Structure

Physi-Chem Properties

Molecular Weight:  662.24
Volume:  653.718
LogP:  6.209
LogD:  2.905
LogS:  -4.875
# Rotatable Bonds:  9
TPSA:  148.44
# H-Bond Aceptor:  12
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.219
Synthetic Accessibility Score:  4.747
Fsp3:  0.389
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:  -5.529
MDCK Permeability:  3.382362046977505e-05
Pgp-inhibitor:  0.987
Pgp-substrate:  0.56
Human Intestinal Absorption (HIA):  0.554
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.192

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  63.72577667236328%
Volume Distribution (VD):  0.817
Pgp-substrate:  27.761491775512695%

ADMET: Metabolism

CYP1A2-inhibitor:  0.029
CYP1A2-substrate:  0.971
CYP2C19-inhibitor:  0.025
CYP2C19-substrate:  0.844
CYP2C9-inhibitor:  0.322
CYP2C9-substrate:  0.816
CYP2D6-inhibitor:  0.056
CYP2D6-substrate:  0.299
CYP3A4-inhibitor:  0.133
CYP3A4-substrate:  0.232

ADMET: Excretion

Clearance (CL):  3.088
Half-life (T1/2):  0.14

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.903
Drug-inuced Liver Injury (DILI):  0.971
AMES Toxicity:  0.326
Rat Oral Acute Toxicity:  0.29
Maximum Recommended Daily Dose:  0.363
Skin Sensitization:  0.245
Carcinogencity:  0.032
Eye Corrosion:  0.003
Eye Irritation:  0.28
Respiratory Toxicity:  0.482

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

  Natural Product: NPC118000

Natural Product ID:  NPC118000
Common Name*:   (3S,3's,4S,4's)-10,10'-Dihydroxy-7,7',9,9'-Tetramethoxy-3,3'-Dimethyl-3,3',4,4'-Tetrahydro-1H,1'h-5,5'-Bibenzo[G]Isochromene-4,4'-Diyl Diacetate
IUPAC Name:   [(3S,4S)-5-[(3S,4S)-4-acetyloxy-10-hydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl]-10-hydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-4-yl] acetate
Synonyms:  
Standard InCHIKey:  PEDZYCDSAWVMRN-DZEHZSJLSA-N
Standard InCHI:  InChI=1S/C36H38O12/c1-15-35(47-17(3)37)31-23(13-45-15)33(39)27-21(9-19(41-5)11-25(27)43-7)29(31)30-22-10-20(42-6)12-26(44-8)28(22)34(40)24-14-46-16(2)36(32(24)30)48-18(4)38/h9-12,15-16,35-36,39-40H,13-14H2,1-8H3/t15-,16-,35+,36+/m0/s1
SMILES:  C[C@H]1[C@H](c2c(CO1)c(c1c(cc(cc1OC)OC)c2c1c2cc(cc(c2c(c2CO[C@@H](C)[C@H](c12)OC(=O)C)O)OC)OC)O)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL269531
PubChem CID:   44445338
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001610] Arylnaphthalene 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
NPO32515 Cordyceps sp. Under-species n.a. n.a. n.a. n.a. n.a. PMID[17887724]
NPO32514 Cordyceps sp. Under-species n.a. n.a. n.a. n.a. n.a. PMID[17887724]
NPO21470 Conoideocrella tenuis Species Clavicipitaceae Eukaryota n.a. mycelium n.a. PMID[21473608]
NPO32716 conoideocrella tenuis bcc 18627 Species Clavicipitaceae Eukaryota n.a. n.a. n.a. PMID[21473608]
NPO21470 Conoideocrella tenuis Species Clavicipitaceae Eukaryota n.a. n.a. n.a. PMID[21473608]
NPO21470 Conoideocrella tenuis Species Clavicipitaceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 4400.0 nM PMID[454108]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 22000.0 nM PMID[454108]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 71000.0 nM PMID[454108]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 75000.0 nM PMID[454108]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 3300.0 nM PMID[454107]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 10000.0 nM PMID[454108]
NPT115 Organism Mycobacterium tuberculosis H37Ra Mycobacterium tuberculosis H37Ra MIC > 75000.0 nM PMID[454108]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 IC50 > 75000.0 nM PMID[454108]

☑ 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 NPC118000 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 NPC162976
1.0 High Similarity NPC205501
0.9514 High Similarity NPC174251
0.9514 High Similarity NPC153182
0.9444 High Similarity NPC274454
0.9444 High Similarity NPC215678
0.9028 High Similarity NPC273623
0.8889 High Similarity NPC472646
0.8889 High Similarity NPC71465
0.8867 High Similarity NPC321657
0.8867 High Similarity NPC318373
0.8819 High Similarity NPC472649
0.8819 High Similarity NPC170328
0.8819 High Similarity NPC133463
0.8819 High Similarity NPC191462
0.8819 High Similarity NPC206525
0.8819 High Similarity NPC472648
0.8819 High Similarity NPC472647
0.8792 High Similarity NPC471608
0.875 High Similarity NPC258780
0.875 High Similarity NPC37410
0.8733 High Similarity NPC262297
0.8667 High Similarity NPC126291
0.8658 High Similarity NPC475492
0.8658 High Similarity NPC36732
0.863 High Similarity NPC470307
0.863 High Similarity NPC470308
0.8618 High Similarity NPC470208
0.8618 High Similarity NPC295573
0.8601 High Similarity NPC282508
0.8581 High Similarity NPC277331
0.8581 High Similarity NPC100482
0.8562 High Similarity NPC477612
0.8562 High Similarity NPC471522
0.8543 High Similarity NPC96576
0.8543 High Similarity NPC14468
0.8535 High Similarity NPC125495
0.8531 High Similarity NPC254000
0.8523 High Similarity NPC472087
0.8523 High Similarity NPC186033
0.8523 High Similarity NPC183709
0.8523 High Similarity NPC472088
0.8516 High Similarity NPC475141
0.8503 High Similarity NPC266006
0.8497 Intermediate Similarity NPC211561
0.8487 Intermediate Similarity NPC236202
0.8487 Intermediate Similarity NPC70409
0.8487 Intermediate Similarity NPC204770
0.8487 Intermediate Similarity NPC108811
0.8487 Intermediate Similarity NPC202742
0.8487 Intermediate Similarity NPC263940
0.8487 Intermediate Similarity NPC82917
0.8487 Intermediate Similarity NPC262911
0.8487 Intermediate Similarity NPC294558
0.8487 Intermediate Similarity NPC18185
0.8487 Intermediate Similarity NPC58190
0.8487 Intermediate Similarity NPC170103
0.8472 Intermediate Similarity NPC473309
0.8472 Intermediate Similarity NPC471517
0.8462 Intermediate Similarity NPC473736
0.8456 Intermediate Similarity NPC472089
0.8452 Intermediate Similarity NPC476452
0.8452 Intermediate Similarity NPC233467
0.8452 Intermediate Similarity NPC473018
0.8452 Intermediate Similarity NPC279406
0.8452 Intermediate Similarity NPC59692
0.8452 Intermediate Similarity NPC226809
0.8452 Intermediate Similarity NPC476391
0.8452 Intermediate Similarity NPC120633
0.8438 Intermediate Similarity NPC476200
0.8438 Intermediate Similarity NPC192258
0.8438 Intermediate Similarity NPC12326
0.8431 Intermediate Similarity NPC281549
0.8425 Intermediate Similarity NPC476615
0.8425 Intermediate Similarity NPC473107
0.8425 Intermediate Similarity NPC476617
0.8425 Intermediate Similarity NPC476616
0.8421 Intermediate Similarity NPC248053
0.8421 Intermediate Similarity NPC474054
0.8421 Intermediate Similarity NPC155564
0.8421 Intermediate Similarity NPC102280
0.8415 Intermediate Similarity NPC477836
0.8411 Intermediate Similarity NPC87883
0.8397 Intermediate Similarity NPC224161
0.8395 Intermediate Similarity NPC477835
0.8395 Intermediate Similarity NPC9309
0.8392 Intermediate Similarity NPC38017
0.8392 Intermediate Similarity NPC215300
0.8392 Intermediate Similarity NPC471064
0.8389 Intermediate Similarity NPC472092
0.8389 Intermediate Similarity NPC472091
0.8389 Intermediate Similarity NPC12668
0.8389 Intermediate Similarity NPC472090
0.8389 Intermediate Similarity NPC308768
0.8387 Intermediate Similarity NPC471403
0.8387 Intermediate Similarity NPC259707
0.838 Intermediate Similarity NPC82299
0.8378 Intermediate Similarity NPC22902
0.8377 Intermediate Similarity NPC476969
0.8375 Intermediate Similarity NPC177100
0.8375 Intermediate Similarity NPC139540
0.8366 Intermediate Similarity NPC111134
0.8366 Intermediate Similarity NPC474397
0.8366 Intermediate Similarity NPC112819
0.8366 Intermediate Similarity NPC133209
0.8366 Intermediate Similarity NPC6702
0.8355 Intermediate Similarity NPC125617
0.8355 Intermediate Similarity NPC43716
0.8355 Intermediate Similarity NPC101255
0.8355 Intermediate Similarity NPC86069
0.8355 Intermediate Similarity NPC475719
0.8345 Intermediate Similarity NPC160623
0.8344 Intermediate Similarity NPC46335
0.8344 Intermediate Similarity NPC268484
0.8344 Intermediate Similarity NPC157333
0.8344 Intermediate Similarity NPC8712
0.8333 Intermediate Similarity NPC322899
0.8333 Intermediate Similarity NPC44192
0.8333 Intermediate Similarity NPC46283
0.8333 Intermediate Similarity NPC325860
0.8333 Intermediate Similarity NPC265075
0.8333 Intermediate Similarity NPC471518
0.8333 Intermediate Similarity NPC469944
0.8333 Intermediate Similarity NPC226108
0.8333 Intermediate Similarity NPC272552
0.8333 Intermediate Similarity NPC134911
0.8333 Intermediate Similarity NPC471519
0.8323 Intermediate Similarity NPC469706
0.8323 Intermediate Similarity NPC174311
0.8323 Intermediate Similarity NPC182368
0.8323 Intermediate Similarity NPC225815
0.8323 Intermediate Similarity NPC24425
0.8323 Intermediate Similarity NPC185955
0.8323 Intermediate Similarity NPC145979
0.8323 Intermediate Similarity NPC469707
0.8323 Intermediate Similarity NPC9933
0.8323 Intermediate Similarity NPC218801
0.8323 Intermediate Similarity NPC214326
0.8323 Intermediate Similarity NPC15374
0.8323 Intermediate Similarity NPC260781
0.8323 Intermediate Similarity NPC218041
0.8322 Intermediate Similarity NPC243759
0.8322 Intermediate Similarity NPC275061
0.8322 Intermediate Similarity NPC105847
0.8322 Intermediate Similarity NPC53781
0.8322 Intermediate Similarity NPC218131
0.8322 Intermediate Similarity NPC243996
0.8322 Intermediate Similarity NPC220344
0.8322 Intermediate Similarity NPC132804
0.8322 Intermediate Similarity NPC257947
0.8322 Intermediate Similarity NPC473221
0.8312 Intermediate Similarity NPC227516
0.8312 Intermediate Similarity NPC20757
0.8311 Intermediate Similarity NPC141717
0.831 Intermediate Similarity NPC293801
0.8302 Intermediate Similarity NPC4809
0.8302 Intermediate Similarity NPC73517
0.8302 Intermediate Similarity NPC147743
0.8301 Intermediate Similarity NPC40222
0.8301 Intermediate Similarity NPC233980
0.8301 Intermediate Similarity NPC268515
0.8294 Intermediate Similarity NPC473686
0.8294 Intermediate Similarity NPC221140
0.8294 Intermediate Similarity NPC475352
0.8294 Intermediate Similarity NPC475220
0.8294 Intermediate Similarity NPC229817
0.8289 Intermediate Similarity NPC171932
0.8289 Intermediate Similarity NPC28440
0.8289 Intermediate Similarity NPC473108
0.8289 Intermediate Similarity NPC471824
0.8289 Intermediate Similarity NPC473845
0.8284 Intermediate Similarity NPC475662
0.8284 Intermediate Similarity NPC473631
0.8284 Intermediate Similarity NPC293227
0.8284 Intermediate Similarity NPC473717
0.828 Intermediate Similarity NPC476154
0.828 Intermediate Similarity NPC20050
0.828 Intermediate Similarity NPC115203
0.828 Intermediate Similarity NPC223720
0.828 Intermediate Similarity NPC306267
0.8278 Intermediate Similarity NPC175838
0.8269 Intermediate Similarity NPC302915
0.8261 Intermediate Similarity NPC155754
0.8261 Intermediate Similarity NPC109061
0.8261 Intermediate Similarity NPC124747
0.8258 Intermediate Similarity NPC475250
0.8258 Intermediate Similarity NPC107862
0.8258 Intermediate Similarity NPC148516
0.8258 Intermediate Similarity NPC177172
0.8258 Intermediate Similarity NPC474393
0.8258 Intermediate Similarity NPC122980
0.8258 Intermediate Similarity NPC180605
0.8258 Intermediate Similarity NPC474347
0.8255 Intermediate Similarity NPC230919
0.8255 Intermediate Similarity NPC865
0.8255 Intermediate Similarity NPC56329
0.8255 Intermediate Similarity NPC200935
0.8255 Intermediate Similarity NPC266453
0.8255 Intermediate Similarity NPC242715
0.8255 Intermediate Similarity NPC151656

  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 NPC118000 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
0.8375 Intermediate Similarity NPD6959 Discontinued
0.8151 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD7228 Approved
0.8113 Intermediate Similarity NPD8455 Phase 2
0.8082 Intermediate Similarity NPD4625 Phase 3
0.8072 Intermediate Similarity NPD5844 Phase 1
0.8014 Intermediate Similarity NPD4908 Phase 1
0.7988 Intermediate Similarity NPD6232 Discontinued
0.7952 Intermediate Similarity NPD7473 Discontinued
0.7937 Intermediate Similarity NPD37 Approved
0.7914 Intermediate Similarity NPD6234 Discontinued
0.7901 Intermediate Similarity NPD4967 Phase 2
0.7901 Intermediate Similarity NPD4966 Approved
0.7901 Intermediate Similarity NPD4965 Approved
0.7901 Intermediate Similarity NPD7768 Phase 2
0.7836 Intermediate Similarity NPD8312 Approved
0.7836 Intermediate Similarity NPD8313 Approved
0.78 Intermediate Similarity NPD4060 Phase 1
0.7791 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD7819 Suspended
0.7765 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD7240 Approved
0.7714 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD1613 Approved
0.7667 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD6674 Discontinued
0.7628 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD3027 Phase 3
0.7584 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7581 Intermediate Similarity NPD8151 Discontinued
0.758 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD7229 Phase 3
0.7551 Intermediate Similarity NPD4749 Approved
0.7547 Intermediate Similarity NPD7390 Discontinued
0.7534 Intermediate Similarity NPD1610 Phase 2
0.7533 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD7097 Phase 1
0.7531 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD7075 Discontinued
0.7517 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD4626 Approved
0.7516 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD5124 Phase 1
0.7514 Intermediate Similarity NPD6559 Discontinued
0.75 Intermediate Similarity NPD2532 Approved
0.75 Intermediate Similarity NPD2534 Approved
0.75 Intermediate Similarity NPD2533 Approved
0.7485 Intermediate Similarity NPD4380 Phase 2
0.7471 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD6166 Phase 2
0.7471 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD7003 Approved
0.7455 Intermediate Similarity NPD1465 Phase 2
0.7448 Intermediate Similarity NPD5691 Approved
0.7442 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD7411 Suspended
0.7436 Intermediate Similarity NPD6100 Approved
0.7436 Intermediate Similarity NPD2438 Suspended
0.7436 Intermediate Similarity NPD6099 Approved
0.7434 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7199 Phase 2
0.7391 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD5763 Approved
0.7389 Intermediate Similarity NPD7266 Discontinued
0.7389 Intermediate Similarity NPD5762 Approved
0.7358 Intermediate Similarity NPD3750 Approved
0.7351 Intermediate Similarity NPD2861 Phase 2
0.7349 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD5408 Approved
0.7325 Intermediate Similarity NPD5405 Approved
0.7325 Intermediate Similarity NPD5404 Approved
0.7325 Intermediate Similarity NPD5406 Approved
0.7312 Intermediate Similarity NPD7680 Approved
0.731 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7074 Phase 3
0.7297 Intermediate Similarity NPD1611 Approved
0.7284 Intermediate Similarity NPD7447 Phase 1
0.7283 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1283 Approved
0.726 Intermediate Similarity NPD1548 Phase 1
0.7256 Intermediate Similarity NPD1653 Approved
0.7251 Intermediate Similarity NPD3787 Discontinued
0.7247 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7054 Approved
0.7235 Intermediate Similarity NPD6746 Phase 2
0.7233 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD4140 Approved
0.7226 Intermediate Similarity NPD2979 Phase 3
0.7225 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD7783 Phase 2
0.7222 Intermediate Similarity NPD7212 Phase 2
0.7222 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7041 Phase 2
0.7222 Intermediate Similarity NPD7213 Phase 3
0.7219 Intermediate Similarity NPD3749 Approved
0.7212 Intermediate Similarity NPD7458 Discontinued
0.7212 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD6798 Discontinued
0.72 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7472 Approved
0.7193 Intermediate Similarity NPD8127 Discontinued
0.7191 Intermediate Similarity NPD8053 Approved
0.7191 Intermediate Similarity NPD8054 Approved
0.7188 Intermediate Similarity NPD1652 Phase 2
0.7186 Intermediate Similarity NPD1934 Approved
0.7181 Intermediate Similarity NPD422 Phase 1
0.7176 Intermediate Similarity NPD5709 Phase 3
0.7175 Intermediate Similarity NPD7808 Phase 3
0.7175 Intermediate Similarity NPD7549 Discontinued
0.7152 Intermediate Similarity NPD6696 Suspended
0.7143 Intermediate Similarity NPD7095 Approved
0.7135 Intermediate Similarity NPD4666 Phase 3
0.7128 Intermediate Similarity NPD7696 Phase 3
0.7128 Intermediate Similarity NPD7697 Approved
0.7128 Intermediate Similarity NPD7698 Approved
0.7128 Intermediate Similarity NPD7435 Discontinued
0.7119 Intermediate Similarity NPD7251 Discontinued
0.7118 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD8150 Discontinued
0.7108 Intermediate Similarity NPD3226 Approved
0.7107 Intermediate Similarity NPD2935 Discontinued
0.7097 Intermediate Similarity NPD7985 Registered
0.709 Intermediate Similarity NPD7870 Phase 2
0.709 Intermediate Similarity NPD7871 Phase 2
0.7086 Intermediate Similarity NPD7177 Discontinued
0.7083 Intermediate Similarity NPD6801 Discontinued
0.7081 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD6355 Discontinued
0.7067 Intermediate Similarity NPD1281 Approved
0.7062 Intermediate Similarity NPD6797 Phase 2
0.7052 Intermediate Similarity NPD5710 Approved
0.7052 Intermediate Similarity NPD5711 Approved
0.7051 Intermediate Similarity NPD6233 Phase 2
0.7045 Intermediate Similarity NPD8156 Discontinued
0.7044 Intermediate Similarity NPD3748 Approved
0.7039 Intermediate Similarity NPD8651 Approved
0.7037 Intermediate Similarity NPD7982 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD8166 Discontinued
0.7037 Intermediate Similarity NPD4628 Phase 3
0.7035 Intermediate Similarity NPD5494 Approved
0.703 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD4097 Suspended
0.7013 Intermediate Similarity NPD5736 Approved
0.7013 Intermediate Similarity NPD3018 Phase 2
0.7006 Intermediate Similarity NPD3620 Phase 2
0.7006 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5402 Approved
0.7 Intermediate Similarity NPD3817 Phase 2
0.6995 Remote Similarity NPD7874 Approved
0.6995 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6989 Remote Similarity NPD8099 Discontinued
0.6989 Remote Similarity NPD3751 Discontinued
0.6989 Remote Similarity NPD8252 Approved
0.6989 Remote Similarity NPD8251 Approved
0.6987 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6984 Remote Similarity NPD6823 Phase 2
0.698 Remote Similarity NPD1651 Approved
0.6979 Remote Similarity NPD7701 Phase 2
0.6968 Remote Similarity NPD6777 Approved
0.6968 Remote Similarity NPD6776 Approved
0.6968 Remote Similarity NPD6779 Approved
0.6968 Remote Similarity NPD6781 Approved
0.6968 Remote Similarity NPD6778 Approved
0.6968 Remote Similarity NPD6780 Approved
0.6968 Remote Similarity NPD6782 Approved
0.6964 Remote Similarity NPD6599 Discontinued
0.6962 Remote Similarity NPD5735 Approved
0.6957 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6957 Remote Similarity NPD2346 Discontinued
0.6957 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6941 Remote Similarity NPD5929 Approved
0.6933 Remote Similarity NPD5125 Phase 3
0.6933 Remote Similarity NPD5126 Approved
0.6928 Remote Similarity NPD6273 Approved
0.6914 Remote Similarity NPD1549 Phase 2
0.6911 Remote Similarity NPD8320 Phase 1
0.6911 Remote Similarity NPD8319 Approved
0.6909 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6894 Remote Similarity NPD2531 Phase 2
0.6894 Remote Similarity NPD1551 Phase 2
0.6892 Remote Similarity NPD7340 Approved
0.6889 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6886 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6886 Remote Similarity NPD5403 Approved
0.6879 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4538 Approved
0.6875 Remote Similarity NPD4750 Phase 3
0.6875 Remote Similarity NPD4536 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data