Structure

Physi-Chem Properties

Molecular Weight:  938.39
Volume:  916.831
LogP:  5.122
LogD:  2.071
LogS:  -3.65
# Rotatable Bonds:  13
TPSA:  255.66
# H-Bond Aceptor:  18
# H-Bond Donor:  6
# Rings:  8
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.083
Synthetic Accessibility Score:  6.551
Fsp3:  0.612
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:  -5.731
MDCK Permeability:  5.251420952845365e-05
Pgp-inhibitor:  0.928
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.018
Plasma Protein Binding (PPB):  98.47586822509766%
Volume Distribution (VD):  0.106
Pgp-substrate:  7.167325973510742%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.983
CYP2C19-inhibitor:  0.047
CYP2C19-substrate:  0.375
CYP2C9-inhibitor:  0.128
CYP2C9-substrate:  0.736
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.149
CYP3A4-inhibitor:  0.09
CYP3A4-substrate:  0.306

ADMET: Excretion

Clearance (CL):  7.967
Half-life (T1/2):  0.49

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.488
Drug-inuced Liver Injury (DILI):  0.989
AMES Toxicity:  0.976
Rat Oral Acute Toxicity:  0.914
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.88
Carcinogencity:  0.951
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.045

Download Data

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

  Natural Product: NPC176246

Natural Product ID:  NPC176246
Common Name*:   Grincamycin B
IUPAC Name:   (3R)-4-[1,5-dihydroxy-6-[(2R,4R,5S,6R)-4-hydroxy-6-methyl-5-[(2S,5S,6S)-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]-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 B
Standard InCHIKey:  FMPNXDMJKBQLJR-SVDKGFTASA-N
Standard InCHI:  InChI=1S/C49H62O18/c1-22-31(50)11-15-38(60-22)64-34-13-17-40(62-24(34)3)66-48-26(5)59-36(19-33(48)52)28-9-10-30-43(45(28)56)47(58)29-8-7-27(44(55)42(29)46(30)57)20-49(6,21-37(53)54)67-41-18-14-35(25(4)63-41)65-39-16-12-32(51)23(2)61-39/h7-10,22-26,33-36,38-41,48,52,55-56H,11-21H2,1-6H3,(H,53,54)/t22-,23-,24-,25-,26+,33+,34-,35-,36+,38-,39-,40-,41-,48+,49+/m0/s1
SMILES:  C[C@H]1C(=O)CC[C@@H](O1)O[C@H]1CC[C@@H](O[C@H]1C)O[C@@H]1[C@@H](C)O[C@H](C[C@H]1O)c1ccc2c(c1O)C(=O)c1ccc(C[C@](C)(CC(=O)O)O[C@H]3CC[C@@H]([C@H](C)O3)O[C@H]3CCC(=O)[C@H](C)O3)c(c1C2=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2011810
PubChem CID:   57332649
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 = 2100.0 nM PMID[540226]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 8500.0 nM PMID[540226]
NPT1312 Cell Line SW1990 Homo sapiens IC50 = 11000.0 nM PMID[540226]
NPT165 Cell Line HeLa Homo sapiens IC50 = 6400.0 nM PMID[540226]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 > 100000.0 nM PMID[540226]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 12000.0 nM PMID[540226]

☑ 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 NPC176246 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 NPC65118
0.9816 High Similarity NPC183441
0.9641 High Similarity NPC72783
0.9408 High Similarity NPC187441
0.9408 High Similarity NPC283980
0.9345 High Similarity NPC70862
0.9235 High Similarity NPC115447
0.9235 High Similarity NPC470582
0.9235 High Similarity NPC83331
0.9235 High Similarity NPC470581
0.9222 High Similarity NPC175477
0.9157 High Similarity NPC478026
0.9123 High Similarity NPC266513
0.9118 High Similarity NPC470583
0.9118 High Similarity NPC19056
0.9112 High Similarity NPC270027
0.9053 High Similarity NPC478021
0.9042 High Similarity NPC478022
0.9042 High Similarity NPC478020
0.9024 High Similarity NPC206641
0.9024 High Similarity NPC208651
0.9017 High Similarity NPC197357
0.9017 High Similarity NPC85316
0.9 High Similarity NPC294501
0.9 High Similarity NPC131405
0.897 High Similarity NPC53139
0.8941 High Similarity NPC470580
0.8939 High Similarity NPC470194
0.8939 High Similarity NPC470195
0.8939 High Similarity NPC470196
0.8939 High Similarity NPC470200
0.8939 High Similarity NPC470193
0.8939 High Similarity NPC316274
0.8939 High Similarity NPC470197
0.8939 High Similarity NPC470198
0.8939 High Similarity NPC282474
0.8922 High Similarity NPC187934
0.8922 High Similarity NPC97637
0.8914 High Similarity NPC292706
0.8914 High Similarity NPC224557
0.8902 High Similarity NPC3449
0.8895 High Similarity NPC223735
0.8895 High Similarity NPC307754
0.8848 High Similarity NPC148323
0.8848 High Similarity NPC283480
0.8844 High Similarity NPC289876
0.8827 High Similarity NPC470199
0.8827 High Similarity NPC314459
0.882 High Similarity NPC314672
0.88 High Similarity NPC477860
0.88 High Similarity NPC475161
0.8788 High Similarity NPC174599
0.8788 High Similarity NPC82190
0.8788 High Similarity NPC192219
0.8786 High Similarity NPC186800
0.8786 High Similarity NPC470667
0.8743 High Similarity NPC58538
0.8736 High Similarity NPC314489
0.8736 High Similarity NPC232818
0.8736 High Similarity NPC198893
0.8729 High Similarity NPC314687
0.8728 High Similarity NPC203751
0.8727 High Similarity NPC205172
0.8727 High Similarity NPC209393
0.8706 High Similarity NPC178281
0.8706 High Similarity NPC329647
0.8706 High Similarity NPC470735
0.8696 High Similarity NPC314941
0.8671 High Similarity NPC13989
0.8667 High Similarity NPC48474
0.8659 High Similarity NPC475407
0.8656 High Similarity NPC315889
0.8652 High Similarity NPC241847
0.8652 High Similarity NPC87583
0.8644 High Similarity NPC313452
0.8629 High Similarity NPC66820
0.8629 High Similarity NPC170018
0.8629 High Similarity NPC92403
0.8629 High Similarity NPC475246
0.8629 High Similarity NPC46958
0.8629 High Similarity NPC102053
0.8629 High Similarity NPC76112
0.8623 High Similarity NPC478027
0.8621 High Similarity NPC85368
0.8614 High Similarity NPC474621
0.8614 High Similarity NPC474622
0.8605 High Similarity NPC63470
0.8588 High Similarity NPC101116
0.8588 High Similarity NPC278329
0.8588 High Similarity NPC212099
0.8588 High Similarity NPC315221
0.8588 High Similarity NPC146837
0.8579 High Similarity NPC133775
0.8571 High Similarity NPC68381
0.8571 High Similarity NPC3718
0.8563 High Similarity NPC315619
0.8556 High Similarity NPC205721
0.8514 High Similarity NPC472054
0.8488 Intermediate Similarity NPC99216
0.8478 Intermediate Similarity NPC108487
0.8462 Intermediate Similarity NPC257309
0.8457 Intermediate Similarity NPC30432
0.8457 Intermediate Similarity NPC111536
0.8457 Intermediate Similarity NPC271385
0.8457 Intermediate Similarity NPC5029
0.8457 Intermediate Similarity NPC76128
0.8448 Intermediate Similarity NPC246274
0.8444 Intermediate Similarity NPC229817
0.8444 Intermediate Similarity NPC221140
0.8444 Intermediate Similarity NPC475352
0.8444 Intermediate Similarity NPC473686
0.8444 Intermediate Similarity NPC475220
0.8443 Intermediate Similarity NPC474533
0.8443 Intermediate Similarity NPC474534
0.8439 Intermediate Similarity NPC477469
0.8439 Intermediate Similarity NPC477466
0.8439 Intermediate Similarity NPC477473
0.8439 Intermediate Similarity NPC477471
0.843 Intermediate Similarity NPC17432
0.8427 Intermediate Similarity NPC153578
0.8427 Intermediate Similarity NPC114257
0.8427 Intermediate Similarity NPC299149
0.8427 Intermediate Similarity NPC277710
0.8418 Intermediate Similarity NPC475233
0.8415 Intermediate Similarity NPC285122
0.8409 Intermediate Similarity NPC199357
0.84 Intermediate Similarity NPC298778
0.8398 Intermediate Similarity NPC282636
0.8398 Intermediate Similarity NPC105591
0.8398 Intermediate Similarity NPC294863
0.8391 Intermediate Similarity NPC471295
0.838 Intermediate Similarity NPC470452
0.838 Intermediate Similarity NPC208069
0.838 Intermediate Similarity NPC470453
0.838 Intermediate Similarity NPC470448
0.838 Intermediate Similarity NPC164047
0.8373 Intermediate Similarity NPC44378
0.8373 Intermediate Similarity NPC280753
0.8372 Intermediate Similarity NPC216752
0.8362 Intermediate Similarity NPC63105
0.8361 Intermediate Similarity NPC264302
0.8353 Intermediate Similarity NPC29552
0.8343 Intermediate Similarity NPC222455
0.8343 Intermediate Similarity NPC33083
0.8343 Intermediate Similarity NPC477736
0.8333 Intermediate Similarity NPC293227
0.8333 Intermediate Similarity NPC475662
0.8333 Intermediate Similarity NPC469419
0.8333 Intermediate Similarity NPC473717
0.8333 Intermediate Similarity NPC473631
0.8324 Intermediate Similarity NPC84494
0.8324 Intermediate Similarity NPC245059
0.8324 Intermediate Similarity NPC42286
0.8313 Intermediate Similarity NPC94781
0.8305 Intermediate Similarity NPC470438
0.8305 Intermediate Similarity NPC98776
0.8305 Intermediate Similarity NPC213052
0.8304 Intermediate Similarity NPC314795
0.8295 Intermediate Similarity NPC280385
0.8287 Intermediate Similarity NPC275977
0.8287 Intermediate Similarity NPC223860
0.8287 Intermediate Similarity NPC75574
0.8287 Intermediate Similarity NPC106700
0.8287 Intermediate Similarity NPC249560
0.8284 Intermediate Similarity NPC477735
0.828 Intermediate Similarity NPC313274
0.8276 Intermediate Similarity NPC102465
0.8276 Intermediate Similarity NPC280923
0.8268 Intermediate Similarity NPC477683
0.8268 Intermediate Similarity NPC477682
0.8263 Intermediate Similarity NPC120171
0.8258 Intermediate Similarity NPC474345
0.8256 Intermediate Similarity NPC328093
0.8249 Intermediate Similarity NPC470716
0.8249 Intermediate Similarity NPC288152
0.8249 Intermediate Similarity NPC257011
0.8249 Intermediate Similarity NPC137871
0.8249 Intermediate Similarity NPC470714
0.8249 Intermediate Similarity NPC470715
0.8249 Intermediate Similarity NPC473113
0.8249 Intermediate Similarity NPC474522
0.8249 Intermediate Similarity NPC9002
0.8242 Intermediate Similarity NPC474630
0.8242 Intermediate Similarity NPC470719
0.8242 Intermediate Similarity NPC295625
0.8242 Intermediate Similarity NPC473554
0.8242 Intermediate Similarity NPC170055
0.8239 Intermediate Similarity NPC5319
0.8235 Intermediate Similarity NPC266469
0.8232 Intermediate Similarity NPC162394
0.8232 Intermediate Similarity NPC156785
0.8232 Intermediate Similarity NPC241781
0.8229 Intermediate Similarity NPC475174
0.8222 Intermediate Similarity NPC198902
0.8222 Intermediate Similarity NPC212290
0.8212 Intermediate Similarity NPC231787
0.8208 Intermediate Similarity NPC317544
0.8208 Intermediate Similarity NPC69868
0.8202 Intermediate Similarity NPC154986
0.8202 Intermediate Similarity NPC124828

  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 NPC176246 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
0.9029 High Similarity NPD7879 Clinical (unspecified phase)
0.8696 High Similarity NPD8320 Phase 1
0.8696 High Similarity NPD8319 Approved
0.8629 High Similarity NPD8312 Approved
0.8629 High Similarity NPD8313 Approved
0.8571 High Similarity NPD7700 Phase 2
0.8571 High Similarity NPD7699 Phase 2
0.8483 Intermediate Similarity NPD8150 Discontinued
0.8441 Intermediate Similarity NPD7435 Discontinued
0.8407 Intermediate Similarity NPD6534 Approved
0.8407 Intermediate Similarity NPD6535 Approved
0.8272 Intermediate Similarity NPD7874 Approved
0.8272 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.8245 Intermediate Similarity NPD7697 Approved
0.8245 Intermediate Similarity NPD7698 Approved
0.8245 Intermediate Similarity NPD7696 Phase 3
0.8239 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD6781 Approved
0.8182 Intermediate Similarity NPD6782 Approved
0.8182 Intermediate Similarity NPD6778 Approved
0.8182 Intermediate Similarity NPD6776 Approved
0.8182 Intermediate Similarity NPD6777 Approved
0.8182 Intermediate Similarity NPD6780 Approved
0.8182 Intermediate Similarity NPD6779 Approved
0.8168 Intermediate Similarity NPD7701 Phase 2
0.8105 Intermediate Similarity NPD7871 Phase 2
0.8105 Intermediate Similarity NPD7870 Phase 2
0.8056 Intermediate Similarity NPD7808 Phase 3
0.8054 Intermediate Similarity NPD6213 Phase 3
0.8054 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.8054 Intermediate Similarity NPD6212 Phase 3
0.8031 Intermediate Similarity NPD8151 Discontinued
0.8 Intermediate Similarity NPD7251 Discontinued
0.7949 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD7801 Approved
0.7949 Intermediate Similarity NPD7783 Phase 2
0.7944 Intermediate Similarity NPD6797 Phase 2
0.7892 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7889 Intermediate Similarity NPD7074 Phase 3
0.7861 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD7075 Discontinued
0.779 Intermediate Similarity NPD7472 Approved
0.7784 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD7054 Approved
0.7727 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD7473 Discontinued
0.772 Intermediate Similarity NPD6823 Phase 2
0.7705 Intermediate Similarity NPD6559 Discontinued
0.768 Intermediate Similarity NPD3751 Discontinued
0.7657 Intermediate Similarity NPD7819 Suspended
0.7657 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD6232 Discontinued
0.7634 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD3226 Approved
0.7598 Intermediate Similarity NPD6959 Discontinued
0.7586 Intermediate Similarity NPD4380 Phase 2
0.7582 Intermediate Similarity NPD7799 Discontinued
0.7569 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD6166 Phase 2
0.7557 Intermediate Similarity NPD8455 Phase 2
0.7554 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD5402 Approved
0.75 Intermediate Similarity NPD6801 Discontinued
0.7486 Intermediate Similarity NPD3818 Discontinued
0.7486 Intermediate Similarity NPD7228 Approved
0.7459 Intermediate Similarity NPD3787 Discontinued
0.7446 Intermediate Similarity NPD5844 Phase 1
0.7429 Intermediate Similarity NPD7458 Discontinued
0.7407 Intermediate Similarity NPD8434 Phase 2
0.7396 Intermediate Similarity NPD2346 Discontinued
0.7337 Intermediate Similarity NPD5405 Approved
0.7337 Intermediate Similarity NPD5406 Approved
0.7337 Intermediate Similarity NPD5408 Approved
0.7337 Intermediate Similarity NPD5404 Approved
0.7326 Intermediate Similarity NPD6190 Approved
0.7326 Intermediate Similarity NPD7685 Pre-registration
0.7318 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD5403 Approved
0.7299 Intermediate Similarity NPD2533 Approved
0.7299 Intermediate Similarity NPD2534 Approved
0.7299 Intermediate Similarity NPD2532 Approved
0.7296 Intermediate Similarity NPD8285 Discontinued
0.7294 Intermediate Similarity NPD7266 Discontinued
0.7288 Intermediate Similarity NPD6599 Discontinued
0.7283 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD8059 Phase 3
0.7247 Intermediate Similarity NPD7411 Suspended
0.7246 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7390 Discontinued
0.7234 Intermediate Similarity NPD8368 Discontinued
0.7234 Intermediate Similarity NPD7240 Approved
0.7232 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD3817 Phase 2
0.72 Intermediate Similarity NPD5401 Approved
0.7143 Intermediate Similarity NPD6799 Approved
0.7134 Intermediate Similarity NPD1470 Approved
0.712 Intermediate Similarity NPD8407 Phase 2
0.7111 Intermediate Similarity NPD37 Approved
0.7111 Intermediate Similarity NPD1934 Approved
0.7104 Intermediate Similarity NPD6234 Discontinued
0.7102 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD3882 Suspended
0.7088 Intermediate Similarity NPD4967 Phase 2
0.7088 Intermediate Similarity NPD4965 Approved
0.7088 Intermediate Similarity NPD4966 Approved
0.7088 Intermediate Similarity NPD7768 Phase 2
0.7069 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD4628 Phase 3
0.7066 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD5494 Approved
0.7062 Intermediate Similarity NPD8360 Approved
0.7062 Intermediate Similarity NPD8361 Approved
0.7062 Intermediate Similarity NPD8435 Approved
0.7053 Intermediate Similarity NPD7930 Approved
0.7049 Intermediate Similarity NPD3749 Approved
0.7035 Intermediate Similarity NPD2935 Discontinued
0.702 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.6989 Remote Similarity NPD7236 Approved
0.6984 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7239 Suspended
0.6978 Remote Similarity NPD1465 Phase 2
0.6959 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6952 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3764 Approved
0.6914 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6898 Remote Similarity NPD5711 Approved
0.6898 Remote Similarity NPD5710 Approved
0.689 Remote Similarity NPD1201 Approved
0.6885 Remote Similarity NPD2801 Approved
0.6878 Remote Similarity NPD7584 Approved
0.6875 Remote Similarity NPD8166 Discontinued
0.6857 Remote Similarity NPD1549 Phase 2
0.6857 Remote Similarity NPD970 Clinical (unspecified phase)
0.685 Remote Similarity NPD8485 Approved
0.6845 Remote Similarity NPD7199 Phase 2
0.6833 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7999 Approved
0.6824 Remote Similarity NPD2313 Discontinued
0.6818 Remote Similarity NPD6674 Discontinued
0.6814 Remote Similarity NPD7680 Approved
0.68 Remote Similarity NPD1552 Clinical (unspecified phase)
0.68 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6798 Remote Similarity NPD3300 Phase 2
0.6791 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6782 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6782 Remote Similarity NPD1510 Phase 2
0.678 Remote Similarity NPD6398 Clinical (unspecified phase)
0.678 Remote Similarity NPD7003 Approved
0.678 Remote Similarity NPD3750 Approved
0.6778 Remote Similarity NPD1512 Approved
0.6776 Remote Similarity NPD8366 Approved
0.6763 Remote Similarity NPD1607 Approved
0.676 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6754 Remote Similarity NPD7177 Discontinued
0.6743 Remote Similarity NPD1551 Phase 2
0.6738 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6722 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6705 Remote Similarity NPD230 Phase 1
0.6686 Remote Similarity NPD651 Clinical (unspecified phase)
0.6686 Remote Similarity NPD2799 Discontinued
0.6683 Remote Similarity NPD7585 Approved
0.6667 Remote Similarity NPD8404 Phase 2
0.6667 Remote Similarity NPD1511 Approved
0.6667 Remote Similarity NPD5125 Phase 3
0.6667 Remote Similarity NPD5126 Approved
0.6651 Remote Similarity NPD8491 Approved
0.6649 Remote Similarity NPD919 Approved
0.6649 Remote Similarity NPD5953 Discontinued
0.6648 Remote Similarity NPD6100 Approved
0.6648 Remote Similarity NPD2796 Approved
0.6648 Remote Similarity NPD6099 Approved
0.6647 Remote Similarity NPD1240 Approved
0.6647 Remote Similarity NPD943 Approved
0.6647 Remote Similarity NPD4060 Phase 1
0.6635 Remote Similarity NPD7583 Approved
0.6629 Remote Similarity NPD7097 Phase 1
0.661 Remote Similarity NPD5762 Approved
0.661 Remote Similarity NPD5763 Approved
0.6609 Remote Similarity NPD1933 Approved
0.6608 Remote Similarity NPD6832 Phase 2
0.6593 Remote Similarity NPD6273 Approved
0.6591 Remote Similarity NPD7033 Discontinued
0.6588 Remote Similarity NPD2798 Approved
0.6582 Remote Similarity NPD4955 Approved
0.6582 Remote Similarity NPD5028 Approved
0.6582 Remote Similarity NPD36 Approved
0.6582 Remote Similarity NPD4954 Approved
0.6582 Remote Similarity NPD5034 Approved
0.6582 Remote Similarity NPD5026 Approved
0.658 Remote Similarity NPD7893 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