Structure

Physi-Chem Properties

Molecular Weight:  335.17
Volume:  338.617
LogP:  1.953
LogD:  1.456
LogS:  -2.449
# Rotatable Bonds:  3
TPSA:  90.23
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.737
Synthetic Accessibility Score:  4.267
Fsp3:  0.611
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.886
MDCK Permeability:  8.086669549811631e-05
Pgp-inhibitor:  0.068
Pgp-substrate:  0.028
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.622
Plasma Protein Binding (PPB):  51.017295837402344%
Volume Distribution (VD):  0.884
Pgp-substrate:  42.21590805053711%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.112
CYP2C19-inhibitor:  0.039
CYP2C19-substrate:  0.887
CYP2C9-inhibitor:  0.02
CYP2C9-substrate:  0.405
CYP2D6-inhibitor:  0.028
CYP2D6-substrate:  0.274
CYP3A4-inhibitor:  0.053
CYP3A4-substrate:  0.718

ADMET: Excretion

Clearance (CL):  5.332
Half-life (T1/2):  0.377

ADMET: Toxicity

hERG Blockers:  0.018
Human Hepatotoxicity (H-HT):  0.381
Drug-inuced Liver Injury (DILI):  0.229
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.086
Maximum Recommended Daily Dose:  0.667
Skin Sensitization:  0.067
Carcinogencity:  0.116
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.007

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

  Natural Product: NPC469479

Natural Product ID:  NPC469479
Common Name*:   Rigidiusculamide D
IUPAC Name:   (3S,4S,5S)-3,4-dihydroxy-5-[[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl]-1,3-dimethylpyrrolidin-2-one
Synonyms:   Rigidiusculamide D
Standard InCHIKey:  YSTJGABLVSIEEQ-UJILACHPSA-N
Standard InCHI:  InChI=1S/C18H25NO5/c1-17(2,22)14-9-11-7-10(5-6-13(11)24-14)8-12-15(20)18(3,23)16(21)19(12)4/h5-7,12,14-15,20,22-23H,8-9H2,1-4H3/t12-,14?,15-,18-/m0/s1
SMILES:  CN1[C@@H](Cc2ccc3c(c2)CC(O3)C(O)(C)C)[C@@H]([C@](C1=O)(C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1079827
PubChem CID:   44614137
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0004189] Coumarans

*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
NPO32891 albonectria rigidiuscula Species Nectriaceae Eukaryota n.a. n.a. n.a. PMID[19919065]

☑ 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
NPT165 Cell Line HeLa Homo sapiens IC50 > 120000.0 nM PMID[559581]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 120000.0 nM PMID[559581]

☑ 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 NPC469479 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
0.9484 High Similarity NPC469505
0.8487 Intermediate Similarity NPC251439
0.7736 Intermediate Similarity NPC204546
0.7727 Intermediate Similarity NPC470903
0.7727 Intermediate Similarity NPC470112
0.7727 Intermediate Similarity NPC167763
0.7719 Intermediate Similarity NPC196091
0.7712 Intermediate Similarity NPC283079
0.7657 Intermediate Similarity NPC475421
0.7643 Intermediate Similarity NPC109580
0.7595 Intermediate Similarity NPC106606
0.7554 Intermediate Similarity NPC308709
0.7542 Intermediate Similarity NPC206061
0.7473 Intermediate Similarity NPC283207
0.7444 Intermediate Similarity NPC299806
0.7399 Intermediate Similarity NPC473502
0.7384 Intermediate Similarity NPC472923
0.7349 Intermediate Similarity NPC324081
0.7342 Intermediate Similarity NPC470392
0.7341 Intermediate Similarity NPC254700
0.7329 Intermediate Similarity NPC28641
0.7329 Intermediate Similarity NPC194359
0.7316 Intermediate Similarity NPC286135
0.7314 Intermediate Similarity NPC471568
0.7314 Intermediate Similarity NPC473693
0.7308 Intermediate Similarity NPC276120
0.7305 Intermediate Similarity NPC214239
0.729 Intermediate Similarity NPC141739
0.729 Intermediate Similarity NPC320242
0.729 Intermediate Similarity NPC136112
0.7258 Intermediate Similarity NPC94499
0.7257 Intermediate Similarity NPC186617
0.7253 Intermediate Similarity NPC315542
0.7247 Intermediate Similarity NPC129578
0.7234 Intermediate Similarity NPC66909
0.7229 Intermediate Similarity NPC130206
0.7229 Intermediate Similarity NPC313414
0.7204 Intermediate Similarity NPC319549
0.7189 Intermediate Similarity NPC223384
0.7175 Intermediate Similarity NPC328494
0.7165 Intermediate Similarity NPC79130
0.7159 Intermediate Similarity NPC35345
0.7158 Intermediate Similarity NPC123859
0.7143 Intermediate Similarity NPC49577
0.7143 Intermediate Similarity NPC474855
0.7143 Intermediate Similarity NPC474787
0.7143 Intermediate Similarity NPC474811
0.7143 Intermediate Similarity NPC79465
0.7143 Intermediate Similarity NPC76785
0.7143 Intermediate Similarity NPC90194
0.7143 Intermediate Similarity NPC476102
0.7143 Intermediate Similarity NPC9687
0.7143 Intermediate Similarity NPC273907
0.7143 Intermediate Similarity NPC293377
0.7143 Intermediate Similarity NPC260045
0.7143 Intermediate Similarity NPC118099
0.7143 Intermediate Similarity NPC475598
0.7143 Intermediate Similarity NPC471396
0.7143 Intermediate Similarity NPC151706
0.7143 Intermediate Similarity NPC475318
0.7135 Intermediate Similarity NPC475747
0.7135 Intermediate Similarity NPC471073
0.7135 Intermediate Similarity NPC270811
0.7135 Intermediate Similarity NPC230098
0.7125 Intermediate Similarity NPC97870
0.7125 Intermediate Similarity NPC247018
0.7125 Intermediate Similarity NPC307123
0.712 Intermediate Similarity NPC475981
0.712 Intermediate Similarity NPC474746
0.711 Intermediate Similarity NPC476443
0.711 Intermediate Similarity NPC133817
0.7108 Intermediate Similarity NPC184053
0.7105 Intermediate Similarity NPC293624
0.7102 Intermediate Similarity NPC218614
0.7099 Intermediate Similarity NPC477210
0.7095 Intermediate Similarity NPC164608
0.7093 Intermediate Similarity NPC474772
0.7093 Intermediate Similarity NPC472423
0.7093 Intermediate Similarity NPC474744
0.7083 Intermediate Similarity NPC254045
0.7083 Intermediate Similarity NPC151470
0.7083 Intermediate Similarity NPC201055
0.7083 Intermediate Similarity NPC64576
0.7081 Intermediate Similarity NPC132308
0.7079 Intermediate Similarity NPC284842
0.7079 Intermediate Similarity NPC252960
0.7059 Intermediate Similarity NPC469540
0.7059 Intermediate Similarity NPC469539
0.7059 Intermediate Similarity NPC202494
0.7059 Intermediate Similarity NPC469425
0.7056 Intermediate Similarity NPC197125
0.7053 Intermediate Similarity NPC474432
0.7053 Intermediate Similarity NPC475713
0.7052 Intermediate Similarity NPC285623
0.7052 Intermediate Similarity NPC319320
0.7052 Intermediate Similarity NPC287757
0.7049 Intermediate Similarity NPC474745
0.7049 Intermediate Similarity NPC99723
0.7043 Intermediate Similarity NPC471395
0.7035 Intermediate Similarity NPC472421
0.7033 Intermediate Similarity NPC474470
0.7033 Intermediate Similarity NPC32064
0.7031 Intermediate Similarity NPC474427
0.7024 Intermediate Similarity NPC189908
0.7024 Intermediate Similarity NPC9373
0.7022 Intermediate Similarity NPC474858
0.7021 Intermediate Similarity NPC196231
0.7019 Intermediate Similarity NPC318862
0.7013 Intermediate Similarity NPC321133
0.7012 Intermediate Similarity NPC231163
0.7012 Intermediate Similarity NPC225745
0.7012 Intermediate Similarity NPC318591
0.7011 Intermediate Similarity NPC473562
0.7011 Intermediate Similarity NPC115906
0.7011 Intermediate Similarity NPC37205
0.7011 Intermediate Similarity NPC160931
0.701 Intermediate Similarity NPC235698
0.7006 Intermediate Similarity NPC171372
0.7005 Intermediate Similarity NPC293347
0.7 Intermediate Similarity NPC469700
0.7 Intermediate Similarity NPC149962
0.7 Intermediate Similarity NPC474302
0.6995 Remote Similarity NPC329816
0.6995 Remote Similarity NPC474325
0.6995 Remote Similarity NPC309692
0.6994 Remote Similarity NPC472580
0.6994 Remote Similarity NPC254412
0.6994 Remote Similarity NPC262038
0.6994 Remote Similarity NPC319910
0.6994 Remote Similarity NPC262039
0.6994 Remote Similarity NPC278476
0.6994 Remote Similarity NPC472636
0.6994 Remote Similarity NPC471675
0.6983 Remote Similarity NPC472582
0.6982 Remote Similarity NPC132771
0.6978 Remote Similarity NPC304675
0.6975 Remote Similarity NPC2190
0.6973 Remote Similarity NPC102760
0.6971 Remote Similarity NPC217706
0.6971 Remote Similarity NPC207809
0.6971 Remote Similarity NPC259710
0.6971 Remote Similarity NPC48579
0.6971 Remote Similarity NPC304207
0.697 Remote Similarity NPC14390
0.697 Remote Similarity NPC150712
0.6964 Remote Similarity NPC171870
0.6964 Remote Similarity NPC74397
0.6963 Remote Similarity NPC144314
0.6962 Remote Similarity NPC65310
0.6961 Remote Similarity NPC476459
0.6959 Remote Similarity NPC14875
0.6959 Remote Similarity NPC473133
0.6959 Remote Similarity NPC91902
0.6959 Remote Similarity NPC470670
0.6959 Remote Similarity NPC47388
0.6957 Remote Similarity NPC99179
0.6954 Remote Similarity NPC473996
0.6954 Remote Similarity NPC216035
0.6954 Remote Similarity NPC476238
0.6954 Remote Similarity NPC35567
0.6954 Remote Similarity NPC243171
0.6954 Remote Similarity NPC31627
0.6954 Remote Similarity NPC171651
0.6954 Remote Similarity NPC327269
0.6954 Remote Similarity NPC217149
0.6954 Remote Similarity NPC477957
0.6954 Remote Similarity NPC138288
0.6951 Remote Similarity NPC307682
0.6947 Remote Similarity NPC184933
0.6947 Remote Similarity NPC59827
0.6944 Remote Similarity NPC290759
0.6944 Remote Similarity NPC266176
0.6944 Remote Similarity NPC82533
0.6944 Remote Similarity NPC158148
0.6943 Remote Similarity NPC244876
0.6941 Remote Similarity NPC297788
0.694 Remote Similarity NPC237044
0.6939 Remote Similarity NPC80472
0.6936 Remote Similarity NPC105136
0.6932 Remote Similarity NPC20530
0.6932 Remote Similarity NPC215917
0.6932 Remote Similarity NPC10754
0.6927 Remote Similarity NPC124657
0.6927 Remote Similarity NPC329717
0.6927 Remote Similarity NPC50548
0.6919 Remote Similarity NPC477160
0.6918 Remote Similarity NPC476353
0.6918 Remote Similarity NPC218323
0.6915 Remote Similarity NPC29531
0.6914 Remote Similarity NPC180301
0.6914 Remote Similarity NPC293286
0.6914 Remote Similarity NPC88983
0.6914 Remote Similarity NPC474246
0.6914 Remote Similarity NPC474143
0.6914 Remote Similarity NPC248793
0.6911 Remote Similarity NPC33256
0.691 Remote Similarity NPC472962
0.691 Remote Similarity NPC472961
0.6909 Remote Similarity NPC193528
0.6909 Remote Similarity NPC248505

  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 NPC469479 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
0.8466 Intermediate Similarity NPD2042 Clinical (unspecified phase)
0.8466 Intermediate Similarity NPD2041 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD2904 Discontinued
0.7821 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD2240 Approved
0.7722 Intermediate Similarity NPD2239 Approved
0.7674 Intermediate Similarity NPD2388 Discontinued
0.7654 Intermediate Similarity NPD3863 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD4210 Discontinued
0.7627 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD4666 Phase 3
0.7578 Intermediate Similarity NPD4236 Phase 3
0.7578 Intermediate Similarity NPD4237 Approved
0.7561 Intermediate Similarity NPD3536 Discontinued
0.7544 Intermediate Similarity NPD5709 Phase 3
0.7542 Intermediate Similarity NPD4483 Discontinued
0.7529 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD7131 Phase 3
0.7455 Intermediate Similarity NPD3146 Approved
0.7455 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD6667 Approved
0.7439 Intermediate Similarity NPD6666 Approved
0.7436 Intermediate Similarity NPD3179 Approved
0.7436 Intermediate Similarity NPD3180 Approved
0.7401 Intermediate Similarity NPD6042 Phase 2
0.7401 Intermediate Similarity NPD42 Phase 2
0.7396 Intermediate Similarity NPD6677 Suspended
0.7396 Intermediate Similarity NPD6072 Discontinued
0.7349 Intermediate Similarity NPD4661 Approved
0.7349 Intermediate Similarity NPD4662 Approved
0.731 Intermediate Similarity NPD6668 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD1817 Approved
0.729 Intermediate Similarity NPD1818 Approved
0.729 Intermediate Similarity NPD1820 Approved
0.729 Intermediate Similarity NPD1819 Approved
0.729 Intermediate Similarity NPD1794 Approved
0.7284 Intermediate Similarity NPD4476 Approved
0.7284 Intermediate Similarity NPD6032 Approved
0.7284 Intermediate Similarity NPD4477 Approved
0.7256 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD2163 Approved
0.7234 Intermediate Similarity NPD2974 Approved
0.7234 Intermediate Similarity NPD2973 Approved
0.7234 Intermediate Similarity NPD2975 Approved
0.7233 Intermediate Similarity NPD3163 Approved
0.7233 Intermediate Similarity NPD5745 Approved
0.7233 Intermediate Similarity NPD3162 Approved
0.7216 Intermediate Similarity NPD7608 Discontinued
0.7215 Intermediate Similarity NPD3165 Approved
0.7215 Intermediate Similarity NPD3166 Approved
0.7215 Intermediate Similarity NPD3164 Approved
0.7215 Intermediate Similarity NPD3167 Approved
0.7212 Intermediate Similarity NPD2575 Approved
0.7209 Intermediate Similarity NPD5773 Approved
0.7209 Intermediate Similarity NPD5772 Approved
0.7209 Intermediate Similarity NPD7972 Discontinued
0.7205 Intermediate Similarity NPD3054 Approved
0.7205 Intermediate Similarity NPD3052 Approved
0.7204 Intermediate Similarity NPD7296 Approved
0.7184 Intermediate Similarity NPD8031 Discontinued
0.7181 Intermediate Similarity NPD4361 Phase 2
0.7181 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7173 Intermediate Similarity NPD2493 Approved
0.7173 Intermediate Similarity NPD2494 Approved
0.7169 Intermediate Similarity NPD2677 Approved
0.716 Intermediate Similarity NPD1670 Discontinued
0.7152 Intermediate Similarity NPD2654 Approved
0.7151 Intermediate Similarity NPD2488 Approved
0.7151 Intermediate Similarity NPD2490 Approved
0.7151 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD4433 Discontinued
0.7143 Intermediate Similarity NPD6315 Phase 2
0.7143 Intermediate Similarity NPD6355 Discontinued
0.7127 Intermediate Similarity NPD3823 Discontinued
0.7126 Intermediate Similarity NPD4947 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD5295 Discontinued
0.7125 Intermediate Similarity NPD1423 Approved
0.712 Intermediate Similarity NPD4580 Approved
0.7107 Intermediate Similarity NPD5746 Approved
0.7104 Intermediate Similarity NPD7281 Phase 3
0.7104 Intermediate Similarity NPD7280 Phase 3
0.7101 Intermediate Similarity NPD2676 Approved
0.7101 Intermediate Similarity NPD2675 Approved
0.7093 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD2424 Discontinued
0.7091 Intermediate Similarity NPD2897 Discontinued
0.7083 Intermediate Similarity NPD3452 Approved
0.7083 Intermediate Similarity NPD3450 Approved
0.7081 Intermediate Similarity NPD3597 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD8051 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD5137 Approved
0.7076 Intermediate Similarity NPD2651 Approved
0.7076 Intermediate Similarity NPD2649 Approved
0.7074 Intermediate Similarity NPD4466 Phase 1
0.7073 Intermediate Similarity NPD3175 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD7318 Phase 3
0.7063 Intermediate Similarity NPD6798 Discontinued
0.7062 Intermediate Similarity NPD4583 Approved
0.7062 Intermediate Similarity NPD4582 Approved
0.7059 Intermediate Similarity NPD7427 Discontinued
0.7056 Intermediate Similarity NPD7177 Discontinued
0.7056 Intermediate Similarity NPD6620 Discovery
0.7052 Intermediate Similarity NPD6844 Discontinued
0.7052 Intermediate Similarity NPD7248 Discontinued
0.7048 Intermediate Similarity NPD4162 Approved
0.7048 Intermediate Similarity NPD5061 Approved
0.7048 Intermediate Similarity NPD5062 Approved
0.7041 Intermediate Similarity NPD7019 Approved
0.7041 Intermediate Similarity NPD7020 Approved
0.7031 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD3122 Phase 3
0.7022 Intermediate Similarity NPD3051 Approved
0.7018 Intermediate Similarity NPD3687 Approved
0.7018 Intermediate Similarity NPD3686 Approved
0.7013 Intermediate Similarity NPD2668 Approved
0.7013 Intermediate Similarity NPD2667 Approved
0.7012 Intermediate Similarity NPD2155 Approved
0.7012 Intermediate Similarity NPD2154 Approved
0.7012 Intermediate Similarity NPD2156 Approved
0.7011 Intermediate Similarity NPD3465 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD2971 Approved
0.7011 Intermediate Similarity NPD2968 Approved
0.701 Intermediate Similarity NPD4004 Approved
0.701 Intermediate Similarity NPD4002 Approved
0.7 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.6989 Remote Similarity NPD8070 Approved
0.6988 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6983 Remote Similarity NPD2969 Approved
0.6983 Remote Similarity NPD2970 Approved
0.6981 Remote Similarity NPD3662 Phase 3
0.6981 Remote Similarity NPD3663 Approved
0.6981 Remote Similarity NPD3664 Approved
0.6981 Remote Similarity NPD3661 Approved
0.697 Remote Similarity NPD1725 Approved
0.6966 Remote Similarity NPD7484 Phase 3
0.6966 Remote Similarity NPD7485 Phase 3
0.6962 Remote Similarity NPD2628 Approved
0.6962 Remote Similarity NPD2160 Approved
0.6962 Remote Similarity NPD2625 Approved
0.6962 Remote Similarity NPD2627 Approved
0.6962 Remote Similarity NPD2626 Approved
0.6962 Remote Similarity NPD2159 Approved
0.6961 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5976 Discontinued
0.6957 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6954 Remote Similarity NPD4018 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7317 Phase 3
0.6951 Remote Similarity NPD5688 Approved
0.6951 Remote Similarity NPD5689 Approved
0.6944 Remote Similarity NPD2489 Approved
0.6944 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6944 Remote Similarity NPD27 Approved
0.6935 Remote Similarity NPD3154 Approved
0.6935 Remote Similarity NPD3153 Approved
0.6928 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6927 Remote Similarity NPD6997 Phase 2
0.6918 Remote Similarity NPD3691 Phase 2
0.6918 Remote Similarity NPD3690 Phase 2
0.6905 Remote Similarity NPD7466 Approved
0.6905 Remote Similarity NPD3400 Discontinued
0.689 Remote Similarity NPD2157 Approved
0.6886 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6882 Remote Similarity NPD7213 Phase 3
0.6882 Remote Similarity NPD1774 Approved
0.6882 Remote Similarity NPD7212 Phase 2
0.6875 Remote Similarity NPD2560 Approved
0.6875 Remote Similarity NPD2563 Approved
0.6875 Remote Similarity NPD5204 Approved
0.6872 Remote Similarity NPD3057 Approved
0.6871 Remote Similarity NPD6310 Approved
0.6871 Remote Similarity NPD2238 Phase 2
0.6871 Remote Similarity NPD6311 Approved
0.6871 Remote Similarity NPD3140 Approved
0.6871 Remote Similarity NPD6309 Approved
0.6871 Remote Similarity NPD3142 Approved
0.6865 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6864 Remote Similarity NPD5160 Discontinued
0.6857 Remote Similarity NPD5355 Approved
0.6857 Remote Similarity NPD5356 Approved
0.6855 Remote Similarity NPD4103 Phase 2
0.6855 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6852 Remote Similarity NPD4621 Approved
0.6852 Remote Similarity NPD4619 Approved
0.6852 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6848 Remote Similarity NPD2200 Suspended
0.6848 Remote Similarity NPD743 Approved
0.6848 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6845 Remote Similarity NPD3060 Approved
0.6842 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6842 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7447 Phase 1
0.6836 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6833 Remote Similarity NPD7315 Approved
0.6831 Remote Similarity NPD5313 Approved
0.6831 Remote Similarity NPD5312 Approved
0.6829 Remote Similarity NPD4618 Approved
0.6829 Remote Similarity NPD4622 Approved
0.6826 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6826 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6826 Remote Similarity NPD6002 Phase 3

  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