Structure

Physi-Chem Properties

Molecular Weight:  756.37
Volume:  771.374
LogP:  2.641
LogD:  2.61
LogS:  -5.047
# Rotatable Bonds:  20
TPSA:  201.67
# H-Bond Aceptor:  13
# H-Bond Donor:  6
# Rings:  4
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.074
Synthetic Accessibility Score:  5.122
Fsp3:  0.561
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:  -5.472
MDCK Permeability:  1.8721464584814385e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.712
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.239
Plasma Protein Binding (PPB):  87.34162139892578%
Volume Distribution (VD):  0.418
Pgp-substrate:  10.660412788391113%

ADMET: Metabolism

CYP1A2-inhibitor:  0.187
CYP1A2-substrate:  0.285
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.07
CYP2C9-inhibitor:  0.052
CYP2C9-substrate:  0.015
CYP2D6-inhibitor:  0.026
CYP2D6-substrate:  0.053
CYP3A4-inhibitor:  0.948
CYP3A4-substrate:  0.26

ADMET: Excretion

Clearance (CL):  7.401
Half-life (T1/2):  0.879

ADMET: Toxicity

hERG Blockers:  0.867
Human Hepatotoxicity (H-HT):  0.132
Drug-inuced Liver Injury (DILI):  0.922
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.012
Maximum Recommended Daily Dose:  0.996
Skin Sensitization:  0.767
Carcinogencity:  0.285
Eye Corrosion:  0.003
Eye Irritation:  0.016
Respiratory Toxicity:  0.864

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

  Natural Product: NPC471876

Natural Product ID:  NPC471876
Common Name*:   Bis(((1S,3S,4R)-3-Hydroxy-4-(2-Hydroxyethyl)-4-(Hydroxymethyl)Cyclohexyl)Methyl)-2-(3,4-Dimethoxybenzylidene)-3-(4-Methoxybenzylidene)Succinate
IUPAC Name:   bis[[(1S,3S,4R)-3-hydroxy-4-(2-hydroxyethyl)-4-(hydroxymethyl)cyclohexyl]methyl] (2E,3E)-2-[(3,4-dimethoxyphenyl)methylidene]-3-[(4-methoxyphenyl)methylidene]butanedioate
Synonyms:  
Standard InCHIKey:  VTSBTHIWQORHLC-BDTXOSOMSA-N
Standard InCHI:  InChI=1S/C41H56O13/c1-50-31-7-4-27(5-8-31)18-32(38(48)53-23-29-10-12-40(25-44,14-16-42)36(46)21-29)33(19-28-6-9-34(51-2)35(20-28)52-3)39(49)54-24-30-11-13-41(26-45,15-17-43)37(47)22-30/h4-9,18-20,29-30,36-37,42-47H,10-17,21-26H2,1-3H3/b32-18+,33-19+/t29-,30-,36-,37-,40+,41+/m0/s1
SMILES:  OCC[C@@]1(CO)CC[C@@H](C[C@@H]1O)COC(=O)/C(=C/c1ccc(c(c1)OC)OC)/C(=Cc1ccc(cc1)OC)/C(=O)OC[C@H]1CC[C@]([C@H](C1)O)(CO)CCO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3262205
PubChem CID:   90676288
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO9348 Cananga odorata Species Annonaceae Eukaryota fruits n.a. n.a. PMID[11374955]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21504145]
NPO9348 Cananga odorata Species Annonaceae Eukaryota flower buds Thailand n.a. PMID[24601675]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ 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
NPT2 Others Unspecified Inhibition = 34.4 % PMID[529764]
NPT2 Others Unspecified Inhibition = 24.1 % PMID[529764]
NPT2 Others Unspecified Inhibition = 8.1 % PMID[529764]
NPT2 Others Unspecified Inhibition = -19.9 % PMID[529764]
NPT2 Others Unspecified Inhibition = 15.7 % PMID[529764]
NPT27 Others Unspecified Activity = 68.8 % PMID[529764]
NPT27 Others Unspecified Activity = 82.0 % PMID[529764]

☑ 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 NPC471876 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
0.9143 High Similarity NPC471875
0.9128 High Similarity NPC471878
0.8792 High Similarity NPC473773
0.8792 High Similarity NPC475579
0.8784 High Similarity NPC145527
0.8784 High Similarity NPC470618
0.8784 High Similarity NPC470619
0.8784 High Similarity NPC208785
0.8741 High Similarity NPC110699
0.8741 High Similarity NPC106055
0.8725 High Similarity NPC118033
0.8699 High Similarity NPC307205
0.8662 High Similarity NPC120852
0.86 High Similarity NPC473680
0.86 High Similarity NPC475311
0.86 High Similarity NPC473579
0.86 High Similarity NPC475454
0.8591 High Similarity NPC273358
0.8591 High Similarity NPC298647
0.8571 High Similarity NPC19862
0.8571 High Similarity NPC143120
0.8571 High Similarity NPC473909
0.8571 High Similarity NPC235195
0.8571 High Similarity NPC274960
0.8542 High Similarity NPC76032
0.8542 High Similarity NPC132723
0.8523 High Similarity NPC32017
0.8523 High Similarity NPC96930
0.8487 Intermediate Similarity NPC471874
0.8487 Intermediate Similarity NPC205392
0.8487 Intermediate Similarity NPC105942
0.8467 Intermediate Similarity NPC292206
0.8446 Intermediate Similarity NPC280717
0.8446 Intermediate Similarity NPC271607
0.8429 Intermediate Similarity NPC83062
0.8392 Intermediate Similarity NPC135127
0.8378 Intermediate Similarity NPC304956
0.8378 Intermediate Similarity NPC26045
0.8375 Intermediate Similarity NPC266545
0.8375 Intermediate Similarity NPC202428
0.8367 Intermediate Similarity NPC67467
0.8366 Intermediate Similarity NPC115203
0.8356 Intermediate Similarity NPC155192
0.8356 Intermediate Similarity NPC271494
0.8356 Intermediate Similarity NPC473591
0.8344 Intermediate Similarity NPC475250
0.8333 Intermediate Similarity NPC113295
0.8323 Intermediate Similarity NPC472803
0.8323 Intermediate Similarity NPC473275
0.8323 Intermediate Similarity NPC470896
0.8322 Intermediate Similarity NPC258671
0.8322 Intermediate Similarity NPC53884
0.8322 Intermediate Similarity NPC475468
0.8322 Intermediate Similarity NPC53520
0.8313 Intermediate Similarity NPC177362
0.8311 Intermediate Similarity NPC235557
0.8309 Intermediate Similarity NPC471877
0.8301 Intermediate Similarity NPC478268
0.8288 Intermediate Similarity NPC182249
0.8278 Intermediate Similarity NPC1580
0.8278 Intermediate Similarity NPC102934
0.8278 Intermediate Similarity NPC252402
0.8276 Intermediate Similarity NPC90431
0.8264 Intermediate Similarity NPC471110
0.8258 Intermediate Similarity NPC131532
0.8255 Intermediate Similarity NPC25491
0.825 Intermediate Similarity NPC200726
0.8243 Intermediate Similarity NPC472410
0.8231 Intermediate Similarity NPC470616
0.8231 Intermediate Similarity NPC470617
0.8219 Intermediate Similarity NPC281780
0.8219 Intermediate Similarity NPC126206
0.8214 Intermediate Similarity NPC120225
0.8214 Intermediate Similarity NPC213552
0.8212 Intermediate Similarity NPC221383
0.8212 Intermediate Similarity NPC299090
0.8212 Intermediate Similarity NPC143892
0.8212 Intermediate Similarity NPC283081
0.82 Intermediate Similarity NPC476382
0.82 Intermediate Similarity NPC100998
0.82 Intermediate Similarity NPC34927
0.82 Intermediate Similarity NPC34587
0.82 Intermediate Similarity NPC252292
0.8194 Intermediate Similarity NPC469888
0.8188 Intermediate Similarity NPC310621
0.8188 Intermediate Similarity NPC252133
0.8188 Intermediate Similarity NPC477873
0.8188 Intermediate Similarity NPC469447
0.8182 Intermediate Similarity NPC476434
0.8176 Intermediate Similarity NPC304110
0.8176 Intermediate Similarity NPC100675
0.8176 Intermediate Similarity NPC27518
0.8176 Intermediate Similarity NPC471873
0.8163 Intermediate Similarity NPC139243
0.8163 Intermediate Similarity NPC116742
0.8162 Intermediate Similarity NPC474320
0.816 Intermediate Similarity NPC469772
0.816 Intermediate Similarity NPC469777
0.816 Intermediate Similarity NPC469776
0.816 Intermediate Similarity NPC469775
0.816 Intermediate Similarity NPC100925
0.816 Intermediate Similarity NPC469773
0.816 Intermediate Similarity NPC295941
0.816 Intermediate Similarity NPC32723
0.816 Intermediate Similarity NPC469778
0.816 Intermediate Similarity NPC135334
0.816 Intermediate Similarity NPC469774
0.8153 Intermediate Similarity NPC125495
0.8151 Intermediate Similarity NPC471665
0.8151 Intermediate Similarity NPC471664
0.8143 Intermediate Similarity NPC289459
0.8138 Intermediate Similarity NPC37065
0.8129 Intermediate Similarity NPC475141
0.8121 Intermediate Similarity NPC35212
0.8121 Intermediate Similarity NPC140502
0.8121 Intermediate Similarity NPC46180
0.8117 Intermediate Similarity NPC243891
0.8117 Intermediate Similarity NPC477379
0.8117 Intermediate Similarity NPC119252
0.8113 Intermediate Similarity NPC216916
0.8113 Intermediate Similarity NPC471869
0.8105 Intermediate Similarity NPC476398
0.8105 Intermediate Similarity NPC259347
0.8105 Intermediate Similarity NPC94871
0.8105 Intermediate Similarity NPC471062
0.8105 Intermediate Similarity NPC470933
0.8105 Intermediate Similarity NPC476386
0.8105 Intermediate Similarity NPC306890
0.8105 Intermediate Similarity NPC478242
0.8105 Intermediate Similarity NPC473427
0.8101 Intermediate Similarity NPC173726
0.8101 Intermediate Similarity NPC241600
0.8101 Intermediate Similarity NPC478269
0.8095 Intermediate Similarity NPC22676
0.8095 Intermediate Similarity NPC198621
0.8095 Intermediate Similarity NPC216940
0.8095 Intermediate Similarity NPC475482
0.8092 Intermediate Similarity NPC232992
0.8092 Intermediate Similarity NPC295297
0.8092 Intermediate Similarity NPC15577
0.8089 Intermediate Similarity NPC228357
0.8089 Intermediate Similarity NPC11411
0.8088 Intermediate Similarity NPC474214
0.8088 Intermediate Similarity NPC277460
0.8086 Intermediate Similarity NPC286809
0.8085 Intermediate Similarity NPC118584
0.8079 Intermediate Similarity NPC469683
0.8079 Intermediate Similarity NPC163898
0.8077 Intermediate Similarity NPC473736
0.8077 Intermediate Similarity NPC62051
0.8071 Intermediate Similarity NPC146886
0.8071 Intermediate Similarity NPC246704
0.8071 Intermediate Similarity NPC20443
0.8071 Intermediate Similarity NPC60517
0.8065 Intermediate Similarity NPC267091
0.8063 Intermediate Similarity NPC476371
0.8063 Intermediate Similarity NPC476372
0.8054 Intermediate Similarity NPC29599
0.8054 Intermediate Similarity NPC473612
0.8052 Intermediate Similarity NPC229882
0.8052 Intermediate Similarity NPC477381
0.8052 Intermediate Similarity NPC470934
0.8052 Intermediate Similarity NPC158635
0.8052 Intermediate Similarity NPC257970
0.8052 Intermediate Similarity NPC188393
0.8052 Intermediate Similarity NPC470927
0.805 Intermediate Similarity NPC476373
0.8041 Intermediate Similarity NPC260842
0.8039 Intermediate Similarity NPC215095
0.8039 Intermediate Similarity NPC300262
0.8039 Intermediate Similarity NPC261122
0.8039 Intermediate Similarity NPC199311
0.8039 Intermediate Similarity NPC236166
0.8039 Intermediate Similarity NPC80732
0.8039 Intermediate Similarity NPC28651
0.8039 Intermediate Similarity NPC210611
0.8039 Intermediate Similarity NPC3460
0.8039 Intermediate Similarity NPC476348
0.8039 Intermediate Similarity NPC187398
0.8039 Intermediate Similarity NPC472969
0.8039 Intermediate Similarity NPC192763
0.8039 Intermediate Similarity NPC201148
0.8038 Intermediate Similarity NPC268602
0.8028 Intermediate Similarity NPC223807
0.8027 Intermediate Similarity NPC471719
0.8027 Intermediate Similarity NPC471872
0.8027 Intermediate Similarity NPC471988
0.8027 Intermediate Similarity NPC154485
0.8027 Intermediate Similarity NPC249817
0.8026 Intermediate Similarity NPC268515
0.8026 Intermediate Similarity NPC8102
0.8026 Intermediate Similarity NPC66894
0.8026 Intermediate Similarity NPC40222
0.8014 Intermediate Similarity NPC309744
0.8014 Intermediate Similarity NPC5310
0.8014 Intermediate Similarity NPC176814
0.8014 Intermediate Similarity NPC68779
0.8014 Intermediate Similarity NPC67951
0.8014 Intermediate Similarity NPC4982
0.8014 Intermediate Similarity NPC67247

  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 NPC471876 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
0.8462 Intermediate Similarity NPD8127 Discontinued
0.8207 Intermediate Similarity NPD7097 Phase 1
0.8 Intermediate Similarity NPD8166 Discontinued
0.7917 Intermediate Similarity NPD7095 Approved
0.7898 Intermediate Similarity NPD37 Approved
0.7881 Intermediate Similarity NPD4110 Phase 3
0.7881 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD4967 Phase 2
0.7862 Intermediate Similarity NPD4965 Approved
0.7862 Intermediate Similarity NPD4966 Approved
0.7857 Intermediate Similarity NPD6273 Approved
0.78 Intermediate Similarity NPD7266 Discontinued
0.7754 Intermediate Similarity NPD5536 Phase 2
0.775 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD7458 Discontinued
0.7706 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD6234 Discontinued
0.7651 Intermediate Similarity NPD7228 Approved
0.7647 Intermediate Similarity NPD4628 Phase 3
0.7635 Intermediate Similarity NPD4140 Approved
0.7619 Intermediate Similarity NPD6798 Discontinued
0.7613 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD5844 Phase 1
0.7597 Intermediate Similarity NPD6190 Approved
0.7591 Intermediate Similarity NPD5283 Phase 1
0.759 Intermediate Similarity NPD7473 Discontinued
0.7584 Intermediate Similarity NPD6355 Discontinued
0.7568 Intermediate Similarity NPD6233 Phase 2
0.7551 Intermediate Similarity NPD3027 Phase 3
0.7532 Intermediate Similarity NPD7003 Approved
0.7517 Intermediate Similarity NPD3620 Phase 2
0.7517 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6232 Discontinued
0.7515 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6032 Approved
0.7471 Intermediate Similarity NPD7685 Pre-registration
0.7471 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7240 Approved
0.7468 Intermediate Similarity NPD6674 Discontinued
0.7452 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD8455 Phase 2
0.74 Intermediate Similarity NPD4060 Phase 1
0.7394 Intermediate Similarity NPD5585 Approved
0.7386 Intermediate Similarity NPD2935 Discontinued
0.7386 Intermediate Similarity NPD2438 Suspended
0.7375 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD3817 Phase 2
0.7358 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD7157 Approved
0.7351 Intermediate Similarity NPD447 Suspended
0.7349 Intermediate Similarity NPD7199 Phase 2
0.7333 Intermediate Similarity NPD8032 Phase 2
0.7329 Intermediate Similarity NPD7028 Phase 2
0.7321 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD6166 Phase 2
0.7321 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD1653 Approved
0.7303 Intermediate Similarity NPD6653 Approved
0.7297 Intermediate Similarity NPD5736 Approved
0.7292 Intermediate Similarity NPD3496 Discontinued
0.7285 Intermediate Similarity NPD1613 Approved
0.7285 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD8312 Approved
0.7283 Intermediate Similarity NPD8313 Approved
0.7279 Intermediate Similarity NPD2797 Approved
0.7279 Intermediate Similarity NPD1358 Approved
0.7273 Intermediate Similarity NPD5691 Approved
0.7273 Intermediate Similarity NPD1357 Approved
0.7266 Intermediate Similarity NPD7843 Approved
0.7266 Intermediate Similarity NPD5535 Approved
0.7257 Intermediate Similarity NPD8434 Phase 2
0.7251 Intermediate Similarity NPD7074 Phase 3
0.7239 Intermediate Similarity NPD1934 Approved
0.7237 Intermediate Similarity NPD5735 Approved
0.7235 Intermediate Similarity NPD3818 Discontinued
0.7233 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD5763 Approved
0.7226 Intermediate Similarity NPD5762 Approved
0.7222 Intermediate Similarity NPD4626 Approved
0.7222 Intermediate Similarity NPD1778 Approved
0.7211 Intermediate Similarity NPD1283 Approved
0.7208 Intermediate Similarity NPD2799 Discontinued
0.7206 Intermediate Similarity NPD3134 Approved
0.7197 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD7819 Suspended
0.7193 Intermediate Similarity NPD7054 Approved
0.7191 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD5494 Approved
0.7179 Intermediate Similarity NPD2424 Discontinued
0.7178 Intermediate Similarity NPD6386 Approved
0.7178 Intermediate Similarity NPD6677 Suspended
0.7178 Intermediate Similarity NPD6873 Phase 2
0.7178 Intermediate Similarity NPD6385 Approved
0.7172 Intermediate Similarity NPD3847 Discontinued
0.7171 Intermediate Similarity NPD2979 Phase 3
0.716 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD3268 Approved
0.7152 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7985 Registered
0.7152 Intermediate Similarity NPD5402 Approved
0.7151 Intermediate Similarity NPD7472 Approved
0.7143 Intermediate Similarity NPD5327 Phase 3
0.7143 Intermediate Similarity NPD4359 Approved
0.7134 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD6832 Phase 2
0.7126 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7808 Phase 3
0.7124 Intermediate Similarity NPD1933 Approved
0.7124 Intermediate Similarity NPD3657 Discovery
0.7117 Intermediate Similarity NPD4380 Phase 2
0.7115 Intermediate Similarity NPD2346 Discontinued
0.7108 Intermediate Similarity NPD7768 Phase 2
0.7105 Intermediate Similarity NPD6663 Approved
0.7105 Intermediate Similarity NPD4062 Phase 3
0.7091 Intermediate Similarity NPD1465 Phase 2
0.7091 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD2801 Approved
0.7081 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD228 Approved
0.707 Intermediate Similarity NPD4534 Discontinued
0.7069 Intermediate Similarity NPD7038 Approved
0.7069 Intermediate Similarity NPD7039 Approved
0.7067 Intermediate Similarity NPD9494 Approved
0.7066 Intermediate Similarity NPD7075 Discontinued
0.7055 Intermediate Similarity NPD3226 Approved
0.7039 Intermediate Similarity NPD2313 Discontinued
0.703 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD7549 Discontinued
0.7025 Intermediate Similarity NPD5177 Phase 3
0.702 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD4908 Phase 1
0.7013 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD5124 Phase 1
0.7012 Intermediate Similarity NPD6599 Discontinued
0.7007 Intermediate Similarity NPD1281 Approved
0.7006 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD3882 Suspended
0.6994 Remote Similarity NPD3686 Approved
0.6994 Remote Similarity NPD3687 Approved
0.6993 Remote Similarity NPD4870 Approved
0.6993 Remote Similarity NPD4198 Discontinued
0.6987 Remote Similarity NPD4308 Phase 3
0.6987 Remote Similarity NPD7033 Discontinued
0.698 Remote Similarity NPD3225 Approved
0.698 Remote Similarity NPD8651 Approved
0.6978 Remote Similarity NPD2684 Approved
0.6971 Remote Similarity NPD7251 Discontinued
0.697 Remote Similarity NPD7411 Suspended
0.6968 Remote Similarity NPD6353 Approved
0.6966 Remote Similarity NPD1894 Discontinued
0.6964 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6964 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7833 Phase 2
0.6964 Remote Similarity NPD7831 Phase 2
0.6959 Remote Similarity NPD1608 Approved
0.6959 Remote Similarity NPD3972 Approved
0.6957 Remote Similarity NPD4357 Discontinued
0.6954 Remote Similarity NPD3018 Phase 2
0.6954 Remote Similarity NPD2861 Phase 2
0.6954 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6946 Remote Similarity NPD5353 Approved
0.6946 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6933 Remote Similarity NPD5403 Approved
0.6933 Remote Similarity NPD3266 Approved
0.6933 Remote Similarity NPD6362 Approved
0.6933 Remote Similarity NPD3267 Approved
0.6928 Remote Similarity NPD6801 Discontinued
0.6928 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6918 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6918 Remote Similarity NPD1652 Phase 2
0.6914 Remote Similarity NPD5401 Approved
0.6914 Remote Similarity NPD6797 Phase 2
0.6913 Remote Similarity NPD2983 Phase 2
0.6913 Remote Similarity NPD2982 Phase 2
0.6903 Remote Similarity NPD230 Phase 1
0.6903 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6898 Remote Similarity NPD7680 Approved
0.6894 Remote Similarity NPD7440 Discontinued
0.6894 Remote Similarity NPD7236 Approved
0.6892 Remote Similarity NPD3705 Approved
0.6887 Remote Similarity NPD2798 Approved
0.6887 Remote Similarity NPD4624 Approved
0.6886 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6331 Phase 2
0.6875 Remote Similarity NPD3750 Approved
0.6875 Remote Similarity NPD7982 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6559 Discontinued
0.6872 Remote Similarity NPD8150 Discontinued
0.6871 Remote Similarity NPD6516 Phase 2
0.6871 Remote Similarity NPD7526 Approved
0.6871 Remote Similarity NPD52 Approved
0.6871 Remote Similarity NPD5846 Approved
0.6871 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6867 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6865 Remote Similarity NPD7237 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