Structure

Physi-Chem Properties

Molecular Weight:  740.21
Volume:  721.38
LogP:  6.746
LogD:  2.715
LogS:  -5.305
# Rotatable Bonds:  7
TPSA:  232.9
# H-Bond Aceptor:  14
# H-Bond Donor:  8
# Rings:  7
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.076
Synthetic Accessibility Score:  4.815
Fsp3:  0.25
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:  -6.329
MDCK Permeability:  7.342182470893022e-06
Pgp-inhibitor:  0.804
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.98
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  87.76042938232422%
Volume Distribution (VD):  0.327
Pgp-substrate:  12.973326683044434%

ADMET: Metabolism

CYP1A2-inhibitor:  0.844
CYP1A2-substrate:  0.149
CYP2C19-inhibitor:  0.052
CYP2C19-substrate:  0.041
CYP2C9-inhibitor:  0.504
CYP2C9-substrate:  0.328
CYP2D6-inhibitor:  0.176
CYP2D6-substrate:  0.144
CYP3A4-inhibitor:  0.027
CYP3A4-substrate:  0.02

ADMET: Excretion

Clearance (CL):  2.235
Half-life (T1/2):  0.462

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.933
Drug-inuced Liver Injury (DILI):  0.99
AMES Toxicity:  0.263
Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.926
Carcinogencity:  0.049
Eye Corrosion:  0.003
Eye Irritation:  0.872
Respiratory Toxicity:  0.139

Download Data

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

  Natural Product: NPC475662

Natural Product ID:  NPC475662
Common Name*:   (2S,3R,4R,5S,6S)-5-Hydroxy-6-Methyl-2-((9R,9'r)-2',4,4',5,5'-Pentahydroxy-7,7'-Dimethyl-10,10'-Dioxo-9,9',10,10'-Tetrahydro-9,9'-Bianthracen-2-Yloxy)Tetrahydro-2H-Pyran-3,4-Diyl Diacetate
IUPAC Name:   [(2S,3R,4R,5S,6S)-3-acetyloxy-2-[[(9R)-4,5-dihydroxy-7-methyl-10-oxo-9-[(9R)-2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]-9H-anthracen-2-yl]oxy]-5-hydroxy-6-methyloxan-4-yl] acetate
Synonyms:  
Standard InCHIKey:  YCLAFTNYHWAFCG-WJQWSSJKSA-N
Standard InCHI:  InChI=1S/C40H36O14/c1-14-6-21-29(23-10-19(43)11-27(46)33(23)36(49)31(21)25(44)8-14)30-22-7-15(2)9-26(45)32(22)37(50)34-24(30)12-20(13-28(34)47)54-40-39(53-18(5)42)38(52-17(4)41)35(48)16(3)51-40/h6-13,16,29-30,35,38-40,43-48H,1-5H3/t16-,29+,30+,35-,38+,39+,40-/m0/s1
SMILES:  CC1C(C(C(C(O1)OC2=CC3=C(C(=C2)O)C(=O)C4=C(C3C5C6=C(C(=CC(=C6)C)O)C(=O)C7=C5C=C(C=C7O)O)C=C(C=C4O)C)OC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL510919
PubChem CID:   10876371
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
NPO32935 rhamnus nepalensis Species Rhamnaceae Eukaryota Leaves Pa Co, Mai Chau, Hoa Binh Province, 150 km west of Hanoi, Vietnam 1995-Nov PMID[11575949]

☑ 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
NPT91 Cell Line KB Homo sapiens IC50 = 4500.0 nM PMID[458487]

☑ 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 NPC475662 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 NPC293227
1.0 High Similarity NPC473717
1.0 High Similarity NPC473631
0.9882 High Similarity NPC473686
0.9882 High Similarity NPC221140
0.9882 High Similarity NPC229817
0.9882 High Similarity NPC475352
0.9882 High Similarity NPC475220
0.9521 High Similarity NPC298778
0.9467 High Similarity NPC474345
0.936 High Similarity NPC475161
0.936 High Similarity NPC477860
0.9353 High Similarity NPC68381
0.9353 High Similarity NPC63105
0.931 High Similarity NPC87583
0.9302 High Similarity NPC114257
0.9302 High Similarity NPC299149
0.9302 High Similarity NPC153578
0.9302 High Similarity NPC277710
0.9298 High Similarity NPC46958
0.9294 High Similarity NPC213052
0.9257 High Similarity NPC105591
0.9235 High Similarity NPC271385
0.9235 High Similarity NPC5029
0.9235 High Similarity NPC76128
0.9235 High Similarity NPC111536
0.9235 High Similarity NPC30432
0.9231 High Similarity NPC259905
0.9226 High Similarity NPC178851
0.9209 High Similarity NPC264302
0.9191 High Similarity NPC245059
0.9191 High Similarity NPC84494
0.9186 High Similarity NPC170018
0.9186 High Similarity NPC475246
0.9186 High Similarity NPC66820
0.9186 High Similarity NPC92403
0.9186 High Similarity NPC76112
0.9181 High Similarity NPC168789
0.9176 High Similarity NPC76047
0.9172 High Similarity NPC249977
0.9167 High Similarity NPC7752
0.9148 High Similarity NPC65489
0.9138 High Similarity NPC164047
0.9138 High Similarity NPC470453
0.9138 High Similarity NPC470448
0.9138 High Similarity NPC470452
0.9128 High Similarity NPC3718
0.9128 High Similarity NPC199533
0.9128 High Similarity NPC470454
0.9091 High Similarity NPC241847
0.9086 High Similarity NPC321916
0.9075 High Similarity NPC475233
0.907 High Similarity NPC472054
0.907 High Similarity NPC85368
0.9056 High Similarity NPC470197
0.9056 High Similarity NPC282474
0.9056 High Similarity NPC470200
0.9056 High Similarity NPC470194
0.9056 High Similarity NPC470193
0.9056 High Similarity NPC470196
0.9056 High Similarity NPC316274
0.9056 High Similarity NPC470198
0.9056 High Similarity NPC470195
0.9034 High Similarity NPC75574
0.9034 High Similarity NPC318119
0.9034 High Similarity NPC231254
0.9006 High Similarity NPC473202
0.9006 High Similarity NPC222455
0.9 High Similarity NPC260504
0.9 High Similarity NPC473278
0.9 High Similarity NPC89809
0.8977 High Similarity NPC132111
0.8977 High Similarity NPC313452
0.8971 High Similarity NPC471030
0.8971 High Similarity NPC179862
0.8971 High Similarity NPC212290
0.8966 High Similarity NPC289876
0.896 High Similarity NPC203751
0.896 High Similarity NPC98776
0.8953 High Similarity NPC188815
0.8953 High Similarity NPC469344
0.8944 High Similarity NPC470199
0.8944 High Similarity NPC314459
0.8941 High Similarity NPC99216
0.8941 High Similarity NPC469664
0.8939 High Similarity NPC31208
0.8939 High Similarity NPC472724
0.8939 High Similarity NPC472720
0.8939 High Similarity NPC160543
0.8939 High Similarity NPC472721
0.8939 High Similarity NPC314672
0.8939 High Similarity NPC469652
0.8939 High Similarity NPC93065
0.8935 High Similarity NPC15374
0.8935 High Similarity NPC97637
0.8935 High Similarity NPC187934
0.8935 High Similarity NPC216752
0.8933 High Similarity NPC469649
0.8933 High Similarity NPC260521
0.892 High Similarity NPC315221
0.8908 High Similarity NPC146803
0.8908 High Similarity NPC470667
0.8907 High Similarity NPC174140
0.8902 High Similarity NPC221288
0.8902 High Similarity NPC217822
0.8902 High Similarity NPC137871
0.8902 High Similarity NPC477836
0.8902 High Similarity NPC9002
0.8902 High Similarity NPC101399
0.8902 High Similarity NPC11847
0.8902 High Similarity NPC257011
0.8902 High Similarity NPC288152
0.8889 High Similarity NPC477835
0.8889 High Similarity NPC48474
0.8883 High Similarity NPC223534
0.8883 High Similarity NPC158214
0.8883 High Similarity NPC290289
0.8883 High Similarity NPC240200
0.8882 High Similarity NPC257566
0.8882 High Similarity NPC124155
0.8876 High Similarity NPC18380
0.8876 High Similarity NPC111490
0.8876 High Similarity NPC261623
0.8876 High Similarity NPC469650
0.8864 High Similarity NPC58538
0.8857 High Similarity NPC102053
0.8851 High Similarity NPC25724
0.8844 High Similarity NPC210808
0.8844 High Similarity NPC280642
0.8844 High Similarity NPC199079
0.8844 High Similarity NPC96605
0.8844 High Similarity NPC218161
0.8837 High Similarity NPC472622
0.8833 High Similarity NPC187632
0.883 High Similarity NPC475979
0.883 High Similarity NPC294722
0.883 High Similarity NPC178281
0.8827 High Similarity NPC475179
0.8827 High Similarity NPC64755
0.8824 High Similarity NPC190450
0.8824 High Similarity NPC44947
0.8824 High Similarity NPC472876
0.8824 High Similarity NPC473012
0.8817 High Similarity NPC184326
0.8817 High Similarity NPC328093
0.8817 High Similarity NPC292863
0.8814 High Similarity NPC208069
0.8814 High Similarity NPC197357
0.8814 High Similarity NPC85316
0.881 High Similarity NPC324358
0.881 High Similarity NPC318527
0.881 High Similarity NPC322459
0.881 High Similarity NPC323627
0.881 High Similarity NPC257166
0.8807 High Similarity NPC267549
0.88 High Similarity NPC186800
0.8798 High Similarity NPC3474
0.8793 High Similarity NPC4200
0.8793 High Similarity NPC67134
0.8793 High Similarity NPC47140
0.8791 High Similarity NPC477082
0.8791 High Similarity NPC476358
0.8786 High Similarity NPC470207
0.8786 High Similarity NPC5319
0.8786 High Similarity NPC300307
0.8786 High Similarity NPC470206
0.8785 High Similarity NPC471091
0.8785 High Similarity NPC97924
0.8785 High Similarity NPC40078
0.8779 High Similarity NPC70441
0.8779 High Similarity NPC251336
0.8779 High Similarity NPC472621
0.8778 High Similarity NPC205721
0.8778 High Similarity NPC473618
0.8772 High Similarity NPC290160
0.8772 High Similarity NPC473009
0.8771 High Similarity NPC104910
0.8771 High Similarity NPC112380
0.8771 High Similarity NPC474093
0.8765 High Similarity NPC101636
0.8765 High Similarity NPC312273
0.8765 High Similarity NPC477628
0.8765 High Similarity NPC47923
0.8765 High Similarity NPC270675
0.8765 High Similarity NPC97812
0.8765 High Similarity NPC273467
0.8765 High Similarity NPC301256
0.8765 High Similarity NPC472994
0.8765 High Similarity NPC189552
0.8765 High Similarity NPC137232
0.8765 High Similarity NPC477629
0.8765 High Similarity NPC210961
0.8765 High Similarity NPC195685
0.8757 High Similarity NPC51247
0.8757 High Similarity NPC15815
0.8757 High Similarity NPC195167
0.8757 High Similarity NPC308265
0.8757 High Similarity NPC53139
0.8757 High Similarity NPC80956
0.875 High Similarity NPC148323

  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 NPC475662 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
0.9186 High Similarity NPD8313 Approved
0.9186 High Similarity NPD8312 Approved
0.8876 High Similarity NPD6959 Discontinued
0.8827 High Similarity NPD7879 Clinical (unspecified phase)
0.8786 High Similarity NPD7804 Clinical (unspecified phase)
0.8636 High Similarity NPD6559 Discontinued
0.8629 High Similarity NPD7074 Phase 3
0.8624 High Similarity NPD8151 Discontinued
0.8588 High Similarity NPD4381 Clinical (unspecified phase)
0.8571 High Similarity NPD7054 Approved
0.8523 High Similarity NPD7472 Approved
0.8521 High Similarity NPD7819 Suspended
0.8508 High Similarity NPD8397 Clinical (unspecified phase)
0.8483 Intermediate Similarity NPD7808 Phase 3
0.8471 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD7473 Discontinued
0.8427 Intermediate Similarity NPD7251 Discontinued
0.84 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8372 Intermediate Similarity NPD7075 Discontinued
0.8371 Intermediate Similarity NPD6797 Phase 2
0.8362 Intermediate Similarity NPD5844 Phase 1
0.8304 Intermediate Similarity NPD8455 Phase 2
0.8295 Intermediate Similarity NPD6166 Phase 2
0.8295 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8295 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8286 Intermediate Similarity NPD6232 Discontinued
0.8278 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8268 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD7435 Discontinued
0.8247 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.8247 Intermediate Similarity NPD7783 Phase 2
0.8235 Intermediate Similarity NPD4380 Phase 2
0.822 Intermediate Similarity NPD7870 Phase 2
0.822 Intermediate Similarity NPD7871 Phase 2
0.8208 Intermediate Similarity NPD7768 Phase 2
0.8208 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8202 Intermediate Similarity NPD3818 Discontinued
0.8202 Intermediate Similarity NPD7228 Approved
0.8198 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8198 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8187 Intermediate Similarity NPD7411 Suspended
0.8105 Intermediate Similarity NPD6776 Approved
0.8105 Intermediate Similarity NPD6782 Approved
0.8105 Intermediate Similarity NPD6781 Approved
0.8105 Intermediate Similarity NPD6778 Approved
0.8105 Intermediate Similarity NPD6780 Approved
0.8105 Intermediate Similarity NPD6779 Approved
0.8105 Intermediate Similarity NPD6777 Approved
0.8103 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.8103 Intermediate Similarity NPD7874 Approved
0.8095 Intermediate Similarity NPD7390 Discontinued
0.8073 Intermediate Similarity NPD7697 Approved
0.8073 Intermediate Similarity NPD7698 Approved
0.8073 Intermediate Similarity NPD7696 Phase 3
0.807 Intermediate Similarity NPD7458 Discontinued
0.8035 Intermediate Similarity NPD1934 Approved
0.8035 Intermediate Similarity NPD6801 Discontinued
0.8031 Intermediate Similarity NPD8319 Approved
0.8031 Intermediate Similarity NPD8320 Phase 1
0.8 Intermediate Similarity NPD7701 Phase 2
0.797 Intermediate Similarity NPD7801 Approved
0.7941 Intermediate Similarity NPD2534 Approved
0.7941 Intermediate Similarity NPD2532 Approved
0.7941 Intermediate Similarity NPD2533 Approved
0.7931 Intermediate Similarity NPD37 Approved
0.7927 Intermediate Similarity NPD6823 Phase 2
0.7921 Intermediate Similarity NPD7199 Phase 2
0.791 Intermediate Similarity NPD6234 Discontinued
0.7906 Intermediate Similarity NPD7699 Phase 2
0.7906 Intermediate Similarity NPD7700 Phase 2
0.7903 Intermediate Similarity NPD8150 Discontinued
0.7898 Intermediate Similarity NPD4967 Phase 2
0.7898 Intermediate Similarity NPD4965 Approved
0.7898 Intermediate Similarity NPD4966 Approved
0.7882 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD3749 Approved
0.7842 Intermediate Similarity NPD6534 Approved
0.7842 Intermediate Similarity NPD6535 Approved
0.7841 Intermediate Similarity NPD3817 Phase 2
0.7836 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD7240 Approved
0.7816 Intermediate Similarity NPD6599 Discontinued
0.7798 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD3787 Discontinued
0.7765 Intermediate Similarity NPD5494 Approved
0.7759 Intermediate Similarity NPD3226 Approved
0.7759 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD5402 Approved
0.7738 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7705 Intermediate Similarity NPD3751 Discontinued
0.7692 Intermediate Similarity NPD1549 Phase 2
0.7684 Intermediate Similarity NPD1465 Phase 2
0.7684 Intermediate Similarity NPD2801 Approved
0.7674 Intermediate Similarity NPD6799 Approved
0.7644 Intermediate Similarity NPD5403 Approved
0.763 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7604 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7604 Intermediate Similarity NPD6212 Phase 3
0.7604 Intermediate Similarity NPD6213 Phase 3
0.7602 Intermediate Similarity NPD3750 Approved
0.7602 Intermediate Similarity NPD4628 Phase 3
0.7577 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD1511 Approved
0.7544 Intermediate Similarity NPD6674 Discontinued
0.7544 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD7685 Pre-registration
0.7529 Intermediate Similarity NPD5401 Approved
0.7529 Intermediate Similarity NPD2346 Discontinued
0.75 Intermediate Similarity NPD3882 Suspended
0.75 Intermediate Similarity NPD7003 Approved
0.75 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7584 Approved
0.7486 Intermediate Similarity NPD5711 Approved
0.7486 Intermediate Similarity NPD5710 Approved
0.7486 Intermediate Similarity NPD1512 Approved
0.7471 Intermediate Similarity NPD6100 Approved
0.7471 Intermediate Similarity NPD5406 Approved
0.7471 Intermediate Similarity NPD5404 Approved
0.7471 Intermediate Similarity NPD2796 Approved
0.7471 Intermediate Similarity NPD5405 Approved
0.7471 Intermediate Similarity NPD6099 Approved
0.7471 Intermediate Similarity NPD5408 Approved
0.7437 Intermediate Similarity NPD7680 Approved
0.7435 Intermediate Similarity NPD8434 Phase 2
0.7429 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD7930 Approved
0.7412 Intermediate Similarity NPD1510 Phase 2
0.7412 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD1607 Approved
0.7391 Intermediate Similarity NPD7229 Phase 3
0.7368 Intermediate Similarity NPD2935 Discontinued
0.7368 Intermediate Similarity NPD1551 Phase 2
0.7358 Intermediate Similarity NPD8059 Phase 3
0.7358 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7177 Discontinued
0.731 Intermediate Similarity NPD3748 Approved
0.7303 Intermediate Similarity NPD1653 Approved
0.7299 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7291 Intermediate Similarity NPD7585 Approved
0.7288 Intermediate Similarity NPD6273 Approved
0.7278 Intermediate Similarity NPD1240 Approved
0.7277 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD8127 Discontinued
0.7241 Intermediate Similarity NPD7583 Approved
0.7241 Intermediate Similarity NPD2800 Approved
0.7236 Intermediate Similarity NPD8285 Discontinued
0.7211 Intermediate Similarity NPD5953 Discontinued
0.7209 Intermediate Similarity NPD2799 Discontinued
0.7196 Intermediate Similarity NPD7286 Phase 2
0.7193 Intermediate Similarity NPD6651 Approved
0.7151 Intermediate Similarity NPD920 Approved
0.7151 Intermediate Similarity NPD7097 Phase 1
0.7143 Intermediate Similarity NPD4908 Phase 1
0.7143 Intermediate Similarity NPD1243 Approved
0.7135 Intermediate Similarity NPD919 Approved
0.7135 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7266 Discontinued
0.7121 Intermediate Similarity NPD4360 Phase 2
0.7121 Intermediate Similarity NPD4363 Phase 3
0.7114 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7999 Approved
0.7102 Intermediate Similarity NPD8166 Discontinued
0.7088 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD4060 Phase 1
0.7062 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD7799 Discontinued
0.7042 Intermediate Similarity NPD8366 Approved
0.7039 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD5124 Phase 1
0.7035 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD8067 Phase 3
0.7005 Intermediate Similarity NPD4287 Approved
0.7 Intermediate Similarity NPD4625 Phase 3
0.6984 Remote Similarity NPD3926 Phase 2
0.6977 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6977 Remote Similarity NPD1613 Approved
0.6971 Remote Similarity NPD2438 Suspended
0.6963 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6798 Discontinued
0.6959 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6959 Remote Similarity NPD2313 Discontinued
0.6949 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6941 Remote Similarity NPD6832 Phase 2
0.6936 Remote Similarity NPD1933 Approved
0.6936 Remote Similarity NPD230 Phase 1
0.6936 Remote Similarity NPD6355 Discontinued
0.6914 Remote Similarity NPD7033 Discontinued
0.6912 Remote Similarity NPD8491 Approved
0.6898 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6881 Remote Similarity NPD8469 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