Structure

Physi-Chem Properties

Molecular Weight:  934.4
Volume:  911.12
LogP:  -0.066
LogD:  0.396
LogS:  -3.255
# Rotatable Bonds:  6
TPSA:  286.3
# H-Bond Aceptor:  21
# H-Bond Donor:  8
# Rings:  7
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.14
Synthetic Accessibility Score:  7.391
Fsp3:  0.478
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:  -6.402
MDCK Permeability:  1.4674265003122855e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.992
Human Intestinal Absorption (HIA):  0.866
20% Bioavailability (F20%):  0.097
30% Bioavailability (F30%):  0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.144
Plasma Protein Binding (PPB):  65.84197235107422%
Volume Distribution (VD):  0.356
Pgp-substrate:  28.10727310180664%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.025
CYP2C19-inhibitor:  0.034
CYP2C19-substrate:  0.067
CYP2C9-inhibitor:  0.026
CYP2C9-substrate:  0.051
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.188
CYP3A4-inhibitor:  0.318
CYP3A4-substrate:  0.084

ADMET: Excretion

Clearance (CL):  1.338
Half-life (T1/2):  0.156

ADMET: Toxicity

hERG Blockers:  0.048
Human Hepatotoxicity (H-HT):  0.978
Drug-inuced Liver Injury (DILI):  0.947
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.067
Maximum Recommended Daily Dose:  0.797
Skin Sensitization:  0.018
Carcinogencity:  0.012
Eye Corrosion:  0.003
Eye Irritation:  0.003
Respiratory Toxicity:  0.05

Download Data

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

  Natural Product: NPC144314

Natural Product ID:  NPC144314
Common Name*:   Rubiyunnanin H
IUPAC Name:   n.a.
Synonyms:   Rubiyunnanin H
Standard InCHIKey:  ZDSCVBHZIXKZSG-DMUSRQITSA-N
Standard InCHI:  InChI=1S/C46H58N6O15/c1-22-40(58)48-23(2)43(61)50(4)30(18-25-8-13-28(64-7)14-9-25)41(59)49-24(3)44(62)51(5)31-19-26-10-15-29(16-11-26)65-33-20-27(36(54)35(42(60)47-22)52(6)45(31)63)12-17-32(33)66-46-39(57)38(56)37(55)34(21-53)67-46/h8-17,20,22-24,30-31,34-39,46,53-57H,18-19,21H2,1-7H3,(H,47,60)(H,48,58)(H,49,59)/t22-,23+,24+,30+,31+,34-,35+,36+,37-,38+,39-,46-/m1/s1
SMILES:  C[C@@H]1C(=N[C@@H](C)C(=O)N(C)[C@@H](Cc2ccc(cc2)OC)C(=N[C@@H](C)C(=O)N(C)[C@H]2Cc3ccc(cc3)Oc3cc(ccc3O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)[C@@H]([C@@H](C(=N1)O)N(C)C2=O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1288987
PubChem CID:   52942230
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 n.a. root n.a. PMID[21973054]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota roots n.a. 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 = 41350.0 nM PMID[524454]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 50000.0 nM PMID[524454]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 35970.0 nM PMID[524454]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 50000.0 nM PMID[524454]
NPT90 Cell Line DU-145 Homo sapiens IC50 > 50000.0 nM PMID[524454]
NPT306 Cell Line PC-3 Homo sapiens IC50 > 50000.0 nM PMID[524454]
NPT81 Cell Line A549 Homo sapiens IC50 = 32820.0 nM PMID[524454]
NPT547 Cell Line BGC-823 Homo sapiens IC50 > 50000.0 nM PMID[524454]
NPT165 Cell Line HeLa Homo sapiens IC50 = 48170.0 nM PMID[524454]
NPT380 Cell Line U-251 Homo sapiens IC50 = 42310.0 nM PMID[524454]
NPT319 Cell Line B16 Mus musculus IC50 = 29240.0 nM PMID[524454]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 12680.0 nM PMID[524454]
NPT2 Others Unspecified IC50 > 25.0 ug.mL-1 PMID[524454]

☑ 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 NPC144314 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
0.9943 High Similarity NPC50548
0.9943 High Similarity NPC149962
0.9774 High Similarity NPC123859
0.9719 High Similarity NPC242728
0.9 High Similarity NPC29531
0.8977 High Similarity NPC32064
0.8966 High Similarity NPC164608
0.8939 High Similarity NPC276120
0.8804 High Similarity NPC471563
0.8778 High Similarity NPC138083
0.8689 High Similarity NPC174122
0.8689 High Similarity NPC64140
0.8634 High Similarity NPC234069
0.8385 Intermediate Similarity NPC311357
0.8148 Intermediate Similarity NPC473378
0.8148 Intermediate Similarity NPC473407
0.7979 Intermediate Similarity NPC315542
0.7935 Intermediate Similarity NPC155506
0.7935 Intermediate Similarity NPC159767
0.7879 Intermediate Similarity NPC473460
0.7871 Intermediate Similarity NPC326333
0.7839 Intermediate Similarity NPC473422
0.7838 Intermediate Similarity NPC473402
0.7838 Intermediate Similarity NPC473354
0.7831 Intermediate Similarity NPC294951
0.7826 Intermediate Similarity NPC230611
0.7807 Intermediate Similarity NPC45037
0.7794 Intermediate Similarity NPC326027
0.7778 Intermediate Similarity NPC471526
0.7772 Intermediate Similarity NPC196091
0.7766 Intermediate Similarity NPC267414
0.7765 Intermediate Similarity NPC56635
0.7742 Intermediate Similarity NPC476227
0.7714 Intermediate Similarity NPC475292
0.7714 Intermediate Similarity NPC475349
0.7714 Intermediate Similarity NPC475565
0.7705 Intermediate Similarity NPC254700
0.7688 Intermediate Similarity NPC306804
0.7688 Intermediate Similarity NPC273755
0.7685 Intermediate Similarity NPC471561
0.7684 Intermediate Similarity NPC471032
0.7684 Intermediate Similarity NPC470935
0.7663 Intermediate Similarity NPC107938
0.7663 Intermediate Similarity NPC294516
0.7647 Intermediate Similarity NPC26108
0.7633 Intermediate Similarity NPC471531
0.7632 Intermediate Similarity NPC476321
0.763 Intermediate Similarity NPC475442
0.7629 Intermediate Similarity NPC473305
0.7629 Intermediate Similarity NPC163961
0.761 Intermediate Similarity NPC471532
0.7609 Intermediate Similarity NPC179250
0.7609 Intermediate Similarity NPC50380
0.7606 Intermediate Similarity NPC248903
0.7606 Intermediate Similarity NPC50016
0.7594 Intermediate Similarity NPC475624
0.7594 Intermediate Similarity NPC137627
0.7583 Intermediate Similarity NPC148124
0.7581 Intermediate Similarity NPC40234
0.7569 Intermediate Similarity NPC18249
0.7569 Intermediate Similarity NPC10221
0.7569 Intermediate Similarity NPC187028
0.7569 Intermediate Similarity NPC140915
0.7569 Intermediate Similarity NPC305700
0.7569 Intermediate Similarity NPC197741
0.7559 Intermediate Similarity NPC26928
0.7553 Intermediate Similarity NPC279871
0.7553 Intermediate Similarity NPC471165
0.7552 Intermediate Similarity NPC471048
0.7552 Intermediate Similarity NPC471049
0.7552 Intermediate Similarity NPC471050
0.755 Intermediate Similarity NPC475654
0.7542 Intermediate Similarity NPC139699
0.7542 Intermediate Similarity NPC116229
0.7542 Intermediate Similarity NPC114659
0.754 Intermediate Similarity NPC89831
0.7536 Intermediate Similarity NPC99724
0.7528 Intermediate Similarity NPC115144
0.7528 Intermediate Similarity NPC277857
0.7527 Intermediate Similarity NPC287757
0.7527 Intermediate Similarity NPC319320
0.7527 Intermediate Similarity NPC186617
0.7526 Intermediate Similarity NPC269750
0.7526 Intermediate Similarity NPC194671
0.7526 Intermediate Similarity NPC475421
0.75 Intermediate Similarity NPC63628
0.75 Intermediate Similarity NPC178466
0.7487 Intermediate Similarity NPC471568
0.7487 Intermediate Similarity NPC473693
0.7459 Intermediate Similarity NPC472923
0.7447 Intermediate Similarity NPC252960
0.7435 Intermediate Similarity NPC49353
0.7418 Intermediate Similarity NPC470846
0.7418 Intermediate Similarity NPC471073
0.7418 Intermediate Similarity NPC270811
0.7411 Intermediate Similarity NPC477526
0.7409 Intermediate Similarity NPC167763
0.7409 Intermediate Similarity NPC470903
0.7409 Intermediate Similarity NPC470112
0.7407 Intermediate Similarity NPC248670
0.7402 Intermediate Similarity NPC477666
0.7398 Intermediate Similarity NPC230098
0.7394 Intermediate Similarity NPC198741
0.7394 Intermediate Similarity NPC90984
0.7389 Intermediate Similarity NPC233702
0.7382 Intermediate Similarity NPC2314
0.7374 Intermediate Similarity NPC473716
0.7374 Intermediate Similarity NPC475597
0.7374 Intermediate Similarity NPC245974
0.7363 Intermediate Similarity NPC477550
0.7363 Intermediate Similarity NPC229882
0.7363 Intermediate Similarity NPC477552
0.7363 Intermediate Similarity NPC158635
0.7358 Intermediate Similarity NPC329816
0.7351 Intermediate Similarity NPC131532
0.7348 Intermediate Similarity NPC182119
0.7347 Intermediate Similarity NPC34780
0.7337 Intermediate Similarity NPC115466
0.7337 Intermediate Similarity NPC299706
0.7337 Intermediate Similarity NPC61604
0.7337 Intermediate Similarity NPC245615
0.7333 Intermediate Similarity NPC299806
0.7333 Intermediate Similarity NPC102760
0.733 Intermediate Similarity NPC257266
0.7313 Intermediate Similarity NPC281629
0.7308 Intermediate Similarity NPC111785
0.7302 Intermediate Similarity NPC46009
0.7302 Intermediate Similarity NPC329717
0.73 Intermediate Similarity NPC59827
0.73 Intermediate Similarity NPC184933
0.7299 Intermediate Similarity NPC187194
0.7295 Intermediate Similarity NPC257728
0.7291 Intermediate Similarity NPC477551
0.7287 Intermediate Similarity NPC328649
0.7287 Intermediate Similarity NPC473502
0.7287 Intermediate Similarity NPC218614
0.7286 Intermediate Similarity NPC41122
0.7286 Intermediate Similarity NPC318805
0.7282 Intermediate Similarity NPC473562
0.7273 Intermediate Similarity NPC63931
0.7273 Intermediate Similarity NPC4304
0.7273 Intermediate Similarity NPC470413
0.7273 Intermediate Similarity NPC133984
0.7273 Intermediate Similarity NPC138738
0.7268 Intermediate Similarity NPC235698
0.7263 Intermediate Similarity NPC247298
0.7263 Intermediate Similarity NPC16188
0.726 Intermediate Similarity NPC153365
0.726 Intermediate Similarity NPC293347
0.7259 Intermediate Similarity NPC94862
0.725 Intermediate Similarity NPC314083
0.725 Intermediate Similarity NPC24260
0.7246 Intermediate Similarity NPC258128
0.7246 Intermediate Similarity NPC79130
0.7245 Intermediate Similarity NPC248642
0.7238 Intermediate Similarity NPC476743
0.7238 Intermediate Similarity NPC324081
0.723 Intermediate Similarity NPC82056
0.7228 Intermediate Similarity NPC234318
0.7222 Intermediate Similarity NPC5462
0.7222 Intermediate Similarity NPC9373
0.7222 Intermediate Similarity NPC124626
0.7219 Intermediate Similarity NPC163635
0.7211 Intermediate Similarity NPC475204
0.7211 Intermediate Similarity NPC474858
0.7211 Intermediate Similarity NPC475123
0.7208 Intermediate Similarity NPC156576
0.7206 Intermediate Similarity NPC471031
0.7206 Intermediate Similarity NPC469689
0.72 Intermediate Similarity NPC476411
0.72 Intermediate Similarity NPC475754
0.7198 Intermediate Similarity NPC476744
0.7198 Intermediate Similarity NPC475768
0.7194 Intermediate Similarity NPC474607
0.7192 Intermediate Similarity NPC477527
0.7191 Intermediate Similarity NPC106944
0.7189 Intermediate Similarity NPC134905
0.7189 Intermediate Similarity NPC36130
0.7188 Intermediate Similarity NPC136797
0.7188 Intermediate Similarity NPC158277
0.7188 Intermediate Similarity NPC474953
0.7186 Intermediate Similarity NPC61332
0.7186 Intermediate Similarity NPC240130
0.7186 Intermediate Similarity NPC237579
0.7178 Intermediate Similarity NPC308709
0.7174 Intermediate Similarity NPC127402
0.7166 Intermediate Similarity NPC10205
0.7164 Intermediate Similarity NPC302715
0.7162 Intermediate Similarity NPC314743
0.7158 Intermediate Similarity NPC262166
0.7158 Intermediate Similarity NPC202198
0.7157 Intermediate Similarity NPC30779
0.7157 Intermediate Similarity NPC474650
0.7157 Intermediate Similarity NPC229234
0.7151 Intermediate Similarity NPC100478
0.7151 Intermediate Similarity NPC107602
0.7151 Intermediate Similarity NPC137813
0.7151 Intermediate Similarity NPC222039
0.715 Intermediate Similarity NPC248822
0.715 Intermediate Similarity NPC169605

  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 NPC144314 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
0.7978 Intermediate Similarity NPD5773 Approved
0.7978 Intermediate Similarity NPD5772 Approved
0.7968 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7795 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD7131 Phase 3
0.7722 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7696 Intermediate Similarity NPD6853 Approved
0.7696 Intermediate Similarity NPD6851 Approved
0.7588 Intermediate Similarity NPD7810 Phase 3
0.7588 Intermediate Similarity NPD7811 Phase 3
0.7581 Intermediate Similarity NPD7608 Discontinued
0.7579 Intermediate Similarity NPD6297 Approved
0.7554 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7552 Intermediate Similarity NPD7280 Phase 3
0.7552 Intermediate Similarity NPD7281 Phase 3
0.7539 Intermediate Similarity NPD7039 Approved
0.7539 Intermediate Similarity NPD7038 Approved
0.7486 Intermediate Similarity NPD2978 Approved
0.7486 Intermediate Similarity NPD2977 Approved
0.7423 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD8031 Discontinued
0.7366 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD2122 Discontinued
0.734 Intermediate Similarity NPD7485 Phase 3
0.734 Intermediate Similarity NPD7484 Phase 3
0.7333 Intermediate Similarity NPD4123 Phase 3
0.733 Intermediate Similarity NPD7583 Approved
0.7321 Intermediate Similarity NPD7827 Phase 1
0.7295 Intermediate Similarity NPD7585 Approved
0.7277 Intermediate Similarity NPD8318 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD5137 Approved
0.7263 Intermediate Similarity NPD8323 Discontinued
0.7263 Intermediate Similarity NPD5241 Discontinued
0.7236 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD4678 Approved
0.7228 Intermediate Similarity NPD4675 Approved
0.7222 Intermediate Similarity NPD7906 Approved
0.7222 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7291 Discontinued
0.7213 Intermediate Similarity NPD3687 Approved
0.7213 Intermediate Similarity NPD3686 Approved
0.7189 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD2493 Approved
0.7171 Intermediate Similarity NPD2494 Approved
0.7167 Intermediate Similarity NPD2219 Phase 1
0.7163 Intermediate Similarity NPD7584 Approved
0.7157 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2975 Approved
0.7143 Intermediate Similarity NPD2973 Approved
0.7143 Intermediate Similarity NPD2974 Approved
0.7123 Intermediate Similarity NPD8059 Phase 3
0.7123 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD42 Phase 2
0.7113 Intermediate Similarity NPD6042 Phase 2
0.7105 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD5677 Discontinued
0.7104 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD52 Approved
0.7104 Intermediate Similarity NPD7526 Approved
0.7097 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6385 Approved
0.7097 Intermediate Similarity NPD7110 Phase 1
0.7097 Intermediate Similarity NPD6386 Approved
0.7095 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD5192 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD3452 Approved
0.7087 Intermediate Similarity NPD3450 Approved
0.7071 Intermediate Similarity NPD8054 Approved
0.7071 Intermediate Similarity NPD8053 Approved
0.7067 Intermediate Similarity NPD4583 Approved
0.7067 Intermediate Similarity NPD4582 Approved
0.7065 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7047 Phase 3
0.7056 Intermediate Similarity NPD3936 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD4236 Phase 3
0.7056 Intermediate Similarity NPD4237 Approved
0.7056 Intermediate Similarity NPD3060 Approved
0.7056 Intermediate Similarity NPD4162 Approved
0.705 Intermediate Similarity NPD6843 Phase 3
0.705 Intermediate Similarity NPD6841 Approved
0.705 Intermediate Similarity NPD6842 Approved
0.7049 Intermediate Similarity NPD3146 Approved
0.7049 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD4413 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD4580 Approved
0.7031 Intermediate Similarity NPD3051 Approved
0.7024 Intermediate Similarity NPD4420 Approved
0.7019 Intermediate Similarity NPD4004 Approved
0.7019 Intermediate Similarity NPD4002 Approved
0.7 Intermediate Similarity NPD4663 Approved
0.7 Intermediate Similarity NPD8070 Approved
0.7 Intermediate Similarity NPD3857 Clinical (unspecified phase)
0.6995 Remote Similarity NPD2970 Approved
0.6995 Remote Similarity NPD2969 Approved
0.698 Remote Similarity NPD2488 Approved
0.698 Remote Similarity NPD2490 Approved
0.6971 Remote Similarity NPD5718 Phase 2
0.6965 Remote Similarity NPD4157 Discontinued
0.6961 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6957 Remote Similarity NPD4739 Approved
0.6954 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7007 Discovery
0.6952 Remote Similarity NPD8161 Suspended
0.6952 Remote Similarity NPD8417 Discontinued
0.6946 Remote Similarity NPD7296 Approved
0.6941 Remote Similarity NPD6997 Phase 2
0.694 Remote Similarity NPD8152 Approved
0.694 Remote Similarity NPD8153 Approved
0.6939 Remote Similarity NPD8156 Discontinued
0.6939 Remote Similarity NPD5312 Approved
0.6939 Remote Similarity NPD5313 Approved
0.6939 Remote Similarity NPD7054 Approved
0.6935 Remote Similarity NPD4577 Approved
0.6935 Remote Similarity NPD4578 Approved
0.6935 Remote Similarity NPD4210 Discontinued
0.6934 Remote Similarity NPD8151 Discontinued
0.6932 Remote Similarity NPD5745 Approved
0.6931 Remote Similarity NPD8455 Phase 2
0.6931 Remote Similarity NPD7972 Discontinued
0.6927 Remote Similarity NPD6746 Phase 2
0.6919 Remote Similarity NPD7613 Discontinued
0.6915 Remote Similarity NPD6072 Discontinued
0.6911 Remote Similarity NPD5604 Discontinued
0.6904 Remote Similarity NPD7074 Phase 3
0.6904 Remote Similarity NPD7472 Approved
0.6904 Remote Similarity NPD3885 Approved
0.6898 Remote Similarity NPD8149 Discontinued
0.6898 Remote Similarity NPD4005 Discontinued
0.6897 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6895 Remote Similarity NPD5967 Approved
0.689 Remote Similarity NPD5005 Approved
0.689 Remote Similarity NPD5006 Approved
0.6888 Remote Similarity NPD8251 Approved
0.6888 Remote Similarity NPD8099 Discontinued
0.6888 Remote Similarity NPD8252 Approved
0.6887 Remote Similarity NPD7701 Phase 2
0.6885 Remote Similarity NPD3692 Discontinued
0.6884 Remote Similarity NPD7808 Phase 3
0.6875 Remote Similarity NPD5457 Discontinued
0.6872 Remote Similarity NPD27 Approved
0.6872 Remote Similarity NPD2489 Approved
0.6869 Remote Similarity NPD7801 Approved
0.6865 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6865 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6865 Remote Similarity NPD3536 Discontinued
0.6862 Remote Similarity NPD6876 Approved
0.6862 Remote Similarity NPD6875 Approved
0.6851 Remote Similarity NPD1375 Discontinued
0.685 Remote Similarity NPD7312 Approved
0.685 Remote Similarity NPD2968 Approved
0.685 Remote Similarity NPD2971 Approved
0.685 Remote Similarity NPD7311 Approved
0.685 Remote Similarity NPD7310 Approved
0.685 Remote Similarity NPD7313 Approved
0.6848 Remote Similarity NPD6667 Approved
0.6848 Remote Similarity NPD6666 Approved
0.6842 Remote Similarity NPD7046 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6839 Remote Similarity NPD2904 Discontinued
0.6831 Remote Similarity NPD6331 Phase 2
0.6831 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6827 Remote Similarity NPD7565 Approved
0.6825 Remote Similarity NPD6677 Suspended
0.6818 Remote Similarity NPD5746 Approved
0.6816 Remote Similarity NPD7309 Approved
0.681 Remote Similarity NPD6823 Phase 2
0.681 Remote Similarity NPD8398 Clinical (unspecified phase)
0.6806 Remote Similarity NPD6063 Approved
0.6802 Remote Similarity NPD7228 Approved
0.6802 Remote Similarity NPD7177 Discontinued
0.6789 Remote Similarity NPD5722 Discontinued
0.6788 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4481 Phase 3
0.6776 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6774 Remote Similarity NPD7447 Phase 1
0.6771 Remote Similarity NPD6788 Approved
0.6769 Remote Similarity NPD7315 Approved
0.6769 Remote Similarity NPD6071 Discontinued
0.6763 Remote Similarity NPD5582 Discontinued
0.6758 Remote Similarity NPD7266 Discontinued
0.6754 Remote Similarity NPD6668 Clinical (unspecified phase)
0.6753 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6753 Remote Similarity NPD2041 Clinical (unspecified phase)
0.675 Remote Similarity NPD7251 Discontinued
0.6745 Remote Similarity NPD4040 Phase 1
0.674 Remote Similarity NPD6029 Clinical (unspecified phase)
0.674 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6738 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6737 Remote Similarity NPD4773 Phase 2
0.6737 Remote Similarity NPD4772 Phase 2
0.6732 Remote Similarity NPD6504 Approved
0.6732 Remote Similarity NPD6505 Approved
0.6721 Remote Similarity NPD7153 Discontinued
0.672 Remote Similarity NPD1774 Approved
0.672 Remote Similarity NPD5297 Approved
0.672 Remote Similarity NPD7212 Phase 2

  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