Structure

Physi-Chem Properties

Molecular Weight:  638.16
Volume:  602.115
LogP:  2.43
LogD:  0.963
LogS:  -3.759
# Rotatable Bonds:  5
TPSA:  220.26
# H-Bond Aceptor:  14
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.271
Synthetic Accessibility Score:  5.406
Fsp3:  0.438
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.034
MDCK Permeability:  2.1512325474759564e-05
Pgp-inhibitor:  0.473
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.173
20% Bioavailability (F20%):  0.058
30% Bioavailability (F30%):  0.687

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.017
Plasma Protein Binding (PPB):  90.02738189697266%
Volume Distribution (VD):  0.612
Pgp-substrate:  3.3108041286468506%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.891
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.172
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.089
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.136
CYP3A4-inhibitor:  0.734
CYP3A4-substrate:  0.447

ADMET: Excretion

Clearance (CL):  10.215
Half-life (T1/2):  0.016

ADMET: Toxicity

hERG Blockers:  0.029
Human Hepatotoxicity (H-HT):  0.859
Drug-inuced Liver Injury (DILI):  0.971
AMES Toxicity:  0.016
Rat Oral Acute Toxicity:  0.98
Maximum Recommended Daily Dose:  0.02
Skin Sensitization:  0.252
Carcinogencity:  0.114
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.063

Download Data

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

  Natural Product: NPC86809

Natural Product ID:  NPC86809
Common Name*:   Secalonic Acid A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  DRYDKQOPVBDZMQ-ZKHWAINJSA-N
Standard InCHI:  InChI=1S/C32H30O14/c1-11-9-15(33)21-25(37)19-17(45-31(21,27(11)39)29(41)43-3)7-5-13(23(19)35)14-6-8-18-20(24(14)36)26(38)22-16(34)10-12(2)28(40)32(22,46-18)30(42)44-4/h5-8,11-12,27-28,33-36,39-40H,9-10H2,1-4H3/t11-,12-,27+,28+,31+,32+/m1/s1
SMILES:  COC(=O)[C@@]12Oc3ccc(c(c3C(=O)C2=C(C[C@H]([C@@H]1O)C)O)O)c1ccc2c(c1O)C(=O)C1=C(O)C[C@H]([C@@H]([C@]1(O2)C(=O)OC)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL500027
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0002817] Dibenzopyrans
            • [CHEMONTID:0000200] Xanthenes
              • [CHEMONTID:0000204] Xanthones

*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
NPO20214 Ruprechtia tangarana Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[12932125]
NPO40075 Clohesyomyces sp. Species Lindgomycetaceae Eukaryota n.a. n.a. n.a. PMID[27964996]
NPO20214 Ruprechtia tangarana Species Polygonaceae 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
NPT168 Cell Line P388 Mus musculus ED50 = 3.5 ug ml-1 PMID[509483]
NPT1323 Individual Protein Botulinum neurotoxin type A Clostridium botulinum (strain Hall / ATCC 3502 / NCTC 13319 / Type A) Inhibition = 64.5 % PMID[509484]
NPT1323 Individual Protein Botulinum neurotoxin type A Clostridium botulinum (strain Hall / ATCC 3502 / NCTC 13319 / Type A) Inhibition = 39.1 % PMID[509484]
NPT1323 Individual Protein Botulinum neurotoxin type A Clostridium botulinum (strain Hall / ATCC 3502 / NCTC 13319 / Type A) IC50 = 28600.0 nM PMID[509484]
NPT1323 Individual Protein Botulinum neurotoxin type A Clostridium botulinum (strain Hall / ATCC 3502 / NCTC 13319 / Type A) TIME = 1.117 hr PMID[509484]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 4.0 ug.mL-1 PMID[509483]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 32.0 ug.mL-1 PMID[509483]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC > 75.0 ug.mL-1 PMID[509485]
NPT2 Others Unspecified IC50 = 1400000.0 nM PMID[509485]

☑ 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 NPC86809 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
1.0 High Similarity NPC98667
1.0 High Similarity NPC232412
0.9939 High Similarity NPC469345
0.9693 High Similarity NPC251144
0.9693 High Similarity NPC241387
0.9639 High Similarity NPC477682
0.9639 High Similarity NPC477683
0.9512 High Similarity NPC297195
0.9512 High Similarity NPC207574
0.9512 High Similarity NPC291795
0.9357 High Similarity NPC197972
0.9341 High Similarity NPC154986
0.9253 High Similarity NPC48474
0.9157 High Similarity NPC178173
0.8994 High Similarity NPC241874
0.8947 High Similarity NPC294149
0.8941 High Similarity NPC472620
0.8935 High Similarity NPC217378
0.8895 High Similarity NPC324220
0.8895 High Similarity NPC312630
0.8862 High Similarity NPC473961
0.8851 High Similarity NPC208069
0.8824 High Similarity NPC472619
0.8788 High Similarity NPC146636
0.8779 High Similarity NPC476139
0.8779 High Similarity NPC469393
0.8772 High Similarity NPC193698
0.8764 High Similarity NPC314672
0.875 High Similarity NPC106700
0.875 High Similarity NPC472059
0.8736 High Similarity NPC476199
0.8736 High Similarity NPC476210
0.8713 High Similarity NPC54903
0.8713 High Similarity NPC473096
0.8713 High Similarity NPC177480
0.8713 High Similarity NPC286074
0.8713 High Similarity NPC326877
0.8713 High Similarity NPC473095
0.8698 High Similarity NPC472053
0.8698 High Similarity NPC63438
0.8683 High Similarity NPC125969
0.8683 High Similarity NPC186113
0.8675 High Similarity NPC20530
0.8675 High Similarity NPC10754
0.8675 High Similarity NPC215917
0.8675 High Similarity NPC164427
0.8674 High Similarity NPC282474
0.8674 High Similarity NPC470198
0.8674 High Similarity NPC316274
0.8674 High Similarity NPC470193
0.8674 High Similarity NPC470196
0.8674 High Similarity NPC470200
0.8674 High Similarity NPC470194
0.8674 High Similarity NPC470197
0.8674 High Similarity NPC470195
0.8671 High Similarity NPC476152
0.8671 High Similarity NPC476229
0.8671 High Similarity NPC476311
0.8663 High Similarity NPC74559
0.8659 High Similarity NPC207346
0.8659 High Similarity NPC46564
0.8655 High Similarity NPC225419
0.8655 High Similarity NPC473094
0.8655 High Similarity NPC472622
0.8655 High Similarity NPC292233
0.8652 High Similarity NPC282636
0.8652 High Similarity NPC294863
0.8647 High Similarity NPC472057
0.8647 High Similarity NPC472051
0.8639 High Similarity NPC473022
0.8636 High Similarity NPC475161
0.8636 High Similarity NPC477860
0.8631 High Similarity NPC471976
0.8621 High Similarity NPC162248
0.8614 High Similarity NPC111341
0.8614 High Similarity NPC48579
0.8614 High Similarity NPC304207
0.8614 High Similarity NPC476169
0.8614 High Similarity NPC207809
0.8614 High Similarity NPC259710
0.8614 High Similarity NPC217706
0.8614 High Similarity NPC237560
0.8614 High Similarity NPC304745
0.8613 High Similarity NPC473113
0.8613 High Similarity NPC477529
0.8613 High Similarity NPC476159
0.8606 High Similarity NPC210597
0.8606 High Similarity NPC217149
0.8606 High Similarity NPC216035
0.8606 High Similarity NPC475790
0.8605 High Similarity NPC102810
0.8605 High Similarity NPC5319
0.8605 High Similarity NPC476216
0.8596 High Similarity NPC120857
0.8596 High Similarity NPC17274
0.8596 High Similarity NPC85047
0.8596 High Similarity NPC469394
0.8596 High Similarity NPC472621
0.8589 High Similarity NPC191634
0.8588 High Similarity NPC475148
0.8588 High Similarity NPC475656
0.858 High Similarity NPC476929
0.858 High Similarity NPC473607
0.858 High Similarity NPC3629
0.858 High Similarity NPC84494
0.858 High Similarity NPC245059
0.858 High Similarity NPC97812
0.858 High Similarity NPC244903
0.8571 High Similarity NPC475246
0.8564 High Similarity NPC470199
0.8564 High Similarity NPC314459
0.8563 High Similarity NPC470336
0.8563 High Similarity NPC470335
0.8555 High Similarity NPC313304
0.8555 High Similarity NPC103307
0.8554 High Similarity NPC311579
0.8554 High Similarity NPC268193
0.8554 High Similarity NPC326592
0.8554 High Similarity NPC248793
0.8554 High Similarity NPC109594
0.8554 High Similarity NPC112701
0.8554 High Similarity NPC180301
0.8554 High Similarity NPC203080
0.8554 High Similarity NPC236756
0.8554 High Similarity NPC209760
0.8554 High Similarity NPC100134
0.8547 High Similarity NPC470341
0.8547 High Similarity NPC324522
0.8547 High Similarity NPC472058
0.8547 High Similarity NPC105414
0.8547 High Similarity NPC8965
0.8547 High Similarity NPC234497
0.8545 High Similarity NPC295650
0.8545 High Similarity NPC254412
0.8545 High Similarity NPC474023
0.8545 High Similarity NPC262039
0.8545 High Similarity NPC278476
0.8545 High Similarity NPC319910
0.8545 High Similarity NPC474021
0.8545 High Similarity NPC262038
0.8539 High Similarity NPC75574
0.8538 High Similarity NPC62261
0.8533 High Similarity NPC131405
0.8531 High Similarity NPC470452
0.8531 High Similarity NPC164047
0.8531 High Similarity NPC470453
0.8531 High Similarity NPC470448
0.8529 High Similarity NPC259834
0.8529 High Similarity NPC472402
0.8523 High Similarity NPC233978
0.8523 High Similarity NPC470334
0.8521 High Similarity NPC472055
0.8514 High Similarity NPC68381
0.8514 High Similarity NPC63105
0.8514 High Similarity NPC199533
0.8514 High Similarity NPC3718
0.8514 High Similarity NPC470454
0.8512 High Similarity NPC246466
0.8506 High Similarity NPC271848
0.8506 High Similarity NPC212038
0.8506 High Similarity NPC262580
0.8506 High Similarity NPC289396
0.8506 High Similarity NPC118128
0.8506 High Similarity NPC257667
0.8506 High Similarity NPC472454
0.8506 High Similarity NPC315619
0.8506 High Similarity NPC121333
0.8506 High Similarity NPC186847
0.8506 High Similarity NPC91650
0.8506 High Similarity NPC81332
0.8503 High Similarity NPC326910
0.8503 High Similarity NPC477958
0.8503 High Similarity NPC471116
0.8497 Intermediate Similarity NPC20734
0.8497 Intermediate Similarity NPC246274
0.8497 Intermediate Similarity NPC41598
0.8497 Intermediate Similarity NPC476146
0.8497 Intermediate Similarity NPC75141
0.8497 Intermediate Similarity NPC55422
0.8497 Intermediate Similarity NPC40089
0.8497 Intermediate Similarity NPC158329
0.8497 Intermediate Similarity NPC47634
0.8497 Intermediate Similarity NPC242395
0.8494 Intermediate Similarity NPC56232
0.8494 Intermediate Similarity NPC244583
0.8494 Intermediate Similarity NPC321363
0.8494 Intermediate Similarity NPC253904
0.8494 Intermediate Similarity NPC150123
0.8494 Intermediate Similarity NPC275878
0.8494 Intermediate Similarity NPC10807
0.8494 Intermediate Similarity NPC138288
0.8494 Intermediate Similarity NPC171651
0.8494 Intermediate Similarity NPC243171
0.8494 Intermediate Similarity NPC35567
0.8494 Intermediate Similarity NPC161881
0.8492 Intermediate Similarity NPC87583
0.8488 Intermediate Similarity NPC476255
0.8488 Intermediate Similarity NPC120593
0.8488 Intermediate Similarity NPC471213
0.8488 Intermediate Similarity NPC207575

  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 NPC86809 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
0.8623 High Similarity NPD7075 Discontinued
0.8605 High Similarity NPD7804 Clinical (unspecified phase)
0.8494 Intermediate Similarity NPD6801 Discontinued
0.8444 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8443 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8393 Intermediate Similarity NPD5402 Approved
0.8363 Intermediate Similarity NPD6959 Discontinued
0.8324 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8324 Intermediate Similarity NPD6166 Phase 2
0.8324 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD4380 Phase 2
0.8225 Intermediate Similarity NPD7819 Suspended
0.8202 Intermediate Similarity NPD7808 Phase 3
0.8202 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD5403 Approved
0.8192 Intermediate Similarity NPD6797 Phase 2
0.8176 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD7473 Discontinued
0.8156 Intermediate Similarity NPD8313 Approved
0.8156 Intermediate Similarity NPD8312 Approved
0.8146 Intermediate Similarity NPD7251 Discontinued
0.8146 Intermediate Similarity NPD6559 Discontinued
0.8122 Intermediate Similarity NPD8150 Discontinued
0.8118 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8114 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8103 Intermediate Similarity NPD6232 Discontinued
0.809 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8081 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD5844 Phase 1
0.8072 Intermediate Similarity NPD5401 Approved
0.8072 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.807 Intermediate Similarity NPD3817 Phase 2
0.8047 Intermediate Similarity NPD6599 Discontinued
0.8034 Intermediate Similarity NPD7074 Phase 3
0.8023 Intermediate Similarity NPD7768 Phase 2
0.8023 Intermediate Similarity NPD3751 Discontinued
0.8022 Intermediate Similarity NPD8434 Phase 2
0.8012 Intermediate Similarity NPD6799 Approved
0.8 Intermediate Similarity NPD7411 Suspended
0.7989 Intermediate Similarity NPD5494 Approved
0.7978 Intermediate Similarity NPD7054 Approved
0.7953 Intermediate Similarity NPD1934 Approved
0.7935 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD7472 Approved
0.7919 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7906 Intermediate Similarity NPD7435 Discontinued
0.7831 Intermediate Similarity NPD3750 Approved
0.7816 Intermediate Similarity NPD3882 Suspended
0.7803 Intermediate Similarity NPD1465 Phase 2
0.7803 Intermediate Similarity NPD2801 Approved
0.7797 Intermediate Similarity NPD3787 Discontinued
0.7771 Intermediate Similarity NPD3749 Approved
0.7758 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD7874 Approved
0.7751 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7749 Intermediate Similarity NPD6777 Approved
0.7749 Intermediate Similarity NPD6780 Approved
0.7749 Intermediate Similarity NPD6782 Approved
0.7749 Intermediate Similarity NPD6776 Approved
0.7749 Intermediate Similarity NPD6778 Approved
0.7749 Intermediate Similarity NPD6781 Approved
0.7749 Intermediate Similarity NPD6779 Approved
0.7722 Intermediate Similarity NPD3818 Discontinued
0.772 Intermediate Similarity NPD7698 Approved
0.772 Intermediate Similarity NPD7697 Approved
0.772 Intermediate Similarity NPD7696 Phase 3
0.7716 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD7783 Phase 2
0.7711 Intermediate Similarity NPD1549 Phase 2
0.7704 Intermediate Similarity NPD8151 Discontinued
0.7701 Intermediate Similarity NPD8455 Phase 2
0.768 Intermediate Similarity NPD8320 Phase 1
0.768 Intermediate Similarity NPD8319 Approved
0.7676 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD3226 Approved
0.7653 Intermediate Similarity NPD7701 Phase 2
0.7647 Intermediate Similarity NPD2534 Approved
0.7647 Intermediate Similarity NPD2533 Approved
0.7647 Intermediate Similarity NPD2532 Approved
0.7624 Intermediate Similarity NPD7228 Approved
0.7602 Intermediate Similarity NPD1512 Approved
0.7592 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7871 Phase 2
0.759 Intermediate Similarity NPD7870 Phase 2
0.759 Intermediate Similarity NPD2935 Discontinued
0.7572 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7552 Intermediate Similarity NPD7699 Phase 2
0.7552 Intermediate Similarity NPD7700 Phase 2
0.7545 Intermediate Similarity NPD2346 Discontinued
0.7538 Intermediate Similarity NPD7801 Approved
0.753 Intermediate Similarity NPD2799 Discontinued
0.753 Intermediate Similarity NPD3748 Approved
0.7515 Intermediate Similarity NPD4628 Phase 3
0.7515 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD6534 Approved
0.7487 Intermediate Similarity NPD6535 Approved
0.7485 Intermediate Similarity NPD2796 Approved
0.7485 Intermediate Similarity NPD1511 Approved
0.7485 Intermediate Similarity NPD1551 Phase 2
0.7457 Intermediate Similarity NPD920 Approved
0.7456 Intermediate Similarity NPD2800 Approved
0.7443 Intermediate Similarity NPD37 Approved
0.743 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.743 Intermediate Similarity NPD919 Approved
0.743 Intermediate Similarity NPD6234 Discontinued
0.7425 Intermediate Similarity NPD1510 Phase 2
0.7416 Intermediate Similarity NPD4967 Phase 2
0.7416 Intermediate Similarity NPD4966 Approved
0.7416 Intermediate Similarity NPD4965 Approved
0.7412 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD5953 Discontinued
0.7398 Intermediate Similarity NPD6823 Phase 2
0.7394 Intermediate Similarity NPD4060 Phase 1
0.7379 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD6355 Discontinued
0.7349 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD5124 Phase 1
0.7348 Intermediate Similarity NPD1247 Approved
0.7341 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD1607 Approved
0.7297 Intermediate Similarity NPD7286 Phase 2
0.7289 Intermediate Similarity NPD1240 Approved
0.7288 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7390 Discontinued
0.7273 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6798 Discontinued
0.7273 Intermediate Similarity NPD7240 Approved
0.7273 Intermediate Similarity NPD2313 Discontinued
0.7268 Intermediate Similarity NPD3926 Phase 2
0.7268 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD6190 Approved
0.7241 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD6233 Phase 2
0.7228 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD5711 Approved
0.7213 Intermediate Similarity NPD5710 Approved
0.7209 Intermediate Similarity NPD7003 Approved
0.7202 Intermediate Similarity NPD6651 Approved
0.7176 Intermediate Similarity NPD6100 Approved
0.7176 Intermediate Similarity NPD6099 Approved
0.7175 Intermediate Similarity NPD7458 Discontinued
0.7169 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7097 Phase 1
0.7158 Intermediate Similarity NPD7199 Phase 2
0.7152 Intermediate Similarity NPD4908 Phase 1
0.7151 Intermediate Similarity NPD1243 Approved
0.7143 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4360 Phase 2
0.7128 Intermediate Similarity NPD4363 Phase 3
0.7126 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD7229 Phase 3
0.7118 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD4625 Phase 3
0.7102 Intermediate Similarity NPD6273 Approved
0.709 Intermediate Similarity NPD7685 Pre-registration
0.7083 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD1613 Approved
0.7079 Intermediate Similarity NPD7584 Approved
0.7076 Intermediate Similarity NPD5408 Approved
0.7076 Intermediate Similarity NPD5405 Approved
0.7076 Intermediate Similarity NPD5406 Approved
0.7076 Intermediate Similarity NPD5404 Approved
0.7071 Intermediate Similarity NPD8285 Discontinued
0.7065 Intermediate Similarity NPD8127 Discontinued
0.7048 Intermediate Similarity NPD6832 Phase 2
0.7045 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD2403 Approved
0.7035 Intermediate Similarity NPD5762 Approved
0.7035 Intermediate Similarity NPD2344 Approved
0.7035 Intermediate Similarity NPD5763 Approved
0.7022 Intermediate Similarity NPD1653 Approved
0.7019 Intermediate Similarity NPD8404 Phase 2
0.7018 Intermediate Similarity NPD7033 Discontinued
0.7006 Intermediate Similarity NPD5049 Phase 3
0.6994 Remote Similarity NPD2424 Discontinued
0.699 Remote Similarity NPD6213 Phase 3
0.699 Remote Similarity NPD6214 Clinical (unspecified phase)
0.699 Remote Similarity NPD6212 Phase 3
0.6981 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6978 Remote Similarity NPD4288 Approved
0.6977 Remote Similarity NPD2438 Suspended
0.697 Remote Similarity NPD1203 Approved
0.697 Remote Similarity NPD2797 Approved
0.6968 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6967 Remote Similarity NPD7907 Approved
0.6967 Remote Similarity NPD8366 Approved
0.6964 Remote Similarity NPD3268 Approved
0.6964 Remote Similarity NPD7985 Registered
0.6964 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6954 Remote Similarity NPD1652 Phase 2
0.695 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6946 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6944 Remote Similarity NPD8067 Phase 3
0.6941 Remote Similarity NPD447 Suspended
0.6933 Remote Similarity NPD1610 Phase 2

  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