Structure

Physi-Chem Properties

Molecular Weight:  252.12
Volume:  281.964
LogP:  3.781
LogD:  3.545
LogS:  -2.951
# Rotatable Bonds:  4
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.805
Synthetic Accessibility Score:  2.92
Fsp3:  0.059
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.722
MDCK Permeability:  1.4058059605304152e-05
Pgp-inhibitor:  0.104
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.082
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.047
Plasma Protein Binding (PPB):  99.51065826416016%
Volume Distribution (VD):  0.547
Pgp-substrate:  0.7881879806518555%

ADMET: Metabolism

CYP1A2-inhibitor:  0.952
CYP1A2-substrate:  0.284
CYP2C19-inhibitor:  0.798
CYP2C19-substrate:  0.086
CYP2C9-inhibitor:  0.698
CYP2C9-substrate:  0.963
CYP2D6-inhibitor:  0.826
CYP2D6-substrate:  0.882
CYP3A4-inhibitor:  0.739
CYP3A4-substrate:  0.305

ADMET: Excretion

Clearance (CL):  6.44
Half-life (T1/2):  0.852

ADMET: Toxicity

hERG Blockers:  0.154
Human Hepatotoxicity (H-HT):  0.273
Drug-inuced Liver Injury (DILI):  0.032
AMES Toxicity:  0.496
Rat Oral Acute Toxicity:  0.57
Maximum Recommended Daily Dose:  0.918
Skin Sensitization:  0.838
Carcinogencity:  0.138
Eye Corrosion:  0.004
Eye Irritation:  0.286
Respiratory Toxicity:  0.91

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

  Natural Product: NPC132271

Natural Product ID:  NPC132271
Common Name*:   (+)-Hinokiresinol
IUPAC Name:   4-[(1E,3R)-3-(4-hydroxyphenyl)penta-1,4-dienyl]phenol
Synonyms:   (+)-Hinokiresinol
Standard InCHIKey:  VEAUNWQYYMXIRB-BOTMBNHJSA-N
Standard InCHI:  InChI=1S/C17H16O2/c1-2-14(15-7-11-17(19)12-8-15)6-3-13-4-9-16(18)10-5-13/h2-12,14,18-19H,1H2/b6-3+/t14-/m1/s1
SMILES:  C=C[C@@H](c1ccc(cc1)O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL199799
PubChem CID:   6438674
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
NPO11694 Asparagus cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[14987058]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota rhizomes n.a. n.a. PMID[19757853]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. rhizome n.a. PMID[21370894]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota Rhizomes n.a. n.a. PMID[8482946]
NPO11694 Asparagus cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11694 Asparagus cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11694 Asparagus cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11694 Asparagus cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26741 Anemarrhena asphodeloides Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11694 Asparagus cochinchinensis Species Asparagaceae 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 14.0 ug.mL-1 PMID[471439]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 55000.0 nM PMID[471440]

☑ 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 NPC132271 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
1.0 High Similarity NPC82664
1.0 High Similarity NPC292730
1.0 High Similarity NPC216520
0.9565 High Similarity NPC473388
0.956 High Similarity NPC151715
0.9457 High Similarity NPC26244
0.9362 High Similarity NPC92730
0.9341 High Similarity NPC45040
0.9271 High Similarity NPC168829
0.9255 High Similarity NPC225464
0.9247 High Similarity NPC274678
0.9175 High Similarity NPC288411
0.9158 High Similarity NPC216468
0.9158 High Similarity NPC78119
0.9158 High Similarity NPC51333
0.9158 High Similarity NPC132078
0.914 High Similarity NPC128062
0.914 High Similarity NPC76938
0.913 High Similarity NPC304541
0.9082 High Similarity NPC138942
0.9062 High Similarity NPC213730
0.9043 High Similarity NPC32714
0.9 High Similarity NPC11554
0.9 High Similarity NPC201959
0.899 High Similarity NPC271274
0.898 High Similarity NPC323810
0.8969 High Similarity NPC40258
0.8969 High Similarity NPC7686
0.8969 High Similarity NPC91461
0.8936 High Similarity NPC316301
0.8936 High Similarity NPC27323
0.8925 High Similarity NPC155908
0.8913 High Similarity NPC318325
0.8913 High Similarity NPC258219
0.8913 High Similarity NPC280347
0.8913 High Similarity NPC242240
0.8913 High Similarity NPC177420
0.8913 High Similarity NPC123273
0.8911 High Similarity NPC228343
0.8911 High Similarity NPC254833
0.8889 High Similarity NPC175313
0.8889 High Similarity NPC239291
0.8866 High Similarity NPC294741
0.8854 High Similarity NPC77492
0.8854 High Similarity NPC32674
0.8854 High Similarity NPC201967
0.883 High Similarity NPC271440
0.8824 High Similarity NPC296683
0.8817 High Similarity NPC55561
0.8817 High Similarity NPC192
0.8812 High Similarity NPC262365
0.8804 High Similarity NPC25493
0.8804 High Similarity NPC113460
0.88 High Similarity NPC248904
0.8791 High Similarity NPC197783
0.8788 High Similarity NPC120693
0.8788 High Similarity NPC261573
0.8788 High Similarity NPC8931
0.8778 High Similarity NPC265146
0.8776 High Similarity NPC12221
0.8763 High Similarity NPC130193
0.8723 High Similarity NPC270547
0.871 High Similarity NPC98772
0.87 High Similarity NPC154899
0.87 High Similarity NPC233396
0.87 High Similarity NPC474839
0.8696 High Similarity NPC184169
0.8696 High Similarity NPC23167
0.8687 High Similarity NPC135784
0.8681 High Similarity NPC248817
0.8673 High Similarity NPC225506
0.8646 High Similarity NPC8392
0.8641 High Similarity NPC44732
0.8632 High Similarity NPC210497
0.8632 High Similarity NPC94139
0.8632 High Similarity NPC3358
0.8632 High Similarity NPC306884
0.8632 High Similarity NPC147284
0.8632 High Similarity NPC162314
0.8617 High Similarity NPC300017
0.8614 High Similarity NPC54765
0.8614 High Similarity NPC188677
0.8614 High Similarity NPC113457
0.8614 High Similarity NPC92623
0.8614 High Similarity NPC135464
0.8602 High Similarity NPC104216
0.86 High Similarity NPC119860
0.86 High Similarity NPC241891
0.86 High Similarity NPC327811
0.86 High Similarity NPC471511
0.86 High Similarity NPC254965
0.86 High Similarity NPC30506
0.8586 High Similarity NPC51015
0.8571 High Similarity NPC124436
0.8571 High Similarity NPC176730
0.8571 High Similarity NPC252821
0.8571 High Similarity NPC122005
0.8571 High Similarity NPC123175
0.8558 High Similarity NPC308689
0.8558 High Similarity NPC95716
0.8544 High Similarity NPC55617
0.8544 High Similarity NPC58865
0.8544 High Similarity NPC62258
0.8542 High Similarity NPC152415
0.8529 High Similarity NPC320439
0.8529 High Similarity NPC151477
0.8515 High Similarity NPC99557
0.8515 High Similarity NPC219286
0.8515 High Similarity NPC134829
0.85 High Similarity NPC68269
0.8491 Intermediate Similarity NPC120280
0.8485 Intermediate Similarity NPC72729
0.8485 Intermediate Similarity NPC223393
0.8485 Intermediate Similarity NPC161571
0.8485 Intermediate Similarity NPC275053
0.8485 Intermediate Similarity NPC248573
0.8476 Intermediate Similarity NPC46940
0.8476 Intermediate Similarity NPC228425
0.8476 Intermediate Similarity NPC228988
0.8476 Intermediate Similarity NPC286222
0.8469 Intermediate Similarity NPC79241
0.8469 Intermediate Similarity NPC6597
0.8469 Intermediate Similarity NPC156313
0.8462 Intermediate Similarity NPC174096
0.8462 Intermediate Similarity NPC147634
0.8462 Intermediate Similarity NPC226401
0.8462 Intermediate Similarity NPC120982
0.8462 Intermediate Similarity NPC13482
0.8462 Intermediate Similarity NPC79793
0.8447 Intermediate Similarity NPC95344
0.8447 Intermediate Similarity NPC61885
0.8447 Intermediate Similarity NPC63698
0.8447 Intermediate Similarity NPC75440
0.8438 Intermediate Similarity NPC325292
0.8438 Intermediate Similarity NPC138117
0.8438 Intermediate Similarity NPC55903
0.8431 Intermediate Similarity NPC95178
0.8431 Intermediate Similarity NPC302681
0.8431 Intermediate Similarity NPC39097
0.8431 Intermediate Similarity NPC69332
0.8431 Intermediate Similarity NPC477814
0.8431 Intermediate Similarity NPC70843
0.8431 Intermediate Similarity NPC39664
0.8431 Intermediate Similarity NPC109691
0.8431 Intermediate Similarity NPC118286
0.8431 Intermediate Similarity NPC29989
0.8431 Intermediate Similarity NPC470700
0.8411 Intermediate Similarity NPC322197
0.8404 Intermediate Similarity NPC27974
0.84 Intermediate Similarity NPC100340
0.84 Intermediate Similarity NPC143659
0.84 Intermediate Similarity NPC101025
0.84 Intermediate Similarity NPC471578
0.8396 Intermediate Similarity NPC715
0.8396 Intermediate Similarity NPC141003
0.8396 Intermediate Similarity NPC35344
0.8387 Intermediate Similarity NPC155393
0.8384 Intermediate Similarity NPC128723
0.8384 Intermediate Similarity NPC275104
0.8381 Intermediate Similarity NPC322753
0.8381 Intermediate Similarity NPC257430
0.8381 Intermediate Similarity NPC476632
0.8381 Intermediate Similarity NPC151537
0.8381 Intermediate Similarity NPC225679
0.8381 Intermediate Similarity NPC165770
0.8381 Intermediate Similarity NPC187583
0.8381 Intermediate Similarity NPC224527
0.8381 Intermediate Similarity NPC4493
0.8381 Intermediate Similarity NPC179002
0.8367 Intermediate Similarity NPC312132
0.8367 Intermediate Similarity NPC259512
0.8367 Intermediate Similarity NPC202986
0.8365 Intermediate Similarity NPC306045
0.8365 Intermediate Similarity NPC88141
0.8365 Intermediate Similarity NPC265211
0.835 Intermediate Similarity NPC54844
0.8333 Intermediate Similarity NPC246056
0.8333 Intermediate Similarity NPC306074
0.8333 Intermediate Similarity NPC117115
0.8333 Intermediate Similarity NPC204210
0.8318 Intermediate Similarity NPC195922
0.8318 Intermediate Similarity NPC473137
0.8318 Intermediate Similarity NPC107240
0.8318 Intermediate Similarity NPC12656
0.8317 Intermediate Similarity NPC62351
0.8317 Intermediate Similarity NPC196479
0.8317 Intermediate Similarity NPC233827
0.8317 Intermediate Similarity NPC168393
0.8302 Intermediate Similarity NPC250323
0.8302 Intermediate Similarity NPC166995
0.8302 Intermediate Similarity NPC43525
0.83 Intermediate Similarity NPC10588
0.83 Intermediate Similarity NPC48730
0.83 Intermediate Similarity NPC248396
0.83 Intermediate Similarity NPC129373
0.83 Intermediate Similarity NPC211885
0.8298 Intermediate Similarity NPC307235
0.8298 Intermediate Similarity NPC407
0.8286 Intermediate Similarity NPC252544
0.8286 Intermediate Similarity NPC321252

  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 NPC132271 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
0.9783 High Similarity NPD3020 Approved
0.9457 High Similarity NPD2860 Approved
0.9457 High Similarity NPD2859 Approved
0.9348 High Similarity NPD2934 Approved
0.9348 High Similarity NPD2933 Approved
0.8936 High Similarity NPD1432 Clinical (unspecified phase)
0.8911 High Similarity NPD3021 Approved
0.8911 High Similarity NPD3022 Approved
0.8571 High Similarity NPD111 Approved
0.8485 Intermediate Similarity NPD1242 Phase 1
0.8438 Intermediate Similarity NPD845 Approved
0.8396 Intermediate Similarity NPD2234 Approved
0.8396 Intermediate Similarity NPD2228 Approved
0.8396 Intermediate Similarity NPD2229 Approved
0.8367 Intermediate Similarity NPD288 Approved
0.8265 Intermediate Similarity NPD1809 Phase 2
0.8265 Intermediate Similarity NPD844 Approved
0.8218 Intermediate Similarity NPD940 Approved
0.8218 Intermediate Similarity NPD846 Approved
0.8131 Intermediate Similarity NPD7635 Approved
0.8119 Intermediate Similarity NPD3028 Approved
0.8119 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.8019 Intermediate Similarity NPD1792 Phase 2
0.8019 Intermediate Similarity NPD4750 Phase 3
0.8018 Intermediate Similarity NPD3091 Approved
0.8 Intermediate Similarity NPD2342 Discontinued
0.7946 Intermediate Similarity NPD4093 Discontinued
0.7905 Intermediate Similarity NPD1444 Approved
0.7905 Intermediate Similarity NPD1445 Approved
0.7876 Intermediate Similarity NPD4059 Approved
0.7876 Intermediate Similarity NPD3019 Approved
0.7876 Intermediate Similarity NPD2932 Approved
0.7857 Intermediate Similarity NPD5303 Approved
0.7857 Intermediate Similarity NPD5304 Approved
0.7759 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7739 Intermediate Similarity NPD3092 Approved
0.7727 Intermediate Similarity NPD5283 Phase 1
0.7719 Intermediate Similarity NPD4589 Approved
0.7719 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD2286 Discontinued
0.7658 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD1610 Phase 2
0.757 Intermediate Similarity NPD968 Approved
0.7565 Intermediate Similarity NPD2668 Approved
0.7565 Intermediate Similarity NPD3095 Discontinued
0.7565 Intermediate Similarity NPD2667 Approved
0.7565 Intermediate Similarity NPD1751 Approved
0.7556 Intermediate Similarity NPD9087 Approved
0.7547 Intermediate Similarity NPD9608 Approved
0.7547 Intermediate Similarity NPD9610 Approved
0.7545 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7523 Intermediate Similarity NPD5451 Approved
0.7522 Intermediate Similarity NPD7325 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2861 Phase 2
0.7479 Intermediate Similarity NPD3094 Phase 2
0.7479 Intermediate Similarity NPD4339 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD4659 Approved
0.7453 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD4908 Phase 1
0.7436 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD6671 Approved
0.7431 Intermediate Similarity NPD2684 Approved
0.7419 Intermediate Similarity NPD9088 Approved
0.7411 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7387 Intermediate Similarity NPD228 Approved
0.7364 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD5736 Approved
0.735 Intermediate Similarity NPD3421 Phase 3
0.7345 Intermediate Similarity NPD475 Phase 2
0.7333 Intermediate Similarity NPD4103 Phase 2
0.7333 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD9379 Approved
0.7321 Intermediate Similarity NPD5535 Approved
0.7321 Intermediate Similarity NPD9377 Approved
0.7317 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD6583 Phase 3
0.7311 Intermediate Similarity NPD6582 Phase 2
0.729 Intermediate Similarity NPD9500 Approved
0.7281 Intermediate Similarity NPD7157 Approved
0.7273 Intermediate Similarity NPD6584 Phase 3
0.7273 Intermediate Similarity NPD2195 Approved
0.7273 Intermediate Similarity NPD2194 Approved
0.725 Intermediate Similarity NPD5311 Approved
0.725 Intermediate Similarity NPD5310 Approved
0.7241 Intermediate Similarity NPD7330 Discontinued
0.7241 Intermediate Similarity NPD1548 Phase 1
0.7241 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD9273 Approved
0.7236 Intermediate Similarity NPD5155 Approved
0.7236 Intermediate Similarity NPD5156 Approved
0.7227 Intermediate Similarity NPD2230 Approved
0.7227 Intermediate Similarity NPD2233 Approved
0.7227 Intermediate Similarity NPD2561 Approved
0.7227 Intermediate Similarity NPD2562 Approved
0.7227 Intermediate Similarity NPD2232 Approved
0.7213 Intermediate Similarity NPD3636 Approved
0.7213 Intermediate Similarity NPD3635 Approved
0.7213 Intermediate Similarity NPD3637 Approved
0.7203 Intermediate Similarity NPD3847 Discontinued
0.7203 Intermediate Similarity NPD3023 Approved
0.7203 Intermediate Similarity NPD3026 Approved
0.72 Intermediate Similarity NPD4060 Phase 1
0.7196 Intermediate Similarity NPD4817 Approved
0.7196 Intermediate Similarity NPD4818 Approved
0.7193 Intermediate Similarity NPD1791 Approved
0.7193 Intermediate Similarity NPD1793 Approved
0.719 Intermediate Similarity NPD3055 Approved
0.719 Intermediate Similarity NPD1164 Approved
0.719 Intermediate Similarity NPD3053 Approved
0.7179 Intermediate Similarity NPD3025 Approved
0.7179 Intermediate Similarity NPD3024 Approved
0.7168 Intermediate Similarity NPD7843 Approved
0.7167 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD2606 Approved
0.7154 Intermediate Similarity NPD3594 Approved
0.7154 Intermediate Similarity NPD3595 Approved
0.7154 Intermediate Similarity NPD2605 Approved
0.7143 Intermediate Similarity NPD1201 Approved
0.7131 Intermediate Similarity NPD4624 Approved
0.713 Intermediate Similarity NPD4656 Approved
0.713 Intermediate Similarity NPD256 Approved
0.713 Intermediate Similarity NPD255 Approved
0.713 Intermediate Similarity NPD4229 Approved
0.713 Intermediate Similarity NPD4231 Approved
0.713 Intermediate Similarity NPD3680 Approved
0.713 Intermediate Similarity NPD3682 Approved
0.713 Intermediate Similarity NPD4658 Approved
0.7128 Intermediate Similarity NPD9294 Approved
0.712 Intermediate Similarity NPD6663 Approved
0.7119 Intermediate Similarity NPD4626 Approved
0.7119 Intermediate Similarity NPD6516 Phase 2
0.7119 Intermediate Similarity NPD5846 Approved
0.7113 Intermediate Similarity NPD9089 Approved
0.7107 Intermediate Similarity NPD1283 Approved
0.7103 Intermediate Similarity NPD1616 Discontinued
0.7097 Intermediate Similarity NPD3027 Phase 3
0.7091 Intermediate Similarity NPD3134 Approved
0.7083 Intermediate Similarity NPD2337 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD2797 Approved
0.7043 Intermediate Similarity NPD497 Approved
0.704 Intermediate Similarity NPD3764 Approved
0.7034 Intermediate Similarity NPD4235 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD1651 Approved
0.7034 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD1669 Approved
0.7025 Intermediate Similarity NPD4749 Approved
0.7018 Intermediate Similarity NPD821 Approved
0.701 Intermediate Similarity NPD9093 Approved
0.7009 Intermediate Similarity NPD16 Approved
0.7009 Intermediate Similarity NPD856 Approved
0.7 Intermediate Similarity NPD1535 Discovery
0.6992 Remote Similarity NPD7451 Discontinued
0.6991 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6984 Remote Similarity NPD6405 Approved
0.6984 Remote Similarity NPD6407 Approved
0.6983 Remote Similarity NPD6387 Discontinued
0.6983 Remote Similarity NPD709 Approved
0.6972 Remote Similarity NPD3681 Approved
0.6972 Remote Similarity NPD3683 Approved
0.696 Remote Similarity NPD4625 Phase 3
0.696 Remote Similarity NPD7095 Approved
0.6957 Remote Similarity NPD496 Approved
0.6957 Remote Similarity NPD498 Approved
0.6957 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6957 Remote Similarity NPD495 Approved
0.6949 Remote Similarity NPD1894 Discontinued
0.6942 Remote Similarity NPD1481 Phase 2
0.6942 Remote Similarity NPD2235 Phase 2
0.6942 Remote Similarity NPD1608 Approved
0.6942 Remote Similarity NPD2231 Phase 2
0.6929 Remote Similarity NPD3620 Phase 2
0.6929 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6929 Remote Similarity NPD6346 Approved
0.6923 Remote Similarity NPD9568 Approved
0.6923 Remote Similarity NPD3596 Phase 2
0.6923 Remote Similarity NPD405 Clinical (unspecified phase)
0.6917 Remote Similarity NPD1981 Approved
0.6917 Remote Similarity NPD1983 Approved
0.6917 Remote Similarity NPD3143 Discontinued
0.6917 Remote Similarity NPD1980 Approved
0.6911 Remote Similarity NPD1470 Approved
0.6897 Remote Similarity NPD9614 Approved
0.6897 Remote Similarity NPD9618 Approved
0.6885 Remote Similarity NPD5327 Phase 3
0.6885 Remote Similarity NPD1755 Approved
0.688 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4095 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6355 Discontinued
0.6864 Remote Similarity NPD317 Approved
0.6864 Remote Similarity NPD5536 Phase 2
0.6864 Remote Similarity NPD318 Approved
0.686 Remote Similarity NPD1281 Approved
0.6855 Remote Similarity NPD2798 Approved
0.6846 Remote Similarity NPD7742 Approved
0.6846 Remote Similarity NPD7743 Approved
0.6833 Remote Similarity NPD9381 Approved
0.6833 Remote Similarity NPD9384 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
A: chemistry similarity;
B: biological targets similarity;
C: networks similarity;
D: cell-based bioactivity similarity;
E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data