Structure

Physi-Chem Properties

Molecular Weight:  430.16
Volume:  418.085
LogP:  2.903
LogD:  3.241
LogS:  -4.585
# Rotatable Bonds:  6
TPSA:  73.84
# H-Bond Aceptor:  8
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.689
Synthetic Accessibility Score:  3.858
Fsp3:  0.478
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:  -4.847
MDCK Permeability:  5.536917160497978e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.001
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.324
Plasma Protein Binding (PPB):  71.05159759521484%
Volume Distribution (VD):  0.721
Pgp-substrate:  11.713094711303711%

ADMET: Metabolism

CYP1A2-inhibitor:  0.04
CYP1A2-substrate:  0.976
CYP2C19-inhibitor:  0.234
CYP2C19-substrate:  0.912
CYP2C9-inhibitor:  0.33
CYP2C9-substrate:  0.657
CYP2D6-inhibitor:  0.226
CYP2D6-substrate:  0.875
CYP3A4-inhibitor:  0.915
CYP3A4-substrate:  0.912

ADMET: Excretion

Clearance (CL):  9.024
Half-life (T1/2):  0.254

ADMET: Toxicity

hERG Blockers:  0.52
Human Hepatotoxicity (H-HT):  0.154
Drug-inuced Liver Injury (DILI):  0.89
AMES Toxicity:  0.152
Rat Oral Acute Toxicity:  0.02
Maximum Recommended Daily Dose:  0.761
Skin Sensitization:  0.951
Carcinogencity:  0.349
Eye Corrosion:  0.003
Eye Irritation:  0.047
Respiratory Toxicity:  0.394

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

  Natural Product: NPC25333

Natural Product ID:  NPC25333
Common Name*:   6-[(3S,3Ar,6R,6Ar)-6-(3,4,5-Trimethoxyphenyl)-1,3,3A,4,6,6A-Hexahydrofuro[3,4-C]Furan-3-Yl]-4-Methoxy-1,3-Benzodioxole
IUPAC Name:   6-[(3S,3aR,6R,6aR)-6-(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-4-methoxy-1,3-benzodioxole
Synonyms:  
Standard InCHIKey:  DHWUVPPRBIJJKS-LATRNWQMSA-N
Standard InCHI:  InChI=1S/C23H26O8/c1-24-16-5-12(6-17(25-2)22(16)27-4)20-14-9-29-21(15(14)10-28-20)13-7-18(26-3)23-19(8-13)30-11-31-23/h5-8,14-15,20-21H,9-11H2,1-4H3/t14-,15-,20-,21+/m0/s1
SMILES:  COc1cc(cc(c1OC)OC)[C@@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1cc(OC)c2c(c1)OCO2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2374864
PubChem CID:   12697528
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans

*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
NPO14110 Marrubium peregrinum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11013 Tephrosia polyphylla Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15660 Afzelia bella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14110 Marrubium peregrinum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17430 Acacia retinoide Species Fabaceae 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
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 10000.0 nM PMID[497410]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 26915.35 nM PMID[497410]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 51286.14 nM PMID[497410]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 31622.78 nM PMID[497410]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 69823.24 nM PMID[497410]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 89125.09 nM PMID[497410]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 96827.79 nM PMID[497410]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 49545.02 nM PMID[497410]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 92469.82 nM PMID[497410]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 57942.87 nM PMID[497410]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 43251.38 nM PMID[497410]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 50118.72 nM PMID[497410]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 46131.76 nM PMID[497410]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 49090.79 nM PMID[497410]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 52360.04 nM PMID[497410]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 42169.65 nM PMID[497410]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[497410]

☑ 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 NPC25333 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 NPC49235
1.0 High Similarity NPC148893
0.9922 High Similarity NPC31530
0.9845 High Similarity NPC189474
0.9771 High Similarity NPC113550
0.9766 High Similarity NPC65183
0.9766 High Similarity NPC261812
0.9766 High Similarity NPC72046
0.9697 High Similarity NPC46591
0.969 High Similarity NPC136750
0.969 High Similarity NPC266848
0.9624 High Similarity NPC312199
0.9618 High Similarity NPC121651
0.9549 High Similarity NPC56091
0.9535 High Similarity NPC192255
0.9535 High Similarity NPC82111
0.9535 High Similarity NPC227160
0.9481 High Similarity NPC185071
0.9481 High Similarity NPC12728
0.947 High Similarity NPC11453
0.9457 High Similarity NPC271208
0.9457 High Similarity NPC233224
0.9453 High Similarity NPC328682
0.9453 High Similarity NPC54321
0.9453 High Similarity NPC281864
0.9412 High Similarity NPC141569
0.9412 High Similarity NPC166884
0.9412 High Similarity NPC477701
0.9407 High Similarity NPC474295
0.9398 High Similarity NPC283949
0.9394 High Similarity NPC150534
0.9389 High Similarity NPC1474
0.9375 High Similarity NPC8050
0.9375 High Similarity NPC473092
0.9375 High Similarity NPC473093
0.9338 High Similarity NPC255566
0.9338 High Similarity NPC298317
0.9313 High Similarity NPC158526
0.9313 High Similarity NPC16830
0.9313 High Similarity NPC100223
0.9313 High Similarity NPC129687
0.9313 High Similarity NPC33611
0.9313 High Similarity NPC171928
0.9313 High Similarity NPC7744
0.9302 High Similarity NPC82862
0.9302 High Similarity NPC57119
0.9302 High Similarity NPC165128
0.9302 High Similarity NPC222127
0.9302 High Similarity NPC158471
0.9302 High Similarity NPC226862
0.9265 High Similarity NPC311057
0.9265 High Similarity NPC287124
0.9259 High Similarity NPC103448
0.9259 High Similarity NPC226547
0.9259 High Similarity NPC177868
0.9259 High Similarity NPC216434
0.9254 High Similarity NPC185908
0.9248 High Similarity NPC474139
0.9203 High Similarity NPC205316
0.9179 High Similarity NPC143895
0.9173 High Similarity NPC47181
0.9147 High Similarity NPC186845
0.9147 High Similarity NPC9891
0.9147 High Similarity NPC88297
0.9147 High Similarity NPC112571
0.9147 High Similarity NPC285725
0.9147 High Similarity NPC50683
0.913 High Similarity NPC92693
0.913 High Similarity NPC218841
0.9124 High Similarity NPC80326
0.9124 High Similarity NPC472562
0.9104 High Similarity NPC236522
0.9104 High Similarity NPC18576
0.9098 High Similarity NPC196937
0.9077 High Similarity NPC158737
0.9065 High Similarity NPC477702
0.9051 High Similarity NPC300798
0.9051 High Similarity NPC58137
0.9044 High Similarity NPC123526
0.9044 High Similarity NPC193666
0.9044 High Similarity NPC88640
0.9037 High Similarity NPC32189
0.9 High Similarity NPC212890
0.9 High Similarity NPC193779
0.8993 High Similarity NPC177644
0.8993 High Similarity NPC191158
0.8992 High Similarity NPC34902
0.8992 High Similarity NPC121783
0.8992 High Similarity NPC18449
0.8986 High Similarity NPC174522
0.8986 High Similarity NPC151423
0.8986 High Similarity NPC40237
0.8971 High Similarity NPC474039
0.8971 High Similarity NPC469981
0.8971 High Similarity NPC101807
0.8963 High Similarity NPC165155
0.8963 High Similarity NPC34103
0.8963 High Similarity NPC141765
0.8963 High Similarity NPC24490
0.8929 High Similarity NPC180953
0.8929 High Similarity NPC475868
0.8921 High Similarity NPC474808
0.8921 High Similarity NPC218510
0.8921 High Similarity NPC76415
0.8913 High Similarity NPC471908
0.8905 High Similarity NPC9068
0.8889 High Similarity NPC256776
0.8889 High Similarity NPC185680
0.8889 High Similarity NPC145722
0.8889 High Similarity NPC170779
0.8889 High Similarity NPC90083
0.8881 High Similarity NPC147616
0.8881 High Similarity NPC259742
0.8881 High Similarity NPC104077
0.8881 High Similarity NPC219671
0.8873 High Similarity NPC248132
0.8873 High Similarity NPC130449
0.8872 High Similarity NPC470624
0.8872 High Similarity NPC237169
0.8857 High Similarity NPC326144
0.8857 High Similarity NPC472712
0.8857 High Similarity NPC172171
0.8857 High Similarity NPC187774
0.8857 High Similarity NPC472713
0.8857 High Similarity NPC239254
0.8857 High Similarity NPC118385
0.8857 High Similarity NPC475000
0.8857 High Similarity NPC473046
0.8849 High Similarity NPC210354
0.8849 High Similarity NPC176586
0.8832 High Similarity NPC196420
0.8824 High Similarity NPC135777
0.8824 High Similarity NPC142547
0.8824 High Similarity NPC126409
0.8824 High Similarity NPC99572
0.8819 High Similarity NPC164082
0.8811 High Similarity NPC35877
0.8811 High Similarity NPC95392
0.8811 High Similarity NPC51328
0.8811 High Similarity NPC85141
0.8811 High Similarity NPC55158
0.8811 High Similarity NPC240521
0.8811 High Similarity NPC55715
0.8811 High Similarity NPC286235
0.8797 High Similarity NPC476748
0.8794 High Similarity NPC327651
0.8794 High Similarity NPC318286
0.8786 High Similarity NPC474288
0.8786 High Similarity NPC324962
0.8786 High Similarity NPC265154
0.8768 High Similarity NPC156376
0.876 High Similarity NPC312713
0.876 High Similarity NPC301641
0.876 High Similarity NPC126935
0.876 High Similarity NPC65933
0.876 High Similarity NPC172676
0.876 High Similarity NPC80241
0.876 High Similarity NPC216929
0.876 High Similarity NPC57268
0.8759 High Similarity NPC78047
0.8759 High Similarity NPC197166
0.8759 High Similarity NPC25695
0.8759 High Similarity NPC172818
0.875 High Similarity NPC244983
0.875 High Similarity NPC326095
0.875 High Similarity NPC473989
0.8741 High Similarity NPC475856
0.8741 High Similarity NPC71726
0.8741 High Similarity NPC204215
0.8741 High Similarity NPC175067
0.8732 High Similarity NPC252286
0.8732 High Similarity NPC321696
0.8732 High Similarity NPC321958
0.8732 High Similarity NPC154971
0.8731 High Similarity NPC63574
0.8731 High Similarity NPC134764
0.8731 High Similarity NPC171550
0.8723 High Similarity NPC50696
0.8723 High Similarity NPC179521
0.8714 High Similarity NPC5262
0.8714 High Similarity NPC246947
0.8714 High Similarity NPC229172
0.8714 High Similarity NPC230538
0.8714 High Similarity NPC36531
0.8714 High Similarity NPC472714
0.8714 High Similarity NPC103637
0.869 High Similarity NPC210642
0.869 High Similarity NPC13985
0.869 High Similarity NPC303519
0.8686 High Similarity NPC174191
0.8681 High Similarity NPC477698
0.8681 High Similarity NPC177476
0.8681 High Similarity NPC262455
0.8676 High Similarity NPC158331
0.8676 High Similarity NPC58585
0.8671 High Similarity NPC116019
0.8671 High Similarity NPC39657
0.8667 High Similarity NPC473412
0.8667 High Similarity NPC469698
0.8662 High Similarity NPC178014

  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 NPC25333 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
0.8615 High Similarity NPD3705 Approved
0.84 Intermediate Similarity NPD4966 Approved
0.84 Intermediate Similarity NPD4965 Approved
0.84 Intermediate Similarity NPD4967 Phase 2
0.8289 Intermediate Similarity NPD6234 Discontinued
0.8248 Intermediate Similarity NPD3027 Phase 3
0.82 Intermediate Similarity NPD37 Approved
0.8062 Intermediate Similarity NPD5283 Phase 1
0.8 Intermediate Similarity NPD2981 Phase 2
0.7941 Intermediate Similarity NPD2983 Phase 2
0.7941 Intermediate Similarity NPD2982 Phase 2
0.7925 Intermediate Similarity NPD7228 Approved
0.7867 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7842 Intermediate Similarity NPD3018 Phase 2
0.7834 Intermediate Similarity NPD7199 Phase 2
0.7736 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD7240 Approved
0.7692 Intermediate Similarity NPD1613 Approved
0.7692 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD1357 Approved
0.755 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD6674 Discontinued
0.7421 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD4908 Phase 1
0.7405 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD3818 Discontinued
0.7368 Intermediate Similarity NPD7124 Phase 2
0.7355 Intermediate Similarity NPD1653 Approved
0.7329 Intermediate Similarity NPD5494 Approved
0.7315 Intermediate Similarity NPD3539 Phase 1
0.731 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6111 Discontinued
0.7286 Intermediate Similarity NPD1610 Phase 2
0.7278 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD3384 Approved
0.7278 Intermediate Similarity NPD3382 Approved
0.7278 Intermediate Similarity NPD3383 Approved
0.7267 Intermediate Similarity NPD7266 Discontinued
0.7267 Intermediate Similarity NPD3540 Phase 1
0.7267 Intermediate Similarity NPD1375 Discontinued
0.7222 Intermediate Similarity NPD2861 Phase 2
0.7186 Intermediate Similarity NPD7074 Phase 3
0.7174 Intermediate Similarity NPD5536 Phase 2
0.7163 Intermediate Similarity NPD1091 Approved
0.7162 Intermediate Similarity NPD3657 Discovery
0.7143 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5058 Phase 3
0.7126 Intermediate Similarity NPD7054 Approved
0.7115 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD7680 Approved
0.7095 Intermediate Similarity NPD3620 Phase 2
0.7095 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD4005 Discontinued
0.7083 Intermediate Similarity NPD7472 Approved
0.7081 Intermediate Similarity NPD3817 Phase 2
0.7079 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD5111 Phase 2
0.7075 Intermediate Similarity NPD5109 Approved
0.7075 Intermediate Similarity NPD5110 Phase 2
0.7063 Intermediate Similarity NPD1934 Approved
0.7063 Intermediate Similarity NPD4749 Approved
0.7059 Intermediate Similarity NPD4236 Phase 3
0.7059 Intermediate Similarity NPD4237 Approved
0.7037 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD7157 Approved
0.7025 Intermediate Similarity NPD4210 Discontinued
0.702 Intermediate Similarity NPD4108 Discontinued
0.7019 Intermediate Similarity NPD2978 Approved
0.7019 Intermediate Similarity NPD2977 Approved
0.7013 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD4110 Phase 3
0.7 Intermediate Similarity NPD1548 Phase 1
0.6985 Remote Similarity NPD228 Approved
0.6974 Remote Similarity NPD2438 Suspended
0.6959 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6959 Remote Similarity NPD7808 Phase 3
0.6959 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6944 Remote Similarity NPD5327 Phase 3
0.6941 Remote Similarity NPD6797 Phase 2
0.6939 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6937 Remote Similarity NPD4675 Approved
0.6937 Remote Similarity NPD7028 Phase 2
0.6937 Remote Similarity NPD4678 Approved
0.6934 Remote Similarity NPD7843 Approved
0.6933 Remote Similarity NPD3882 Suspended
0.6914 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6914 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6908 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6908 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7466 Approved
0.6903 Remote Similarity NPD6331 Phase 2
0.6901 Remote Similarity NPD5126 Approved
0.6901 Remote Similarity NPD6559 Discontinued
0.6901 Remote Similarity NPD7251 Discontinued
0.6901 Remote Similarity NPD5125 Phase 3
0.6899 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6892 Remote Similarity NPD4625 Phase 3
0.689 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6889 Remote Similarity NPD2684 Approved
0.6886 Remote Similarity NPD3926 Phase 2
0.6886 Remote Similarity NPD5242 Approved
0.6879 Remote Similarity NPD4357 Discontinued
0.6875 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6871 Remote Similarity NPD5353 Approved
0.6867 Remote Similarity NPD4060 Phase 1
0.6863 Remote Similarity NPD2161 Phase 2
0.6863 Remote Similarity NPD3454 Phase 3
0.686 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6845 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6845 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6845 Remote Similarity NPD6166 Phase 2
0.6842 Remote Similarity NPD6895 Approved
0.6842 Remote Similarity NPD6896 Approved
0.6839 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6838 Remote Similarity NPD3021 Approved
0.6838 Remote Similarity NPD3022 Approved
0.6831 Remote Similarity NPD5585 Approved
0.6828 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6826 Remote Similarity NPD6232 Discontinued
0.6824 Remote Similarity NPD5844 Phase 1
0.6821 Remote Similarity NPD6355 Discontinued
0.6821 Remote Similarity NPD5735 Approved
0.6812 Remote Similarity NPD5535 Approved
0.681 Remote Similarity NPD2801 Approved
0.6805 Remote Similarity NPD7473 Discontinued
0.6802 Remote Similarity NPD7685 Pre-registration
0.68 Remote Similarity NPD554 Clinical (unspecified phase)
0.68 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6797 Remote Similarity NPD5588 Approved
0.6795 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6795 Remote Similarity NPD3892 Phase 2
0.6788 Remote Similarity NPD4055 Discovery
0.6783 Remote Similarity NPD17 Approved
0.6776 Remote Similarity NPD5006 Approved
0.6776 Remote Similarity NPD5005 Approved
0.6772 Remote Similarity NPD5297 Approved
0.6761 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6761 Remote Similarity NPD6842 Approved
0.6761 Remote Similarity NPD6841 Approved
0.6761 Remote Similarity NPD6843 Phase 3
0.6755 Remote Similarity NPD2238 Phase 2
0.6755 Remote Similarity NPD2979 Phase 3
0.6753 Remote Similarity NPD2796 Approved
0.6752 Remote Similarity NPD2219 Phase 1
0.6747 Remote Similarity NPD919 Approved
0.6742 Remote Similarity NPD7296 Approved
0.6732 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6732 Remote Similarity NPD7097 Phase 1
0.6732 Remote Similarity NPD4538 Approved
0.6732 Remote Similarity NPD4536 Approved
0.6731 Remote Similarity NPD5177 Phase 3
0.6731 Remote Similarity NPD3060 Approved
0.6715 Remote Similarity NPD5451 Approved
0.6713 Remote Similarity NPD5691 Approved
0.6712 Remote Similarity NPD3600 Clinical (unspecified phase)
0.671 Remote Similarity NPD5763 Approved
0.671 Remote Similarity NPD5762 Approved
0.6707 Remote Similarity NPD8455 Phase 2
0.6691 Remote Similarity NPD1358 Approved
0.6687 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2492 Phase 1
0.6667 Remote Similarity NPD6387 Discontinued
0.6667 Remote Similarity NPD7095 Approved
0.6667 Remote Similarity NPD1247 Approved
0.6667 Remote Similarity NPD8127 Discontinued
0.6667 Remote Similarity NPD2922 Phase 1
0.6667 Remote Similarity NPD7549 Discontinued
0.6667 Remote Similarity NPD8651 Approved
0.6648 Remote Similarity NPD4420 Approved
0.6646 Remote Similarity NPD5976 Discontinued
0.6646 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6645 Remote Similarity NPD1558 Phase 1
0.6645 Remote Similarity NPD4140 Approved
0.6644 Remote Similarity NPD1608 Approved
0.6644 Remote Similarity NPD1840 Phase 2
0.6643 Remote Similarity NPD1182 Approved
0.6628 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6627 Remote Similarity NPD3787 Discontinued
0.6627 Remote Similarity NPD7229 Phase 3
0.6626 Remote Similarity NPD4380 Phase 2
0.6625 Remote Similarity NPD4123 Phase 3
0.6624 Remote Similarity NPD1652 Phase 2
0.6624 Remote Similarity NPD4162 Approved
0.6623 Remote Similarity NPD5718 Phase 2
0.6619 Remote Similarity NPD1139 Approved
0.6619 Remote Similarity NPD1137 Approved
0.6618 Remote Similarity NPD3134 Approved
0.6606 Remote Similarity NPD7819 Suspended
0.6606 Remote Similarity NPD1465 Phase 2
0.6601 Remote Similarity NPD1933 Approved
0.6601 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6601 Remote Similarity NPD5124 Phase 1
0.6601 Remote Similarity NPD230 Phase 1

  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