Structure

Physi-Chem Properties

Molecular Weight:  510.25
Volume:  495.463
LogP:  2.157
LogD:  1.936
LogS:  -4.38
# Rotatable Bonds:  8
TPSA:  130.12
# H-Bond Aceptor:  10
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.333
Synthetic Accessibility Score:  5.812
Fsp3:  0.885
Lipinski Rule-of-5:  Accepted
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:  -5.277
MDCK Permeability:  0.0001128980511566624
Pgp-inhibitor:  0.371
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.028
30% Bioavailability (F30%):  0.405

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.169
Plasma Protein Binding (PPB):  30.814029693603516%
Volume Distribution (VD):  1.076
Pgp-substrate:  51.12897872924805%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.061
CYP2C19-inhibitor:  0.011
CYP2C19-substrate:  0.506
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.013
CYP2D6-inhibitor:  0.052
CYP2D6-substrate:  0.105
CYP3A4-inhibitor:  0.434
CYP3A4-substrate:  0.511

ADMET: Excretion

Clearance (CL):  2.951
Half-life (T1/2):  0.862

ADMET: Toxicity

hERG Blockers:  0.274
Human Hepatotoxicity (H-HT):  0.323
Drug-inuced Liver Injury (DILI):  0.816
AMES Toxicity:  0.849
Rat Oral Acute Toxicity:  0.117
Maximum Recommended Daily Dose:  0.794
Skin Sensitization:  0.544
Carcinogencity:  0.219
Eye Corrosion:  0.005
Eye Irritation:  0.069
Respiratory Toxicity:  0.925

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

  Natural Product: NPC470872

Natural Product ID:  NPC470872
Common Name*:   15-Hydroxyepicaryoptin
IUPAC Name:   [(3S,4R,4aR,5S,7R,8S,8aR)-8-[(2S,3aS,6aR)-5-hydroxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-3,5-diacetyloxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
Synonyms:  
Standard InCHIKey:  CVAFGEMJUHEQAJ-AYSSTIIESA-N
Standard InCHI:  InChI=1S/C26H38O10/c1-13-8-21(34-16(4)29)25(11-31-14(2)27)18(6-7-19(33-15(3)28)26(25)12-32-26)24(13,5)20-9-17-10-22(30)36-23(17)35-20/h13,17-23,30H,6-12H2,1-5H3/t13-,17+,18-,19+,20+,21+,22?,23-,24+,25+,26-/m1/s1
SMILES:  CC1CC(C2(C(C1(C)C3CC4CC(OC4O3)O)CCC(C25CO5)OC(=O)C)COC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2272662
PubChem CID:   76323467
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO33100 clerodendron sp. Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[12617583]

☑ 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
NPT1175 Organism Spodoptera litura Spodoptera litura TIME = 177.6 hr PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura TIME = 168.0 hr PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura TIME = 192.0 hr PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura TIME = 180.0 hr PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 7.2 % PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 9.6 % PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 70.4 % PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 62.4 % PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura mortality = 22.5 % PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura mortality = 27.6 % PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 272.2 mg PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 258.8 mg PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura TIME = 259.2 hr PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura TIME = 278.4 hr PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura mortality = 20.0 % PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura mortality = 32.0 % PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura TIME = 324.0 hr PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura TIME = 340.8 hr PMID[534481]
NPT1194 Organism Earias vitella Earias vitella TIME = 163.2 hr PMID[534481]
NPT1194 Organism Earias vitella Earias vitella TIME = 158.4 hr PMID[534481]
NPT1194 Organism Earias vitella Earias vitella TIME = 148.8 hr PMID[534481]
NPT1194 Organism Earias vitella Earias vitella Activity = 4.0 % PMID[534481]
NPT1194 Organism Earias vitella Earias vitella Activity = 68.0 % PMID[534481]
NPT1194 Organism Earias vitella Earias vitella Activity = 62.0 % PMID[534481]
NPT1194 Organism Earias vitella Earias vitella mortality = 28.0 % PMID[534481]
NPT1194 Organism Earias vitella Earias vitella mortality = 34.0 % PMID[534481]
NPT1194 Organism Earias vitella Earias vitella Activity = 58.0 mg PMID[534481]
NPT1194 Organism Earias vitella Earias vitella Activity = 57.2 mg PMID[534481]
NPT1194 Organism Earias vitella Earias vitella TIME = 216.0 hr PMID[534481]
NPT1194 Organism Earias vitella Earias vitella TIME = 230.4 hr PMID[534481]
NPT1194 Organism Earias vitella Earias vitella mortality = 8.0 % PMID[534481]
NPT1194 Organism Earias vitella Earias vitella TIME = 235.2 hr PMID[534481]
NPT1194 Organism Earias vitella Earias vitella TIME = 244.8 hr PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 74.0 % PMID[534481]
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 78.0 % PMID[534481]
NPT1194 Organism Earias vitella Earias vitella Activity = 62.15 % PMID[534481]
NPT1194 Organism Earias vitella Earias vitella Activity = 71.84 % PMID[534481]

☑ 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 NPC470872 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
0.9634 High Similarity NPC235402
0.9535 High Similarity NPC475307
0.9286 High Similarity NPC474008
0.9277 High Similarity NPC18953
0.9176 High Similarity NPC62202
0.9176 High Similarity NPC110365
0.9176 High Similarity NPC213658
0.9176 High Similarity NPC45833
0.9024 High Similarity NPC471217
0.9024 High Similarity NPC471216
0.8916 High Similarity NPC71541
0.8837 High Similarity NPC471411
0.8837 High Similarity NPC471410
0.8795 High Similarity NPC472951
0.8795 High Similarity NPC472943
0.8602 High Similarity NPC292775
0.8588 High Similarity NPC477447
0.8588 High Similarity NPC477446
0.8588 High Similarity NPC470155
0.8587 High Similarity NPC475765
0.8571 High Similarity NPC186588
0.8537 High Similarity NPC107963
0.8488 Intermediate Similarity NPC213737
0.8488 Intermediate Similarity NPC474346
0.8488 Intermediate Similarity NPC475820
0.8488 Intermediate Similarity NPC474253
0.8488 Intermediate Similarity NPC474284
0.8478 Intermediate Similarity NPC21897
0.8471 Intermediate Similarity NPC470156
0.8471 Intermediate Similarity NPC470154
0.8462 Intermediate Similarity NPC182740
0.8462 Intermediate Similarity NPC211845
0.8462 Intermediate Similarity NPC256104
0.8462 Intermediate Similarity NPC122083
0.8409 Intermediate Similarity NPC268633
0.8387 Intermediate Similarity NPC237071
0.8387 Intermediate Similarity NPC203434
0.8387 Intermediate Similarity NPC238796
0.8387 Intermediate Similarity NPC252056
0.8387 Intermediate Similarity NPC475785
0.8372 Intermediate Similarity NPC208912
0.8372 Intermediate Similarity NPC2096
0.837 Intermediate Similarity NPC151214
0.837 Intermediate Similarity NPC191915
0.8316 Intermediate Similarity NPC470030
0.8298 Intermediate Similarity NPC266417
0.828 Intermediate Similarity NPC94582
0.828 Intermediate Similarity NPC57964
0.8276 Intermediate Similarity NPC241959
0.8247 Intermediate Similarity NPC139181
0.8247 Intermediate Similarity NPC476837
0.8247 Intermediate Similarity NPC97260
0.8229 Intermediate Similarity NPC108227
0.8229 Intermediate Similarity NPC476512
0.8229 Intermediate Similarity NPC472081
0.8222 Intermediate Similarity NPC221993
0.8202 Intermediate Similarity NPC107603
0.8193 Intermediate Similarity NPC472952
0.8193 Intermediate Similarity NPC472950
0.8161 Intermediate Similarity NPC216800
0.8152 Intermediate Similarity NPC59006
0.8152 Intermediate Similarity NPC475878
0.8144 Intermediate Similarity NPC310138
0.8144 Intermediate Similarity NPC134967
0.8144 Intermediate Similarity NPC114700
0.8144 Intermediate Similarity NPC470029
0.814 Intermediate Similarity NPC186594
0.8132 Intermediate Similarity NPC20822
0.8132 Intermediate Similarity NPC82955
0.8125 Intermediate Similarity NPC51579
0.8118 Intermediate Similarity NPC177343
0.8118 Intermediate Similarity NPC272841
0.8105 Intermediate Similarity NPC113976
0.8105 Intermediate Similarity NPC198549
0.8043 Intermediate Similarity NPC470114
0.8041 Intermediate Similarity NPC475574
0.8022 Intermediate Similarity NPC471221
0.8022 Intermediate Similarity NPC476435
0.8022 Intermediate Similarity NPC128475
0.8021 Intermediate Similarity NPC209798
0.8021 Intermediate Similarity NPC471375
0.8021 Intermediate Similarity NPC471374
0.802 Intermediate Similarity NPC305939
0.8 Intermediate Similarity NPC145553
0.8 Intermediate Similarity NPC477283
0.8 Intermediate Similarity NPC155531
0.8 Intermediate Similarity NPC215968
0.8 Intermediate Similarity NPC156377
0.7979 Intermediate Similarity NPC30687
0.7979 Intermediate Similarity NPC477224
0.7979 Intermediate Similarity NPC113500
0.7979 Intermediate Similarity NPC175
0.7979 Intermediate Similarity NPC3538
0.7957 Intermediate Similarity NPC149966
0.7957 Intermediate Similarity NPC473066
0.7957 Intermediate Similarity NPC210759
0.7957 Intermediate Similarity NPC5632
0.7957 Intermediate Similarity NPC229801
0.7957 Intermediate Similarity NPC307167
0.7941 Intermediate Similarity NPC86217
0.7938 Intermediate Similarity NPC471428
0.7938 Intermediate Similarity NPC471426
0.7938 Intermediate Similarity NPC471427
0.7931 Intermediate Similarity NPC475456
0.7912 Intermediate Similarity NPC472396
0.7912 Intermediate Similarity NPC140446
0.7912 Intermediate Similarity NPC43912
0.7912 Intermediate Similarity NPC161928
0.7912 Intermediate Similarity NPC210658
0.7912 Intermediate Similarity NPC5943
0.7907 Intermediate Similarity NPC43463
0.7895 Intermediate Similarity NPC473067
0.7895 Intermediate Similarity NPC473064
0.7895 Intermediate Similarity NPC473065
0.7889 Intermediate Similarity NPC290612
0.7882 Intermediate Similarity NPC136424
0.7872 Intermediate Similarity NPC167644
0.7872 Intermediate Similarity NPC35164
0.7872 Intermediate Similarity NPC311246
0.7865 Intermediate Similarity NPC477285
0.7865 Intermediate Similarity NPC111582
0.7857 Intermediate Similarity NPC166250
0.7857 Intermediate Similarity NPC476838
0.7857 Intermediate Similarity NPC476839
0.7857 Intermediate Similarity NPC308489
0.7849 Intermediate Similarity NPC473542
0.7841 Intermediate Similarity NPC211049
0.7826 Intermediate Similarity NPC476379
0.7812 Intermediate Similarity NPC476510
0.7812 Intermediate Similarity NPC142264
0.7812 Intermediate Similarity NPC296936
0.7802 Intermediate Similarity NPC131365
0.7789 Intermediate Similarity NPC305418
0.7789 Intermediate Similarity NPC45959
0.7789 Intermediate Similarity NPC252253
0.7778 Intermediate Similarity NPC474156
0.7766 Intermediate Similarity NPC293609
0.7753 Intermediate Similarity NPC154043
0.7753 Intermediate Similarity NPC286719
0.7753 Intermediate Similarity NPC202688
0.7753 Intermediate Similarity NPC470611
0.7753 Intermediate Similarity NPC477286
0.7753 Intermediate Similarity NPC60018
0.7753 Intermediate Similarity NPC477284
0.7742 Intermediate Similarity NPC473472
0.7742 Intermediate Similarity NPC131466
0.7732 Intermediate Similarity NPC477223
0.7732 Intermediate Similarity NPC470028
0.7732 Intermediate Similarity NPC470591
0.7732 Intermediate Similarity NPC472273
0.7732 Intermediate Similarity NPC477222
0.7732 Intermediate Similarity NPC233649
0.7723 Intermediate Similarity NPC166079
0.7723 Intermediate Similarity NPC306776
0.7701 Intermediate Similarity NPC191345
0.7701 Intermediate Similarity NPC252483
0.7692 Intermediate Similarity NPC478111
0.7692 Intermediate Similarity NPC266651
0.7684 Intermediate Similarity NPC18724
0.7684 Intermediate Similarity NPC470623
0.7684 Intermediate Similarity NPC323231
0.7684 Intermediate Similarity NPC88962
0.7684 Intermediate Similarity NPC171741
0.7684 Intermediate Similarity NPC224003
0.7684 Intermediate Similarity NPC12297
0.7684 Intermediate Similarity NPC144790
0.7684 Intermediate Similarity NPC149400
0.7684 Intermediate Similarity NPC277774
0.7677 Intermediate Similarity NPC477225
0.7667 Intermediate Similarity NPC470070
0.766 Intermediate Similarity NPC279329
0.766 Intermediate Similarity NPC223143
0.766 Intermediate Similarity NPC18536
0.766 Intermediate Similarity NPC50443
0.7653 Intermediate Similarity NPC473638
0.7653 Intermediate Similarity NPC472144
0.7647 Intermediate Similarity NPC470151
0.764 Intermediate Similarity NPC116320
0.764 Intermediate Similarity NPC119922
0.764 Intermediate Similarity NPC190940
0.7634 Intermediate Similarity NPC281004
0.7634 Intermediate Similarity NPC201607
0.7634 Intermediate Similarity NPC56777
0.7634 Intermediate Similarity NPC263079
0.7629 Intermediate Similarity NPC139271
0.7629 Intermediate Similarity NPC121453
0.7629 Intermediate Similarity NPC235109
0.7629 Intermediate Similarity NPC304011
0.7624 Intermediate Similarity NPC470043
0.7624 Intermediate Similarity NPC470059
0.7624 Intermediate Similarity NPC470064
0.7624 Intermediate Similarity NPC470058
0.7624 Intermediate Similarity NPC470061
0.7624 Intermediate Similarity NPC470060
0.7624 Intermediate Similarity NPC31430
0.7624 Intermediate Similarity NPC85593
0.7624 Intermediate Similarity NPC100078
0.7624 Intermediate Similarity NPC470057
0.7624 Intermediate Similarity NPC470062
0.7614 Intermediate Similarity NPC477287

  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 NPC470872 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
0.75 Intermediate Similarity NPD8171 Discontinued
0.7294 Intermediate Similarity NPD7532 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD3670 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD3669 Approved
0.7143 Intermediate Similarity NPD6928 Phase 2
0.7115 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD1810 Approved
0.7045 Intermediate Similarity NPD1811 Approved
0.7009 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7516 Approved
0.6827 Remote Similarity NPD1700 Approved
0.6814 Remote Similarity NPD7328 Approved
0.6814 Remote Similarity NPD7327 Approved
0.6757 Remote Similarity NPD8133 Approved
0.6739 Remote Similarity NPD6115 Approved
0.6739 Remote Similarity NPD6697 Approved
0.6739 Remote Similarity NPD6118 Approved
0.6739 Remote Similarity NPD6114 Approved
0.6705 Remote Similarity NPD2686 Approved
0.6705 Remote Similarity NPD2687 Approved
0.6705 Remote Similarity NPD2254 Approved
0.6696 Remote Similarity NPD8377 Approved
0.6696 Remote Similarity NPD8294 Approved
0.6638 Remote Similarity NPD8378 Approved
0.6638 Remote Similarity NPD8033 Approved
0.6638 Remote Similarity NPD8296 Approved
0.6638 Remote Similarity NPD8335 Approved
0.6638 Remote Similarity NPD8380 Approved
0.6638 Remote Similarity NPD8379 Approved
0.663 Remote Similarity NPD6116 Phase 1
0.6591 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6588 Remote Similarity NPD371 Approved
0.6545 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6526 Remote Similarity NPD1780 Approved
0.6526 Remote Similarity NPD1779 Approved
0.6522 Remote Similarity NPD6117 Approved
0.6486 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6455 Remote Similarity NPD6686 Approved
0.6435 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6417 Remote Similarity NPD7507 Approved
0.6364 Remote Similarity NPD8293 Discontinued
0.6356 Remote Similarity NPD7503 Approved
0.6348 Remote Similarity NPD6940 Discontinued
0.6311 Remote Similarity NPD7736 Approved
0.6306 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6304 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6303 Remote Similarity NPD6370 Approved
0.626 Remote Similarity NPD7319 Approved
0.6216 Remote Similarity NPD6412 Phase 2
0.6216 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6198 Remote Similarity NPD7492 Approved
0.619 Remote Similarity NPD7991 Discontinued
0.6182 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6182 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6148 Remote Similarity NPD6616 Approved
0.6145 Remote Similarity NPD2267 Suspended
0.6134 Remote Similarity NPD6059 Approved
0.6134 Remote Similarity NPD6054 Approved
0.6116 Remote Similarity NPD8328 Phase 3
0.6098 Remote Similarity NPD7078 Approved
0.6064 Remote Similarity NPD3703 Phase 2
0.6055 Remote Similarity NPD5344 Discontinued
0.6019 Remote Similarity NPD7638 Approved
0.5984 Remote Similarity NPD6067 Discontinued
0.5963 Remote Similarity NPD7639 Approved
0.5963 Remote Similarity NPD7640 Approved
0.595 Remote Similarity NPD6015 Approved
0.595 Remote Similarity NPD6016 Approved
0.5948 Remote Similarity NPD6882 Approved
0.5914 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5914 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5905 Remote Similarity NPD8035 Phase 2
0.5905 Remote Similarity NPD8034 Phase 2
0.5902 Remote Similarity NPD5988 Approved
0.5895 Remote Similarity NPD3702 Approved
0.5882 Remote Similarity NPD6009 Approved
0.5872 Remote Similarity NPD4225 Approved
0.587 Remote Similarity NPD3699 Clinical (unspecified phase)
0.587 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5856 Remote Similarity NPD7632 Discontinued
0.5841 Remote Similarity NPD6008 Approved
0.582 Remote Similarity NPD6921 Approved
0.5818 Remote Similarity NPD6648 Approved
0.5812 Remote Similarity NPD8297 Approved
0.581 Remote Similarity NPD3168 Discontinued
0.5806 Remote Similarity NPD4787 Phase 1
0.5784 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5758 Remote Similarity NPD7525 Registered
0.5745 Remote Similarity NPD5777 Approved
0.5739 Remote Similarity NPD7320 Approved
0.5738 Remote Similarity NPD6319 Approved
0.5714 Remote Similarity NPD8139 Approved
0.5714 Remote Similarity NPD8086 Approved
0.5714 Remote Similarity NPD8082 Approved
0.5714 Remote Similarity NPD8085 Approved
0.5714 Remote Similarity NPD8084 Approved
0.5714 Remote Similarity NPD8138 Approved
0.5714 Remote Similarity NPD8083 Approved
0.5702 Remote Similarity NPD6402 Approved
0.5702 Remote Similarity NPD7128 Approved
0.5702 Remote Similarity NPD6675 Approved
0.5702 Remote Similarity NPD5739 Approved
0.5691 Remote Similarity NPD8516 Approved
0.5691 Remote Similarity NPD8517 Approved
0.5691 Remote Similarity NPD8515 Approved
0.5691 Remote Similarity NPD8513 Phase 3
0.569 Remote Similarity NPD6372 Approved
0.569 Remote Similarity NPD6373 Approved
0.5673 Remote Similarity NPD7524 Approved
0.5669 Remote Similarity NPD6033 Approved
0.5664 Remote Similarity NPD8276 Approved
0.5664 Remote Similarity NPD8275 Approved
0.5638 Remote Similarity NPD4244 Approved
0.5638 Remote Similarity NPD4245 Approved
0.563 Remote Similarity NPD4632 Approved
0.562 Remote Similarity NPD7115 Discovery
0.5614 Remote Similarity NPD8081 Approved
0.5604 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5603 Remote Similarity NPD6881 Approved
0.5603 Remote Similarity NPD6899 Approved
0.5603 Remote Similarity NPD8174 Phase 2
0.56 Remote Similarity NPD7604 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