Structure

Physi-Chem Properties

Molecular Weight:  220.18
Volume:  254.401
LogP:  3.392
LogD:  2.878
LogS:  -2.674
# Rotatable Bonds:  1
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.666
Synthetic Accessibility Score:  4.222
Fsp3:  0.733
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:  -4.691
MDCK Permeability:  1.299379891861463e-05
Pgp-inhibitor:  0.053
Pgp-substrate:  0.131
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.304
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.071
Plasma Protein Binding (PPB):  85.8996810913086%
Volume Distribution (VD):  2.159
Pgp-substrate:  8.85153579711914%

ADMET: Metabolism

CYP1A2-inhibitor:  0.074
CYP1A2-substrate:  0.511
CYP2C19-inhibitor:  0.1
CYP2C19-substrate:  0.903
CYP2C9-inhibitor:  0.064
CYP2C9-substrate:  0.296
CYP2D6-inhibitor:  0.036
CYP2D6-substrate:  0.316
CYP3A4-inhibitor:  0.2
CYP3A4-substrate:  0.439

ADMET: Excretion

Clearance (CL):  8.967
Half-life (T1/2):  0.113

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.548
Drug-inuced Liver Injury (DILI):  0.081
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.299
Maximum Recommended Daily Dose:  0.928
Skin Sensitization:  0.314
Carcinogencity:  0.267
Eye Corrosion:  0.586
Eye Irritation:  0.814
Respiratory Toxicity:  0.94

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

  Natural Product: NPC96793

Natural Product ID:  NPC96793
Common Name*:   3Alpha-Hydroxy-Cyperone
IUPAC Name:   (2R,4aS,7R)-1,4a-dimethyl-7-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-naphthalen-2-ol
Synonyms:  
Standard InCHIKey:  APWLDLGOYJHNIK-YUELXQCFSA-N
Standard InCHI:  InChI=1S/C15H24O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12,14,16H,1,5-9H2,2-4H3/t12-,14-,15+/m1/s1
SMILES:  C=C(C)[C@@H]1CC[C@@]2(C)CC[C@H](C(=C2C1)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2268862
PubChem CID:   14076601
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*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
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)90945-1]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[24704449]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[26967731]
NPO14105.2 Panax pseudo-ginseng var. notoginseng Varieties Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22770 Rhizoma anemones raddeanae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO14105.2 Panax pseudo-ginseng var. notoginseng Varieties Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26858 Rhizoma cyperi preparata n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22796 Cyperus rotundus Species Cyperaceae 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
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster LD50 = 212.7 umol/ml PMID[517671]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster mortality = 0.0 % PMID[517671]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster mortality = 10.0 % PMID[517671]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster mortality = 6.6 % PMID[517671]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster mortality = 6.7 % PMID[517671]
NPT1077 Organism Drosophila melanogaster Drosophila melanogaster mortality = 3.3 % PMID[517671]

☑ 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 NPC96793 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 NPC323424
0.9062 High Similarity NPC96484
0.8923 High Similarity NPC474248
0.8788 High Similarity NPC34834
0.875 High Similarity NPC202017
0.8615 High Similarity NPC171225
0.8615 High Similarity NPC114651
0.8382 Intermediate Similarity NPC23954
0.8358 Intermediate Similarity NPC471560
0.8333 Intermediate Similarity NPC232247
0.8333 Intermediate Similarity NPC251666
0.831 Intermediate Similarity NPC91594
0.8281 Intermediate Similarity NPC81615
0.8261 Intermediate Similarity NPC220939
0.8261 Intermediate Similarity NPC265485
0.8254 Intermediate Similarity NPC240506
0.8235 Intermediate Similarity NPC92801
0.8209 Intermediate Similarity NPC208999
0.8197 Intermediate Similarity NPC48891
0.8182 Intermediate Similarity NPC326310
0.8169 Intermediate Similarity NPC265588
0.8169 Intermediate Similarity NPC244488
0.8169 Intermediate Similarity NPC247325
0.8154 Intermediate Similarity NPC225415
0.8154 Intermediate Similarity NPC68656
0.8154 Intermediate Similarity NPC107540
0.8143 Intermediate Similarity NPC476366
0.8143 Intermediate Similarity NPC201048
0.8125 Intermediate Similarity NPC207007
0.8125 Intermediate Similarity NPC321867
0.8125 Intermediate Similarity NPC68679
0.8116 Intermediate Similarity NPC164022
0.8116 Intermediate Similarity NPC477792
0.8088 Intermediate Similarity NPC473893
0.8082 Intermediate Similarity NPC281138
0.806 Intermediate Similarity NPC68703
0.806 Intermediate Similarity NPC69649
0.8056 Intermediate Similarity NPC470758
0.8056 Intermediate Similarity NPC470711
0.8033 Intermediate Similarity NPC130209
0.8033 Intermediate Similarity NPC148216
0.8033 Intermediate Similarity NPC148163
0.803 Intermediate Similarity NPC258595
0.803 Intermediate Similarity NPC287339
0.8028 Intermediate Similarity NPC32832
0.8028 Intermediate Similarity NPC133580
0.8 Intermediate Similarity NPC474155
0.8 Intermediate Similarity NPC473759
0.8 Intermediate Similarity NPC182717
0.8 Intermediate Similarity NPC83200
0.8 Intermediate Similarity NPC174956
0.7973 Intermediate Similarity NPC295131
0.7969 Intermediate Similarity NPC66020
0.7945 Intermediate Similarity NPC83351
0.7945 Intermediate Similarity NPC167891
0.7941 Intermediate Similarity NPC471238
0.7917 Intermediate Similarity NPC470749
0.7917 Intermediate Similarity NPC253190
0.791 Intermediate Similarity NPC476039
0.791 Intermediate Similarity NPC279434
0.791 Intermediate Similarity NPC475897
0.791 Intermediate Similarity NPC286669
0.791 Intermediate Similarity NPC222366
0.7903 Intermediate Similarity NPC179024
0.7887 Intermediate Similarity NPC469534
0.7887 Intermediate Similarity NPC469593
0.7887 Intermediate Similarity NPC306727
0.7887 Intermediate Similarity NPC469533
0.7887 Intermediate Similarity NPC100334
0.7879 Intermediate Similarity NPC101128
0.7879 Intermediate Similarity NPC290367
0.7867 Intermediate Similarity NPC476646
0.7857 Intermediate Similarity NPC471271
0.7857 Intermediate Similarity NPC110799
0.7857 Intermediate Similarity NPC167706
0.7857 Intermediate Similarity NPC471268
0.7857 Intermediate Similarity NPC471272
0.7846 Intermediate Similarity NPC475251
0.7838 Intermediate Similarity NPC47982
0.7838 Intermediate Similarity NPC209430
0.7838 Intermediate Similarity NPC81306
0.7838 Intermediate Similarity NPC143182
0.7838 Intermediate Similarity NPC84694
0.7838 Intermediate Similarity NPC30986
0.7838 Intermediate Similarity NPC109546
0.7838 Intermediate Similarity NPC28862
0.7812 Intermediate Similarity NPC122239
0.7808 Intermediate Similarity NPC74995
0.7794 Intermediate Similarity NPC197805
0.7778 Intermediate Similarity NPC322353
0.7778 Intermediate Similarity NPC121744
0.7778 Intermediate Similarity NPC118508
0.7763 Intermediate Similarity NPC49964
0.7763 Intermediate Similarity NPC202389
0.7763 Intermediate Similarity NPC87489
0.7763 Intermediate Similarity NPC101462
0.7761 Intermediate Similarity NPC11555
0.7761 Intermediate Similarity NPC163678
0.7761 Intermediate Similarity NPC172613
0.7761 Intermediate Similarity NPC2728
0.7761 Intermediate Similarity NPC282619
0.7761 Intermediate Similarity NPC208198
0.7761 Intermediate Similarity NPC60837
0.7746 Intermediate Similarity NPC130665
0.7746 Intermediate Similarity NPC259049
0.7746 Intermediate Similarity NPC474743
0.7746 Intermediate Similarity NPC474140
0.7746 Intermediate Similarity NPC471799
0.7742 Intermediate Similarity NPC67508
0.7742 Intermediate Similarity NPC84824
0.7733 Intermediate Similarity NPC234193
0.7733 Intermediate Similarity NPC104120
0.7733 Intermediate Similarity NPC206062
0.7733 Intermediate Similarity NPC148685
0.7733 Intermediate Similarity NPC96362
0.7733 Intermediate Similarity NPC157895
0.7733 Intermediate Similarity NPC172013
0.7714 Intermediate Similarity NPC145498
0.7714 Intermediate Similarity NPC283316
0.7703 Intermediate Similarity NPC474216
0.7703 Intermediate Similarity NPC476314
0.7703 Intermediate Similarity NPC11908
0.7681 Intermediate Similarity NPC276616
0.7681 Intermediate Similarity NPC216460
0.7681 Intermediate Similarity NPC45264
0.7681 Intermediate Similarity NPC245795
0.7671 Intermediate Similarity NPC240604
0.7671 Intermediate Similarity NPC30590
0.7671 Intermediate Similarity NPC122418
0.7671 Intermediate Similarity NPC265328
0.7671 Intermediate Similarity NPC290598
0.7671 Intermediate Similarity NPC300324
0.7671 Intermediate Similarity NPC27765
0.7671 Intermediate Similarity NPC73875
0.7671 Intermediate Similarity NPC106364
0.7671 Intermediate Similarity NPC120098
0.7671 Intermediate Similarity NPC46160
0.7671 Intermediate Similarity NPC189883
0.7671 Intermediate Similarity NPC202642
0.7667 Intermediate Similarity NPC244038
0.7647 Intermediate Similarity NPC267027
0.7647 Intermediate Similarity NPC473929
0.7639 Intermediate Similarity NPC243342
0.7639 Intermediate Similarity NPC477138
0.7639 Intermediate Similarity NPC471797
0.7639 Intermediate Similarity NPC91858
0.7632 Intermediate Similarity NPC23852
0.7632 Intermediate Similarity NPC6663
0.7632 Intermediate Similarity NPC249423
0.7632 Intermediate Similarity NPC209620
0.7632 Intermediate Similarity NPC264245
0.7612 Intermediate Similarity NPC144650
0.7612 Intermediate Similarity NPC309300
0.7606 Intermediate Similarity NPC469343
0.7606 Intermediate Similarity NPC242992
0.7606 Intermediate Similarity NPC242001
0.76 Intermediate Similarity NPC308038
0.76 Intermediate Similarity NPC242767
0.76 Intermediate Similarity NPC152061
0.76 Intermediate Similarity NPC31258
0.7576 Intermediate Similarity NPC282694
0.7576 Intermediate Similarity NPC79576
0.7576 Intermediate Similarity NPC194208
0.7568 Intermediate Similarity NPC157996
0.7568 Intermediate Similarity NPC197659
0.7568 Intermediate Similarity NPC130136
0.7568 Intermediate Similarity NPC90979
0.7568 Intermediate Similarity NPC214570
0.7568 Intermediate Similarity NPC471798
0.7568 Intermediate Similarity NPC34177
0.7568 Intermediate Similarity NPC40394
0.7568 Intermediate Similarity NPC472805
0.7568 Intermediate Similarity NPC101475
0.7568 Intermediate Similarity NPC203403
0.7564 Intermediate Similarity NPC185568
0.7564 Intermediate Similarity NPC227132
0.7564 Intermediate Similarity NPC83702
0.7564 Intermediate Similarity NPC205845
0.7564 Intermediate Similarity NPC231310
0.7536 Intermediate Similarity NPC185874
0.7536 Intermediate Similarity NPC82337
0.7536 Intermediate Similarity NPC269077
0.7536 Intermediate Similarity NPC253303
0.7536 Intermediate Similarity NPC308522
0.7536 Intermediate Similarity NPC139207
0.7536 Intermediate Similarity NPC74885
0.7536 Intermediate Similarity NPC477791
0.7534 Intermediate Similarity NPC291503
0.7534 Intermediate Similarity NPC230301
0.7534 Intermediate Similarity NPC285893
0.7534 Intermediate Similarity NPC136188
0.7534 Intermediate Similarity NPC313185
0.7534 Intermediate Similarity NPC69383
0.7534 Intermediate Similarity NPC471723
0.7534 Intermediate Similarity NPC257347
0.7534 Intermediate Similarity NPC138374
0.7534 Intermediate Similarity NPC288035
0.7534 Intermediate Similarity NPC34700
0.7534 Intermediate Similarity NPC477923
0.7534 Intermediate Similarity NPC141071

  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 NPC96793 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
0.8125 Intermediate Similarity NPD368 Approved
0.8033 Intermediate Similarity NPD342 Phase 1
0.7534 Intermediate Similarity NPD6942 Approved
0.7534 Intermediate Similarity NPD8264 Approved
0.7534 Intermediate Similarity NPD7339 Approved
0.7432 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7645 Phase 2
0.7344 Intermediate Similarity NPD4219 Approved
0.7324 Intermediate Similarity NPD6922 Approved
0.7324 Intermediate Similarity NPD6923 Approved
0.7237 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7143 Approved
0.7222 Intermediate Similarity NPD7144 Approved
0.7162 Intermediate Similarity NPD6926 Approved
0.7162 Intermediate Similarity NPD6924 Approved
0.7143 Intermediate Similarity NPD6929 Approved
0.7123 Intermediate Similarity NPD7152 Approved
0.7123 Intermediate Similarity NPD7151 Approved
0.7123 Intermediate Similarity NPD7150 Approved
0.7105 Intermediate Similarity NPD5776 Phase 2
0.7105 Intermediate Similarity NPD6925 Approved
0.7073 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD6930 Phase 2
0.7051 Intermediate Similarity NPD6931 Approved
0.7051 Intermediate Similarity NPD7514 Phase 3
0.7051 Intermediate Similarity NPD7332 Phase 2
0.7051 Intermediate Similarity NPD7525 Registered
0.7013 Intermediate Similarity NPD7145 Approved
0.6974 Remote Similarity NPD6933 Approved
0.6962 Remote Similarity NPD6902 Approved
0.6892 Remote Similarity NPD4243 Approved
0.6875 Remote Similarity NPD3667 Approved
0.679 Remote Similarity NPD6695 Phase 3
0.675 Remote Similarity NPD6898 Phase 1
0.6747 Remote Similarity NPD3618 Phase 1
0.6711 Remote Similarity NPD4785 Approved
0.6711 Remote Similarity NPD4784 Approved
0.6707 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6707 Remote Similarity NPD3665 Phase 1
0.6707 Remote Similarity NPD4786 Approved
0.6707 Remote Similarity NPD3133 Approved
0.6707 Remote Similarity NPD3666 Approved
0.6667 Remote Similarity NPD6932 Approved
0.6627 Remote Similarity NPD6893 Approved
0.6625 Remote Similarity NPD4748 Discontinued
0.6625 Remote Similarity NPD7509 Discontinued
0.6623 Remote Similarity NPD5275 Approved
0.6623 Remote Similarity NPD4190 Phase 3
0.6579 Remote Similarity NPD4732 Discontinued
0.6512 Remote Similarity NPD5328 Approved
0.65 Remote Similarity NPD6683 Phase 2
0.6471 Remote Similarity NPD7750 Discontinued
0.6471 Remote Similarity NPD7524 Approved
0.6452 Remote Similarity NPD385 Approved
0.6452 Remote Similarity NPD384 Approved
0.6364 Remote Similarity NPD7515 Phase 2
0.6364 Remote Similarity NPD6079 Approved
0.6353 Remote Similarity NPD4623 Approved
0.6353 Remote Similarity NPD4519 Discontinued
0.6353 Remote Similarity NPD5279 Phase 3
0.631 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6296 Remote Similarity NPD4195 Approved
0.6292 Remote Similarity NPD4202 Approved
0.6237 Remote Similarity NPD7640 Approved
0.6237 Remote Similarity NPD7639 Approved
0.6235 Remote Similarity NPD1696 Phase 3
0.618 Remote Similarity NPD7087 Discontinued
0.618 Remote Similarity NPD7637 Suspended
0.6173 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6136 Remote Similarity NPD4753 Phase 2
0.6129 Remote Similarity NPD7638 Approved
0.6129 Remote Similarity NPD4225 Approved
0.6118 Remote Similarity NPD3668 Phase 3
0.6111 Remote Similarity NPD4194 Approved
0.6111 Remote Similarity NPD4192 Approved
0.6111 Remote Similarity NPD4191 Approved
0.6111 Remote Similarity NPD4193 Approved
0.6105 Remote Similarity NPD5211 Phase 2
0.6087 Remote Similarity NPD5222 Approved
0.6087 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6087 Remote Similarity NPD4697 Phase 3
0.6087 Remote Similarity NPD5221 Approved
0.6071 Remote Similarity NPD4221 Approved
0.6071 Remote Similarity NPD4223 Phase 3
0.6067 Remote Similarity NPD7136 Phase 2
0.6047 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6047 Remote Similarity NPD1694 Approved
0.6044 Remote Similarity NPD7748 Approved
0.6032 Remote Similarity NPD4265 Approved
0.6024 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6024 Remote Similarity NPD4695 Discontinued
0.6022 Remote Similarity NPD5173 Approved
0.6022 Remote Similarity NPD4755 Approved
0.5979 Remote Similarity NPD5141 Approved
0.5976 Remote Similarity NPD3617 Approved
0.5974 Remote Similarity NPD791 Approved
0.5974 Remote Similarity NPD15 Approved
0.5957 Remote Similarity NPD5290 Discontinued
0.5955 Remote Similarity NPD6051 Approved
0.5934 Remote Similarity NPD5779 Approved
0.5934 Remote Similarity NPD6399 Phase 3
0.5934 Remote Similarity NPD5778 Approved
0.593 Remote Similarity NPD4197 Approved
0.5895 Remote Similarity NPD4696 Approved
0.5895 Remote Similarity NPD4700 Approved
0.5895 Remote Similarity NPD5285 Approved
0.5895 Remote Similarity NPD5286 Approved
0.5862 Remote Similarity NPD5329 Approved
0.5851 Remote Similarity NPD7902 Approved
0.5833 Remote Similarity NPD4822 Approved
0.5833 Remote Similarity NPD4819 Approved
0.5833 Remote Similarity NPD4820 Approved
0.5833 Remote Similarity NPD5223 Approved
0.5833 Remote Similarity NPD4821 Approved
0.5833 Remote Similarity NPD4159 Approved
0.5824 Remote Similarity NPD6411 Approved
0.5814 Remote Similarity NPD5332 Approved
0.5814 Remote Similarity NPD7154 Phase 3
0.5814 Remote Similarity NPD5362 Discontinued
0.5814 Remote Similarity NPD5331 Approved
0.5814 Remote Similarity NPD4788 Approved
0.5806 Remote Similarity NPD5210 Approved
0.5806 Remote Similarity NPD4629 Approved
0.5802 Remote Similarity NPD8039 Approved
0.5795 Remote Similarity NPD6409 Approved
0.5795 Remote Similarity NPD5690 Phase 2
0.5795 Remote Similarity NPD7146 Approved
0.5795 Remote Similarity NPD7334 Approved
0.5795 Remote Similarity NPD4689 Approved
0.5795 Remote Similarity NPD6684 Approved
0.5795 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5795 Remote Similarity NPD5205 Approved
0.5795 Remote Similarity NPD4690 Approved
0.5795 Remote Similarity NPD4138 Approved
0.5795 Remote Similarity NPD4694 Approved
0.5795 Remote Similarity NPD4693 Phase 3
0.5795 Remote Similarity NPD5330 Approved
0.5795 Remote Similarity NPD4688 Approved
0.5795 Remote Similarity NPD7521 Approved
0.5795 Remote Similarity NPD5280 Approved
0.5789 Remote Similarity NPD7331 Phase 2
0.5783 Remote Similarity NPD4271 Approved
0.5783 Remote Similarity NPD4268 Approved
0.5773 Remote Similarity NPD5224 Approved
0.5773 Remote Similarity NPD5225 Approved
0.5773 Remote Similarity NPD4633 Approved
0.5773 Remote Similarity NPD7632 Discontinued
0.5773 Remote Similarity NPD5226 Approved
0.5765 Remote Similarity NPD4790 Discontinued
0.5765 Remote Similarity NPD4139 Approved
0.5765 Remote Similarity NPD4692 Approved
0.5753 Remote Similarity NPD1145 Discontinued
0.5733 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5732 Remote Similarity NPD1346 Approved
0.5714 Remote Similarity NPD5175 Approved
0.5714 Remote Similarity NPD4754 Approved
0.5714 Remote Similarity NPD5174 Approved
0.5698 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5698 Remote Similarity NPD4269 Approved
0.5698 Remote Similarity NPD4270 Approved
0.5684 Remote Similarity NPD6084 Phase 2
0.5684 Remote Similarity NPD6083 Phase 2
0.5667 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5667 Remote Similarity NPD4723 Approved
0.5667 Remote Similarity NPD6903 Approved
0.5667 Remote Similarity NPD4722 Approved
0.5658 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5658 Remote Similarity NPD7341 Phase 2
0.5647 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5641 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5638 Remote Similarity NPD5695 Phase 3
0.5604 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5604 Remote Similarity NPD6101 Approved
0.56 Remote Similarity NPD4768 Approved
0.56 Remote Similarity NPD6640 Phase 3
0.56 Remote Similarity NPD7128 Approved
0.56 Remote Similarity NPD4767 Approved
0.56 Remote Similarity NPD5739 Approved
0.56 Remote Similarity NPD6402 Approved
0.56 Remote Similarity NPD6675 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