Structure

Physi-Chem Properties

Molecular Weight:  329.16
Volume:  335.93
LogP:  1.463
LogD:  1.725
LogS:  -2.031
# Rotatable Bonds:  3
TPSA:  51.16
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.921
Synthetic Accessibility Score:  4.803
Fsp3:  0.474
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.827
MDCK Permeability:  2.6864614483201876e-05
Pgp-inhibitor:  0.151
Pgp-substrate:  0.959
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.508
30% Bioavailability (F30%):  0.227

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.99
Plasma Protein Binding (PPB):  53.854759216308594%
Volume Distribution (VD):  2.932
Pgp-substrate:  36.738525390625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.294
CYP2C19-inhibitor:  0.032
CYP2C19-substrate:  0.941
CYP2C9-inhibitor:  0.099
CYP2C9-substrate:  0.422
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.372
CYP3A4-inhibitor:  0.248
CYP3A4-substrate:  0.945

ADMET: Excretion

Clearance (CL):  11.851
Half-life (T1/2):  0.755

ADMET: Toxicity

hERG Blockers:  0.391
Human Hepatotoxicity (H-HT):  0.868
Drug-inuced Liver Injury (DILI):  0.163
AMES Toxicity:  0.697
Rat Oral Acute Toxicity:  0.358
Maximum Recommended Daily Dose:  0.985
Skin Sensitization:  0.493
Carcinogencity:  0.893
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.962

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

  Natural Product: NPC59028

Natural Product ID:  NPC59028
Common Name*:   (+)-R-Hydroxyerysotrine
IUPAC Name:   (2R,9S,13bS)-2,11,12-trimethoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-9-ol
Synonyms:   (+)-R-Hydroxyerysotrine
Standard InCHIKey:  QWWCVLZNFFVFTR-CRFBAAHOSA-N
Standard InCHI:  InChI=1S/C19H23NO4/c1-22-13-5-4-12-6-7-20-11-16(21)14-8-17(23-2)18(24-3)9-15(14)19(12,20)10-13/h4-6,8-9,13,16,21H,7,10-11H2,1-3H3/t13-,16+,19-/m0/s1
SMILES:  CO[C@H]1C=CC2=CCN3C[C@H](c4cc(c(cc4[C@]23C1)OC)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL217996
PubChem CID:   11472951
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001782] Erythrina alkaloids
        • [CHEMONTID:0002780] Erythrinanes

*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
NPO11659 Erythrina mulungu Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[17253849]
NPO11659 Erythrina mulungu Species Fabaceae 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 Activity = 135.3 n.a. PMID[509968]
NPT32 Organism Mus musculus Mus musculus Activity = 29.6 n.a. PMID[509968]
NPT32 Organism Mus musculus Mus musculus Activity = 159.0 n.a. PMID[509968]
NPT32 Organism Mus musculus Mus musculus Activity = 29.63 n.a. PMID[509968]

☑ 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 NPC59028 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 NPC92191
0.9527 High Similarity NPC274026
0.9272 High Similarity NPC82285
0.9272 High Similarity NPC133011
0.9189 High Similarity NPC130926
0.9062 High Similarity NPC470739
0.9062 High Similarity NPC477640
0.9062 High Similarity NPC225597
0.9 High Similarity NPC474475
0.8951 High Similarity NPC49353
0.8938 High Similarity NPC58766
0.8938 High Similarity NPC290759
0.8938 High Similarity NPC266176
0.8938 High Similarity NPC475686
0.8938 High Similarity NPC82533
0.8938 High Similarity NPC158148
0.8917 High Similarity NPC249274
0.8917 High Similarity NPC205167
0.891 High Similarity NPC475326
0.8889 High Similarity NPC2314
0.8846 High Similarity NPC147091
0.8774 High Similarity NPC148898
0.8758 High Similarity NPC150879
0.8758 High Similarity NPC100566
0.8696 High Similarity NPC476002
0.8684 High Similarity NPC185838
0.8667 High Similarity NPC474470
0.8642 High Similarity NPC181653
0.8642 High Similarity NPC190332
0.8636 High Similarity NPC135538
0.8636 High Similarity NPC24233
0.8636 High Similarity NPC147390
0.8636 High Similarity NPC476571
0.8636 High Similarity NPC246587
0.8636 High Similarity NPC428
0.8606 High Similarity NPC187678
0.8571 High Similarity NPC191376
0.8571 High Similarity NPC233650
0.8571 High Similarity NPC476151
0.8571 High Similarity NPC320104
0.8571 High Similarity NPC321505
0.8571 High Similarity NPC179825
0.8563 High Similarity NPC244554
0.8562 High Similarity NPC4304
0.8562 High Similarity NPC97072
0.8562 High Similarity NPC215829
0.8543 High Similarity NPC188163
0.8543 High Similarity NPC328750
0.8543 High Similarity NPC474915
0.8543 High Similarity NPC213206
0.8528 High Similarity NPC252960
0.8519 High Similarity NPC134858
0.8519 High Similarity NPC169743
0.8477 Intermediate Similarity NPC314682
0.8462 Intermediate Similarity NPC248642
0.8462 Intermediate Similarity NPC103379
0.8462 Intermediate Similarity NPC477565
0.8457 Intermediate Similarity NPC218614
0.8443 Intermediate Similarity NPC237044
0.8438 Intermediate Similarity NPC148014
0.8438 Intermediate Similarity NPC315707
0.8438 Intermediate Similarity NPC40389
0.8438 Intermediate Similarity NPC78359
0.8438 Intermediate Similarity NPC65490
0.8428 Intermediate Similarity NPC39701
0.8428 Intermediate Similarity NPC207757
0.8428 Intermediate Similarity NPC54379
0.8428 Intermediate Similarity NPC110416
0.8428 Intermediate Similarity NPC172765
0.8428 Intermediate Similarity NPC189266
0.8428 Intermediate Similarity NPC295691
0.8428 Intermediate Similarity NPC5238
0.8428 Intermediate Similarity NPC469817
0.8428 Intermediate Similarity NPC249797
0.8428 Intermediate Similarity NPC127674
0.8428 Intermediate Similarity NPC193949
0.8428 Intermediate Similarity NPC2413
0.8428 Intermediate Similarity NPC276588
0.8428 Intermediate Similarity NPC278799
0.8428 Intermediate Similarity NPC204828
0.8428 Intermediate Similarity NPC184026
0.8415 Intermediate Similarity NPC210140
0.8412 Intermediate Similarity NPC156576
0.8408 Intermediate Similarity NPC151895
0.8408 Intermediate Similarity NPC192768
0.8408 Intermediate Similarity NPC88249
0.8408 Intermediate Similarity NPC97221
0.8408 Intermediate Similarity NPC220858
0.8405 Intermediate Similarity NPC231198
0.8393 Intermediate Similarity NPC474325
0.8383 Intermediate Similarity NPC304675
0.8375 Intermediate Similarity NPC160931
0.8375 Intermediate Similarity NPC37205
0.8364 Intermediate Similarity NPC160570
0.8354 Intermediate Similarity NPC13916
0.8354 Intermediate Similarity NPC264850
0.8353 Intermediate Similarity NPC233718
0.8344 Intermediate Similarity NPC207824
0.8344 Intermediate Similarity NPC60538
0.8343 Intermediate Similarity NPC474745
0.8343 Intermediate Similarity NPC126284
0.8333 Intermediate Similarity NPC51957
0.8333 Intermediate Similarity NPC106295
0.8333 Intermediate Similarity NPC16107
0.8333 Intermediate Similarity NPC210437
0.8333 Intermediate Similarity NPC476144
0.8313 Intermediate Similarity NPC311991
0.8313 Intermediate Similarity NPC78733
0.8312 Intermediate Similarity NPC136860
0.8312 Intermediate Similarity NPC476567
0.8312 Intermediate Similarity NPC128019
0.8303 Intermediate Similarity NPC117188
0.8303 Intermediate Similarity NPC158376
0.8303 Intermediate Similarity NPC12053
0.8303 Intermediate Similarity NPC205421
0.8303 Intermediate Similarity NPC306555
0.8303 Intermediate Similarity NPC145832
0.8303 Intermediate Similarity NPC474931
0.8303 Intermediate Similarity NPC81218
0.8293 Intermediate Similarity NPC247972
0.8293 Intermediate Similarity NPC24465
0.8284 Intermediate Similarity NPC294790
0.8284 Intermediate Similarity NPC118633
0.8284 Intermediate Similarity NPC148693
0.8282 Intermediate Similarity NPC60186
0.828 Intermediate Similarity NPC7467
0.828 Intermediate Similarity NPC475959
0.8278 Intermediate Similarity NPC131204
0.8278 Intermediate Similarity NPC301050
0.8253 Intermediate Similarity NPC83198
0.8253 Intermediate Similarity NPC204908
0.8243 Intermediate Similarity NPC160193
0.8242 Intermediate Similarity NPC124657
0.8239 Intermediate Similarity NPC277669
0.8239 Intermediate Similarity NPC76213
0.8225 Intermediate Similarity NPC241704
0.8221 Intermediate Similarity NPC18402
0.8214 Intermediate Similarity NPC232386
0.8214 Intermediate Similarity NPC190783
0.8214 Intermediate Similarity NPC152680
0.821 Intermediate Similarity NPC129603
0.821 Intermediate Similarity NPC476572
0.8204 Intermediate Similarity NPC75958
0.8204 Intermediate Similarity NPC329911
0.8198 Intermediate Similarity NPC475981
0.8198 Intermediate Similarity NPC474746
0.8193 Intermediate Similarity NPC474324
0.8193 Intermediate Similarity NPC57812
0.8187 Intermediate Similarity NPC37272
0.8182 Intermediate Similarity NPC232514
0.8182 Intermediate Similarity NPC136508
0.8182 Intermediate Similarity NPC253043
0.8182 Intermediate Similarity NPC477563
0.8182 Intermediate Similarity NPC306843
0.8182 Intermediate Similarity NPC276944
0.8182 Intermediate Similarity NPC76116
0.8182 Intermediate Similarity NPC78222
0.8182 Intermediate Similarity NPC196447
0.8182 Intermediate Similarity NPC212794
0.8182 Intermediate Similarity NPC238530
0.8182 Intermediate Similarity NPC13504
0.8182 Intermediate Similarity NPC96603
0.816 Intermediate Similarity NPC111485
0.8155 Intermediate Similarity NPC57272
0.8148 Intermediate Similarity NPC323443
0.8148 Intermediate Similarity NPC180756
0.8144 Intermediate Similarity NPC475845
0.8137 Intermediate Similarity NPC2295
0.8137 Intermediate Similarity NPC477564
0.8129 Intermediate Similarity NPC99179
0.8129 Intermediate Similarity NPC32154
0.8125 Intermediate Similarity NPC476579
0.8121 Intermediate Similarity NPC124433
0.8121 Intermediate Similarity NPC293871
0.8121 Intermediate Similarity NPC1229
0.8121 Intermediate Similarity NPC324144
0.8103 Intermediate Similarity NPC214116
0.8103 Intermediate Similarity NPC230098
0.8095 Intermediate Similarity NPC474708
0.8086 Intermediate Similarity NPC99659
0.8086 Intermediate Similarity NPC325871
0.8086 Intermediate Similarity NPC41178
0.8086 Intermediate Similarity NPC216459
0.8086 Intermediate Similarity NPC138487
0.807 Intermediate Similarity NPC320223
0.807 Intermediate Similarity NPC15919
0.807 Intermediate Similarity NPC114364
0.8047 Intermediate Similarity NPC476331
0.8046 Intermediate Similarity NPC9867
0.8037 Intermediate Similarity NPC146288
0.8036 Intermediate Similarity NPC164429
0.8025 Intermediate Similarity NPC294249
0.8012 Intermediate Similarity NPC59567
0.8 Intermediate Similarity NPC66341
0.8 Intermediate Similarity NPC192135
0.8 Intermediate Similarity NPC27410
0.8 Intermediate Similarity NPC166014
0.8 Intermediate Similarity NPC477020
0.7988 Intermediate Similarity NPC109925
0.7987 Intermediate Similarity NPC253429

  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 NPC59028 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
0.8608 High Similarity NPD6818 Clinical (unspecified phase)
0.8543 High Similarity NPD4664 Clinical (unspecified phase)
0.8481 Intermediate Similarity NPD4773 Phase 2
0.8481 Intermediate Similarity NPD4772 Phase 2
0.8466 Intermediate Similarity NPD6071 Discontinued
0.8438 Intermediate Similarity NPD2560 Approved
0.8438 Intermediate Similarity NPD2563 Approved
0.8377 Intermediate Similarity NPD5241 Discontinued
0.8333 Intermediate Similarity NPD4584 Approved
0.8193 Intermediate Similarity NPD2970 Approved
0.8193 Intermediate Similarity NPD2969 Approved
0.8129 Intermediate Similarity NPD4236 Phase 3
0.8129 Intermediate Similarity NPD4237 Approved
0.8037 Intermediate Similarity NPD5773 Approved
0.8037 Intermediate Similarity NPD5772 Approved
0.8036 Intermediate Similarity NPD27 Approved
0.8036 Intermediate Similarity NPD2489 Approved
0.8025 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD3051 Approved
0.8013 Intermediate Similarity NPD3060 Approved
0.8012 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD2898 Approved
0.7901 Intermediate Similarity NPD4017 Approved
0.7898 Intermediate Similarity NPD7906 Approved
0.7888 Intermediate Similarity NPD3639 Approved
0.7888 Intermediate Similarity NPD6031 Approved
0.7888 Intermediate Similarity NPD6030 Approved
0.7888 Intermediate Similarity NPD3641 Approved
0.7888 Intermediate Similarity NPD3640 Phase 3
0.7875 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD6107 Approved
0.7841 Intermediate Similarity NPD4663 Approved
0.7829 Intermediate Similarity NPD8053 Approved
0.7829 Intermediate Similarity NPD8054 Approved
0.7818 Intermediate Similarity NPD2978 Approved
0.7818 Intermediate Similarity NPD2977 Approved
0.7811 Intermediate Similarity NPD4010 Discontinued
0.7791 Intermediate Similarity NPD8156 Discontinued
0.7785 Intermediate Similarity NPD5177 Phase 3
0.7784 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7831 Phase 2
0.7784 Intermediate Similarity NPD7833 Phase 2
0.7771 Intermediate Similarity NPD7313 Approved
0.7771 Intermediate Similarity NPD7311 Approved
0.7771 Intermediate Similarity NPD7310 Approved
0.7771 Intermediate Similarity NPD4577 Approved
0.7771 Intermediate Similarity NPD4578 Approved
0.7771 Intermediate Similarity NPD7312 Approved
0.7764 Intermediate Similarity NPD4123 Phase 3
0.7763 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD7298 Approved
0.7733 Intermediate Similarity NPD8099 Discontinued
0.7733 Intermediate Similarity NPD8251 Approved
0.7733 Intermediate Similarity NPD8252 Approved
0.7727 Intermediate Similarity NPD7309 Approved
0.7727 Intermediate Similarity NPD2238 Phase 2
0.7719 Intermediate Similarity NPD4481 Phase 3
0.7688 Intermediate Similarity NPD2677 Approved
0.7673 Intermediate Similarity NPD4162 Approved
0.7658 Intermediate Similarity NPD1375 Discontinued
0.7643 Intermediate Similarity NPD1753 Discontinued
0.764 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD4210 Discontinued
0.7622 Intermediate Similarity NPD3687 Approved
0.7622 Intermediate Similarity NPD3686 Approved
0.7619 Intermediate Similarity NPD6788 Approved
0.76 Intermediate Similarity NPD6297 Approved
0.7597 Intermediate Similarity NPD5718 Phase 2
0.7576 Intermediate Similarity NPD4005 Discontinued
0.7546 Intermediate Similarity NPD1424 Approved
0.7541 Intermediate Similarity NPD5582 Discontinued
0.7541 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD4675 Approved
0.753 Intermediate Similarity NPD4678 Approved
0.7528 Intermediate Similarity NPD6853 Approved
0.7528 Intermediate Similarity NPD6851 Approved
0.7516 Intermediate Similarity NPD817 Approved
0.7516 Intermediate Similarity NPD823 Approved
0.7515 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD5313 Approved
0.7486 Intermediate Similarity NPD5312 Approved
0.7484 Intermediate Similarity NPD2161 Phase 2
0.747 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD3692 Discontinued
0.7468 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD4420 Approved
0.7436 Intermediate Similarity NPD2674 Phase 3
0.7405 Intermediate Similarity NPD2973 Approved
0.7405 Intermediate Similarity NPD2974 Approved
0.7405 Intermediate Similarity NPD2975 Approved
0.7399 Intermediate Similarity NPD4166 Phase 2
0.7394 Intermediate Similarity NPD6090 Discontinued
0.7394 Intermediate Similarity NPD5006 Approved
0.7394 Intermediate Similarity NPD5005 Approved
0.7386 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4103 Phase 2
0.7384 Intermediate Similarity NPD5677 Discontinued
0.7378 Intermediate Similarity NPD3124 Discontinued
0.7368 Intermediate Similarity NPD5604 Discontinued
0.7358 Intermediate Similarity NPD6896 Approved
0.7358 Intermediate Similarity NPD6895 Approved
0.7356 Intermediate Similarity NPD6688 Approved
0.7356 Intermediate Similarity NPD6687 Approved
0.7349 Intermediate Similarity NPD2122 Discontinued
0.7341 Intermediate Similarity NPD7802 Discontinued
0.734 Intermediate Similarity NPD3450 Approved
0.734 Intermediate Similarity NPD3452 Approved
0.734 Intermediate Similarity NPD2493 Approved
0.734 Intermediate Similarity NPD2494 Approved
0.7329 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD1130 Approved
0.7325 Intermediate Similarity NPD1132 Approved
0.7325 Intermediate Similarity NPD1136 Approved
0.7317 Intermediate Similarity NPD3122 Phase 3
0.7317 Intermediate Similarity NPD7124 Phase 2
0.7303 Intermediate Similarity NPD2232 Approved
0.7303 Intermediate Similarity NPD2230 Approved
0.7303 Intermediate Similarity NPD2233 Approved
0.7289 Intermediate Similarity NPD7526 Approved
0.7289 Intermediate Similarity NPD52 Approved
0.7289 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD4580 Approved
0.7278 Intermediate Similarity NPD3061 Approved
0.7278 Intermediate Similarity NPD3059 Approved
0.7278 Intermediate Similarity NPD3062 Approved
0.7273 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1774 Approved
0.7273 Intermediate Similarity NPD2420 Approved
0.7273 Intermediate Similarity NPD2421 Approved
0.7268 Intermediate Similarity NPD2845 Phase 2
0.7268 Intermediate Similarity NPD2843 Phase 2
0.7267 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD4055 Discovery
0.7263 Intermediate Similarity NPD7039 Approved
0.7263 Intermediate Similarity NPD7038 Approved
0.7261 Intermediate Similarity NPD601 Approved
0.7261 Intermediate Similarity NPD597 Approved
0.7261 Intermediate Similarity NPD598 Approved
0.7261 Intermediate Similarity NPD3144 Approved
0.7261 Intermediate Similarity NPD3145 Approved
0.7256 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD4659 Approved
0.7251 Intermediate Similarity NPD5978 Approved
0.7251 Intermediate Similarity NPD5977 Approved
0.7246 Intermediate Similarity NPD5976 Discontinued
0.7229 Intermediate Similarity NPD3157 Approved
0.7229 Intermediate Similarity NPD3158 Phase 1
0.7228 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD2490 Approved
0.7228 Intermediate Similarity NPD2488 Approved
0.7225 Intermediate Similarity NPD4582 Approved
0.7225 Intermediate Similarity NPD4583 Approved
0.7222 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2667 Approved
0.7219 Intermediate Similarity NPD2668 Approved
0.7213 Intermediate Similarity NPD4157 Discontinued
0.7212 Intermediate Similarity NPD3845 Phase 1
0.7195 Intermediate Similarity NPD6331 Phase 2
0.7195 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD6042 Phase 2
0.7191 Intermediate Similarity NPD42 Phase 2
0.7189 Intermediate Similarity NPD7296 Approved
0.7188 Intermediate Similarity NPD5314 Approved
0.7184 Intermediate Similarity NPD2904 Discontinued
0.7182 Intermediate Similarity NPD2971 Approved
0.7182 Intermediate Similarity NPD2968 Approved
0.7178 Intermediate Similarity NPD7153 Discontinued
0.7173 Intermediate Similarity NPD4002 Approved
0.7173 Intermediate Similarity NPD4004 Approved
0.7168 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD5242 Approved
0.7152 Intermediate Similarity NPD5160 Discontinued
0.7135 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD5709 Phase 3
0.712 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD3656 Approved
0.7115 Intermediate Similarity NPD9621 Approved
0.7115 Intermediate Similarity NPD9619 Approved
0.7115 Intermediate Similarity NPD9620 Approved
0.7111 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD3531 Approved
0.7107 Intermediate Similarity NPD4475 Approved
0.7107 Intermediate Similarity NPD3532 Approved
0.7107 Intermediate Similarity NPD3530 Approved
0.7107 Intermediate Similarity NPD4474 Approved
0.7105 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD3179 Approved
0.7089 Intermediate Similarity NPD3027 Phase 3
0.7089 Intermediate Similarity NPD3180 Approved
0.7088 Intermediate Similarity NPD7281 Phase 3
0.7088 Intermediate Similarity NPD7280 Phase 3
0.7088 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD2042 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD2041 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD4666 Phase 3
0.7083 Intermediate Similarity NPD5261 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
A: chemistry similarity;
B: biological targets similarity;
C: networks similarity;
D: cell-based bioactivity similarity;
E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data