Structure

Physi-Chem Properties

Molecular Weight:  512.24
Volume:  519.224
LogP:  3.577
LogD:  2.962
LogS:  -4.574
# Rotatable Bonds:  4
TPSA:  115.43
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.593
Synthetic Accessibility Score:  4.633
Fsp3:  0.586
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.873
MDCK Permeability:  1.4002940588397905e-05
Pgp-inhibitor:  0.988
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  0.251
30% Bioavailability (F30%):  0.856

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.137
Plasma Protein Binding (PPB):  90.56709289550781%
Volume Distribution (VD):  1.039
Pgp-substrate:  10.323067665100098%

ADMET: Metabolism

CYP1A2-inhibitor:  0.656
CYP1A2-substrate:  0.922
CYP2C19-inhibitor:  0.912
CYP2C19-substrate:  0.663
CYP2C9-inhibitor:  0.876
CYP2C9-substrate:  0.406
CYP2D6-inhibitor:  0.359
CYP2D6-substrate:  0.465
CYP3A4-inhibitor:  0.903
CYP3A4-substrate:  0.836

ADMET: Excretion

Clearance (CL):  5.185
Half-life (T1/2):  0.075

ADMET: Toxicity

hERG Blockers:  0.49
Human Hepatotoxicity (H-HT):  0.837
Drug-inuced Liver Injury (DILI):  0.781
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.307
Maximum Recommended Daily Dose:  0.927
Skin Sensitization:  0.154
Carcinogencity:  0.975
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.957

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

  Natural Product: NPC119252

Natural Product ID:  NPC119252
Common Name*:   LHKWCVMCNOROFZ-MCPFUKIPSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  LHKWCVMCNOROFZ-MCPFUKIPSA-N
Standard InCHI:  InChI=1S/C29H36O8/c1-17(30)35-23-11-12-26(4)28(32,25(23,2)3)14-13-27(5)29(26,33)16-20-22(37-27)15-21(36-24(20)31)18-7-9-19(34-6)10-8-18/h7-10,15,23,32-33H,11-14,16H2,1-6H3/t23-,26+,27-,28-,29+/m1/s1
SMILES:  CC(=O)O[C@@H]1CC[C@@]2(C)[C@@](CC[C@]3(C)[C@@]2(Cc2c(cc(c4ccc(cc4)OC)oc2=O)O3)O)(C1(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3632853
PubChem CID:   11756147
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001640] Naphthopyrans

*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
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10479323]
NPO31059 Penicillium Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10724005]
NPO31059 Penicillium Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10724008]
NPO31059 Penicillium Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[11099218]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12350167]
NPO31059 Penicillium Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12350167]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[14640527]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota Axinella verrucosa Mediterranean n.a. PMID[14738391]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15043411]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Sussex Inlet, New South Wales, Australia n.a. PMID[15104517]
NPO31059 Penicillium Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15332861]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15332862]
NPO31059 Penicillium Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15387518]
NPO31059 Penicillium Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16568716]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Berkeley Pit lake n.a. PMID[17970594]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. New Zealand n.a. PMID[19323568]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19326880]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20452770]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. North Sea n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Limonium tubiflorum n.a. PMID[21146414]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21916432]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22148349]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22458669]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23360521]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23477451]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23603293]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23972215]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24437979]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31433188]
NPO31059 Penicillium Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[7649881]
NPO31059 Penicillium Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[8002401]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[9392888]
NPO31059 Penicillium Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[9711252]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]

☑ 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
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 3500.0 nM PMID[495346]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 60.1 % PMID[495347]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 4.7 % PMID[495347]

☑ 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 NPC119252 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
0.9324 High Similarity NPC231668
0.9211 High Similarity NPC268602
0.9048 High Similarity NPC169942
0.8535 High Similarity NPC195954
0.8535 High Similarity NPC88007
0.8528 High Similarity NPC472803
0.8516 High Similarity NPC48671
0.8491 Intermediate Similarity NPC68848
0.8476 Intermediate Similarity NPC148185
0.8442 Intermediate Similarity NPC146388
0.8428 Intermediate Similarity NPC8389
0.8418 Intermediate Similarity NPC194499
0.8387 Intermediate Similarity NPC146014
0.8387 Intermediate Similarity NPC327962
0.8375 Intermediate Similarity NPC79571
0.8375 Intermediate Similarity NPC188649
0.8375 Intermediate Similarity NPC472055
0.8355 Intermediate Similarity NPC25491
0.8354 Intermediate Similarity NPC472807
0.8354 Intermediate Similarity NPC266545
0.8354 Intermediate Similarity NPC202428
0.8344 Intermediate Similarity NPC200726
0.8344 Intermediate Similarity NPC471823
0.8344 Intermediate Similarity NPC469394
0.8344 Intermediate Similarity NPC296558
0.8344 Intermediate Similarity NPC291742
0.8333 Intermediate Similarity NPC277618
0.8333 Intermediate Similarity NPC161151
0.8333 Intermediate Similarity NPC120012
0.8323 Intermediate Similarity NPC88841
0.8323 Intermediate Similarity NPC288602
0.8323 Intermediate Similarity NPC285567
0.8323 Intermediate Similarity NPC306799
0.8323 Intermediate Similarity NPC101043
0.8313 Intermediate Similarity NPC470339
0.8302 Intermediate Similarity NPC470896
0.8302 Intermediate Similarity NPC7059
0.8302 Intermediate Similarity NPC473275
0.8293 Intermediate Similarity NPC177362
0.8291 Intermediate Similarity NPC62051
0.828 Intermediate Similarity NPC124842
0.828 Intermediate Similarity NPC473773
0.828 Intermediate Similarity NPC475579
0.8278 Intermediate Similarity NPC172311
0.8267 Intermediate Similarity NPC171207
0.8267 Intermediate Similarity NPC97667
0.8263 Intermediate Similarity NPC294149
0.8258 Intermediate Similarity NPC477483
0.8258 Intermediate Similarity NPC325032
0.8247 Intermediate Similarity NPC98356
0.8242 Intermediate Similarity NPC217378
0.8239 Intermediate Similarity NPC159692
0.8239 Intermediate Similarity NPC41880
0.8235 Intermediate Similarity NPC127857
0.8232 Intermediate Similarity NPC472621
0.8232 Intermediate Similarity NPC469396
0.8232 Intermediate Similarity NPC469458
0.8232 Intermediate Similarity NPC88176
0.8232 Intermediate Similarity NPC149002
0.8228 Intermediate Similarity NPC146277
0.8228 Intermediate Similarity NPC19380
0.8224 Intermediate Similarity NPC477894
0.8221 Intermediate Similarity NPC308156
0.8221 Intermediate Similarity NPC121995
0.8217 Intermediate Similarity NPC118033
0.8217 Intermediate Similarity NPC261659
0.8212 Intermediate Similarity NPC118080
0.8212 Intermediate Similarity NPC27377
0.8212 Intermediate Similarity NPC472576
0.8212 Intermediate Similarity NPC97947
0.8212 Intermediate Similarity NPC41481
0.8212 Intermediate Similarity NPC16912
0.8212 Intermediate Similarity NPC291599
0.8212 Intermediate Similarity NPC87448
0.821 Intermediate Similarity NPC283209
0.821 Intermediate Similarity NPC266365
0.8205 Intermediate Similarity NPC473719
0.8204 Intermediate Similarity NPC124828
0.8194 Intermediate Similarity NPC250046
0.8194 Intermediate Similarity NPC60509
0.8194 Intermediate Similarity NPC81698
0.8194 Intermediate Similarity NPC286038
0.8193 Intermediate Similarity NPC313304
0.8188 Intermediate Similarity NPC233350
0.8188 Intermediate Similarity NPC70680
0.8188 Intermediate Similarity NPC182217
0.8182 Intermediate Similarity NPC472622
0.8176 Intermediate Similarity NPC188217
0.8171 Intermediate Similarity NPC270312
0.817 Intermediate Similarity NPC57628
0.817 Intermediate Similarity NPC472569
0.817 Intermediate Similarity NPC163719
0.817 Intermediate Similarity NPC241951
0.817 Intermediate Similarity NPC70716
0.817 Intermediate Similarity NPC95265
0.817 Intermediate Similarity NPC125106
0.817 Intermediate Similarity NPC470152
0.817 Intermediate Similarity NPC472573
0.817 Intermediate Similarity NPC472570
0.817 Intermediate Similarity NPC25768
0.817 Intermediate Similarity NPC476974
0.817 Intermediate Similarity NPC11685
0.817 Intermediate Similarity NPC95810
0.817 Intermediate Similarity NPC475759
0.817 Intermediate Similarity NPC188865
0.8165 Intermediate Similarity NPC270268
0.8165 Intermediate Similarity NPC121615
0.8165 Intermediate Similarity NPC163883
0.8165 Intermediate Similarity NPC26033
0.8165 Intermediate Similarity NPC294511
0.8165 Intermediate Similarity NPC228204
0.8165 Intermediate Similarity NPC93498
0.8158 Intermediate Similarity NPC304110
0.8158 Intermediate Similarity NPC3218
0.8158 Intermediate Similarity NPC155552
0.8158 Intermediate Similarity NPC27518
0.8155 Intermediate Similarity NPC469438
0.8155 Intermediate Similarity NPC469354
0.8153 Intermediate Similarity NPC472548
0.8153 Intermediate Similarity NPC477905
0.8153 Intermediate Similarity NPC228842
0.8153 Intermediate Similarity NPC212257
0.8153 Intermediate Similarity NPC474305
0.8148 Intermediate Similarity NPC18986
0.8146 Intermediate Similarity NPC24295
0.8146 Intermediate Similarity NPC265335
0.8146 Intermediate Similarity NPC90614
0.8146 Intermediate Similarity NPC100913
0.8146 Intermediate Similarity NPC283560
0.8146 Intermediate Similarity NPC275592
0.8144 Intermediate Similarity NPC472620
0.8144 Intermediate Similarity NPC477617
0.8141 Intermediate Similarity NPC112216
0.8141 Intermediate Similarity NPC1580
0.8141 Intermediate Similarity NPC161239
0.8141 Intermediate Similarity NPC66991
0.8141 Intermediate Similarity NPC165260
0.8141 Intermediate Similarity NPC470757
0.8141 Intermediate Similarity NPC198455
0.8141 Intermediate Similarity NPC7095
0.8133 Intermediate Similarity NPC294512
0.8133 Intermediate Similarity NPC102810
0.8129 Intermediate Similarity NPC281717
0.8125 Intermediate Similarity NPC68727
0.8121 Intermediate Similarity NPC469459
0.8121 Intermediate Similarity NPC255787
0.8121 Intermediate Similarity NPC68517
0.8121 Intermediate Similarity NPC469419
0.8118 Intermediate Similarity NPC93685
0.8118 Intermediate Similarity NPC108191
0.8117 Intermediate Similarity NPC474599
0.8117 Intermediate Similarity NPC174982
0.8117 Intermediate Similarity NPC471876
0.8117 Intermediate Similarity NPC469349
0.8117 Intermediate Similarity NPC177940
0.8117 Intermediate Similarity NPC473088
0.8117 Intermediate Similarity NPC29704
0.8117 Intermediate Similarity NPC472575
0.8117 Intermediate Similarity NPC472568
0.8117 Intermediate Similarity NPC471104
0.8117 Intermediate Similarity NPC470157
0.8117 Intermediate Similarity NPC469615
0.8117 Intermediate Similarity NPC472572
0.8117 Intermediate Similarity NPC200471
0.8117 Intermediate Similarity NPC70403
0.8117 Intermediate Similarity NPC96903
0.8117 Intermediate Similarity NPC470159
0.8117 Intermediate Similarity NPC476973
0.8117 Intermediate Similarity NPC472571
0.8117 Intermediate Similarity NPC184817
0.8117 Intermediate Similarity NPC158663
0.8117 Intermediate Similarity NPC470130
0.8117 Intermediate Similarity NPC171525
0.8113 Intermediate Similarity NPC178574
0.8113 Intermediate Similarity NPC205392
0.8113 Intermediate Similarity NPC65591
0.8113 Intermediate Similarity NPC105942
0.811 Intermediate Similarity NPC100420
0.8105 Intermediate Similarity NPC163087
0.8101 Intermediate Similarity NPC473414
0.8101 Intermediate Similarity NPC265395
0.8101 Intermediate Similarity NPC472005
0.8101 Intermediate Similarity NPC472030
0.8101 Intermediate Similarity NPC473579
0.8101 Intermediate Similarity NPC249471
0.8101 Intermediate Similarity NPC158333
0.8101 Intermediate Similarity NPC475454
0.8101 Intermediate Similarity NPC242262
0.8101 Intermediate Similarity NPC237549
0.8101 Intermediate Similarity NPC256142
0.8101 Intermediate Similarity NPC304876
0.8101 Intermediate Similarity NPC257213
0.8101 Intermediate Similarity NPC140133
0.8101 Intermediate Similarity NPC473680
0.8101 Intermediate Similarity NPC225854
0.8101 Intermediate Similarity NPC1173
0.8101 Intermediate Similarity NPC77719
0.8101 Intermediate Similarity NPC475311
0.8101 Intermediate Similarity NPC472022
0.8098 Intermediate Similarity NPC124747

  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 NPC119252 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
0.8118 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD4628 Phase 3
0.7988 Intermediate Similarity NPD8127 Discontinued
0.7963 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD6190 Approved
0.7917 Intermediate Similarity NPD5844 Phase 1
0.7888 Intermediate Similarity NPD37 Approved
0.7866 Intermediate Similarity NPD6234 Discontinued
0.7861 Intermediate Similarity NPD8434 Phase 2
0.7857 Intermediate Similarity NPD7228 Approved
0.7853 Intermediate Similarity NPD4967 Phase 2
0.7853 Intermediate Similarity NPD4966 Approved
0.7853 Intermediate Similarity NPD4965 Approved
0.7831 Intermediate Similarity NPD6232 Discontinued
0.7829 Intermediate Similarity NPD7097 Phase 1
0.7812 Intermediate Similarity NPD7458 Discontinued
0.7798 Intermediate Similarity NPD7473 Discontinued
0.7784 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD4380 Phase 2
0.7756 Intermediate Similarity NPD8166 Discontinued
0.7733 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD7819 Suspended
0.773 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD8455 Phase 2
0.7697 Intermediate Similarity NPD7075 Discontinued
0.7683 Intermediate Similarity NPD3817 Phase 2
0.7682 Intermediate Similarity NPD6233 Phase 2
0.7674 Intermediate Similarity NPD7240 Approved
0.7673 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD7095 Approved
0.7654 Intermediate Similarity NPD6599 Discontinued
0.7643 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD3787 Discontinued
0.7616 Intermediate Similarity NPD6798 Discontinued
0.761 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD6355 Discontinued
0.758 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD5402 Approved
0.7561 Intermediate Similarity NPD6801 Discontinued
0.756 Intermediate Similarity NPD7199 Phase 2
0.7554 Intermediate Similarity NPD7497 Discontinued
0.7544 Intermediate Similarity NPD3751 Discontinued
0.7532 Intermediate Similarity NPD7003 Approved
0.7529 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6166 Phase 2
0.7516 Intermediate Similarity NPD6273 Approved
0.7515 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD2801 Approved
0.7514 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6099 Approved
0.75 Intermediate Similarity NPD7054 Approved
0.75 Intermediate Similarity NPD7411 Suspended
0.75 Intermediate Similarity NPD6100 Approved
0.75 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7685 Pre-registration
0.7471 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD8150 Discontinued
0.7457 Intermediate Similarity NPD7074 Phase 3
0.7457 Intermediate Similarity NPD7472 Approved
0.7456 Intermediate Similarity NPD6959 Discontinued
0.7455 Intermediate Similarity NPD1934 Approved
0.7453 Intermediate Similarity NPD2533 Approved
0.7453 Intermediate Similarity NPD2534 Approved
0.7453 Intermediate Similarity NPD2532 Approved
0.7436 Intermediate Similarity NPD7033 Discontinued
0.7429 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD3750 Approved
0.7421 Intermediate Similarity NPD4110 Phase 3
0.7421 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD7229 Phase 3
0.741 Intermediate Similarity NPD1465 Phase 2
0.7407 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD5494 Approved
0.7391 Intermediate Similarity NPD6799 Approved
0.7389 Intermediate Similarity NPD2438 Suspended
0.7386 Intermediate Similarity NPD8313 Approved
0.7386 Intermediate Similarity NPD8312 Approved
0.7378 Intermediate Similarity NPD3226 Approved
0.7371 Intermediate Similarity NPD7251 Discontinued
0.7366 Intermediate Similarity NPD7435 Discontinued
0.7362 Intermediate Similarity NPD5403 Approved
0.7362 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD5124 Phase 1
0.7346 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD5401 Approved
0.7341 Intermediate Similarity NPD3818 Discontinued
0.7338 Intermediate Similarity NPD8032 Phase 2
0.733 Intermediate Similarity NPD7808 Phase 3
0.7326 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD3748 Approved
0.7321 Intermediate Similarity NPD7768 Phase 2
0.7315 Intermediate Similarity NPD1608 Approved
0.7314 Intermediate Similarity NPD6797 Phase 2
0.729 Intermediate Similarity NPD4140 Approved
0.7285 Intermediate Similarity NPD2797 Approved
0.7278 Intermediate Similarity NPD2935 Discontinued
0.7278 Intermediate Similarity NPD2796 Approved
0.7273 Intermediate Similarity NPD3268 Approved
0.7273 Intermediate Similarity NPD3764 Approved
0.7244 Intermediate Similarity NPD230 Phase 1
0.7233 Intermediate Similarity NPD5763 Approved
0.7233 Intermediate Similarity NPD5762 Approved
0.7233 Intermediate Similarity NPD7266 Discontinued
0.723 Intermediate Similarity NPD1778 Approved
0.7229 Intermediate Similarity NPD7028 Phase 2
0.7226 Intermediate Similarity NPD6663 Approved
0.7222 Intermediate Similarity NPD7236 Approved
0.7219 Intermediate Similarity NPD3225 Approved
0.7219 Intermediate Similarity NPD1283 Approved
0.7215 Intermediate Similarity NPD1510 Phase 2
0.7204 Intermediate Similarity NPD6776 Approved
0.7204 Intermediate Similarity NPD6781 Approved
0.7204 Intermediate Similarity NPD6777 Approved
0.7204 Intermediate Similarity NPD6782 Approved
0.7204 Intermediate Similarity NPD6778 Approved
0.7204 Intermediate Similarity NPD6779 Approved
0.7204 Intermediate Similarity NPD6780 Approved
0.7202 Intermediate Similarity NPD5760 Phase 2
0.7202 Intermediate Similarity NPD5761 Phase 2
0.719 Intermediate Similarity NPD5736 Approved
0.7188 Intermediate Similarity NPD4534 Discontinued
0.7186 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD2979 Phase 3
0.7179 Intermediate Similarity NPD4060 Phase 1
0.7178 Intermediate Similarity NPD1511 Approved
0.7176 Intermediate Similarity NPD3749 Approved
0.7169 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD5691 Approved
0.7143 Intermediate Similarity NPD1652 Phase 2
0.7143 Intermediate Similarity NPD6674 Discontinued
0.7135 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7874 Approved
0.7134 Intermediate Similarity NPD5735 Approved
0.7125 Intermediate Similarity NPD2346 Discontinued
0.7125 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD7157 Approved
0.7118 Intermediate Similarity NPD3882 Suspended
0.7115 Intermediate Similarity NPD4062 Phase 3
0.7114 Intermediate Similarity NPD4626 Approved
0.7114 Intermediate Similarity NPD17 Approved
0.7108 Intermediate Similarity NPD1653 Approved
0.7108 Intermediate Similarity NPD7239 Suspended
0.7107 Intermediate Similarity NPD2799 Discontinued
0.7105 Intermediate Similarity NPD8651 Approved
0.7098 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD7783 Phase 2
0.7097 Intermediate Similarity NPD3027 Phase 3
0.7091 Intermediate Similarity NPD1512 Approved
0.709 Intermediate Similarity NPD7698 Approved
0.709 Intermediate Similarity NPD7697 Approved
0.709 Intermediate Similarity NPD7696 Phase 3
0.7086 Intermediate Similarity NPD3972 Approved
0.7083 Intermediate Similarity NPD6386 Approved
0.7083 Intermediate Similarity NPD8151 Discontinued
0.7083 Intermediate Similarity NPD6385 Approved
0.7083 Intermediate Similarity NPD6677 Suspended
0.7081 Intermediate Similarity NPD2424 Discontinued
0.7081 Intermediate Similarity NPD1549 Phase 2
0.7079 Intermediate Similarity NPD6559 Discontinued
0.7079 Intermediate Similarity NPD8368 Discontinued
0.7059 Intermediate Similarity NPD3267 Approved
0.7059 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3266 Approved
0.7053 Intermediate Similarity NPD7871 Phase 2
0.7053 Intermediate Similarity NPD7870 Phase 2
0.7051 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD2313 Discontinued
0.7051 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD2973 Approved
0.7043 Intermediate Similarity NPD2975 Approved
0.7043 Intermediate Similarity NPD2974 Approved
0.7037 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6823 Phase 2
0.7032 Intermediate Similarity NPD4908 Phase 1
0.7031 Intermediate Similarity NPD7701 Phase 2
0.702 Intermediate Similarity NPD1281 Approved
0.7019 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD6004 Phase 3
0.7019 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD6005 Phase 3
0.7019 Intermediate Similarity NPD6002 Phase 3
0.7012 Intermediate Similarity NPD6652 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD4198 Discontinued
0.7006 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7680 Approved
0.7 Intermediate Similarity NPD4308 Phase 3
0.6995 Remote Similarity NPD8360 Approved
0.6995 Remote Similarity NPD8435 Approved
0.6995 Remote Similarity NPD8361 Approved
0.6984 Remote Similarity NPD2494 Approved
0.6984 Remote Similarity NPD2493 Approved
0.6983 Remote Similarity NPD6765 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