Structure

Physi-Chem Properties

Molecular Weight:  490.24
Volume:  507.747
LogP:  4.375
LogD:  3.518
LogS:  -4.827
# Rotatable Bonds:  1
TPSA:  86.74
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.5
Synthetic Accessibility Score:  5.57
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.874
MDCK Permeability:  1.549645276099909e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.02
Human Intestinal Absorption (HIA):  0.07
20% Bioavailability (F20%):  0.978
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.105
Plasma Protein Binding (PPB):  93.67908477783203%
Volume Distribution (VD):  1.513
Pgp-substrate:  4.335516929626465%

ADMET: Metabolism

CYP1A2-inhibitor:  0.231
CYP1A2-substrate:  0.435
CYP2C19-inhibitor:  0.921
CYP2C19-substrate:  0.888
CYP2C9-inhibitor:  0.962
CYP2C9-substrate:  0.023
CYP2D6-inhibitor:  0.459
CYP2D6-substrate:  0.029
CYP3A4-inhibitor:  0.976
CYP3A4-substrate:  0.895

ADMET: Excretion

Clearance (CL):  11.809
Half-life (T1/2):  0.159

ADMET: Toxicity

hERG Blockers:  0.594
Human Hepatotoxicity (H-HT):  0.317
Drug-inuced Liver Injury (DILI):  0.388
AMES Toxicity:  0.018
Rat Oral Acute Toxicity:  0.576
Maximum Recommended Daily Dose:  0.923
Skin Sensitization:  0.925
Carcinogencity:  0.871
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.608

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

  Natural Product: NPC127197

Natural Product ID:  NPC127197
Common Name*:   (+)-7,7-Bis[(5R,7R,9R,10S)-2-Oxocadinan-3,6(11)-Dien-12,7-Olide]
IUPAC Name:   (3aR,5R,5aS,9aR)-3a-[(3aR,5R,5aS,9aR)-1,5,8-trimethyl-2,7-dioxo-5,5a,6,9a-tetrahydro-4H-benzo[e][1]benzofuran-3a-yl]-1,5,8-trimethyl-5,5a,6,9a-tetrahydro-4H-benzo[e][1]benzofuran-2,7-dione
Synonyms:  
Standard InCHIKey:  KFBJGXFXBDVQQJ-NIKNNLPWSA-N
Standard InCHI:  InChI=1S/C30H34O6/c1-13-7-21-19(9-23(13)31)15(3)11-29(25(21)17(5)27(33)35-29)30-12-16(4)20-10-24(32)14(2)8-22(20)26(30)18(6)28(34)36-30/h7-8,15-16,19-22H,9-12H2,1-6H3/t15-,16-,19+,20+,21+,22+,29-,30-/m1/s1
SMILES:  C[C@@H]1C[C@]2(OC(=O)C(=C2[C@@H]2[C@H]1CC(=O)C(=C2)C)C)[C@]12C[C@@H](C)[C@H]3[C@@H](C2=C(C(=O)O1)C)C=C(C(=O)C3)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL515955
PubChem CID:   25016667
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO26870 Nephthea pacifica Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[15679321]
NPO26870 Nephthea pacifica Species Nephtheidae Eukaryota n.a. Formosan soft coral n.a. PMID[15679321]
NPO11769 Eupatorium adenophorum Species Asteraceae Eukaryota Leaves n.a. n.a. PMID[18620454]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. seed n.a. PMID[21049973]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[23701597]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[25819096]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26764 Morinda tinctoria Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26814 Consolida pubescens Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11769 Eupatorium adenophorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26764 Morinda tinctoria Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9281 Melampodium diffusum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26764 Morinda tinctoria Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13720 Deparia lancea Species Athyriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8654 Digitalis viridiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11769 Eupatorium adenophorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26814 Consolida pubescens Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26870 Nephthea pacifica Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26592 Isaria cretacea Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26490 Helenium aromaticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13073 Thymus bashkiriensis 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
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 5000.0 nM PMID[503958]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 5000.0 nM PMID[503958]
NPT179 Cell Line A2780 Homo sapiens IC50 > 5000.0 nM PMID[503958]

☑ 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 NPC127197 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
0.8242 Intermediate Similarity NPC30486
0.8163 Intermediate Similarity NPC38530
0.8163 Intermediate Similarity NPC84335
0.8152 Intermediate Similarity NPC189311
0.8039 Intermediate Similarity NPC189616
0.8 Intermediate Similarity NPC285982
0.798 Intermediate Similarity NPC476253
0.7979 Intermediate Similarity NPC477228
0.7938 Intermediate Similarity NPC1108
0.79 Intermediate Similarity NPC478056
0.7895 Intermediate Similarity NPC472302
0.7895 Intermediate Similarity NPC226863
0.7835 Intermediate Similarity NPC289479
0.7826 Intermediate Similarity NPC200513
0.7812 Intermediate Similarity NPC5509
0.7812 Intermediate Similarity NPC173042
0.78 Intermediate Similarity NPC170131
0.7789 Intermediate Similarity NPC30421
0.7778 Intermediate Similarity NPC171395
0.7767 Intermediate Similarity NPC180204
0.7767 Intermediate Similarity NPC254202
0.7767 Intermediate Similarity NPC112009
0.7755 Intermediate Similarity NPC475657
0.7755 Intermediate Similarity NPC472303
0.7745 Intermediate Similarity NPC310981
0.7742 Intermediate Similarity NPC193198
0.7732 Intermediate Similarity NPC76286
0.7732 Intermediate Similarity NPC159748
0.7732 Intermediate Similarity NPC101651
0.7732 Intermediate Similarity NPC476369
0.7732 Intermediate Similarity NPC476437
0.7732 Intermediate Similarity NPC8062
0.7723 Intermediate Similarity NPC252295
0.7708 Intermediate Similarity NPC478259
0.7708 Intermediate Similarity NPC478260
0.7708 Intermediate Similarity NPC478261
0.7708 Intermediate Similarity NPC48107
0.7692 Intermediate Similarity NPC472868
0.7685 Intermediate Similarity NPC470063
0.7684 Intermediate Similarity NPC220478
0.7677 Intermediate Similarity NPC476415
0.7677 Intermediate Similarity NPC38830
0.7677 Intermediate Similarity NPC470697
0.7677 Intermediate Similarity NPC84893
0.7664 Intermediate Similarity NPC37116
0.7664 Intermediate Similarity NPC253906
0.7664 Intermediate Similarity NPC473627
0.7664 Intermediate Similarity NPC29133
0.7653 Intermediate Similarity NPC49420
0.7647 Intermediate Similarity NPC476299
0.7647 Intermediate Similarity NPC474012
0.7647 Intermediate Similarity NPC201406
0.7647 Intermediate Similarity NPC471413
0.7634 Intermediate Similarity NPC471218
0.7634 Intermediate Similarity NPC186276
0.7632 Intermediate Similarity NPC120724
0.7632 Intermediate Similarity NPC473979
0.7629 Intermediate Similarity NPC174342
0.7629 Intermediate Similarity NPC284561
0.7629 Intermediate Similarity NPC177141
0.7629 Intermediate Similarity NPC73995
0.7624 Intermediate Similarity NPC224356
0.7624 Intermediate Similarity NPC253826
0.7624 Intermediate Similarity NPC476768
0.7624 Intermediate Similarity NPC121402
0.7624 Intermediate Similarity NPC204054
0.7624 Intermediate Similarity NPC151681
0.7624 Intermediate Similarity NPC175351
0.7624 Intermediate Similarity NPC110937
0.7624 Intermediate Similarity NPC257726
0.7624 Intermediate Similarity NPC132753
0.7604 Intermediate Similarity NPC181327
0.76 Intermediate Similarity NPC33473
0.7593 Intermediate Similarity NPC324683
0.7593 Intermediate Similarity NPC470961
0.7589 Intermediate Similarity NPC475520
0.7579 Intermediate Similarity NPC2709
0.7579 Intermediate Similarity NPC65661
0.7579 Intermediate Similarity NPC474013
0.7576 Intermediate Similarity NPC139692
0.7576 Intermediate Similarity NPC79117
0.7576 Intermediate Similarity NPC472871
0.7573 Intermediate Similarity NPC303559
0.7573 Intermediate Similarity NPC471412
0.7573 Intermediate Similarity NPC168319
0.7573 Intermediate Similarity NPC194028
0.7568 Intermediate Similarity NPC470493
0.7568 Intermediate Similarity NPC183580
0.7568 Intermediate Similarity NPC286528
0.7568 Intermediate Similarity NPC284068
0.7568 Intermediate Similarity NPC20302
0.7568 Intermediate Similarity NPC167606
0.7568 Intermediate Similarity NPC312824
0.7568 Intermediate Similarity NPC470492
0.7568 Intermediate Similarity NPC140055
0.7553 Intermediate Similarity NPC22611
0.7551 Intermediate Similarity NPC273199
0.7551 Intermediate Similarity NPC469595
0.7551 Intermediate Similarity NPC220454
0.7551 Intermediate Similarity NPC51486
0.7551 Intermediate Similarity NPC152467
0.7551 Intermediate Similarity NPC212679
0.7549 Intermediate Similarity NPC176845
0.7547 Intermediate Similarity NPC67321
0.7547 Intermediate Similarity NPC187435
0.7547 Intermediate Similarity NPC475294
0.7547 Intermediate Similarity NPC133422
0.7545 Intermediate Similarity NPC147912
0.7545 Intermediate Similarity NPC474181
0.7545 Intermediate Similarity NPC67259
0.7527 Intermediate Similarity NPC278459
0.7526 Intermediate Similarity NPC215831
0.7525 Intermediate Similarity NPC154526
0.7525 Intermediate Similarity NPC472363
0.7525 Intermediate Similarity NPC307164
0.7525 Intermediate Similarity NPC29952
0.7525 Intermediate Similarity NPC472362
0.7523 Intermediate Similarity NPC236217
0.7523 Intermediate Similarity NPC191620
0.75 Intermediate Similarity NPC40918
0.75 Intermediate Similarity NPC476081
0.75 Intermediate Similarity NPC477129
0.75 Intermediate Similarity NPC709
0.75 Intermediate Similarity NPC186525
0.75 Intermediate Similarity NPC473720
0.75 Intermediate Similarity NPC477130
0.75 Intermediate Similarity NPC162973
0.75 Intermediate Similarity NPC476596
0.75 Intermediate Similarity NPC50774
0.7477 Intermediate Similarity NPC472825
0.7477 Intermediate Similarity NPC189075
0.7477 Intermediate Similarity NPC176840
0.7477 Intermediate Similarity NPC318363
0.7477 Intermediate Similarity NPC473482
0.7477 Intermediate Similarity NPC475418
0.7477 Intermediate Similarity NPC306265
0.7477 Intermediate Similarity NPC64318
0.7477 Intermediate Similarity NPC275539
0.7477 Intermediate Similarity NPC190286
0.7476 Intermediate Similarity NPC117685
0.7476 Intermediate Similarity NPC470906
0.7475 Intermediate Similarity NPC473944
0.7475 Intermediate Similarity NPC303697
0.7474 Intermediate Similarity NPC475100
0.7474 Intermediate Similarity NPC96055
0.7474 Intermediate Similarity NPC149869
0.7473 Intermediate Similarity NPC472300
0.7455 Intermediate Similarity NPC122056
0.7453 Intermediate Similarity NPC127790
0.7453 Intermediate Similarity NPC478052
0.7451 Intermediate Similarity NPC10057
0.7451 Intermediate Similarity NPC473456
0.7451 Intermediate Similarity NPC292133
0.7451 Intermediate Similarity NPC2049
0.7451 Intermediate Similarity NPC474343
0.7449 Intermediate Similarity NPC36668
0.7449 Intermediate Similarity NPC118011
0.7449 Intermediate Similarity NPC262043
0.7449 Intermediate Similarity NPC305039
0.7447 Intermediate Similarity NPC327969
0.7447 Intermediate Similarity NPC321289
0.7434 Intermediate Similarity NPC264954
0.7431 Intermediate Similarity NPC470960
0.7431 Intermediate Similarity NPC474315
0.7429 Intermediate Similarity NPC478057
0.7429 Intermediate Similarity NPC476889
0.7429 Intermediate Similarity NPC120321
0.7429 Intermediate Similarity NPC95899
0.7429 Intermediate Similarity NPC470954
0.7426 Intermediate Similarity NPC295347
0.7426 Intermediate Similarity NPC470978
0.7426 Intermediate Similarity NPC470974
0.7426 Intermediate Similarity NPC183012
0.7426 Intermediate Similarity NPC209355
0.7426 Intermediate Similarity NPC281134
0.7426 Intermediate Similarity NPC274417
0.7426 Intermediate Similarity NPC474909
0.7426 Intermediate Similarity NPC147232
0.7423 Intermediate Similarity NPC136948
0.7423 Intermediate Similarity NPC476409
0.7407 Intermediate Similarity NPC112457
0.7407 Intermediate Similarity NPC475065
0.7404 Intermediate Similarity NPC93744
0.7404 Intermediate Similarity NPC63249
0.7404 Intermediate Similarity NPC476888
0.74 Intermediate Similarity NPC476597
0.74 Intermediate Similarity NPC476598
0.74 Intermediate Similarity NPC229976
0.74 Intermediate Similarity NPC169343
0.74 Intermediate Similarity NPC476416
0.74 Intermediate Similarity NPC474185
0.7396 Intermediate Similarity NPC86316
0.7396 Intermediate Similarity NPC474537
0.7396 Intermediate Similarity NPC106416
0.7396 Intermediate Similarity NPC137493
0.7383 Intermediate Similarity NPC91034
0.7383 Intermediate Similarity NPC471601
0.7383 Intermediate Similarity NPC329048
0.7383 Intermediate Similarity NPC110496
0.7383 Intermediate Similarity NPC301666

  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 NPC127197 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
0.7826 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7789 Intermediate Similarity NPD3573 Approved
0.7653 Intermediate Similarity NPD5693 Phase 1
0.7568 Intermediate Similarity NPD7115 Discovery
0.7449 Intermediate Similarity NPD6904 Approved
0.7449 Intermediate Similarity NPD6080 Approved
0.7449 Intermediate Similarity NPD6673 Approved
0.7426 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD6672 Approved
0.7347 Intermediate Similarity NPD6903 Approved
0.7347 Intermediate Similarity NPD5737 Approved
0.7347 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD7748 Approved
0.7327 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD7900 Approved
0.732 Intermediate Similarity NPD6684 Approved
0.732 Intermediate Similarity NPD7521 Approved
0.732 Intermediate Similarity NPD6409 Approved
0.732 Intermediate Similarity NPD5330 Approved
0.732 Intermediate Similarity NPD7146 Approved
0.732 Intermediate Similarity NPD7334 Approved
0.73 Intermediate Similarity NPD6050 Approved
0.7216 Intermediate Similarity NPD1694 Approved
0.72 Intermediate Similarity NPD5692 Phase 3
0.72 Intermediate Similarity NPD5207 Approved
0.7172 Intermediate Similarity NPD5208 Approved
0.7157 Intermediate Similarity NPD6001 Approved
0.7143 Intermediate Similarity NPD6098 Approved
0.7129 Intermediate Similarity NPD7515 Phase 2
0.7129 Intermediate Similarity NPD5694 Approved
0.7115 Intermediate Similarity NPD7902 Approved
0.71 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6399 Phase 3
0.7048 Intermediate Similarity NPD4225 Approved
0.7048 Intermediate Similarity NPD7638 Approved
0.7 Intermediate Similarity NPD6686 Approved
0.6981 Remote Similarity NPD7640 Approved
0.6981 Remote Similarity NPD7639 Approved
0.6972 Remote Similarity NPD6008 Approved
0.6952 Remote Similarity NPD6084 Phase 2
0.6952 Remote Similarity NPD6083 Phase 2
0.6937 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5695 Phase 3
0.6903 Remote Similarity NPD8297 Approved
0.6875 Remote Similarity NPD4695 Discontinued
0.6875 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6857 Remote Similarity NPD7732 Phase 3
0.6847 Remote Similarity NPD7320 Approved
0.6847 Remote Similarity NPD6881 Approved
0.6847 Remote Similarity NPD6899 Approved
0.6818 Remote Similarity NPD6675 Approved
0.6818 Remote Similarity NPD5739 Approved
0.6818 Remote Similarity NPD6402 Approved
0.6818 Remote Similarity NPD7128 Approved
0.68 Remote Similarity NPD3574 Clinical (unspecified phase)
0.68 Remote Similarity NPD4519 Discontinued
0.68 Remote Similarity NPD4623 Approved
0.6796 Remote Similarity NPD5284 Approved
0.6796 Remote Similarity NPD5281 Approved
0.6789 Remote Similarity NPD6052 Approved
0.6777 Remote Similarity NPD7507 Approved
0.6765 Remote Similarity NPD6051 Approved
0.6762 Remote Similarity NPD5654 Approved
0.6757 Remote Similarity NPD5697 Approved
0.6735 Remote Similarity NPD4223 Phase 3
0.6735 Remote Similarity NPD4221 Approved
0.6729 Remote Similarity NPD5696 Approved
0.6726 Remote Similarity NPD7290 Approved
0.6726 Remote Similarity NPD7102 Approved
0.6726 Remote Similarity NPD6883 Approved
0.67 Remote Similarity NPD5329 Approved
0.6698 Remote Similarity NPD7614 Phase 1
0.6696 Remote Similarity NPD6011 Approved
0.6667 Remote Similarity NPD8130 Phase 1
0.6667 Remote Similarity NPD6649 Approved
0.6667 Remote Similarity NPD6650 Approved
0.6667 Remote Similarity NPD6847 Approved
0.6667 Remote Similarity NPD6617 Approved
0.6667 Remote Similarity NPD6869 Approved
0.6637 Remote Similarity NPD6013 Approved
0.6637 Remote Similarity NPD6012 Approved
0.6637 Remote Similarity NPD6373 Approved
0.6637 Remote Similarity NPD6372 Approved
0.6637 Remote Similarity NPD6014 Approved
0.6636 Remote Similarity NPD5959 Approved
0.6635 Remote Similarity NPD6079 Approved
0.6634 Remote Similarity NPD3618 Phase 1
0.6634 Remote Similarity NPD5690 Phase 2
0.663 Remote Similarity NPD4691 Approved
0.6613 Remote Similarity NPD7319 Approved
0.6609 Remote Similarity NPD6882 Approved
0.6609 Remote Similarity NPD6053 Discontinued
0.6607 Remote Similarity NPD5701 Approved
0.6607 Remote Similarity NPD6614 Approved
0.6602 Remote Similarity NPD5328 Approved
0.66 Remote Similarity NPD4786 Approved
0.66 Remote Similarity NPD4197 Approved
0.66 Remote Similarity NPD3668 Phase 3
0.6566 Remote Similarity NPD3667 Approved
0.6552 Remote Similarity NPD4632 Approved
0.6522 Remote Similarity NPD4137 Phase 3
0.6522 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6471 Remote Similarity NPD4138 Approved
0.6471 Remote Similarity NPD4688 Approved
0.6471 Remote Similarity NPD5280 Approved
0.6471 Remote Similarity NPD7328 Approved
0.6471 Remote Similarity NPD4690 Approved
0.6471 Remote Similarity NPD5205 Approved
0.6471 Remote Similarity NPD4694 Approved
0.6471 Remote Similarity NPD4693 Phase 3
0.6471 Remote Similarity NPD7327 Approved
0.6471 Remote Similarity NPD4689 Approved
0.646 Remote Similarity NPD6412 Phase 2
0.6452 Remote Similarity NPD4747 Approved
0.6446 Remote Similarity NPD8033 Approved
0.6442 Remote Similarity NPD4753 Phase 2
0.6442 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6442 Remote Similarity NPD6101 Approved
0.6436 Remote Similarity NPD3665 Phase 1
0.6436 Remote Similarity NPD3666 Approved
0.6436 Remote Similarity NPD3133 Approved
0.6423 Remote Similarity NPD7492 Approved
0.6421 Remote Similarity NPD5733 Approved
0.6421 Remote Similarity NPD4058 Approved
0.6417 Remote Similarity NPD7516 Approved
0.6415 Remote Similarity NPD5779 Approved
0.6415 Remote Similarity NPD5778 Approved
0.6415 Remote Similarity NPD4202 Approved
0.64 Remote Similarity NPD7736 Approved
0.6396 Remote Similarity NPD7632 Discontinued
0.6396 Remote Similarity NPD5211 Phase 2
0.6389 Remote Similarity NPD5222 Approved
0.6389 Remote Similarity NPD5221 Approved
0.6389 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6387 Remote Similarity NPD6009 Approved
0.6381 Remote Similarity NPD46 Approved
0.6381 Remote Similarity NPD6698 Approved
0.6371 Remote Similarity NPD6616 Approved
0.6364 Remote Similarity NPD5285 Approved
0.6364 Remote Similarity NPD8294 Approved
0.6364 Remote Similarity NPD5286 Approved
0.6364 Remote Similarity NPD8377 Approved
0.6364 Remote Similarity NPD6404 Discontinued
0.6364 Remote Similarity NPD4696 Approved
0.6364 Remote Similarity NPD6319 Approved
0.6364 Remote Similarity NPD6648 Approved
0.6364 Remote Similarity NPD6054 Approved
0.6354 Remote Similarity NPD8039 Approved
0.6341 Remote Similarity NPD7604 Phase 2
0.6333 Remote Similarity NPD6335 Approved
0.633 Remote Similarity NPD5173 Approved
0.633 Remote Similarity NPD4755 Approved
0.6327 Remote Similarity NPD3617 Approved
0.6321 Remote Similarity NPD6411 Approved
0.6321 Remote Similarity NPD8035 Phase 2
0.6321 Remote Similarity NPD8034 Phase 2
0.632 Remote Similarity NPD7078 Approved
0.6316 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6311 Remote Similarity NPD8296 Approved
0.6311 Remote Similarity NPD8380 Approved
0.6311 Remote Similarity NPD8379 Approved
0.6311 Remote Similarity NPD5983 Phase 2
0.6311 Remote Similarity NPD8378 Approved
0.6311 Remote Similarity NPD8335 Approved
0.6306 Remote Similarity NPD5344 Discontinued
0.6306 Remote Similarity NPD5223 Approved
0.6303 Remote Similarity NPD6868 Approved
0.6303 Remote Similarity NPD6274 Approved
0.6296 Remote Similarity NPD5210 Approved
0.6296 Remote Similarity NPD4629 Approved
0.6283 Remote Similarity NPD5141 Approved
0.6281 Remote Similarity NPD7101 Approved
0.6281 Remote Similarity NPD7100 Approved
0.6263 Remote Similarity NPD4195 Approved
0.626 Remote Similarity NPD6370 Approved
0.625 Remote Similarity NPD5225 Approved
0.625 Remote Similarity NPD6317 Approved
0.625 Remote Similarity NPD4633 Approved
0.625 Remote Similarity NPD5224 Approved
0.625 Remote Similarity NPD4687 Approved
0.625 Remote Similarity NPD5226 Approved
0.624 Remote Similarity NPD6336 Discontinued
0.6239 Remote Similarity NPD4697 Phase 3
0.623 Remote Similarity NPD6059 Approved
0.6226 Remote Similarity NPD5785 Approved
0.6216 Remote Similarity NPD4700 Approved
0.6214 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6214 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6211 Remote Similarity NPD5276 Approved
0.621 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6207 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6198 Remote Similarity NPD6314 Approved
0.6198 Remote Similarity NPD6313 Approved
0.6195 Remote Similarity NPD5174 Approved
0.6195 Remote Similarity NPD5175 Approved
0.619 Remote Similarity NPD8293 Discontinued
0.6179 Remote Similarity NPD6016 Approved
0.6179 Remote Similarity NPD6015 Approved
0.6179 Remote Similarity NPD6291 Clinical (unspecified phase)

  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