Structure

Physi-Chem Properties

Molecular Weight:  718.15
Volume:  684.253
LogP:  1.888
LogD:  1.586
LogS:  -5.303
# Rotatable Bonds:  13
TPSA:  292.2
# H-Bond Aceptor:  16
# H-Bond Donor:  11
# Rings:  5
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.05
Synthetic Accessibility Score:  4.444
Fsp3:  0.139
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.955
MDCK Permeability:  3.2707653190300334e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  1.0
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.01
Plasma Protein Binding (PPB):  95.06751251220703%
Volume Distribution (VD):  0.227
Pgp-substrate:  6.819146156311035%

ADMET: Metabolism

CYP1A2-inhibitor:  0.227
CYP1A2-substrate:  0.01
CYP2C19-inhibitor:  0.048
CYP2C19-substrate:  0.021
CYP2C9-inhibitor:  0.499
CYP2C9-substrate:  0.096
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.112
CYP3A4-inhibitor:  0.013
CYP3A4-substrate:  0.002

ADMET: Excretion

Clearance (CL):  7.78
Half-life (T1/2):  0.952

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.35
Drug-inuced Liver Injury (DILI):  0.988
AMES Toxicity:  0.133
Rat Oral Acute Toxicity:  0.037
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.955
Carcinogencity:  0.103
Eye Corrosion:  0.003
Eye Irritation:  0.902
Respiratory Toxicity:  0.009

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

  Natural Product: NPC471750

Natural Product ID:  NPC471750
Common Name*:   Salvianolic Acid L
IUPAC Name:   (2R)-2-[3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-1,2-dihydronaphthalene-1-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid
Synonyms:  
Standard InCHIKey:  CLZDRNKNWXDFQT-UNTSIKIQSA-N
Standard InCHI:  InChI=1S/C36H30O16/c37-20-5-1-15(9-24(20)41)11-27(33(45)46)51-35(49)19-13-17-4-8-23(40)32(44)30(17)31(29(19)18-3-7-22(39)26(43)14-18)36(50)52-28(34(47)48)12-16-2-6-21(38)25(42)10-16/h1-10,13-14,27-29,31,37-44H,11-12H2,(H,45,46)(H,47,48)/t27-,28-,29?,31?/m1/s1
SMILES:  OC(=O)[C@H](OC(=O)C1=Cc2ccc(c(c2C(C1c1ccc(c(c1)O)O)C(=O)O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)O)O)Cc1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3113339
PubChem CID:   76324956
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0002044] Phenylnaphthalenes

*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
NPO22667 Plectranthus amboinicus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[24491635]
NPO22667 Plectranthus amboinicus 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
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens IC50 = 1600.0 nM PMID[568997]

☑ 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 NPC471750 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
0.9536 High Similarity NPC475145
0.9536 High Similarity NPC475216
0.9536 High Similarity NPC473544
0.9536 High Similarity NPC475595
0.9536 High Similarity NPC83663
0.9536 High Similarity NPC475162
0.9536 High Similarity NPC266084
0.8896 High Similarity NPC186100
0.8896 High Similarity NPC41494
0.8896 High Similarity NPC216403
0.8867 High Similarity NPC38473
0.8782 High Similarity NPC477334
0.8636 High Similarity NPC477333
0.8636 High Similarity NPC228940
0.8608 High Similarity NPC270268
0.8606 High Similarity NPC217781
0.8598 High Similarity NPC162169
0.8598 High Similarity NPC166851
0.8589 High Similarity NPC144557
0.8571 High Similarity NPC473630
0.8545 High Similarity NPC317671
0.8545 High Similarity NPC175793
0.8545 High Similarity NPC49983
0.8545 High Similarity NPC142707
0.8545 High Similarity NPC26536
0.8537 High Similarity NPC134047
0.8537 High Similarity NPC223006
0.8537 High Similarity NPC272750
0.8537 High Similarity NPC173729
0.8516 High Similarity NPC53520
0.8512 High Similarity NPC471871
0.8509 High Similarity NPC134925
0.8503 High Similarity NPC470272
0.8494 Intermediate Similarity NPC43918
0.8494 Intermediate Similarity NPC470271
0.8494 Intermediate Similarity NPC261411
0.8494 Intermediate Similarity NPC311389
0.8494 Intermediate Similarity NPC190204
0.8481 Intermediate Similarity NPC327962
0.8471 Intermediate Similarity NPC155910
0.8471 Intermediate Similarity NPC17042
0.8424 Intermediate Similarity NPC45943
0.8418 Intermediate Similarity NPC473719
0.8415 Intermediate Similarity NPC266365
0.8402 Intermediate Similarity NPC98583
0.8393 Intermediate Similarity NPC47521
0.8387 Intermediate Similarity NPC469447
0.8387 Intermediate Similarity NPC319628
0.8387 Intermediate Similarity NPC220664
0.8387 Intermediate Similarity NPC37331
0.8387 Intermediate Similarity NPC477873
0.8387 Intermediate Similarity NPC284948
0.8387 Intermediate Similarity NPC303090
0.8385 Intermediate Similarity NPC125487
0.8385 Intermediate Similarity NPC281703
0.8383 Intermediate Similarity NPC31034
0.8344 Intermediate Similarity NPC296044
0.8344 Intermediate Similarity NPC167098
0.8343 Intermediate Similarity NPC65333
0.8343 Intermediate Similarity NPC100251
0.8333 Intermediate Similarity NPC202428
0.8333 Intermediate Similarity NPC471870
0.8333 Intermediate Similarity NPC25581
0.8333 Intermediate Similarity NPC266545
0.8333 Intermediate Similarity NPC18074
0.8333 Intermediate Similarity NPC5419
0.8333 Intermediate Similarity NPC61
0.8323 Intermediate Similarity NPC224389
0.8323 Intermediate Similarity NPC35702
0.8323 Intermediate Similarity NPC297517
0.8323 Intermediate Similarity NPC206095
0.8323 Intermediate Similarity NPC13818
0.8323 Intermediate Similarity NPC477335
0.8323 Intermediate Similarity NPC471027
0.8314 Intermediate Similarity NPC198902
0.8313 Intermediate Similarity NPC252979
0.8303 Intermediate Similarity NPC216916
0.8295 Intermediate Similarity NPC201814
0.8291 Intermediate Similarity NPC229264
0.8291 Intermediate Similarity NPC191899
0.8291 Intermediate Similarity NPC246229
0.8291 Intermediate Similarity NPC474991
0.8282 Intermediate Similarity NPC473275
0.8282 Intermediate Similarity NPC470896
0.8278 Intermediate Similarity NPC168799
0.8278 Intermediate Similarity NPC155209
0.8278 Intermediate Similarity NPC471749
0.8274 Intermediate Similarity NPC177362
0.8269 Intermediate Similarity NPC43158
0.8269 Intermediate Similarity NPC277315
0.8269 Intermediate Similarity NPC472016
0.8269 Intermediate Similarity NPC192831
0.8269 Intermediate Similarity NPC258469
0.8267 Intermediate Similarity NPC198388
0.8258 Intermediate Similarity NPC477279
0.8253 Intermediate Similarity NPC291957
0.8253 Intermediate Similarity NPC149389
0.8253 Intermediate Similarity NPC322982
0.8253 Intermediate Similarity NPC14030
0.8239 Intermediate Similarity NPC7839
0.8239 Intermediate Similarity NPC192568
0.8239 Intermediate Similarity NPC471076
0.8239 Intermediate Similarity NPC142291
0.8239 Intermediate Similarity NPC127046
0.8239 Intermediate Similarity NPC173872
0.8239 Intermediate Similarity NPC119094
0.8229 Intermediate Similarity NPC112380
0.8228 Intermediate Similarity NPC258856
0.8228 Intermediate Similarity NPC75295
0.8228 Intermediate Similarity NPC84786
0.8221 Intermediate Similarity NPC472835
0.8221 Intermediate Similarity NPC203757
0.8217 Intermediate Similarity NPC25491
0.8217 Intermediate Similarity NPC470130
0.8214 Intermediate Similarity NPC200726
0.8205 Intermediate Similarity NPC91546
0.8205 Intermediate Similarity NPC477278
0.8205 Intermediate Similarity NPC477277
0.8204 Intermediate Similarity NPC470898
0.8198 Intermediate Similarity NPC472723
0.8194 Intermediate Similarity NPC156709
0.8194 Intermediate Similarity NPC179505
0.8193 Intermediate Similarity NPC139540
0.8193 Intermediate Similarity NPC177100
0.8182 Intermediate Similarity NPC269625
0.8176 Intermediate Similarity NPC180768
0.8176 Intermediate Similarity NPC322660
0.8176 Intermediate Similarity NPC472803
0.8171 Intermediate Similarity NPC471968
0.8171 Intermediate Similarity NPC239019
0.8171 Intermediate Similarity NPC247629
0.8165 Intermediate Similarity NPC126707
0.8161 Intermediate Similarity NPC8940
0.816 Intermediate Similarity NPC469888
0.815 Intermediate Similarity NPC47191
0.8148 Intermediate Similarity NPC267091
0.8141 Intermediate Similarity NPC27518
0.8141 Intermediate Similarity NPC290664
0.8141 Intermediate Similarity NPC304110
0.8141 Intermediate Similarity NPC172311
0.814 Intermediate Similarity NPC171706
0.8137 Intermediate Similarity NPC280753
0.8137 Intermediate Similarity NPC44378
0.8136 Intermediate Similarity NPC205721
0.8129 Intermediate Similarity NPC142703
0.8129 Intermediate Similarity NPC283560
0.8129 Intermediate Similarity NPC476370
0.8129 Intermediate Similarity NPC302857
0.8129 Intermediate Similarity NPC219428
0.8129 Intermediate Similarity NPC152942
0.8129 Intermediate Similarity NPC24295
0.8129 Intermediate Similarity NPC37250
0.8129 Intermediate Similarity NPC278068
0.8125 Intermediate Similarity NPC119767
0.8125 Intermediate Similarity NPC142528
0.8125 Intermediate Similarity NPC472135
0.8121 Intermediate Similarity NPC156818
0.8121 Intermediate Similarity NPC289322
0.8121 Intermediate Similarity NPC160512
0.8121 Intermediate Similarity NPC68324
0.8121 Intermediate Similarity NPC38779
0.8121 Intermediate Similarity NPC238419
0.8121 Intermediate Similarity NPC172419
0.8121 Intermediate Similarity NPC114179
0.8113 Intermediate Similarity NPC66894
0.8113 Intermediate Similarity NPC8102
0.8103 Intermediate Similarity NPC80956
0.8101 Intermediate Similarity NPC160378
0.8098 Intermediate Similarity NPC471874
0.8098 Intermediate Similarity NPC474534
0.8098 Intermediate Similarity NPC474533
0.8086 Intermediate Similarity NPC118033
0.8086 Intermediate Similarity NPC243891
0.8086 Intermediate Similarity NPC475718
0.8084 Intermediate Similarity NPC469889
0.8081 Intermediate Similarity NPC476374
0.8077 Intermediate Similarity NPC476820
0.8077 Intermediate Similarity NPC471875
0.8077 Intermediate Similarity NPC205751
0.8077 Intermediate Similarity NPC26241
0.8077 Intermediate Similarity NPC274891
0.8077 Intermediate Similarity NPC303683
0.8077 Intermediate Similarity NPC295492
0.8077 Intermediate Similarity NPC476819
0.8077 Intermediate Similarity NPC474875
0.8077 Intermediate Similarity NPC191280
0.8075 Intermediate Similarity NPC42464
0.8075 Intermediate Similarity NPC94781
0.8072 Intermediate Similarity NPC210501
0.8072 Intermediate Similarity NPC318826
0.8072 Intermediate Similarity NPC104222
0.8072 Intermediate Similarity NPC114791
0.8072 Intermediate Similarity NPC141331
0.8068 Intermediate Similarity NPC231254
0.8066 Intermediate Similarity NPC3474
0.8065 Intermediate Similarity NPC471152
0.8065 Intermediate Similarity NPC67349
0.8065 Intermediate Similarity NPC279676
0.8063 Intermediate Similarity NPC147250
0.8061 Intermediate Similarity NPC300845

  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 NPC471750 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
0.8387 Intermediate Similarity NPD6190 Approved
0.8235 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8205 Intermediate Similarity NPD8166 Discontinued
0.8171 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD8150 Discontinued
0.7784 Intermediate Similarity NPD8313 Approved
0.7784 Intermediate Similarity NPD8312 Approved
0.7719 Intermediate Similarity NPD6232 Discontinued
0.7701 Intermediate Similarity NPD5844 Phase 1
0.7688 Intermediate Similarity NPD7473 Discontinued
0.768 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6234 Discontinued
0.763 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD6166 Phase 2
0.7543 Intermediate Similarity NPD7228 Approved
0.7515 Intermediate Similarity NPD8455 Phase 2
0.7515 Intermediate Similarity NPD1465 Phase 2
0.75 Intermediate Similarity NPD3764 Approved
0.75 Intermediate Similarity NPD5404 Approved
0.75 Intermediate Similarity NPD5408 Approved
0.75 Intermediate Similarity NPD5406 Approved
0.75 Intermediate Similarity NPD5405 Approved
0.7471 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD8127 Discontinued
0.7456 Intermediate Similarity NPD37 Approved
0.7453 Intermediate Similarity NPD7266 Discontinued
0.743 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD4965 Approved
0.7427 Intermediate Similarity NPD4966 Approved
0.7427 Intermediate Similarity NPD4967 Phase 2
0.7416 Intermediate Similarity NPD6797 Phase 2
0.7394 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD7075 Discontinued
0.7374 Intermediate Similarity NPD7251 Discontinued
0.7368 Intermediate Similarity NPD3817 Phase 2
0.7363 Intermediate Similarity NPD8434 Phase 2
0.7362 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD230 Phase 1
0.7356 Intermediate Similarity NPD6959 Discontinued
0.7345 Intermediate Similarity NPD3751 Discontinued
0.7333 Intermediate Similarity NPD7808 Phase 3
0.733 Intermediate Similarity NPD8320 Phase 1
0.733 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD8319 Approved
0.7326 Intermediate Similarity NPD3882 Suspended
0.7317 Intermediate Similarity NPD7003 Approved
0.7317 Intermediate Similarity NPD4628 Phase 3
0.731 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD4060 Phase 1
0.7289 Intermediate Similarity NPD7390 Discontinued
0.7278 Intermediate Similarity NPD3226 Approved
0.7278 Intermediate Similarity NPD7685 Pre-registration
0.7278 Intermediate Similarity NPD7458 Discontinued
0.7278 Intermediate Similarity NPD6798 Discontinued
0.7257 Intermediate Similarity NPD7199 Phase 2
0.7251 Intermediate Similarity NPD1934 Approved
0.7247 Intermediate Similarity NPD3818 Discontinued
0.7246 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD4380 Phase 2
0.7216 Intermediate Similarity NPD3787 Discontinued
0.7209 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD7819 Suspended
0.7188 Intermediate Similarity NPD7435 Discontinued
0.7182 Intermediate Similarity NPD7240 Approved
0.7176 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD5402 Approved
0.7168 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7074 Phase 3
0.7167 Intermediate Similarity NPD7472 Approved
0.7151 Intermediate Similarity NPD6801 Discontinued
0.7143 Intermediate Similarity NPD6355 Discontinued
0.7128 Intermediate Similarity NPD6535 Approved
0.7128 Intermediate Similarity NPD6534 Approved
0.7126 Intermediate Similarity NPD7768 Phase 2
0.7117 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD7054 Approved
0.7111 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD2801 Approved
0.7108 Intermediate Similarity NPD3750 Approved
0.7105 Intermediate Similarity NPD7700 Phase 2
0.7105 Intermediate Similarity NPD7699 Phase 2
0.7101 Intermediate Similarity NPD6273 Approved
0.7101 Intermediate Similarity NPD1512 Approved
0.7093 Intermediate Similarity NPD7411 Suspended
0.7092 Intermediate Similarity NPD8151 Discontinued
0.7081 Intermediate Similarity NPD943 Approved
0.707 Intermediate Similarity NPD1470 Approved
0.7056 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7874 Approved
0.7056 Intermediate Similarity NPD7177 Discontinued
0.7041 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6599 Discontinued
0.7031 Intermediate Similarity NPD6780 Approved
0.7031 Intermediate Similarity NPD6776 Approved
0.7031 Intermediate Similarity NPD6777 Approved
0.7031 Intermediate Similarity NPD6782 Approved
0.7031 Intermediate Similarity NPD6778 Approved
0.7031 Intermediate Similarity NPD6779 Approved
0.7031 Intermediate Similarity NPD6781 Approved
0.7024 Intermediate Similarity NPD3300 Phase 2
0.7019 Intermediate Similarity NPD6663 Approved
0.7019 Intermediate Similarity NPD6233 Phase 2
0.7012 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5494 Approved
0.6989 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6989 Remote Similarity NPD3749 Approved
0.6982 Remote Similarity NPD1511 Approved
0.6982 Remote Similarity NPD6799 Approved
0.6981 Remote Similarity NPD5736 Approved
0.6974 Remote Similarity NPD7871 Phase 2
0.6974 Remote Similarity NPD7870 Phase 2
0.6959 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5403 Approved
0.6941 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6941 Remote Similarity NPD2532 Approved
0.6941 Remote Similarity NPD2533 Approved
0.6941 Remote Similarity NPD2534 Approved
0.6928 Remote Similarity NPD5762 Approved
0.6928 Remote Similarity NPD5763 Approved
0.6923 Remote Similarity NPD7698 Approved
0.6923 Remote Similarity NPD7680 Approved
0.6923 Remote Similarity NPD7696 Phase 3
0.6923 Remote Similarity NPD7236 Approved
0.6923 Remote Similarity NPD1201 Approved
0.6923 Remote Similarity NPD7697 Approved
0.6919 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6909 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6886 Remote Similarity NPD970 Clinical (unspecified phase)
0.6883 Remote Similarity NPD9545 Approved
0.6879 Remote Similarity NPD9269 Phase 2
0.6879 Remote Similarity NPD3455 Phase 2
0.6875 Remote Similarity NPD8485 Approved
0.6869 Remote Similarity NPD7701 Phase 2
0.6867 Remote Similarity NPD2935 Discontinued
0.6867 Remote Similarity NPD2438 Suspended
0.685 Remote Similarity NPD7801 Approved
0.6848 Remote Similarity NPD7097 Phase 1
0.6842 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5401 Approved
0.6833 Remote Similarity NPD7229 Phase 3
0.6826 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6826 Remote Similarity NPD2346 Discontinued
0.6823 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6821 Remote Similarity NPD7239 Suspended
0.6811 Remote Similarity NPD8368 Discontinued
0.6811 Remote Similarity NPD6559 Discontinued
0.6809 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6807 Remote Similarity NPD3748 Approved
0.6806 Remote Similarity NPD6212 Phase 3
0.6806 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6806 Remote Similarity NPD6213 Phase 3
0.6805 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6804 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6796 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6792 Remote Similarity NPD1283 Approved
0.679 Remote Similarity NPD7095 Approved
0.6789 Remote Similarity NPD2490 Approved
0.6789 Remote Similarity NPD2488 Approved
0.6776 Remote Similarity NPD7799 Discontinued
0.6772 Remote Similarity NPD1608 Approved
0.677 Remote Similarity NPD9494 Approved
0.6769 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6768 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6768 Remote Similarity NPD1613 Approved
0.6768 Remote Similarity NPD2979 Phase 3
0.6766 Remote Similarity NPD7783 Phase 2
0.6766 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6751 Remote Similarity NPD4004 Approved
0.6751 Remote Similarity NPD4002 Approved
0.6744 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6737 Remote Similarity NPD8360 Approved
0.6737 Remote Similarity NPD8361 Approved
0.6737 Remote Similarity NPD8435 Approved
0.6735 Remote Similarity NPD3450 Approved
0.6735 Remote Similarity NPD3452 Approved
0.6735 Remote Similarity NPD2494 Approved
0.6735 Remote Similarity NPD2493 Approved
0.673 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6724 Remote Similarity NPD1653 Approved
0.6717 Remote Similarity NPD4582 Approved
0.6717 Remote Similarity NPD4583 Approved
0.6707 Remote Similarity NPD2799 Discontinued
0.6707 Remote Similarity NPD1510 Phase 2
0.6706 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6706 Remote Similarity NPD4110 Phase 3
0.6705 Remote Similarity NPD6385 Approved
0.6705 Remote Similarity NPD6386 Approved
0.6702 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6702 Remote Similarity NPD8407 Phase 2
0.6701 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6688 Remote Similarity NPD3019 Approved
0.6688 Remote Similarity NPD2932 Approved
0.6687 Remote Similarity NPD3027 Phase 3
0.6687 Remote Similarity NPD7008 Discontinued
0.6687 Remote Similarity NPD5952 Clinical (unspecified phase)

  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