Structure

Physi-Chem Properties

Molecular Weight:  822.31
Volume:  795.475
LogP:  4.991
LogD:  1.877
LogS:  -3.247
# Rotatable Bonds:  9
TPSA:  226.2
# H-Bond Aceptor:  16
# H-Bond Donor:  5
# Rings:  8
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.138
Synthetic Accessibility Score:  6.279
Fsp3:  0.558
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:  -5.88
MDCK Permeability:  2.8916985684190877e-05
Pgp-inhibitor:  0.881
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.276
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.011
Plasma Protein Binding (PPB):  98.21285247802734%
Volume Distribution (VD):  0.178
Pgp-substrate:  6.2483954429626465%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.959
CYP2C19-inhibitor:  0.07
CYP2C19-substrate:  0.179
CYP2C9-inhibitor:  0.343
CYP2C9-substrate:  0.59
CYP2D6-inhibitor:  0.034
CYP2D6-substrate:  0.144
CYP3A4-inhibitor:  0.096
CYP3A4-substrate:  0.225

ADMET: Excretion

Clearance (CL):  6.372
Half-life (T1/2):  0.534

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.447
Drug-inuced Liver Injury (DILI):  0.986
AMES Toxicity:  0.968
Rat Oral Acute Toxicity:  0.92
Maximum Recommended Daily Dose:  0.929
Skin Sensitization:  0.803
Carcinogencity:  0.884
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.111

Download Data

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

  Natural Product: NPC65118

Natural Product ID:  NPC65118
Common Name*:   Grincamycin D
IUPAC Name:   (3R)-4-[6-[(2S,4aS,5aR,7R,9R,9aR,10aR)-2,9-dimethyl-3-oxo-4,4a,5a,6,7,9,9a,10a-octahydrodipyrano[4,2-a:4',3'-e][1,4]dioxin-7-yl]-1,5-dihydroxy-9,10-dioxoanthracen-2-yl]-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxybutanoic acid
Synonyms:   Grincamycin D
Standard InCHIKey:  RTZAMMXBZUIQSH-HIAMVLHPSA-N
Standard InCHI:  InChI=1S/C43H50O16/c1-18-26(44)10-12-33(53-18)57-28-11-13-34(54-20(28)3)59-43(5,17-32(46)47)16-22-6-7-24-35(37(22)48)39(50)25-9-8-23(38(49)36(25)40(24)51)29-15-30-41(21(4)52-29)58-42-31(56-30)14-27(45)19(2)55-42/h6-9,18-21,28-31,33-34,41-42,48-49H,10-17H2,1-5H3,(H,46,47)/t18-,19-,20-,21+,28-,29+,30+,31-,33-,34-,41+,42-,43+/m0/s1
SMILES:  C[C@H]1C(=O)CC[C@@H](O1)O[C@H]1CC[C@@H](O[C@H]1C)O[C@](C)(Cc1ccc2c(c1O)C(=O)c1ccc([C@H]3C[C@@H]4[C@@H]([C@@H](C)O3)O[C@H]3[C@H](CC(=O)[C@H](C)O3)O4)c(c1C2=O)O)CC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2011812
PubChem CID:   57332778
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

*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
NPO1930.2 Streptomyces lusitanus scsio lr32 Subspecies Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22304344]

☑ 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
NPT319 Cell Line B16 Mus musculus IC50 = 9700.0 nM PMID[475838]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 9700.0 nM PMID[475838]
NPT1312 Cell Line SW1990 Homo sapiens IC50 = 22000.0 nM PMID[475838]
NPT165 Cell Line HeLa Homo sapiens IC50 = 12000.0 nM PMID[475838]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 30000.0 nM PMID[475838]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 6100.0 nM PMID[475838]

☑ 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 NPC65118 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
0.9877 High Similarity NPC176246
0.9693 High Similarity NPC183441
0.9521 High Similarity NPC72783
0.9458 High Similarity NPC70862
0.9333 High Similarity NPC175477
0.929 High Similarity NPC187441
0.929 High Similarity NPC283980
0.9231 High Similarity NPC83331
0.9118 High Similarity NPC470581
0.9118 High Similarity NPC470582
0.9118 High Similarity NPC115447
0.9107 High Similarity NPC270027
0.9036 High Similarity NPC478026
0.9006 High Similarity NPC266513
0.9 High Similarity NPC19056
0.9 High Similarity NPC470583
0.8935 High Similarity NPC478021
0.8922 High Similarity NPC478020
0.8922 High Similarity NPC478022
0.8902 High Similarity NPC208651
0.8902 High Similarity NPC85316
0.8902 High Similarity NPC206641
0.8902 High Similarity NPC197357
0.8889 High Similarity NPC131405
0.8882 High Similarity NPC294501
0.8848 High Similarity NPC53139
0.8827 High Similarity NPC470200
0.8827 High Similarity NPC316274
0.8827 High Similarity NPC470197
0.8827 High Similarity NPC470198
0.8827 High Similarity NPC470193
0.8827 High Similarity NPC470196
0.8827 High Similarity NPC282474
0.8827 High Similarity NPC470195
0.8827 High Similarity NPC470194
0.8824 High Similarity NPC470580
0.8802 High Similarity NPC97637
0.8802 High Similarity NPC187934
0.88 High Similarity NPC224557
0.88 High Similarity NPC292706
0.878 High Similarity NPC3449
0.8779 High Similarity NPC307754
0.8779 High Similarity NPC223735
0.8728 High Similarity NPC289876
0.8727 High Similarity NPC283480
0.8727 High Similarity NPC148323
0.8715 High Similarity NPC470199
0.8715 High Similarity NPC314459
0.8708 High Similarity NPC314672
0.8686 High Similarity NPC477860
0.8686 High Similarity NPC475161
0.8671 High Similarity NPC470667
0.8671 High Similarity NPC186800
0.8667 High Similarity NPC192219
0.8667 High Similarity NPC174599
0.8667 High Similarity NPC82190
0.8629 High Similarity NPC58538
0.8621 High Similarity NPC232818
0.8621 High Similarity NPC198893
0.8621 High Similarity NPC314489
0.8619 High Similarity NPC314687
0.8613 High Similarity NPC203751
0.8606 High Similarity NPC209393
0.8606 High Similarity NPC205172
0.8588 High Similarity NPC178281
0.8588 High Similarity NPC329647
0.8588 High Similarity NPC470735
0.8587 High Similarity NPC314941
0.8571 High Similarity NPC133775
0.8556 High Similarity NPC48474
0.8555 High Similarity NPC13989
0.8548 High Similarity NPC315889
0.8539 High Similarity NPC87583
0.8539 High Similarity NPC241847
0.8537 High Similarity NPC475407
0.8531 High Similarity NPC313452
0.8514 High Similarity NPC92403
0.8514 High Similarity NPC170018
0.8514 High Similarity NPC76112
0.8514 High Similarity NPC475246
0.8514 High Similarity NPC102053
0.8514 High Similarity NPC46958
0.8514 High Similarity NPC66820
0.8506 High Similarity NPC85368
0.8503 High Similarity NPC478027
0.8494 Intermediate Similarity NPC474621
0.8494 Intermediate Similarity NPC474622
0.8488 Intermediate Similarity NPC63470
0.8475 Intermediate Similarity NPC315221
0.8471 Intermediate Similarity NPC146837
0.8471 Intermediate Similarity NPC212099
0.8471 Intermediate Similarity NPC278329
0.8471 Intermediate Similarity NPC101116
0.8457 Intermediate Similarity NPC68381
0.8457 Intermediate Similarity NPC3718
0.8448 Intermediate Similarity NPC315619
0.8444 Intermediate Similarity NPC205721
0.84 Intermediate Similarity NPC472054
0.8382 Intermediate Similarity NPC471295
0.8372 Intermediate Similarity NPC99216
0.837 Intermediate Similarity NPC108487
0.8364 Intermediate Similarity NPC44378
0.8364 Intermediate Similarity NPC280753
0.8364 Intermediate Similarity NPC120171
0.8344 Intermediate Similarity NPC474630
0.8343 Intermediate Similarity NPC257309
0.8343 Intermediate Similarity NPC30432
0.8343 Intermediate Similarity NPC271385
0.8343 Intermediate Similarity NPC5029
0.8343 Intermediate Similarity NPC111536
0.8343 Intermediate Similarity NPC76128
0.8333 Intermediate Similarity NPC475220
0.8333 Intermediate Similarity NPC221140
0.8333 Intermediate Similarity NPC475352
0.8333 Intermediate Similarity NPC229817
0.8333 Intermediate Similarity NPC246274
0.8333 Intermediate Similarity NPC473686
0.8324 Intermediate Similarity NPC477466
0.8324 Intermediate Similarity NPC477471
0.8324 Intermediate Similarity NPC477469
0.8324 Intermediate Similarity NPC477473
0.8323 Intermediate Similarity NPC474533
0.8323 Intermediate Similarity NPC474534
0.8315 Intermediate Similarity NPC277710
0.8315 Intermediate Similarity NPC153578
0.8315 Intermediate Similarity NPC299149
0.8315 Intermediate Similarity NPC114257
0.8314 Intermediate Similarity NPC17432
0.8305 Intermediate Similarity NPC475233
0.8303 Intermediate Similarity NPC94781
0.8295 Intermediate Similarity NPC470335
0.8295 Intermediate Similarity NPC199357
0.8295 Intermediate Similarity NPC470336
0.8293 Intermediate Similarity NPC285122
0.8287 Intermediate Similarity NPC282636
0.8287 Intermediate Similarity NPC294863
0.8287 Intermediate Similarity NPC105591
0.8286 Intermediate Similarity NPC298778
0.8268 Intermediate Similarity NPC164047
0.8268 Intermediate Similarity NPC470448
0.8268 Intermediate Similarity NPC470452
0.8268 Intermediate Similarity NPC208069
0.8268 Intermediate Similarity NPC470453
0.8256 Intermediate Similarity NPC216752
0.8251 Intermediate Similarity NPC264302
0.8249 Intermediate Similarity NPC63105
0.8246 Intermediate Similarity NPC475449
0.8239 Intermediate Similarity NPC473113
0.8235 Intermediate Similarity NPC29552
0.8232 Intermediate Similarity NPC33083
0.8232 Intermediate Similarity NPC475923
0.8229 Intermediate Similarity NPC222455
0.8225 Intermediate Similarity NPC477736
0.8222 Intermediate Similarity NPC473717
0.8222 Intermediate Similarity NPC475662
0.8222 Intermediate Similarity NPC473631
0.8222 Intermediate Similarity NPC293227
0.8218 Intermediate Similarity NPC469419
0.8216 Intermediate Similarity NPC42286
0.8212 Intermediate Similarity NPC245059
0.8212 Intermediate Similarity NPC84494
0.8192 Intermediate Similarity NPC131862
0.8192 Intermediate Similarity NPC470438
0.8192 Intermediate Similarity NPC213052
0.8192 Intermediate Similarity NPC98776
0.8187 Intermediate Similarity NPC314795
0.8187 Intermediate Similarity NPC326084
0.8182 Intermediate Similarity NPC280385
0.8177 Intermediate Similarity NPC249560
0.8177 Intermediate Similarity NPC275977
0.8177 Intermediate Similarity NPC106700
0.8177 Intermediate Similarity NPC75574
0.8177 Intermediate Similarity NPC223860
0.8172 Intermediate Similarity NPC313274
0.8166 Intermediate Similarity NPC182921
0.8166 Intermediate Similarity NPC477735
0.8166 Intermediate Similarity NPC474824
0.8166 Intermediate Similarity NPC218870
0.8166 Intermediate Similarity NPC470408
0.8161 Intermediate Similarity NPC102465
0.8161 Intermediate Similarity NPC280923
0.8156 Intermediate Similarity NPC477683
0.8156 Intermediate Similarity NPC477682
0.8146 Intermediate Similarity NPC474345
0.8144 Intermediate Similarity NPC247219
0.814 Intermediate Similarity NPC284495
0.814 Intermediate Similarity NPC328093
0.8136 Intermediate Similarity NPC137871
0.8136 Intermediate Similarity NPC257011
0.8136 Intermediate Similarity NPC470715
0.8136 Intermediate Similarity NPC474522
0.8136 Intermediate Similarity NPC9002
0.8136 Intermediate Similarity NPC470714
0.8136 Intermediate Similarity NPC470716
0.8136 Intermediate Similarity NPC288152
0.8133 Intermediate Similarity NPC119767
0.8132 Intermediate Similarity NPC295625
0.8132 Intermediate Similarity NPC473554
0.8132 Intermediate Similarity NPC470719
0.8129 Intermediate Similarity NPC317580

  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 NPC65118 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
0.8914 High Similarity NPD7879 Clinical (unspecified phase)
0.8587 High Similarity NPD8320 Phase 1
0.8587 High Similarity NPD8319 Approved
0.8514 High Similarity NPD8313 Approved
0.8514 High Similarity NPD8312 Approved
0.8462 Intermediate Similarity NPD7699 Phase 2
0.8462 Intermediate Similarity NPD7700 Phase 2
0.8371 Intermediate Similarity NPD8150 Discontinued
0.8333 Intermediate Similarity NPD7435 Discontinued
0.8297 Intermediate Similarity NPD6534 Approved
0.8297 Intermediate Similarity NPD6535 Approved
0.8235 Intermediate Similarity NPD7698 Approved
0.8235 Intermediate Similarity NPD7697 Approved
0.8235 Intermediate Similarity NPD7696 Phase 3
0.8168 Intermediate Similarity NPD7874 Approved
0.8168 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD7871 Phase 2
0.8095 Intermediate Similarity NPD7870 Phase 2
0.8075 Intermediate Similarity NPD6781 Approved
0.8075 Intermediate Similarity NPD6776 Approved
0.8075 Intermediate Similarity NPD6778 Approved
0.8075 Intermediate Similarity NPD6782 Approved
0.8075 Intermediate Similarity NPD6780 Approved
0.8075 Intermediate Similarity NPD6779 Approved
0.8075 Intermediate Similarity NPD6777 Approved
0.8063 Intermediate Similarity NPD7701 Phase 2
0.7946 Intermediate Similarity NPD6213 Phase 3
0.7946 Intermediate Similarity NPD6212 Phase 3
0.7946 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7944 Intermediate Similarity NPD7808 Phase 3
0.7927 Intermediate Similarity NPD8151 Discontinued
0.7889 Intermediate Similarity NPD7251 Discontinued
0.788 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7865 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7846 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7846 Intermediate Similarity NPD7783 Phase 2
0.7846 Intermediate Similarity NPD7801 Approved
0.7833 Intermediate Similarity NPD6797 Phase 2
0.7816 Intermediate Similarity NPD7075 Discontinued
0.7809 Intermediate Similarity NPD7473 Discontinued
0.7778 Intermediate Similarity NPD7074 Phase 3
0.7761 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD7819 Suspended
0.774 Intermediate Similarity NPD6232 Discontinued
0.7719 Intermediate Similarity NPD3226 Approved
0.7684 Intermediate Similarity NPD6959 Discontinued
0.768 Intermediate Similarity NPD7472 Approved
0.765 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD7054 Approved
0.7622 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7617 Intermediate Similarity NPD6823 Phase 2
0.7614 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7596 Intermediate Similarity NPD6559 Discontinued
0.7569 Intermediate Similarity NPD3751 Discontinued
0.7569 Intermediate Similarity NPD7799 Discontinued
0.7514 Intermediate Similarity NPD7458 Discontinued
0.7485 Intermediate Similarity NPD2346 Discontinued
0.7471 Intermediate Similarity NPD4380 Phase 2
0.7459 Intermediate Similarity NPD6166 Phase 2
0.7459 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7446 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD8455 Phase 2
0.7432 Intermediate Similarity NPD5844 Phase 1
0.7425 Intermediate Similarity NPD5404 Approved
0.7425 Intermediate Similarity NPD5406 Approved
0.7425 Intermediate Similarity NPD5408 Approved
0.7425 Intermediate Similarity NPD5405 Approved
0.7401 Intermediate Similarity NPD5402 Approved
0.7401 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6801 Discontinued
0.7384 Intermediate Similarity NPD2534 Approved
0.7384 Intermediate Similarity NPD2533 Approved
0.7384 Intermediate Similarity NPD2532 Approved
0.7377 Intermediate Similarity NPD3818 Discontinued
0.7377 Intermediate Similarity NPD7228 Approved
0.7371 Intermediate Similarity NPD8285 Discontinued
0.7365 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD3787 Discontinued
0.733 Intermediate Similarity NPD7411 Suspended
0.7326 Intermediate Similarity NPD7390 Discontinued
0.7302 Intermediate Similarity NPD8434 Phase 2
0.7273 Intermediate Similarity NPD6599 Discontinued
0.7263 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD1470 Approved
0.7219 Intermediate Similarity NPD7685 Pre-registration
0.7216 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD6190 Approved
0.7207 Intermediate Similarity NPD3817 Phase 2
0.72 Intermediate Similarity NPD5403 Approved
0.7184 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7266 Discontinued
0.7167 Intermediate Similarity NPD7768 Phase 2
0.7156 Intermediate Similarity NPD8059 Phase 3
0.7156 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5494 Approved
0.7128 Intermediate Similarity NPD7240 Approved
0.7128 Intermediate Similarity NPD8368 Discontinued
0.7127 Intermediate Similarity NPD3749 Approved
0.7126 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6799 Approved
0.7118 Intermediate Similarity NPD2935 Discontinued
0.7095 Intermediate Similarity NPD1934 Approved
0.7095 Intermediate Similarity NPD37 Approved
0.7088 Intermediate Similarity NPD6234 Discontinued
0.7086 Intermediate Similarity NPD5401 Approved
0.7086 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD4967 Phase 2
0.7072 Intermediate Similarity NPD3882 Suspended
0.7072 Intermediate Similarity NPD4965 Approved
0.7072 Intermediate Similarity NPD4966 Approved
0.7052 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD8407 Phase 2
0.7006 Intermediate Similarity NPD3764 Approved
0.6994 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6989 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1201 Approved
0.6973 Remote Similarity NPD5710 Approved
0.6973 Remote Similarity NPD5711 Approved
0.6971 Remote Similarity NPD7236 Approved
0.6966 Remote Similarity NPD7239 Suspended
0.6961 Remote Similarity NPD1465 Phase 2
0.6959 Remote Similarity NPD8435 Approved
0.6959 Remote Similarity NPD8361 Approved
0.6959 Remote Similarity NPD8360 Approved
0.6957 Remote Similarity NPD7930 Approved
0.6954 Remote Similarity NPD4628 Phase 3
0.6936 Remote Similarity NPD1549 Phase 2
0.6936 Remote Similarity NPD970 Clinical (unspecified phase)
0.6935 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6919 Remote Similarity NPD8090 Clinical (unspecified phase)
0.691 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6905 Remote Similarity NPD2313 Discontinued
0.69 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6878 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6868 Remote Similarity NPD2801 Approved
0.686 Remote Similarity NPD1510 Phase 2
0.6857 Remote Similarity NPD7003 Approved
0.6857 Remote Similarity NPD8166 Discontinued
0.6857 Remote Similarity NPD3750 Approved
0.6857 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6856 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6842 Remote Similarity NPD1607 Approved
0.6836 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6825 Remote Similarity NPD7177 Discontinued
0.6821 Remote Similarity NPD1551 Phase 2
0.6811 Remote Similarity NPD5537 Clinical (unspecified phase)
0.678 Remote Similarity NPD7584 Approved
0.678 Remote Similarity NPD3300 Phase 2
0.6763 Remote Similarity NPD2799 Discontinued
0.6761 Remote Similarity NPD8366 Approved
0.676 Remote Similarity NPD1512 Approved
0.675 Remote Similarity NPD8485 Approved
0.6738 Remote Similarity NPD7199 Phase 2
0.6732 Remote Similarity NPD7999 Approved
0.6725 Remote Similarity NPD1240 Approved
0.6724 Remote Similarity NPD6100 Approved
0.6724 Remote Similarity NPD6099 Approved
0.6724 Remote Similarity NPD2796 Approved
0.672 Remote Similarity NPD919 Approved
0.6719 Remote Similarity NPD5953 Discontinued
0.6716 Remote Similarity NPD7680 Approved
0.6705 Remote Similarity NPD6674 Discontinued
0.6705 Remote Similarity NPD7097 Phase 1
0.6698 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6686 Remote Similarity NPD230 Phase 1
0.6686 Remote Similarity NPD1933 Approved
0.6686 Remote Similarity NPD6832 Phase 2
0.6683 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6667 Remote Similarity NPD651 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2798 Approved
0.6649 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6648 Remote Similarity NPD1511 Approved
0.6647 Remote Similarity NPD7008 Discontinued
0.6636 Remote Similarity NPD8491 Approved
0.6632 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6628 Remote Similarity NPD943 Approved
0.6628 Remote Similarity NPD4060 Phase 1
0.6615 Remote Similarity NPD7286 Phase 2
0.6611 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6609 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6605 Remote Similarity NPD9493 Approved
0.6591 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6591 Remote Similarity NPD1471 Phase 3
0.659 Remote Similarity NPD447 Suspended
0.6587 Remote Similarity NPD7585 Approved
0.6579 Remote Similarity NPD3926 Phase 2
0.6575 Remote Similarity NPD6273 Approved
0.6573 Remote Similarity NPD8404 Phase 2
0.6571 Remote Similarity NPD4308 Phase 3
0.6571 Remote Similarity NPD7033 Discontinued
0.6571 Remote Similarity NPD3748 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