Structure

Physi-Chem Properties

Molecular Weight:  712.25
Volume:  720.913
LogP:  6.026
LogD:  4.012
LogS:  -4.107
# Rotatable Bonds:  17
TPSA:  159.44
# H-Bond Aceptor:  12
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.07
Synthetic Accessibility Score:  3.943
Fsp3:  0.25
Lipinski Rule-of-5:  Rejected
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:  -5.402
MDCK Permeability:  3.880010262946598e-05
Pgp-inhibitor:  0.996
Pgp-substrate:  0.132
Human Intestinal Absorption (HIA):  0.031
20% Bioavailability (F20%):  0.997
30% Bioavailability (F30%):  0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  99.46562957763672%
Volume Distribution (VD):  0.352
Pgp-substrate:  3.7975502014160156%

ADMET: Metabolism

CYP1A2-inhibitor:  0.105
CYP1A2-substrate:  0.951
CYP2C19-inhibitor:  0.879
CYP2C19-substrate:  0.141
CYP2C9-inhibitor:  0.931
CYP2C9-substrate:  0.964
CYP2D6-inhibitor:  0.122
CYP2D6-substrate:  0.931
CYP3A4-inhibitor:  0.687
CYP3A4-substrate:  0.913

ADMET: Excretion

Clearance (CL):  9.11
Half-life (T1/2):  0.817

ADMET: Toxicity

hERG Blockers:  0.462
Human Hepatotoxicity (H-HT):  0.188
Drug-inuced Liver Injury (DILI):  0.535
AMES Toxicity:  0.555
Rat Oral Acute Toxicity:  0.141
Maximum Recommended Daily Dose:  0.928
Skin Sensitization:  0.976
Carcinogencity:  0.096
Eye Corrosion:  0.003
Eye Irritation:  0.072
Respiratory Toxicity:  0.513

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

  Natural Product: NPC115203

Natural Product ID:  NPC115203
Common Name*:   Boehmenan
IUPAC Name:   3-[(2R,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]propyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  OVFZHMPISOASDF-CIQYAKOOSA-N
Standard InCHI:  InChI=1S/C40H40O12/c1-46-33-19-24(7-12-30(33)41)9-15-37(44)50-17-5-6-26-18-28-29(23-51-38(45)16-10-25-8-13-31(42)34(20-25)47-2)39(52-40(28)36(21-26)49-4)27-11-14-32(43)35(22-27)48-3/h7-16,18-22,29,39,41-43H,5-6,17,23H2,1-4H3/b15-9+,16-10+/t29-,39+/m1/s1
SMILES:  COc1cc(ccc1O)/C=C/C(=O)OCCCc1cc2[C@@H](COC(=O)/C=C/c3ccc(c(c3)OC)O)[C@H](c3ccc(c(c3)OC)O)Oc2c(c1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3589242
PubChem CID:   5274624
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO10872 Aglaia ponapensis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[17055270]
NPO18913 Hibiscus ficulneus Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[26026364]
NPO27678 Boehmeria platanifolia Species Urticaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10872 Aglaia ponapensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5895 Hibiscus taiwanensis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5895 Hibiscus taiwanensis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27678 Boehmeria platanifolia Species Urticaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10872 Aglaia ponapensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23035 Clematis montana Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22589 Clematis armandii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10872 Aglaia ponapensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18913 Hibiscus ficulneus Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5895 Hibiscus taiwanensis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27678 Boehmeria platanifolia Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10510 Aconitum naviculare Species Ranunculaceae 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
NPT71 Cell Line HEK293 Homo sapiens IC50 = 1000.0 nM PMID[485991]
NPT71 Cell Line HEK293 Homo sapiens IC50 = 30300.0 nM PMID[485991]
NPT2170 Cell Line RKO Homo sapiens IC50 = 25400.0 nM PMID[485991]
NPT660 Cell Line SW480 Homo sapiens IC50 > 40000.0 nM PMID[485991]
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 22800.0 nM PMID[485991]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 40000.0 nM PMID[485991]

☑ 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 NPC115203 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
0.9732 High Similarity NPC125495
0.9412 High Similarity NPC216916
0.9408 High Similarity NPC478269
0.9342 High Similarity NPC470827
0.9315 High Similarity NPC163898
0.9315 High Similarity NPC143120
0.9315 High Similarity NPC274960
0.9315 High Similarity NPC473909
0.929 High Similarity NPC45943
0.9286 High Similarity NPC478267
0.9281 High Similarity NPC470828
0.9241 High Similarity NPC131971
0.9241 High Similarity NPC67467
0.9128 High Similarity NPC236166
0.9128 High Similarity NPC102934
0.9128 High Similarity NPC252402
0.9119 High Similarity NPC180768
0.9103 High Similarity NPC106055
0.9103 High Similarity NPC110699
0.9079 High Similarity NPC470769
0.9067 High Similarity NPC475250
0.9041 High Similarity NPC470372
0.9038 High Similarity NPC7191
0.9038 High Similarity NPC149873
0.9026 High Similarity NPC11411
0.9013 High Similarity NPC478268
0.8986 High Similarity NPC93433
0.8986 High Similarity NPC264706
0.8986 High Similarity NPC284881
0.8986 High Similarity NPC474444
0.8917 High Similarity NPC469889
0.8904 High Similarity NPC260842
0.8903 High Similarity NPC228357
0.8882 High Similarity NPC477612
0.8867 High Similarity NPC260397
0.8867 High Similarity NPC40222
0.8867 High Similarity NPC268515
0.8861 High Similarity NPC12326
0.8831 High Similarity NPC475141
0.8824 High Similarity NPC329343
0.8824 High Similarity NPC321972
0.8824 High Similarity NPC324517
0.8812 High Similarity NPC59516
0.88 High Similarity NPC181615
0.8774 High Similarity NPC157333
0.8774 High Similarity NPC469888
0.8774 High Similarity NPC473736
0.8774 High Similarity NPC268484
0.8773 High Similarity NPC316539
0.8767 High Similarity NPC209985
0.8767 High Similarity NPC120852
0.8767 High Similarity NPC156502
0.8767 High Similarity NPC10737
0.8767 High Similarity NPC471988
0.8767 High Similarity NPC263367
0.8767 High Similarity NPC54743
0.8767 High Similarity NPC477939
0.8767 High Similarity NPC77861
0.8767 High Similarity NPC177160
0.8767 High Similarity NPC29799
0.8759 High Similarity NPC67247
0.8759 High Similarity NPC187616
0.8759 High Similarity NPC193026
0.8759 High Similarity NPC49603
0.8758 High Similarity NPC208818
0.875 High Similarity NPC20757
0.875 High Similarity NPC304048
0.875 High Similarity NPC473408
0.875 High Similarity NPC227516
0.875 High Similarity NPC226153
0.871 High Similarity NPC223720
0.8707 High Similarity NPC126206
0.8707 High Similarity NPC281780
0.8704 High Similarity NPC186100
0.8704 High Similarity NPC216403
0.8704 High Similarity NPC41494
0.8701 High Similarity NPC143480
0.8701 High Similarity NPC7145
0.8701 High Similarity NPC125823
0.8701 High Similarity NPC85192
0.8699 High Similarity NPC93783
0.8693 High Similarity NPC470098
0.8693 High Similarity NPC470826
0.8693 High Similarity NPC211561
0.8693 High Similarity NPC473266
0.8684 High Similarity NPC15956
0.8684 High Similarity NPC224674
0.8684 High Similarity NPC328567
0.8684 High Similarity NPC99183
0.8684 High Similarity NPC327412
0.8684 High Similarity NPC193473
0.8684 High Similarity NPC114505
0.8684 High Similarity NPC320970
0.8684 High Similarity NPC213074
0.8684 High Similarity NPC320671
0.8684 High Similarity NPC275284
0.8684 High Similarity NPC31325
0.8671 High Similarity NPC230531
0.8671 High Similarity NPC215400
0.8658 High Similarity NPC471414
0.8645 High Similarity NPC264875
0.8645 High Similarity NPC163598
0.8645 High Similarity NPC476434
0.8645 High Similarity NPC120774
0.8645 High Similarity NPC267091
0.8639 High Similarity NPC471664
0.8639 High Similarity NPC471665
0.8636 High Similarity NPC470619
0.8636 High Similarity NPC145527
0.8636 High Similarity NPC208785
0.8636 High Similarity NPC470618
0.863 High Similarity NPC135127
0.8627 High Similarity NPC80732
0.8627 High Similarity NPC201148
0.8627 High Similarity NPC476348
0.8627 High Similarity NPC192763
0.8627 High Similarity NPC199311
0.8627 High Similarity NPC215095
0.8627 High Similarity NPC28651
0.8627 High Similarity NPC300262
0.8627 High Similarity NPC261122
0.8627 High Similarity NPC210611
0.8627 High Similarity NPC187398
0.8627 High Similarity NPC3460
0.8625 High Similarity NPC476371
0.8625 High Similarity NPC476372
0.8618 High Similarity NPC93610
0.8618 High Similarity NPC317053
0.8618 High Similarity NPC324492
0.8618 High Similarity NPC241846
0.8609 High Similarity NPC304894
0.8609 High Similarity NPC15659
0.86 High Similarity NPC253878
0.8599 High Similarity NPC202104
0.8591 High Similarity NPC22317
0.8591 High Similarity NPC55793
0.8581 High Similarity NPC243891
0.8571 High Similarity NPC134047
0.8571 High Similarity NPC223006
0.8571 High Similarity NPC272750
0.8571 High Similarity NPC30688
0.8571 High Similarity NPC173729
0.8571 High Similarity NPC176903
0.8562 High Similarity NPC476347
0.8562 High Similarity NPC26394
0.8562 High Similarity NPC58190
0.8562 High Similarity NPC263940
0.8562 High Similarity NPC236202
0.8562 High Similarity NPC82917
0.8562 High Similarity NPC108811
0.8562 High Similarity NPC202742
0.8562 High Similarity NPC170103
0.8562 High Similarity NPC262911
0.8562 High Similarity NPC294558
0.8562 High Similarity NPC70409
0.8562 High Similarity NPC18185
0.8562 High Similarity NPC204770
0.8553 High Similarity NPC43508
0.8553 High Similarity NPC241600
0.8553 High Similarity NPC19862
0.8553 High Similarity NPC307205
0.8553 High Similarity NPC476301
0.8553 High Similarity NPC173726
0.8553 High Similarity NPC235195
0.8545 High Similarity NPC98583
0.8544 High Similarity NPC165483
0.8543 High Similarity NPC163508
0.8543 High Similarity NPC173203
0.8535 High Similarity NPC8712
0.8533 High Similarity NPC87725
0.8533 High Similarity NPC263261
0.8526 High Similarity NPC226809
0.8526 High Similarity NPC302610
0.8526 High Similarity NPC279406
0.8516 High Similarity NPC470934
0.8516 High Similarity NPC188393
0.8516 High Similarity NPC294522
0.8516 High Similarity NPC21184
0.8516 High Similarity NPC120426
0.8516 High Similarity NPC205727
0.8516 High Similarity NPC98624
0.8509 High Similarity NPC90984
0.8509 High Similarity NPC144557
0.8506 High Similarity NPC329836
0.8506 High Similarity NPC32017
0.8506 High Similarity NPC281549
0.8506 High Similarity NPC96930
0.85 High Similarity NPC476373
0.8497 Intermediate Similarity NPC199928
0.8497 Intermediate Similarity NPC96576
0.8493 Intermediate Similarity NPC230219
0.8487 Intermediate Similarity NPC238216
0.8487 Intermediate Similarity NPC79429
0.8487 Intermediate Similarity NPC471667
0.8487 Intermediate Similarity NPC280092
0.8487 Intermediate Similarity NPC471824
0.8487 Intermediate Similarity NPC471415
0.8487 Intermediate Similarity NPC217635
0.8487 Intermediate Similarity NPC185388
0.8487 Intermediate Similarity NPC63879

  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 NPC115203 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
0.8199 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.811 Intermediate Similarity NPD8127 Discontinued
0.8039 Intermediate Similarity NPD7266 Discontinued
0.8023 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD4060 Phase 1
0.7989 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD6234 Discontinued
0.7963 Intermediate Similarity NPD8455 Phase 2
0.7941 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD5844 Phase 1
0.7881 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD1613 Approved
0.7875 Intermediate Similarity NPD1653 Approved
0.787 Intermediate Similarity NPD7228 Approved
0.7867 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD7768 Phase 2
0.7821 Intermediate Similarity NPD6674 Discontinued
0.7803 Intermediate Similarity NPD8313 Approved
0.7803 Intermediate Similarity NPD8312 Approved
0.78 Intermediate Similarity NPD3027 Phase 3
0.7791 Intermediate Similarity NPD37 Approved
0.7784 Intermediate Similarity NPD7199 Phase 2
0.7758 Intermediate Similarity NPD4967 Phase 2
0.7758 Intermediate Similarity NPD4965 Approved
0.7758 Intermediate Similarity NPD4966 Approved
0.7751 Intermediate Similarity NPD6166 Phase 2
0.7751 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD4908 Phase 1
0.7706 Intermediate Similarity NPD7473 Discontinued
0.7692 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD1934 Approved
0.7667 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD2861 Phase 2
0.7661 Intermediate Similarity NPD3818 Discontinued
0.7658 Intermediate Similarity NPD8166 Discontinued
0.7633 Intermediate Similarity NPD6232 Discontinued
0.7619 Intermediate Similarity NPD5494 Approved
0.7613 Intermediate Similarity NPD7097 Phase 1
0.7605 Intermediate Similarity NPD7075 Discontinued
0.7597 Intermediate Similarity NPD6355 Discontinued
0.7595 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD7685 Pre-registration
0.758 Intermediate Similarity NPD5762 Approved
0.758 Intermediate Similarity NPD5763 Approved
0.7572 Intermediate Similarity NPD7074 Phase 3
0.7545 Intermediate Similarity NPD3882 Suspended
0.7544 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD7549 Discontinued
0.753 Intermediate Similarity NPD7819 Suspended
0.753 Intermediate Similarity NPD1465 Phase 2
0.7517 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6798 Discontinued
0.7514 Intermediate Similarity NPD7054 Approved
0.75 Intermediate Similarity NPD6190 Approved
0.7486 Intermediate Similarity NPD6559 Discontinued
0.7485 Intermediate Similarity NPD3817 Phase 2
0.7484 Intermediate Similarity NPD5124 Phase 1
0.7484 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7472 Approved
0.7469 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD7095 Approved
0.7438 Intermediate Similarity NPD4628 Phase 3
0.7425 Intermediate Similarity NPD2801 Approved
0.7425 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD3620 Phase 2
0.7419 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD7411 Suspended
0.7394 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7240 Approved
0.7378 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6959 Discontinued
0.7355 Intermediate Similarity NPD6233 Phase 2
0.7351 Intermediate Similarity NPD8651 Approved
0.7349 Intermediate Similarity NPD4380 Phase 2
0.7345 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD7808 Phase 3
0.7329 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD4110 Phase 3
0.7329 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7229 Phase 3
0.7317 Intermediate Similarity NPD6273 Approved
0.7317 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD4140 Approved
0.7296 Intermediate Similarity NPD2935 Discontinued
0.7289 Intermediate Similarity NPD7458 Discontinued
0.7288 Intermediate Similarity NPD7251 Discontinued
0.7267 Intermediate Similarity NPD1610 Phase 2
0.7262 Intermediate Similarity NPD6801 Discontinued
0.7256 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD6002 Phase 3
0.725 Intermediate Similarity NPD6004 Phase 3
0.725 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD6005 Phase 3
0.7248 Intermediate Similarity NPD4626 Approved
0.7241 Intermediate Similarity NPD5283 Phase 1
0.7238 Intermediate Similarity NPD7906 Approved
0.7232 Intermediate Similarity NPD6797 Phase 2
0.7222 Intermediate Similarity NPD3750 Approved
0.7222 Intermediate Similarity NPD7003 Approved
0.7216 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6653 Approved
0.7213 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD3496 Discontinued
0.7196 Intermediate Similarity NPD7680 Approved
0.7195 Intermediate Similarity NPD1511 Approved
0.7193 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD2797 Approved
0.7186 Intermediate Similarity NPD3226 Approved
0.7182 Intermediate Similarity NPD8434 Phase 2
0.7181 Intermediate Similarity NPD5691 Approved
0.7179 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD5402 Approved
0.716 Intermediate Similarity NPD1652 Phase 2
0.7152 Intermediate Similarity NPD4340 Discontinued
0.7152 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5735 Approved
0.7152 Intermediate Similarity NPD3705 Approved
0.7152 Intermediate Similarity NPD422 Phase 1
0.7143 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD5058 Phase 3
0.7134 Intermediate Similarity NPD6666 Approved
0.7134 Intermediate Similarity NPD6667 Approved
0.7125 Intermediate Similarity NPD2799 Discontinued
0.7125 Intermediate Similarity NPD5588 Approved
0.7125 Intermediate Similarity NPD7033 Discontinued
0.7117 Intermediate Similarity NPD7982 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD6331 Phase 2
0.7115 Intermediate Similarity NPD4625 Phase 3
0.7111 Intermediate Similarity NPD7311 Approved
0.7111 Intermediate Similarity NPD7313 Approved
0.7111 Intermediate Similarity NPD7310 Approved
0.7111 Intermediate Similarity NPD7312 Approved
0.7108 Intermediate Similarity NPD1512 Approved
0.7103 Intermediate Similarity NPD228 Approved
0.7101 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD2424 Discontinued
0.7093 Intermediate Similarity NPD3749 Approved
0.7074 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD8053 Approved
0.7072 Intermediate Similarity NPD8054 Approved
0.7072 Intermediate Similarity NPD7309 Approved
0.7072 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD3268 Approved
0.707 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD3764 Approved
0.7066 Intermediate Similarity NPD5403 Approved
0.7063 Intermediate Similarity NPD4538 Approved
0.7063 Intermediate Similarity NPD4536 Approved
0.7063 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7177 Discontinued
0.7059 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD5535 Approved
0.7055 Intermediate Similarity NPD7843 Approved
0.7052 Intermediate Similarity NPD919 Approved
0.7048 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD5536 Phase 2
0.7045 Intermediate Similarity NPD27 Approved
0.7045 Intermediate Similarity NPD2489 Approved
0.7045 Intermediate Similarity NPD4481 Phase 3
0.7044 Intermediate Similarity NPD447 Suspended
0.7029 Intermediate Similarity NPD3051 Approved
0.7027 Intermediate Similarity NPD7157 Approved
0.7017 Intermediate Similarity NPD4577 Approved
0.7017 Intermediate Similarity NPD4578 Approved
0.7013 Intermediate Similarity NPD6696 Suspended
0.7013 Intermediate Similarity NPD3225 Approved
0.7011 Intermediate Similarity NPD4666 Phase 3
0.7 Intermediate Similarity NPD7038 Approved
0.7 Intermediate Similarity NPD1548 Phase 1
0.7 Intermediate Similarity NPD7039 Approved
0.6995 Remote Similarity NPD8150 Discontinued
0.6995 Remote Similarity NPD4663 Approved
0.6994 Remote Similarity NPD7037 Approved
0.6994 Remote Similarity NPD7833 Phase 2
0.6994 Remote Similarity NPD7831 Phase 2
0.6994 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6993 Remote Similarity NPD1608 Approved
0.6989 Remote Similarity NPD2969 Approved
0.6989 Remote Similarity NPD2970 Approved
0.6988 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6988 Remote Similarity NPD6799 Approved
0.6988 Remote Similarity NPD7041 Phase 2
0.6987 Remote Similarity NPD3018 Phase 2
0.6981 Remote Similarity NPD1558 Phase 1
0.6975 Remote Similarity NPD6032 Approved
0.6975 Remote Similarity NPD5408 Approved
0.6975 Remote Similarity NPD5406 Approved
0.6975 Remote Similarity NPD5404 Approved
0.6975 Remote Similarity NPD5405 Approved
0.6975 Remote Similarity NPD2438 Suspended
0.6966 Remote Similarity NPD3022 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