Structure

Physi-Chem Properties

Molecular Weight:  754.1
Volume:  657.801
LogP:  2.585
LogD:  1.992
LogS:  -4.113
# Rotatable Bonds:  3
TPSA:  183.06
# H-Bond Aceptor:  14
# H-Bond Donor:  5
# Rings:  12
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.213
Synthetic Accessibility Score:  5.884
Fsp3:  0.469
Lipinski Rule-of-5:  Rejected
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:  -6.002
MDCK Permeability:  7.451633791788481e-06
Pgp-inhibitor:  0.145
Pgp-substrate:  0.984
Human Intestinal Absorption (HIA):  0.418
20% Bioavailability (F20%):  0.907
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.172
Plasma Protein Binding (PPB):  75.48265075683594%
Volume Distribution (VD):  0.955
Pgp-substrate:  6.598354339599609%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.082
CYP2C19-inhibitor:  0.938
CYP2C19-substrate:  0.934
CYP2C9-inhibitor:  0.976
CYP2C9-substrate:  0.118
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.051
CYP3A4-inhibitor:  0.894
CYP3A4-substrate:  0.99

ADMET: Excretion

Clearance (CL):  5.796
Half-life (T1/2):  0.01

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  0.138
Drug-inuced Liver Injury (DILI):  0.985
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.754
Maximum Recommended Daily Dose:  0.141
Skin Sensitization:  0.917
Carcinogencity:  0.444
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.285

Download Data

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

  Natural Product: NPC475359

Natural Product ID:  NPC475359
Common Name*:   Verticillin F
IUPAC Name:   n.a.
Synonyms:   Verticillin F
Standard InCHIKey:  YMYVOCNKQGGHNP-FMVGARMTSA-N
Standard InCHI:  InChI=1S/C32H30N6O8S4/c1-13(39)29-25(45)37-21-27(15-9-5-7-11-17(15)33-21,19(41)31(37,49-47-29)23(43)35(29)3)28-16-10-6-8-12-18(16)34-22(28)38-26(46)30(14(2)40)36(4)24(44)32(38,20(28)42)50-48-30/h5-13,19-22,33-34,39,41-42H,1-4H3/t13?,19-,20-,21+,22+,27+,28+,29-,30-,31-,32-/m0/s1
SMILES:  CC([C@@]12SS[C@@]3(C(=O)N1C)N(C2=O)[C@H]1Nc2c([C@]1([C@@H]3O)[C@@]13c4ccccc4N[C@@H]1N1[C@@]4([C@H]3O)SS[C@@](C1=O)(N(C4=O)C)C(=O)C)cccc2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504253
PubChem CID:   44566359
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0001733] Pyrroloindoles

*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
NPO32753 gliocladium catenulatum Species n.a. Eukaryota n.a. n.a. n.a. PMID[10346956]

☑ 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
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 23.0 mm PMID[458649]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 11.0 mm PMID[458649]

☑ 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 NPC475359 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 NPC191817
0.9786 High Similarity NPC475259
0.9785 High Similarity NPC470490
0.9731 High Similarity NPC477181
0.9731 High Similarity NPC477178
0.9731 High Similarity NPC477180
0.9731 High Similarity NPC254850
0.9681 High Similarity NPC471945
0.9681 High Similarity NPC471950
0.9677 High Similarity NPC477179
0.9524 High Similarity NPC470488
0.9471 High Similarity NPC477173
0.9471 High Similarity NPC477174
0.9424 High Similarity NPC471946
0.9424 High Similarity NPC471951
0.9271 High Similarity NPC470491
0.9032 High Similarity NPC128582
0.8918 High Similarity NPC470489
0.7808 Intermediate Similarity NPC475859
0.7808 Intermediate Similarity NPC475969
0.7763 Intermediate Similarity NPC470730
0.7763 Intermediate Similarity NPC477175
0.776 Intermediate Similarity NPC242269
0.7692 Intermediate Similarity NPC165743
0.766 Intermediate Similarity NPC276085
0.7633 Intermediate Similarity NPC471436
0.7588 Intermediate Similarity NPC307396
0.7574 Intermediate Similarity NPC276430
0.7568 Intermediate Similarity NPC474877
0.7568 Intermediate Similarity NPC477177
0.7523 Intermediate Similarity NPC470729
0.7523 Intermediate Similarity NPC477176
0.75 Intermediate Similarity NPC63279
0.7467 Intermediate Similarity NPC297642
0.7409 Intermediate Similarity NPC312942
0.7409 Intermediate Similarity NPC327095
0.7327 Intermediate Similarity NPC259626
0.732 Intermediate Similarity NPC471124
0.7277 Intermediate Similarity NPC2933
0.724 Intermediate Similarity NPC222029
0.7228 Intermediate Similarity NPC256288
0.7222 Intermediate Similarity NPC285622
0.722 Intermediate Similarity NPC40455
0.7215 Intermediate Similarity NPC470731
0.7202 Intermediate Similarity NPC471122
0.7171 Intermediate Similarity NPC229484
0.7168 Intermediate Similarity NPC297862
0.7165 Intermediate Similarity NPC309531
0.7165 Intermediate Similarity NPC472102
0.715 Intermediate Similarity NPC329833
0.7143 Intermediate Similarity NPC162440
0.7136 Intermediate Similarity NPC292675
0.7122 Intermediate Similarity NPC473615
0.7065 Intermediate Similarity NPC476441
0.7059 Intermediate Similarity NPC477159
0.7056 Intermediate Similarity NPC472106
0.7035 Intermediate Similarity NPC19170
0.699 Remote Similarity NPC68650
0.6982 Remote Similarity NPC470732
0.6971 Remote Similarity NPC284706
0.6968 Remote Similarity NPC471663
0.6959 Remote Similarity NPC225400
0.6954 Remote Similarity NPC472101
0.6954 Remote Similarity NPC472120
0.6952 Remote Similarity NPC470301
0.695 Remote Similarity NPC472118
0.6934 Remote Similarity NPC472540
0.6934 Remote Similarity NPC470787
0.6934 Remote Similarity NPC472539
0.6927 Remote Similarity NPC472538
0.6927 Remote Similarity NPC470786
0.6927 Remote Similarity NPC471155
0.6916 Remote Similarity NPC106118
0.6912 Remote Similarity NPC475094
0.6901 Remote Similarity NPC472542
0.6901 Remote Similarity NPC90967
0.6901 Remote Similarity NPC472541
0.6901 Remote Similarity NPC471199
0.6895 Remote Similarity NPC270241
0.6891 Remote Similarity NPC66936
0.6881 Remote Similarity NPC476425
0.6869 Remote Similarity NPC176983
0.6869 Remote Similarity NPC286871
0.685 Remote Similarity NPC214960
0.685 Remote Similarity NPC279527
0.6847 Remote Similarity NPC470548
0.6845 Remote Similarity NPC476428
0.6842 Remote Similarity NPC476817
0.6802 Remote Similarity NPC113946
0.6798 Remote Similarity NPC473880
0.6784 Remote Similarity NPC472117
0.6784 Remote Similarity NPC272174
0.6766 Remote Similarity NPC472115
0.6766 Remote Similarity NPC472114
0.6765 Remote Similarity NPC475097
0.6754 Remote Similarity NPC474896
0.6742 Remote Similarity NPC285192
0.6741 Remote Similarity NPC473006
0.6729 Remote Similarity NPC34717
0.6728 Remote Similarity NPC475489
0.6726 Remote Similarity NPC471197
0.6725 Remote Similarity NPC253987
0.6725 Remote Similarity NPC31097
0.6716 Remote Similarity NPC177261
0.6716 Remote Similarity NPC473743
0.6715 Remote Similarity NPC166169
0.6708 Remote Similarity NPC14812
0.6698 Remote Similarity NPC22689
0.6698 Remote Similarity NPC105055
0.6696 Remote Similarity NPC471198
0.6667 Remote Similarity NPC29285
0.6667 Remote Similarity NPC476095
0.6649 Remote Similarity NPC471123
0.6637 Remote Similarity NPC107077
0.6637 Remote Similarity NPC223791
0.6636 Remote Similarity NPC295548
0.6635 Remote Similarity NPC286994
0.6634 Remote Similarity NPC251212
0.6634 Remote Similarity NPC139085
0.6634 Remote Similarity NPC475420
0.6634 Remote Similarity NPC214626
0.6633 Remote Similarity NPC469898
0.6623 Remote Similarity NPC248601
0.662 Remote Similarity NPC473298
0.6618 Remote Similarity NPC476326
0.6615 Remote Similarity NPC109787
0.6604 Remote Similarity NPC181928
0.6588 Remote Similarity NPC52262
0.6585 Remote Similarity NPC355
0.6574 Remote Similarity NPC221687
0.6569 Remote Similarity NPC301501
0.6566 Remote Similarity NPC478076
0.6562 Remote Similarity NPC162860
0.6555 Remote Similarity NPC478028
0.6524 Remote Similarity NPC122886
0.6522 Remote Similarity NPC219397
0.6517 Remote Similarity NPC473003
0.6502 Remote Similarity NPC329932
0.6502 Remote Similarity NPC313757
0.65 Remote Similarity NPC478029
0.6497 Remote Similarity NPC473329
0.6492 Remote Similarity NPC469560
0.649 Remote Similarity NPC469900
0.6488 Remote Similarity NPC63047
0.6488 Remote Similarity NPC475248
0.6488 Remote Similarity NPC473000
0.6488 Remote Similarity NPC469452
0.6488 Remote Similarity NPC469451
0.6483 Remote Similarity NPC223242
0.6473 Remote Similarity NPC54420
0.6473 Remote Similarity NPC469450
0.6471 Remote Similarity NPC471512
0.6468 Remote Similarity NPC97100
0.6468 Remote Similarity NPC473375
0.6462 Remote Similarity NPC97584
0.6462 Remote Similarity NPC302235
0.6459 Remote Similarity NPC473001
0.6453 Remote Similarity NPC282339
0.6453 Remote Similarity NPC472121
0.6453 Remote Similarity NPC469741
0.6453 Remote Similarity NPC99632
0.6436 Remote Similarity NPC469902
0.6435 Remote Similarity NPC244425
0.6435 Remote Similarity NPC15384
0.6432 Remote Similarity NPC473002
0.6429 Remote Similarity NPC139373
0.6429 Remote Similarity NPC264589
0.6429 Remote Similarity NPC99043
0.6429 Remote Similarity NPC218594
0.6418 Remote Similarity NPC324850
0.6414 Remote Similarity NPC318086
0.6411 Remote Similarity NPC129624
0.6409 Remote Similarity NPC52557
0.6404 Remote Similarity NPC225319
0.6404 Remote Similarity NPC315368
0.6398 Remote Similarity NPC145754
0.639 Remote Similarity NPC131977
0.6381 Remote Similarity NPC260075
0.6373 Remote Similarity NPC85651
0.6372 Remote Similarity NPC14994
0.6368 Remote Similarity NPC473005
0.6368 Remote Similarity NPC155143
0.6355 Remote Similarity NPC469901
0.6355 Remote Similarity NPC36495
0.6344 Remote Similarity NPC252794
0.6344 Remote Similarity NPC477160
0.6336 Remote Similarity NPC477714
0.6335 Remote Similarity NPC100863
0.6329 Remote Similarity NPC469904
0.6327 Remote Similarity NPC478075
0.6323 Remote Similarity NPC475506
0.6318 Remote Similarity NPC329295
0.6316 Remote Similarity NPC96901
0.6311 Remote Similarity NPC24661
0.6311 Remote Similarity NPC44357
0.6309 Remote Similarity NPC475609
0.6305 Remote Similarity NPC104345
0.6296 Remote Similarity NPC285841
0.6293 Remote Similarity NPC477715
0.6293 Remote Similarity NPC238945

  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 NPC475359 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
0.7574 Intermediate Similarity NPD8240 Discontinued
0.6732 Remote Similarity NPD8022 Clinical (unspecified phase)
0.6717 Remote Similarity NPD8630 Approved
0.6667 Remote Similarity NPD6557 Phase 2
0.665 Remote Similarity NPD4120 Approved
0.665 Remote Similarity NPD4121 Phase 3
0.6635 Remote Similarity NPD6878 Phase 2
0.6635 Remote Similarity NPD6879 Phase 2
0.6616 Remote Similarity NPD5741 Approved
0.6616 Remote Similarity NPD5742 Approved
0.6616 Remote Similarity NPD5743 Approved
0.6604 Remote Similarity NPD8103 Clinical (unspecified phase)
0.651 Remote Similarity NPD3625 Discontinued
0.6447 Remote Similarity NPD5942 Approved
0.6447 Remote Similarity NPD5941 Approved
0.6443 Remote Similarity NPD5024 Approved
0.6432 Remote Similarity NPD7595 Discontinued
0.64 Remote Similarity NPD8322 Phase 2
0.6384 Remote Similarity NPD8114 Approved
0.6384 Remote Similarity NPD8115 Approved
0.6355 Remote Similarity NPD7599 Phase 2
0.6351 Remote Similarity NPD5775 Approved
0.6351 Remote Similarity NPD5774 Approved
0.6305 Remote Similarity NPD5715 Clinical (unspecified phase)
0.6278 Remote Similarity NPD6805 Discontinued
0.6277 Remote Similarity NPD7970 Approved
0.6277 Remote Similarity NPD7971 Clinical (unspecified phase)
0.6276 Remote Similarity NPD7824 Approved
0.6266 Remote Similarity NPD7953 Approved
0.6266 Remote Similarity NPD7789 Approved
0.6266 Remote Similarity NPD7951 Approved
0.6266 Remote Similarity NPD7952 Approved
0.6266 Remote Similarity NPD7791 Approved
0.6266 Remote Similarity NPD7950 Approved
0.6266 Remote Similarity NPD7790 Approved
0.6261 Remote Similarity NPD7594 Clinical (unspecified phase)
0.625 Remote Similarity NPD7890 Discontinued
0.6245 Remote Similarity NPD7809 Clinical (unspecified phase)
0.6232 Remote Similarity NPD4976 Discontinued
0.62 Remote Similarity NPD4682 Phase 2
0.6199 Remote Similarity NPD4602 Approved
0.6192 Remote Similarity NPD7730 Approved
0.6192 Remote Similarity NPD7731 Approved
0.619 Remote Similarity NPD5727 Clinical (unspecified phase)
0.6188 Remote Similarity NPD8400 Approved
0.6188 Remote Similarity NPD8401 Approved
0.6188 Remote Similarity NPD8402 Approved
0.6184 Remote Similarity NPD3790 Phase 2
0.6178 Remote Similarity NPD7817 Phase 1
0.6176 Remote Similarity NPD7105 Phase 1
0.6165 Remote Similarity NPD7600 Phase 2
0.6162 Remote Similarity NPD5918 Discontinued
0.6161 Remote Similarity NPD5997 Discontinued
0.6151 Remote Similarity NPD8289 Discontinued
0.615 Remote Similarity NPD7587 Clinical (unspecified phase)
0.6147 Remote Similarity NPD7683 Discontinued
0.6133 Remote Similarity NPD4600 Approved
0.6133 Remote Similarity NPD4601 Approved
0.6123 Remote Similarity NPD7205 Discontinued
0.6119 Remote Similarity NPD4432 Discontinued
0.6117 Remote Similarity NPD4514 Approved
0.6114 Remote Similarity NPD8493 Clinical (unspecified phase)
0.6109 Remote Similarity NPD7271 Approved
0.6109 Remote Similarity NPD6200 Clinical (unspecified phase)
0.6103 Remote Similarity NPD6358 Phase 2
0.61 Remote Similarity NPD7781 Approved
0.61 Remote Similarity NPD7780 Approved
0.6093 Remote Similarity NPD4330 Approved
0.6093 Remote Similarity NPD4329 Approved
0.6075 Remote Similarity NPD3792 Approved
0.6068 Remote Similarity NPD7735 Clinical (unspecified phase)
0.6066 Remote Similarity NPD7968 Clinical (unspecified phase)
0.6063 Remote Similarity NPD5077 Approved
0.6063 Remote Similarity NPD5076 Approved
0.6056 Remote Similarity NPD6316 Clinical (unspecified phase)
0.6051 Remote Similarity NPD6102 Clinical (unspecified phase)
0.605 Remote Similarity NPD7785 Clinical (unspecified phase)
0.6045 Remote Similarity NPD7444 Clinical (unspecified phase)
0.6044 Remote Similarity NPD5856 Discontinued
0.6036 Remote Similarity NPD7570 Approved
0.6036 Remote Similarity NPD7569 Approved
0.6035 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6035 Remote Similarity NPD7727 Phase 2
0.6035 Remote Similarity NPD7973 Discontinued
0.603 Remote Similarity NPD6301 Phase 2
0.6026 Remote Similarity NPD8272 Phase 2
0.602 Remote Similarity NPD6294 Approved
0.602 Remote Similarity NPD3509 Approved
0.602 Remote Similarity NPD6295 Approved
0.602 Remote Similarity NPD3510 Approved
0.6019 Remote Similarity NPD3989 Phase 3
0.601 Remote Similarity NPD5748 Phase 2
0.601 Remote Similarity NPD5581 Approved
0.6 Remote Similarity NPD6260 Discontinued
0.6 Remote Similarity NPD3828 Approved
0.5992 Remote Similarity NPD6165 Phase 2
0.5992 Remote Similarity NPD6164 Phase 2
0.5991 Remote Similarity NPD5042 Phase 1
0.5991 Remote Similarity NPD3990 Phase 3
0.5982 Remote Similarity NPD7944 Discontinued
0.5974 Remote Similarity NPD6518 Discontinued
0.5973 Remote Similarity NPD5197 Approved
0.5973 Remote Similarity NPD5194 Approved
0.5973 Remote Similarity NPD5196 Approved
0.5962 Remote Similarity NPD4393 Approved
0.5962 Remote Similarity NPD33 Approved
0.5957 Remote Similarity NPD7712 Clinical (unspecified phase)
0.5957 Remote Similarity NPD6644 Discontinued
0.5951 Remote Similarity NPD8315 Phase 1
0.5949 Remote Similarity NPD5184 Approved
0.5949 Remote Similarity NPD4153 Approved
0.5949 Remote Similarity NPD5182 Approved
0.5949 Remote Similarity NPD5185 Approved
0.5948 Remote Similarity NPD4882 Clinical (unspecified phase)
0.5948 Remote Similarity NPD7666 Phase 3
0.5948 Remote Similarity NPD7665 Phase 2
0.5943 Remote Similarity NPD2037 Approved
0.5942 Remote Similarity NPD6395 Phase 2
0.5942 Remote Similarity NPD1663 Discontinued
0.5942 Remote Similarity NPD6396 Clinical (unspecified phase)
0.5938 Remote Similarity NPD3040 Approved
0.5935 Remote Similarity NPD7854 Phase 2
0.5934 Remote Similarity NPD7717 Approved
0.5934 Remote Similarity NPD7716 Approved
0.5934 Remote Similarity NPD6173 Approved
0.5929 Remote Similarity NPD8250 Phase 2
0.5926 Remote Similarity NPD5600 Discontinued
0.5922 Remote Similarity NPD5639 Clinical (unspecified phase)
0.5918 Remote Similarity NPD7552 Discontinued
0.5917 Remote Similarity NPD7149 Clinical (unspecified phase)
0.5911 Remote Similarity NPD2426 Clinical (unspecified phase)
0.5909 Remote Similarity NPD7728 Clinical (unspecified phase)
0.5907 Remote Similarity NPD5263 Approved
0.5907 Remote Similarity NPD7662 Clinical (unspecified phase)
0.5907 Remote Similarity NPD3423 Phase 2
0.5907 Remote Similarity NPD3422 Phase 3
0.5907 Remote Similarity NPD7543 Phase 2
0.5907 Remote Similarity NPD6613 Clinical (unspecified phase)
0.5907 Remote Similarity NPD5466 Approved
0.5904 Remote Similarity NPD7677 Discontinued
0.5903 Remote Similarity NPD7995 Phase 2
0.5901 Remote Similarity NPD8025 Phase 2
0.5895 Remote Similarity NPD6238 Discontinued
0.589 Remote Similarity NPD7557 Clinical (unspecified phase)
0.5888 Remote Similarity NPD3824 Phase 1
0.5888 Remote Similarity NPD6073 Approved
0.5882 Remote Similarity NPD8271 Discontinued
0.5882 Remote Similarity NPD8000 Clinical (unspecified phase)
0.588 Remote Similarity NPD4091 Approved
0.5877 Remote Similarity NPD7621 Clinical (unspecified phase)
0.5877 Remote Similarity NPD7308 Discontinued
0.5874 Remote Similarity NPD7617 Discontinued
0.5872 Remote Similarity NPD7470 Discontinued
0.5872 Remote Similarity NPD3227 Phase 2
0.5871 Remote Similarity NPD4430 Phase 2
0.5871 Remote Similarity NPD3508 Approved
0.5871 Remote Similarity NPD2820 Phase 3
0.5871 Remote Similarity NPD5264 Approved
0.5871 Remote Similarity NPD5265 Approved
0.5865 Remote Similarity NPD7118 Clinical (unspecified phase)
0.5864 Remote Similarity NPD8241 Phase 2
0.5864 Remote Similarity NPD6792 Phase 3
0.5862 Remote Similarity NPD7001 Phase 3
0.5859 Remote Similarity NPD4126 Approved
0.5859 Remote Similarity NPD5318 Discontinued
0.5857 Remote Similarity NPD7432 Phase 2
0.5856 Remote Similarity NPD6484 Approved
0.5856 Remote Similarity NPD6483 Approved
0.5855 Remote Similarity NPD4520 Approved
0.5853 Remote Similarity NPD3991 Approved
0.5853 Remote Similarity NPD3993 Approved
0.5853 Remote Similarity NPD3994 Approved
0.5853 Remote Similarity NPD3995 Approved
0.5853 Remote Similarity NPD3992 Approved
0.5853 Remote Similarity NPD4092 Approved
0.5853 Remote Similarity NPD3449 Discontinued
0.5853 Remote Similarity NPD3996 Approved
0.5853 Remote Similarity NPD4317 Approved
0.5852 Remote Similarity NPD6519 Phase 2
0.5848 Remote Similarity NPD2327 Clinical (unspecified phase)
0.5848 Remote Similarity NPD5504 Discontinued
0.5847 Remote Similarity NPD7551 Clinical (unspecified phase)
0.5847 Remote Similarity NPD7550 Clinical (unspecified phase)
0.5845 Remote Similarity NPD2790 Discontinued
0.5844 Remote Similarity NPD7821 Clinical (unspecified phase)
0.5841 Remote Similarity NPD7619 Phase 3
0.5841 Remote Similarity NPD7618 Phase 3
0.584 Remote Similarity NPD6596 Phase 2
0.5838 Remote Similarity NPD2791 Discontinued
0.5837 Remote Similarity NPD6021 Clinical (unspecified phase)
0.5837 Remote Similarity NPD6838 Clinical (unspecified phase)
0.5833 Remote Similarity NPD7168 Phase 3
0.583 Remote Similarity NPD7664 Discontinued
0.583 Remote Similarity NPD7855 Clinical (unspecified phase)
0.5829 Remote Similarity NPD8351 Phase 2
0.5826 Remote Similarity NPD3997 Approved
0.5826 Remote Similarity NPD3998 Approved
0.5826 Remote Similarity NPD3999 Approved
0.5826 Remote Similarity NPD3782 Discontinued
0.5822 Remote Similarity NPD3479 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