Structure

Physi-Chem Properties

Molecular Weight:  730.3
Volume:  743.482
LogP:  4.788
LogD:  3.627
LogS:  -5.221
# Rotatable Bonds:  17
TPSA:  148.44
# H-Bond Aceptor:  12
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.11
Synthetic Accessibility Score:  4.411
Fsp3:  0.366
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:  -5.306
MDCK Permeability:  5.609205618384294e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  92.01734161376953%
Volume Distribution (VD):  0.398
Pgp-substrate:  2.3297934532165527%

ADMET: Metabolism

CYP1A2-inhibitor:  0.278
CYP1A2-substrate:  0.956
CYP2C19-inhibitor:  0.803
CYP2C19-substrate:  0.609
CYP2C9-inhibitor:  0.941
CYP2C9-substrate:  0.931
CYP2D6-inhibitor:  0.743
CYP2D6-substrate:  0.947
CYP3A4-inhibitor:  0.991
CYP3A4-substrate:  0.933

ADMET: Excretion

Clearance (CL):  6.621
Half-life (T1/2):  0.124

ADMET: Toxicity

hERG Blockers:  0.167
Human Hepatotoxicity (H-HT):  0.1
Drug-inuced Liver Injury (DILI):  0.926
AMES Toxicity:  0.053
Rat Oral Acute Toxicity:  0.029
Maximum Recommended Daily Dose:  0.031
Skin Sensitization:  0.021
Carcinogencity:  0.234
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.007

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

  Natural Product: NPC100425

Natural Product ID:  NPC100425
Common Name*:   (8S,8'r)-7,7'-Dioxo-Seco-Manassantin B
IUPAC Name:   (2S,3R)-1-[4-[(1R,2R)-1-(1,3-benzodioxol-5-yl)-1-hydroxypropan-2-yl]oxy-3-methoxyphenyl]-4-[4-[(1R,2R)-1-(3,4-dimethoxyphenyl)-1-hydroxypropan-2-yl]oxy-3-methoxyphenyl]-2,3-dimethylbutane-1,4-dione
Synonyms:  
Standard InCHIKey:  APNXRQITXDDCJC-AAKSZLAOSA-N
Standard InCHI:  InChI=1S/C41H46O12/c1-22(38(42)26-11-15-32(35(17-26)48-7)52-24(3)40(44)28-9-13-30(46-5)34(19-28)47-6)23(2)39(43)27-12-16-33(36(18-27)49-8)53-25(4)41(45)29-10-14-31-37(20-29)51-21-50-31/h9-20,22-25,40-41,44-45H,21H2,1-8H3/t22-,23+,24-,25-,40+,41+/m1/s1
SMILES:  C[C@H]([C@H](C)C(=O)c1ccc(c(c1)OC)O[C@H](C)[C@@H](c1ccc2c(c1)OCO2)O)C(=O)c1ccc(c(c1)OC)O[C@H](C)[C@@H](c1ccc(c(c1)OC)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3105546
PubChem CID:   76321153
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001969] Dibenzylbutane 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
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[10924192]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[11754613]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. root n.a. PMID[14750033]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[15482936]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota roots n.a. n.a. PMID[18841903]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota Roots n.a. n.a. PMID[24359277]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota Aerial Parts n.a. n.a. PMID[24387347]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[31642320]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20323 Saururus chinensis Species Saururaceae 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
NPT2 Others Unspecified Ratio CC50/EC50 = 12.4 n.a. PMID[500136]
NPT27 Others Unspecified CC50 > 200000.0 nM PMID[500136]
NPT164 Organism Human herpesvirus 4 Human herpesvirus 4 EC50 = 16200.0 nM PMID[500136]

☑ 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 NPC100425 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
0.9091 High Similarity NPC316539
0.8896 High Similarity NPC45943
0.8868 High Similarity NPC469888
0.8834 High Similarity NPC148273
0.882 High Similarity NPC133984
0.8812 High Similarity NPC10205
0.8805 High Similarity NPC137813
0.8773 High Similarity NPC216916
0.8758 High Similarity NPC471405
0.8743 High Similarity NPC180768
0.8742 High Similarity NPC267091
0.8742 High Similarity NPC36130
0.8742 High Similarity NPC134905
0.8727 High Similarity NPC475738
0.8718 High Similarity NPC241846
0.8718 High Similarity NPC93610
0.8712 High Similarity NPC476373
0.8706 High Similarity NPC267549
0.8704 High Similarity NPC226759
0.8679 High Similarity NPC243891
0.8667 High Similarity NPC100420
0.8647 High Similarity NPC79736
0.8647 High Similarity NPC67629
0.8639 High Similarity NPC199357
0.8639 High Similarity NPC105137
0.8634 High Similarity NPC191046
0.8634 High Similarity NPC194095
0.8634 High Similarity NPC327032
0.8616 High Similarity NPC229882
0.8616 High Similarity NPC205054
0.8616 High Similarity NPC158635
0.8608 High Similarity NPC304048
0.8608 High Similarity NPC226153
0.8606 High Similarity NPC476371
0.8606 High Similarity NPC33298
0.8606 High Similarity NPC476372
0.8606 High Similarity NPC285108
0.8599 High Similarity NPC30890
0.8598 High Similarity NPC218471
0.8598 High Similarity NPC239818
0.8596 High Similarity NPC477880
0.8596 High Similarity NPC477882
0.859 High Similarity NPC46880
0.859 High Similarity NPC473090
0.8571 High Similarity NPC115466
0.8571 High Similarity NPC245615
0.8571 High Similarity NPC157898
0.8571 High Similarity NPC21956
0.8571 High Similarity NPC61604
0.8571 High Similarity NPC197708
0.8571 High Similarity NPC299706
0.8571 High Similarity NPC658
0.8563 High Similarity NPC43065
0.8553 High Similarity NPC111785
0.8547 High Similarity NPC471030
0.8545 High Similarity NPC149873
0.8545 High Similarity NPC469889
0.8545 High Similarity NPC7191
0.8544 High Similarity NPC24257
0.8544 High Similarity NPC153620
0.8544 High Similarity NPC99183
0.8529 High Similarity NPC172033
0.8529 High Similarity NPC88560
0.8529 High Similarity NPC175230
0.8528 High Similarity NPC261090
0.8528 High Similarity NPC11411
0.8521 High Similarity NPC135370
0.8521 High Similarity NPC212748
0.8516 High Similarity NPC28398
0.8512 High Similarity NPC473818
0.8509 High Similarity NPC478268
0.8506 High Similarity NPC260842
0.85 High Similarity NPC227980
0.8494 Intermediate Similarity NPC246024
0.8491 Intermediate Similarity NPC472969
0.8485 Intermediate Similarity NPC239966
0.8485 Intermediate Similarity NPC472961
0.8485 Intermediate Similarity NPC289346
0.8485 Intermediate Similarity NPC472962
0.8485 Intermediate Similarity NPC203020
0.848 Intermediate Similarity NPC473630
0.8471 Intermediate Similarity NPC261254
0.8471 Intermediate Similarity NPC102851
0.8471 Intermediate Similarity NPC469506
0.8471 Intermediate Similarity NPC5786
0.8471 Intermediate Similarity NPC235575
0.8466 Intermediate Similarity NPC254163
0.8466 Intermediate Similarity NPC131532
0.8466 Intermediate Similarity NPC7839
0.8466 Intermediate Similarity NPC142291
0.8466 Intermediate Similarity NPC180901
0.8466 Intermediate Similarity NPC300757
0.8462 Intermediate Similarity NPC216403
0.8462 Intermediate Similarity NPC95421
0.8462 Intermediate Similarity NPC202428
0.8462 Intermediate Similarity NPC198125
0.8462 Intermediate Similarity NPC302506
0.8462 Intermediate Similarity NPC61791
0.8462 Intermediate Similarity NPC41494
0.8462 Intermediate Similarity NPC229687
0.8462 Intermediate Similarity NPC149300
0.8462 Intermediate Similarity NPC266545
0.8462 Intermediate Similarity NPC186100
0.8457 Intermediate Similarity NPC131121
0.8457 Intermediate Similarity NPC308555
0.8448 Intermediate Similarity NPC132111
0.8448 Intermediate Similarity NPC321916
0.8448 Intermediate Similarity NPC35924
0.8448 Intermediate Similarity NPC476203
0.8448 Intermediate Similarity NPC199172
0.8448 Intermediate Similarity NPC473883
0.8447 Intermediate Similarity NPC62354
0.8439 Intermediate Similarity NPC80956
0.8438 Intermediate Similarity NPC476394
0.8438 Intermediate Similarity NPC98809
0.8434 Intermediate Similarity NPC99968
0.843 Intermediate Similarity NPC472723
0.843 Intermediate Similarity NPC473713
0.8424 Intermediate Similarity NPC160780
0.8424 Intermediate Similarity NPC289811
0.8424 Intermediate Similarity NPC478269
0.8424 Intermediate Similarity NPC68619
0.8421 Intermediate Similarity NPC476374
0.8421 Intermediate Similarity NPC477881
0.8418 Intermediate Similarity NPC327052
0.8415 Intermediate Similarity NPC163635
0.8412 Intermediate Similarity NPC44558
0.8412 Intermediate Similarity NPC105511
0.8412 Intermediate Similarity NPC204937
0.8412 Intermediate Similarity NPC149011
0.8412 Intermediate Similarity NPC476365
0.8412 Intermediate Similarity NPC52598
0.8409 Intermediate Similarity NPC65489
0.8405 Intermediate Similarity NPC287504
0.8405 Intermediate Similarity NPC25127
0.8402 Intermediate Similarity NPC135345
0.8402 Intermediate Similarity NPC229729
0.8402 Intermediate Similarity NPC177362
0.8402 Intermediate Similarity NPC45400
0.84 Intermediate Similarity NPC231254
0.84 Intermediate Similarity NPC318119
0.8397 Intermediate Similarity NPC470372
0.8395 Intermediate Similarity NPC151425
0.8395 Intermediate Similarity NPC289438
0.8393 Intermediate Similarity NPC165720
0.8393 Intermediate Similarity NPC477884
0.8391 Intermediate Similarity NPC469371
0.8385 Intermediate Similarity NPC473091
0.8383 Intermediate Similarity NPC61594
0.8383 Intermediate Similarity NPC56735
0.8383 Intermediate Similarity NPC4013
0.8383 Intermediate Similarity NPC125991
0.8383 Intermediate Similarity NPC145847
0.8383 Intermediate Similarity NPC90905
0.8382 Intermediate Similarity NPC47191
0.8382 Intermediate Similarity NPC241196
0.8382 Intermediate Similarity NPC472387
0.838 Intermediate Similarity NPC476358
0.8375 Intermediate Similarity NPC116229
0.8373 Intermediate Similarity NPC53889
0.8372 Intermediate Similarity NPC193377
0.8372 Intermediate Similarity NPC146803
0.8371 Intermediate Similarity NPC264302
0.8365 Intermediate Similarity NPC9370
0.8365 Intermediate Similarity NPC287495
0.8364 Intermediate Similarity NPC472860
0.8364 Intermediate Similarity NPC82733
0.8364 Intermediate Similarity NPC187205
0.8364 Intermediate Similarity NPC76458
0.8364 Intermediate Similarity NPC1913
0.8363 Intermediate Similarity NPC129930
0.8363 Intermediate Similarity NPC475155
0.8363 Intermediate Similarity NPC114550
0.8363 Intermediate Similarity NPC471920
0.8363 Intermediate Similarity NPC292712
0.8363 Intermediate Similarity NPC307518
0.8363 Intermediate Similarity NPC474075
0.8363 Intermediate Similarity NPC476370
0.8363 Intermediate Similarity NPC312006
0.8363 Intermediate Similarity NPC471921
0.8363 Intermediate Similarity NPC174700
0.8363 Intermediate Similarity NPC48773
0.8363 Intermediate Similarity NPC471922
0.8363 Intermediate Similarity NPC20114
0.8363 Intermediate Similarity NPC205076
0.8362 Intermediate Similarity NPC173872
0.8362 Intermediate Similarity NPC205721
0.8362 Intermediate Similarity NPC473618
0.8362 Intermediate Similarity NPC119094
0.8354 Intermediate Similarity NPC239608
0.8354 Intermediate Similarity NPC179521
0.8354 Intermediate Similarity NPC46161
0.8353 Intermediate Similarity NPC472383
0.8353 Intermediate Similarity NPC472381
0.8353 Intermediate Similarity NPC293629
0.8352 Intermediate Similarity NPC104910
0.8352 Intermediate Similarity NPC474093
0.8344 Intermediate Similarity NPC115203
0.8344 Intermediate Similarity NPC44730
0.8343 Intermediate Similarity NPC83049

  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 NPC100425 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
0.8512 High Similarity NPD3818 Discontinued
0.8418 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.8314 Intermediate Similarity NPD7685 Pre-registration
0.8304 Intermediate Similarity NPD7074 Phase 3
0.8261 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8246 Intermediate Similarity NPD7054 Approved
0.8229 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8198 Intermediate Similarity NPD7472 Approved
0.8193 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8192 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8161 Intermediate Similarity NPD7808 Phase 3
0.815 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8114 Intermediate Similarity NPD8313 Approved
0.8114 Intermediate Similarity NPD8312 Approved
0.8107 Intermediate Similarity NPD7199 Phase 2
0.807 Intermediate Similarity NPD6166 Phase 2
0.807 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.807 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD37 Approved
0.8 Intermediate Similarity NPD4628 Phase 3
0.8 Intermediate Similarity NPD7251 Discontinued
0.7976 Intermediate Similarity NPD4965 Approved
0.7976 Intermediate Similarity NPD4967 Phase 2
0.7976 Intermediate Similarity NPD4966 Approved
0.7964 Intermediate Similarity NPD8455 Phase 2
0.7955 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD6797 Phase 2
0.7941 Intermediate Similarity NPD5494 Approved
0.7931 Intermediate Similarity NPD5844 Phase 1
0.7907 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD1934 Approved
0.7895 Intermediate Similarity NPD8127 Discontinued
0.7882 Intermediate Similarity NPD6234 Discontinued
0.7874 Intermediate Similarity NPD7228 Approved
0.787 Intermediate Similarity NPD3882 Suspended
0.7831 Intermediate Similarity NPD7458 Discontinued
0.7829 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD7473 Discontinued
0.7802 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7797 Intermediate Similarity NPD6559 Discontinued
0.7751 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD2801 Approved
0.7716 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD3817 Phase 2
0.7706 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD8434 Phase 2
0.7644 Intermediate Similarity NPD6232 Discontinued
0.7598 Intermediate Similarity NPD7240 Approved
0.7593 Intermediate Similarity NPD7266 Discontinued
0.7574 Intermediate Similarity NPD4380 Phase 2
0.7571 Intermediate Similarity NPD3751 Discontinued
0.7545 Intermediate Similarity NPD6273 Approved
0.7544 Intermediate Similarity NPD1465 Phase 2
0.7544 Intermediate Similarity NPD7819 Suspended
0.7515 Intermediate Similarity NPD6190 Approved
0.7514 Intermediate Similarity NPD7075 Discontinued
0.75 Intermediate Similarity NPD3926 Phase 2
0.7486 Intermediate Similarity NPD6959 Discontinued
0.7485 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD7768 Phase 2
0.7443 Intermediate Similarity NPD3787 Discontinued
0.7442 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD7411 Suspended
0.7425 Intermediate Similarity NPD1511 Approved
0.7412 Intermediate Similarity NPD3226 Approved
0.7407 Intermediate Similarity NPD7097 Phase 1
0.7399 Intermediate Similarity NPD5402 Approved
0.7394 Intermediate Similarity NPD6674 Discontinued
0.7385 Intermediate Similarity NPD8151 Discontinued
0.7384 Intermediate Similarity NPD6801 Discontinued
0.7378 Intermediate Similarity NPD2344 Approved
0.7368 Intermediate Similarity NPD7028 Phase 2
0.7358 Intermediate Similarity NPD7870 Phase 2
0.7358 Intermediate Similarity NPD7871 Phase 2
0.7349 Intermediate Similarity NPD8166 Discontinued
0.7342 Intermediate Similarity NPD9494 Approved
0.7337 Intermediate Similarity NPD1512 Approved
0.733 Intermediate Similarity NPD6776 Approved
0.733 Intermediate Similarity NPD6779 Approved
0.733 Intermediate Similarity NPD6781 Approved
0.733 Intermediate Similarity NPD6777 Approved
0.733 Intermediate Similarity NPD6782 Approved
0.733 Intermediate Similarity NPD6778 Approved
0.733 Intermediate Similarity NPD6780 Approved
0.7326 Intermediate Similarity NPD6386 Approved
0.7326 Intermediate Similarity NPD6385 Approved
0.7314 Intermediate Similarity NPD3749 Approved
0.7312 Intermediate Similarity NPD3764 Approved
0.7308 Intermediate Similarity NPD7038 Approved
0.7308 Intermediate Similarity NPD7039 Approved
0.7306 Intermediate Similarity NPD7697 Approved
0.7306 Intermediate Similarity NPD7698 Approved
0.7306 Intermediate Similarity NPD7435 Discontinued
0.7306 Intermediate Similarity NPD7696 Phase 3
0.7284 Intermediate Similarity NPD6355 Discontinued
0.7278 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD1653 Approved
0.7246 Intermediate Similarity NPD4110 Phase 3
0.7246 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD7701 Phase 2
0.7244 Intermediate Similarity NPD1608 Approved
0.7229 Intermediate Similarity NPD1549 Phase 2
0.7222 Intermediate Similarity NPD7801 Approved
0.7219 Intermediate Similarity NPD6799 Approved
0.7216 Intermediate Similarity NPD7680 Approved
0.7212 Intermediate Similarity NPD2796 Approved
0.7209 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD6798 Discontinued
0.7202 Intermediate Similarity NPD2309 Approved
0.7197 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD5403 Approved
0.7179 Intermediate Similarity NPD3705 Approved
0.7178 Intermediate Similarity NPD230 Phase 1
0.7176 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD7874 Approved
0.7172 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD6599 Discontinued
0.716 Intermediate Similarity NPD6233 Phase 2
0.7152 Intermediate Similarity NPD2799 Discontinued
0.7143 Intermediate Similarity NPD3027 Phase 3
0.7143 Intermediate Similarity NPD3750 Approved
0.7136 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD7783 Phase 2
0.7135 Intermediate Similarity NPD7699 Phase 2
0.7135 Intermediate Similarity NPD7700 Phase 2
0.7112 Intermediate Similarity NPD8150 Discontinued
0.7098 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD1247 Approved
0.7092 Intermediate Similarity NPD8319 Approved
0.7092 Intermediate Similarity NPD8320 Phase 1
0.7088 Intermediate Similarity NPD7177 Discontinued
0.7086 Intermediate Similarity NPD7577 Discontinued
0.7079 Intermediate Similarity NPD919 Approved
0.7077 Intermediate Similarity NPD6823 Phase 2
0.7076 Intermediate Similarity NPD5401 Approved
0.7073 Intermediate Similarity NPD447 Suspended
0.7073 Intermediate Similarity NPD1933 Approved
0.7068 Intermediate Similarity NPD6535 Approved
0.7068 Intermediate Similarity NPD6534 Approved
0.7063 Intermediate Similarity NPD2798 Approved
0.7056 Intermediate Similarity NPD7229 Phase 3
0.7051 Intermediate Similarity NPD17 Approved
0.7048 Intermediate Similarity NPD1510 Phase 2
0.7045 Intermediate Similarity NPD5760 Phase 2
0.7045 Intermediate Similarity NPD5761 Phase 2
0.7041 Intermediate Similarity NPD7003 Approved
0.7037 Intermediate Similarity NPD7095 Approved
0.7017 Intermediate Similarity NPD5242 Approved
0.7012 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD1613 Approved
0.7006 Intermediate Similarity NPD5353 Approved
0.6995 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6995 Remote Similarity NPD2163 Approved
0.6994 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6987 Remote Similarity NPD1357 Approved
0.6978 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6968 Remote Similarity NPD5536 Phase 2
0.6964 Remote Similarity NPD2346 Discontinued
0.6959 Remote Similarity NPD7440 Discontinued
0.6946 Remote Similarity NPD7033 Discontinued
0.6946 Remote Similarity NPD3748 Approved
0.6941 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6937 Remote Similarity NPD1876 Approved
0.6928 Remote Similarity NPD6653 Approved
0.6927 Remote Similarity NPD6212 Phase 3
0.6927 Remote Similarity NPD6213 Phase 3
0.6927 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6918 Remote Similarity NPD3972 Approved
0.6914 Remote Similarity NPD2861 Phase 2
0.691 Remote Similarity NPD5978 Approved
0.691 Remote Similarity NPD5977 Approved
0.6909 Remote Similarity NPD1240 Approved
0.6909 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6908 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6907 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6905 Remote Similarity NPD2935 Discontinued
0.6902 Remote Similarity NPD7799 Discontinued
0.6901 Remote Similarity NPD2354 Approved
0.6901 Remote Similarity NPD3887 Approved
0.6893 Remote Similarity NPD6844 Discontinued
0.689 Remote Similarity NPD3268 Approved
0.689 Remote Similarity NPD2313 Discontinued
0.6884 Remote Similarity NPD7999 Approved
0.6879 Remote Similarity NPD2534 Approved
0.6879 Remote Similarity NPD2533 Approved
0.6879 Remote Similarity NPD2532 Approved
0.6878 Remote Similarity NPD8404 Phase 2
0.6871 Remote Similarity NPD4908 Phase 1
0.686 Remote Similarity NPD5058 Phase 3
0.6856 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5647 Approved
0.685 Remote Similarity NPD7584 Approved
0.6848 Remote Similarity NPD8032 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