Structure

Physi-Chem Properties

Molecular Weight:  681.27
Volume:  681.101
LogP:  3.317
LogD:  2.313
LogS:  -4.019
# Rotatable Bonds:  9
TPSA:  153.1
# H-Bond Aceptor:  12
# H-Bond Donor:  0
# Rings:  7
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.193
Synthetic Accessibility Score:  5.589
Fsp3:  0.447
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:  -5.391
MDCK Permeability:  2.5853109036688693e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.997
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.195
Plasma Protein Binding (PPB):  88.74972534179688%
Volume Distribution (VD):  2.576
Pgp-substrate:  9.564433097839355%

ADMET: Metabolism

CYP1A2-inhibitor:  0.46
CYP1A2-substrate:  0.104
CYP2C19-inhibitor:  0.753
CYP2C19-substrate:  0.091
CYP2C9-inhibitor:  0.614
CYP2C9-substrate:  0.097
CYP2D6-inhibitor:  0.965
CYP2D6-substrate:  0.076
CYP3A4-inhibitor:  0.982
CYP3A4-substrate:  0.388

ADMET: Excretion

Clearance (CL):  11.503
Half-life (T1/2):  0.68

ADMET: Toxicity

hERG Blockers:  0.847
Human Hepatotoxicity (H-HT):  0.112
Drug-inuced Liver Injury (DILI):  0.978
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.437
Maximum Recommended Daily Dose:  0.874
Skin Sensitization:  0.939
Carcinogencity:  0.061
Eye Corrosion:  0.003
Eye Irritation:  0.086
Respiratory Toxicity:  0.201

Download Data

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

  Natural Product: NPC91125

Natural Product ID:  NPC91125
Common Name*:   Barbatine B
IUPAC Name:   [(1S,3R,4aR,5S,6R,6aR,10aS,10bS)-4a,6a,7,10b-tetramethyl-2'-oxo-5,6-bis(pyridine-3-carbonyloxy)spiro[2,5,6,9,10,10a-hexahydro-1H-benzo[f]chromene-3,4'-oxolane]-1-yl] pyridine-3-carboxylate
Synonyms:  
Standard InCHIKey:  JSOPCSZTJHEWCM-YBNGNYGTSA-N
Standard InCHI:  InChI=1S/C38H39N3O9/c1-23-9-5-13-27-35(23,2)30(48-33(44)25-11-7-15-40-20-25)31(49-34(45)26-12-8-16-41-21-26)37(4)36(27,3)28(17-38(50-37)18-29(42)46-22-38)47-32(43)24-10-6-14-39-19-24/h6-12,14-16,19-21,27-28,30-31H,5,13,17-18,22H2,1-4H3/t27-,28-,30-,31-,35-,36-,37-,38+/m0/s1
SMILES:  CC1=CCC[C@H]2[C@@]1(C)[C@H]([C@@H]([C@@]1(C)[C@]2(C)[C@H](C[C@]2(CC(=O)OC2)O1)OC(=O)c1cccnc1)OC(=O)c1cccnc1)OC(=O)c1cccnc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3577097
PubChem CID:   44604690
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[16755060]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[17666848]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[18239311]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19785430]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19962306]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20078074]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota whole plants Nanning District, Guangxi Province, China 2012-Sep PMID[25647077]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota aerial parts Seoul, Korea n.a. PMID[26331882]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16039 Scutellaria barbata 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
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 Inhibition < 50.0 % PMID[448241]

☑ 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 NPC91125 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
0.9803 High Similarity NPC26881
0.9706 High Similarity NPC477899
0.9706 High Similarity NPC477900
0.9704 High Similarity NPC235364
0.9606 High Similarity NPC477901
0.9567 High Similarity NPC477906
0.9463 High Similarity NPC477903
0.936 High Similarity NPC264674
0.933 High Similarity NPC124029
0.9238 High Similarity NPC211920
0.9234 High Similarity NPC477902
0.913 High Similarity NPC212768
0.913 High Similarity NPC473089
0.913 High Similarity NPC75600
0.913 High Similarity NPC6576
0.913 High Similarity NPC473115
0.913 High Similarity NPC158020
0.9087 High Similarity NPC472555
0.9078 High Similarity NPC4421
0.899 High Similarity NPC206343
0.899 High Similarity NPC477908
0.8957 High Similarity NPC477911
0.8957 High Similarity NPC127720
0.8957 High Similarity NPC127026
0.8947 High Similarity NPC62367
0.893 High Similarity NPC96801
0.893 High Similarity NPC150698
0.8915 High Similarity NPC471980
0.8905 High Similarity NPC301368
0.8905 High Similarity NPC216428
0.8905 High Similarity NPC84815
0.8894 High Similarity NPC327769
0.8879 High Similarity NPC475601
0.8873 High Similarity NPC328154
0.8852 High Similarity NPC42678
0.8852 High Similarity NPC477909
0.8852 High Similarity NPC477907
0.8821 High Similarity NPC477912
0.881 High Similarity NPC6981
0.881 High Similarity NPC471016
0.8798 High Similarity NPC472553
0.8779 High Similarity NPC477788
0.8768 High Similarity NPC144779
0.8768 High Similarity NPC294579
0.8762 High Similarity NPC470306
0.872 High Similarity NPC471014
0.872 High Similarity NPC475408
0.8716 High Similarity NPC469748
0.87 High Similarity NPC475648
0.867 High Similarity NPC475596
0.867 High Similarity NPC316841
0.867 High Similarity NPC475303
0.8657 High Similarity NPC148860
0.8654 High Similarity NPC304179
0.8654 High Similarity NPC472550
0.8654 High Similarity NPC48042
0.8649 High Similarity NPC253482
0.8636 High Similarity NPC35208
0.863 High Similarity NPC213143
0.863 High Similarity NPC30456
0.8626 High Similarity NPC319128
0.8618 High Similarity NPC475600
0.8618 High Similarity NPC228377
0.8618 High Similarity NPC87152
0.8618 High Similarity NPC476110
0.8618 High Similarity NPC328186
0.8618 High Similarity NPC477787
0.8618 High Similarity NPC122968
0.8618 High Similarity NPC475631
0.8585 High Similarity NPC477910
0.8578 High Similarity NPC470486
0.8578 High Similarity NPC471190
0.8578 High Similarity NPC471977
0.8578 High Similarity NPC475644
0.8565 High Similarity NPC250807
0.8565 High Similarity NPC76565
0.8565 High Similarity NPC57797
0.8552 High Similarity NPC475406
0.8552 High Similarity NPC475426
0.8551 High Similarity NPC289086
0.8538 High Similarity NPC228331
0.8525 High Similarity NPC475498
0.8525 High Similarity NPC475137
0.8525 High Similarity NPC473850
0.8517 High Similarity NPC63041
0.8514 High Similarity NPC327904
0.8514 High Similarity NPC38959
0.8505 High Similarity NPC319556
0.85 High Similarity NPC473689
0.85 High Similarity NPC292416
0.8498 Intermediate Similarity NPC193361
0.8498 Intermediate Similarity NPC30570
0.8498 Intermediate Similarity NPC62844
0.8491 Intermediate Similarity NPC165837
0.8486 Intermediate Similarity NPC473506
0.8462 Intermediate Similarity NPC244839
0.8462 Intermediate Similarity NPC320324
0.8462 Intermediate Similarity NPC319880
0.8447 Intermediate Similarity NPC146824
0.8443 Intermediate Similarity NPC323551
0.8443 Intermediate Similarity NPC280473
0.8423 Intermediate Similarity NPC237702
0.8423 Intermediate Similarity NPC238278
0.8419 Intermediate Similarity NPC187494
0.8411 Intermediate Similarity NPC207531
0.8409 Intermediate Similarity NPC475362
0.8404 Intermediate Similarity NPC41724
0.8404 Intermediate Similarity NPC51008
0.8386 Intermediate Similarity NPC170751
0.8372 Intermediate Similarity NPC162812
0.8364 Intermediate Similarity NPC285411
0.8364 Intermediate Similarity NPC14116
0.8357 Intermediate Similarity NPC292517
0.8326 Intermediate Similarity NPC134384
0.8326 Intermediate Similarity NPC311196
0.8273 Intermediate Similarity NPC233727
0.8224 Intermediate Similarity NPC470189
0.8224 Intermediate Similarity NPC40919
0.8208 Intermediate Similarity NPC475835
0.819 Intermediate Similarity NPC10904
0.8186 Intermediate Similarity NPC476467
0.8174 Intermediate Similarity NPC180668
0.8174 Intermediate Similarity NPC471013
0.8174 Intermediate Similarity NPC148896
0.8169 Intermediate Similarity NPC470190
0.8162 Intermediate Similarity NPC471015
0.8151 Intermediate Similarity NPC328928
0.8131 Intermediate Similarity NPC472752
0.8103 Intermediate Similarity NPC475315
0.8103 Intermediate Similarity NPC324619
0.8067 Intermediate Similarity NPC473833
0.806 Intermediate Similarity NPC475533
0.7925 Intermediate Similarity NPC470279
0.7901 Intermediate Similarity NPC471979
0.7899 Intermediate Similarity NPC326930
0.7899 Intermediate Similarity NPC85879
0.7899 Intermediate Similarity NPC475301
0.7899 Intermediate Similarity NPC53255
0.7895 Intermediate Similarity NPC471004
0.7895 Intermediate Similarity NPC103230
0.7866 Intermediate Similarity NPC13603
0.7851 Intermediate Similarity NPC471978
0.7787 Intermediate Similarity NPC476090
0.7742 Intermediate Similarity NPC309498
0.7577 Intermediate Similarity NPC253314
0.7378 Intermediate Similarity NPC111732
0.7339 Intermediate Similarity NPC320748
0.7339 Intermediate Similarity NPC324245
0.7339 Intermediate Similarity NPC191489
0.7318 Intermediate Similarity NPC32451
0.7318 Intermediate Similarity NPC328559
0.7291 Intermediate Similarity NPC315634
0.7291 Intermediate Similarity NPC88923
0.7291 Intermediate Similarity NPC100734
0.7281 Intermediate Similarity NPC135950
0.7273 Intermediate Similarity NPC79223
0.7227 Intermediate Similarity NPC103361
0.7227 Intermediate Similarity NPC123395
0.7225 Intermediate Similarity NPC318299
0.7215 Intermediate Similarity NPC329024
0.7193 Intermediate Similarity NPC317752
0.7172 Intermediate Similarity NPC107123
0.7162 Intermediate Similarity NPC155792
0.7156 Intermediate Similarity NPC156044
0.7154 Intermediate Similarity NPC476516
0.713 Intermediate Similarity NPC44354
0.7111 Intermediate Similarity NPC238457
0.7104 Intermediate Similarity NPC317672
0.7104 Intermediate Similarity NPC59033
0.7092 Intermediate Similarity NPC284685
0.7081 Intermediate Similarity NPC249614
0.7067 Intermediate Similarity NPC25442
0.7067 Intermediate Similarity NPC12944
0.7061 Intermediate Similarity NPC124313
0.7059 Intermediate Similarity NPC24019
0.7048 Intermediate Similarity NPC470280
0.7025 Intermediate Similarity NPC189903
0.7025 Intermediate Similarity NPC182907
0.7014 Intermediate Similarity NPC109922
0.7012 Intermediate Similarity NPC90875
0.7008 Intermediate Similarity NPC119134
0.7 Intermediate Similarity NPC233334
0.6996 Remote Similarity NPC166722
0.6995 Remote Similarity NPC107287
0.6987 Remote Similarity NPC314834
0.6983 Remote Similarity NPC108342
0.698 Remote Similarity NPC84164
0.698 Remote Similarity NPC207283
0.6972 Remote Similarity NPC478045
0.6971 Remote Similarity NPC70155
0.6967 Remote Similarity NPC191310
0.6963 Remote Similarity NPC471997
0.6955 Remote Similarity NPC471546
0.694 Remote Similarity NPC146976
0.6939 Remote Similarity NPC37473
0.6933 Remote Similarity NPC472762
0.6923 Remote Similarity NPC476517
0.6923 Remote Similarity NPC141385
0.692 Remote Similarity NPC183537
0.6916 Remote Similarity NPC327592

  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 NPC91125 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
0.8028 Intermediate Similarity NPD7396 Approved
0.7833 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD8468 Phase 2
0.7617 Intermediate Similarity NPD7885 Phase 2
0.7617 Intermediate Similarity NPD7886 Phase 2
0.7415 Intermediate Similarity NPD5891 Approved
0.7339 Intermediate Similarity NPD7708 Approved
0.7291 Intermediate Similarity NPD7803 Approved
0.7281 Intermediate Similarity NPD3394 Approved
0.7281 Intermediate Similarity NPD3393 Approved
0.7281 Intermediate Similarity NPD3389 Approved
0.7257 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD7010 Phase 3
0.7143 Intermediate Similarity NPD820 Phase 3
0.7123 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD1483 Discontinued
0.71 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD8325 Phase 3
0.71 Intermediate Similarity NPD8326 Phase 3
0.7092 Intermediate Similarity NPD7956 Approved
0.7092 Intermediate Similarity NPD7955 Approved
0.7085 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD3795 Approved
0.7043 Intermediate Similarity NPD3794 Approved
0.7005 Intermediate Similarity NPD6635 Approved
0.6974 Remote Similarity NPD2509 Approved
0.6974 Remote Similarity NPD2510 Approved
0.6957 Remote Similarity NPD4417 Approved
0.6953 Remote Similarity NPD4989 Phase 2
0.6943 Remote Similarity NPD4506 Discontinued
0.6936 Remote Similarity NPD8479 Phase 2
0.6916 Remote Similarity NPD3947 Discontinued
0.6908 Remote Similarity NPD8350 Clinical (unspecified phase)
0.6907 Remote Similarity NPD4301 Approved
0.6894 Remote Similarity NPD6770 Approved
0.6872 Remote Similarity NPD2121 Clinical (unspecified phase)
0.687 Remote Similarity NPD6529 Discontinued
0.6846 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6844 Remote Similarity NPD6661 Clinical (unspecified phase)
0.683 Remote Similarity NPD8485 Approved
0.6818 Remote Similarity NPD7233 Approved
0.6818 Remote Similarity NPD7234 Approved
0.681 Remote Similarity NPD5475 Discontinued
0.68 Remote Similarity NPD53 Approved
0.68 Remote Similarity NPD7777 Approved
0.68 Remote Similarity NPD7778 Approved
0.68 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6798 Remote Similarity NPD9271 Approved
0.6792 Remote Similarity NPD8289 Discontinued
0.6787 Remote Similarity NPD8063 Discontinued
0.6781 Remote Similarity NPD7069 Discontinued
0.678 Remote Similarity NPD7878 Phase 2
0.6761 Remote Similarity NPD485 Clinical (unspecified phase)
0.6754 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6751 Remote Similarity NPD7404 Approved
0.674 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6723 Remote Similarity NPD3280 Approved
0.6719 Remote Similarity NPD8091 Phase 3
0.6698 Remote Similarity NPD6446 Discontinued
0.6696 Remote Similarity NPD2831 Approved
0.6682 Remote Similarity NPD2336 Approved
0.668 Remote Similarity NPD8409 Suspended
0.6667 Remote Similarity NPD6790 Phase 1
0.664 Remote Similarity NPD3006 Discontinued
0.6638 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6636 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6636 Remote Similarity NPD6641 Approved
0.6636 Remote Similarity NPD6642 Approved
0.6634 Remote Similarity NPD1270 Approved
0.6614 Remote Similarity NPD5482 Discontinued
0.6612 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6609 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6602 Remote Similarity NPD8370 Discontinued
0.6594 Remote Similarity NPD4500 Approved
0.6594 Remote Similarity NPD4501 Approved
0.6582 Remote Similarity NPD7707 Approved
0.6578 Remote Similarity NPD4376 Phase 3
0.6575 Remote Similarity NPD4369 Phase 2
0.6567 Remote Similarity NPD3371 Approved
0.6564 Remote Similarity NPD2307 Discontinued
0.6562 Remote Similarity NPD8360 Approved
0.6562 Remote Similarity NPD8435 Approved
0.6562 Remote Similarity NPD8361 Approved
0.6556 Remote Similarity NPD5147 Discontinued
0.6552 Remote Similarity NPD6987 Phase 1
0.6547 Remote Similarity NPD6257 Clinical (unspecified phase)
0.6537 Remote Similarity NPD4926 Clinical (unspecified phase)
0.653 Remote Similarity NPD3217 Phase 2
0.6529 Remote Similarity NPD8356 Approved
0.6526 Remote Similarity NPD5088 Discontinued
0.6522 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6509 Remote Similarity NPD2511 Approved
0.6508 Remote Similarity NPD8412 Phase 1
0.6504 Remote Similarity NPD4952 Phase 3
0.6502 Remote Similarity NPD107 Approved
0.65 Remote Similarity NPD1926 Approved
0.6496 Remote Similarity NPD8100 Phase 3
0.6492 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6491 Remote Similarity NPD6226 Phase 3
0.6486 Remote Similarity NPD8373 Clinical (unspecified phase)
0.6473 Remote Similarity NPD6955 Clinical (unspecified phase)
0.6473 Remote Similarity NPD6791 Phase 2
0.6471 Remote Similarity NPD8358 Approved
0.6471 Remote Similarity NPD6276 Discontinued
0.6466 Remote Similarity NPD7187 Phase 2
0.6457 Remote Similarity NPD4889 Approved
0.6456 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6453 Remote Similarity NPD4862 Clinical (unspecified phase)
0.645 Remote Similarity NPD4601 Approved
0.645 Remote Similarity NPD6479 Discontinued
0.645 Remote Similarity NPD4600 Approved
0.645 Remote Similarity NPD7862 Clinical (unspecified phase)
0.645 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6447 Remote Similarity NPD4427 Phase 2
0.6445 Remote Similarity NPD6026 Approved
0.6438 Remote Similarity NPD5513 Phase 2
0.6438 Remote Similarity NPD6176 Phase 1
0.6437 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6432 Remote Similarity NPD6568 Discontinued
0.6429 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3816 Phase 1
0.6429 Remote Similarity NPD3815 Phase 1
0.6429 Remote Similarity NPD4375 Approved
0.6426 Remote Similarity NPD4373 Phase 2
0.6423 Remote Similarity NPD8430 Approved
0.642 Remote Similarity NPD8101 Phase 3
0.6417 Remote Similarity NPD5490 Discontinued
0.6415 Remote Similarity NPD2581 Approved
0.6415 Remote Similarity NPD2582 Approved
0.6411 Remote Similarity NPD7688 Phase 1
0.641 Remote Similarity NPD6323 Clinical (unspecified phase)
0.641 Remote Similarity NPD5901 Discontinued
0.6409 Remote Similarity NPD1032 Phase 2
0.6407 Remote Similarity NPD8466 Approved
0.6407 Remote Similarity NPD8467 Approved
0.6407 Remote Similarity NPD8465 Approved
0.6404 Remote Similarity NPD4529 Approved
0.6404 Remote Similarity NPD4526 Approved
0.6404 Remote Similarity NPD6361 Phase 2
0.6404 Remote Similarity NPD4528 Approved
0.64 Remote Similarity NPD8424 Clinical (unspecified phase)
0.64 Remote Similarity NPD4948 Discontinued
0.64 Remote Similarity NPD8020 Approved
0.64 Remote Similarity NPD8021 Approved
0.6398 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6398 Remote Similarity NPD7191 Phase 2
0.6398 Remote Similarity NPD7467 Discontinued
0.6387 Remote Similarity NPD7470 Discontinued
0.6383 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6383 Remote Similarity NPD7957 Phase 1
0.6383 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6383 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6382 Remote Similarity NPD5640 Discontinued
0.6382 Remote Similarity NPD7426 Phase 1
0.6379 Remote Similarity NPD1996 Discontinued
0.6378 Remote Similarity NPD5883 Phase 2
0.6377 Remote Similarity NPD5450 Discontinued
0.6377 Remote Similarity NPD9074 Approved
0.6377 Remote Similarity NPD9075 Approved
0.6376 Remote Similarity NPD6739 Clinical (unspecified phase)
0.6375 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6375 Remote Similarity NPD5293 Phase 2
0.6364 Remote Similarity NPD7395 Discontinued
0.636 Remote Similarity NPD3921 Approved
0.636 Remote Similarity NPD3923 Approved
0.636 Remote Similarity NPD3924 Approved
0.636 Remote Similarity NPD3922 Approved
0.636 Remote Similarity NPD5866 Approved
0.6356 Remote Similarity NPD7562 Approved
0.6356 Remote Similarity NPD4086 Phase 1
0.6352 Remote Similarity NPD6298 Discontinued
0.635 Remote Similarity NPD6228 Discontinued
0.6344 Remote Similarity NPD6281 Approved
0.6341 Remote Similarity NPD7269 Clinical (unspecified phase)
0.6341 Remote Similarity NPD3925 Approved
0.634 Remote Similarity NPD3946 Clinical (unspecified phase)
0.634 Remote Similarity NPD4894 Discontinued
0.6339 Remote Similarity NPD7417 Discontinued
0.6333 Remote Similarity NPD5888 Phase 2
0.6328 Remote Similarity NPD7967 Discontinued
0.6324 Remote Similarity NPD7660 Clinical (unspecified phase)
0.6323 Remote Similarity NPD3386 Phase 2
0.6322 Remote Similarity NPD8000 Clinical (unspecified phase)
0.632 Remote Similarity NPD7796 Approved
0.632 Remote Similarity NPD7797 Approved
0.632 Remote Similarity NPD5003 Discontinued
0.6318 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6314 Remote Similarity NPD6716 Phase 1
0.6314 Remote Similarity NPD8425 Approved
0.6314 Remote Similarity NPD8459 Approved
0.6314 Remote Similarity NPD8460 Approved
0.6314 Remote Similarity NPD8426 Approved
0.6313 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6311 Remote Similarity NPD8407 Phase 2
0.6311 Remote Similarity NPD7424 Clinical (unspecified phase)
0.6305 Remote Similarity NPD5022 Discontinued
0.6303 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6296 Remote Similarity NPD4429 Discontinued
0.6288 Remote Similarity NPD6665 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