Structure

Physi-Chem Properties

Molecular Weight:  406.27
Volume:  439.952
LogP:  3.965
LogD:  3.029
LogS:  -4.393
# Rotatable Bonds:  8
TPSA:  72.83
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.51
Synthetic Accessibility Score:  4.795
Fsp3:  0.75
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:  -4.692
MDCK Permeability:  1.952372258529067e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.033
20% Bioavailability (F20%):  0.031
30% Bioavailability (F30%):  0.084

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.639
Plasma Protein Binding (PPB):  85.20824432373047%
Volume Distribution (VD):  1.879
Pgp-substrate:  14.159104347229004%

ADMET: Metabolism

CYP1A2-inhibitor:  0.063
CYP1A2-substrate:  0.154
CYP2C19-inhibitor:  0.208
CYP2C19-substrate:  0.746
CYP2C9-inhibitor:  0.289
CYP2C9-substrate:  0.108
CYP2D6-inhibitor:  0.3
CYP2D6-substrate:  0.054
CYP3A4-inhibitor:  0.901
CYP3A4-substrate:  0.475

ADMET: Excretion

Clearance (CL):  2.236
Half-life (T1/2):  0.091

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.394
Drug-inuced Liver Injury (DILI):  0.824
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.109
Maximum Recommended Daily Dose:  0.04
Skin Sensitization:  0.084
Carcinogencity:  0.452
Eye Corrosion:  0.162
Eye Irritation:  0.134
Respiratory Toxicity:  0.944

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

  Natural Product: NPC131329

Natural Product ID:  NPC131329
Common Name*:   Vitetrifolin D
IUPAC Name:   [(1S,2R,3S,4R)-1-acetyloxy-4-(3-hydroxy-3-methylpent-4-enyl)-3,4,8,8-tetramethyl-1,2,3,5,6,7-hexahydronaphthalen-2-yl] acetate
Synonyms:  
Standard InCHIKey:  JSGVRMXIAILPPO-FWPWNEHFSA-N
Standard InCHI:  InChI=1S/C24H38O5/c1-9-23(7,27)13-14-24(8)15(2)20(28-16(3)25)21(29-17(4)26)19-18(24)11-10-12-22(19,5)6/h9,15,20-21,27H,1,10-14H2,2-8H3/t15-,20-,21+,23?,24-/m1/s1
SMILES:  C=CC(CC[C@]1(C)[C@H](C)[C@@H](OC(=O)C)[C@H](C2=C1CCCC2(C)C)OC(=O)C)(O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2436600
PubChem CID:   11015016
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000346] Dicarboxylic acids and derivatives

*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
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota Fruits n.a. n.a. PMID[10579867]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota subterranean part n.a. n.a. PMID[11374949]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. fruit n.a. PMID[11536386]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[11975496]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[12828478]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. root n.a. PMID[15520511]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. fruit n.a. PMID[15577254]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[15620254]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[15621610]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[1624939]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17027268]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19715321]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19931461]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[23327905]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23403897]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[24035341]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[28453270]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14602 Vitex negundo Species Lamiaceae 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
NPT113 Cell Line RAW264.7 Mus musculus Activity > 90.0 % PMID[543619]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 24500.0 nM PMID[543619]

☑ 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 NPC131329 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
0.9759 High Similarity NPC20946
0.9518 High Similarity NPC245004
0.9048 High Similarity NPC35933
0.8916 High Similarity NPC471408
0.8851 High Similarity NPC246028
0.881 High Similarity NPC49208
0.8795 High Similarity NPC25554
0.8652 High Similarity NPC477574
0.8588 High Similarity NPC23748
0.8478 Intermediate Similarity NPC57664
0.8471 Intermediate Similarity NPC256112
0.8462 Intermediate Similarity NPC472416
0.8462 Intermediate Similarity NPC472360
0.8452 Intermediate Similarity NPC233332
0.8444 Intermediate Similarity NPC177641
0.8427 Intermediate Similarity NPC82876
0.8409 Intermediate Similarity NPC166857
0.8387 Intermediate Similarity NPC473244
0.8372 Intermediate Similarity NPC476927
0.8352 Intermediate Similarity NPC53555
0.8333 Intermediate Similarity NPC78973
0.8333 Intermediate Similarity NPC242767
0.828 Intermediate Similarity NPC284194
0.828 Intermediate Similarity NPC221801
0.828 Intermediate Similarity NPC471765
0.828 Intermediate Similarity NPC211810
0.8229 Intermediate Similarity NPC11956
0.8222 Intermediate Similarity NPC16265
0.8211 Intermediate Similarity NPC473510
0.8211 Intermediate Similarity NPC38855
0.8191 Intermediate Similarity NPC210337
0.8152 Intermediate Similarity NPC27918
0.8144 Intermediate Similarity NPC23584
0.814 Intermediate Similarity NPC142163
0.814 Intermediate Similarity NPC170303
0.8132 Intermediate Similarity NPC220216
0.8125 Intermediate Similarity NPC472554
0.8118 Intermediate Similarity NPC233295
0.8105 Intermediate Similarity NPC247233
0.8095 Intermediate Similarity NPC283619
0.8095 Intermediate Similarity NPC40049
0.809 Intermediate Similarity NPC475069
0.809 Intermediate Similarity NPC175145
0.8085 Intermediate Similarity NPC88009
0.8085 Intermediate Similarity NPC129569
0.8068 Intermediate Similarity NPC306951
0.8065 Intermediate Similarity NPC474922
0.8065 Intermediate Similarity NPC182826
0.8065 Intermediate Similarity NPC105375
0.8061 Intermediate Similarity NPC473543
0.8046 Intermediate Similarity NPC2524
0.8046 Intermediate Similarity NPC471218
0.8043 Intermediate Similarity NPC124374
0.8043 Intermediate Similarity NPC41239
0.8043 Intermediate Similarity NPC329842
0.8041 Intermediate Similarity NPC472552
0.8022 Intermediate Similarity NPC261320
0.8021 Intermediate Similarity NPC230546
0.8 Intermediate Similarity NPC471779
0.8 Intermediate Similarity NPC254496
0.7979 Intermediate Similarity NPC276110
0.7978 Intermediate Similarity NPC109528
0.7976 Intermediate Similarity NPC265588
0.7959 Intermediate Similarity NPC473523
0.7957 Intermediate Similarity NPC99653
0.7957 Intermediate Similarity NPC7349
0.7955 Intermediate Similarity NPC474789
0.7955 Intermediate Similarity NPC52108
0.7955 Intermediate Similarity NPC474809
0.7938 Intermediate Similarity NPC475617
0.7931 Intermediate Similarity NPC159148
0.7912 Intermediate Similarity NPC473879
0.7912 Intermediate Similarity NPC24816
0.7907 Intermediate Similarity NPC100906
0.79 Intermediate Similarity NPC301666
0.7895 Intermediate Similarity NPC190713
0.7895 Intermediate Similarity NPC473153
0.7889 Intermediate Similarity NPC329692
0.7889 Intermediate Similarity NPC473226
0.7889 Intermediate Similarity NPC131813
0.7889 Intermediate Similarity NPC474970
0.7889 Intermediate Similarity NPC471219
0.7889 Intermediate Similarity NPC281316
0.7872 Intermediate Similarity NPC469491
0.7872 Intermediate Similarity NPC105490
0.7865 Intermediate Similarity NPC102048
0.7865 Intermediate Similarity NPC302360
0.7857 Intermediate Similarity NPC476471
0.7857 Intermediate Similarity NPC475344
0.7849 Intermediate Similarity NPC303697
0.7849 Intermediate Similarity NPC234335
0.7849 Intermediate Similarity NPC472811
0.7841 Intermediate Similarity NPC155521
0.7841 Intermediate Similarity NPC474979
0.7835 Intermediate Similarity NPC188968
0.7835 Intermediate Similarity NPC79303
0.7835 Intermediate Similarity NPC474190
0.7835 Intermediate Similarity NPC271295
0.7826 Intermediate Similarity NPC49783
0.7826 Intermediate Similarity NPC473647
0.7826 Intermediate Similarity NPC314727
0.7826 Intermediate Similarity NPC115607
0.7822 Intermediate Similarity NPC50124
0.7816 Intermediate Similarity NPC281880
0.7816 Intermediate Similarity NPC474592
0.7816 Intermediate Similarity NPC469802
0.7816 Intermediate Similarity NPC269791
0.7812 Intermediate Similarity NPC73911
0.7812 Intermediate Similarity NPC141401
0.7812 Intermediate Similarity NPC205143
0.7812 Intermediate Similarity NPC285513
0.7802 Intermediate Similarity NPC149224
0.7802 Intermediate Similarity NPC476948
0.7789 Intermediate Similarity NPC134067
0.7789 Intermediate Similarity NPC476720
0.7789 Intermediate Similarity NPC472441
0.7789 Intermediate Similarity NPC53565
0.7778 Intermediate Similarity NPC474124
0.7778 Intermediate Similarity NPC274448
0.7778 Intermediate Similarity NPC474013
0.7778 Intermediate Similarity NPC164424
0.7778 Intermediate Similarity NPC477578
0.7766 Intermediate Similarity NPC205034
0.7766 Intermediate Similarity NPC162615
0.7766 Intermediate Similarity NPC472812
0.7766 Intermediate Similarity NPC152778
0.7766 Intermediate Similarity NPC38232
0.7755 Intermediate Similarity NPC280991
0.7755 Intermediate Similarity NPC473160
0.7755 Intermediate Similarity NPC303559
0.7753 Intermediate Similarity NPC57370
0.7753 Intermediate Similarity NPC79945
0.7745 Intermediate Similarity NPC5475
0.7745 Intermediate Similarity NPC472216
0.7745 Intermediate Similarity NPC475586
0.7745 Intermediate Similarity NPC284828
0.7745 Intermediate Similarity NPC173905
0.7742 Intermediate Similarity NPC473269
0.7742 Intermediate Similarity NPC48732
0.7742 Intermediate Similarity NPC182136
0.7742 Intermediate Similarity NPC310479
0.7742 Intermediate Similarity NPC221111
0.7742 Intermediate Similarity NPC295668
0.7742 Intermediate Similarity NPC472307
0.7742 Intermediate Similarity NPC280149
0.7738 Intermediate Similarity NPC71152
0.7738 Intermediate Similarity NPC104644
0.7732 Intermediate Similarity NPC218107
0.7732 Intermediate Similarity NPC478056
0.7732 Intermediate Similarity NPC278386
0.7732 Intermediate Similarity NPC92275
0.7732 Intermediate Similarity NPC124512
0.7732 Intermediate Similarity NPC316598
0.7732 Intermediate Similarity NPC159763
0.7727 Intermediate Similarity NPC475944
0.7723 Intermediate Similarity NPC475176
0.7723 Intermediate Similarity NPC67321
0.7723 Intermediate Similarity NPC187435
0.7717 Intermediate Similarity NPC93411
0.7717 Intermediate Similarity NPC7280
0.7717 Intermediate Similarity NPC477128
0.7717 Intermediate Similarity NPC229612
0.7708 Intermediate Similarity NPC276103
0.7708 Intermediate Similarity NPC288970
0.7708 Intermediate Similarity NPC54248
0.7708 Intermediate Similarity NPC16967
0.7701 Intermediate Similarity NPC471537
0.77 Intermediate Similarity NPC118911
0.7692 Intermediate Similarity NPC73038
0.7692 Intermediate Similarity NPC82979
0.7692 Intermediate Similarity NPC255143
0.7692 Intermediate Similarity NPC286153
0.7692 Intermediate Similarity NPC102996
0.7684 Intermediate Similarity NPC57117
0.7684 Intermediate Similarity NPC215700
0.7684 Intermediate Similarity NPC470255
0.7684 Intermediate Similarity NPC298973
0.7684 Intermediate Similarity NPC38830
0.7684 Intermediate Similarity NPC279410
0.7684 Intermediate Similarity NPC119562
0.7684 Intermediate Similarity NPC91010
0.7684 Intermediate Similarity NPC201725
0.7684 Intermediate Similarity NPC104925
0.7677 Intermediate Similarity NPC137430
0.7677 Intermediate Similarity NPC472815
0.7677 Intermediate Similarity NPC273668
0.7677 Intermediate Similarity NPC471363
0.7677 Intermediate Similarity NPC258547
0.7677 Intermediate Similarity NPC80781
0.7677 Intermediate Similarity NPC283343
0.7677 Intermediate Similarity NPC238397
0.7677 Intermediate Similarity NPC470571
0.7674 Intermediate Similarity NPC132542
0.7674 Intermediate Similarity NPC91594
0.7667 Intermediate Similarity NPC83702
0.7667 Intermediate Similarity NPC96055
0.7667 Intermediate Similarity NPC46320
0.7667 Intermediate Similarity NPC470077
0.766 Intermediate Similarity NPC72845
0.766 Intermediate Similarity NPC26888

  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 NPC131329 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
0.7732 Intermediate Similarity NPD4225 Approved
0.7475 Intermediate Similarity NPD7640 Approved
0.7475 Intermediate Similarity NPD7639 Approved
0.7442 Intermediate Similarity NPD8264 Approved
0.7407 Intermediate Similarity NPD7115 Discovery
0.74 Intermediate Similarity NPD5344 Discontinued
0.7374 Intermediate Similarity NPD7638 Approved
0.73 Intermediate Similarity NPD6648 Approved
0.7263 Intermediate Similarity NPD6051 Approved
0.7216 Intermediate Similarity NPD5779 Approved
0.7216 Intermediate Similarity NPD5778 Approved
0.7143 Intermediate Similarity NPD7748 Approved
0.7113 Intermediate Similarity NPD6411 Approved
0.7097 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD6399 Phase 3
0.7021 Intermediate Similarity NPD1694 Approved
0.699 Remote Similarity NPD7632 Discontinued
0.6939 Remote Similarity NPD7515 Phase 2
0.6931 Remote Similarity NPD7902 Approved
0.6923 Remote Similarity NPD7645 Phase 2
0.6916 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6907 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6907 Remote Similarity NPD6101 Approved
0.6852 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6848 Remote Similarity NPD7525 Registered
0.6768 Remote Similarity NPD7637 Suspended
0.6727 Remote Similarity NPD8297 Approved
0.6726 Remote Similarity NPD7328 Approved
0.6726 Remote Similarity NPD7327 Approved
0.6702 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6701 Remote Similarity NPD7524 Approved
0.6699 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7503 Approved
0.6696 Remote Similarity NPD8033 Approved
0.6667 Remote Similarity NPD7516 Approved
0.6667 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6899 Approved
0.6667 Remote Similarity NPD6942 Approved
0.6667 Remote Similarity NPD7339 Approved
0.6667 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7838 Discovery
0.6667 Remote Similarity NPD6881 Approved
0.6667 Remote Similarity NPD8039 Approved
0.6636 Remote Similarity NPD6675 Approved
0.6636 Remote Similarity NPD6402 Approved
0.6636 Remote Similarity NPD7128 Approved
0.6636 Remote Similarity NPD5739 Approved
0.6634 Remote Similarity NPD7900 Approved
0.6634 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6632 Remote Similarity NPD6695 Phase 3
0.6609 Remote Similarity NPD8377 Approved
0.6609 Remote Similarity NPD8294 Approved
0.6593 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6574 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6574 Remote Similarity NPD5697 Approved
0.6571 Remote Similarity NPD4159 Approved
0.6569 Remote Similarity NPD5695 Phase 3
0.6562 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4786 Approved
0.6552 Remote Similarity NPD8335 Approved
0.6552 Remote Similarity NPD8380 Approved
0.6552 Remote Similarity NPD8379 Approved
0.6552 Remote Similarity NPD8378 Approved
0.6552 Remote Similarity NPD8296 Approved
0.6545 Remote Similarity NPD7102 Approved
0.6545 Remote Similarity NPD6883 Approved
0.6545 Remote Similarity NPD7290 Approved
0.6531 Remote Similarity NPD3573 Approved
0.6531 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6526 Remote Similarity NPD3667 Approved
0.6514 Remote Similarity NPD7320 Approved
0.6514 Remote Similarity NPD6686 Approved
0.6514 Remote Similarity NPD6011 Approved
0.6505 Remote Similarity NPD4792 Clinical (unspecified phase)
0.65 Remote Similarity NPD6698 Approved
0.65 Remote Similarity NPD46 Approved
0.65 Remote Similarity NPD5785 Approved
0.6489 Remote Similarity NPD4821 Approved
0.6489 Remote Similarity NPD4822 Approved
0.6489 Remote Similarity NPD4820 Approved
0.6489 Remote Similarity NPD4748 Discontinued
0.6489 Remote Similarity NPD4819 Approved
0.6489 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6486 Remote Similarity NPD6869 Approved
0.6486 Remote Similarity NPD6649 Approved
0.6486 Remote Similarity NPD6617 Approved
0.6486 Remote Similarity NPD8130 Phase 1
0.6486 Remote Similarity NPD6847 Approved
0.6486 Remote Similarity NPD6650 Approved
0.6458 Remote Similarity NPD5362 Discontinued
0.6458 Remote Similarity NPD7154 Phase 3
0.6455 Remote Similarity NPD6372 Approved
0.6455 Remote Similarity NPD6012 Approved
0.6455 Remote Similarity NPD6013 Approved
0.6455 Remote Similarity NPD6373 Approved
0.6455 Remote Similarity NPD6014 Approved
0.6455 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6452 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6452 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6442 Remote Similarity NPD6084 Phase 2
0.6442 Remote Similarity NPD6083 Phase 2
0.6436 Remote Similarity NPD8034 Phase 2
0.6436 Remote Similarity NPD6079 Approved
0.6436 Remote Similarity NPD8035 Phase 2
0.6429 Remote Similarity NPD6684 Approved
0.6429 Remote Similarity NPD6409 Approved
0.6429 Remote Similarity NPD368 Approved
0.6429 Remote Similarity NPD3618 Phase 1
0.6429 Remote Similarity NPD7521 Approved
0.6429 Remote Similarity NPD5330 Approved
0.6429 Remote Similarity NPD6882 Approved
0.6429 Remote Similarity NPD7334 Approved
0.6429 Remote Similarity NPD7146 Approved
0.6422 Remote Similarity NPD5701 Approved
0.6413 Remote Similarity NPD6933 Approved
0.641 Remote Similarity NPD8513 Phase 3
0.641 Remote Similarity NPD8516 Approved
0.641 Remote Similarity NPD8515 Approved
0.641 Remote Similarity NPD8517 Approved
0.64 Remote Similarity NPD5328 Approved
0.64 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6395 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6374 Remote Similarity NPD4784 Approved
0.6374 Remote Similarity NPD6926 Approved
0.6374 Remote Similarity NPD4785 Approved
0.6374 Remote Similarity NPD6924 Approved
0.6372 Remote Similarity NPD4632 Approved
0.6364 Remote Similarity NPD7750 Discontinued
0.6355 Remote Similarity NPD5211 Phase 2
0.6339 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6333 Remote Similarity NPD7507 Approved
0.6327 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6327 Remote Similarity NPD1696 Phase 3
0.6327 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6931 Approved
0.6316 Remote Similarity NPD6930 Phase 2
0.6316 Remote Similarity NPD7332 Phase 2
0.6316 Remote Similarity NPD7514 Phase 3
0.6316 Remote Similarity NPD8259 Clinical (unspecified phase)
0.63 Remote Similarity NPD7513 Clinical (unspecified phase)
0.63 Remote Similarity NPD6903 Approved
0.63 Remote Similarity NPD5737 Approved
0.63 Remote Similarity NPD6672 Approved
0.6289 Remote Similarity NPD5331 Approved
0.6289 Remote Similarity NPD5332 Approved
0.6283 Remote Similarity NPD6053 Discontinued
0.6277 Remote Similarity NPD4268 Approved
0.6277 Remote Similarity NPD4271 Approved
0.6275 Remote Similarity NPD5281 Approved
0.6275 Remote Similarity NPD5693 Phase 1
0.6275 Remote Similarity NPD7983 Approved
0.6275 Remote Similarity NPD5284 Approved
0.6263 Remote Similarity NPD4623 Approved
0.6263 Remote Similarity NPD4519 Discontinued
0.625 Remote Similarity NPD4790 Discontinued
0.625 Remote Similarity NPD6356 Clinical (unspecified phase)
0.625 Remote Similarity NPD6371 Approved
0.6239 Remote Similarity NPD5141 Approved
0.6226 Remote Similarity NPD5696 Approved
0.6224 Remote Similarity NPD3668 Phase 3
0.6214 Remote Similarity NPD4202 Approved
0.6211 Remote Similarity NPD4195 Approved
0.6211 Remote Similarity NPD6929 Approved
0.621 Remote Similarity NPD7260 Phase 2
0.6207 Remote Similarity NPD6009 Approved
0.6195 Remote Similarity NPD8413 Clinical (unspecified phase)
0.619 Remote Similarity NPD5220 Clinical (unspecified phase)
0.619 Remote Similarity NPD5222 Approved
0.619 Remote Similarity NPD5221 Approved
0.6186 Remote Similarity NPD4270 Approved
0.6186 Remote Similarity NPD6319 Approved
0.6186 Remote Similarity NPD4269 Approved
0.6182 Remote Similarity NPD6008 Approved
0.6179 Remote Similarity NPD7319 Approved
0.6168 Remote Similarity NPD5286 Approved
0.6168 Remote Similarity NPD4696 Approved
0.6168 Remote Similarity NPD5285 Approved
0.6167 Remote Similarity NPD7604 Phase 2
0.6154 Remote Similarity NPD7152 Approved
0.6154 Remote Similarity NPD4243 Approved
0.6154 Remote Similarity NPD7150 Approved
0.6154 Remote Similarity NPD7151 Approved
0.6154 Remote Similarity NPD6335 Approved
0.6148 Remote Similarity NPD8074 Phase 3
0.6146 Remote Similarity NPD7509 Discontinued
0.6134 Remote Similarity NPD5983 Phase 2
0.6132 Remote Similarity NPD4755 Approved
0.6132 Remote Similarity NPD5173 Approved
0.6121 Remote Similarity NPD6868 Approved
0.6117 Remote Similarity NPD6050 Approved
0.6117 Remote Similarity NPD5694 Approved
0.6117 Remote Similarity NPD7087 Discontinued
0.6116 Remote Similarity NPD7492 Approved
0.6111 Remote Similarity NPD5223 Approved
0.6105 Remote Similarity NPD7145 Approved
0.6102 Remote Similarity NPD7101 Approved
0.6102 Remote Similarity NPD7100 Approved
0.61 Remote Similarity NPD3574 Clinical (unspecified phase)
0.61 Remote Similarity NPD6098 Approved
0.61 Remote Similarity NPD5786 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