Structure

Physi-Chem Properties

Molecular Weight:  718.15
Volume:  684.253
LogP:  2.468
LogD:  2.184
LogS:  -4.248
# Rotatable Bonds:  14
TPSA:  278.04
# H-Bond Aceptor:  16
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.058
Synthetic Accessibility Score:  4.541
Fsp3:  0.167
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.821
MDCK Permeability:  4.894971880275989e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.932
20% Bioavailability (F20%):  0.981
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.012
Plasma Protein Binding (PPB):  96.0674819946289%
Volume Distribution (VD):  0.339
Pgp-substrate:  4.864240646362305%

ADMET: Metabolism

CYP1A2-inhibitor:  0.034
CYP1A2-substrate:  0.017
CYP2C19-inhibitor:  0.059
CYP2C19-substrate:  0.027
CYP2C9-inhibitor:  0.642
CYP2C9-substrate:  0.965
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.151
CYP3A4-inhibitor:  0.059
CYP3A4-substrate:  0.039

ADMET: Excretion

Clearance (CL):  8.801
Half-life (T1/2):  0.962

ADMET: Toxicity

hERG Blockers:  0.024
Human Hepatotoxicity (H-HT):  0.482
Drug-inuced Liver Injury (DILI):  0.951
AMES Toxicity:  0.027
Rat Oral Acute Toxicity:  0.578
Maximum Recommended Daily Dose:  0.026
Skin Sensitization:  0.953
Carcinogencity:  0.246
Eye Corrosion:  0.003
Eye Irritation:  0.848
Respiratory Toxicity:  0.008

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

  Natural Product: NPC186100

Natural Product ID:  NPC186100
Common Name*:   Salvianolic Acid B
IUPAC Name:   (2R)-2-[(E)-3-[(2R,3R)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid
Synonyms:  
Standard InCHIKey:  SNKFFCBZYFGCQN-PDVBOLEISA-N
Standard InCHI:  InChI=1S/C36H30O16/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48)/b10-5+/t27-,28-,31-,32+/m1/s1
SMILES:  O=C(O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc(c2c1[C@@H](C(=O)O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)[C@@H](O2)c1ccc(c(c1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3747259
PubChem CID:   11629084
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. root n.a. PMID[11374966]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[16038550]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota exudates n.a. n.a. PMID[16441065]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17583950]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota stems n.a. n.a. PMID[18558745]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18855446]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20455578]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21775156]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21824777]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23286284]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[24108414]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[25590529]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota stems n.a. n.a. PMID[25891102]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[27569393]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[29185738]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[30351923]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. root n.a. PMID[3655791]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota roots n.a. n.a. PMID[9834151]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19148 Gouania tomentosa Species Gobiesocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21396 Spongia vermicularis Species Spongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21056 Angelica keiskei Species Apiaceae 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
NPT365 Individual Protein NAD(P)H dehydrogenase [quinone] 1 Mus musculus FC = 1.4 n.a. PMID[459761]
NPT365 Individual Protein NAD(P)H dehydrogenase [quinone] 1 Mus musculus FC = 1.0 n.a. PMID[459761]
NPT27 Others Unspecified Activity = 79.0 % PMID[459761]
NPT27 Others Unspecified Activity = 85.0 % PMID[459761]
NPT35 Others n.a. Inhibition = 37.6 % PMID[459761]
NPT35 Others n.a. Inhibition = 60.2 % PMID[459761]
NPT35 Others n.a. Inhibition = 64.1 % PMID[459761]
NPT35 Others n.a. Inhibition = 84.7 % PMID[459761]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 4.81 % PMID[459762]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 90.07 % PMID[459763]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 IC50 = 3420.0 nM PMID[459763]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.1 % PMID[459764]

☑ 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 NPC186100 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 NPC41494
1.0 High Similarity NPC216403
0.9684 High Similarity NPC144557
0.9623 High Similarity NPC134047
0.9623 High Similarity NPC272750
0.9623 High Similarity NPC173729
0.9623 High Similarity NPC223006
0.9141 High Similarity NPC45943
0.9018 High Similarity NPC216916
0.8929 High Similarity NPC476370
0.8896 High Similarity NPC471750
0.8876 High Similarity NPC476374
0.8869 High Similarity NPC91043
0.8869 High Similarity NPC180768
0.8868 High Similarity NPC221091
0.8868 High Similarity NPC259576
0.8857 High Similarity NPC201814
0.8851 High Similarity NPC269625
0.8812 High Similarity NPC300329
0.8788 High Similarity NPC469889
0.8765 High Similarity NPC469888
0.8758 High Similarity NPC267091
0.875 High Similarity NPC167231
0.875 High Similarity NPC215802
0.8728 High Similarity NPC170203
0.8727 High Similarity NPC472962
0.8727 High Similarity NPC472961
0.8713 High Similarity NPC473630
0.8704 High Similarity NPC115203
0.8696 High Similarity NPC243891
0.8686 High Similarity NPC112380
0.8659 High Similarity NPC470896
0.8659 High Similarity NPC473275
0.8655 High Similarity NPC98583
0.8655 High Similarity NPC316539
0.8647 High Similarity NPC476365
0.8636 High Similarity NPC475360
0.8629 High Similarity NPC231254
0.8623 High Similarity NPC476371
0.8623 High Similarity NPC476372
0.8621 High Similarity NPC475996
0.8621 High Similarity NPC47883
0.8614 High Similarity NPC53889
0.8614 High Similarity NPC301089
0.8611 High Similarity NPC3474
0.8608 High Similarity NPC160378
0.8606 High Similarity NPC114179
0.8606 High Similarity NPC68324
0.8606 High Similarity NPC160512
0.8606 High Similarity NPC289322
0.8606 High Similarity NPC156818
0.8606 High Similarity NPC38779
0.8598 High Similarity NPC80489
0.8596 High Similarity NPC100251
0.8596 High Similarity NPC65333
0.8589 High Similarity NPC475595
0.8589 High Similarity NPC475216
0.8589 High Similarity NPC83663
0.8589 High Similarity NPC475145
0.8589 High Similarity NPC266084
0.8589 High Similarity NPC475162
0.8589 High Similarity NPC473544
0.8588 High Similarity NPC7839
0.8588 High Similarity NPC205721
0.8588 High Similarity NPC119094
0.8588 High Similarity NPC142291
0.8588 High Similarity NPC173872
0.858 High Similarity NPC469650
0.858 High Similarity NPC477517
0.858 High Similarity NPC226725
0.858 High Similarity NPC111490
0.858 High Similarity NPC261623
0.8571 High Similarity NPC135831
0.8571 High Similarity NPC297503
0.8571 High Similarity NPC97119
0.8563 High Similarity NPC80956
0.8555 High Similarity NPC154741
0.8555 High Similarity NPC296018
0.8554 High Similarity NPC87317
0.8545 High Similarity NPC88803
0.8545 High Similarity NPC104983
0.8545 High Similarity NPC300845
0.8545 High Similarity NPC291948
0.8545 High Similarity NPC250436
0.8538 High Similarity NPC102277
0.8538 High Similarity NPC279209
0.8531 High Similarity NPC469649
0.8531 High Similarity NPC65489
0.8531 High Similarity NPC260521
0.8529 High Similarity NPC473818
0.8528 High Similarity NPC270268
0.8528 High Similarity NPC476434
0.8523 High Similarity NPC154527
0.8514 High Similarity NPC8940
0.8508 High Similarity NPC189312
0.8506 High Similarity NPC476773
0.8506 High Similarity NPC475783
0.8503 High Similarity NPC476373
0.8503 High Similarity NPC24164
0.8494 Intermediate Similarity NPC125495
0.8488 Intermediate Similarity NPC472454
0.8488 Intermediate Similarity NPC247964
0.8488 Intermediate Similarity NPC186847
0.8488 Intermediate Similarity NPC257667
0.8488 Intermediate Similarity NPC174700
0.8483 Intermediate Similarity NPC158214
0.8483 Intermediate Similarity NPC240200
0.8483 Intermediate Similarity NPC223534
0.8483 Intermediate Similarity NPC477083
0.8483 Intermediate Similarity NPC477081
0.8483 Intermediate Similarity NPC290289
0.848 Intermediate Similarity NPC280493
0.848 Intermediate Similarity NPC107627
0.848 Intermediate Similarity NPC476279
0.8476 Intermediate Similarity NPC295646
0.8476 Intermediate Similarity NPC44730
0.8475 Intermediate Similarity NPC104910
0.8475 Intermediate Similarity NPC474093
0.8466 Intermediate Similarity NPC150977
0.8462 Intermediate Similarity NPC100425
0.8457 Intermediate Similarity NPC244903
0.8452 Intermediate Similarity NPC112418
0.8452 Intermediate Similarity NPC231758
0.8448 Intermediate Similarity NPC473713
0.8448 Intermediate Similarity NPC472723
0.8448 Intermediate Similarity NPC156955
0.8447 Intermediate Similarity NPC221383
0.8447 Intermediate Similarity NPC143892
0.8447 Intermediate Similarity NPC283081
0.8447 Intermediate Similarity NPC299090
0.8436 Intermediate Similarity NPC472721
0.8436 Intermediate Similarity NPC472720
0.8436 Intermediate Similarity NPC187632
0.8436 Intermediate Similarity NPC469652
0.8436 Intermediate Similarity NPC472724
0.8436 Intermediate Similarity NPC160543
0.8436 Intermediate Similarity NPC93065
0.8436 Intermediate Similarity NPC31208
0.8434 Intermediate Similarity NPC318432
0.843 Intermediate Similarity NPC472803
0.8427 Intermediate Similarity NPC475179
0.8427 Intermediate Similarity NPC248315
0.8421 Intermediate Similarity NPC469521
0.8421 Intermediate Similarity NPC298847
0.8421 Intermediate Similarity NPC150131
0.8421 Intermediate Similarity NPC128403
0.8418 Intermediate Similarity NPC38473
0.8412 Intermediate Similarity NPC477840
0.8409 Intermediate Similarity NPC117668
0.8409 Intermediate Similarity NPC125352
0.8402 Intermediate Similarity NPC477841
0.8402 Intermediate Similarity NPC144843
0.8402 Intermediate Similarity NPC174311
0.8402 Intermediate Similarity NPC22324
0.8402 Intermediate Similarity NPC219927
0.8402 Intermediate Similarity NPC471745
0.8402 Intermediate Similarity NPC164937
0.8402 Intermediate Similarity NPC473445
0.84 Intermediate Similarity NPC113836
0.84 Intermediate Similarity NPC297807
0.84 Intermediate Similarity NPC477880
0.84 Intermediate Similarity NPC98546
0.84 Intermediate Similarity NPC37668
0.84 Intermediate Similarity NPC253521
0.84 Intermediate Similarity NPC477882
0.8398 Intermediate Similarity NPC476358
0.8395 Intermediate Similarity NPC472969
0.8393 Intermediate Similarity NPC471744
0.8393 Intermediate Similarity NPC24627
0.8393 Intermediate Similarity NPC44507
0.8391 Intermediate Similarity NPC287243
0.8391 Intermediate Similarity NPC193377
0.8389 Intermediate Similarity NPC97924
0.8389 Intermediate Similarity NPC40078
0.8389 Intermediate Similarity NPC264302
0.8389 Intermediate Similarity NPC471091
0.8383 Intermediate Similarity NPC143328
0.8382 Intermediate Similarity NPC47386
0.8375 Intermediate Similarity NPC470130
0.8373 Intermediate Similarity NPC180901
0.8373 Intermediate Similarity NPC300757
0.8372 Intermediate Similarity NPC266545
0.8372 Intermediate Similarity NPC202428
0.8365 Intermediate Similarity NPC67467
0.8364 Intermediate Similarity NPC474656
0.8364 Intermediate Similarity NPC131121
0.8363 Intermediate Similarity NPC472452
0.8363 Intermediate Similarity NPC471823
0.8363 Intermediate Similarity NPC224851
0.8363 Intermediate Similarity NPC171985
0.8363 Intermediate Similarity NPC43065
0.8363 Intermediate Similarity NPC320741
0.8362 Intermediate Similarity NPC470718
0.8362 Intermediate Similarity NPC129533
0.8362 Intermediate Similarity NPC123259
0.8354 Intermediate Similarity NPC477334
0.8353 Intermediate Similarity NPC291977
0.8353 Intermediate Similarity NPC227297
0.8353 Intermediate Similarity NPC89131
0.8352 Intermediate Similarity NPC93685

  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 NPC186100 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
0.8596 High Similarity NPD7993 Clinical (unspecified phase)
0.8545 High Similarity NPD4868 Clinical (unspecified phase)
0.8352 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD3882 Suspended
0.8304 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8304 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8304 Intermediate Similarity NPD6166 Phase 2
0.8246 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8212 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8208 Intermediate Similarity NPD3818 Discontinued
0.8182 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD3817 Phase 2
0.8136 Intermediate Similarity NPD8313 Approved
0.8136 Intermediate Similarity NPD8312 Approved
0.8095 Intermediate Similarity NPD1465 Phase 2
0.8086 Intermediate Similarity NPD6190 Approved
0.8081 Intermediate Similarity NPD6232 Discontinued
0.8057 Intermediate Similarity NPD5844 Phase 1
0.8046 Intermediate Similarity NPD7473 Discontinued
0.8036 Intermediate Similarity NPD1934 Approved
0.8023 Intermediate Similarity NPD7199 Phase 2
0.8012 Intermediate Similarity NPD6234 Discontinued
0.7978 Intermediate Similarity NPD7808 Phase 3
0.7966 Intermediate Similarity NPD6797 Phase 2
0.7953 Intermediate Similarity NPD7075 Discontinued
0.7921 Intermediate Similarity NPD7251 Discontinued
0.7882 Intermediate Similarity NPD2801 Approved
0.7882 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD5494 Approved
0.7849 Intermediate Similarity NPD3749 Approved
0.7836 Intermediate Similarity NPD5402 Approved
0.7826 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD37 Approved
0.7816 Intermediate Similarity NPD8127 Discontinued
0.7809 Intermediate Similarity NPD7074 Phase 3
0.7809 Intermediate Similarity NPD7472 Approved
0.7802 Intermediate Similarity NPD8434 Phase 2
0.7797 Intermediate Similarity NPD3751 Discontinued
0.7797 Intermediate Similarity NPD7228 Approved
0.7791 Intermediate Similarity NPD4966 Approved
0.7791 Intermediate Similarity NPD4965 Approved
0.7791 Intermediate Similarity NPD4967 Phase 2
0.7784 Intermediate Similarity NPD1512 Approved
0.7778 Intermediate Similarity NPD7819 Suspended
0.7778 Intermediate Similarity NPD8455 Phase 2
0.7778 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD3787 Discontinued
0.7753 Intermediate Similarity NPD7054 Approved
0.7725 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD7685 Pre-registration
0.7719 Intermediate Similarity NPD6801 Discontinued
0.7714 Intermediate Similarity NPD6959 Discontinued
0.7688 Intermediate Similarity NPD7768 Phase 2
0.7684 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD6798 Discontinued
0.7665 Intermediate Similarity NPD6799 Approved
0.7665 Intermediate Similarity NPD1511 Approved
0.7644 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD6355 Discontinued
0.7633 Intermediate Similarity NPD5403 Approved
0.763 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD6599 Discontinued
0.7602 Intermediate Similarity NPD4380 Phase 2
0.759 Intermediate Similarity NPD4628 Phase 3
0.7578 Intermediate Similarity NPD4060 Phase 1
0.7558 Intermediate Similarity NPD7411 Suspended
0.7556 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD3226 Approved
0.753 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD3926 Phase 2
0.7516 Intermediate Similarity NPD6233 Phase 2
0.7515 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD5401 Approved
0.7514 Intermediate Similarity NPD8150 Discontinued
0.75 Intermediate Similarity NPD919 Approved
0.7485 Intermediate Similarity NPD3750 Approved
0.7453 Intermediate Similarity NPD3764 Approved
0.7442 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD7240 Approved
0.7432 Intermediate Similarity NPD6559 Discontinued
0.7412 Intermediate Similarity NPD2532 Approved
0.7412 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD2534 Approved
0.7412 Intermediate Similarity NPD2533 Approved
0.7381 Intermediate Similarity NPD8166 Discontinued
0.7374 Intermediate Similarity NPD7229 Phase 3
0.7368 Intermediate Similarity NPD6273 Approved
0.7365 Intermediate Similarity NPD1549 Phase 2
0.7365 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7435 Discontinued
0.7318 Intermediate Similarity NPD1247 Approved
0.7317 Intermediate Similarity NPD447 Suspended
0.731 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD7033 Discontinued
0.7283 Intermediate Similarity NPD1653 Approved
0.7256 Intermediate Similarity NPD1613 Approved
0.7256 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD5404 Approved
0.7246 Intermediate Similarity NPD2935 Discontinued
0.7246 Intermediate Similarity NPD5406 Approved
0.7246 Intermediate Similarity NPD5408 Approved
0.7246 Intermediate Similarity NPD5405 Approved
0.7245 Intermediate Similarity NPD4002 Approved
0.7245 Intermediate Similarity NPD4004 Approved
0.7236 Intermediate Similarity NPD8151 Discontinued
0.7231 Intermediate Similarity NPD2494 Approved
0.7231 Intermediate Similarity NPD3452 Approved
0.7231 Intermediate Similarity NPD3450 Approved
0.7231 Intermediate Similarity NPD2493 Approved
0.7213 Intermediate Similarity NPD7177 Discontinued
0.7212 Intermediate Similarity NPD230 Phase 1
0.7211 Intermediate Similarity NPD2488 Approved
0.7211 Intermediate Similarity NPD2490 Approved
0.7208 Intermediate Similarity NPD4582 Approved
0.7208 Intermediate Similarity NPD4583 Approved
0.7202 Intermediate Similarity NPD2344 Approved
0.7202 Intermediate Similarity NPD5763 Approved
0.7202 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD5762 Approved
0.7202 Intermediate Similarity NPD7266 Discontinued
0.7202 Intermediate Similarity NPD2346 Discontinued
0.72 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7874 Approved
0.7186 Intermediate Similarity NPD2799 Discontinued
0.7186 Intermediate Similarity NPD1510 Phase 2
0.7186 Intermediate Similarity NPD3748 Approved
0.7179 Intermediate Similarity NPD6777 Approved
0.7179 Intermediate Similarity NPD6782 Approved
0.7179 Intermediate Similarity NPD6776 Approved
0.7179 Intermediate Similarity NPD6778 Approved
0.7179 Intermediate Similarity NPD6781 Approved
0.7179 Intermediate Similarity NPD6779 Approved
0.7179 Intermediate Similarity NPD6780 Approved
0.7178 Intermediate Similarity NPD7095 Approved
0.7176 Intermediate Similarity NPD4110 Phase 3
0.7176 Intermediate Similarity NPD7003 Approved
0.7176 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD1608 Approved
0.7157 Intermediate Similarity NPD7680 Approved
0.715 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2796 Approved
0.7143 Intermediate Similarity NPD7458 Discontinued
0.7134 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD8320 Phase 1
0.7121 Intermediate Similarity NPD7871 Phase 2
0.7121 Intermediate Similarity NPD8319 Approved
0.7121 Intermediate Similarity NPD7870 Phase 2
0.7117 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD7783 Phase 2
0.7079 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD3027 Phase 3
0.7071 Intermediate Similarity NPD7697 Approved
0.7071 Intermediate Similarity NPD7698 Approved
0.7071 Intermediate Similarity NPD7696 Phase 3
0.7059 Intermediate Similarity NPD5958 Discontinued
0.7055 Intermediate Similarity NPD2861 Phase 2
0.7055 Intermediate Similarity NPD9494 Approved
0.7055 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD943 Approved
0.7041 Intermediate Similarity NPD1551 Phase 2
0.7041 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD2797 Approved
0.7035 Intermediate Similarity NPD2309 Approved
0.703 Intermediate Similarity NPD3268 Approved
0.703 Intermediate Similarity NPD2313 Discontinued
0.7026 Intermediate Similarity NPD2974 Approved
0.7026 Intermediate Similarity NPD2975 Approved
0.7026 Intermediate Similarity NPD2973 Approved
0.7024 Intermediate Similarity NPD7097 Phase 1
0.7019 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD7907 Approved
0.7018 Intermediate Similarity NPD6674 Discontinued
0.7015 Intermediate Similarity NPD7701 Phase 2
0.7012 Intermediate Similarity NPD4908 Phase 1
0.7006 Intermediate Similarity NPD1933 Approved
0.7005 Intermediate Similarity NPD4580 Approved
0.7 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.6995 Remote Similarity NPD7801 Approved
0.6988 Remote Similarity NPD4062 Phase 3
0.6981 Remote Similarity NPD17 Approved
0.6979 Remote Similarity NPD4287 Approved
0.6977 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6968 Remote Similarity NPD7038 Approved
0.6968 Remote Similarity NPD7039 Approved
0.6966 Remote Similarity NPD6386 Approved
0.6966 Remote Similarity NPD6385 Approved
0.6954 Remote Similarity NPD7390 Discontinued
0.6946 Remote Similarity NPD1240 Approved
0.6941 Remote Similarity NPD2438 Suspended
0.6938 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6933 Remote Similarity NPD1203 Approved
0.6932 Remote Similarity NPD920 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