermediate Similarity NPD839 Approved
0.6987 Remote Similarity NPD7473 Discontinued
0.6986 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6985 Remote Similarity NPD7095 Approved
0.6985 Remote Similarity NPD1024 Discontinued
0.6978 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6977 Remote Similarity NPD1182 Approved
0.6974 Remote Similarity NPD4055 Discovery
0.6972 Remote Similarity NPD9089 Approved
0.697 Remote Similarity NPD1840 Phase 2
0.6967 Remote Similarity NPD1444 Approved
0.6967 Remote Similarity NPD1445 Approved
0.6966 Remote Similarity NPD7041 Phase 2
0.6966 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4357 Discontinued
0.6959 Remote Similarity NPD4005 Discontinued
0.6957 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6957 Remote Similarity NPD3620 Phase 2
0.6957 Remote Similarity NPD943 Approved
0.6953 Remote Similarity NPD9493 Approved
0.6948 Remote Similarity NPD6959 Discontinued
0.694 Remote Similarity NPD3266 Approved
0.694 Remote Similarity NPD3267 Approved
0.6937 Remote Similarity NPD111 Approved
0.6934 Remote Similarity NPD1296 Phase 2
0.6929 Remote Similarity NPD497 Approved
0.6929 Remote Similarity NPD6111 Discontinued
0.6928 Remote Similarity NPD6234 Discontinued
0.6923 Remote Similarity NPD1357 Approved
0.6923 Remote Similarity NPD3049 Approved
0.6923 Remote Similarity NPD1652 Phase 2
0.6918 Remote Similarity NPD2533 Approved
0.6918 Remote Similarity NPD2532 Approved
0.6918 Remote Similarity NPD2534 Approved
0.6917 Remote Similarity NPD5327 Phase 3
0.6908 Remote Similarity NPD4967 Phase 2
0.6908 Remote Similarity NPD4965 Approved
0.6908 Remote Similarity NPD4966 Approved
0.6908 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6906 Remote Similarity NPD5735 Approved
0.6906 Remote Similarity NPD6355 Discontinued
0.6903 Remote Similarity NPD7229 Phase 3
0.6901 Remote Similarity NPD2344 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