Structure

Physi-Chem Properties

Molecular Weight:  299.15
Volume:  315.764
LogP:  2.263
LogD:  2.428
LogS:  -2.173
# Rotatable Bonds:  3
TPSA:  52.93
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.915
Synthetic Accessibility Score:  2.775
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.705
MDCK Permeability:  1.72E-05
Pgp-inhibitor:  0.014
Pgp-substrate:  0.96
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.893
30% Bioavailability (F30%):  0.177

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.986
Plasma Protein Binding (PPB):  70.21%
Volume Distribution (VD):  2.369
Pgp-substrate:  20.99%

ADMET: Metabolism

CYP1A2-inhibitor:  0.234
CYP1A2-substrate:  0.966
CYP2C19-inhibitor:  0.374
CYP2C19-substrate:  0.904
CYP2C9-inhibitor:  0.117
CYP2C9-substrate:  0.799
CYP2D6-inhibitor:  0.726
CYP2D6-substrate:  0.925
CYP3A4-inhibitor:  0.032
CYP3A4-substrate:  0.9

ADMET: Excretion

Clearance (CL):  18.028
Half-life (T1/2):  0.882

ADMET: Toxicity

hERG Blockers:  0.391
Human Hepatotoxicity (H-HT):  0.299
Drug-inuced Liver Injury (DILI):  0.137
AMES Toxicity:  0.12
Rat Oral Acute Toxicity:  0.83
Maximum Recommended Daily Dose:  0.951
Skin Sensitization:  0.915
Carcinogencity:  0.367
Eye Corrosion:  0.003
Eye Irritation:  0.015
Respiratory Toxicity:  0.852

Download Data

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

  Natural Product: NPC477565

Natural Product ID:  NPC477565
Common Name*:   (1S)-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-8-ol;2,2,2-trifluoroacetic acid
IUPAC Name:   (1S)-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-8-ol;2,2,2-trifluoroacetic acid
Synonyms:   (1S)-Juziphine
Standard InCHIKey:  KBUDZZRXWSJABG-RSAXXLAASA-N
Standard InCHI:  InChI=1S/C18H21NO3.C2HF3O2/c1-19-10-9-13-5-8-16(22-2)18(21)17(13)15(19)11-12-3-6-14(20)7-4-12;3-2(4,5)1(6)7/h3-8,15,20-21H,9-11H2,1-2H3;(H,6,7)/t15-;/m0./s1
SMILES:  CN1CCC2=C([C@@H]1CC3=CC=C(C=C3)O)C(=C(C=C2)OC)O.C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   54579939
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives
        • [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO11152 Neolitsea dealbata Species Lauraceae Eukaryota Barks Thomas Road, 1.5km West of Yungaburra, Australia 1998-MAY PMID[20732809]
NPO11152 Neolitsea dealbata Species Lauraceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 100000 nM PMID[20732809]
NPT165 Cell Line HeLa Homo sapiens IC50 > 100000 nM PMID[20732809]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 100000 nM PMID[20732809]
NPT858 Cell Line LNCaP Homo sapiens IC50 > 100000 nM PMID[20732809]
NPT306 Cell Line PC-3 Homo sapiens IC50 > 100000 nM PMID[20732809]
NPT1523 Cell Line NFF Homo sapiens IC50 > 100000 nM PMID[20732809]
NPT27 Others Unspecified IC50 > 100000 nM PMID[20732809]

☑ 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 NPC477565 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 NPC103379
0.9857 High Similarity NPC476151
0.9716 High Similarity NPC191376
0.9716 High Similarity NPC179825
0.9716 High Similarity NPC321505
0.9655 High Similarity NPC54379
0.9655 High Similarity NPC204828
0.9655 High Similarity NPC172765
0.9655 High Similarity NPC193949
0.9655 High Similarity NPC207757
0.9655 High Similarity NPC5238
0.9655 High Similarity NPC189266
0.9655 High Similarity NPC110416
0.9655 High Similarity NPC469817
0.9655 High Similarity NPC276588
0.9655 High Similarity NPC295691
0.9655 High Similarity NPC39701
0.9655 High Similarity NPC2413
0.9655 High Similarity NPC127674
0.9655 High Similarity NPC278799
0.9655 High Similarity NPC249797
0.9655 High Similarity NPC184026
0.9648 High Similarity NPC476571
0.9648 High Similarity NPC147390
0.9648 High Similarity NPC246587
0.9648 High Similarity NPC135538
0.9648 High Similarity NPC428
0.9648 High Similarity NPC24233
0.9586 High Similarity NPC477564
0.9586 High Similarity NPC2295
0.9574 High Similarity NPC185838
0.9379 High Similarity NPC220858
0.9379 High Similarity NPC88249
0.9379 High Similarity NPC97221
0.9379 High Similarity NPC192768
0.9379 High Similarity NPC151895
0.9315 High Similarity NPC277669
0.9315 High Similarity NPC76213
0.9267 High Similarity NPC166014
0.9267 High Similarity NPC27410
0.922 High Similarity NPC314682
0.9211 High Similarity NPC238530
0.9211 High Similarity NPC276944
0.9211 High Similarity NPC232514
0.9178 High Similarity NPC207824
0.9178 High Similarity NPC60538
0.9172 High Similarity NPC210437
0.9172 High Similarity NPC16107
0.9172 High Similarity NPC51957
0.9172 High Similarity NPC106295
0.9172 High Similarity NPC476144
0.9155 High Similarity NPC188163
0.9155 High Similarity NPC213206
0.9155 High Similarity NPC328750
0.9155 High Similarity NPC474915
0.915 High Similarity NPC264850
0.915 High Similarity NPC13916
0.9143 High Similarity NPC131204
0.9143 High Similarity NPC301050
0.9122 High Similarity NPC82285
0.9122 High Similarity NPC133011
0.911 High Similarity NPC7467
0.9085 High Similarity NPC24465
0.9079 High Similarity NPC60186
0.9067 High Similarity NPC147091
0.9032 High Similarity NPC83198
0.9032 High Similarity NPC204908
0.902 High Similarity NPC324144
0.8968 High Similarity NPC81218
0.8968 High Similarity NPC306555
0.8968 High Similarity NPC158376
0.8968 High Similarity NPC117188
0.8968 High Similarity NPC145832
0.8968 High Similarity NPC205421
0.8968 High Similarity NPC474931
0.8968 High Similarity NPC12053
0.8961 High Similarity NPC136508
0.8961 High Similarity NPC306843
0.8961 High Similarity NPC196447
0.8961 High Similarity NPC477563
0.8961 High Similarity NPC96603
0.8961 High Similarity NPC212794
0.8961 High Similarity NPC78222
0.8961 High Similarity NPC13504
0.8961 High Similarity NPC253043
0.8947 High Similarity NPC111485
0.8903 High Similarity NPC476573
0.8903 High Similarity NPC81247
0.8903 High Similarity NPC35627
0.8897 High Similarity NPC476567
0.8897 High Similarity NPC136860
0.8897 High Similarity NPC128019
0.8896 High Similarity NPC1229
0.8861 High Similarity NPC152680
0.8861 High Similarity NPC232386
0.8861 High Similarity NPC190783
0.8859 High Similarity NPC274026
0.8836 High Similarity NPC294249
0.8816 High Similarity NPC186063
0.88 High Similarity NPC326316
0.88 High Similarity NPC81733
0.8782 High Similarity NPC250846
0.8782 High Similarity NPC268503
0.8782 High Similarity NPC240841
0.8782 High Similarity NPC317272
0.8782 High Similarity NPC42549
0.8782 High Similarity NPC256012
0.8766 High Similarity NPC249274
0.8766 High Similarity NPC205167
0.875 High Similarity NPC216459
0.875 High Similarity NPC138487
0.875 High Similarity NPC41178
0.8742 High Similarity NPC37272
0.8742 High Similarity NPC26601
0.8734 High Similarity NPC118274
0.8734 High Similarity NPC168753
0.8726 High Similarity NPC210140
0.8726 High Similarity NPC298979
0.8725 High Similarity NPC475959
0.8718 High Similarity NPC284183
0.8718 High Similarity NPC4138
0.8718 High Similarity NPC121275
0.8714 High Similarity NPC160193
0.8693 High Similarity NPC146288
0.8679 High Similarity NPC239775
0.8671 High Similarity NPC470324
0.8649 High Similarity NPC130926
0.8642 High Similarity NPC32154
0.8636 High Similarity NPC475326
0.8625 High Similarity NPC477020
0.8625 High Similarity NPC66341
0.8625 High Similarity NPC192135
0.8616 High Similarity NPC69712
0.8616 High Similarity NPC477562
0.8616 High Similarity NPC26240
0.8599 High Similarity NPC134858
0.858 High Similarity NPC320223
0.858 High Similarity NPC114364
0.8571 High Similarity NPC172403
0.8571 High Similarity NPC128560
0.8571 High Similarity NPC199465
0.8571 High Similarity NPC229166
0.8571 High Similarity NPC234392
0.8571 High Similarity NPC31311
0.8553 High Similarity NPC66573
0.8552 High Similarity NPC193528
0.8544 High Similarity NPC124657
0.8543 High Similarity NPC219162
0.8543 High Similarity NPC92541
0.8537 High Similarity NPC181796
0.8537 High Similarity NPC279228
0.8537 High Similarity NPC7715
0.8537 High Similarity NPC15414
0.8537 High Similarity NPC54654
0.8537 High Similarity NPC285931
0.8537 High Similarity NPC223690
0.8537 High Similarity NPC8836
0.8537 High Similarity NPC182052
0.8537 High Similarity NPC311973
0.8537 High Similarity NPC239824
0.8537 High Similarity NPC42663
0.8537 High Similarity NPC229373
0.8537 High Similarity NPC290582
0.8537 High Similarity NPC251735
0.8537 High Similarity NPC290005
0.8537 High Similarity NPC104196
0.8537 High Similarity NPC217748
0.8537 High Similarity NPC222661
0.8537 High Similarity NPC258657
0.8537 High Similarity NPC185639
0.8537 High Similarity NPC49075
0.8537 High Similarity NPC271013
0.8537 High Similarity NPC90998
0.8537 High Similarity NPC328155
0.8535 High Similarity NPC233650
0.8519 High Similarity NPC241704
0.8516 High Similarity NPC476572
0.8509 High Similarity NPC2314
0.8506 High Similarity NPC93593
0.8506 High Similarity NPC325871
0.8506 High Similarity NPC99659
0.85 High Similarity NPC109925
0.8493 Intermediate Similarity NPC170170
0.8493 Intermediate Similarity NPC211468
0.8493 Intermediate Similarity NPC219233
0.8485 Intermediate Similarity NPC254441
0.8485 Intermediate Similarity NPC274716
0.8485 Intermediate Similarity NPC167116
0.8481 Intermediate Similarity NPC3375
0.8481 Intermediate Similarity NPC255607
0.8476 Intermediate Similarity NPC286119
0.8462 Intermediate Similarity NPC59028
0.8462 Intermediate Similarity NPC92191
0.8452 Intermediate Similarity NPC203784
0.8452 Intermediate Similarity NPC170503
0.8452 Intermediate Similarity NPC126519
0.8447 Intermediate Similarity NPC475215
0.8447 Intermediate Similarity NPC476331
0.8447 Intermediate Similarity NPC108434
0.8435 Intermediate Similarity NPC323123

  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 NPC477565 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
0.9172 High Similarity NPD4584 Approved
0.9155 High Similarity NPD4664 Clinical (unspecified phase)
0.8671 High Similarity NPD2898 Approved
0.8662 High Similarity NPD4010 Discontinued
0.8562 High Similarity NPD4772 Phase 2
0.8562 High Similarity NPD4773 Phase 2
0.8553 High Similarity NPD4017 Approved
0.8537 High Similarity NPD8053 Approved
0.8537 High Similarity NPD8054 Approved
0.8533 High Similarity NPD1754 Clinical (unspecified phase)
0.8467 Intermediate Similarity NPD2421 Approved
0.8467 Intermediate Similarity NPD2420 Approved
0.8456 Intermediate Similarity NPD5241 Discontinued
0.8418 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8367 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD2489 Approved
0.8323 Intermediate Similarity NPD27 Approved
0.8301 Intermediate Similarity NPD3640 Phase 3
0.8301 Intermediate Similarity NPD3641 Approved
0.8301 Intermediate Similarity NPD3639 Approved
0.8301 Intermediate Similarity NPD6031 Approved
0.8301 Intermediate Similarity NPD6030 Approved
0.8299 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.8299 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.8291 Intermediate Similarity NPD7831 Phase 2
0.8291 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8291 Intermediate Similarity NPD7833 Phase 2
0.8269 Intermediate Similarity NPD7298 Approved
0.8264 Intermediate Similarity NPD5718 Phase 2
0.8228 Intermediate Similarity NPD6788 Approved
0.8207 Intermediate Similarity NPD2674 Phase 3
0.82 Intermediate Similarity NPD5177 Phase 3
0.8199 Intermediate Similarity NPD6071 Discontinued
0.8165 Intermediate Similarity NPD2563 Approved
0.8165 Intermediate Similarity NPD2560 Approved
0.8158 Intermediate Similarity NPD3845 Phase 1
0.8148 Intermediate Similarity NPD2969 Approved
0.8148 Intermediate Similarity NPD2970 Approved
0.811 Intermediate Similarity NPD8252 Approved
0.811 Intermediate Similarity NPD8251 Approved
0.811 Intermediate Similarity NPD8099 Discontinued
0.8086 Intermediate Similarity NPD3051 Approved
0.8069 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD8156 Discontinued
0.8039 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.8014 Intermediate Similarity NPD3145 Approved
0.8014 Intermediate Similarity NPD3144 Approved
0.8 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7974 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7959 Intermediate Similarity NPD4475 Approved
0.7959 Intermediate Similarity NPD4474 Approved
0.7867 Intermediate Similarity NPD6895 Approved
0.7867 Intermediate Similarity NPD6896 Approved
0.7857 Intermediate Similarity NPD6297 Approved
0.7849 Intermediate Similarity NPD7906 Approved
0.7843 Intermediate Similarity NPD3060 Approved
0.7832 Intermediate Similarity NPD2230 Approved
0.7832 Intermediate Similarity NPD2233 Approved
0.7832 Intermediate Similarity NPD2232 Approved
0.7831 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD7311 Approved
0.7824 Intermediate Similarity NPD4577 Approved
0.7824 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD7312 Approved
0.7824 Intermediate Similarity NPD7313 Approved
0.7824 Intermediate Similarity NPD4578 Approved
0.7824 Intermediate Similarity NPD7310 Approved
0.7821 Intermediate Similarity NPD1424 Approved
0.7815 Intermediate Similarity NPD1753 Discontinued
0.7805 Intermediate Similarity NPD7802 Discontinued
0.7805 Intermediate Similarity NPD6107 Approved
0.7793 Intermediate Similarity NPD3055 Approved
0.7793 Intermediate Similarity NPD3053 Approved
0.7778 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD7309 Approved
0.7771 Intermediate Similarity NPD6090 Discontinued
0.7756 Intermediate Similarity NPD3124 Discontinued
0.7746 Intermediate Similarity NPD2668 Approved
0.7746 Intermediate Similarity NPD2667 Approved
0.7736 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD4162 Approved
0.7716 Intermediate Similarity NPD5978 Approved
0.7716 Intermediate Similarity NPD5977 Approved
0.7712 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD4663 Approved
0.7677 Intermediate Similarity NPD6748 Discontinued
0.7677 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD6853 Approved
0.7674 Intermediate Similarity NPD6851 Approved
0.7667 Intermediate Similarity NPD2238 Phase 2
0.7667 Intermediate Similarity NPD3109 Approved
0.7667 Intermediate Similarity NPD3110 Approved
0.7657 Intermediate Similarity NPD2488 Approved
0.7657 Intermediate Similarity NPD2490 Approved
0.7654 Intermediate Similarity NPD2977 Approved
0.7654 Intermediate Similarity NPD2978 Approved
0.7651 Intermediate Similarity NPD4166 Phase 2
0.7651 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD3692 Discontinued
0.7628 Intermediate Similarity NPD5160 Discontinued
0.7625 Intermediate Similarity NPD824 Approved
0.7622 Intermediate Similarity NPD4055 Discovery
0.7613 Intermediate Similarity NPD4236 Phase 3
0.7613 Intermediate Similarity NPD4237 Approved
0.7606 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD3635 Approved
0.7568 Intermediate Similarity NPD3636 Approved
0.7568 Intermediate Similarity NPD3637 Approved
0.756 Intermediate Similarity NPD4481 Phase 3
0.7552 Intermediate Similarity NPD4093 Discontinued
0.7532 Intermediate Similarity NPD7598 Phase 2
0.7531 Intermediate Similarity NPD7110 Phase 1
0.7531 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD4873 Discontinued
0.7529 Intermediate Similarity NPD5312 Approved
0.7529 Intermediate Similarity NPD5313 Approved
0.7484 Intermediate Similarity NPD4123 Phase 3
0.7483 Intermediate Similarity NPD5310 Approved
0.7483 Intermediate Similarity NPD5304 Approved
0.7483 Intermediate Similarity NPD5303 Approved
0.7483 Intermediate Similarity NPD5311 Approved
0.7468 Intermediate Similarity NPD2155 Approved
0.7468 Intermediate Similarity NPD7124 Phase 2
0.7468 Intermediate Similarity NPD2156 Approved
0.7468 Intermediate Similarity NPD2154 Approved
0.7467 Intermediate Similarity NPD5155 Approved
0.7467 Intermediate Similarity NPD5156 Approved
0.7457 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD6331 Phase 2
0.7452 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD4098 Discontinued
0.7432 Intermediate Similarity NPD4103 Phase 2
0.7432 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD1669 Approved
0.7414 Intermediate Similarity NPD7280 Phase 3
0.7414 Intermediate Similarity NPD7281 Phase 3
0.741 Intermediate Similarity NPD5604 Discontinued
0.7407 Intermediate Similarity NPD4005 Discontinued
0.7403 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD3594 Approved
0.74 Intermediate Similarity NPD2605 Approved
0.74 Intermediate Similarity NPD2606 Approved
0.74 Intermediate Similarity NPD3595 Approved
0.7396 Intermediate Similarity NPD6687 Approved
0.7396 Intermediate Similarity NPD6688 Approved
0.7391 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD1914 Approved
0.7383 Intermediate Similarity NPD6584 Phase 3
0.7383 Intermediate Similarity NPD7905 Discontinued
0.7378 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD3656 Approved
0.7365 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD6667 Approved
0.7358 Intermediate Similarity NPD6666 Approved
0.7357 Intermediate Similarity NPD228 Approved
0.7338 Intermediate Similarity NPD823 Approved
0.7338 Intermediate Similarity NPD817 Approved
0.7333 Intermediate Similarity NPD5772 Approved
0.7333 Intermediate Similarity NPD5773 Approved
0.7325 Intermediate Similarity NPD7037 Approved
0.7325 Intermediate Similarity NPD7153 Discontinued
0.7321 Intermediate Similarity NPD4666 Phase 3
0.7321 Intermediate Similarity NPD2904 Discontinued
0.7314 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD5938 Phase 3
0.7308 Intermediate Similarity NPD2161 Phase 2
0.7297 Intermediate Similarity NPD4659 Approved
0.7296 Intermediate Similarity NPD2677 Approved
0.7294 Intermediate Similarity NPD4083 Discontinued
0.7284 Intermediate Similarity NPD5976 Discontinued
0.7284 Intermediate Similarity NPD2122 Discontinued
0.7283 Intermediate Similarity NPD3452 Approved
0.7283 Intermediate Similarity NPD2494 Approved
0.7283 Intermediate Similarity NPD3450 Approved
0.7283 Intermediate Similarity NPD2493 Approved
0.7283 Intermediate Similarity NPD7479 Phase 2
0.7279 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD44 Approved
0.7278 Intermediate Similarity NPD6364 Approved
0.7273 Intermediate Similarity NPD5720 Discontinued
0.7268 Intermediate Similarity NPD8095 Phase 1
0.7267 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD5709 Phase 3
0.726 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD6876 Approved
0.7256 Intermediate Similarity NPD4678 Approved
0.7256 Intermediate Similarity NPD6875 Approved
0.7256 Intermediate Similarity NPD4675 Approved
0.7255 Intermediate Similarity NPD3532 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