Structure

Physi-Chem Properties

Molecular Weight:  776.25
Volume:  734.949
LogP:  0.517
LogD:  0.558
LogS:  -2.659
# Rotatable Bonds:  17
TPSA:  291.82
# H-Bond Aceptor:  18
# H-Bond Donor:  10
# Rings:  5
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.074
Synthetic Accessibility Score:  4.914
Fsp3:  0.459
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.898
MDCK Permeability:  2.9427626941469498e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.982
Human Intestinal Absorption (HIA):  0.91
20% Bioavailability (F20%):  0.042
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.098
Plasma Protein Binding (PPB):  92.92692565917969%
Volume Distribution (VD):  0.378
Pgp-substrate:  6.0627617835998535%

ADMET: Metabolism

CYP1A2-inhibitor:  0.141
CYP1A2-substrate:  0.011
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.067
CYP2C9-inhibitor:  0.019
CYP2C9-substrate:  0.197
CYP2D6-inhibitor:  0.033
CYP2D6-substrate:  0.177
CYP3A4-inhibitor:  0.037
CYP3A4-substrate:  0.124

ADMET: Excretion

Clearance (CL):  1.136
Half-life (T1/2):  0.612

ADMET: Toxicity

hERG Blockers:  0.605
Human Hepatotoxicity (H-HT):  0.084
Drug-inuced Liver Injury (DILI):  0.654
AMES Toxicity:  0.102
Rat Oral Acute Toxicity:  0.011
Maximum Recommended Daily Dose:  0.001
Skin Sensitization:  0.125
Carcinogencity:  0.644
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.001

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

  Natural Product: NPC160882

Natural Product ID:  NPC160882
Common Name*:   Vandateroside Ii
IUPAC Name:   bis[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl] (2R)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]butanedioate
Synonyms:   Vandateroside II
Standard InCHIKey:  DGKISHSPYWCSLM-VODBULHWSA-N
Standard InCHI:  InChI=1S/C37H44O18/c38-15-25-28(42)30(44)32(46)34(54-25)52-23-9-3-20(4-10-23)17-50-27(41)14-37(49,13-19-1-7-22(40)8-2-19)36(48)51-18-21-5-11-24(12-6-21)53-35-33(47)31(45)29(43)26(16-39)55-35/h1-12,25-26,28-35,38-40,42-47,49H,13-18H2/t25-,26-,28-,29-,30+,31+,32-,33-,34-,35-,37-/m1/s1
SMILES:  c1cc(ccc1C[C@@](CC(=O)OCc1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)(C(=O)OCc1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1801777
PubChem CID:   53355890
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0004165] Phenolic glycosides

*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
NPO30423 Vanda teres Species Orchidaceae Eukaryota n.a. root n.a. PMID[21510636]
NPO30423 Vanda teres Species Orchidaceae Eukaryota n.a. stem n.a. PMID[21510636]
NPO30423 Vanda teres Species Orchidaceae Eukaryota n.a. leaf n.a. PMID[21510636]

☑ 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
NPT2 Others Unspecified FC = 60.0 n.a. PMID[523808]
NPT2 Others Unspecified Activity = 158.0 % PMID[523808]

☑ 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 NPC160882 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
0.8854 High Similarity NPC469654
0.8797 High Similarity NPC44507
0.879 High Similarity NPC40920
0.879 High Similarity NPC223335
0.8704 High Similarity NPC128403
0.8696 High Similarity NPC280923
0.8642 High Similarity NPC475174
0.8634 High Similarity NPC227297
0.8608 High Similarity NPC163635
0.8606 High Similarity NPC470438
0.8598 High Similarity NPC280385
0.8598 High Similarity NPC164704
0.8598 High Similarity NPC470712
0.8571 High Similarity NPC116229
0.8554 High Similarity NPC473630
0.8545 High Similarity NPC474522
0.8545 High Similarity NPC470714
0.8545 High Similarity NPC470715
0.8545 High Similarity NPC470716
0.8544 High Similarity NPC131532
0.8535 High Similarity NPC87403
0.8519 High Similarity NPC475183
0.8509 High Similarity NPC132737
0.8485 Intermediate Similarity NPC138990
0.8485 Intermediate Similarity NPC175429
0.8485 Intermediate Similarity NPC209550
0.8485 Intermediate Similarity NPC277532
0.8471 Intermediate Similarity NPC106818
0.8457 Intermediate Similarity NPC472876
0.8452 Intermediate Similarity NPC220282
0.8431 Intermediate Similarity NPC471028
0.8428 Intermediate Similarity NPC38699
0.8418 Intermediate Similarity NPC245615
0.8418 Intermediate Similarity NPC299706
0.8418 Intermediate Similarity NPC61604
0.8418 Intermediate Similarity NPC115466
0.8415 Intermediate Similarity NPC64425
0.8405 Intermediate Similarity NPC80068
0.8397 Intermediate Similarity NPC22137
0.8393 Intermediate Similarity NPC231787
0.8387 Intermediate Similarity NPC175275
0.8387 Intermediate Similarity NPC97240
0.8385 Intermediate Similarity NPC231475
0.8385 Intermediate Similarity NPC57072
0.8375 Intermediate Similarity NPC478055
0.8373 Intermediate Similarity NPC280642
0.8373 Intermediate Similarity NPC96605
0.8373 Intermediate Similarity NPC218161
0.8373 Intermediate Similarity NPC188815
0.8373 Intermediate Similarity NPC76047
0.8373 Intermediate Similarity NPC469344
0.8363 Intermediate Similarity NPC75574
0.8354 Intermediate Similarity NPC129264
0.8354 Intermediate Similarity NPC85751
0.8354 Intermediate Similarity NPC287889
0.8354 Intermediate Similarity NPC289667
0.8354 Intermediate Similarity NPC99216
0.8354 Intermediate Similarity NPC19240
0.8354 Intermediate Similarity NPC139060
0.8354 Intermediate Similarity NPC205824
0.8354 Intermediate Similarity NPC135358
0.8354 Intermediate Similarity NPC76831
0.8354 Intermediate Similarity NPC292929
0.8353 Intermediate Similarity NPC469371
0.8344 Intermediate Similarity NPC476871
0.8344 Intermediate Similarity NPC471873
0.8344 Intermediate Similarity NPC259576
0.8344 Intermediate Similarity NPC298171
0.8344 Intermediate Similarity NPC158635
0.8344 Intermediate Similarity NPC182350
0.8344 Intermediate Similarity NPC100818
0.8344 Intermediate Similarity NPC229882
0.8344 Intermediate Similarity NPC221091
0.8333 Intermediate Similarity NPC28776
0.8333 Intermediate Similarity NPC136761
0.8333 Intermediate Similarity NPC328093
0.8333 Intermediate Similarity NPC473138
0.8333 Intermediate Similarity NPC472339
0.8323 Intermediate Similarity NPC217822
0.8323 Intermediate Similarity NPC257011
0.8323 Intermediate Similarity NPC288152
0.8323 Intermediate Similarity NPC254071
0.8323 Intermediate Similarity NPC11847
0.8323 Intermediate Similarity NPC149502
0.8323 Intermediate Similarity NPC271755
0.8323 Intermediate Similarity NPC137871
0.8323 Intermediate Similarity NPC101399
0.8323 Intermediate Similarity NPC221288
0.8323 Intermediate Similarity NPC9002
0.8323 Intermediate Similarity NPC222665
0.8322 Intermediate Similarity NPC471029
0.8313 Intermediate Similarity NPC658
0.8313 Intermediate Similarity NPC5319
0.8313 Intermediate Similarity NPC197708
0.8304 Intermediate Similarity NPC156785
0.8304 Intermediate Similarity NPC470718
0.8304 Intermediate Similarity NPC162394
0.8304 Intermediate Similarity NPC241781
0.8303 Intermediate Similarity NPC260504
0.8303 Intermediate Similarity NPC203145
0.8303 Intermediate Similarity NPC32641
0.8303 Intermediate Similarity NPC68592
0.8303 Intermediate Similarity NPC186816
0.8303 Intermediate Similarity NPC12013
0.8303 Intermediate Similarity NPC298666
0.8303 Intermediate Similarity NPC262222
0.8303 Intermediate Similarity NPC477613
0.8303 Intermediate Similarity NPC89809
0.8303 Intermediate Similarity NPC11432
0.8303 Intermediate Similarity NPC189564
0.8303 Intermediate Similarity NPC473278
0.8303 Intermediate Similarity NPC221342
0.8303 Intermediate Similarity NPC476470
0.8303 Intermediate Similarity NPC256188
0.8303 Intermediate Similarity NPC142142
0.8301 Intermediate Similarity NPC469623
0.8301 Intermediate Similarity NPC148080
0.8299 Intermediate Similarity NPC17968
0.8299 Intermediate Similarity NPC469705
0.8299 Intermediate Similarity NPC470122
0.8294 Intermediate Similarity NPC179862
0.8293 Intermediate Similarity NPC121290
0.8291 Intermediate Similarity NPC300329
0.8291 Intermediate Similarity NPC131874
0.8284 Intermediate Similarity NPC170018
0.8284 Intermediate Similarity NPC66820
0.8284 Intermediate Similarity NPC92403
0.8284 Intermediate Similarity NPC76112
0.8282 Intermediate Similarity NPC470125
0.8282 Intermediate Similarity NPC477629
0.8282 Intermediate Similarity NPC101636
0.8282 Intermediate Similarity NPC472994
0.8282 Intermediate Similarity NPC195685
0.8282 Intermediate Similarity NPC210961
0.8282 Intermediate Similarity NPC297987
0.8282 Intermediate Similarity NPC477628
0.8282 Intermediate Similarity NPC64305
0.8282 Intermediate Similarity NPC471869
0.8282 Intermediate Similarity NPC135846
0.8282 Intermediate Similarity NPC170052
0.8282 Intermediate Similarity NPC282169
0.8282 Intermediate Similarity NPC270675
0.8278 Intermediate Similarity NPC469696
0.8274 Intermediate Similarity NPC168789
0.8269 Intermediate Similarity NPC474422
0.8266 Intermediate Similarity NPC282636
0.8266 Intermediate Similarity NPC294863
0.8263 Intermediate Similarity NPC92815
0.8263 Intermediate Similarity NPC210808
0.8263 Intermediate Similarity NPC199079
0.8256 Intermediate Similarity NPC25946
0.8256 Intermediate Similarity NPC470720
0.8256 Intermediate Similarity NPC470717
0.8256 Intermediate Similarity NPC21359
0.8256 Intermediate Similarity NPC470713
0.8256 Intermediate Similarity NPC275977
0.8256 Intermediate Similarity NPC223860
0.8256 Intermediate Similarity NPC249560
0.8256 Intermediate Similarity NPC106700
0.8256 Intermediate Similarity NPC460984
0.8255 Intermediate Similarity NPC164172
0.825 Intermediate Similarity NPC185103
0.825 Intermediate Similarity NPC92153
0.825 Intermediate Similarity NPC299761
0.825 Intermediate Similarity NPC230439
0.825 Intermediate Similarity NPC279281
0.8247 Intermediate Similarity NPC469367
0.8235 Intermediate Similarity NPC113836
0.8235 Intermediate Similarity NPC37668
0.8235 Intermediate Similarity NPC253521
0.8232 Intermediate Similarity NPC326278
0.8232 Intermediate Similarity NPC259834
0.8232 Intermediate Similarity NPC246024
0.8232 Intermediate Similarity NPC27942
0.8232 Intermediate Similarity NPC475382
0.8232 Intermediate Similarity NPC240306
0.8232 Intermediate Similarity NPC244875
0.8228 Intermediate Similarity NPC107197
0.8225 Intermediate Similarity NPC253685
0.8224 Intermediate Similarity NPC324262
0.8224 Intermediate Similarity NPC62800
0.8221 Intermediate Similarity NPC142860
0.8221 Intermediate Similarity NPC97285
0.8221 Intermediate Similarity NPC471079
0.8221 Intermediate Similarity NPC271270
0.8221 Intermediate Similarity NPC246469
0.8221 Intermediate Similarity NPC470405
0.8221 Intermediate Similarity NPC187379
0.8221 Intermediate Similarity NPC153342
0.8221 Intermediate Similarity NPC304741
0.8214 Intermediate Similarity NPC47140
0.8214 Intermediate Similarity NPC5786
0.8214 Intermediate Similarity NPC102851
0.8214 Intermediate Similarity NPC67134
0.821 Intermediate Similarity NPC476026
0.821 Intermediate Similarity NPC474441
0.821 Intermediate Similarity NPC471878
0.821 Intermediate Similarity NPC133984
0.821 Intermediate Similarity NPC474401
0.821 Intermediate Similarity NPC474398

  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 NPC160882 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
0.8839 High Similarity NPD8455 Phase 2
0.8313 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD8312 Approved
0.8284 Intermediate Similarity NPD8313 Approved
0.8118 Intermediate Similarity NPD7808 Phase 3
0.8098 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8059 Intermediate Similarity NPD7251 Discontinued
0.8026 Intermediate Similarity NPD7097 Phase 1
0.8 Intermediate Similarity NPD6797 Phase 2
0.8 Intermediate Similarity NPD6233 Phase 2
0.7955 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7941 Intermediate Similarity NPD7074 Phase 3
0.7941 Intermediate Similarity NPD7472 Approved
0.7933 Intermediate Similarity NPD6798 Discontinued
0.7929 Intermediate Similarity NPD7228 Approved
0.7907 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD7054 Approved
0.7811 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD6166 Phase 2
0.7811 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD3787 Discontinued
0.7771 Intermediate Similarity NPD7075 Discontinued
0.7756 Intermediate Similarity NPD7266 Discontinued
0.7719 Intermediate Similarity NPD3751 Discontinued
0.7711 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD6355 Discontinued
0.7644 Intermediate Similarity NPD6559 Discontinued
0.7644 Intermediate Similarity NPD7240 Approved
0.7616 Intermediate Similarity NPD3818 Discontinued
0.759 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6190 Approved
0.7546 Intermediate Similarity NPD5403 Approved
0.7545 Intermediate Similarity NPD5402 Approved
0.7543 Intermediate Similarity NPD7685 Pre-registration
0.753 Intermediate Similarity NPD37 Approved
0.7516 Intermediate Similarity NPD7033 Discontinued
0.7516 Intermediate Similarity NPD7095 Approved
0.7515 Intermediate Similarity NPD4380 Phase 2
0.7515 Intermediate Similarity NPD6234 Discontinued
0.75 Intermediate Similarity NPD4965 Approved
0.75 Intermediate Similarity NPD4967 Phase 2
0.75 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD4628 Phase 3
0.7469 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD1091 Approved
0.7442 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD7783 Phase 2
0.7433 Intermediate Similarity NPD7435 Discontinued
0.7427 Intermediate Similarity NPD7199 Phase 2
0.7425 Intermediate Similarity NPD6801 Discontinued
0.7423 Intermediate Similarity NPD5401 Approved
0.7423 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD4062 Phase 3
0.7396 Intermediate Similarity NPD7768 Phase 2
0.7365 Intermediate Similarity NPD7411 Suspended
0.7355 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD7698 Approved
0.734 Intermediate Similarity NPD7697 Approved
0.734 Intermediate Similarity NPD7696 Phase 3
0.7333 Intermediate Similarity NPD8434 Phase 2
0.733 Intermediate Similarity NPD8151 Discontinued
0.7302 Intermediate Similarity NPD7871 Phase 2
0.7302 Intermediate Similarity NPD7870 Phase 2
0.7299 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD7874 Approved
0.7292 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD1653 Approved
0.7277 Intermediate Similarity NPD7701 Phase 2
0.7273 Intermediate Similarity NPD6782 Approved
0.7273 Intermediate Similarity NPD6776 Approved
0.7273 Intermediate Similarity NPD6778 Approved
0.7273 Intermediate Similarity NPD6781 Approved
0.7273 Intermediate Similarity NPD6777 Approved
0.7273 Intermediate Similarity NPD6779 Approved
0.7273 Intermediate Similarity NPD6780 Approved
0.7256 Intermediate Similarity NPD6799 Approved
0.7249 Intermediate Similarity NPD7680 Approved
0.7235 Intermediate Similarity NPD3817 Phase 2
0.7226 Intermediate Similarity NPD4908 Phase 1
0.7222 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD1934 Approved
0.7212 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD8320 Phase 1
0.7211 Intermediate Similarity NPD8319 Approved
0.7205 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD5058 Phase 3
0.7176 Intermediate Similarity NPD7819 Suspended
0.7176 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD7699 Phase 2
0.7166 Intermediate Similarity NPD7700 Phase 2
0.716 Intermediate Similarity NPD4534 Discontinued
0.716 Intermediate Similarity NPD1549 Phase 2
0.716 Intermediate Similarity NPD5958 Discontinued
0.716 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1613 Approved
0.7152 Intermediate Similarity NPD4060 Phase 1
0.7151 Intermediate Similarity NPD3749 Approved
0.7143 Intermediate Similarity NPD7458 Discontinued
0.7134 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD3764 Approved
0.7128 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6959 Discontinued
0.7117 Intermediate Similarity NPD6674 Discontinued
0.7108 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD4340 Discontinued
0.7105 Intermediate Similarity NPD1535 Discovery
0.7101 Intermediate Similarity NPD6599 Discontinued
0.7097 Intermediate Similarity NPD5647 Approved
0.7086 Intermediate Similarity NPD6232 Discontinued
0.7079 Intermediate Similarity NPD5844 Phase 1
0.7077 Intermediate Similarity NPD7801 Approved
0.7076 Intermediate Similarity NPD7972 Discontinued
0.7073 Intermediate Similarity NPD3750 Approved
0.7073 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD1894 Discontinued
0.7062 Intermediate Similarity NPD7473 Discontinued
0.7059 Intermediate Similarity NPD1481 Phase 2
0.7049 Intermediate Similarity NPD8150 Discontinued
0.7029 Intermediate Similarity NPD8127 Discontinued
0.7024 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD6823 Phase 2
0.7015 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD7843 Approved
0.7005 Intermediate Similarity NPD6535 Approved
0.7005 Intermediate Similarity NPD6534 Approved
0.6994 Remote Similarity NPD3882 Suspended
0.6977 Remote Similarity NPD2801 Approved
0.6977 Remote Similarity NPD1465 Phase 2
0.6964 Remote Similarity NPD1512 Approved
0.6962 Remote Similarity NPD3027 Phase 3
0.6957 Remote Similarity NPD6653 Approved
0.6951 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6948 Remote Similarity NPD1608 Approved
0.6943 Remote Similarity NPD2861 Phase 2
0.6941 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6941 Remote Similarity NPD3226 Approved
0.6933 Remote Similarity NPD2935 Discontinued
0.6933 Remote Similarity NPD1551 Phase 2
0.6923 Remote Similarity NPD2797 Approved
0.6918 Remote Similarity NPD2313 Discontinued
0.6914 Remote Similarity NPD4536 Approved
0.6914 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6914 Remote Similarity NPD4538 Approved
0.6899 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6832 Phase 2
0.6894 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6894 Remote Similarity NPD1933 Approved
0.6894 Remote Similarity NPD5124 Phase 1
0.6892 Remote Similarity NPD5535 Approved
0.689 Remote Similarity NPD5763 Approved
0.689 Remote Similarity NPD6005 Phase 3
0.689 Remote Similarity NPD6003 Clinical (unspecified phase)
0.689 Remote Similarity NPD6002 Phase 3
0.689 Remote Similarity NPD6006 Clinical (unspecified phase)
0.689 Remote Similarity NPD5762 Approved
0.689 Remote Similarity NPD6004 Phase 3
0.6886 Remote Similarity NPD7440 Discontinued
0.6883 Remote Similarity NPD1610 Phase 2
0.6872 Remote Similarity NPD7584 Approved
0.6871 Remote Similarity NPD5960 Phase 3
0.6871 Remote Similarity NPD5588 Approved
0.6871 Remote Similarity NPD2799 Discontinued
0.6871 Remote Similarity NPD1510 Phase 2
0.6867 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6867 Remote Similarity NPD7157 Approved
0.6863 Remote Similarity NPD5846 Approved
0.6863 Remote Similarity NPD6516 Phase 2
0.686 Remote Similarity NPD6677 Suspended
0.6859 Remote Similarity NPD3225 Approved
0.6848 Remote Similarity NPD2424 Discontinued
0.6845 Remote Similarity NPD1511 Approved
0.6837 Remote Similarity NPD7585 Approved
0.6835 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6829 Remote Similarity NPD2796 Approved
0.6829 Remote Similarity NPD6032 Approved
0.6815 Remote Similarity NPD1203 Approved
0.6813 Remote Similarity NPD3268 Approved
0.6807 Remote Similarity NPD1652 Phase 2
0.6805 Remote Similarity NPD3536 Discontinued
0.6798 Remote Similarity NPD7229 Phase 3
0.6788 Remote Similarity NPD6800 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7583 Approved
0.678 Remote Similarity NPD5494 Approved
0.6768 Remote Similarity NPD3748 Approved
0.6766 Remote Similarity NPD4110 Phase 3
0.6766 Remote Similarity NPD8166 Discontinued
0.6766 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6273 Approved
0.6757 Remote Similarity NPD7090 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