Structure

Physi-Chem Properties

Molecular Weight:  299.15
Volume:  315.764
LogP:  2.186
LogD:  2.787
LogS:  -1.809
# 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:  2.705
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:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.603
MDCK Permeability:  1.2755574061884545e-05
Pgp-inhibitor:  0.013
Pgp-substrate:  0.112
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.921
30% Bioavailability (F30%):  0.209

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.972
Plasma Protein Binding (PPB):  67.5562744140625%
Volume Distribution (VD):  2.116
Pgp-substrate:  24.630699157714844%

ADMET: Metabolism

CYP1A2-inhibitor:  0.261
CYP1A2-substrate:  0.958
CYP2C19-inhibitor:  0.192
CYP2C19-substrate:  0.853
CYP2C9-inhibitor:  0.028
CYP2C9-substrate:  0.786
CYP2D6-inhibitor:  0.678
CYP2D6-substrate:  0.931
CYP3A4-inhibitor:  0.019
CYP3A4-substrate:  0.855

ADMET: Excretion

Clearance (CL):  17.226
Half-life (T1/2):  0.871

ADMET: Toxicity

hERG Blockers:  0.584
Human Hepatotoxicity (H-HT):  0.174
Drug-inuced Liver Injury (DILI):  0.046
AMES Toxicity:  0.306
Rat Oral Acute Toxicity:  0.575
Maximum Recommended Daily Dose:  0.912
Skin Sensitization:  0.917
Carcinogencity:  0.097
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.691

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

  Natural Product: NPC321505

Natural Product ID:  NPC321505
Common Name*:   Methyl Coclaurine
IUPAC Name:   1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
Synonyms:   DL-N-methylcoclaurine
Standard InCHIKey:  BOKVLBSSPUTWLV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3
SMILES:  CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL453292
PubChem CID:   2752274
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
NPO27912 Cocculus laurifolius Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27912 Cocculus laurifolius Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27912 Cocculus laurifolius Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27912 Cocculus laurifolius Species Menispermaceae 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
NPT20967 CELL-LINE Platelet n.a. Activity = 73.6 % PMID[554075]
NPT20967 CELL-LINE Platelet n.a. Activity = 13.8 % PMID[554075]
NPT20967 CELL-LINE Platelet n.a. Activity = 24.8 % PMID[554075]
NPT20967 CELL-LINE Platelet n.a. Activity = 75.7 % PMID[554075]
NPT177 Tissue Aorta Rattus norvegicus Activity = 70.8 % PMID[554075]
NPT177 Tissue Aorta Rattus norvegicus Activity = 149.6 % PMID[554075]
NPT177 Tissue Aorta Rattus norvegicus Activity = 106.6 % PMID[554075]
NPT968 Protein Family Adrenergic receptor alpha-1 Rattus norvegicus Ki = 2344.23 nM PMID[554076]
NPT2685 Protein Family Voltage-gated L-type calcium channel Rattus norvegicus Ki = 22908.68 nM PMID[554076]
NPT177 Tissue Aorta Rattus norvegicus IC50 = 24547.09 nM PMID[554076]
NPT177 Tissue Aorta Rattus norvegicus IC50 = 67608.3 nM PMID[554076]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 94.46 % PMID[554077]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 96.63 % PMID[554077]

☑ 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 NPC321505 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 NPC179825
1.0 High Similarity NPC191376
0.9928 High Similarity NPC24233
0.9928 High Similarity NPC147390
0.9928 High Similarity NPC246587
0.9928 High Similarity NPC428
0.9928 High Similarity NPC135538
0.9928 High Similarity NPC476571
0.9855 High Similarity NPC185838
0.9716 High Similarity NPC477565
0.9716 High Similarity NPC103379
0.9648 High Similarity NPC88249
0.9648 High Similarity NPC220858
0.9648 High Similarity NPC97221
0.9648 High Similarity NPC151895
0.9648 High Similarity NPC192768
0.958 High Similarity NPC277669
0.958 High Similarity NPC76213
0.9574 High Similarity NPC476151
0.9517 High Similarity NPC276588
0.9517 High Similarity NPC193949
0.9517 High Similarity NPC184026
0.9517 High Similarity NPC2413
0.9517 High Similarity NPC5238
0.9517 High Similarity NPC39701
0.9517 High Similarity NPC295691
0.9517 High Similarity NPC189266
0.9517 High Similarity NPC110416
0.9517 High Similarity NPC249797
0.9517 High Similarity NPC54379
0.9517 High Similarity NPC204828
0.9517 High Similarity NPC278799
0.9517 High Similarity NPC207757
0.9517 High Similarity NPC172765
0.9517 High Similarity NPC469817
0.9517 High Similarity NPC127674
0.9493 High Similarity NPC314682
0.9441 High Similarity NPC207824
0.9441 High Similarity NPC60538
0.9424 High Similarity NPC474915
0.9424 High Similarity NPC328750
0.9424 High Similarity NPC188163
0.9424 High Similarity NPC213206
0.9315 High Similarity NPC477564
0.9315 High Similarity NPC2295
0.9275 High Similarity NPC131204
0.9275 High Similarity NPC301050
0.9262 High Similarity NPC166014
0.9262 High Similarity NPC27410
0.9247 High Similarity NPC82285
0.9247 High Similarity NPC133011
0.9195 High Similarity NPC111485
0.9189 High Similarity NPC147091
0.9155 High Similarity NPC128019
0.9155 High Similarity NPC476567
0.9155 High Similarity NPC136860
0.9091 High Similarity NPC294249
0.9079 High Similarity NPC238530
0.9079 High Similarity NPC232514
0.9079 High Similarity NPC276944
0.9034 High Similarity NPC210437
0.9034 High Similarity NPC476144
0.9034 High Similarity NPC106295
0.9034 High Similarity NPC51957
0.9034 High Similarity NPC16107
0.902 High Similarity NPC240841
0.902 High Similarity NPC256012
0.902 High Similarity NPC42549
0.902 High Similarity NPC264850
0.902 High Similarity NPC13916
0.902 High Similarity NPC268503
0.902 High Similarity NPC250846
0.902 High Similarity NPC317272
0.9013 High Similarity NPC324144
0.8986 High Similarity NPC37272
0.898 High Similarity NPC274026
0.8973 High Similarity NPC475959
0.8973 High Similarity NPC7467
0.8961 High Similarity NPC81218
0.8961 High Similarity NPC306555
0.8961 High Similarity NPC158376
0.8961 High Similarity NPC145832
0.8961 High Similarity NPC117188
0.8961 High Similarity NPC12053
0.8961 High Similarity NPC205421
0.8961 High Similarity NPC474931
0.8954 High Similarity NPC306843
0.8954 High Similarity NPC78222
0.8954 High Similarity NPC13504
0.8954 High Similarity NPC284183
0.8954 High Similarity NPC253043
0.8954 High Similarity NPC136508
0.8954 High Similarity NPC96603
0.8954 High Similarity NPC4138
0.8954 High Similarity NPC24465
0.8954 High Similarity NPC121275
0.8954 High Similarity NPC196447
0.8954 High Similarity NPC477563
0.8954 High Similarity NPC212794
0.8933 High Similarity NPC186063
0.8903 High Similarity NPC204908
0.8903 High Similarity NPC83198
0.8896 High Similarity NPC81247
0.8896 High Similarity NPC35627
0.8896 High Similarity NPC476573
0.8889 High Similarity NPC1229
0.8882 High Similarity NPC205167
0.8882 High Similarity NPC249274
0.8859 High Similarity NPC26601
0.8841 High Similarity NPC160193
0.8839 High Similarity NPC210140
0.8824 High Similarity NPC60186
0.8792 High Similarity NPC81733
0.8792 High Similarity NPC326316
0.8782 High Similarity NPC66573
0.8767 High Similarity NPC130926
0.875 High Similarity NPC475326
0.8741 High Similarity NPC170170
0.8741 High Similarity NPC219233
0.8741 High Similarity NPC211468
0.8734 High Similarity NPC190783
0.8734 High Similarity NPC152680
0.8734 High Similarity NPC232386
0.8726 High Similarity NPC168753
0.8726 High Similarity NPC109925
0.8726 High Similarity NPC118274
0.8718 High Similarity NPC298979
0.871 High Similarity NPC134858
0.8696 High Similarity NPC172403
0.8681 High Similarity NPC323123
0.8671 High Similarity NPC475215
0.8671 High Similarity NPC193528
0.8671 High Similarity NPC253429
0.8671 High Similarity NPC239775
0.8671 High Similarity NPC108434
0.8667 High Similarity NPC476568
0.8662 High Similarity NPC470324
0.8658 High Similarity NPC92541
0.8658 High Similarity NPC219162
0.8645 High Similarity NPC233650
0.8618 High Similarity NPC138487
0.8618 High Similarity NPC41178
0.8618 High Similarity NPC216459
0.8616 High Similarity NPC477020
0.8616 High Similarity NPC66341
0.8616 High Similarity NPC192135
0.8609 High Similarity NPC233029
0.8609 High Similarity NPC210148
0.8608 High Similarity NPC477562
0.8608 High Similarity NPC69712
0.8608 High Similarity NPC26240
0.8571 High Similarity NPC114364
0.8571 High Similarity NPC320223
0.8571 High Similarity NPC59028
0.8571 High Similarity NPC92191
0.8562 High Similarity NPC247639
0.8562 High Similarity NPC128560
0.8562 High Similarity NPC25084
0.8562 High Similarity NPC199465
0.8562 High Similarity NPC229166
0.8562 High Similarity NPC146288
0.8535 High Similarity NPC124657
0.8523 High Similarity NPC253883
0.8523 High Similarity NPC95075
0.8523 High Similarity NPC90844
0.8523 High Similarity NPC144863
0.8519 High Similarity NPC32154
0.8516 High Similarity NPC226428
0.8516 High Similarity NPC215829
0.8516 High Similarity NPC97072
0.8506 High Similarity NPC476572
0.8497 Intermediate Similarity NPC325871
0.8497 Intermediate Similarity NPC80129
0.8497 Intermediate Similarity NPC187022
0.8497 Intermediate Similarity NPC99659
0.8481 Intermediate Similarity NPC150879
0.8471 Intermediate Similarity NPC3375
0.8471 Intermediate Similarity NPC255607
0.8467 Intermediate Similarity NPC130941
0.8466 Intermediate Similarity NPC286119
0.8442 Intermediate Similarity NPC126519
0.8442 Intermediate Similarity NPC31311
0.8442 Intermediate Similarity NPC234392
0.8442 Intermediate Similarity NPC203784
0.8442 Intermediate Similarity NPC170503
0.8438 Intermediate Similarity NPC476331
0.8421 Intermediate Similarity NPC476579
0.8415 Intermediate Similarity NPC8836
0.8415 Intermediate Similarity NPC15414
0.8415 Intermediate Similarity NPC328155
0.8415 Intermediate Similarity NPC271013
0.8415 Intermediate Similarity NPC251735
0.8415 Intermediate Similarity NPC42663
0.8415 Intermediate Similarity NPC7715
0.8415 Intermediate Similarity NPC279228
0.8415 Intermediate Similarity NPC54654
0.8415 Intermediate Similarity NPC285931
0.8415 Intermediate Similarity NPC104196
0.8415 Intermediate Similarity NPC182052
0.8415 Intermediate Similarity NPC239824

  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 NPC321505 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
0.9424 High Similarity NPD4664 Clinical (unspecified phase)
0.9034 High Similarity NPD4584 Approved
0.8896 High Similarity NPD4010 Discontinued
0.8792 High Similarity NPD4017 Approved
0.8699 High Similarity NPD5241 Discontinued
0.8675 High Similarity NPD4773 Phase 2
0.8675 High Similarity NPD4772 Phase 2
0.8662 High Similarity NPD2898 Approved
0.8645 High Similarity NPD7201 Clinical (unspecified phase)
0.8533 High Similarity NPD3641 Approved
0.8533 High Similarity NPD3640 Phase 3
0.8533 High Similarity NPD3639 Approved
0.8523 High Similarity NPD1754 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD7298 Approved
0.8456 Intermediate Similarity NPD2421 Approved
0.8456 Intermediate Similarity NPD2420 Approved
0.8442 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD8054 Approved
0.8415 Intermediate Similarity NPD8053 Approved
0.8411 Intermediate Similarity NPD6030 Approved
0.8411 Intermediate Similarity NPD6031 Approved
0.8397 Intermediate Similarity NPD7831 Phase 2
0.8397 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD7833 Phase 2
0.8389 Intermediate Similarity NPD3845 Phase 1
0.838 Intermediate Similarity NPD5718 Phase 2
0.8322 Intermediate Similarity NPD2674 Phase 3
0.8313 Intermediate Similarity NPD27 Approved
0.8313 Intermediate Similarity NPD2489 Approved
0.831 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.8267 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.8163 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.8163 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD2969 Approved
0.8137 Intermediate Similarity NPD2970 Approved
0.8125 Intermediate Similarity NPD3144 Approved
0.8125 Intermediate Similarity NPD3145 Approved
0.8112 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.8108 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD6071 Discontinued
0.8075 Intermediate Similarity NPD3051 Approved
0.8067 Intermediate Similarity NPD5177 Phase 3
0.8061 Intermediate Similarity NPD6297 Approved
0.8038 Intermediate Similarity NPD2563 Approved
0.8038 Intermediate Similarity NPD2560 Approved
0.8037 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD8099 Discontinued
0.7988 Intermediate Similarity NPD8252 Approved
0.7988 Intermediate Similarity NPD8251 Approved
0.7987 Intermediate Similarity NPD6788 Approved
0.7974 Intermediate Similarity NPD3124 Discontinued
0.7973 Intermediate Similarity NPD6895 Approved
0.7973 Intermediate Similarity NPD6896 Approved
0.7947 Intermediate Similarity NPD3060 Approved
0.7939 Intermediate Similarity NPD8156 Discontinued
0.7919 Intermediate Similarity NPD1753 Discontinued
0.7902 Intermediate Similarity NPD3053 Approved
0.7902 Intermediate Similarity NPD3055 Approved
0.7901 Intermediate Similarity NPD6107 Approved
0.7901 Intermediate Similarity NPD7802 Discontinued
0.787 Intermediate Similarity NPD6851 Approved
0.787 Intermediate Similarity NPD6853 Approved
0.7862 Intermediate Similarity NPD2978 Approved
0.7862 Intermediate Similarity NPD2977 Approved
0.7853 Intermediate Similarity NPD4166 Phase 2
0.7843 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD7906 Approved
0.7834 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD5978 Approved
0.7812 Intermediate Similarity NPD5977 Approved
0.7811 Intermediate Similarity NPD7311 Approved
0.7811 Intermediate Similarity NPD4577 Approved
0.7811 Intermediate Similarity NPD7312 Approved
0.7811 Intermediate Similarity NPD7310 Approved
0.7811 Intermediate Similarity NPD7313 Approved
0.7811 Intermediate Similarity NPD4578 Approved
0.7811 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD3110 Approved
0.777 Intermediate Similarity NPD3109 Approved
0.7765 Intermediate Similarity NPD7309 Approved
0.7755 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD2667 Approved
0.773 Intermediate Similarity NPD2668 Approved
0.7727 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD824 Approved
0.7712 Intermediate Similarity NPD4162 Approved
0.7703 Intermediate Similarity NPD4474 Approved
0.7703 Intermediate Similarity NPD4475 Approved
0.7692 Intermediate Similarity NPD2230 Approved
0.7692 Intermediate Similarity NPD2232 Approved
0.7692 Intermediate Similarity NPD2233 Approved
0.7674 Intermediate Similarity NPD4663 Approved
0.7671 Intermediate Similarity NPD3636 Approved
0.7671 Intermediate Similarity NPD3637 Approved
0.7671 Intermediate Similarity NPD3635 Approved
0.766 Intermediate Similarity NPD4093 Discontinued
0.7654 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD2488 Approved
0.7644 Intermediate Similarity NPD2490 Approved
0.7625 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD7110 Phase 1
0.7619 Intermediate Similarity NPD5312 Approved
0.7619 Intermediate Similarity NPD5313 Approved
0.7613 Intermediate Similarity NPD3692 Discontinued
0.761 Intermediate Similarity NPD4005 Discontinued
0.7607 Intermediate Similarity NPD4055 Discovery
0.7597 Intermediate Similarity NPD4236 Phase 3
0.7597 Intermediate Similarity NPD4237 Approved
0.7586 Intermediate Similarity NPD5310 Approved
0.7586 Intermediate Similarity NPD5311 Approved
0.7582 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD4123 Phase 3
0.758 Intermediate Similarity NPD1424 Approved
0.7571 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD5155 Approved
0.7568 Intermediate Similarity NPD5156 Approved
0.7564 Intermediate Similarity NPD7124 Phase 2
0.755 Intermediate Similarity NPD823 Approved
0.755 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD817 Approved
0.7548 Intermediate Similarity NPD6331 Phase 2
0.7548 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD4481 Phase 3
0.7533 Intermediate Similarity NPD2238 Phase 2
0.7532 Intermediate Similarity NPD6090 Discontinued
0.7517 Intermediate Similarity NPD1669 Approved
0.75 Intermediate Similarity NPD3594 Approved
0.75 Intermediate Similarity NPD2605 Approved
0.75 Intermediate Similarity NPD7281 Phase 3
0.75 Intermediate Similarity NPD2606 Approved
0.75 Intermediate Similarity NPD7280 Phase 3
0.75 Intermediate Similarity NPD5604 Discontinued
0.75 Intermediate Similarity NPD3595 Approved
0.7485 Intermediate Similarity NPD6687 Approved
0.7485 Intermediate Similarity NPD6688 Approved
0.7484 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6584 Phase 3
0.7483 Intermediate Similarity NPD7905 Discontinued
0.7467 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD228 Approved
0.7436 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD6748 Discontinued
0.7429 Intermediate Similarity NPD7291 Discontinued
0.7423 Intermediate Similarity NPD5773 Approved
0.7423 Intermediate Similarity NPD5772 Approved
0.7421 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD7037 Approved
0.7419 Intermediate Similarity NPD7153 Discontinued
0.7415 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD4098 Discontinued
0.7415 Intermediate Similarity NPD4103 Phase 2
0.7403 Intermediate Similarity NPD2161 Phase 2
0.7399 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD4659 Approved
0.7389 Intermediate Similarity NPD5160 Discontinued
0.7381 Intermediate Similarity NPD4083 Discontinued
0.7375 Intermediate Similarity NPD2122 Discontinued
0.7372 Intermediate Similarity NPD6364 Approved
0.7372 Intermediate Similarity NPD44 Approved
0.7368 Intermediate Similarity NPD3920 Phase 2
0.7368 Intermediate Similarity NPD7479 Phase 2
0.7362 Intermediate Similarity NPD5720 Discontinued
0.7362 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD5283 Phase 1
0.7355 Intermediate Similarity NPD3656 Approved
0.7351 Intermediate Similarity NPD1130 Approved
0.7351 Intermediate Similarity NPD1136 Approved
0.7351 Intermediate Similarity NPD1132 Approved
0.7346 Intermediate Similarity NPD4678 Approved
0.7346 Intermediate Similarity NPD6876 Approved
0.7346 Intermediate Similarity NPD6875 Approved
0.7346 Intermediate Similarity NPD4675 Approved
0.7345 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD5303 Approved
0.7343 Intermediate Similarity NPD5304 Approved
0.7341 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD4873 Discontinued
0.7305 Intermediate Similarity NPD5677 Discontinued
0.7303 Intermediate Similarity NPD3620 Phase 2
0.7303 Intermediate Similarity NPD3062 Approved
0.7303 Intermediate Similarity NPD3061 Approved
0.7303 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD3059 Approved
0.7296 Intermediate Similarity NPD7598 Phase 2
0.7285 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD598 Approved
0.7285 Intermediate Similarity NPD597 Approved
0.7285 Intermediate Similarity NPD601 Approved
0.7284 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD6582 Phase 2
0.7279 Intermediate Similarity NPD1420 Approved
0.7279 Intermediate Similarity NPD6583 Phase 3
0.7279 Intermediate Similarity NPD1421 Approved
0.7268 Intermediate Similarity NPD2494 Approved
0.7268 Intermediate Similarity NPD3452 Approved
0.7268 Intermediate Similarity NPD3450 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