Structure

Physi-Chem Properties

Molecular Weight:  800.34
Volume:  795.399
LogP:  0.349
LogD:  0.693
LogS:  -4.016
# Rotatable Bonds:  5
TPSA:  235.22
# H-Bond Aceptor:  17
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.214
Synthetic Accessibility Score:  6.697
Fsp3:  0.39
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.533
MDCK Permeability:  5.345076260709902e-06
Pgp-inhibitor:  0.006
Pgp-substrate:  0.983
Human Intestinal Absorption (HIA):  0.524
20% Bioavailability (F20%):  0.028
30% Bioavailability (F30%):  0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.023
Plasma Protein Binding (PPB):  64.11138153076172%
Volume Distribution (VD):  0.306
Pgp-substrate:  29.050498962402344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.029
CYP2C19-inhibitor:  0.052
CYP2C19-substrate:  0.042
CYP2C9-inhibitor:  0.257
CYP2C9-substrate:  0.753
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.209
CYP3A4-inhibitor:  0.341
CYP3A4-substrate:  0.031

ADMET: Excretion

Clearance (CL):  5.805
Half-life (T1/2):  0.862

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.95
Drug-inuced Liver Injury (DILI):  0.953
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.87
Maximum Recommended Daily Dose:  0.961
Skin Sensitization:  0.103
Carcinogencity:  0.055
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.125

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

  Natural Product: NPC234069

Natural Product ID:  NPC234069
Common Name*:   Rubiyunnanin D
IUPAC Name:   n.a.
Synonyms:   Rubiyunnanin D
Standard InCHIKey:  ATLDLNZCKIPECG-XMPIZRASSA-N
Standard InCHI:  InChI=1S/C41H48N6O11/c1-22-36(52)44-29(15-17-35(50)51)40(56)45(3)30(18-24-6-11-27(48)12-7-24)38(54)43-23(2)39(55)47(5)32-19-25-8-13-28(14-9-25)58-34-21-26(10-16-33(34)49)20-31(37(53)42-22)46(4)41(32)57/h6-14,16,21-23,29-32,48-49H,15,17-20H2,1-5H3,(H,42,53)(H,43,54)(H,44,52)(H,50,51)/t22-,23+,29+,30+,31+,32+/m1/s1
SMILES:  C[C@@H]1C(=N[C@@H](CCC(=O)O)C(=O)N(C)[C@@H](Cc2ccc(cc2)O)C(=N[C@@H](C)C(=O)N(C)[C@H]2Cc3ccc(cc3)Oc3cc(ccc3O)C[C@@H](C(=N1)O)N(C)C2=O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1288983
PubChem CID:   52944620
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000348] Peptides
            • [CHEMONTID:0004831] Oligopeptides

*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
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[12350148]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[12762798]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[21044847]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota roots n.a. n.a. PMID[21973054]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. root n.a. PMID[21973054]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16607 Rubia yunnanensis Species Rubiaceae 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
NPT65 Cell Line HepG2 Homo sapiens IC50 = 15780.0 nM PMID[490788]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 45990.0 nM PMID[490788]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 21280.0 nM PMID[490788]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 15950.0 nM PMID[490788]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 15830.0 nM PMID[490788]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 10230.0 nM PMID[490788]
NPT81 Cell Line A549 Homo sapiens IC50 = 37170.0 nM PMID[490788]
NPT547 Cell Line BGC-823 Homo sapiens IC50 = 30340.0 nM PMID[490788]
NPT165 Cell Line HeLa Homo sapiens IC50 = 15090.0 nM PMID[490788]
NPT380 Cell Line U-251 Homo sapiens IC50 = 26250.0 nM PMID[490788]
NPT319 Cell Line B16 Mus musculus IC50 = 15280.0 nM PMID[490788]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 7220.0 nM PMID[490788]
NPT2 Others Unspecified IC50 = 35070.0 nM PMID[490788]

☑ 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 NPC234069 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
0.994 High Similarity NPC174122
0.994 High Similarity NPC64140
0.9471 High Similarity NPC138083
0.9464 High Similarity NPC32064
0.9226 High Similarity NPC164608
0.9191 High Similarity NPC276120
0.9034 High Similarity NPC29531
0.8729 High Similarity NPC471563
0.8689 High Similarity NPC50548
0.8634 High Similarity NPC144314
0.8595 High Similarity NPC242728
0.8579 High Similarity NPC149962
0.8441 Intermediate Similarity NPC123859
0.8361 Intermediate Similarity NPC473378
0.8361 Intermediate Similarity NPC473407
0.8168 Intermediate Similarity NPC473460
0.8146 Intermediate Similarity NPC159767
0.8146 Intermediate Similarity NPC155506
0.8081 Intermediate Similarity NPC56635
0.8045 Intermediate Similarity NPC473354
0.8033 Intermediate Similarity NPC294951
0.8031 Intermediate Similarity NPC473422
0.799 Intermediate Similarity NPC471531
0.7989 Intermediate Similarity NPC315542
0.7978 Intermediate Similarity NPC471526
0.7966 Intermediate Similarity NPC107938
0.7966 Intermediate Similarity NPC294516
0.7959 Intermediate Similarity NPC471561
0.7944 Intermediate Similarity NPC473402
0.7944 Intermediate Similarity NPC26108
0.7944 Intermediate Similarity NPC476227
0.7933 Intermediate Similarity NPC230611
0.7912 Intermediate Similarity NPC45037
0.7895 Intermediate Similarity NPC233702
0.7889 Intermediate Similarity NPC273755
0.7889 Intermediate Similarity NPC306804
0.7889 Intermediate Similarity NPC137627
0.7845 Intermediate Similarity NPC279871
0.7826 Intermediate Similarity NPC476321
0.7821 Intermediate Similarity NPC186617
0.7819 Intermediate Similarity NPC473305
0.7819 Intermediate Similarity NPC163961
0.7802 Intermediate Similarity NPC50016
0.7789 Intermediate Similarity NPC471532
0.7778 Intermediate Similarity NPC196091
0.7778 Intermediate Similarity NPC471568
0.7778 Intermediate Similarity NPC473693
0.7778 Intermediate Similarity NPC40234
0.7742 Intermediate Similarity NPC471049
0.7742 Intermediate Similarity NPC471048
0.7742 Intermediate Similarity NPC471050
0.7735 Intermediate Similarity NPC89831
0.7727 Intermediate Similarity NPC287757
0.7727 Intermediate Similarity NPC319320
0.7717 Intermediate Similarity NPC194671
0.7717 Intermediate Similarity NPC269750
0.7717 Intermediate Similarity NPC475421
0.7709 Intermediate Similarity NPC471771
0.7709 Intermediate Similarity NPC290755
0.7709 Intermediate Similarity NPC304074
0.7705 Intermediate Similarity NPC196243
0.7661 Intermediate Similarity NPC16188
0.7654 Intermediate Similarity NPC223207
0.7654 Intermediate Similarity NPC472923
0.7611 Intermediate Similarity NPC254700
0.7594 Intermediate Similarity NPC470903
0.7594 Intermediate Similarity NPC167763
0.7594 Intermediate Similarity NPC470112
0.7582 Intermediate Similarity NPC46009
0.7579 Intermediate Similarity NPC124626
0.7569 Intermediate Similarity NPC141957
0.7556 Intermediate Similarity NPC63931
0.7543 Intermediate Similarity NPC202198
0.7514 Intermediate Similarity NPC61004
0.7513 Intermediate Similarity NPC299806
0.75 Intermediate Similarity NPC6913
0.7486 Intermediate Similarity NPC469243
0.7486 Intermediate Similarity NPC276506
0.7486 Intermediate Similarity NPC475123
0.7486 Intermediate Similarity NPC198254
0.7486 Intermediate Similarity NPC475204
0.7486 Intermediate Similarity NPC274198
0.7486 Intermediate Similarity NPC475544
0.7473 Intermediate Similarity NPC328649
0.7473 Intermediate Similarity NPC473502
0.7459 Intermediate Similarity NPC471165
0.7435 Intermediate Similarity NPC94862
0.7429 Intermediate Similarity NPC324081
0.7425 Intermediate Similarity NPC244866
0.7423 Intermediate Similarity NPC302715
0.7421 Intermediate Similarity NPC229234
0.7414 Intermediate Similarity NPC5462
0.7414 Intermediate Similarity NPC9373
0.7405 Intermediate Similarity NPC248670
0.7391 Intermediate Similarity NPC317272
0.7391 Intermediate Similarity NPC268503
0.7391 Intermediate Similarity NPC42549
0.7391 Intermediate Similarity NPC240841
0.7391 Intermediate Similarity NPC256012
0.7391 Intermediate Similarity NPC250846
0.7384 Intermediate Similarity NPC66518
0.7368 Intermediate Similarity NPC476989
0.7363 Intermediate Similarity NPC158900
0.7358 Intermediate Similarity NPC240130
0.7358 Intermediate Similarity NPC61332
0.7344 Intermediate Similarity NPC4910
0.7341 Intermediate Similarity NPC222039
0.7341 Intermediate Similarity NPC100478
0.732 Intermediate Similarity NPC248822
0.731 Intermediate Similarity NPC281629
0.731 Intermediate Similarity NPC471592
0.7288 Intermediate Similarity NPC153644
0.7263 Intermediate Similarity NPC473580
0.7263 Intermediate Similarity NPC473404
0.7262 Intermediate Similarity NPC114102
0.7254 Intermediate Similarity NPC329731
0.7253 Intermediate Similarity NPC241794
0.7247 Intermediate Similarity NPC261934
0.7247 Intermediate Similarity NPC262166
0.7247 Intermediate Similarity NPC5194
0.7245 Intermediate Similarity NPC65714
0.7232 Intermediate Similarity NPC115144
0.7232 Intermediate Similarity NPC277857
0.7232 Intermediate Similarity NPC473491
0.7219 Intermediate Similarity NPC470392
0.7219 Intermediate Similarity NPC214869
0.7214 Intermediate Similarity NPC311357
0.7211 Intermediate Similarity NPC153554
0.7208 Intermediate Similarity NPC184933
0.7208 Intermediate Similarity NPC59827
0.7207 Intermediate Similarity NPC478189
0.7206 Intermediate Similarity NPC478005
0.72 Intermediate Similarity NPC477551
0.72 Intermediate Similarity NPC81026
0.72 Intermediate Similarity NPC469689
0.72 Intermediate Similarity NPC471031
0.7194 Intermediate Similarity NPC41122
0.7194 Intermediate Similarity NPC318805
0.7191 Intermediate Similarity NPC24233
0.7191 Intermediate Similarity NPC147390
0.7191 Intermediate Similarity NPC135538
0.7191 Intermediate Similarity NPC428
0.7191 Intermediate Similarity NPC246587
0.7191 Intermediate Similarity NPC476571
0.7181 Intermediate Similarity NPC136797
0.7181 Intermediate Similarity NPC158277
0.7175 Intermediate Similarity NPC132771
0.7175 Intermediate Similarity NPC245974
0.7173 Intermediate Similarity NPC73555
0.7173 Intermediate Similarity NPC329816
0.7172 Intermediate Similarity NPC473371
0.717 Intermediate Similarity NPC470846
0.7167 Intermediate Similarity NPC127402
0.716 Intermediate Similarity NPC257390
0.7159 Intermediate Similarity NPC247298
0.7151 Intermediate Similarity NPC242159
0.7151 Intermediate Similarity NPC56685
0.7151 Intermediate Similarity NPC313694
0.7151 Intermediate Similarity NPC182119
0.7143 Intermediate Similarity NPC477526
0.7143 Intermediate Similarity NPC266741
0.7143 Intermediate Similarity NPC475215
0.7143 Intermediate Similarity NPC108434
0.7143 Intermediate Similarity NPC82056
0.7135 Intermediate Similarity NPC191376
0.7135 Intermediate Similarity NPC321505
0.7135 Intermediate Similarity NPC179825
0.7128 Intermediate Similarity NPC102959
0.7128 Intermediate Similarity NPC66573
0.7114 Intermediate Similarity NPC475654
0.7111 Intermediate Similarity NPC39431
0.7101 Intermediate Similarity NPC326333
0.7101 Intermediate Similarity NPC52029
0.7101 Intermediate Similarity NPC195749
0.7101 Intermediate Similarity NPC35961
0.7101 Intermediate Similarity NPC241354
0.71 Intermediate Similarity NPC477552
0.71 Intermediate Similarity NPC293624
0.71 Intermediate Similarity NPC477527
0.71 Intermediate Similarity NPC477550
0.7097 Intermediate Similarity NPC302597
0.7095 Intermediate Similarity NPC470935
0.7095 Intermediate Similarity NPC471032
0.7092 Intermediate Similarity NPC60516
0.7089 Intermediate Similarity NPC148124
0.7088 Intermediate Similarity NPC207675
0.7088 Intermediate Similarity NPC212699
0.7081 Intermediate Similarity NPC135006
0.7076 Intermediate Similarity NPC313737
0.7076 Intermediate Similarity NPC285078
0.7076 Intermediate Similarity NPC6854
0.7072 Intermediate Similarity NPC476268
0.7071 Intermediate Similarity NPC314083
0.7069 Intermediate Similarity NPC231572
0.7068 Intermediate Similarity NPC119652
0.7068 Intermediate Similarity NPC97526
0.7065 Intermediate Similarity NPC267414
0.7062 Intermediate Similarity NPC102760
0.7062 Intermediate Similarity NPC30779
0.7062 Intermediate Similarity NPC235194

  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 NPC234069 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
0.7989 Intermediate Similarity NPD6851 Approved
0.7989 Intermediate Similarity NPD6853 Approved
0.7978 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7967 Intermediate Similarity NPD6297 Approved
0.7877 Intermediate Similarity NPD7608 Discontinued
0.7849 Intermediate Similarity NPD7131 Phase 3
0.7801 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD7280 Phase 3
0.7742 Intermediate Similarity NPD7281 Phase 3
0.7588 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7539 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD8245 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD7811 Phase 3
0.7411 Intermediate Similarity NPD7810 Phase 3
0.7409 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD5773 Approved
0.7389 Intermediate Similarity NPD5772 Approved
0.7385 Intermediate Similarity NPD4413 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7484 Phase 3
0.7337 Intermediate Similarity NPD7485 Phase 3
0.7333 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7110 Phase 1
0.7278 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7039 Approved
0.7263 Intermediate Similarity NPD7038 Approved
0.7233 Intermediate Similarity NPD7827 Phase 1
0.7219 Intermediate Similarity NPD5745 Approved
0.72 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD5312 Approved
0.7196 Intermediate Similarity NPD5313 Approved
0.7192 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD6385 Approved
0.7182 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD6386 Approved
0.7167 Intermediate Similarity NPD824 Approved
0.7159 Intermediate Similarity NPD5241 Discontinued
0.715 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8019 Approved
0.7135 Intermediate Similarity NPD3146 Approved
0.7135 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD7291 Discontinued
0.7127 Intermediate Similarity NPD6876 Approved
0.7127 Intermediate Similarity NPD6875 Approved
0.7104 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD5746 Approved
0.7074 Intermediate Similarity NPD5137 Approved
0.7072 Intermediate Similarity NPD3455 Phase 2
0.7069 Intermediate Similarity NPD7450 Phase 2
0.7059 Intermediate Similarity NPD5718 Phase 2
0.7056 Intermediate Similarity NPD2488 Approved
0.7056 Intermediate Similarity NPD6505 Approved
0.7056 Intermediate Similarity NPD2490 Approved
0.7056 Intermediate Similarity NPD6504 Approved
0.7043 Intermediate Similarity NPD8303 Discontinued
0.7041 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD4123 Phase 3
0.7028 Intermediate Similarity NPD8318 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD2674 Phase 3
0.7011 Intermediate Similarity NPD7972 Discontinued
0.7005 Intermediate Similarity NPD5677 Discontinued
0.6995 Remote Similarity NPD2494 Approved
0.6995 Remote Similarity NPD2493 Approved
0.6989 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6989 Remote Similarity NPD8031 Discontinued
0.6979 Remote Similarity NPD5485 Approved
0.6979 Remote Similarity NPD5484 Approved
0.6974 Remote Similarity NPD8053 Approved
0.6974 Remote Similarity NPD8054 Approved
0.6973 Remote Similarity NPD5967 Approved
0.6967 Remote Similarity NPD8149 Discontinued
0.6959 Remote Similarity NPD3936 Clinical (unspecified phase)
0.6949 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6949 Remote Similarity NPD4162 Approved
0.6931 Remote Similarity NPD7315 Approved
0.6923 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3687 Approved
0.6923 Remote Similarity NPD3686 Approved
0.6919 Remote Similarity NPD2977 Approved
0.6919 Remote Similarity NPD2978 Approved
0.6912 Remote Similarity NPD3452 Approved
0.6912 Remote Similarity NPD3450 Approved
0.6906 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6898 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6897 Remote Similarity NPD2653 Approved
0.6893 Remote Similarity NPD4582 Approved
0.6893 Remote Similarity NPD4583 Approved
0.6893 Remote Similarity NPD4040 Phase 1
0.6893 Remote Similarity NPD7153 Discontinued
0.6878 Remote Similarity NPD6107 Approved
0.6872 Remote Similarity NPD3692 Discontinued
0.6872 Remote Similarity NPD2219 Phase 1
0.6869 Remote Similarity NPD7906 Approved
0.6869 Remote Similarity NPD4435 Approved
0.6868 Remote Similarity NPD2122 Discontinued
0.686 Remote Similarity NPD3145 Approved
0.686 Remote Similarity NPD3144 Approved
0.6854 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6854 Remote Similarity NPD3060 Approved
0.6851 Remote Similarity NPD3536 Discontinued
0.6851 Remote Similarity NPD4739 Approved
0.6848 Remote Similarity NPD4675 Approved
0.6848 Remote Similarity NPD4678 Approved
0.6848 Remote Similarity NPD1337 Clinical (unspecified phase)
0.6848 Remote Similarity NPD6502 Phase 2
0.6845 Remote Similarity NPD4002 Approved
0.6845 Remote Similarity NPD4004 Approved
0.6839 Remote Similarity NPD6042 Phase 2
0.6839 Remote Similarity NPD42 Phase 2
0.6839 Remote Similarity NPD555 Phase 2
0.6836 Remote Similarity NPD3656 Approved
0.6836 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6821 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6821 Remote Similarity NPD259 Phase 1
0.6818 Remote Similarity NPD4434 Approved
0.6816 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6816 Remote Similarity NPD6331 Phase 2
0.6814 Remote Similarity NPD7565 Approved
0.6813 Remote Similarity NPD7526 Approved
0.6813 Remote Similarity NPD52 Approved
0.6813 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6811 Remote Similarity NPD6677 Suspended
0.6811 Remote Similarity NPD6873 Phase 2
0.6809 Remote Similarity NPD7831 Phase 2
0.6809 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6809 Remote Similarity NPD8070 Approved
0.6809 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6809 Remote Similarity NPD7833 Phase 2
0.6805 Remote Similarity NPD3125 Approved
0.6802 Remote Similarity NPD6618 Phase 2
0.68 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6798 Remote Similarity NPD2975 Approved
0.6798 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6798 Remote Similarity NPD2974 Approved
0.6798 Remote Similarity NPD2973 Approved
0.6788 Remote Similarity NPD7177 Discontinued
0.6784 Remote Similarity NPD4157 Discontinued
0.6784 Remote Similarity NPD9569 Approved
0.6784 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6782 Remote Similarity NPD7669 Phase 3
0.678 Remote Similarity NPD2240 Approved
0.678 Remote Similarity NPD2239 Approved
0.6776 Remote Similarity NPD3640 Phase 3
0.6776 Remote Similarity NPD3639 Approved
0.6776 Remote Similarity NPD1670 Discontinued
0.6776 Remote Similarity NPD3641 Approved
0.6774 Remote Similarity NPD7495 Discontinued
0.6754 Remote Similarity NPD4166 Phase 2
0.674 Remote Similarity NPD6666 Approved
0.674 Remote Similarity NPD6783 Clinical (unspecified phase)
0.674 Remote Similarity NPD6667 Approved
0.6739 Remote Similarity NPD4210 Discontinued
0.6738 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6737 Remote Similarity NPD6746 Phase 2
0.6734 Remote Similarity NPD6089 Clinical (unspecified phase)
0.6734 Remote Similarity NPD3857 Clinical (unspecified phase)
0.6734 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6729 Remote Similarity NPD7047 Phase 3
0.6725 Remote Similarity NPD6584 Phase 3
0.6724 Remote Similarity NPD2245 Discovery
0.6721 Remote Similarity NPD6390 Discontinued
0.6721 Remote Similarity NPD7303 Discontinued
0.6721 Remote Similarity NPD1975 Clinical (unspecified phase)
0.672 Remote Similarity NPD6072 Discontinued
0.6719 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6718 Remote Similarity NPD5557 Phase 1
0.6718 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6716 Remote Similarity NPD5564 Approved
0.6699 Remote Similarity NPD8161 Suspended
0.6699 Remote Similarity NPD4580 Approved
0.6699 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6697 Remote Similarity NPD6997 Phase 2
0.6686 Remote Similarity NPD6346 Approved
0.6686 Remote Similarity NPD825 Approved
0.6686 Remote Similarity NPD826 Approved
0.6685 Remote Similarity NPD2161 Phase 2
0.6685 Remote Similarity NPD1537 Approved
0.6685 Remote Similarity NPD1538 Phase 1
0.6685 Remote Similarity NPD1519 Approved
0.6685 Remote Similarity NPD8323 Discontinued
0.6685 Remote Similarity NPD6032 Approved
0.6684 Remote Similarity NPD5355 Approved
0.6684 Remote Similarity NPD2489 Approved
0.6684 Remote Similarity NPD27 Approved
0.6684 Remote Similarity NPD6862 Phase 2
0.6684 Remote Similarity NPD5356 Approved
0.6667 Remote Similarity NPD5095 Phase 3
0.6667 Remote Similarity NPD4237 Approved
0.6667 Remote Similarity NPD2968 Approved
0.6667 Remote Similarity NPD5096 Phase 3
0.6667 Remote Similarity NPD2971 Approved
0.6667 Remote Similarity NPD4236 Phase 3
0.6667 Remote Similarity NPD6896 Approved
0.6667 Remote Similarity NPD6895 Approved
0.6667 Remote Similarity NPD1771 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3933 Discontinued
0.6649 Remote Similarity NPD2904 Discontinued
0.6649 Remote Similarity NPD6668 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