Structure

Physi-Chem Properties

Molecular Weight:  337.13
Volume:  345.316
LogP:  3.134
LogD:  2.987
LogS:  -4.905
# Rotatable Bonds:  3
TPSA:  49.69
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.736
Synthetic Accessibility Score:  2.573
Fsp3:  0.25
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.868
MDCK Permeability:  1.940362199093215e-05
Pgp-inhibitor:  0.252
Pgp-substrate:  0.715
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.371
30% Bioavailability (F30%):  0.25

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.854
Plasma Protein Binding (PPB):  83.77998352050781%
Volume Distribution (VD):  1.447
Pgp-substrate:  6.143038749694824%

ADMET: Metabolism

CYP1A2-inhibitor:  0.478
CYP1A2-substrate:  0.96
CYP2C19-inhibitor:  0.646
CYP2C19-substrate:  0.511
CYP2C9-inhibitor:  0.577
CYP2C9-substrate:  0.899
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.948
CYP3A4-inhibitor:  0.724
CYP3A4-substrate:  0.528

ADMET: Excretion

Clearance (CL):  6.769
Half-life (T1/2):  0.385

ADMET: Toxicity

hERG Blockers:  0.103
Human Hepatotoxicity (H-HT):  0.211
Drug-inuced Liver Injury (DILI):  0.858
AMES Toxicity:  0.644
Rat Oral Acute Toxicity:  0.063
Maximum Recommended Daily Dose:  0.876
Skin Sensitization:  0.481
Carcinogencity:  0.332
Eye Corrosion:  0.003
Eye Irritation:  0.015
Respiratory Toxicity:  0.529

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

  Natural Product: NPC476579

Natural Product ID:  NPC476579
Common Name*:   Dehydrocorydalmine Trifluoroacetate
IUPAC Name:   2,2,2-trifluoroacetate;2,3,9-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-10-ol
Synonyms:   Dehydrocorydalmine Trifluoroacetate
Standard InCHIKey:  CSWPZGWKRPVJCH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H19NO4.C2HF3O2/c1-23-18-9-13-6-7-21-11-15-12(4-5-17(22)20(15)25-3)8-16(21)14(13)10-19(18)24-2;3-2(4,5)1(6)7/h4-5,8-11H,6-7H2,1-3H3;(H,6,7)
SMILES:  COC1=C(C=C2C(=C1)CC[N+]3=C2C=C4C=CC(=C(C4=C3)OC)O)OC.C(=O)(C(F)(F)F)[O-]
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   52946916
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001909] Protoberberine alkaloids 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
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. stem wood n.a. DOI[10.1021/np100247r]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10395501]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10425140]
NPO6333 Annona glabra Species Annonaceae Eukaryota Fruits n.a. n.a. PMID[15568797]
NPO6333 Annona glabra Species Annonaceae Eukaryota stem Taipei Botanical Garden, Taipei, Taiwan, China 2006-MAR PMID[20828184]
NPO6333 Annona glabra Species Annonaceae Eukaryota fruits n.a. n.a. PMID[25499882]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9584397]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9599260]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6333 Annona glabra Species Annonaceae 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 = 96500 nM PMID[20828184]

☑ 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 NPC476579 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
0.9463 High Similarity NPC106786
0.9404 High Similarity NPC59567
0.9257 High Similarity NPC476580
0.9073 High Similarity NPC57512
0.906 High Similarity NPC85747
0.906 High Similarity NPC8337
0.9034 High Similarity NPC136860
0.9034 High Similarity NPC128019
0.9034 High Similarity NPC476567
0.8919 High Similarity NPC51957
0.8919 High Similarity NPC476144
0.8919 High Similarity NPC106295
0.8919 High Similarity NPC210437
0.8919 High Similarity NPC16107
0.8903 High Similarity NPC476569
0.8897 High Similarity NPC328750
0.8897 High Similarity NPC188163
0.8897 High Similarity NPC213206
0.8897 High Similarity NPC474915
0.8859 High Similarity NPC7467
0.8828 High Similarity NPC314682
0.871 High Similarity NPC118804
0.8658 High Similarity NPC130926
0.8654 High Similarity NPC226428
0.8618 High Similarity NPC151895
0.8618 High Similarity NPC223125
0.8618 High Similarity NPC192768
0.8618 High Similarity NPC88249
0.8618 High Similarity NPC97221
0.8618 High Similarity NPC220858
0.8608 High Similarity NPC306669
0.8608 High Similarity NPC255607
0.8608 High Similarity NPC3375
0.8592 High Similarity NPC160193
0.8533 High Similarity NPC185838
0.8516 High Similarity NPC276588
0.8516 High Similarity NPC2413
0.8516 High Similarity NPC278799
0.8516 High Similarity NPC41178
0.8516 High Similarity NPC204828
0.8516 High Similarity NPC127674
0.8516 High Similarity NPC469817
0.8516 High Similarity NPC249797
0.8516 High Similarity NPC138487
0.8516 High Similarity NPC54379
0.8516 High Similarity NPC207757
0.8516 High Similarity NPC39701
0.8516 High Similarity NPC172765
0.8516 High Similarity NPC184026
0.8516 High Similarity NPC193949
0.8516 High Similarity NPC189266
0.8516 High Similarity NPC295691
0.8516 High Similarity NPC216459
0.8516 High Similarity NPC5238
0.8516 High Similarity NPC110416
0.8506 High Similarity NPC210148
0.8506 High Similarity NPC233029
0.8506 High Similarity NPC223124
0.8487 Intermediate Similarity NPC24233
0.8487 Intermediate Similarity NPC475959
0.8487 Intermediate Similarity NPC147390
0.8487 Intermediate Similarity NPC246587
0.8487 Intermediate Similarity NPC135538
0.8487 Intermediate Similarity NPC476571
0.8487 Intermediate Similarity NPC428
0.8462 Intermediate Similarity NPC247639
0.8462 Intermediate Similarity NPC146288
0.8462 Intermediate Similarity NPC25084
0.8431 Intermediate Similarity NPC92541
0.8421 Intermediate Similarity NPC321505
0.8421 Intermediate Similarity NPC179825
0.8421 Intermediate Similarity NPC191376
0.8405 Intermediate Similarity NPC4669
0.8397 Intermediate Similarity NPC187022
0.8397 Intermediate Similarity NPC80129
0.8387 Intermediate Similarity NPC37272
0.8377 Intermediate Similarity NPC274026
0.8375 Intermediate Similarity NPC39103
0.8375 Intermediate Similarity NPC2770
0.8375 Intermediate Similarity NPC231198
0.8344 Intermediate Similarity NPC31311
0.8344 Intermediate Similarity NPC234392
0.8333 Intermediate Similarity NPC470324
0.8323 Intermediate Similarity NPC81733
0.8323 Intermediate Similarity NPC326316
0.8323 Intermediate Similarity NPC476568
0.8311 Intermediate Similarity NPC253429
0.8303 Intermediate Similarity NPC241704
0.8301 Intermediate Similarity NPC476151
0.8301 Intermediate Similarity NPC144863
0.8272 Intermediate Similarity NPC471604
0.8269 Intermediate Similarity NPC148898
0.8269 Intermediate Similarity NPC133011
0.8269 Intermediate Similarity NPC82285
0.8239 Intermediate Similarity NPC111485
0.8239 Intermediate Similarity NPC216816
0.8204 Intermediate Similarity NPC32154
0.8199 Intermediate Similarity NPC475393
0.8194 Intermediate Similarity NPC60538
0.8194 Intermediate Similarity NPC103379
0.8194 Intermediate Similarity NPC219162
0.8194 Intermediate Similarity NPC477565
0.8194 Intermediate Similarity NPC207824
0.8194 Intermediate Similarity NPC172403
0.8193 Intermediate Similarity NPC222524
0.8176 Intermediate Similarity NPC476572
0.8165 Intermediate Similarity NPC99659
0.8165 Intermediate Similarity NPC325871
0.8165 Intermediate Similarity NPC78733
0.8163 Intermediate Similarity NPC160692
0.8153 Intermediate Similarity NPC470924
0.8148 Intermediate Similarity NPC276944
0.8148 Intermediate Similarity NPC232514
0.8148 Intermediate Similarity NPC238530
0.8129 Intermediate Similarity NPC130941
0.8125 Intermediate Similarity NPC477080
0.8125 Intermediate Similarity NPC59028
0.8125 Intermediate Similarity NPC92191
0.8121 Intermediate Similarity NPC301050
0.8121 Intermediate Similarity NPC7018
0.8121 Intermediate Similarity NPC131204
0.8113 Intermediate Similarity NPC147091
0.8098 Intermediate Similarity NPC240841
0.8098 Intermediate Similarity NPC42549
0.8098 Intermediate Similarity NPC250846
0.8098 Intermediate Similarity NPC317272
0.8098 Intermediate Similarity NPC264850
0.8098 Intermediate Similarity NPC13916
0.8098 Intermediate Similarity NPC256012
0.8098 Intermediate Similarity NPC268503
0.8089 Intermediate Similarity NPC218575
0.8089 Intermediate Similarity NPC76213
0.8089 Intermediate Similarity NPC277669
0.8075 Intermediate Similarity NPC475780
0.8065 Intermediate Similarity NPC253883
0.8065 Intermediate Similarity NPC90844
0.8065 Intermediate Similarity NPC95075
0.805 Intermediate Similarity NPC93593
0.8037 Intermediate Similarity NPC121275
0.8037 Intermediate Similarity NPC284183
0.8037 Intermediate Similarity NPC24465
0.8037 Intermediate Similarity NPC4138
0.8025 Intermediate Similarity NPC153631
0.8 Intermediate Similarity NPC170503
0.8 Intermediate Similarity NPC203784
0.8 Intermediate Similarity NPC126519
0.7975 Intermediate Similarity NPC119669
0.7963 Intermediate Similarity NPC166014
0.7963 Intermediate Similarity NPC266753
0.7963 Intermediate Similarity NPC160298
0.7963 Intermediate Similarity NPC205167
0.7963 Intermediate Similarity NPC27410
0.7963 Intermediate Similarity NPC232924
0.7963 Intermediate Similarity NPC306902
0.7963 Intermediate Similarity NPC477559
0.795 Intermediate Similarity NPC475326
0.7941 Intermediate Similarity NPC298339
0.7939 Intermediate Similarity NPC474324
0.7939 Intermediate Similarity NPC57812
0.7937 Intermediate Similarity NPC244112
0.7933 Intermediate Similarity NPC11147
0.7929 Intermediate Similarity NPC21885
0.7908 Intermediate Similarity NPC470925
0.7904 Intermediate Similarity NPC227060
0.7904 Intermediate Similarity NPC317439
0.7904 Intermediate Similarity NPC76682
0.7904 Intermediate Similarity NPC115284
0.7904 Intermediate Similarity NPC276890
0.7904 Intermediate Similarity NPC317145
0.7904 Intermediate Similarity NPC63646
0.7904 Intermediate Similarity NPC10908
0.7904 Intermediate Similarity NPC198498
0.7892 Intermediate Similarity NPC475845
0.7892 Intermediate Similarity NPC241055
0.7892 Intermediate Similarity NPC66573
0.7888 Intermediate Similarity NPC323443
0.7888 Intermediate Similarity NPC180756
0.7879 Intermediate Similarity NPC476432
0.7879 Intermediate Similarity NPC24264
0.7875 Intermediate Similarity NPC477564
0.7875 Intermediate Similarity NPC2295
0.7871 Intermediate Similarity NPC294249
0.7866 Intermediate Similarity NPC233650
0.7866 Intermediate Similarity NPC324144
0.7861 Intermediate Similarity NPC477259
0.7861 Intermediate Similarity NPC169387
0.7857 Intermediate Similarity NPC251580
0.7857 Intermediate Similarity NPC41376
0.7857 Intermediate Similarity NPC2314
0.7857 Intermediate Similarity NPC12424
0.7857 Intermediate Similarity NPC129518
0.7853 Intermediate Similarity NPC215829
0.7853 Intermediate Similarity NPC249274
0.7853 Intermediate Similarity NPC97072
0.7844 Intermediate Similarity NPC474708
0.7844 Intermediate Similarity NPC109925
0.7831 Intermediate Similarity NPC474931
0.7831 Intermediate Similarity NPC284842
0.7831 Intermediate Similarity NPC306555
0.7831 Intermediate Similarity NPC12053

  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 NPC476579 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
0.8919 High Similarity NPD4584 Approved
0.8897 High Similarity NPD4664 Clinical (unspecified phase)
0.88 High Similarity NPD3639 Approved
0.88 High Similarity NPD3640 Phase 3
0.88 High Similarity NPD3641 Approved
0.8397 Intermediate Similarity NPD7298 Approved
0.8333 Intermediate Similarity NPD2898 Approved
0.8217 Intermediate Similarity NPD4772 Phase 2
0.8217 Intermediate Similarity NPD4773 Phase 2
0.8205 Intermediate Similarity NPD4017 Approved
0.8148 Intermediate Similarity NPD6107 Approved
0.8077 Intermediate Similarity NPD6030 Approved
0.8077 Intermediate Similarity NPD6031 Approved
0.8063 Intermediate Similarity NPD5977 Approved
0.8063 Intermediate Similarity NPD5978 Approved
0.8 Intermediate Similarity NPD3124 Discontinued
0.7988 Intermediate Similarity NPD4166 Phase 2
0.7959 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7947 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7947 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7941 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7905 Intermediate Similarity NPD5718 Phase 2
0.7904 Intermediate Similarity NPD8251 Approved
0.7904 Intermediate Similarity NPD8099 Discontinued
0.7904 Intermediate Similarity NPD8252 Approved
0.7866 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD5312 Approved
0.7857 Intermediate Similarity NPD5313 Approved
0.7857 Intermediate Similarity NPD8156 Discontinued
0.7791 Intermediate Similarity NPD6618 Phase 2
0.7778 Intermediate Similarity NPD4585 Approved
0.7711 Intermediate Similarity NPD7802 Discontinued
0.7702 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD4481 Phase 3
0.7665 Intermediate Similarity NPD4010 Discontinued
0.7651 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6895 Approved
0.7647 Intermediate Similarity NPD6896 Approved
0.7643 Intermediate Similarity NPD5241 Discontinued
0.7586 Intermediate Similarity NPD8053 Approved
0.7586 Intermediate Similarity NPD8054 Approved
0.7582 Intermediate Similarity NPD2492 Phase 1
0.7576 Intermediate Similarity NPD6788 Approved
0.7561 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD6071 Discontinued
0.7558 Intermediate Similarity NPD6297 Approved
0.7557 Intermediate Similarity NPD7291 Discontinued
0.7546 Intermediate Similarity NPD5090 Approved
0.7546 Intermediate Similarity NPD7110 Phase 1
0.7546 Intermediate Similarity NPD5089 Approved
0.7546 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD7833 Phase 2
0.753 Intermediate Similarity NPD7831 Phase 2
0.753 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD2968 Approved
0.7529 Intermediate Similarity NPD2971 Approved
0.7515 Intermediate Similarity NPD2563 Approved
0.7515 Intermediate Similarity NPD2560 Approved
0.75 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD3109 Approved
0.7451 Intermediate Similarity NPD3110 Approved
0.7427 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD2970 Approved
0.7412 Intermediate Similarity NPD2969 Approved
0.7407 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD1424 Approved
0.7386 Intermediate Similarity NPD6851 Approved
0.7386 Intermediate Similarity NPD6853 Approved
0.7368 Intermediate Similarity NPD2489 Approved
0.7368 Intermediate Similarity NPD27 Approved
0.7353 Intermediate Similarity NPD3051 Approved
0.7346 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD4859 Phase 1
0.7337 Intermediate Similarity NPD4107 Approved
0.7317 Intermediate Similarity NPD824 Approved
0.731 Intermediate Similarity NPD6687 Approved
0.731 Intermediate Similarity NPD6688 Approved
0.7278 Intermediate Similarity NPD2490 Approved
0.7278 Intermediate Similarity NPD2488 Approved
0.7273 Intermediate Similarity NPD6876 Approved
0.7273 Intermediate Similarity NPD6875 Approved
0.7273 Intermediate Similarity NPD2674 Phase 3
0.7267 Intermediate Similarity NPD7124 Phase 2
0.725 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2653 Approved
0.7235 Intermediate Similarity NPD5677 Discontinued
0.7232 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD6873 Phase 2
0.7229 Intermediate Similarity NPD6386 Approved
0.7229 Intermediate Similarity NPD6385 Approved
0.7228 Intermediate Similarity NPD4420 Approved
0.7222 Intermediate Similarity NPD2421 Approved
0.7222 Intermediate Similarity NPD5297 Approved
0.7222 Intermediate Similarity NPD2420 Approved
0.7213 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD4482 Phase 3
0.7188 Intermediate Similarity NPD5177 Phase 3
0.7182 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD2973 Approved
0.7174 Intermediate Similarity NPD2975 Approved
0.7174 Intermediate Similarity NPD2974 Approved
0.7174 Intermediate Similarity NPD5564 Approved
0.717 Intermediate Similarity NPD3656 Approved
0.7166 Intermediate Similarity NPD3057 Approved
0.7161 Intermediate Similarity NPD4475 Approved
0.7161 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD4474 Approved
0.716 Intermediate Similarity NPD3845 Phase 1
0.7152 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD5457 Discontinued
0.7134 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD7598 Phase 2
0.711 Intermediate Similarity NPD5242 Approved
0.7102 Intermediate Similarity NPD3885 Approved
0.7097 Intermediate Similarity NPD8095 Phase 1
0.7097 Intermediate Similarity NPD3144 Approved
0.7097 Intermediate Similarity NPD3145 Approved
0.7086 Intermediate Similarity NPD1421 Approved
0.7086 Intermediate Similarity NPD1420 Approved
0.7081 Intermediate Similarity NPD3060 Approved
0.7081 Intermediate Similarity NPD4162 Approved
0.7075 Intermediate Similarity NPD5536 Phase 2
0.7074 Intermediate Similarity NPD3533 Approved
0.7074 Intermediate Similarity NPD5005 Approved
0.7074 Intermediate Similarity NPD5006 Approved
0.7074 Intermediate Similarity NPD2972 Approved
0.7059 Intermediate Similarity NPD4580 Approved
0.7059 Intermediate Similarity NPD7905 Discontinued
0.7056 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD4210 Discontinued
0.7047 Intermediate Similarity NPD2668 Approved
0.7047 Intermediate Similarity NPD5676 Approved
0.7047 Intermediate Similarity NPD2667 Approved
0.7045 Intermediate Similarity NPD3050 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD5071 Phase 2
0.7039 Intermediate Similarity NPD7311 Approved
0.7039 Intermediate Similarity NPD7313 Approved
0.7039 Intermediate Similarity NPD7281 Phase 3
0.7039 Intermediate Similarity NPD7280 Phase 3
0.7039 Intermediate Similarity NPD7312 Approved
0.7039 Intermediate Similarity NPD7310 Approved
0.7037 Intermediate Similarity NPD6748 Discontinued
0.7034 Intermediate Similarity NPD5283 Phase 1
0.7021 Intermediate Similarity NPD3452 Approved
0.7021 Intermediate Similarity NPD2494 Approved
0.7021 Intermediate Similarity NPD2493 Approved
0.7021 Intermediate Similarity NPD3450 Approved
0.7019 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD4055 Discovery
0.7006 Intermediate Similarity NPD3142 Approved
0.7006 Intermediate Similarity NPD3920 Phase 2
0.7006 Intermediate Similarity NPD3140 Approved
0.7006 Intermediate Similarity NPD3866 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7309 Approved
0.6993 Remote Similarity NPD4098 Discontinued
0.6988 Remote Similarity NPD4727 Phase 1
0.6988 Remote Similarity NPD2122 Discontinued
0.6987 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6984 Remote Similarity NPD2491 Approved
0.6984 Remote Similarity NPD3448 Approved
0.6982 Remote Similarity NPD5720 Discontinued
0.6982 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6111 Discontinued
0.6978 Remote Similarity NPD7906 Approved
0.6975 Remote Similarity NPD4236 Phase 3
0.6975 Remote Similarity NPD4237 Approved
0.6959 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6957 Remote Similarity NPD3922 Approved
0.6957 Remote Similarity NPD3924 Approved
0.6957 Remote Similarity NPD3921 Approved
0.6957 Remote Similarity NPD3923 Approved
0.6951 Remote Similarity NPD2120 Phase 2
0.6937 Remote Similarity NPD1753 Discontinued
0.6933 Remote Similarity NPD3977 Clinical (unspecified phase)
0.6933 Remote Similarity NPD5754 Discontinued
0.6919 Remote Similarity NPD1309 Phase 2
0.6919 Remote Similarity NPD1307 Phase 2
0.6914 Remote Similarity NPD7153 Discontinued
0.6911 Remote Similarity NPD4583 Approved
0.6911 Remote Similarity NPD4582 Approved
0.691 Remote Similarity NPD5900 Clinical (unspecified phase)
0.6908 Remote Similarity NPD2233 Approved
0.6908 Remote Similarity NPD2230 Approved
0.6908 Remote Similarity NPD2232 Approved
0.6905 Remote Similarity NPD4005 Discontinued
0.6901 Remote Similarity NPD5967 Approved
0.6894 Remote Similarity NPD2161 Phase 2
0.6893 Remote Similarity NPD5708 Clinical (unspecified phase)
0.689 Remote Similarity NPD3692 Discontinued
0.6889 Remote Similarity NPD7549 Discontinued
0.6886 Remote Similarity NPD1914 Approved
0.6882 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6879 Remote Similarity NPD5111 Phase 2

  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