Structure

Physi-Chem Properties

Molecular Weight:  299.15
Volume:  309.844
LogP:  2.172
LogD:  2.157
LogS:  -2.412
# Rotatable Bonds:  2
TPSA:  41.93
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.91
Synthetic Accessibility Score:  4.543
Fsp3:  0.444
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.786
MDCK Permeability:  2.4463539375574328e-05
Pgp-inhibitor:  0.39
Pgp-substrate:  0.941
Human Intestinal Absorption (HIA):  0.051
20% Bioavailability (F20%):  0.883
30% Bioavailability (F30%):  0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.998
Plasma Protein Binding (PPB):  64.25745391845703%
Volume Distribution (VD):  2.805
Pgp-substrate:  19.944700241088867%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.426
CYP2C19-inhibitor:  0.073
CYP2C19-substrate:  0.898
CYP2C9-inhibitor:  0.315
CYP2C9-substrate:  0.674
CYP2D6-inhibitor:  0.109
CYP2D6-substrate:  0.542
CYP3A4-inhibitor:  0.705
CYP3A4-substrate:  0.934

ADMET: Excretion

Clearance (CL):  17.144
Half-life (T1/2):  0.714

ADMET: Toxicity

hERG Blockers:  0.366
Human Hepatotoxicity (H-HT):  0.827
Drug-inuced Liver Injury (DILI):  0.231
AMES Toxicity:  0.788
Rat Oral Acute Toxicity:  0.113
Maximum Recommended Daily Dose:  0.962
Skin Sensitization:  0.914
Carcinogencity:  0.892
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.888

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

  Natural Product: NPC133011

Natural Product ID:  NPC133011
Common Name*:   Erysovine
IUPAC Name:   (2R,13bS)-2,11-dimethoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-12-ol
Synonyms:   Erysovine
Standard InCHIKey:  IHPMURIXWRKEKD-KSSFIOAISA-N
Standard InCHI:  InChI=1S/C18H21NO3/c1-21-14-4-3-13-6-8-19-7-5-12-9-17(22-2)16(20)10-15(12)18(13,19)11-14/h3-4,6,9-10,14,20H,5,7-8,11H2,1-2H3/t14-,18-/m0/s1
SMILES:  CO[C@H]1C=CC2=CCN3CCc4cc(c(cc4[C@]23C1)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL517778
PubChem CID:   5317203
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
NPO14905 Erythrina variegata Species Fabaceae Eukaryota n.a. root n.a. PMID[10869220]
NPO20031 Erythrina velutina Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19026536]
NPO8301 Erythrina suberosa Species Fabaceae Eukaryota n.a. seed n.a. PMID[5348524]
NPO13279 Berberis zycium Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7457 Erythrina berteroana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14905 Erythrina variegata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8301 Erythrina suberosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17657 Erythrina arborescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14905 Erythrina variegata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8301 Erythrina suberosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7457 Erythrina berteroana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28361 Erythrina salviiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13279 Berberis zycium Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16399 Erythrina folkersii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17657 Erythrina arborescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30554 Erythrina folkersll Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29998 Erythrina salvllflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17657 Erythrina arborescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14905 Erythrina variegata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8301 Erythrina suberosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13279 Berberis zycium Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7457 Erythrina berteroana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17657 Erythrina arborescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3174 Sulfolobus shibatae Species Sulfolobaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO16399 Erythrina folkersii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24842 Bulla gouldiana Species Bullidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28361 Erythrina salviiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20031 Erythrina velutina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8301 Erythrina suberosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14905 Erythrina variegata 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
NPT15 Cell Line Jurkat Homo sapiens IC50 = 24.0 ug.mL-1 PMID[554321]
NPT15 Cell Line Jurkat Homo sapiens IC50 = 14.2 ug.mL-1 PMID[554321]

☑ 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 NPC133011 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 NPC82285
0.9722 High Similarity NPC274026
0.951 High Similarity NPC130926
0.9463 High Similarity NPC475326
0.9396 High Similarity NPC147091
0.9272 High Similarity NPC59028
0.9272 High Similarity NPC92191
0.9247 High Similarity NPC191376
0.9247 High Similarity NPC179825
0.9247 High Similarity NPC321505
0.9184 High Similarity NPC147390
0.9184 High Similarity NPC246587
0.9184 High Similarity NPC135538
0.9184 High Similarity NPC476571
0.9184 High Similarity NPC428
0.9184 High Similarity NPC24233
0.9122 High Similarity NPC477565
0.9122 High Similarity NPC103379
0.911 High Similarity NPC185838
0.9085 High Similarity NPC205167
0.9085 High Similarity NPC249274
0.9067 High Similarity NPC148898
0.8986 High Similarity NPC476151
0.8951 High Similarity NPC301050
0.8951 High Similarity NPC131204
0.8947 High Similarity NPC278799
0.8947 High Similarity NPC249797
0.8947 High Similarity NPC189266
0.8947 High Similarity NPC110416
0.8947 High Similarity NPC193949
0.8947 High Similarity NPC5238
0.8947 High Similarity NPC207757
0.8947 High Similarity NPC204828
0.8947 High Similarity NPC172765
0.8947 High Similarity NPC127674
0.8947 High Similarity NPC276588
0.8947 High Similarity NPC2413
0.8947 High Similarity NPC184026
0.8947 High Similarity NPC469817
0.8947 High Similarity NPC295691
0.8947 High Similarity NPC39701
0.8947 High Similarity NPC54379
0.8933 High Similarity NPC151895
0.8933 High Similarity NPC97221
0.8933 High Similarity NPC220858
0.8933 High Similarity NPC192768
0.8933 High Similarity NPC88249
0.8874 High Similarity NPC277669
0.8874 High Similarity NPC76213
0.8767 High Similarity NPC314682
0.8758 High Similarity NPC477564
0.8758 High Similarity NPC2295
0.8742 High Similarity NPC207824
0.8742 High Similarity NPC60538
0.8718 High Similarity NPC215829
0.8718 High Similarity NPC97072
0.8707 High Similarity NPC213206
0.8707 High Similarity NPC474915
0.8707 High Similarity NPC328750
0.8707 High Similarity NPC188163
0.8693 High Similarity NPC37272
0.8671 High Similarity NPC238530
0.8671 High Similarity NPC232514
0.8671 High Similarity NPC276944
0.8658 High Similarity NPC294249
0.8654 High Similarity NPC111485
0.8642 High Similarity NPC49353
0.8599 High Similarity NPC166014
0.8599 High Similarity NPC27410
0.8581 High Similarity NPC78733
0.8562 High Similarity NPC210140
0.8562 High Similarity NPC100566
0.8553 High Similarity NPC231198
0.8531 High Similarity NPC160193
0.8519 High Similarity NPC476331
0.8509 High Similarity NPC470324
0.85 High Similarity NPC13916
0.85 High Similarity NPC124657
0.85 High Similarity NPC264850
0.8487 Intermediate Similarity NPC476144
0.8487 Intermediate Similarity NPC210437
0.8487 Intermediate Similarity NPC106295
0.8487 Intermediate Similarity NPC51957
0.8487 Intermediate Similarity NPC16107
0.8481 Intermediate Similarity NPC18402
0.8467 Intermediate Similarity NPC476567
0.8467 Intermediate Similarity NPC128019
0.8467 Intermediate Similarity NPC136860
0.8447 Intermediate Similarity NPC190332
0.8447 Intermediate Similarity NPC181653
0.8438 Intermediate Similarity NPC134858
0.8438 Intermediate Similarity NPC24465
0.8431 Intermediate Similarity NPC7467
0.8431 Intermediate Similarity NPC475959
0.8428 Intermediate Similarity NPC60186
0.8415 Intermediate Similarity NPC187678
0.8408 Intermediate Similarity NPC186063
0.8405 Intermediate Similarity NPC477640
0.8405 Intermediate Similarity NPC470739
0.8405 Intermediate Similarity NPC225597
0.8395 Intermediate Similarity NPC158148
0.8395 Intermediate Similarity NPC83198
0.8395 Intermediate Similarity NPC475686
0.8395 Intermediate Similarity NPC82533
0.8395 Intermediate Similarity NPC204908
0.8395 Intermediate Similarity NPC266176
0.8395 Intermediate Similarity NPC58766
0.8395 Intermediate Similarity NPC290759
0.8385 Intermediate Similarity NPC256012
0.8385 Intermediate Similarity NPC42549
0.8385 Intermediate Similarity NPC250846
0.8385 Intermediate Similarity NPC268503
0.8385 Intermediate Similarity NPC240841
0.8385 Intermediate Similarity NPC317272
0.8375 Intermediate Similarity NPC233650
0.8375 Intermediate Similarity NPC320104
0.8375 Intermediate Similarity NPC324144
0.8344 Intermediate Similarity NPC474475
0.8333 Intermediate Similarity NPC306555
0.8333 Intermediate Similarity NPC26601
0.8333 Intermediate Similarity NPC145832
0.8333 Intermediate Similarity NPC474931
0.8333 Intermediate Similarity NPC81218
0.8333 Intermediate Similarity NPC158376
0.8333 Intermediate Similarity NPC12053
0.8333 Intermediate Similarity NPC117188
0.8333 Intermediate Similarity NPC205421
0.8323 Intermediate Similarity NPC284183
0.8323 Intermediate Similarity NPC477563
0.8323 Intermediate Similarity NPC4138
0.8323 Intermediate Similarity NPC212794
0.8323 Intermediate Similarity NPC121275
0.8323 Intermediate Similarity NPC13504
0.8323 Intermediate Similarity NPC78222
0.8323 Intermediate Similarity NPC136508
0.8323 Intermediate Similarity NPC306843
0.8323 Intermediate Similarity NPC253043
0.8323 Intermediate Similarity NPC196447
0.8323 Intermediate Similarity NPC96603
0.8272 Intermediate Similarity NPC81247
0.8272 Intermediate Similarity NPC476002
0.8272 Intermediate Similarity NPC476573
0.8272 Intermediate Similarity NPC35627
0.8269 Intermediate Similarity NPC476579
0.8263 Intermediate Similarity NPC32154
0.8261 Intermediate Similarity NPC1229
0.8255 Intermediate Similarity NPC253429
0.8253 Intermediate Similarity NPC237044
0.8242 Intermediate Similarity NPC152680
0.8242 Intermediate Similarity NPC232386
0.8242 Intermediate Similarity NPC2314
0.8242 Intermediate Similarity NPC190783
0.8239 Intermediate Similarity NPC148014
0.8239 Intermediate Similarity NPC78359
0.8239 Intermediate Similarity NPC65490
0.8239 Intermediate Similarity NPC40389
0.8239 Intermediate Similarity NPC315707
0.8228 Intermediate Similarity NPC41178
0.8228 Intermediate Similarity NPC138487
0.8228 Intermediate Similarity NPC216459
0.8221 Intermediate Similarity NPC298979
0.8221 Intermediate Similarity NPC150879
0.8217 Intermediate Similarity NPC223124
0.8204 Intermediate Similarity NPC474325
0.8193 Intermediate Similarity NPC304675
0.8188 Intermediate Similarity NPC7018
0.8176 Intermediate Similarity NPC146288
0.8176 Intermediate Similarity NPC37205
0.8176 Intermediate Similarity NPC160931
0.8171 Intermediate Similarity NPC66573
0.8171 Intermediate Similarity NPC164429
0.8155 Intermediate Similarity NPC474745
0.8153 Intermediate Similarity NPC81733
0.8153 Intermediate Similarity NPC326316
0.8148 Intermediate Similarity NPC59567
0.8144 Intermediate Similarity NPC474470
0.8144 Intermediate Similarity NPC241704
0.8141 Intermediate Similarity NPC219162
0.8138 Intermediate Similarity NPC172403
0.8137 Intermediate Similarity NPC226428
0.8137 Intermediate Similarity NPC4304
0.8133 Intermediate Similarity NPC193528
0.8121 Intermediate Similarity NPC168753
0.8121 Intermediate Similarity NPC109925
0.8121 Intermediate Similarity NPC118274
0.8121 Intermediate Similarity NPC311991
0.8108 Intermediate Similarity NPC160692
0.8101 Intermediate Similarity NPC210148
0.8101 Intermediate Similarity NPC233029
0.8098 Intermediate Similarity NPC255607
0.8098 Intermediate Similarity NPC3375
0.8095 Intermediate Similarity NPC114364
0.8095 Intermediate Similarity NPC320223
0.8095 Intermediate Similarity NPC21885
0.8089 Intermediate Similarity NPC223125
0.8084 Intermediate Similarity NPC128560
0.8084 Intermediate Similarity NPC229166
0.8084 Intermediate Similarity NPC199465
0.8079 Intermediate Similarity NPC211468
0.8079 Intermediate Similarity NPC170170

  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 NPC133011 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
0.8707 High Similarity NPD4664 Clinical (unspecified phase)
0.8636 High Similarity NPD4772 Phase 2
0.8636 High Similarity NPD4773 Phase 2
0.8509 High Similarity NPD2898 Approved
0.8487 Intermediate Similarity NPD4584 Approved
0.8289 Intermediate Similarity NPD5241 Discontinued
0.8282 Intermediate Similarity NPD27 Approved
0.8282 Intermediate Similarity NPD2489 Approved
0.8272 Intermediate Similarity NPD6071 Discontinued
0.8272 Intermediate Similarity NPD4010 Discontinued
0.8247 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD2563 Approved
0.8239 Intermediate Similarity NPD2560 Approved
0.8153 Intermediate Similarity NPD4017 Approved
0.8141 Intermediate Similarity NPD3639 Approved
0.8141 Intermediate Similarity NPD3640 Phase 3
0.8141 Intermediate Similarity NPD3641 Approved
0.8137 Intermediate Similarity NPD7833 Phase 2
0.8137 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD7831 Phase 2
0.811 Intermediate Similarity NPD2969 Approved
0.811 Intermediate Similarity NPD2970 Approved
0.8063 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD2674 Phase 3
0.8037 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8027 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD6030 Approved
0.8025 Intermediate Similarity NPD6031 Approved
0.7953 Intermediate Similarity NPD8053 Approved
0.7953 Intermediate Similarity NPD8054 Approved
0.7939 Intermediate Similarity NPD3051 Approved
0.7888 Intermediate Similarity NPD7298 Approved
0.7879 Intermediate Similarity NPD6107 Approved
0.7852 Intermediate Similarity NPD5718 Phase 2
0.7852 Intermediate Similarity NPD3145 Approved
0.7852 Intermediate Similarity NPD3144 Approved
0.7834 Intermediate Similarity NPD2421 Approved
0.7834 Intermediate Similarity NPD2420 Approved
0.7806 Intermediate Similarity NPD5177 Phase 3
0.7791 Intermediate Similarity NPD7312 Approved
0.7791 Intermediate Similarity NPD7310 Approved
0.7791 Intermediate Similarity NPD7311 Approved
0.7791 Intermediate Similarity NPD7313 Approved
0.7778 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD3845 Phase 1
0.7746 Intermediate Similarity NPD7309 Approved
0.7727 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD2161 Phase 2
0.7718 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD7906 Approved
0.7692 Intermediate Similarity NPD3060 Approved
0.7688 Intermediate Similarity NPD4577 Approved
0.7688 Intermediate Similarity NPD4578 Approved
0.7662 Intermediate Similarity NPD1753 Discontinued
0.7658 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD2978 Approved
0.7622 Intermediate Similarity NPD2977 Approved
0.7619 Intermediate Similarity NPD4166 Phase 2
0.761 Intermediate Similarity NPD3124 Discontinued
0.7602 Intermediate Similarity NPD5313 Approved
0.7602 Intermediate Similarity NPD5312 Approved
0.7602 Intermediate Similarity NPD8156 Discontinued
0.758 Intermediate Similarity NPD4237 Approved
0.758 Intermediate Similarity NPD4236 Phase 3
0.758 Intermediate Similarity NPD4162 Approved
0.7557 Intermediate Similarity NPD4663 Approved
0.7544 Intermediate Similarity NPD8099 Discontinued
0.7544 Intermediate Similarity NPD8252 Approved
0.7544 Intermediate Similarity NPD8251 Approved
0.753 Intermediate Similarity NPD6788 Approved
0.7529 Intermediate Similarity NPD4481 Phase 3
0.7528 Intermediate Similarity NPD2488 Approved
0.7528 Intermediate Similarity NPD2490 Approved
0.7516 Intermediate Similarity NPD2238 Phase 2
0.7515 Intermediate Similarity NPD5773 Approved
0.7515 Intermediate Similarity NPD5772 Approved
0.7514 Intermediate Similarity NPD6297 Approved
0.7486 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD824 Approved
0.7485 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6895 Approved
0.7484 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6896 Approved
0.747 Intermediate Similarity NPD5977 Approved
0.747 Intermediate Similarity NPD5978 Approved
0.7466 Intermediate Similarity NPD2668 Approved
0.7466 Intermediate Similarity NPD2667 Approved
0.7456 Intermediate Similarity NPD7802 Discontinued
0.7453 Intermediate Similarity NPD1424 Approved
0.7443 Intermediate Similarity NPD6851 Approved
0.7443 Intermediate Similarity NPD6853 Approved
0.7432 Intermediate Similarity NPD2233 Approved
0.7432 Intermediate Similarity NPD2232 Approved
0.7432 Intermediate Similarity NPD2230 Approved
0.7425 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD6331 Phase 2
0.7419 Intermediate Similarity NPD823 Approved
0.7419 Intermediate Similarity NPD817 Approved
0.7378 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD3692 Discontinued
0.7342 Intermediate Similarity NPD3656 Approved
0.7342 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD4474 Approved
0.7338 Intermediate Similarity NPD4475 Approved
0.7312 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD6090 Discontinued
0.7296 Intermediate Similarity NPD7153 Discontinued
0.729 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD3109 Approved
0.729 Intermediate Similarity NPD3110 Approved
0.729 Intermediate Similarity NPD3620 Phase 2
0.7285 Intermediate Similarity NPD3055 Approved
0.7285 Intermediate Similarity NPD3053 Approved
0.7273 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD6687 Approved
0.7267 Intermediate Similarity NPD6688 Approved
0.7248 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD4123 Phase 3
0.7238 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD1375 Discontinued
0.7226 Intermediate Similarity NPD1136 Approved
0.7226 Intermediate Similarity NPD1130 Approved
0.7226 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD1132 Approved
0.7219 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD4210 Discontinued
0.7203 Intermediate Similarity NPD228 Approved
0.72 Intermediate Similarity NPD4873 Discontinued
0.7191 Intermediate Similarity NPD7280 Phase 3
0.7191 Intermediate Similarity NPD7281 Phase 3
0.719 Intermediate Similarity NPD3635 Approved
0.719 Intermediate Similarity NPD3636 Approved
0.719 Intermediate Similarity NPD3637 Approved
0.7188 Intermediate Similarity NPD7037 Approved
0.7186 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7110 Phase 1
0.7176 Intermediate Similarity NPD5604 Discontinued
0.7174 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD4103 Phase 2
0.7171 Intermediate Similarity NPD4098 Discontinued
0.7169 Intermediate Similarity NPD4005 Discontinued
0.7169 Intermediate Similarity NPD3866 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD3450 Approved
0.7166 Intermediate Similarity NPD2493 Approved
0.7166 Intermediate Similarity NPD2494 Approved
0.7166 Intermediate Similarity NPD3452 Approved
0.7162 Intermediate Similarity NPD4093 Discontinued
0.7161 Intermediate Similarity NPD598 Approved
0.7161 Intermediate Similarity NPD601 Approved
0.7161 Intermediate Similarity NPD597 Approved
0.716 Intermediate Similarity NPD5160 Discontinued
0.716 Intermediate Similarity NPD2677 Approved
0.716 Intermediate Similarity NPD5967 Approved
0.7152 Intermediate Similarity NPD2122 Discontinued
0.7143 Intermediate Similarity NPD4040 Phase 1
0.7135 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD6584 Phase 3
0.7117 Intermediate Similarity NPD7124 Phase 2
0.7115 Intermediate Similarity NPD3530 Approved
0.7115 Intermediate Similarity NPD3532 Approved
0.7115 Intermediate Similarity NPD3531 Approved
0.7114 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD5311 Approved
0.7105 Intermediate Similarity NPD5310 Approved
0.7099 Intermediate Similarity NPD6748 Discontinued
0.7095 Intermediate Similarity NPD2968 Approved
0.7095 Intermediate Similarity NPD2971 Approved
0.7093 Intermediate Similarity NPD2904 Discontinued
0.7091 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD7526 Approved
0.7091 Intermediate Similarity NPD52 Approved
0.7089 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD2492 Phase 1
0.7081 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD5582 Discontinued
0.7076 Intermediate Similarity NPD4055 Discovery
0.707 Intermediate Similarity NPD3059 Approved
0.707 Intermediate Similarity NPD3061 Approved
0.707 Intermediate Similarity NPD3062 Approved
0.7063 Intermediate Similarity NPD3156 Discontinued
0.7062 Intermediate Similarity NPD7479 Phase 2
0.7053 Intermediate Similarity NPD4583 Approved
0.7053 Intermediate Similarity NPD4582 Approved
0.7051 Intermediate Similarity NPD1039 Discontinued
0.7048 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5720 Discontinued
0.7039 Intermediate Similarity NPD4659 Approved
0.7039 Intermediate Similarity NPD1669 Approved
0.7037 Intermediate Similarity NPD3448 Approved
0.7037 Intermediate Similarity NPD2491 Approved
0.7033 Intermediate Similarity NPD7291 Discontinued
0.7032 Intermediate Similarity NPD3594 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