Structure

Physi-Chem Properties

Molecular Weight:  220.18
Volume:  260.321
LogP:  3.914
LogD:  4.03
LogS:  -4.533
# Rotatable Bonds:  2
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.504
Synthetic Accessibility Score:  4.176
Fsp3:  0.667
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:  -4.474
MDCK Permeability:  2.2480930056190118e-05
Pgp-inhibitor:  0.427
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.776
30% Bioavailability (F30%):  0.149

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.058
Plasma Protein Binding (PPB):  94.07266998291016%
Volume Distribution (VD):  1.285
Pgp-substrate:  4.4335455894470215%

ADMET: Metabolism

CYP1A2-inhibitor:  0.352
CYP1A2-substrate:  0.7
CYP2C19-inhibitor:  0.608
CYP2C19-substrate:  0.897
CYP2C9-inhibitor:  0.418
CYP2C9-substrate:  0.098
CYP2D6-inhibitor:  0.407
CYP2D6-substrate:  0.06
CYP3A4-inhibitor:  0.903
CYP3A4-substrate:  0.831

ADMET: Excretion

Clearance (CL):  7.003
Half-life (T1/2):  0.149

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.185
Drug-inuced Liver Injury (DILI):  0.219
AMES Toxicity:  0.033
Rat Oral Acute Toxicity:  0.586
Maximum Recommended Daily Dose:  0.368
Skin Sensitization:  0.422
Carcinogencity:  0.563
Eye Corrosion:  0.571
Eye Irritation:  0.251
Respiratory Toxicity:  0.977

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

  Natural Product: NPC115385

Natural Product ID:  NPC115385
Common Name*:   (-)-Isoshyobunone
IUPAC Name:   (3S,6S)-3-ethenyl-3-methyl-6-propan-2-yl-2-propan-2-ylidenecyclohexan-1-one
Synonyms:   (-)-Isoshyobunone
Standard InCHIKey:  YMIHAYABXZORPU-SWLSCSKDSA-N
Standard InCHI:  InChI=1S/C15H24O/c1-7-15(6)9-8-12(10(2)3)14(16)13(15)11(4)5/h7,10,12H,1,8-9H2,2-6H3/t12-,15+/m0/s1
SMILES:  C=C[C@]1(C)CC[C@@H](C(C)C)C(=O)C1=C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1814554
PubChem CID:   5318673
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] 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
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. rhizome n.a. PMID[21563811]
NPO25682 Acorus calamus Species Acoraceae Eukaryota rhizomes n.a. n.a. PMID[22671987]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[23373216]
NPO7645 Helicteres isora Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[4031904]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7645 Helicteres isora Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7645 Helicteres isora Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29031 Rhizoma acori graminei n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7645 Helicteres isora Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31101 Acarus calamus Species Acaridae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7645 Helicteres isora Species Malvaceae 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
NPT2 Others Unspecified Emax = 164.0 % PMID[545404]
NPT2 Others Unspecified EC50 = 109400.0 nM PMID[545404]

☑ 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 NPC115385 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
0.8793 High Similarity NPC127582
0.8772 High Similarity NPC27610
0.8772 High Similarity NPC56905
0.8667 High Similarity NPC475124
0.8667 High Similarity NPC285371
0.8621 High Similarity NPC472304
0.8621 High Similarity NPC276764
0.8596 High Similarity NPC192427
0.8571 High Similarity NPC200258
0.8545 High Similarity NPC268564
0.8525 High Similarity NPC251118
0.85 High Similarity NPC165695
0.8448 Intermediate Similarity NPC94991
0.8448 Intermediate Similarity NPC266295
0.8413 Intermediate Similarity NPC260474
0.8413 Intermediate Similarity NPC188292
0.8361 Intermediate Similarity NPC469662
0.8361 Intermediate Similarity NPC6697
0.8333 Intermediate Similarity NPC213152
0.8333 Intermediate Similarity NPC60565
0.8305 Intermediate Similarity NPC285594
0.8305 Intermediate Similarity NPC96551
0.8305 Intermediate Similarity NPC259261
0.8197 Intermediate Similarity NPC197238
0.8197 Intermediate Similarity NPC202118
0.8197 Intermediate Similarity NPC288253
0.8197 Intermediate Similarity NPC472306
0.8182 Intermediate Similarity NPC236623
0.8167 Intermediate Similarity NPC25853
0.8136 Intermediate Similarity NPC311852
0.8136 Intermediate Similarity NPC30215
0.8136 Intermediate Similarity NPC308108
0.8136 Intermediate Similarity NPC170799
0.8125 Intermediate Similarity NPC310992
0.8125 Intermediate Similarity NPC87141
0.8113 Intermediate Similarity NPC14917
0.8113 Intermediate Similarity NPC236355
0.8113 Intermediate Similarity NPC4079
0.8065 Intermediate Similarity NPC212210
0.803 Intermediate Similarity NPC54123
0.803 Intermediate Similarity NPC115023
0.8 Intermediate Similarity NPC116906
0.8 Intermediate Similarity NPC139397
0.8 Intermediate Similarity NPC256846
0.8 Intermediate Similarity NPC32351
0.7966 Intermediate Similarity NPC230823
0.7966 Intermediate Similarity NPC267626
0.7966 Intermediate Similarity NPC193695
0.7966 Intermediate Similarity NPC49575
0.7966 Intermediate Similarity NPC55004
0.7937 Intermediate Similarity NPC470329
0.7931 Intermediate Similarity NPC275472
0.791 Intermediate Similarity NPC251705
0.791 Intermediate Similarity NPC470045
0.791 Intermediate Similarity NPC470044
0.7903 Intermediate Similarity NPC32285
0.7895 Intermediate Similarity NPC474141
0.7879 Intermediate Similarity NPC282593
0.7879 Intermediate Similarity NPC35734
0.7879 Intermediate Similarity NPC2634
0.7879 Intermediate Similarity NPC159577
0.7879 Intermediate Similarity NPC260040
0.7879 Intermediate Similarity NPC307176
0.7879 Intermediate Similarity NPC265782
0.7879 Intermediate Similarity NPC251929
0.7857 Intermediate Similarity NPC27438
0.7857 Intermediate Similarity NPC64866
0.7846 Intermediate Similarity NPC155198
0.7833 Intermediate Similarity NPC60772
0.7812 Intermediate Similarity NPC323005
0.7797 Intermediate Similarity NPC20603
0.7794 Intermediate Similarity NPC329866
0.7794 Intermediate Similarity NPC474796
0.7794 Intermediate Similarity NPC474797
0.7778 Intermediate Similarity NPC473902
0.7761 Intermediate Similarity NPC305501
0.7761 Intermediate Similarity NPC225467
0.7761 Intermediate Similarity NPC234707
0.7761 Intermediate Similarity NPC474562
0.7761 Intermediate Similarity NPC190035
0.7761 Intermediate Similarity NPC5701
0.7759 Intermediate Similarity NPC63396
0.7759 Intermediate Similarity NPC202850
0.7759 Intermediate Similarity NPC5626
0.7742 Intermediate Similarity NPC97322
0.7742 Intermediate Similarity NPC475795
0.7727 Intermediate Similarity NPC182815
0.7705 Intermediate Similarity NPC143834
0.7692 Intermediate Similarity NPC20181
0.7692 Intermediate Similarity NPC4370
0.7692 Intermediate Similarity NPC475523
0.7692 Intermediate Similarity NPC290350
0.7692 Intermediate Similarity NPC220210
0.7681 Intermediate Similarity NPC476346
0.7681 Intermediate Similarity NPC473171
0.7681 Intermediate Similarity NPC293803
0.7679 Intermediate Similarity NPC176819
0.7679 Intermediate Similarity NPC163984
0.7679 Intermediate Similarity NPC58970
0.7679 Intermediate Similarity NPC228776
0.7647 Intermediate Similarity NPC130016
0.7647 Intermediate Similarity NPC109576
0.7647 Intermediate Similarity NPC56747
0.7647 Intermediate Similarity NPC303613
0.7647 Intermediate Similarity NPC474228
0.7647 Intermediate Similarity NPC180015
0.7636 Intermediate Similarity NPC91962
0.7619 Intermediate Similarity NPC167256
0.7586 Intermediate Similarity NPC14002
0.7586 Intermediate Similarity NPC295777
0.7586 Intermediate Similarity NPC296311
0.7586 Intermediate Similarity NPC23117
0.7586 Intermediate Similarity NPC69898
0.7586 Intermediate Similarity NPC37644
0.7581 Intermediate Similarity NPC270042
0.7576 Intermediate Similarity NPC39157
0.7576 Intermediate Similarity NPC20610
0.7576 Intermediate Similarity NPC82477
0.7576 Intermediate Similarity NPC296697
0.7576 Intermediate Similarity NPC142754
0.7571 Intermediate Similarity NPC69408
0.7571 Intermediate Similarity NPC1254
0.7571 Intermediate Similarity NPC469793
0.7571 Intermediate Similarity NPC469796
0.7536 Intermediate Similarity NPC309852
0.7536 Intermediate Similarity NPC255021
0.75 Intermediate Similarity NPC133253
0.75 Intermediate Similarity NPC21944
0.75 Intermediate Similarity NPC181204
0.75 Intermediate Similarity NPC473733
0.75 Intermediate Similarity NPC470078
0.75 Intermediate Similarity NPC4638
0.7463 Intermediate Similarity NPC286814
0.7458 Intermediate Similarity NPC250539
0.7429 Intermediate Similarity NPC65650
0.7429 Intermediate Similarity NPC255650
0.7385 Intermediate Similarity NPC268039
0.7361 Intermediate Similarity NPC275494
0.7361 Intermediate Similarity NPC471409
0.7353 Intermediate Similarity NPC40574
0.7353 Intermediate Similarity NPC214770
0.7353 Intermediate Similarity NPC151045
0.7353 Intermediate Similarity NPC246722
0.7353 Intermediate Similarity NPC477856
0.7324 Intermediate Similarity NPC180886
0.7324 Intermediate Similarity NPC40353
0.7288 Intermediate Similarity NPC45283
0.7286 Intermediate Similarity NPC20025
0.7273 Intermediate Similarity NPC176171
0.7273 Intermediate Similarity NPC92327
0.7246 Intermediate Similarity NPC223187
0.7231 Intermediate Similarity NPC150162
0.7222 Intermediate Similarity NPC197659
0.7222 Intermediate Similarity NPC472300
0.7222 Intermediate Similarity NPC257666
0.7222 Intermediate Similarity NPC266193
0.7206 Intermediate Similarity NPC61702
0.7206 Intermediate Similarity NPC162867
0.7193 Intermediate Similarity NPC145311
0.7167 Intermediate Similarity NPC100809
0.7167 Intermediate Similarity NPC209431
0.7164 Intermediate Similarity NPC176107
0.7164 Intermediate Similarity NPC193770
0.7162 Intermediate Similarity NPC469798
0.7162 Intermediate Similarity NPC26139
0.7162 Intermediate Similarity NPC469797
0.7162 Intermediate Similarity NPC476809
0.7162 Intermediate Similarity NPC474509
0.7143 Intermediate Similarity NPC100380
0.7143 Intermediate Similarity NPC262558
0.7143 Intermediate Similarity NPC474488
0.7143 Intermediate Similarity NPC8610
0.7123 Intermediate Similarity NPC115515
0.7123 Intermediate Similarity NPC189485
0.7123 Intermediate Similarity NPC228911
0.7119 Intermediate Similarity NPC22182
0.7119 Intermediate Similarity NPC471751
0.7091 Intermediate Similarity NPC25771
0.7083 Intermediate Similarity NPC263582
0.7069 Intermediate Similarity NPC118788
0.7067 Intermediate Similarity NPC475833
0.7059 Intermediate Similarity NPC469688
0.7042 Intermediate Similarity NPC470299
0.7042 Intermediate Similarity NPC128346
0.7042 Intermediate Similarity NPC219232
0.7042 Intermediate Similarity NPC211641
0.7027 Intermediate Similarity NPC90965
0.7027 Intermediate Similarity NPC27817
0.7027 Intermediate Similarity NPC170793
0.7015 Intermediate Similarity NPC197089
0.7 Intermediate Similarity NPC304983
0.7 Intermediate Similarity NPC84790
0.6986 Remote Similarity NPC97377
0.6986 Remote Similarity NPC165711
0.6986 Remote Similarity NPC91665
0.6981 Remote Similarity NPC215118
0.6981 Remote Similarity NPC45270
0.6981 Remote Similarity NPC59570
0.6981 Remote Similarity NPC135077
0.6974 Remote Similarity NPC268122

  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 NPC115385 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
0.8136 Intermediate Similarity NPD287 Approved
0.8 Intermediate Similarity NPD4137 Phase 3
0.7879 Intermediate Similarity NPD4691 Approved
0.7879 Intermediate Similarity NPD4747 Approved
0.7794 Intermediate Similarity NPD4687 Approved
0.7794 Intermediate Similarity NPD4058 Approved
0.7576 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD5733 Approved
0.75 Intermediate Similarity NPD5276 Approved
0.6883 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6842 Remote Similarity NPD8028 Phase 2
0.6765 Remote Similarity NPD7331 Phase 2
0.6753 Remote Similarity NPD4221 Approved
0.6753 Remote Similarity NPD4223 Phase 3
0.6711 Remote Similarity NPD4695 Discontinued
0.6709 Remote Similarity NPD1694 Approved
0.6667 Remote Similarity NPD3617 Approved
0.6625 Remote Similarity NPD4519 Discontinued
0.6625 Remote Similarity NPD4623 Approved
0.6625 Remote Similarity NPD5690 Phase 2
0.6618 Remote Similarity NPD7341 Phase 2
0.6582 Remote Similarity NPD3133 Approved
0.6582 Remote Similarity NPD3666 Approved
0.6582 Remote Similarity NPD4197 Approved
0.6582 Remote Similarity NPD3665 Phase 1
0.6543 Remote Similarity NPD3573 Approved
0.65 Remote Similarity NPD5329 Approved
0.6429 Remote Similarity NPD1799 Clinical (unspecified phase)
0.642 Remote Similarity NPD4689 Approved
0.642 Remote Similarity NPD4693 Phase 3
0.642 Remote Similarity NPD4694 Approved
0.642 Remote Similarity NPD7521 Approved
0.642 Remote Similarity NPD3574 Clinical (unspecified phase)
0.642 Remote Similarity NPD4688 Approved
0.642 Remote Similarity NPD6684 Approved
0.642 Remote Similarity NPD3618 Phase 1
0.642 Remote Similarity NPD7146 Approved
0.642 Remote Similarity NPD5280 Approved
0.642 Remote Similarity NPD5330 Approved
0.642 Remote Similarity NPD5205 Approved
0.642 Remote Similarity NPD7334 Approved
0.642 Remote Similarity NPD4690 Approved
0.642 Remote Similarity NPD4138 Approved
0.642 Remote Similarity NPD6409 Approved
0.6329 Remote Similarity NPD3667 Approved
0.631 Remote Similarity NPD5207 Approved
0.6271 Remote Similarity NPD343 Approved
0.6271 Remote Similarity NPD345 Approved
0.6271 Remote Similarity NPD344 Approved
0.6265 Remote Similarity NPD6672 Approved
0.6265 Remote Similarity NPD6903 Approved
0.6265 Remote Similarity NPD5208 Approved
0.6265 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6265 Remote Similarity NPD5737 Approved
0.625 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6235 Remote Similarity NPD6079 Approved
0.6235 Remote Similarity NPD5694 Approved
0.6235 Remote Similarity NPD5284 Approved
0.6235 Remote Similarity NPD5281 Approved
0.622 Remote Similarity NPD5279 Phase 3
0.619 Remote Similarity NPD7285 Clinical (unspecified phase)
0.619 Remote Similarity NPD4753 Phase 2
0.619 Remote Similarity NPD5328 Approved
0.619 Remote Similarity NPD6080 Approved
0.619 Remote Similarity NPD6904 Approved
0.619 Remote Similarity NPD6673 Approved
0.6176 Remote Similarity NPD4193 Approved
0.6176 Remote Similarity NPD4192 Approved
0.6176 Remote Similarity NPD4191 Approved
0.6176 Remote Similarity NPD4194 Approved
0.6173 Remote Similarity NPD4786 Approved
0.6173 Remote Similarity NPD3668 Phase 3
0.6154 Remote Similarity NPD4195 Approved
0.6125 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6118 Remote Similarity NPD5692 Phase 3
0.6087 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6076 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6071 Remote Similarity NPD4518 Approved
0.6056 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6047 Remote Similarity NPD7515 Phase 2
0.6047 Remote Similarity NPD6050 Approved
0.6047 Remote Similarity NPD5693 Phase 1
0.6026 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6024 Remote Similarity NPD6098 Approved
0.6023 Remote Similarity NPD4629 Approved
0.6023 Remote Similarity NPD5210 Approved
0.6 Remote Similarity NPD4692 Approved
0.6 Remote Similarity NPD4139 Approved
0.5977 Remote Similarity NPD4202 Approved
0.5977 Remote Similarity NPD5133 Approved
0.5955 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5955 Remote Similarity NPD5222 Approved
0.5955 Remote Similarity NPD5221 Approved
0.593 Remote Similarity NPD4096 Approved
0.5909 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5909 Remote Similarity NPD7748 Approved
0.5909 Remote Similarity NPD7900 Approved
0.5909 Remote Similarity NPD6001 Approved
0.5893 Remote Similarity NPD5783 Phase 3
0.5889 Remote Similarity NPD3495 Discontinued
0.5889 Remote Similarity NPD5173 Approved
0.5844 Remote Similarity NPD8039 Approved
0.5843 Remote Similarity NPD5695 Phase 3
0.5843 Remote Similarity NPD5654 Approved
0.5843 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5818 Remote Similarity NPD319 Phase 1
0.5795 Remote Similarity NPD7631 Approved
0.5778 Remote Similarity NPD4697 Phase 3
0.5778 Remote Similarity NPD7732 Phase 3
0.5778 Remote Similarity NPD7614 Phase 1
0.5761 Remote Similarity NPD5286 Approved
0.5761 Remote Similarity NPD4696 Approved
0.5761 Remote Similarity NPD5285 Approved
0.5732 Remote Similarity NPD5209 Approved
0.573 Remote Similarity NPD5282 Discontinued
0.5714 Remote Similarity NPD6083 Phase 2
0.5714 Remote Similarity NPD5959 Approved
0.5714 Remote Similarity NPD6084 Phase 2
0.5714 Remote Similarity NPD1696 Phase 3
0.5714 Remote Similarity NPD4755 Approved
0.5714 Remote Similarity NPD7902 Approved
0.5699 Remote Similarity NPD5223 Approved
0.5682 Remote Similarity NPD7609 Phase 3
0.5679 Remote Similarity NPD1507 Clinical (unspecified phase)
0.5672 Remote Similarity NPD4219 Approved
0.5663 Remote Similarity NPD4788 Approved
0.5652 Remote Similarity NPD5696 Approved
0.5638 Remote Similarity NPD5091 Approved
0.5638 Remote Similarity NPD5226 Approved
0.5638 Remote Similarity NPD5225 Approved
0.5638 Remote Similarity NPD5224 Approved
0.5638 Remote Similarity NPD4633 Approved
0.5638 Remote Similarity NPD5211 Phase 2
0.5625 Remote Similarity NPD28 Approved
0.5625 Remote Similarity NPD29 Approved
0.5618 Remote Similarity NPD6399 Phase 3
0.561 Remote Similarity NPD942 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