Structure

Physi-Chem Properties

Molecular Weight:  538.22
Volume:  551.878
LogP:  3.872
LogD:  3.599
LogS:  -4.565
# Rotatable Bonds:  14
TPSA:  134.91
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.187
Synthetic Accessibility Score:  3.465
Fsp3:  0.3
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.135
MDCK Permeability:  8.169082320819143e-06
Pgp-inhibitor:  0.345
Pgp-substrate:  0.837
Human Intestinal Absorption (HIA):  0.031
20% Bioavailability (F20%):  0.744
30% Bioavailability (F30%):  0.105

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.038
Plasma Protein Binding (PPB):  100.27642059326172%
Volume Distribution (VD):  0.407
Pgp-substrate:  1.108656883239746%

ADMET: Metabolism

CYP1A2-inhibitor:  0.499
CYP1A2-substrate:  0.931
CYP2C19-inhibitor:  0.667
CYP2C19-substrate:  0.211
CYP2C9-inhibitor:  0.842
CYP2C9-substrate:  0.906
CYP2D6-inhibitor:  0.616
CYP2D6-substrate:  0.927
CYP3A4-inhibitor:  0.646
CYP3A4-substrate:  0.888

ADMET: Excretion

Clearance (CL):  11.664
Half-life (T1/2):  0.923

ADMET: Toxicity

hERG Blockers:  0.383
Human Hepatotoxicity (H-HT):  0.256
Drug-inuced Liver Injury (DILI):  0.253
AMES Toxicity:  0.047
Rat Oral Acute Toxicity:  0.053
Maximum Recommended Daily Dose:  0.895
Skin Sensitization:  0.963
Carcinogencity:  0.099
Eye Corrosion:  0.003
Eye Irritation:  0.338
Respiratory Toxicity:  0.41

Download Data

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

  Natural Product: NPC120852

Natural Product ID:  NPC120852
Common Name*:   Hanultarin
IUPAC Name:   [(2R,3R)-4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:   Hanultarin
Standard InCHIKey:  YXLRFCDMMBITIW-ZDRWSHPDSA-N
Standard InCHI:  InChI=1S/C30H34O9/c1-36-27-14-19(4-8-24(27)32)7-11-30(35)39-18-23(13-21-6-10-26(34)29(16-21)38-3)22(17-31)12-20-5-9-25(33)28(15-20)37-2/h4-11,14-16,22-23,31-34H,12-13,17-18H2,1-3H3/b11-7+/t22-,23-/m0/s1
SMILES:  COc1cc(ccc1O)/C=C/C(=O)OC[C@H](Cc1ccc(c(c1)OC)O)[C@@H](Cc1ccc(c(c1)OC)O)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479034
PubChem CID:   25147697
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001969] Dibenzylbutane lignans

*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
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. seed n.a. DOI[10.1016/S0031-9422(00)97029-8]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota seeds n.a. n.a. PMID[18603435]
NPO8089 Hypericum chinense Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[19606850]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota Seeds n.a. n.a. PMID[20469887]
NPO8089 Hypericum chinense Species Hypericaceae Eukaryota n.a. root n.a. PMID[21043475]
NPO8089 Hypericum chinense Species Hypericaceae Eukaryota n.a. leaf n.a. PMID[21043475]
NPO8089 Hypericum chinense Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[22074257]
NPO8089 Hypericum chinense Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8089 Hypericum chinense Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8089 Hypericum chinense Species Hypericaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 = 3.0 ug.mL-1 PMID[506966]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 3.0 ug.mL-1 PMID[506966]
NPT407 Cell Line COLO 205 Homo sapiens IC50 = 16.8 ug.mL-1 PMID[506967]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 18.9 ug.mL-1 PMID[506967]
NPT111 Cell Line K562 Homo sapiens IC50 = 33.1 ug.mL-1 PMID[506967]
NPT91 Cell Line KB Homo sapiens IC50 = 33.7 ug.mL-1 PMID[506967]
NPT111 Cell Line K562 Homo sapiens IC50 = 35.2 ug.mL-1 PMID[506967]
NPT81 Cell Line A549 Homo sapiens IC50 = 29500.0 nM PMID[506968]
NPT169 Cell Line B16-F10 Mus musculus IC50 = 21400.0 nM PMID[506968]
NPT148 Cell Line HCT-15 Homo sapiens IC50 = 29300.0 nM PMID[506968]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 63900.0 nM PMID[506968]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 17300.0 nM PMID[506968]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 13.0 ug.mL-1 PMID[506966]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 20.7 ug.mL-1 PMID[506967]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 20.9 ug.mL-1 PMID[506967]

☑ 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 NPC120852 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
0.9624 High Similarity NPC110699
0.9624 High Similarity NPC106055
0.9338 High Similarity NPC67467
0.9308 High Similarity NPC83062
0.9225 High Similarity NPC213552
0.9225 High Similarity NPC120225
0.9147 High Similarity NPC289459
0.9118 High Similarity NPC132723
0.9118 High Similarity NPC76032
0.9104 High Similarity NPC135127
0.9078 High Similarity NPC102934
0.9078 High Similarity NPC252402
0.907 High Similarity NPC246704
0.907 High Similarity NPC20443
0.907 High Similarity NPC146886
0.907 High Similarity NPC60517
0.9 High Similarity NPC473909
0.9 High Similarity NPC143120
0.9 High Similarity NPC274960
0.8958 High Similarity NPC478268
0.8915 High Similarity NPC85488
0.8905 High Similarity NPC126206
0.8897 High Similarity NPC113295
0.8846 High Similarity NPC280704
0.8837 High Similarity NPC70752
0.8832 High Similarity NPC77861
0.8832 High Similarity NPC471664
0.8832 High Similarity NPC471988
0.8832 High Similarity NPC90431
0.8832 High Similarity NPC471665
0.8824 High Similarity NPC67247
0.8797 High Similarity NPC110313
0.8797 High Similarity NPC307050
0.8797 High Similarity NPC478215
0.8797 High Similarity NPC277458
0.8786 High Similarity NPC140502
0.8768 High Similarity NPC281780
0.8767 High Similarity NPC475141
0.8767 High Similarity NPC115203
0.876 High Similarity NPC204466
0.875 High Similarity NPC475250
0.8732 High Similarity NPC34587
0.8732 High Similarity NPC19862
0.8732 High Similarity NPC271607
0.8732 High Similarity NPC307205
0.8732 High Similarity NPC163898
0.8732 High Similarity NPC34927
0.8732 High Similarity NPC476382
0.8732 High Similarity NPC235195
0.8732 High Similarity NPC100998
0.8732 High Similarity NPC280717
0.8732 High Similarity NPC252292
0.8716 High Similarity NPC11411
0.8707 High Similarity NPC473736
0.8702 High Similarity NPC317769
0.8702 High Similarity NPC31344
0.8699 High Similarity NPC267091
0.8699 High Similarity NPC476434
0.869 High Similarity NPC208785
0.869 High Similarity NPC145527
0.869 High Similarity NPC470618
0.869 High Similarity NPC470619
0.8686 High Similarity NPC4982
0.8686 High Similarity NPC5310
0.8686 High Similarity NPC68779
0.8686 High Similarity NPC176814
0.8686 High Similarity NPC300776
0.8682 High Similarity NPC227217
0.8682 High Similarity NPC95614
0.8682 High Similarity NPC232316
0.8682 High Similarity NPC202474
0.8682 High Similarity NPC165133
0.8682 High Similarity NPC242885
0.8682 High Similarity NPC56214
0.8682 High Similarity NPC117780
0.8667 High Similarity NPC173308
0.8667 High Similarity NPC181079
0.8662 High Similarity NPC471876
0.8652 High Similarity NPC472410
0.8643 High Similarity NPC266197
0.8643 High Similarity NPC291101
0.863 High Similarity NPC243891
0.8623 High Similarity NPC93783
0.8621 High Similarity NPC273358
0.8621 High Similarity NPC298647
0.8615 High Similarity NPC470848
0.8615 High Similarity NPC60962
0.8615 High Similarity NPC470849
0.8615 High Similarity NPC109083
0.8615 High Similarity NPC189844
0.8615 High Similarity NPC224814
0.8615 High Similarity NPC269843
0.8615 High Similarity NPC14007
0.8615 High Similarity NPC207613
0.8613 High Similarity NPC475468
0.8611 High Similarity NPC232992
0.8605 High Similarity NPC310338
0.8605 High Similarity NPC281298
0.8605 High Similarity NPC263386
0.8605 High Similarity NPC141791
0.8603 High Similarity NPC476345
0.86 High Similarity NPC478269
0.8593 High Similarity NPC475875
0.8592 High Similarity NPC478239
0.8582 High Similarity NPC5428
0.8582 High Similarity NPC165045
0.8582 High Similarity NPC118533
0.8582 High Similarity NPC29599
0.8582 High Similarity NPC470372
0.8582 High Similarity NPC100675
0.8571 High Similarity NPC29008
0.8571 High Similarity NPC87113
0.8571 High Similarity NPC266705
0.8571 High Similarity NPC228771
0.8571 High Similarity NPC148627
0.8552 High Similarity NPC201148
0.8552 High Similarity NPC96930
0.8552 High Similarity NPC199311
0.8552 High Similarity NPC28651
0.8552 High Similarity NPC192763
0.8552 High Similarity NPC215095
0.8552 High Similarity NPC261122
0.8552 High Similarity NPC300262
0.8552 High Similarity NPC3460
0.8552 High Similarity NPC32017
0.8552 High Similarity NPC80732
0.8552 High Similarity NPC210611
0.8551 High Similarity NPC476387
0.8551 High Similarity NPC119060
0.8551 High Similarity NPC471110
0.8551 High Similarity NPC249791
0.8551 High Similarity NPC237594
0.855 High Similarity NPC324571
0.855 High Similarity NPC54872
0.855 High Similarity NPC470212
0.855 High Similarity NPC38996
0.855 High Similarity NPC473853
0.855 High Similarity NPC113865
0.855 High Similarity NPC312675
0.855 High Similarity NPC262156
0.855 High Similarity NPC184651
0.855 High Similarity NPC160380
0.855 High Similarity NPC343720
0.8542 High Similarity NPC40222
0.8542 High Similarity NPC268515
0.8538 High Similarity NPC2058
0.8533 High Similarity NPC125495
0.8531 High Similarity NPC160378
0.8531 High Similarity NPC110063
0.8529 High Similarity NPC242807
0.8529 High Similarity NPC275950
0.8529 High Similarity NPC64201
0.8529 High Similarity NPC187998
0.8529 High Similarity NPC153739
0.8529 High Similarity NPC257582
0.8529 High Similarity NPC77040
0.8529 High Similarity NPC145305
0.8529 High Similarity NPC42300
0.8529 High Similarity NPC174495
0.8529 High Similarity NPC241522
0.8529 High Similarity NPC92164
0.8527 High Similarity NPC137537
0.8527 High Similarity NPC275519
0.8527 High Similarity NPC107588
0.8527 High Similarity NPC277460
0.8527 High Similarity NPC203124
0.8527 High Similarity NPC70744
0.8527 High Similarity NPC470626
0.8527 High Similarity NPC474040
0.8527 High Similarity NPC164706
0.8527 High Similarity NPC272471
0.8523 High Similarity NPC131532
0.8521 High Similarity NPC52664
0.8521 High Similarity NPC131971
0.8521 High Similarity NPC157816
0.8519 High Similarity NPC252307
0.8519 High Similarity NPC282703
0.8519 High Similarity NPC128208
0.8519 High Similarity NPC45774
0.8519 High Similarity NPC11258
0.8519 High Similarity NPC245826
0.8519 High Similarity NPC21867
0.8519 High Similarity NPC129570
0.8519 High Similarity NPC474178
0.8519 High Similarity NPC184733
0.8514 High Similarity NPC470769
0.8511 High Similarity NPC288452
0.8511 High Similarity NPC289690
0.8507 High Similarity NPC118584
0.8507 High Similarity NPC17837
0.8507 High Similarity NPC304630
0.8507 High Similarity NPC276014
0.8503 High Similarity NPC118033
0.8493 Intermediate Similarity NPC292206
0.8493 Intermediate Similarity NPC306890
0.8493 Intermediate Similarity NPC476398
0.8493 Intermediate Similarity NPC259347
0.8493 Intermediate Similarity NPC471062
0.8493 Intermediate Similarity NPC474347
0.8493 Intermediate Similarity NPC470933

  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 NPC120852 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
0.8421 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.831 Intermediate Similarity NPD7266 Discontinued
0.8188 Intermediate Similarity NPD3027 Phase 3
0.8143 Intermediate Similarity NPD4060 Phase 1
0.814 Intermediate Similarity NPD5283 Phase 1
0.8058 Intermediate Similarity NPD7095 Approved
0.8014 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.8014 Intermediate Similarity NPD3620 Phase 2
0.8014 Intermediate Similarity NPD8166 Discontinued
0.7984 Intermediate Similarity NPD228 Approved
0.7973 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD5536 Phase 2
0.7871 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD6190 Approved
0.7829 Intermediate Similarity NPD3021 Approved
0.7829 Intermediate Similarity NPD3022 Approved
0.7785 Intermediate Similarity NPD8127 Discontinued
0.7771 Intermediate Similarity NPD6234 Discontinued
0.7763 Intermediate Similarity NPD1653 Approved
0.7762 Intermediate Similarity NPD1613 Approved
0.7762 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD6798 Discontinued
0.7744 Intermediate Similarity NPD7157 Approved
0.7708 Intermediate Similarity NPD6355 Discontinued
0.7692 Intermediate Similarity NPD6233 Phase 2
0.7677 Intermediate Similarity NPD37 Approved
0.7674 Intermediate Similarity NPD1358 Approved
0.7654 Intermediate Similarity NPD7228 Approved
0.7652 Intermediate Similarity NPD7843 Approved
0.7652 Intermediate Similarity NPD5535 Approved
0.7651 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD4110 Phase 3
0.7651 Intermediate Similarity NPD4628 Phase 3
0.7643 Intermediate Similarity NPD4965 Approved
0.7643 Intermediate Similarity NPD4967 Phase 2
0.7643 Intermediate Similarity NPD4966 Approved
0.7639 Intermediate Similarity NPD4140 Approved
0.7606 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD7097 Phase 1
0.7597 Intermediate Similarity NPD3134 Approved
0.7593 Intermediate Similarity NPD7473 Discontinued
0.7591 Intermediate Similarity NPD4626 Approved
0.7576 Intermediate Similarity NPD7685 Pre-registration
0.7562 Intermediate Similarity NPD7199 Phase 2
0.7536 Intermediate Similarity NPD3496 Discontinued
0.7535 Intermediate Similarity NPD9494 Approved
0.7535 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD6653 Approved
0.7531 Intermediate Similarity NPD6166 Phase 2
0.7531 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD5691 Approved
0.7516 Intermediate Similarity NPD6232 Discontinued
0.75 Intermediate Similarity NPD2935 Discontinued
0.75 Intermediate Similarity NPD5844 Phase 1
0.7483 Intermediate Similarity NPD4908 Phase 1
0.7481 Intermediate Similarity NPD2684 Approved
0.7471 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7467 Intermediate Similarity NPD6674 Discontinued
0.7465 Intermediate Similarity NPD6584 Phase 3
0.7464 Intermediate Similarity NPD6516 Phase 2
0.7464 Intermediate Similarity NPD5846 Approved
0.7452 Intermediate Similarity NPD1934 Approved
0.745 Intermediate Similarity NPD5763 Approved
0.745 Intermediate Similarity NPD5762 Approved
0.7413 Intermediate Similarity NPD2861 Phase 2
0.741 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD6273 Approved
0.7394 Intermediate Similarity NPD2797 Approved
0.7391 Intermediate Similarity NPD5585 Approved
0.7391 Intermediate Similarity NPD1357 Approved
0.7379 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD7458 Discontinued
0.7362 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD3817 Phase 2
0.7357 Intermediate Similarity NPD3705 Approved
0.7351 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD7074 Phase 3
0.7347 Intermediate Similarity NPD4340 Discontinued
0.7347 Intermediate Similarity NPD5735 Approved
0.7338 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD3818 Discontinued
0.7324 Intermediate Similarity NPD1283 Approved
0.7321 Intermediate Similarity NPD7549 Discontinued
0.7303 Intermediate Similarity NPD7003 Approved
0.7296 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD1465 Phase 2
0.7296 Intermediate Similarity NPD2801 Approved
0.7292 Intermediate Similarity NPD5736 Approved
0.7289 Intermediate Similarity NPD7054 Approved
0.7286 Intermediate Similarity NPD3847 Discontinued
0.7279 Intermediate Similarity NPD2979 Phase 3
0.7267 Intermediate Similarity NPD2438 Suspended
0.7261 Intermediate Similarity NPD3455 Phase 2
0.7261 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD3268 Approved
0.726 Intermediate Similarity NPD3764 Approved
0.7254 Intermediate Similarity NPD6582 Phase 2
0.7254 Intermediate Similarity NPD6583 Phase 3
0.7246 Intermediate Similarity NPD7472 Approved
0.7233 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD447 Suspended
0.723 Intermediate Similarity NPD230 Phase 1
0.7226 Intermediate Similarity NPD6671 Approved
0.7211 Intermediate Similarity NPD4062 Phase 3
0.7208 Intermediate Similarity NPD7440 Discontinued
0.7205 Intermediate Similarity NPD3882 Suspended
0.72 Intermediate Similarity NPD2799 Discontinued
0.719 Intermediate Similarity NPD6331 Phase 2
0.7188 Intermediate Similarity NPD8455 Phase 2
0.7183 Intermediate Similarity NPD1608 Approved
0.7181 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD6385 Approved
0.717 Intermediate Similarity NPD6386 Approved
0.717 Intermediate Similarity NPD6873 Phase 2
0.7164 Intermediate Similarity NPD5451 Approved
0.7162 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD1558 Phase 1
0.716 Intermediate Similarity NPD7039 Approved
0.716 Intermediate Similarity NPD7240 Approved
0.716 Intermediate Similarity NPD7075 Discontinued
0.716 Intermediate Similarity NPD7038 Approved
0.7152 Intermediate Similarity NPD6032 Approved
0.7143 Intermediate Similarity NPD5110 Phase 2
0.7143 Intermediate Similarity NPD5241 Discontinued
0.7143 Intermediate Similarity NPD5111 Phase 2
0.7143 Intermediate Similarity NPD5109 Approved
0.7133 Intermediate Similarity NPD4359 Approved
0.7133 Intermediate Similarity NPD2982 Phase 2
0.7133 Intermediate Similarity NPD2983 Phase 2
0.7133 Intermediate Similarity NPD5327 Phase 3
0.7132 Intermediate Similarity NPD3020 Approved
0.7124 Intermediate Similarity NPD5177 Phase 3
0.7124 Intermediate Similarity NPD3060 Approved
0.7123 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD3657 Discovery
0.7113 Intermediate Similarity NPD1281 Approved
0.7113 Intermediate Similarity NPD1610 Phase 2
0.7113 Intermediate Similarity NPD1535 Discovery
0.7107 Intermediate Similarity NPD4380 Phase 2
0.7107 Intermediate Similarity NPD7028 Phase 2
0.7101 Intermediate Similarity NPD4198 Discontinued
0.7099 Intermediate Similarity NPD7768 Phase 2
0.7095 Intermediate Similarity NPD2674 Phase 3
0.7095 Intermediate Similarity NPD6663 Approved
0.7095 Intermediate Similarity NPD8032 Phase 2
0.7089 Intermediate Similarity NPD3686 Approved
0.7089 Intermediate Similarity NPD3687 Approved
0.7086 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD8651 Approved
0.7081 Intermediate Similarity NPD7819 Suspended
0.7081 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD8313 Approved
0.7076 Intermediate Similarity NPD8312 Approved
0.7071 Intermediate Similarity NPD1894 Discontinued
0.7068 Intermediate Similarity NPD968 Approved
0.7063 Intermediate Similarity NPD2981 Phase 2
0.7063 Intermediate Similarity NPD1481 Phase 2
0.7059 Intermediate Similarity NPD7251 Discontinued
0.7059 Intermediate Similarity NPD4534 Discontinued
0.7059 Intermediate Similarity NPD5958 Discontinued
0.7055 Intermediate Similarity NPD3018 Phase 2
0.7051 Intermediate Similarity NPD1511 Approved
0.7035 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD987 Approved
0.7034 Intermediate Similarity NPD3094 Phase 2
0.7027 Intermediate Similarity NPD3144 Approved
0.7027 Intermediate Similarity NPD3145 Approved
0.7027 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD4538 Approved
0.702 Intermediate Similarity NPD6896 Approved
0.702 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD4536 Approved
0.702 Intermediate Similarity NPD6895 Approved
0.7018 Intermediate Similarity NPD7808 Phase 3
0.7013 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD1652 Phase 2
0.7013 Intermediate Similarity NPD4162 Approved
0.7007 Intermediate Similarity NPD6832 Phase 2
0.7006 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5124 Phase 1
0.7 Intermediate Similarity NPD6797 Phase 2
0.7 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1933 Approved
0.6993 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6993 Remote Similarity NPD2346 Discontinued
0.6993 Remote Similarity NPD1611 Approved
0.6993 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6993 Remote Similarity NPD422 Phase 1
0.6993 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6993 Remote Similarity NPD3092 Approved
0.6987 Remote Similarity NPD6667 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