Structure

Physi-Chem Properties

Molecular Weight:  618.39
Volume:  666.047
LogP:  7.292
LogD:  5.667
LogS:  -4.343
# Rotatable Bonds:  6
TPSA:  104.06
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.132
Synthetic Accessibility Score:  4.943
Fsp3:  0.692
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.426
MDCK Permeability:  2.1984487830195576e-05
Pgp-inhibitor:  0.022
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.166
30% Bioavailability (F30%):  0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.046
Plasma Protein Binding (PPB):  100.09862518310547%
Volume Distribution (VD):  0.432
Pgp-substrate:  3.3258893489837646%

ADMET: Metabolism

CYP1A2-inhibitor:  0.044
CYP1A2-substrate:  0.506
CYP2C19-inhibitor:  0.116
CYP2C19-substrate:  0.598
CYP2C9-inhibitor:  0.123
CYP2C9-substrate:  0.963
CYP2D6-inhibitor:  0.253
CYP2D6-substrate:  0.65
CYP3A4-inhibitor:  0.169
CYP3A4-substrate:  0.259

ADMET: Excretion

Clearance (CL):  1.47
Half-life (T1/2):  0.301

ADMET: Toxicity

hERG Blockers:  0.14
Human Hepatotoxicity (H-HT):  0.413
Drug-inuced Liver Injury (DILI):  0.006
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.065
Maximum Recommended Daily Dose:  0.953
Skin Sensitization:  0.933
Carcinogencity:  0.01
Eye Corrosion:  0.023
Eye Irritation:  0.463
Respiratory Toxicity:  0.878

Download Data

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

  Natural Product: NPC66894

Natural Product ID:  NPC66894
Common Name*:   Betulinic Acid 3Beta-Caffeate
IUPAC Name:   (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms:   Betulinic Acid 3Beta-Caffeate; Betulinic Acid 3Beta-Transcaffeate
Standard InCHIKey:  MNUNUJQYFJZRHQ-VZLLCJDWSA-N
Standard InCHI:  InChI=1S/C39H54O6/c1-23(2)25-14-19-39(34(43)44)21-20-37(6)26(33(25)39)10-12-30-36(5)17-16-31(35(3,4)29(36)15-18-38(30,37)7)45-32(42)13-9-24-8-11-27(40)28(41)22-24/h8-9,11,13,22,25-26,29-31,33,40-41H,1,10,12,14-21H2,2-7H3,(H,43,44)/b13-9+/t25-,26+,29-,30+,31-,33+,36-,37+,38+,39-/m0/s1
SMILES:  O=C(O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)C)C(=O)O)C)C)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1077309
PubChem CID:   6439576
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO13813 Durio carinatus Species Malvaceae Eukaryota n.a. stem n.a. DOI[10.1021/np100332v]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[14600382]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota Twigs n.a. n.a. PMID[25894905]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota Twigs n.a. n.a. PMID[28358502]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13813 Durio carinatus Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26327 Chaenomeles sinensis Species Rosaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 = 4370.0 nM PMID[487864]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 7040.0 nM PMID[487864]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 9720.0 nM PMID[487864]
NPT148 Cell Line HCT-15 Homo sapiens IC50 = 5830.0 nM PMID[487864]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 = 6900.0 nM PMID[487865]
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 = 81700.0 nM PMID[487866]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 10000.0 nM PMID[487867]
NPT81 Cell Line A549 Homo sapiens IC50 = 9900.0 nM PMID[487867]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 > 10000.0 nM PMID[487867]
NPT148 Cell Line HCT-15 Homo sapiens IC50 > 10000.0 nM PMID[487867]
NPT76 Cell Line C6 Rattus norvegicus Activity = 355.7 % PMID[487867]
NPT76 Cell Line C6 Rattus norvegicus Activity = 95.0 % PMID[487867]
NPT2 Others Unspecified IC50 = 850.0 nM PMID[487865]

☑ 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 NPC66894 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 NPC8102
0.964 High Similarity NPC477873
0.964 High Similarity NPC469447
0.9638 High Similarity NPC473612
0.9568 High Similarity NPC35212
0.9517 High Similarity NPC105942
0.9517 High Similarity NPC205392
0.9504 High Similarity NPC53520
0.95 High Similarity NPC252133
0.95 High Similarity NPC310621
0.9493 High Similarity NPC248287
0.9493 High Similarity NPC234548
0.9225 High Similarity NPC235557
0.922 High Similarity NPC304110
0.922 High Similarity NPC27518
0.9214 High Similarity NPC182249
0.9161 High Similarity NPC26045
0.9149 High Similarity NPC271494
0.9149 High Similarity NPC473591
0.9149 High Similarity NPC155192
0.9143 High Similarity NPC471152
0.9137 High Similarity NPC477874
0.9137 High Similarity NPC173569
0.9116 High Similarity NPC118033
0.9071 High Similarity NPC249817
0.9065 High Similarity NPC11266
0.9054 High Similarity NPC475579
0.9054 High Similarity NPC473773
0.9028 High Similarity NPC25491
0.9007 High Similarity NPC22676
0.9007 High Similarity NPC475482
0.9007 High Similarity NPC216940
0.9007 High Similarity NPC198621
0.9 High Similarity NPC43353
0.8986 High Similarity NPC473680
0.8986 High Similarity NPC475311
0.8986 High Similarity NPC473579
0.8986 High Similarity NPC475454
0.8966 High Similarity NPC19862
0.8966 High Similarity NPC235195
0.8944 High Similarity NPC139243
0.8944 High Similarity NPC116742
0.8912 High Similarity NPC32017
0.8912 High Similarity NPC96930
0.8881 High Similarity NPC470616
0.8881 High Similarity NPC470617
0.8851 High Similarity NPC292206
0.8851 High Similarity NPC273358
0.8851 High Similarity NPC298647
0.8851 High Similarity NPC279442
0.8846 High Similarity NPC200726
0.8841 High Similarity NPC30174
0.8836 High Similarity NPC280717
0.8836 High Similarity NPC271607
0.8836 High Similarity NPC307205
0.8819 High Similarity NPC172311
0.8803 High Similarity NPC476699
0.8792 High Similarity NPC470618
0.8792 High Similarity NPC470619
0.8792 High Similarity NPC208785
0.8792 High Similarity NPC145527
0.879 High Similarity NPC177362
0.8734 High Similarity NPC202428
0.8734 High Similarity NPC266545
0.8723 High Similarity NPC475457
0.8723 High Similarity NPC475627
0.8723 High Similarity NPC18982
0.8723 High Similarity NPC475346
0.8705 High Similarity NPC86257
0.869 High Similarity NPC472801
0.8621 High Similarity NPC471875
0.86 High Similarity NPC477206
0.8592 High Similarity NPC476282
0.8591 High Similarity NPC472936
0.8591 High Similarity NPC472937
0.8591 High Similarity NPC472938
0.8571 High Similarity NPC475138
0.8562 High Similarity NPC470035
0.8551 High Similarity NPC137416
0.8543 High Similarity NPC327962
0.8531 High Similarity NPC471913
0.8514 High Similarity NPC477207
0.8471 Intermediate Similarity NPC266365
0.8451 Intermediate Similarity NPC243305
0.8425 Intermediate Similarity NPC132723
0.8425 Intermediate Similarity NPC76032
0.8421 Intermediate Similarity NPC472939
0.8421 Intermediate Similarity NPC142654
0.8411 Intermediate Similarity NPC477483
0.8411 Intermediate Similarity NPC325032
0.8387 Intermediate Similarity NPC472807
0.8345 Intermediate Similarity NPC265413
0.8345 Intermediate Similarity NPC10154
0.8345 Intermediate Similarity NPC472804
0.8345 Intermediate Similarity NPC103082
0.8344 Intermediate Similarity NPC477208
0.8322 Intermediate Similarity NPC184935
0.831 Intermediate Similarity NPC288290
0.8278 Intermediate Similarity NPC470038
0.8278 Intermediate Similarity NPC75295
0.8276 Intermediate Similarity NPC194970
0.8258 Intermediate Similarity NPC266084
0.8258 Intermediate Similarity NPC475145
0.8258 Intermediate Similarity NPC475595
0.8258 Intermediate Similarity NPC475216
0.8258 Intermediate Similarity NPC475162
0.8258 Intermediate Similarity NPC473544
0.8258 Intermediate Similarity NPC83663
0.8235 Intermediate Similarity NPC264229
0.8235 Intermediate Similarity NPC46549
0.8227 Intermediate Similarity NPC190849
0.8227 Intermediate Similarity NPC171007
0.8221 Intermediate Similarity NPC472803
0.8214 Intermediate Similarity NPC15127
0.82 Intermediate Similarity NPC477209
0.8188 Intermediate Similarity NPC29599
0.8176 Intermediate Similarity NPC469680
0.8176 Intermediate Similarity NPC471974
0.8176 Intermediate Similarity NPC469681
0.8171 Intermediate Similarity NPC469776
0.8171 Intermediate Similarity NPC469775
0.8171 Intermediate Similarity NPC469778
0.8171 Intermediate Similarity NPC469777
0.8171 Intermediate Similarity NPC469774
0.8171 Intermediate Similarity NPC32723
0.8171 Intermediate Similarity NPC469772
0.8171 Intermediate Similarity NPC295941
0.8171 Intermediate Similarity NPC100925
0.8171 Intermediate Similarity NPC469773
0.8171 Intermediate Similarity NPC135334
0.8158 Intermediate Similarity NPC258856
0.8146 Intermediate Similarity NPC96447
0.8129 Intermediate Similarity NPC470037
0.8129 Intermediate Similarity NPC77310
0.8117 Intermediate Similarity NPC473719
0.8113 Intermediate Similarity NPC471750
0.8108 Intermediate Similarity NPC49911
0.8108 Intermediate Similarity NPC477592
0.8105 Intermediate Similarity NPC246229
0.8105 Intermediate Similarity NPC273798
0.8105 Intermediate Similarity NPC191899
0.8105 Intermediate Similarity NPC474991
0.8098 Intermediate Similarity NPC286809
0.8095 Intermediate Similarity NPC279463
0.8095 Intermediate Similarity NPC252343
0.8085 Intermediate Similarity NPC288945
0.8082 Intermediate Similarity NPC203486
0.8067 Intermediate Similarity NPC38473
0.8058 Intermediate Similarity NPC470848
0.8058 Intermediate Similarity NPC470849
0.8056 Intermediate Similarity NPC131684
0.8054 Intermediate Similarity NPC477593
0.8049 Intermediate Similarity NPC471870
0.8041 Intermediate Similarity NPC154485
0.8041 Intermediate Similarity NPC90431
0.8041 Intermediate Similarity NPC471872
0.8039 Intermediate Similarity NPC320734
0.8039 Intermediate Similarity NPC84786
0.8027 Intermediate Similarity NPC477594
0.8026 Intermediate Similarity NPC471876
0.8025 Intermediate Similarity NPC471874
0.8025 Intermediate Similarity NPC161151
0.8013 Intermediate Similarity NPC472410
0.8013 Intermediate Similarity NPC178048
0.8013 Intermediate Similarity NPC261659
0.8013 Intermediate Similarity NPC477595
0.8 Intermediate Similarity NPC132810
0.8 Intermediate Similarity NPC253591
0.8 Intermediate Similarity NPC110699
0.8 Intermediate Similarity NPC106055
0.7987 Intermediate Similarity NPC277559
0.7975 Intermediate Similarity NPC62051
0.7974 Intermediate Similarity NPC126707
0.7973 Intermediate Similarity NPC477596
0.7972 Intermediate Similarity NPC471930
0.7972 Intermediate Similarity NPC473220
0.7972 Intermediate Similarity NPC471929
0.7972 Intermediate Similarity NPC470753
0.7972 Intermediate Similarity NPC471935
0.7971 Intermediate Similarity NPC309434
0.7971 Intermediate Similarity NPC203124
0.7963 Intermediate Similarity NPC471873
0.7962 Intermediate Similarity NPC124842
0.7962 Intermediate Similarity NPC270268
0.7961 Intermediate Similarity NPC469855
0.7961 Intermediate Similarity NPC30846
0.7961 Intermediate Similarity NPC471972
0.7961 Intermediate Similarity NPC471971
0.7959 Intermediate Similarity NPC475468
0.7959 Intermediate Similarity NPC126516
0.7959 Intermediate Similarity NPC155209
0.7959 Intermediate Similarity NPC168799
0.7959 Intermediate Similarity NPC48929
0.7959 Intermediate Similarity NPC329913
0.7958 Intermediate Similarity NPC471927
0.7958 Intermediate Similarity NPC474532
0.7949 Intermediate Similarity NPC261322
0.7947 Intermediate Similarity NPC9218
0.7945 Intermediate Similarity NPC318799
0.7945 Intermediate Similarity NPC198388

  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 NPC66894 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
0.9429 High Similarity NPD8166 Discontinued
0.8354 Intermediate Similarity NPD8127 Discontinued
0.8322 Intermediate Similarity NPD6663 Approved
0.8298 Intermediate Similarity NPD5736 Approved
0.7987 Intermediate Similarity NPD6273 Approved
0.7857 Intermediate Similarity NPD3019 Approved
0.7778 Intermediate Similarity NPD7003 Approved
0.773 Intermediate Similarity NPD2932 Approved
0.7722 Intermediate Similarity NPD7458 Discontinued
0.7703 Intermediate Similarity NPD8032 Phase 2
0.7662 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD4110 Phase 3
0.7651 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD3620 Phase 2
0.7616 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD7028 Phase 2
0.7533 Intermediate Similarity NPD4140 Approved
0.75 Intermediate Similarity NPD6190 Approved
0.75 Intermediate Similarity NPD3092 Approved
0.7486 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6355 Discontinued
0.7468 Intermediate Similarity NPD7266 Discontinued
0.7465 Intermediate Similarity NPD3091 Approved
0.7456 Intermediate Similarity NPD7228 Approved
0.7455 Intermediate Similarity NPD6234 Discontinued
0.7452 Intermediate Similarity NPD7236 Approved
0.7431 Intermediate Similarity NPD3026 Approved
0.7431 Intermediate Similarity NPD3023 Approved
0.7415 Intermediate Similarity NPD3094 Phase 2
0.7413 Intermediate Similarity NPD3024 Approved
0.7413 Intermediate Similarity NPD3025 Approved
0.7358 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD4628 Phase 3
0.7285 Intermediate Similarity NPD3764 Approved
0.7283 Intermediate Similarity NPD7685 Pre-registration
0.7278 Intermediate Similarity NPD7910 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD8438 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD37 Approved
0.7255 Intermediate Similarity NPD5735 Approved
0.725 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD5763 Approved
0.7244 Intermediate Similarity NPD5762 Approved
0.7241 Intermediate Similarity NPD3095 Discontinued
0.7229 Intermediate Similarity NPD4966 Approved
0.7229 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD4965 Approved
0.7229 Intermediate Similarity NPD4967 Phase 2
0.7222 Intermediate Similarity NPD7239 Suspended
0.7219 Intermediate Similarity NPD7095 Approved
0.7219 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD3022 Approved
0.7194 Intermediate Similarity NPD3021 Approved
0.719 Intermediate Similarity NPD4060 Phase 1
0.7188 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD5408 Approved
0.7179 Intermediate Similarity NPD5406 Approved
0.7179 Intermediate Similarity NPD5404 Approved
0.7179 Intermediate Similarity NPD5405 Approved
0.7178 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD3455 Phase 2
0.7171 Intermediate Similarity NPD6798 Discontinued
0.7162 Intermediate Similarity NPD5327 Phase 3
0.7162 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD7097 Phase 1
0.716 Intermediate Similarity NPD7199 Phase 2
0.7143 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD230 Phase 1
0.7124 Intermediate Similarity NPD7961 Discontinued
0.7123 Intermediate Similarity NPD4059 Approved
0.7114 Intermediate Similarity NPD1283 Approved
0.711 Intermediate Similarity NPD5844 Phase 1
0.7105 Intermediate Similarity NPD7008 Discontinued
0.7102 Intermediate Similarity NPD8313 Approved
0.7102 Intermediate Similarity NPD8312 Approved
0.7097 Intermediate Similarity NPD6353 Approved
0.7078 Intermediate Similarity NPD826 Approved
0.7078 Intermediate Similarity NPD825 Approved
0.7076 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD2935 Discontinued
0.7063 Intermediate Similarity NPD2629 Approved
0.7042 Intermediate Similarity NPD7094 Approved
0.7042 Intermediate Similarity NPD6858 Approved
0.7029 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD7768 Phase 2
0.702 Intermediate Similarity NPD4624 Approved
0.7007 Intermediate Similarity NPD4626 Approved
0.7006 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7473 Discontinued
0.6989 Remote Similarity NPD7240 Approved
0.6987 Remote Similarity NPD6653 Approved
0.6983 Remote Similarity NPD8150 Discontinued
0.6982 Remote Similarity NPD7833 Phase 2
0.6982 Remote Similarity NPD7831 Phase 2
0.6982 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6968 Remote Similarity NPD2979 Phase 3
0.6962 Remote Similarity NPD2438 Suspended
0.6954 Remote Similarity NPD2797 Approved
0.6939 Remote Similarity NPD5691 Approved
0.6937 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3657 Discovery
0.6919 Remote Similarity NPD6232 Discontinued
0.6915 Remote Similarity NPD7497 Discontinued
0.6913 Remote Similarity NPD1281 Approved
0.6905 Remote Similarity NPD7819 Suspended
0.6905 Remote Similarity NPD8455 Phase 2
0.6903 Remote Similarity NPD6233 Phase 2
0.6899 Remote Similarity NPD2799 Discontinued
0.6897 Remote Similarity NPD4198 Discontinued
0.6887 Remote Similarity NPD1876 Approved
0.6886 Remote Similarity NPD6677 Suspended
0.6871 Remote Similarity NPD9545 Approved
0.6871 Remote Similarity NPD7741 Discontinued
0.6863 Remote Similarity NPD9494 Approved
0.6845 Remote Similarity NPD1934 Approved
0.6842 Remote Similarity NPD1470 Approved
0.6839 Remote Similarity NPD3268 Approved
0.6839 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6839 Remote Similarity NPD6166 Phase 2
0.6839 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6831 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6828 Remote Similarity NPD5951 Approved
0.6824 Remote Similarity NPD7058 Phase 2
0.6824 Remote Similarity NPD7057 Phase 3
0.6816 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6815 Remote Similarity NPD555 Phase 2
0.6813 Remote Similarity NPD2346 Discontinued
0.6803 Remote Similarity NPD7610 Discontinued
0.68 Remote Similarity NPD1201 Approved
0.6797 Remote Similarity NPD5647 Approved
0.6797 Remote Similarity NPD258 Approved
0.6797 Remote Similarity NPD257 Approved
0.6796 Remote Similarity NPD8434 Phase 2
0.6792 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6792 Remote Similarity NPD7743 Approved
0.6792 Remote Similarity NPD7742 Approved
0.679 Remote Similarity NPD3750 Approved
0.6786 Remote Similarity NPD6873 Phase 2
0.6784 Remote Similarity NPD7075 Discontinued
0.678 Remote Similarity NPD7074 Phase 3
0.6778 Remote Similarity NPD7090 Clinical (unspecified phase)
0.677 Remote Similarity NPD5958 Discontinued
0.677 Remote Similarity NPD4534 Discontinued
0.6768 Remote Similarity NPD7390 Discontinued
0.6765 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6761 Remote Similarity NPD7799 Discontinued
0.6753 Remote Similarity NPD2861 Phase 2
0.6752 Remote Similarity NPD943 Approved
0.675 Remote Similarity NPD2531 Phase 2
0.675 Remote Similarity NPD6099 Approved
0.675 Remote Similarity NPD6100 Approved
0.6748 Remote Similarity NPD8131 Suspended
0.6743 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6737 Remote Similarity NPD7680 Approved
0.6733 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6728 Remote Similarity NPD6674 Discontinued
0.6727 Remote Similarity NPD3645 Discontinued
0.6725 Remote Similarity NPD3882 Suspended
0.6723 Remote Similarity NPD7054 Approved
0.6711 Remote Similarity NPD1651 Approved
0.6711 Remote Similarity NPD5585 Approved
0.6708 Remote Similarity NPD6002 Phase 3
0.6708 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6708 Remote Similarity NPD6004 Phase 3
0.6708 Remote Similarity NPD6005 Phase 3
0.6708 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6706 Remote Similarity NPD5761 Phase 2
0.6706 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6706 Remote Similarity NPD1465 Phase 2
0.6706 Remote Similarity NPD5760 Phase 2
0.6702 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6689 Remote Similarity NPD5536 Phase 2
0.6688 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6688 Remote Similarity NPD4062 Phase 3
0.6688 Remote Similarity NPD259 Phase 1
0.6686 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6685 Remote Similarity NPD2490 Approved
0.6685 Remote Similarity NPD2488 Approved
0.6685 Remote Similarity NPD7472 Approved
0.6667 Remote Similarity NPD1778 Approved
0.6667 Remote Similarity NPD3226 Approved
0.6667 Remote Similarity NPD3818 Discontinued
0.6667 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3027 Phase 3
0.6667 Remote Similarity NPD6959 Discontinued
0.6667 Remote Similarity NPD970 Clinical (unspecified phase)
0.6647 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4476 Approved
0.6646 Remote Similarity NPD4477 Approved
0.6645 Remote Similarity NPD9269 Phase 2
0.6645 Remote Similarity NPD1608 Approved
0.6645 Remote Similarity NPD3972 Approved
0.6644 Remote Similarity NPD5283 Phase 1
0.6644 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6643 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6629 Remote Similarity NPD7315 Approved
0.6627 Remote Similarity NPD2532 Approved
0.6627 Remote Similarity NPD2534 Approved
0.6627 Remote Similarity NPD2533 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