Structure

Physi-Chem Properties

Molecular Weight:  218.17
Volume:  245.844
LogP:  4.284
LogD:  3.869
LogS:  -4.845
# Rotatable Bonds:  0
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.566
Synthetic Accessibility Score:  5.309
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.7
MDCK Permeability:  1.965828960237559e-05
Pgp-inhibitor:  0.189
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.503
30% Bioavailability (F30%):  0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.956
Plasma Protein Binding (PPB):  89.17639923095703%
Volume Distribution (VD):  1.977
Pgp-substrate:  9.72284984588623%

ADMET: Metabolism

CYP1A2-inhibitor:  0.077
CYP1A2-substrate:  0.533
CYP2C19-inhibitor:  0.295
CYP2C19-substrate:  0.926
CYP2C9-inhibitor:  0.288
CYP2C9-substrate:  0.626
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.506
CYP3A4-inhibitor:  0.237
CYP3A4-substrate:  0.36

ADMET: Excretion

Clearance (CL):  14.795
Half-life (T1/2):  0.059

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.163
Drug-inuced Liver Injury (DILI):  0.286
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.675
Maximum Recommended Daily Dose:  0.044
Skin Sensitization:  0.113
Carcinogencity:  0.3
Eye Corrosion:  0.702
Eye Irritation:  0.924
Respiratory Toxicity:  0.941

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

  Natural Product: NPC6697

Natural Product ID:  NPC6697
Common Name*:   Vulgarone B
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  KTPOZFYJWLGJGH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H22O/c1-9-8-10(16)12-13-11(9)15(12,4)7-5-6-14(13,2)3/h8,11-13H,5-7H2,1-4H3
SMILES:  CC1=CC(=O)C2C3C1C2(C)CCCC3(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2272434
PubChem CID:   530428
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
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. leaf n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. stem n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. flower n.a. DOI[10.1007/s11418-006-0112-9]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)90945-1]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17432574]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. rhizome n.a. PMID[18787781]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[21302967]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[24704449]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24813739]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[26967731]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27228227]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[6387056]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[9544564]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20902 Atractylodes macrocephala Species Asteraceae 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
NPT928 Organism Pomacea canaliculata Pomacea canaliculata mortality = 100.0 % PMID[568955]
NPT928 Organism Pomacea canaliculata Pomacea canaliculata LC50 = 30000.0 nM PMID[568955]

☑ 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 NPC6697 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
0.9344 High Similarity NPC475124
0.9153 High Similarity NPC170799
0.9153 High Similarity NPC308108
0.8852 High Similarity NPC127582
0.873 High Similarity NPC285371
0.871 High Similarity NPC213152
0.8689 High Similarity NPC472304
0.8689 High Similarity NPC276764
0.8525 High Similarity NPC56905
0.8525 High Similarity NPC27610
0.8438 Intermediate Similarity NPC212210
0.8387 Intermediate Similarity NPC96551
0.8387 Intermediate Similarity NPC285594
0.8361 Intermediate Similarity NPC115385
0.8308 Intermediate Similarity NPC251118
0.8305 Intermediate Similarity NPC268564
0.8281 Intermediate Similarity NPC288253
0.8281 Intermediate Similarity NPC165695
0.8235 Intermediate Similarity NPC246722
0.8235 Intermediate Similarity NPC151045
0.8226 Intermediate Similarity NPC311852
0.8209 Intermediate Similarity NPC188292
0.8209 Intermediate Similarity NPC260474
0.8209 Intermediate Similarity NPC87141
0.8209 Intermediate Similarity NPC310992
0.8154 Intermediate Similarity NPC469662
0.8125 Intermediate Similarity NPC60565
0.8088 Intermediate Similarity NPC256846
0.8088 Intermediate Similarity NPC139397
0.806 Intermediate Similarity NPC475523
0.8033 Intermediate Similarity NPC200258
0.803 Intermediate Similarity NPC470329
0.8 Intermediate Similarity NPC202118
0.8 Intermediate Similarity NPC197238
0.8 Intermediate Similarity NPC23117
0.7971 Intermediate Similarity NPC260040
0.7971 Intermediate Similarity NPC307176
0.7971 Intermediate Similarity NPC265782
0.7971 Intermediate Similarity NPC251929
0.7971 Intermediate Similarity NPC282593
0.7971 Intermediate Similarity NPC159577
0.7971 Intermediate Similarity NPC35734
0.7971 Intermediate Similarity NPC2634
0.7966 Intermediate Similarity NPC64866
0.7941 Intermediate Similarity NPC155198
0.7937 Intermediate Similarity NPC94991
0.7937 Intermediate Similarity NPC266295
0.7903 Intermediate Similarity NPC20603
0.7869 Intermediate Similarity NPC5626
0.7857 Intermediate Similarity NPC115023
0.7857 Intermediate Similarity NPC54123
0.7857 Intermediate Similarity NPC190035
0.7857 Intermediate Similarity NPC474562
0.7812 Intermediate Similarity NPC259261
0.7797 Intermediate Similarity NPC116906
0.7797 Intermediate Similarity NPC32351
0.7794 Intermediate Similarity NPC4370
0.7794 Intermediate Similarity NPC290350
0.7778 Intermediate Similarity NPC192427
0.7778 Intermediate Similarity NPC193695
0.7746 Intermediate Similarity NPC56747
0.7746 Intermediate Similarity NPC109576
0.7746 Intermediate Similarity NPC130016
0.7746 Intermediate Similarity NPC303613
0.7746 Intermediate Similarity NPC474228
0.7746 Intermediate Similarity NPC470044
0.7746 Intermediate Similarity NPC470045
0.7746 Intermediate Similarity NPC251705
0.7746 Intermediate Similarity NPC180015
0.7727 Intermediate Similarity NPC32285
0.7727 Intermediate Similarity NPC472306
0.7705 Intermediate Similarity NPC14002
0.7692 Intermediate Similarity NPC25853
0.7681 Intermediate Similarity NPC39157
0.7681 Intermediate Similarity NPC82477
0.7681 Intermediate Similarity NPC296697
0.7681 Intermediate Similarity NPC142754
0.7681 Intermediate Similarity NPC20610
0.7667 Intermediate Similarity NPC236623
0.7656 Intermediate Similarity NPC30215
0.7647 Intermediate Similarity NPC323005
0.7619 Intermediate Similarity NPC473733
0.7606 Intermediate Similarity NPC234707
0.7606 Intermediate Similarity NPC225467
0.7606 Intermediate Similarity NPC5701
0.7571 Intermediate Similarity NPC286814
0.7571 Intermediate Similarity NPC182815
0.7538 Intermediate Similarity NPC143834
0.7536 Intermediate Similarity NPC20181
0.7536 Intermediate Similarity NPC220210
0.7534 Intermediate Similarity NPC293803
0.7534 Intermediate Similarity NPC65650
0.7534 Intermediate Similarity NPC476346
0.7534 Intermediate Similarity NPC473171
0.75 Intermediate Similarity NPC176819
0.75 Intermediate Similarity NPC49575
0.75 Intermediate Similarity NPC55004
0.75 Intermediate Similarity NPC58970
0.75 Intermediate Similarity NPC163984
0.75 Intermediate Similarity NPC267626
0.75 Intermediate Similarity NPC230823
0.746 Intermediate Similarity NPC275472
0.7458 Intermediate Similarity NPC91962
0.7432 Intermediate Similarity NPC180886
0.7432 Intermediate Similarity NPC69408
0.7432 Intermediate Similarity NPC1254
0.7419 Intermediate Similarity NPC474141
0.7397 Intermediate Similarity NPC474797
0.7397 Intermediate Similarity NPC255021
0.7397 Intermediate Similarity NPC309852
0.7397 Intermediate Similarity NPC329866
0.7397 Intermediate Similarity NPC474796
0.7385 Intermediate Similarity NPC60772
0.7377 Intermediate Similarity NPC27438
0.7361 Intermediate Similarity NPC21944
0.7361 Intermediate Similarity NPC304983
0.7361 Intermediate Similarity NPC470078
0.7361 Intermediate Similarity NPC181204
0.7361 Intermediate Similarity NPC133253
0.7361 Intermediate Similarity NPC305501
0.7353 Intermediate Similarity NPC4638
0.7353 Intermediate Similarity NPC473902
0.7333 Intermediate Similarity NPC266193
0.7333 Intermediate Similarity NPC257666
0.7333 Intermediate Similarity NPC472300
0.7313 Intermediate Similarity NPC475795
0.7313 Intermediate Similarity NPC97322
0.7302 Intermediate Similarity NPC202850
0.7302 Intermediate Similarity NPC63396
0.7302 Intermediate Similarity NPC250539
0.7297 Intermediate Similarity NPC114236
0.7286 Intermediate Similarity NPC193770
0.726 Intermediate Similarity NPC474488
0.7237 Intermediate Similarity NPC115515
0.7237 Intermediate Similarity NPC74410
0.7237 Intermediate Similarity NPC471409
0.7237 Intermediate Similarity NPC189485
0.7237 Intermediate Similarity NPC275494
0.7222 Intermediate Similarity NPC477856
0.7222 Intermediate Similarity NPC214770
0.7213 Intermediate Similarity NPC228776
0.7206 Intermediate Similarity NPC167256
0.72 Intermediate Similarity NPC469796
0.72 Intermediate Similarity NPC469793
0.72 Intermediate Similarity NPC470525
0.72 Intermediate Similarity NPC263582
0.7179 Intermediate Similarity NPC136150
0.7164 Intermediate Similarity NPC270042
0.7162 Intermediate Similarity NPC128346
0.7162 Intermediate Similarity NPC20025
0.7162 Intermediate Similarity NPC211641
0.7162 Intermediate Similarity NPC219232
0.7143 Intermediate Similarity NPC176171
0.7143 Intermediate Similarity NPC92327
0.7143 Intermediate Similarity NPC90965
0.7143 Intermediate Similarity NPC37644
0.7143 Intermediate Similarity NPC295777
0.7143 Intermediate Similarity NPC27817
0.7143 Intermediate Similarity NPC296311
0.7143 Intermediate Similarity NPC170793
0.7143 Intermediate Similarity NPC69898
0.7123 Intermediate Similarity NPC223187
0.7119 Intermediate Similarity NPC114239
0.7119 Intermediate Similarity NPC13991
0.7119 Intermediate Similarity NPC241784
0.7105 Intermediate Similarity NPC197659
0.7105 Intermediate Similarity NPC97377
0.7105 Intermediate Similarity NPC165711
0.7101 Intermediate Similarity NPC150162
0.7083 Intermediate Similarity NPC61702
0.7083 Intermediate Similarity NPC162867
0.7067 Intermediate Similarity NPC255650
0.7051 Intermediate Similarity NPC476809
0.7051 Intermediate Similarity NPC108955
0.7051 Intermediate Similarity NPC474509
0.7051 Intermediate Similarity NPC2482
0.7042 Intermediate Similarity NPC176107
0.7031 Intermediate Similarity NPC100809
0.7031 Intermediate Similarity NPC209431
0.7013 Intermediate Similarity NPC478246
0.7013 Intermediate Similarity NPC475994
0.7013 Intermediate Similarity NPC62336
0.7013 Intermediate Similarity NPC469996
0.7013 Intermediate Similarity NPC228911
0.7013 Intermediate Similarity NPC478247
0.7 Intermediate Similarity NPC268039
0.7 Intermediate Similarity NPC236355
0.7 Intermediate Similarity NPC4079
0.7 Intermediate Similarity NPC14917
0.6986 Remote Similarity NPC40574
0.6984 Remote Similarity NPC22182
0.6974 Remote Similarity NPC76966
0.6974 Remote Similarity NPC19907
0.6974 Remote Similarity NPC151622
0.6974 Remote Similarity NPC472305
0.6974 Remote Similarity NPC7629
0.6974 Remote Similarity NPC186554
0.6962 Remote Similarity NPC472684
0.6962 Remote Similarity NPC149237
0.6962 Remote Similarity NPC55869

  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 NPC6697 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
0.9153 High Similarity NPD287 Approved
0.8088 Intermediate Similarity NPD4137 Phase 3
0.7971 Intermediate Similarity NPD4691 Approved
0.7971 Intermediate Similarity NPD4747 Approved
0.7681 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD5733 Approved
0.7639 Intermediate Similarity NPD4058 Approved
0.7639 Intermediate Similarity NPD4687 Approved
0.7606 Intermediate Similarity NPD5276 Approved
0.6875 Remote Similarity NPD4223 Phase 3
0.6875 Remote Similarity NPD4221 Approved
0.6835 Remote Similarity NPD4695 Discontinued
0.679 Remote Similarity NPD3527 Clinical (unspecified phase)
0.675 Remote Similarity NPD8028 Phase 2
0.6707 Remote Similarity NPD3665 Phase 1
0.6707 Remote Similarity NPD3133 Approved
0.6707 Remote Similarity NPD3666 Approved
0.6707 Remote Similarity NPD4197 Approved
0.6667 Remote Similarity NPD7331 Phase 2
0.6627 Remote Similarity NPD5329 Approved
0.6582 Remote Similarity NPD3617 Approved
0.6548 Remote Similarity NPD4694 Approved
0.6548 Remote Similarity NPD4138 Approved
0.6548 Remote Similarity NPD4693 Phase 3
0.6548 Remote Similarity NPD7521 Approved
0.6548 Remote Similarity NPD5690 Phase 2
0.6548 Remote Similarity NPD4519 Discontinued
0.6548 Remote Similarity NPD3618 Phase 1
0.6548 Remote Similarity NPD5280 Approved
0.6548 Remote Similarity NPD4689 Approved
0.6548 Remote Similarity NPD7334 Approved
0.6548 Remote Similarity NPD4688 Approved
0.6548 Remote Similarity NPD5205 Approved
0.6548 Remote Similarity NPD4623 Approved
0.6548 Remote Similarity NPD4690 Approved
0.6548 Remote Similarity NPD7146 Approved
0.6548 Remote Similarity NPD6409 Approved
0.6548 Remote Similarity NPD6684 Approved
0.6548 Remote Similarity NPD5330 Approved
0.6471 Remote Similarity NPD3573 Approved
0.6463 Remote Similarity NPD3667 Approved
0.6395 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6395 Remote Similarity NPD6903 Approved
0.6395 Remote Similarity NPD5737 Approved
0.6395 Remote Similarity NPD5208 Approved
0.6395 Remote Similarity NPD6672 Approved
0.6353 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6353 Remote Similarity NPD5279 Phase 3
0.6322 Remote Similarity NPD6673 Approved
0.6322 Remote Similarity NPD6904 Approved
0.6322 Remote Similarity NPD6080 Approved
0.6322 Remote Similarity NPD5328 Approved
0.6322 Remote Similarity NPD4753 Phase 2
0.631 Remote Similarity NPD4786 Approved
0.631 Remote Similarity NPD3668 Phase 3
0.6301 Remote Similarity NPD7341 Phase 2
0.625 Remote Similarity NPD5207 Approved
0.625 Remote Similarity NPD5692 Phase 3
0.618 Remote Similarity NPD5284 Approved
0.618 Remote Similarity NPD5693 Phase 1
0.618 Remote Similarity NPD5694 Approved
0.618 Remote Similarity NPD5281 Approved
0.618 Remote Similarity NPD6050 Approved
0.618 Remote Similarity NPD7515 Phase 2
0.618 Remote Similarity NPD6079 Approved
0.6163 Remote Similarity NPD6098 Approved
0.6136 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6111 Remote Similarity NPD4193 Approved
0.6111 Remote Similarity NPD4194 Approved
0.6111 Remote Similarity NPD4192 Approved
0.6111 Remote Similarity NPD4202 Approved
0.6111 Remote Similarity NPD4191 Approved
0.6098 Remote Similarity NPD4195 Approved
0.6071 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6067 Remote Similarity NPD4096 Approved
0.6066 Remote Similarity NPD1799 Clinical (unspecified phase)
0.6047 Remote Similarity NPD1694 Approved
0.6044 Remote Similarity NPD6001 Approved
0.6044 Remote Similarity NPD7900 Approved
0.6044 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6044 Remote Similarity NPD7748 Approved
0.6024 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6023 Remote Similarity NPD4518 Approved
0.5978 Remote Similarity NPD4629 Approved
0.5978 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5978 Remote Similarity NPD5695 Phase 3
0.5978 Remote Similarity NPD5210 Approved
0.5952 Remote Similarity NPD4139 Approved
0.5952 Remote Similarity NPD4692 Approved
0.5942 Remote Similarity NPD4627 Clinical (unspecified phase)
0.5934 Remote Similarity NPD5133 Approved
0.5914 Remote Similarity NPD5221 Approved
0.5914 Remote Similarity NPD4697 Phase 3
0.5914 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5914 Remote Similarity NPD5222 Approved
0.5862 Remote Similarity NPD1696 Phase 3
0.5851 Remote Similarity NPD5173 Approved
0.5851 Remote Similarity NPD4755 Approved
0.5851 Remote Similarity NPD3495 Discontinued
0.5851 Remote Similarity NPD6084 Phase 2
0.5851 Remote Similarity NPD6083 Phase 2
0.5851 Remote Similarity NPD7902 Approved
0.5811 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5806 Remote Similarity NPD5654 Approved
0.5802 Remote Similarity NPD8039 Approved
0.5789 Remote Similarity NPD5696 Approved
0.5789 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5763 Remote Similarity NPD319 Phase 1
0.5761 Remote Similarity NPD7631 Approved
0.5761 Remote Similarity NPD6399 Phase 3
0.5745 Remote Similarity NPD7614 Phase 1
0.5745 Remote Similarity NPD7732 Phase 3
0.5729 Remote Similarity NPD4700 Approved
0.5729 Remote Similarity NPD5285 Approved
0.5729 Remote Similarity NPD5286 Approved
0.5729 Remote Similarity NPD4696 Approved
0.5692 Remote Similarity NPD345 Approved
0.5692 Remote Similarity NPD344 Approved
0.5692 Remote Similarity NPD343 Approved
0.5684 Remote Similarity NPD5959 Approved
0.567 Remote Similarity NPD5223 Approved
0.5652 Remote Similarity NPD7609 Phase 3
0.5634 Remote Similarity NPD4219 Approved
0.5632 Remote Similarity NPD4788 Approved
0.5625 Remote Similarity NPD4243 Approved
0.5612 Remote Similarity NPD5226 Approved
0.5612 Remote Similarity NPD5211 Phase 2
0.5612 Remote Similarity NPD5224 Approved
0.5612 Remote Similarity NPD4633 Approved
0.5612 Remote Similarity NPD5091 Approved
0.5612 Remote Similarity NPD5225 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