Structure

Physi-Chem Properties

Molecular Weight:  336.23
Volume:  358.695
LogP:  2.584
LogD:  2.372
LogS:  -3.592
# Rotatable Bonds:  4
TPSA:  73.83
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.79
Synthetic Accessibility Score:  4.678
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.545
MDCK Permeability:  1.3842814041709062e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.037
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.341
Plasma Protein Binding (PPB):  94.11034393310547%
Volume Distribution (VD):  1.419
Pgp-substrate:  5.1789445877075195%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.205
CYP2C19-inhibitor:  0.174
CYP2C19-substrate:  0.759
CYP2C9-inhibitor:  0.302
CYP2C9-substrate:  0.094
CYP2D6-inhibitor:  0.047
CYP2D6-substrate:  0.077
CYP3A4-inhibitor:  0.921
CYP3A4-substrate:  0.299

ADMET: Excretion

Clearance (CL):  9.104
Half-life (T1/2):  0.424

ADMET: Toxicity

hERG Blockers:  0.087
Human Hepatotoxicity (H-HT):  0.321
Drug-inuced Liver Injury (DILI):  0.033
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.769
Maximum Recommended Daily Dose:  0.161
Skin Sensitization:  0.313
Carcinogencity:  0.797
Eye Corrosion:  0.005
Eye Irritation:  0.168
Respiratory Toxicity:  0.967

Download Data

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

  Natural Product: NPC67003

Natural Product ID:  NPC67003
Common Name*:   Marrubenol
IUPAC Name:   (1R,3R,4R,4aS,8S,8aS)-4-[2-(furan-3-yl)ethyl]-8-(hydroxymethyl)-3,4a,8-trimethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalene-1,4-diol
Synonyms:   Marrubenol
Standard InCHIKey:  NZMHIKFTAXRIDL-FQFOHHTNSA-N
Standard InCHI:  InChI=1S/C20H32O4/c1-14-11-16(22)17-18(2,13-21)7-4-8-19(17,3)20(14,23)9-5-15-6-10-24-12-15/h6,10,12,14,16-17,21-23H,4-5,7-9,11,13H2,1-3H3/t14-,16-,17+,18-,19+,20-/m1/s1
SMILES:  C[C@@H]1C[C@H]([C@H]2[C@](C)(CCC[C@]2(C)[C@]1(CCc1ccoc1)O)CO)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL389065
PubChem CID:   10449689
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO24498 Casearia membranacea Species Salicaceae Eukaryota n.a. leaf n.a. PMID[14709876]
NPO24498 Casearia membranacea Species Salicaceae Eukaryota n.a. twig n.a. PMID[14709876]
NPO24498 Casearia membranacea Species Salicaceae Eukaryota Leaves; Twigs n.a. n.a. PMID[15043402]
NPO23473 Cinnamomum kotoense Species Lauraceae Eukaryota stem wood n.a. n.a. PMID[16180806]
NPO24498 Casearia membranacea Species Salicaceae Eukaryota n.a. n.a. n.a. PMID[16309320]
NPO23473 Cinnamomum kotoense Species Lauraceae Eukaryota leaves n.a. n.a. PMID[16792412]
NPO23769 Ainsliaea macrocephala Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[18484734]
NPO23473 Cinnamomum kotoense Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[18489163]
NPO23557 Zanthoxylum ailanthoides Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19128011]
NPO24301 Buxus microphylla Species Buxaceae Eukaryota leaves and stems Kunming, Yunnan, China 2007-AUG PMID[19133780]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23557 Zanthoxylum ailanthoides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24498 Casearia membranacea Species Salicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24301 Buxus microphylla Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23264 Marrubium vulgare Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23302 Strychnos camptoneura Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21478 Buxus hyrcana Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24301 Buxus microphylla Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24498 Casearia membranacea Species Salicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23557 Zanthoxylum ailanthoides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23302 Strychnos camptoneura Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23264 Marrubium vulgare Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24301 Buxus microphylla Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23264 Marrubium vulgare Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24015 Perknaster fuscus Species Ganeriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22684 Enrichment culture Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24258 Vellozia nivea Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21352 Boronia ternata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23264 Marrubium vulgare Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24462 Pityrogramma ebenea Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28748 Aphis sambuci Species Aphididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23557 Zanthoxylum ailanthoides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18918 Lecanicillium muscarium Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23473 Cinnamomum kotoense Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23930 Luculia pinceana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24993 Conospermum teretifolium Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24952 Galeopsis tetrahit Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18735 Pinus mugo Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7197 Colchicum robustum Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23428 Tinus mamillata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25080 Sphaeria maculans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23896 Cytisus ratisbonensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23721 Epidendrum rigidum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23769 Ainsliaea macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21478 Buxus hyrcana Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20498 Cephalaria ambrosioides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24498 Casearia membranacea Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23474 Abies veitchii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24301 Buxus microphylla Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23849 Dicoma anomala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23302 Strychnos camptoneura Species Loganiaceae 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
NPT177 Tissue Aorta Rattus norvegicus IC50 = 10000.0 nM PMID[493762]
NPT177 Tissue Aorta Rattus norvegicus Activity = 7.9 % PMID[493762]

☑ 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 NPC67003 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
0.9704 High Similarity NPC121158
0.9635 High Similarity NPC5676
0.942 High Similarity NPC251865
0.9362 High Similarity NPC125182
0.9362 High Similarity NPC69647
0.9357 High Similarity NPC255414
0.9348 High Similarity NPC243577
0.9259 High Similarity NPC46896
0.9185 High Similarity NPC476947
0.9173 High Similarity NPC61788
0.9091 High Similarity NPC472654
0.9085 High Similarity NPC216755
0.9085 High Similarity NPC471174
0.9051 High Similarity NPC4764
0.9044 High Similarity NPC158525
0.9 High Similarity NPC263337
0.8958 High Similarity NPC195325
0.8936 High Similarity NPC476946
0.8904 High Similarity NPC469503
0.8904 High Similarity NPC268905
0.8897 High Similarity NPC218838
0.8897 High Similarity NPC212257
0.8889 High Similarity NPC471007
0.8889 High Similarity NPC89133
0.8857 High Similarity NPC90296
0.8849 High Similarity NPC471996
0.8844 High Similarity NPC57998
0.8844 High Similarity NPC178932
0.8844 High Similarity NPC282445
0.8828 High Similarity NPC470998
0.8811 High Similarity NPC185456
0.8792 High Similarity NPC195954
0.8792 High Similarity NPC194499
0.8792 High Similarity NPC472772
0.8786 High Similarity NPC90953
0.8784 High Similarity NPC35000
0.8784 High Similarity NPC469336
0.8784 High Similarity NPC92979
0.8776 High Similarity NPC75906
0.8776 High Similarity NPC121615
0.8776 High Similarity NPC294511
0.8767 High Similarity NPC196846
0.8767 High Similarity NPC476122
0.8742 High Similarity NPC200782
0.8741 High Similarity NPC476944
0.8732 High Similarity NPC20578
0.8732 High Similarity NPC52412
0.8732 High Similarity NPC62103
0.8725 High Similarity NPC41880
0.8716 High Similarity NPC30222
0.8699 High Similarity NPC470791
0.8699 High Similarity NPC470790
0.869 High Similarity NPC221809
0.869 High Similarity NPC302987
0.8684 High Similarity NPC234660
0.8684 High Similarity NPC51568
0.8681 High Similarity NPC41182
0.8675 High Similarity NPC335761
0.8675 High Similarity NPC470789
0.8671 High Similarity NPC103134
0.8667 High Similarity NPC214495
0.8667 High Similarity NPC470119
0.8667 High Similarity NPC475066
0.8667 High Similarity NPC249021
0.8667 High Similarity NPC304692
0.8667 High Similarity NPC88007
0.8662 High Similarity NPC205765
0.8658 High Similarity NPC155939
0.8658 High Similarity NPC296807
0.8658 High Similarity NPC141538
0.8657 High Similarity NPC23086
0.8649 High Similarity NPC470996
0.8649 High Similarity NPC246164
0.8649 High Similarity NPC472672
0.8643 High Similarity NPC310043
0.8639 High Similarity NPC156189
0.8639 High Similarity NPC477404
0.8639 High Similarity NPC470997
0.8639 High Similarity NPC196864
0.8639 High Similarity NPC228842
0.8627 High Similarity NPC476856
0.8627 High Similarity NPC476858
0.8627 High Similarity NPC476857
0.8621 High Similarity NPC470999
0.8618 High Similarity NPC472771
0.8618 High Similarity NPC5079
0.8609 High Similarity NPC475226
0.8609 High Similarity NPC472671
0.8609 High Similarity NPC475967
0.8609 High Similarity NPC474611
0.86 High Similarity NPC104736
0.8592 High Similarity NPC56197
0.8591 High Similarity NPC253201
0.8591 High Similarity NPC302054
0.8591 High Similarity NPC34421
0.8591 High Similarity NPC98206
0.8591 High Similarity NPC237259
0.8581 High Similarity NPC18135
0.8581 High Similarity NPC272590
0.8571 High Similarity NPC211625
0.8571 High Similarity NPC234494
0.8571 High Similarity NPC214572
0.8562 High Similarity NPC302369
0.8562 High Similarity NPC134254
0.8562 High Similarity NPC477405
0.8562 High Similarity NPC39986
0.8562 High Similarity NPC470941
0.8562 High Similarity NPC472773
0.8562 High Similarity NPC250228
0.8562 High Similarity NPC71821
0.8553 High Similarity NPC472653
0.8551 High Similarity NPC471995
0.8543 High Similarity NPC470118
0.8543 High Similarity NPC299038
0.8543 High Similarity NPC45101
0.8543 High Similarity NPC7059
0.8543 High Similarity NPC197137
0.8533 High Similarity NPC214541
0.8533 High Similarity NPC264943
0.8533 High Similarity NPC476262
0.8533 High Similarity NPC44675
0.8529 High Similarity NPC477040
0.8523 High Similarity NPC476201
0.8523 High Similarity NPC33938
0.8519 High Similarity NPC46536
0.8519 High Similarity NPC138139
0.8516 High Similarity NPC476850
0.8516 High Similarity NPC476861
0.8516 High Similarity NPC476853
0.8516 High Similarity NPC472774
0.8516 High Similarity NPC472775
0.8514 High Similarity NPC159927
0.8514 High Similarity NPC469335
0.8506 High Similarity NPC276551
0.8497 Intermediate Similarity NPC470792
0.8497 Intermediate Similarity NPC82851
0.8497 Intermediate Similarity NPC79571
0.8497 Intermediate Similarity NPC68848
0.8497 Intermediate Similarity NPC329938
0.8497 Intermediate Similarity NPC69028
0.8496 Intermediate Similarity NPC477967
0.8493 Intermediate Similarity NPC346
0.8487 Intermediate Similarity NPC307383
0.8467 Intermediate Similarity NPC223063
0.8467 Intermediate Similarity NPC120836
0.8467 Intermediate Similarity NPC114880
0.8452 Intermediate Similarity NPC23387
0.8452 Intermediate Similarity NPC93172
0.8452 Intermediate Similarity NPC470875
0.8452 Intermediate Similarity NPC97574
0.8452 Intermediate Similarity NPC472141
0.8446 Intermediate Similarity NPC471001
0.8444 Intermediate Similarity NPC179354
0.8444 Intermediate Similarity NPC290193
0.8442 Intermediate Similarity NPC663
0.8442 Intermediate Similarity NPC292389
0.8442 Intermediate Similarity NPC283209
0.8442 Intermediate Similarity NPC469338
0.8442 Intermediate Similarity NPC419
0.8442 Intermediate Similarity NPC224394
0.8435 Intermediate Similarity NPC286038
0.8433 Intermediate Similarity NPC272899
0.8431 Intermediate Similarity NPC25255
0.8431 Intermediate Similarity NPC477402
0.8431 Intermediate Similarity NPC8389
0.8431 Intermediate Similarity NPC287559
0.8421 Intermediate Similarity NPC472776
0.8421 Intermediate Similarity NPC472778
0.8421 Intermediate Similarity NPC261597
0.8421 Intermediate Similarity NPC472777
0.8417 Intermediate Similarity NPC471544
0.8417 Intermediate Similarity NPC473344
0.8414 Intermediate Similarity NPC64568
0.8414 Intermediate Similarity NPC223415
0.8411 Intermediate Similarity NPC469850
0.8406 Intermediate Similarity NPC476925
0.84 Intermediate Similarity NPC182427
0.84 Intermediate Similarity NPC29695
0.84 Intermediate Similarity NPC308205
0.84 Intermediate Similarity NPC322546
0.8397 Intermediate Similarity NPC472651
0.8397 Intermediate Similarity NPC472282
0.8394 Intermediate Similarity NPC112706
0.8394 Intermediate Similarity NPC476917
0.8394 Intermediate Similarity NPC327527
0.8394 Intermediate Similarity NPC477966
0.8394 Intermediate Similarity NPC207294
0.8394 Intermediate Similarity NPC477123
0.8392 Intermediate Similarity NPC202260
0.8387 Intermediate Similarity NPC476860
0.8387 Intermediate Similarity NPC470940
0.8387 Intermediate Similarity NPC469849
0.8387 Intermediate Similarity NPC123088
0.8387 Intermediate Similarity NPC470182
0.8387 Intermediate Similarity NPC271657
0.8378 Intermediate Similarity NPC66991
0.8377 Intermediate Similarity NPC18347
0.8377 Intermediate Similarity NPC207978
0.8377 Intermediate Similarity NPC149896
0.8377 Intermediate Similarity NPC96443

  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 NPC67003 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
0.8912 High Similarity NPD5761 Phase 2
0.8912 High Similarity NPD5760 Phase 2
0.7952 Intermediate Similarity NPD8434 Phase 2
0.7852 Intermediate Similarity NPD4628 Phase 3
0.7758 Intermediate Similarity NPD6764 Approved
0.7758 Intermediate Similarity NPD6765 Approved
0.7574 Intermediate Similarity NPD6785 Approved
0.7574 Intermediate Similarity NPD6784 Approved
0.7533 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6273 Approved
0.732 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD1471 Phase 3
0.7267 Intermediate Similarity NPD7819 Suspended
0.7237 Intermediate Similarity NPD6099 Approved
0.7237 Intermediate Similarity NPD6100 Approved
0.7212 Intermediate Similarity NPD8127 Discontinued
0.7195 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD2344 Approved
0.7161 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5844 Phase 1
0.7153 Intermediate Similarity NPD1608 Approved
0.7153 Intermediate Similarity NPD3972 Approved
0.7152 Intermediate Similarity NPD5494 Approved
0.7135 Intermediate Similarity NPD6559 Discontinued
0.7124 Intermediate Similarity NPD2796 Approved
0.7117 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD920 Approved
0.7089 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6599 Discontinued
0.707 Intermediate Similarity NPD7236 Approved
0.7059 Intermediate Similarity NPD2799 Discontinued
0.7055 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD1549 Phase 2
0.7019 Intermediate Similarity NPD3226 Approved
0.7019 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD7458 Discontinued
0.7006 Intermediate Similarity NPD2309 Approved
0.7 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.6987 Remote Similarity NPD2800 Approved
0.6981 Remote Similarity NPD642 Clinical (unspecified phase)
0.6981 Remote Similarity NPD2532 Approved
0.6981 Remote Similarity NPD2533 Approved
0.6981 Remote Similarity NPD2534 Approved
0.6975 Remote Similarity NPD4380 Phase 2
0.6974 Remote Similarity NPD6355 Discontinued
0.6968 Remote Similarity NPD6002 Phase 3
0.6968 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6968 Remote Similarity NPD2346 Discontinued
0.6968 Remote Similarity NPD6005 Phase 3
0.6968 Remote Similarity NPD6004 Phase 3
0.6968 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6962 Remote Similarity NPD643 Clinical (unspecified phase)
0.6948 Remote Similarity NPD7033 Discontinued
0.6944 Remote Similarity NPD17 Approved
0.6943 Remote Similarity NPD7003 Approved
0.6939 Remote Similarity NPD6696 Suspended
0.6928 Remote Similarity NPD7075 Discontinued
0.6928 Remote Similarity NPD3749 Approved
0.6909 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6908 Remote Similarity NPD4140 Approved
0.6905 Remote Similarity NPD6959 Discontinued
0.6905 Remote Similarity NPD1247 Approved
0.6903 Remote Similarity NPD1551 Phase 2
0.6903 Remote Similarity NPD2935 Discontinued
0.6901 Remote Similarity NPD7893 Clinical (unspecified phase)
0.689 Remote Similarity NPD1934 Approved
0.6887 Remote Similarity NPD3764 Approved
0.6875 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6875 Remote Similarity NPD8404 Phase 2
0.6867 Remote Similarity NPD3882 Suspended
0.6863 Remote Similarity NPD5735 Approved
0.6859 Remote Similarity NPD5762 Approved
0.6859 Remote Similarity NPD5763 Approved
0.6852 Remote Similarity NPD7239 Suspended
0.6842 Remote Similarity NPD8032 Phase 2
0.6839 Remote Similarity NPD1510 Phase 2
0.6835 Remote Similarity NPD3750 Approved
0.6835 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6835 Remote Similarity NPD4110 Phase 3
0.6829 Remote Similarity NPD7411 Suspended
0.6828 Remote Similarity NPD1778 Approved
0.6826 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6824 Remote Similarity NPD1876 Approved
0.6818 Remote Similarity NPD1607 Approved
0.6815 Remote Similarity NPD970 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6799 Approved
0.6802 Remote Similarity NPD3818 Discontinued
0.68 Remote Similarity NPD2861 Phase 2
0.6797 Remote Similarity NPD1240 Approved
0.6788 Remote Similarity NPD6801 Discontinued
0.6786 Remote Similarity NPD919 Approved
0.6784 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6776 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6776 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6776 Remote Similarity NPD2313 Discontinued
0.6772 Remote Similarity NPD1243 Approved
0.6766 Remote Similarity NPD7768 Phase 2
0.6766 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6765 Remote Similarity NPD7229 Phase 3
0.6757 Remote Similarity NPD5327 Phase 3
0.6755 Remote Similarity NPD6832 Phase 2
0.6747 Remote Similarity NPD2801 Approved
0.6735 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6733 Remote Similarity NPD2798 Approved
0.6733 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6731 Remote Similarity NPD3748 Approved
0.6731 Remote Similarity NPD4308 Phase 3
0.6712 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6711 Remote Similarity NPD1283 Approved
0.671 Remote Similarity NPD6353 Approved
0.6708 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6705 Remote Similarity NPD7177 Discontinued
0.669 Remote Similarity NPD1241 Discontinued
0.669 Remote Similarity NPD9545 Approved
0.6688 Remote Similarity NPD2979 Phase 3
0.6687 Remote Similarity NPD37 Approved
0.6687 Remote Similarity NPD6844 Discontinued
0.6686 Remote Similarity NPD6166 Phase 2
0.6686 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6686 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6685 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4966 Approved
0.6667 Remote Similarity NPD8312 Approved
0.6667 Remote Similarity NPD4967 Phase 2
0.6667 Remote Similarity NPD3268 Approved
0.6667 Remote Similarity NPD2797 Approved
0.6667 Remote Similarity NPD4965 Approved
0.6667 Remote Similarity NPD8313 Approved
0.6647 Remote Similarity NPD7473 Discontinued
0.6644 Remote Similarity NPD5585 Approved
0.6631 Remote Similarity NPD3057 Approved
0.6629 Remote Similarity NPD7074 Phase 3
0.6628 Remote Similarity NPD3926 Phase 2
0.6626 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6623 Remote Similarity NPD6917 Clinical (unspecified phase)
0.661 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6609 Remote Similarity NPD7799 Discontinued
0.6608 Remote Similarity NPD7199 Phase 2
0.6607 Remote Similarity NPD5402 Approved
0.6607 Remote Similarity NPD3817 Phase 2
0.6605 Remote Similarity NPD1511 Approved
0.6604 Remote Similarity NPD2424 Discontinued
0.6603 Remote Similarity NPD6651 Approved
0.6601 Remote Similarity NPD7095 Approved
0.6601 Remote Similarity NPD5952 Clinical (unspecified phase)
0.66 Remote Similarity NPD8651 Approved
0.6597 Remote Similarity NPD7157 Approved
0.6596 Remote Similarity NPD7497 Discontinued
0.659 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6587 Remote Similarity NPD6279 Approved
0.6587 Remote Similarity NPD6280 Approved
0.6587 Remote Similarity NPD7577 Discontinued
0.6584 Remote Similarity NPD3887 Approved
0.6582 Remote Similarity NPD4476 Approved
0.6582 Remote Similarity NPD4477 Approved
0.6581 Remote Similarity NPD4307 Phase 2
0.6579 Remote Similarity NPD9494 Approved
0.6571 Remote Similarity NPD7054 Approved
0.657 Remote Similarity NPD6232 Discontinued
0.6566 Remote Similarity NPD7028 Phase 2
0.6562 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6561 Remote Similarity NPD7097 Phase 1
0.6558 Remote Similarity NPD6798 Discontinued
0.6554 Remote Similarity NPD3496 Discontinued
0.6554 Remote Similarity NPD7685 Pre-registration
0.6548 Remote Similarity NPD8455 Phase 2
0.6543 Remote Similarity NPD3533 Approved
0.6543 Remote Similarity NPD2972 Approved
0.6538 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6538 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6534 Remote Similarity NPD7472 Approved
0.6531 Remote Similarity NPD1651 Approved
0.6524 Remote Similarity NPD1512 Approved
0.6522 Remote Similarity NPD8166 Discontinued
0.6516 Remote Similarity NPD6233 Phase 2
0.6516 Remote Similarity NPD6663 Approved
0.6514 Remote Similarity NPD3751 Discontinued
0.6514 Remote Similarity NPD2163 Approved
0.651 Remote Similarity NPD1281 Approved
0.6509 Remote Similarity NPD2296 Approved
0.6506 Remote Similarity NPD2651 Approved
0.6506 Remote Similarity NPD2649 Approved
0.6497 Remote Similarity NPD6653 Approved
0.6494 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6491 Remote Similarity NPD6234 Discontinued
0.6485 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6485 Remote Similarity NPD5403 Approved
0.6484 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6483 Remote Similarity NPD6671 Approved
0.6481 Remote Similarity NPD2354 Approved
0.6478 Remote Similarity NPD2438 Suspended
0.6474 Remote Similarity NPD5711 Approved
0.6474 Remote Similarity NPD6808 Phase 2
0.6474 Remote Similarity NPD4060 Phase 1

  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