Structure

Physi-Chem Properties

Molecular Weight:  382.21
Volume:  408.776
LogP:  4.478
LogD:  4.02
LogS:  -4.908
# Rotatable Bonds:  3
TPSA:  59.67
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.603
Synthetic Accessibility Score:  3.874
Fsp3:  0.542
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:  -4.744
MDCK Permeability:  1.9246777810622007e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.946
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.503
30% Bioavailability (F30%):  0.9

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.177
Plasma Protein Binding (PPB):  92.96102142333984%
Volume Distribution (VD):  1.038
Pgp-substrate:  7.013547420501709%

ADMET: Metabolism

CYP1A2-inhibitor:  0.333
CYP1A2-substrate:  0.462
CYP2C19-inhibitor:  0.334
CYP2C19-substrate:  0.213
CYP2C9-inhibitor:  0.522
CYP2C9-substrate:  0.864
CYP2D6-inhibitor:  0.41
CYP2D6-substrate:  0.897
CYP3A4-inhibitor:  0.283
CYP3A4-substrate:  0.307

ADMET: Excretion

Clearance (CL):  9.452
Half-life (T1/2):  0.057

ADMET: Toxicity

hERG Blockers:  0.189
Human Hepatotoxicity (H-HT):  0.179
Drug-inuced Liver Injury (DILI):  0.169
AMES Toxicity:  0.016
Rat Oral Acute Toxicity:  0.656
Maximum Recommended Daily Dose:  0.983
Skin Sensitization:  0.199
Carcinogencity:  0.2
Eye Corrosion:  0.004
Eye Irritation:  0.404
Respiratory Toxicity:  0.954

Download Data

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

  Natural Product: NPC138149

Natural Product ID:  NPC138149
Common Name*:   Farnesiferol A
IUPAC Name:   7-[[(1S,4aS,6R,8aR)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methoxy]chromen-2-one
Synonyms:  
Standard InCHIKey:  FCWYNTDTQPCVPG-WTMJVXIESA-N
Standard InCHI:  InChI=1S/C24H30O4/c1-15-5-9-20-23(2,3)21(25)11-12-24(20,4)18(15)14-27-17-8-6-16-7-10-22(26)28-19(16)13-17/h6-8,10,13,18,20-21,25H,1,5,9,11-12,14H2,2-4H3/t18-,20+,21+,24-/m0/s1
SMILES:  C=C1CC[C@@H]2C(C)(C)[C@@H](CC[C@@]2(C)[C@H]1COc1ccc2ccc(=O)oc2c1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1078138
PubChem CID:   7067262
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins 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
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. leaf n.a. DOI[10.1021/np50070a005]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[18177011]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[19271742]
NPO10996 Ferula assa-foetida Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[19691312]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota leaves Botanical Garden of Innsbruck, Austria n.a. PMID[20100662]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[20590154]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. leaf n.a. PMID[21443171]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. leaf n.a. PMID[21923134]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[8064299]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[8064299]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3083 Ferula assafoetida Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3083 Ferula assafoetida Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3083 Ferula assafoetida Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10996 Ferula assa-foetida Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25618 Eriobotrya japonica Species Rosaceae 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
NPT65 Cell Line HepG2 Homo sapiens IC50 = 14.89 ug.mL-1 PMID[548559]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 19.0 ug.mL-1 PMID[548559]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 15.57 ug.mL-1 PMID[548559]
NPT1031 Cell Line Ca9-22 Homo sapiens IC50 = 12.07 ug.mL-1 PMID[548559]
NPT81 Cell Line A549 Homo sapiens IC50 = 15.79 ug.mL-1 PMID[548559]
NPT742 Organism Influenza A virus Influenza A virus IC50 = 0.51 ug.mL-1 PMID[548559]
NPT742 Organism Influenza A virus Influenza A virus IC90 = 0.64 ug.mL-1 PMID[548559]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7.66 ug.mL-1 PMID[548559]

☑ 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 NPC138149 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
0.9778 High Similarity NPC93640
0.9778 High Similarity NPC20631
0.9774 High Similarity NPC131198
0.9627 High Similarity NPC306365
0.9433 High Similarity NPC146388
0.9275 High Similarity NPC155552
0.9231 High Similarity NPC146014
0.9058 High Similarity NPC14697
0.9044 High Similarity NPC31849
0.9014 High Similarity NPC43716
0.9014 High Similarity NPC106126
0.9014 High Similarity NPC108994
0.9014 High Similarity NPC101255
0.9014 High Similarity NPC475719
0.8993 High Similarity NPC307883
0.8881 High Similarity NPC258567
0.8881 High Similarity NPC469701
0.8881 High Similarity NPC121740
0.8881 High Similarity NPC224774
0.8865 High Similarity NPC287286
0.8857 High Similarity NPC279573
0.8857 High Similarity NPC144512
0.8857 High Similarity NPC137262
0.8857 High Similarity NPC37428
0.8857 High Similarity NPC278600
0.8857 High Similarity NPC35501
0.8857 High Similarity NPC47040
0.8849 High Similarity NPC38099
0.8849 High Similarity NPC26954
0.8841 High Similarity NPC50896
0.8841 High Similarity NPC224475
0.8841 High Similarity NPC326600
0.8841 High Similarity NPC62366
0.8841 High Similarity NPC213173
0.8841 High Similarity NPC204353
0.8841 High Similarity NPC180716
0.8832 High Similarity NPC194277
0.8824 High Similarity NPC113098
0.8819 High Similarity NPC471608
0.8815 High Similarity NPC469453
0.8815 High Similarity NPC185066
0.8811 High Similarity NPC251372
0.8794 High Similarity NPC312881
0.8786 High Similarity NPC232246
0.8786 High Similarity NPC153818
0.8786 High Similarity NPC155963
0.8777 High Similarity NPC472525
0.8768 High Similarity NPC291551
0.8768 High Similarity NPC205797
0.8768 High Similarity NPC1220
0.8768 High Similarity NPC141822
0.8768 High Similarity NPC241165
0.8768 High Similarity NPC142563
0.8768 High Similarity NPC469965
0.8759 High Similarity NPC272650
0.8759 High Similarity NPC29734
0.8759 High Similarity NPC267336
0.875 High Similarity NPC168710
0.8732 High Similarity NPC472523
0.8732 High Similarity NPC195357
0.8732 High Similarity NPC152771
0.8731 High Similarity NPC471827
0.8731 High Similarity NPC471828
0.8723 High Similarity NPC211110
0.8723 High Similarity NPC151946
0.8714 High Similarity NPC78746
0.8714 High Similarity NPC188380
0.8714 High Similarity NPC224543
0.8705 High Similarity NPC131950
0.8696 High Similarity NPC19157
0.8686 High Similarity NPC32463
0.8667 High Similarity NPC101894
0.8658 High Similarity NPC223720
0.8657 High Similarity NPC73413
0.8657 High Similarity NPC201667
0.8657 High Similarity NPC27671
0.8652 High Similarity NPC281014
0.8652 High Similarity NPC184861
0.8652 High Similarity NPC294456
0.8652 High Similarity NPC212124
0.8652 High Similarity NPC225106
0.8643 High Similarity NPC472424
0.8643 High Similarity NPC281241
0.8643 High Similarity NPC471625
0.8643 High Similarity NPC471909
0.8643 High Similarity NPC86892
0.8633 High Similarity NPC163557
0.8633 High Similarity NPC2363
0.8633 High Similarity NPC318400
0.8633 High Similarity NPC133956
0.8633 High Similarity NPC185777
0.8633 High Similarity NPC296624
0.8633 High Similarity NPC207002
0.8633 High Similarity NPC469955
0.8633 High Similarity NPC167111
0.8633 High Similarity NPC471910
0.8633 High Similarity NPC469952
0.8623 High Similarity NPC66430
0.8623 High Similarity NPC37009
0.8621 High Similarity NPC71739
0.8603 High Similarity NPC289316
0.8603 High Similarity NPC243688
0.86 High Similarity NPC268484
0.8582 High Similarity NPC283019
0.8582 High Similarity NPC160727
0.8582 High Similarity NPC315807
0.8582 High Similarity NPC149320
0.8582 High Similarity NPC177281
0.8582 High Similarity NPC471630
0.8582 High Similarity NPC472518
0.8582 High Similarity NPC109675
0.8582 High Similarity NPC283331
0.8582 High Similarity NPC128529
0.8582 High Similarity NPC55615
0.8582 High Similarity NPC476455
0.8582 High Similarity NPC273772
0.8571 High Similarity NPC84894
0.8571 High Similarity NPC195343
0.8571 High Similarity NPC267412
0.8571 High Similarity NPC319859
0.8571 High Similarity NPC98179
0.8571 High Similarity NPC166672
0.8571 High Similarity NPC142863
0.8571 High Similarity NPC18804
0.8571 High Similarity NPC198381
0.8571 High Similarity NPC253574
0.8571 High Similarity NPC74655
0.8571 High Similarity NPC47163
0.8571 High Similarity NPC260265
0.8571 High Similarity NPC164269
0.8571 High Similarity NPC127888
0.8571 High Similarity NPC100986
0.8571 High Similarity NPC287182
0.8561 High Similarity NPC14248
0.8561 High Similarity NPC469956
0.8552 High Similarity NPC471824
0.8552 High Similarity NPC36732
0.8551 High Similarity NPC80170
0.854 High Similarity NPC139595
0.854 High Similarity NPC472519
0.854 High Similarity NPC60704
0.854 High Similarity NPC293642
0.854 High Similarity NPC199204
0.8529 High Similarity NPC234109
0.8529 High Similarity NPC471826
0.8529 High Similarity NPC188327
0.8529 High Similarity NPC163248
0.8511 High Similarity NPC33986
0.8511 High Similarity NPC61499
0.8507 High Similarity NPC96286
0.8507 High Similarity NPC248429
0.8503 High Similarity NPC286038
0.8503 High Similarity NPC87950
0.8503 High Similarity NPC15577
0.8503 High Similarity NPC471764
0.8503 High Similarity NPC476347
0.85 High Similarity NPC222036
0.85 High Similarity NPC7526
0.85 High Similarity NPC469449
0.85 High Similarity NPC472524
0.85 High Similarity NPC83535
0.8496 Intermediate Similarity NPC163200
0.8496 Intermediate Similarity NPC235190
0.8496 Intermediate Similarity NPC180006
0.8493 Intermediate Similarity NPC85624
0.8489 Intermediate Similarity NPC250727
0.8483 Intermediate Similarity NPC229916
0.8456 Intermediate Similarity NPC168259
0.8456 Intermediate Similarity NPC93219
0.8456 Intermediate Similarity NPC244495
0.8446 Intermediate Similarity NPC476348
0.8446 Intermediate Similarity NPC66991
0.8446 Intermediate Similarity NPC187398
0.844 Intermediate Similarity NPC473107
0.844 Intermediate Similarity NPC307412
0.844 Intermediate Similarity NPC55149
0.8435 Intermediate Similarity NPC475872
0.8417 Intermediate Similarity NPC249425
0.8406 Intermediate Similarity NPC157212
0.8403 Intermediate Similarity NPC71903
0.8392 Intermediate Similarity NPC471069
0.8392 Intermediate Similarity NPC474886
0.8392 Intermediate Similarity NPC471068
0.8382 Intermediate Similarity NPC111347
0.8382 Intermediate Similarity NPC291899
0.838 Intermediate Similarity NPC469675
0.8378 Intermediate Similarity NPC296377
0.8377 Intermediate Similarity NPC4950
0.8367 Intermediate Similarity NPC86069
0.8367 Intermediate Similarity NPC295696
0.8367 Intermediate Similarity NPC226722
0.8357 Intermediate Similarity NPC293203
0.8357 Intermediate Similarity NPC118683
0.8357 Intermediate Similarity NPC211413
0.8357 Intermediate Similarity NPC244888
0.8357 Intermediate Similarity NPC68205
0.8357 Intermediate Similarity NPC164804
0.8356 Intermediate Similarity NPC138212
0.8346 Intermediate Similarity NPC281356
0.8346 Intermediate Similarity NPC298796

  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 NPC138149 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
0.8768 High Similarity NPD5124 Phase 1
0.8768 High Similarity NPD5123 Clinical (unspecified phase)
0.8417 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8406 Intermediate Similarity NPD4908 Phase 1
0.8298 Intermediate Similarity NPD4140 Approved
0.8296 Intermediate Similarity NPD422 Phase 1
0.8163 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.8163 Intermediate Similarity NPD3750 Approved
0.8095 Intermediate Similarity NPD1652 Phase 2
0.8069 Intermediate Similarity NPD3748 Approved
0.8029 Intermediate Similarity NPD1610 Phase 2
0.8028 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.8028 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD6273 Approved
0.8 Intermediate Similarity NPD7819 Suspended
0.7963 Intermediate Similarity NPD5844 Phase 1
0.7947 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD2797 Approved
0.7898 Intermediate Similarity NPD7768 Phase 2
0.7872 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD7411 Suspended
0.7868 Intermediate Similarity NPD1548 Phase 1
0.7812 Intermediate Similarity NPD8127 Discontinued
0.78 Intermediate Similarity NPD4628 Phase 3
0.7793 Intermediate Similarity NPD4060 Phase 1
0.7792 Intermediate Similarity NPD1653 Approved
0.7778 Intermediate Similarity NPD3268 Approved
0.7771 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD2796 Approved
0.7742 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD3225 Approved
0.7722 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD5763 Approved
0.7718 Intermediate Similarity NPD5762 Approved
0.7708 Intermediate Similarity NPD4625 Phase 3
0.7707 Intermediate Similarity NPD6801 Discontinued
0.7692 Intermediate Similarity NPD6599 Discontinued
0.7687 Intermediate Similarity NPD5535 Approved
0.7681 Intermediate Similarity NPD5691 Approved
0.7673 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD1613 Approved
0.7667 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD4749 Approved
0.7651 Intermediate Similarity NPD6100 Approved
0.7651 Intermediate Similarity NPD6099 Approved
0.7639 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7626 Intermediate Similarity NPD4626 Approved
0.7625 Intermediate Similarity NPD7075 Discontinued
0.7619 Intermediate Similarity NPD5735 Approved
0.7613 Intermediate Similarity NPD5403 Approved
0.7606 Intermediate Similarity NPD8651 Approved
0.7597 Intermediate Similarity NPD5401 Approved
0.7597 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD37 Approved
0.7593 Intermediate Similarity NPD7199 Phase 2
0.7586 Intermediate Similarity NPD7095 Approved
0.7584 Intermediate Similarity NPD7033 Discontinued
0.758 Intermediate Similarity NPD4380 Phase 2
0.7571 Intermediate Similarity NPD3496 Discontinued
0.7569 Intermediate Similarity NPD2861 Phase 2
0.7566 Intermediate Similarity NPD7003 Approved
0.7562 Intermediate Similarity NPD4965 Approved
0.7562 Intermediate Similarity NPD4966 Approved
0.7562 Intermediate Similarity NPD4967 Phase 2
0.7561 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD7549 Discontinued
0.7552 Intermediate Similarity NPD3266 Approved
0.7552 Intermediate Similarity NPD3267 Approved
0.755 Intermediate Similarity NPD1549 Phase 2
0.7548 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD7229 Phase 3
0.7535 Intermediate Similarity NPD5327 Phase 3
0.7534 Intermediate Similarity NPD1296 Phase 2
0.7534 Intermediate Similarity NPD6798 Discontinued
0.7532 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD6799 Approved
0.7517 Intermediate Similarity NPD7097 Phase 1
0.7516 Intermediate Similarity NPD3749 Approved
0.7516 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5402 Approved
0.75 Intermediate Similarity NPD6355 Discontinued
0.75 Intermediate Similarity NPD1778 Approved
0.7483 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD8032 Phase 2
0.7483 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD6666 Approved
0.7468 Intermediate Similarity NPD6667 Approved
0.7467 Intermediate Similarity NPD2799 Discontinued
0.7467 Intermediate Similarity NPD1510 Phase 2
0.7466 Intermediate Similarity NPD3027 Phase 3
0.7438 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD7213 Phase 3
0.7419 Intermediate Similarity NPD7212 Phase 2
0.7417 Intermediate Similarity NPD1551 Phase 2
0.7397 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7157 Approved
0.7391 Intermediate Similarity NPD3817 Phase 2
0.7391 Intermediate Similarity NPD4288 Approved
0.7386 Intermediate Similarity NPD6674 Discontinued
0.7378 Intermediate Similarity NPD6959 Discontinued
0.7372 Intermediate Similarity NPD7447 Phase 1
0.7368 Intermediate Similarity NPD3134 Approved
0.7368 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6002 Phase 3
0.7368 Intermediate Similarity NPD6005 Phase 3
0.7368 Intermediate Similarity NPD6004 Phase 3
0.7362 Intermediate Similarity NPD6234 Discontinued
0.7351 Intermediate Similarity NPD4308 Phase 3
0.7343 Intermediate Similarity NPD1608 Approved
0.7338 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD3892 Phase 2
0.7333 Intermediate Similarity NPD6353 Approved
0.7329 Intermediate Similarity NPD8455 Phase 2
0.7329 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD5494 Approved
0.7305 Intermediate Similarity NPD5585 Approved
0.7303 Intermediate Similarity NPD2935 Discontinued
0.7296 Intermediate Similarity NPD7458 Discontinued
0.7296 Intermediate Similarity NPD3226 Approved
0.7293 Intermediate Similarity NPD9697 Approved
0.7279 Intermediate Similarity NPD6832 Phase 2
0.7278 Intermediate Similarity NPD920 Approved
0.7273 Intermediate Similarity NPD1243 Approved
0.7273 Intermediate Similarity NPD1611 Approved
0.7267 Intermediate Similarity NPD4340 Discontinued
0.7267 Intermediate Similarity NPD1934 Approved
0.7262 Intermediate Similarity NPD7228 Approved
0.7261 Intermediate Similarity NPD2534 Approved
0.7261 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD2532 Approved
0.7261 Intermediate Similarity NPD2533 Approved
0.7248 Intermediate Similarity NPD6233 Phase 2
0.7246 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6166 Phase 2
0.7244 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD6232 Discontinued
0.7226 Intermediate Similarity NPD7466 Approved
0.7226 Intermediate Similarity NPD4110 Phase 3
0.7226 Intermediate Similarity NPD8166 Discontinued
0.7226 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD1465 Phase 2
0.7219 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD4097 Suspended
0.7211 Intermediate Similarity NPD5736 Approved
0.7208 Intermediate Similarity NPD2424 Discontinued
0.7202 Intermediate Similarity NPD7473 Discontinued
0.72 Intermediate Similarity NPD1240 Approved
0.72 Intermediate Similarity NPD4307 Phase 2
0.7195 Intermediate Similarity NPD6971 Discontinued
0.7193 Intermediate Similarity NPD6559 Discontinued
0.719 Intermediate Similarity NPD4476 Approved
0.719 Intermediate Similarity NPD4477 Approved
0.7185 Intermediate Similarity NPD1358 Approved
0.7181 Intermediate Similarity NPD2313 Discontinued
0.7172 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD3818 Discontinued
0.7153 Intermediate Similarity NPD1091 Approved
0.7152 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4624 Approved
0.7143 Intermediate Similarity NPD7266 Discontinued
0.7143 Intermediate Similarity NPD2346 Discontinued
0.7133 Intermediate Similarity NPD17 Approved
0.7132 Intermediate Similarity NPD2684 Approved
0.7123 Intermediate Similarity NPD1283 Approved
0.7118 Intermediate Similarity NPD7054 Approved
0.7117 Intermediate Similarity NPD2801 Approved
0.7113 Intermediate Similarity NPD7741 Discontinued
0.7107 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD1607 Approved
0.7103 Intermediate Similarity NPD9717 Approved
0.7093 Intermediate Similarity NPD7240 Approved
0.7089 Intermediate Similarity NPD7837 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1511 Approved
0.7086 Intermediate Similarity NPD2238 Phase 2
0.7086 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD3620 Phase 2
0.7076 Intermediate Similarity NPD7472 Approved
0.7076 Intermediate Similarity NPD7074 Phase 3
0.7075 Intermediate Similarity NPD1203 Approved
0.7067 Intermediate Similarity NPD3764 Approved
0.7067 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD7427 Discontinued
0.7059 Intermediate Similarity NPD4538 Approved
0.7059 Intermediate Similarity NPD290 Approved
0.7059 Intermediate Similarity NPD4536 Approved
0.7059 Intermediate Similarity NPD3751 Discontinued
0.7059 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD4359 Approved
0.7052 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD2800 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