Structure

Physi-Chem Properties

Molecular Weight:  273.14
Volume:  277.888
LogP:  0.936
LogD:  1.006
LogS:  -2.078
# Rotatable Bonds:  1
TPSA:  52.93
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.762
Synthetic Accessibility Score:  4.819
Fsp3:  0.5
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:  -4.75
MDCK Permeability:  1.9585084373829886e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.842
Human Intestinal Absorption (HIA):  0.145
20% Bioavailability (F20%):  0.024
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.992
Plasma Protein Binding (PPB):  33.676055908203125%
Volume Distribution (VD):  2.459
Pgp-substrate:  68.90006256103516%

ADMET: Metabolism

CYP1A2-inhibitor:  0.107
CYP1A2-substrate:  0.763
CYP2C19-inhibitor:  0.043
CYP2C19-substrate:  0.838
CYP2C9-inhibitor:  0.022
CYP2C9-substrate:  0.466
CYP2D6-inhibitor:  0.653
CYP2D6-substrate:  0.881
CYP3A4-inhibitor:  0.043
CYP3A4-substrate:  0.55

ADMET: Excretion

Clearance (CL):  12.078
Half-life (T1/2):  0.85

ADMET: Toxicity

hERG Blockers:  0.079
Human Hepatotoxicity (H-HT):  0.139
Drug-inuced Liver Injury (DILI):  0.041
AMES Toxicity:  0.094
Rat Oral Acute Toxicity:  0.399
Maximum Recommended Daily Dose:  0.972
Skin Sensitization:  0.501
Carcinogencity:  0.855
Eye Corrosion:  0.004
Eye Irritation:  0.021
Respiratory Toxicity:  0.928

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

  Natural Product: NPC147091

Natural Product ID:  NPC147091
Common Name*:   TZTBAJFJEZRQCV-RLCCDNCMSA-N
IUPAC Name:   n.a.
Synonyms:   8-O-Demethylmaritidine
Standard InCHIKey:  TZTBAJFJEZRQCV-RLCCDNCMSA-N
Standard InCHI:  InChI=1S/C16H19NO3/c1-20-14-8-12-10(6-13(14)19)9-17-5-4-16(12)3-2-11(18)7-15(16)17/h2-3,6,8,11,15,18-19H,4-5,7,9H2,1H3/t11-,15+,16+/m1/s1
SMILES:  COc1cc2c(cc1O)CN1[C@@H]3[C@@]2(C=C[C@H](C3)O)CC1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2087242
PubChem CID:   443683
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0001908] Benzoquinolines
          • [CHEMONTID:0000100] Phenanthridines and derivatives

*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
NPO3630 Crotalaria crispata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3630 Crotalaria crispata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9485 Haplopappus deserticola Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9144 Atriplex parvifolia Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17432 Ligularia przewalskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3630 Crotalaria crispata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1412 Artemisia juncea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19776 Hesperocyparis arizonica Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11000 Eupatorium laevigatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11473 Viburnum lantana Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13181 Ferula persica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26299 Reticularia lycoperdon Species Reticulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19610 Stachys aegyptiaca Species Lamiaceae 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
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus IC50 = 57400.0 nM PMID[573645]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 91500.0 nM PMID[573644]
NPT35 Others n.a. permeability = 0.7 10'-6 cm/s PMID[573645]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 61.5 ug.mL-1 PMID[573646]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 > 90.0 ug.mL-1 PMID[573646]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 90.0 ug.mL-1 PMID[573646]

☑ 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 NPC147091 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
0.9408 High Similarity NPC205167
0.9408 High Similarity NPC249274
0.9396 High Similarity NPC82285
0.9396 High Similarity NPC133011
0.9281 High Similarity NPC215829
0.9281 High Similarity NPC97072
0.9262 High Similarity NPC274026
0.9189 High Similarity NPC321505
0.9189 High Similarity NPC179825
0.9189 High Similarity NPC191376
0.9128 High Similarity NPC147390
0.9128 High Similarity NPC246587
0.9128 High Similarity NPC135538
0.9128 High Similarity NPC428
0.9128 High Similarity NPC24233
0.9128 High Similarity NPC476571
0.9067 High Similarity NPC477565
0.9067 High Similarity NPC103379
0.9054 High Similarity NPC185838
0.902 High Similarity NPC78733
0.8938 High Similarity NPC225597
0.8938 High Similarity NPC470739
0.8938 High Similarity NPC477640
0.8933 High Similarity NPC476151
0.8931 High Similarity NPC58766
0.8931 High Similarity NPC290759
0.8931 High Similarity NPC475686
0.8931 High Similarity NPC266176
0.8931 High Similarity NPC82533
0.8931 High Similarity NPC158148
0.8926 High Similarity NPC130926
0.8903 High Similarity NPC475326
0.8896 High Similarity NPC172765
0.8896 High Similarity NPC2413
0.8896 High Similarity NPC193949
0.8896 High Similarity NPC295691
0.8896 High Similarity NPC189266
0.8896 High Similarity NPC54379
0.8896 High Similarity NPC278799
0.8896 High Similarity NPC39701
0.8896 High Similarity NPC110416
0.8896 High Similarity NPC5238
0.8896 High Similarity NPC249797
0.8896 High Similarity NPC207757
0.8896 High Similarity NPC469817
0.8896 High Similarity NPC127674
0.8896 High Similarity NPC204828
0.8896 High Similarity NPC184026
0.8896 High Similarity NPC276588
0.8882 High Similarity NPC220858
0.8882 High Similarity NPC192768
0.8882 High Similarity NPC88249
0.8882 High Similarity NPC97221
0.8882 High Similarity NPC151895
0.8875 High Similarity NPC474475
0.8868 High Similarity NPC210140
0.8868 High Similarity NPC100566
0.8846 High Similarity NPC59028
0.8846 High Similarity NPC92191
0.8824 High Similarity NPC76213
0.8824 High Similarity NPC277669
0.882 High Similarity NPC476331
0.8805 High Similarity NPC124657
0.879 High Similarity NPC18402
0.8767 High Similarity NPC131204
0.8767 High Similarity NPC301050
0.875 High Similarity NPC190332
0.875 High Similarity NPC181653
0.8742 High Similarity NPC238530
0.8742 High Similarity NPC232514
0.8742 High Similarity NPC276944
0.8742 High Similarity NPC134858
0.8726 High Similarity NPC111485
0.8716 High Similarity NPC314682
0.871 High Similarity NPC2295
0.871 High Similarity NPC477564
0.8696 High Similarity NPC470324
0.8693 High Similarity NPC60538
0.8693 High Similarity NPC207824
0.8679 High Similarity NPC320104
0.8679 High Similarity NPC233650
0.8659 High Similarity NPC474470
0.8658 High Similarity NPC474915
0.8658 High Similarity NPC188163
0.8658 High Similarity NPC328750
0.8658 High Similarity NPC213206
0.8645 High Similarity NPC148898
0.8645 High Similarity NPC37272
0.8642 High Similarity NPC311991
0.8609 High Similarity NPC294249
0.8599 High Similarity NPC186063
0.8554 High Similarity NPC244554
0.8553 High Similarity NPC27410
0.8553 High Similarity NPC166014
0.8545 High Similarity NPC237044
0.8544 High Similarity NPC148014
0.8544 High Similarity NPC78359
0.8544 High Similarity NPC315707
0.8544 High Similarity NPC65490
0.8544 High Similarity NPC40389
0.8526 High Similarity NPC26601
0.8519 High Similarity NPC150879
0.8506 High Similarity NPC475959
0.8494 Intermediate Similarity NPC474325
0.8485 Intermediate Similarity NPC304675
0.8481 Intermediate Similarity NPC37205
0.8481 Intermediate Similarity NPC160931
0.8466 Intermediate Similarity NPC164429
0.8457 Intermediate Similarity NPC13916
0.8457 Intermediate Similarity NPC264850
0.8443 Intermediate Similarity NPC474745
0.8442 Intermediate Similarity NPC476144
0.8442 Intermediate Similarity NPC106295
0.8442 Intermediate Similarity NPC210437
0.8442 Intermediate Similarity NPC51957
0.8442 Intermediate Similarity NPC16107
0.8438 Intermediate Similarity NPC4304
0.8424 Intermediate Similarity NPC2314
0.8421 Intermediate Similarity NPC476567
0.8421 Intermediate Similarity NPC128019
0.8421 Intermediate Similarity NPC136860
0.8415 Intermediate Similarity NPC75958
0.8405 Intermediate Similarity NPC252960
0.8395 Intermediate Similarity NPC24465
0.8395 Intermediate Similarity NPC247972
0.8387 Intermediate Similarity NPC7467
0.8383 Intermediate Similarity NPC15919
0.8373 Intermediate Similarity NPC187678
0.8365 Intermediate Similarity NPC323443
0.8365 Intermediate Similarity NPC180756
0.8356 Intermediate Similarity NPC160193
0.8354 Intermediate Similarity NPC83198
0.8354 Intermediate Similarity NPC204908
0.8344 Intermediate Similarity NPC476002
0.8344 Intermediate Similarity NPC317272
0.8344 Intermediate Similarity NPC42549
0.8344 Intermediate Similarity NPC256012
0.8344 Intermediate Similarity NPC250846
0.8344 Intermediate Similarity NPC268503
0.8344 Intermediate Similarity NPC240841
0.8333 Intermediate Similarity NPC193528
0.8333 Intermediate Similarity NPC324144
0.8333 Intermediate Similarity NPC218614
0.8333 Intermediate Similarity NPC219162
0.8323 Intermediate Similarity NPC226428
0.8313 Intermediate Similarity NPC129603
0.8302 Intermediate Similarity NPC216459
0.8302 Intermediate Similarity NPC138487
0.8302 Intermediate Similarity NPC41178
0.8294 Intermediate Similarity NPC474746
0.8294 Intermediate Similarity NPC475981
0.8293 Intermediate Similarity NPC306555
0.8293 Intermediate Similarity NPC145832
0.8293 Intermediate Similarity NPC117188
0.8293 Intermediate Similarity NPC205421
0.8293 Intermediate Similarity NPC12053
0.8293 Intermediate Similarity NPC298979
0.8293 Intermediate Similarity NPC81218
0.8293 Intermediate Similarity NPC474931
0.8293 Intermediate Similarity NPC158376
0.8291 Intermediate Similarity NPC223124
0.8282 Intermediate Similarity NPC255607
0.8282 Intermediate Similarity NPC96603
0.8282 Intermediate Similarity NPC78222
0.8282 Intermediate Similarity NPC284183
0.8282 Intermediate Similarity NPC477563
0.8282 Intermediate Similarity NPC136508
0.8282 Intermediate Similarity NPC3375
0.8282 Intermediate Similarity NPC13504
0.8282 Intermediate Similarity NPC196447
0.8282 Intermediate Similarity NPC4138
0.8282 Intermediate Similarity NPC253043
0.8282 Intermediate Similarity NPC121275
0.8282 Intermediate Similarity NPC212794
0.8282 Intermediate Similarity NPC306843
0.8282 Intermediate Similarity NPC76116
0.8274 Intermediate Similarity NPC21885
0.8272 Intermediate Similarity NPC60186
0.8263 Intermediate Similarity NPC49353
0.8261 Intermediate Similarity NPC118804
0.825 Intermediate Similarity NPC146288
0.8232 Intermediate Similarity NPC81247
0.8232 Intermediate Similarity NPC476573
0.8232 Intermediate Similarity NPC35627
0.8225 Intermediate Similarity NPC32154
0.8221 Intermediate Similarity NPC124433
0.8221 Intermediate Similarity NPC1229
0.8221 Intermediate Similarity NPC293871
0.8212 Intermediate Similarity NPC253429
0.8205 Intermediate Similarity NPC95075
0.8205 Intermediate Similarity NPC253883
0.8205 Intermediate Similarity NPC90844
0.8204 Intermediate Similarity NPC152680
0.8204 Intermediate Similarity NPC232386
0.8204 Intermediate Similarity NPC190783
0.8198 Intermediate Similarity NPC230098
0.8182 Intermediate Similarity NPC474324
0.8182 Intermediate Similarity NPC57812
0.8176 Intermediate Similarity NPC233029
0.8176 Intermediate Similarity NPC210148

  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 NPC147091 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
0.871 High Similarity NPD4772 Phase 2
0.871 High Similarity NPD4773 Phase 2
0.8696 High Similarity NPD2489 Approved
0.8696 High Similarity NPD2898 Approved
0.8696 High Similarity NPD27 Approved
0.8658 High Similarity NPD4664 Clinical (unspecified phase)
0.8571 High Similarity NPD6071 Discontinued
0.8544 High Similarity NPD2563 Approved
0.8544 High Similarity NPD2560 Approved
0.8519 High Similarity NPD2970 Approved
0.8519 High Similarity NPD2969 Approved
0.8442 Intermediate Similarity NPD4584 Approved
0.8366 Intermediate Similarity NPD5241 Discontinued
0.8344 Intermediate Similarity NPD3051 Approved
0.8232 Intermediate Similarity NPD4010 Discontinued
0.821 Intermediate Similarity NPD7831 Phase 2
0.821 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD7833 Phase 2
0.8205 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD4017 Approved
0.8101 Intermediate Similarity NPD3639 Approved
0.8101 Intermediate Similarity NPD3640 Phase 3
0.8101 Intermediate Similarity NPD3641 Approved
0.807 Intermediate Similarity NPD7312 Approved
0.807 Intermediate Similarity NPD7313 Approved
0.807 Intermediate Similarity NPD7310 Approved
0.807 Intermediate Similarity NPD7311 Approved
0.8023 Intermediate Similarity NPD7309 Approved
0.8 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD7906 Approved
0.7987 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7965 Intermediate Similarity NPD4577 Approved
0.7965 Intermediate Similarity NPD4578 Approved
0.7931 Intermediate Similarity NPD4663 Approved
0.7919 Intermediate Similarity NPD8053 Approved
0.7919 Intermediate Similarity NPD8054 Approved
0.7885 Intermediate Similarity NPD4236 Phase 3
0.7885 Intermediate Similarity NPD4237 Approved
0.7881 Intermediate Similarity NPD2674 Phase 3
0.7875 Intermediate Similarity NPD6031 Approved
0.7875 Intermediate Similarity NPD6030 Approved
0.7853 Intermediate Similarity NPD7298 Approved
0.7844 Intermediate Similarity NPD6107 Approved
0.7811 Intermediate Similarity NPD4481 Phase 3
0.7805 Intermediate Similarity NPD5772 Approved
0.7805 Intermediate Similarity NPD2978 Approved
0.7805 Intermediate Similarity NPD5773 Approved
0.7805 Intermediate Similarity NPD2977 Approved
0.7799 Intermediate Similarity NPD2421 Approved
0.7799 Intermediate Similarity NPD2420 Approved
0.7798 Intermediate Similarity NPD4166 Phase 2
0.7797 Intermediate Similarity NPD2490 Approved
0.7797 Intermediate Similarity NPD2488 Approved
0.7771 Intermediate Similarity NPD5177 Phase 3
0.7736 Intermediate Similarity NPD3845 Phase 1
0.7697 Intermediate Similarity NPD3145 Approved
0.7697 Intermediate Similarity NPD5718 Phase 2
0.7697 Intermediate Similarity NPD3144 Approved
0.7658 Intermediate Similarity NPD3060 Approved
0.7657 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD1753 Discontinued
0.7628 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD3124 Discontinued
0.7572 Intermediate Similarity NPD5313 Approved
0.7572 Intermediate Similarity NPD8156 Discontinued
0.7572 Intermediate Similarity NPD5312 Approved
0.7566 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD6895 Approved
0.7564 Intermediate Similarity NPD6896 Approved
0.7562 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD4162 Approved
0.7514 Intermediate Similarity NPD8099 Discontinued
0.7514 Intermediate Similarity NPD8252 Approved
0.7514 Intermediate Similarity NPD8251 Approved
0.75 Intermediate Similarity NPD823 Approved
0.75 Intermediate Similarity NPD817 Approved
0.75 Intermediate Similarity NPD6788 Approved
0.7486 Intermediate Similarity NPD6297 Approved
0.7484 Intermediate Similarity NPD3109 Approved
0.7484 Intermediate Similarity NPD3110 Approved
0.7484 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD2238 Phase 2
0.7484 Intermediate Similarity NPD3620 Phase 2
0.7457 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD2494 Approved
0.7419 Intermediate Similarity NPD3450 Approved
0.7419 Intermediate Similarity NPD2493 Approved
0.7419 Intermediate Similarity NPD3452 Approved
0.7416 Intermediate Similarity NPD6851 Approved
0.7416 Intermediate Similarity NPD6853 Approved
0.7403 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD3637 Approved
0.7386 Intermediate Similarity NPD3636 Approved
0.7386 Intermediate Similarity NPD3635 Approved
0.738 Intermediate Similarity NPD3448 Approved
0.738 Intermediate Similarity NPD2491 Approved
0.736 Intermediate Similarity NPD7281 Phase 3
0.736 Intermediate Similarity NPD2971 Approved
0.736 Intermediate Similarity NPD7280 Phase 3
0.736 Intermediate Similarity NPD2968 Approved
0.7358 Intermediate Similarity NPD2161 Phase 2
0.7349 Intermediate Similarity NPD824 Approved
0.7346 Intermediate Similarity NPD3692 Discontinued
0.7341 Intermediate Similarity NPD6688 Approved
0.7341 Intermediate Similarity NPD6687 Approved
0.7337 Intermediate Similarity NPD5977 Approved
0.7337 Intermediate Similarity NPD5978 Approved
0.7326 Intermediate Similarity NPD7802 Discontinued
0.7317 Intermediate Similarity NPD3645 Discontinued
0.7317 Intermediate Similarity NPD1424 Approved
0.7315 Intermediate Similarity NPD2668 Approved
0.7315 Intermediate Similarity NPD2667 Approved
0.7308 Intermediate Similarity NPD4474 Approved
0.7308 Intermediate Similarity NPD1132 Approved
0.7308 Intermediate Similarity NPD4475 Approved
0.7308 Intermediate Similarity NPD1136 Approved
0.7308 Intermediate Similarity NPD1130 Approved
0.7308 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD4040 Phase 1
0.7302 Intermediate Similarity NPD4583 Approved
0.7302 Intermediate Similarity NPD4582 Approved
0.7294 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD4210 Discontinued
0.7287 Intermediate Similarity NPD3057 Approved
0.7285 Intermediate Similarity NPD2230 Approved
0.7285 Intermediate Similarity NPD2232 Approved
0.7285 Intermediate Similarity NPD2233 Approved
0.7284 Intermediate Similarity NPD6331 Phase 2
0.7273 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD52 Approved
0.7273 Intermediate Similarity NPD7526 Approved
0.7267 Intermediate Similarity NPD2041 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD2042 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD7037 Approved
0.7255 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD3055 Approved
0.7255 Intermediate Similarity NPD3053 Approved
0.7255 Intermediate Similarity NPD4103 Phase 2
0.7249 Intermediate Similarity NPD4004 Approved
0.7249 Intermediate Similarity NPD4002 Approved
0.7246 Intermediate Similarity NPD4005 Discontinued
0.7246 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD601 Approved
0.7244 Intermediate Similarity NPD598 Approved
0.7244 Intermediate Similarity NPD597 Approved
0.7239 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD5160 Discontinued
0.7226 Intermediate Similarity NPD2606 Approved
0.7226 Intermediate Similarity NPD3594 Approved
0.7226 Intermediate Similarity NPD2605 Approved
0.7226 Intermediate Similarity NPD3595 Approved
0.7205 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD3656 Approved
0.7204 Intermediate Similarity NPD2974 Approved
0.7204 Intermediate Similarity NPD2975 Approved
0.7204 Intermediate Similarity NPD2973 Approved
0.7196 Intermediate Similarity NPD2972 Approved
0.7196 Intermediate Similarity NPD3533 Approved
0.7195 Intermediate Similarity NPD7124 Phase 2
0.7179 Intermediate Similarity NPD5156 Approved
0.7179 Intermediate Similarity NPD5155 Approved
0.7178 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD4873 Discontinued
0.7169 Intermediate Similarity NPD6090 Discontinued
0.7168 Intermediate Similarity NPD2904 Discontinued
0.716 Intermediate Similarity NPD7153 Discontinued
0.716 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD5582 Discontinued
0.7151 Intermediate Similarity NPD5604 Discontinued
0.7151 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD2122 Discontinued
0.7124 Intermediate Similarity NPD4659 Approved
0.712 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD5720 Discontinued
0.7108 Intermediate Similarity NPD2874 Phase 2
0.7108 Intermediate Similarity NPD7020 Approved
0.7108 Intermediate Similarity NPD7019 Approved
0.7108 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD4123 Phase 3
0.7097 Intermediate Similarity NPD7905 Discontinued
0.709 Intermediate Similarity NPD4580 Approved
0.7086 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD3686 Approved
0.7083 Intermediate Similarity NPD3687 Approved
0.7081 Intermediate Similarity NPD2154 Approved
0.7081 Intermediate Similarity NPD2156 Approved
0.7081 Intermediate Similarity NPD2155 Approved
0.7078 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD4420 Approved
0.7073 Intermediate Similarity NPD6748 Discontinued
0.7073 Intermediate Similarity NPD5754 Discontinued

  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