Structure

Physi-Chem Properties

Molecular Weight:  1104.31
Volume:  1091.224
LogP:  8.491
LogD:  2.263
LogS:  -2.682
# Rotatable Bonds:  16
TPSA:  321.16
# H-Bond Aceptor:  20
# H-Bond Donor:  6
# Rings:  9
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.053
Synthetic Accessibility Score:  5.677
Fsp3:  0.262
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.366
MDCK Permeability:  1.0049144293589052e-05
Pgp-inhibitor:  0.887
Pgp-substrate:  0.308
Human Intestinal Absorption (HIA):  0.968
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  104.70990753173828%
Volume Distribution (VD):  -0.048
Pgp-substrate:  1.189745306968689%

ADMET: Metabolism

CYP1A2-inhibitor:  0.037
CYP1A2-substrate:  0.937
CYP2C19-inhibitor:  0.607
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.394
CYP2C9-substrate:  0.389
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.074
CYP3A4-inhibitor:  0.149
CYP3A4-substrate:  0.572

ADMET: Excretion

Clearance (CL):  1.319
Half-life (T1/2):  0.0

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.059
Drug-inuced Liver Injury (DILI):  0.98
AMES Toxicity:  0.124
Rat Oral Acute Toxicity:  0.078
Maximum Recommended Daily Dose:  0.991
Skin Sensitization:  0.024
Carcinogencity:  0.13
Eye Corrosion:  0.003
Eye Irritation:  0.925
Respiratory Toxicity:  0.002

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

  Natural Product: NPC475449

Natural Product ID:  NPC475449
Common Name*:   Scutianthraquinone D
IUPAC Name:   methyl 10-(1,6-dihydroxy-7-methoxycarbonyl-8-methyl-9,10-dioxoanthracen-2-yl)-7-[2,5-dihydroxy-3-methoxycarbonyl-4-methyl-9-(2-methylbutanoyloxy)-10-oxoanthracen-9-yl]-3,8-dihydroxy-1-methyl-10-(2-methylbutanoyloxy)-9-oxoanthracene-2-carboxylate
Synonyms:   Scutianthraquinone D
Standard InCHIKey:  UBSGRMBRWCDHGU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C61H52O20/c1-11-23(3)55(72)80-60(30-14-13-15-36(62)47(30)53(70)41-26(6)44(58(75)78-9)38(64)21-34(41)60)33-19-18-31-48(51(33)68)54(71)42-27(7)45(59(76)79-10)39(65)22-35(42)61(31,81-56(73)24(4)12-2)32-17-16-28-46(50(32)67)52(69)40-25(5)43(57(74)77-8)37(63)20-29(40)49(28)66/h13-24,62-65,67-68H,11-12H2,1-10H3
SMILES:  CCC(C(=O)OC1(c2cc(O)c(c(c2C(=O)c2c1ccc(c2O)C1(OC(=O)C(CC)C)c2cccc(c2C(=O)c2c1cc(O)c(c2C)C(=O)OC)O)C)C(=O)OC)c1ccc2c(c1O)C(=O)c1c(C2=O)cc(c(c1C)C(=O)OC)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL505862
PubChem CID:   44157003
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0001911] Anthracenecarboxylic acids and derivatives
          • [CHEMONTID:0002424] Anthracenecarboxylic acids

*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
NPO1248 Scutia myrtina Species Rhamnaceae Eukaryota roots n.a. n.a. PMID[17378532]
NPO1248 Scutia myrtina Species Rhamnaceae Eukaryota n.a. bark n.a. PMID[19282186]
NPO1248 Scutia myrtina Species Rhamnaceae Eukaryota n.a. Madagascar forest n.a. PMID[19282186]
NPO1248 Scutia myrtina Species Rhamnaceae 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
NPT179 Cell Line A2780 Homo sapiens IC50 = 4300.0 nM PMID[451018]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 3680.0 nM PMID[451018]
NPT2 Others Unspecified Ratio IC50 = 1.2 n.a. PMID[451018]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 5600.0 nM PMID[451018]
NPT2 Others Unspecified Ratio IC50 = 0.8 n.a. PMID[451018]

☑ 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 NPC475449 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
0.9934 High Similarity NPC326084
0.9868 High Similarity NPC317580
0.9735 High Similarity NPC318270
0.9007 High Similarity NPC66593
0.8861 High Similarity NPC66029
0.8846 High Similarity NPC205766
0.8846 High Similarity NPC315520
0.8831 High Similarity NPC147250
0.8831 High Similarity NPC314437
0.8774 High Similarity NPC119767
0.8758 High Similarity NPC471682
0.8693 High Similarity NPC257644
0.8688 High Similarity NPC474861
0.8675 High Similarity NPC4214
0.8645 High Similarity NPC471683
0.8642 High Similarity NPC470342
0.8642 High Similarity NPC472052
0.8642 High Similarity NPC472060
0.8623 High Similarity NPC477836
0.8606 High Similarity NPC477835
0.8571 High Similarity NPC19631
0.8571 High Similarity NPC239136
0.8562 High Similarity NPC474622
0.8562 High Similarity NPC470408
0.8562 High Similarity NPC474621
0.8562 High Similarity NPC225243
0.8562 High Similarity NPC474824
0.8562 High Similarity NPC182921
0.8562 High Similarity NPC218870
0.8554 High Similarity NPC76647
0.8537 High Similarity NPC315772
0.8535 High Similarity NPC37709
0.8528 High Similarity NPC476506
0.8519 High Similarity NPC263483
0.8516 High Similarity NPC53016
0.8516 High Similarity NPC296752
0.85 High Similarity NPC474533
0.85 High Similarity NPC474534
0.8477 Intermediate Similarity NPC80035
0.8476 Intermediate Similarity NPC472261
0.8471 Intermediate Similarity NPC271944
0.8471 Intermediate Similarity NPC110882
0.8471 Intermediate Similarity NPC85393
0.8442 Intermediate Similarity NPC315578
0.8434 Intermediate Similarity NPC71390
0.8431 Intermediate Similarity NPC13715
0.8428 Intermediate Similarity NPC477221
0.8418 Intermediate Similarity NPC478018
0.8412 Intermediate Similarity NPC477992
0.8412 Intermediate Similarity NPC477991
0.8408 Intermediate Similarity NPC478019
0.8397 Intermediate Similarity NPC295712
0.8397 Intermediate Similarity NPC313047
0.8397 Intermediate Similarity NPC474203
0.8397 Intermediate Similarity NPC293545
0.8397 Intermediate Similarity NPC451542
0.8397 Intermediate Similarity NPC174905
0.8395 Intermediate Similarity NPC226656
0.8395 Intermediate Similarity NPC66508
0.8377 Intermediate Similarity NPC26924
0.8354 Intermediate Similarity NPC470570
0.8354 Intermediate Similarity NPC324736
0.8344 Intermediate Similarity NPC193703
0.8344 Intermediate Similarity NPC227841
0.8344 Intermediate Similarity NPC21599
0.8343 Intermediate Similarity NPC478021
0.8333 Intermediate Similarity NPC69755
0.8333 Intermediate Similarity NPC193555
0.8323 Intermediate Similarity NPC478022
0.8323 Intermediate Similarity NPC168471
0.8323 Intermediate Similarity NPC478020
0.8313 Intermediate Similarity NPC97637
0.8313 Intermediate Similarity NPC187934
0.8304 Intermediate Similarity NPC70862
0.8302 Intermediate Similarity NPC290194
0.8294 Intermediate Similarity NPC294501
0.8293 Intermediate Similarity NPC67197
0.8291 Intermediate Similarity NPC34482
0.8284 Intermediate Similarity NPC175477
0.8282 Intermediate Similarity NPC266469
0.8274 Intermediate Similarity NPC30027
0.8269 Intermediate Similarity NPC290550
0.8266 Intermediate Similarity NPC72783
0.8263 Intermediate Similarity NPC476505
0.8261 Intermediate Similarity NPC477914
0.8253 Intermediate Similarity NPC189552
0.8253 Intermediate Similarity NPC273467
0.825 Intermediate Similarity NPC221352
0.8247 Intermediate Similarity NPC62272
0.8246 Intermediate Similarity NPC65118
0.8239 Intermediate Similarity NPC143685
0.8232 Intermediate Similarity NPC478027
0.8232 Intermediate Similarity NPC474360
0.8232 Intermediate Similarity NPC146211
0.8228 Intermediate Similarity NPC48762
0.8225 Intermediate Similarity NPC253730
0.8225 Intermediate Similarity NPC234497
0.8225 Intermediate Similarity NPC470341
0.8225 Intermediate Similarity NPC107009
0.8225 Intermediate Similarity NPC286230
0.8225 Intermediate Similarity NPC324522
0.8225 Intermediate Similarity NPC472058
0.8225 Intermediate Similarity NPC105414
0.8224 Intermediate Similarity NPC225051
0.8224 Intermediate Similarity NPC472591
0.8217 Intermediate Similarity NPC85310
0.821 Intermediate Similarity NPC477276
0.8208 Intermediate Similarity NPC478000
0.8205 Intermediate Similarity NPC169452
0.8205 Intermediate Similarity NPC181560
0.8193 Intermediate Similarity NPC185617
0.8193 Intermediate Similarity NPC312993
0.8193 Intermediate Similarity NPC186325
0.8193 Intermediate Similarity NPC284495
0.8187 Intermediate Similarity NPC10842
0.8187 Intermediate Similarity NPC183441
0.8187 Intermediate Similarity NPC473113
0.8182 Intermediate Similarity NPC475352
0.8182 Intermediate Similarity NPC475220
0.8182 Intermediate Similarity NPC155211
0.8182 Intermediate Similarity NPC208258
0.8182 Intermediate Similarity NPC473686
0.8182 Intermediate Similarity NPC229817
0.8182 Intermediate Similarity NPC221140
0.8176 Intermediate Similarity NPC12402
0.8171 Intermediate Similarity NPC473631
0.8171 Intermediate Similarity NPC472807
0.8171 Intermediate Similarity NPC475662
0.8171 Intermediate Similarity NPC3898
0.8171 Intermediate Similarity NPC37253
0.8171 Intermediate Similarity NPC293227
0.8171 Intermediate Similarity NPC473717
0.8171 Intermediate Similarity NPC79375
0.8171 Intermediate Similarity NPC471456
0.817 Intermediate Similarity NPC287604
0.817 Intermediate Similarity NPC161964
0.817 Intermediate Similarity NPC288089
0.817 Intermediate Similarity NPC472262
0.8166 Intermediate Similarity NPC251336
0.8161 Intermediate Similarity NPC473785
0.8155 Intermediate Similarity NPC473009
0.8153 Intermediate Similarity NPC246638
0.815 Intermediate Similarity NPC170018
0.815 Intermediate Similarity NPC176246
0.815 Intermediate Similarity NPC76112
0.815 Intermediate Similarity NPC66820
0.815 Intermediate Similarity NPC92403
0.8144 Intermediate Similarity NPC18380
0.8144 Intermediate Similarity NPC137232
0.8141 Intermediate Similarity NPC242994
0.8141 Intermediate Similarity NPC138099
0.814 Intermediate Similarity NPC472054
0.8137 Intermediate Similarity NPC172329
0.8137 Intermediate Similarity NPC152233
0.8137 Intermediate Similarity NPC2569
0.8133 Intermediate Similarity NPC55443
0.8133 Intermediate Similarity NPC18699
0.8133 Intermediate Similarity NPC474373
0.8133 Intermediate Similarity NPC177650
0.8121 Intermediate Similarity NPC54830
0.8121 Intermediate Similarity NPC56049
0.8113 Intermediate Similarity NPC10764
0.8113 Intermediate Similarity NPC79627
0.811 Intermediate Similarity NPC214632
0.811 Intermediate Similarity NPC324447
0.811 Intermediate Similarity NPC477691
0.811 Intermediate Similarity NPC208806
0.8107 Intermediate Similarity NPC473010
0.8107 Intermediate Similarity NPC169471
0.8107 Intermediate Similarity NPC469664
0.8105 Intermediate Similarity NPC43627
0.8105 Intermediate Similarity NPC52407
0.8105 Intermediate Similarity NPC53896
0.8105 Intermediate Similarity NPC115458
0.8103 Intermediate Similarity NPC207467
0.8101 Intermediate Similarity NPC469520
0.8098 Intermediate Similarity NPC35
0.8095 Intermediate Similarity NPC15374
0.8095 Intermediate Similarity NPC473012
0.8089 Intermediate Similarity NPC275903
0.8086 Intermediate Similarity NPC474310
0.8086 Intermediate Similarity NPC247219
0.8086 Intermediate Similarity NPC327962
0.8086 Intermediate Similarity NPC329933
0.8084 Intermediate Similarity NPC121647
0.8084 Intermediate Similarity NPC226462
0.8084 Intermediate Similarity NPC98023
0.8084 Intermediate Similarity NPC195136
0.8084 Intermediate Similarity NPC292863
0.8084 Intermediate Similarity NPC184326
0.8081 Intermediate Similarity NPC478002
0.8079 Intermediate Similarity NPC87583
0.8075 Intermediate Similarity NPC261271
0.8075 Intermediate Similarity NPC312929
0.8075 Intermediate Similarity NPC126767
0.8075 Intermediate Similarity NPC289042
0.8075 Intermediate Similarity NPC118027
0.8075 Intermediate Similarity NPC245584
0.8075 Intermediate Similarity NPC125801
0.8075 Intermediate Similarity NPC475348

  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 NPC475449 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
0.8344 Intermediate Similarity NPD7390 Discontinued
0.8274 Intermediate Similarity NPD7473 Discontinued
0.8247 Intermediate Similarity NPD5404 Approved
0.8247 Intermediate Similarity NPD5406 Approved
0.8247 Intermediate Similarity NPD5405 Approved
0.8247 Intermediate Similarity NPD5408 Approved
0.8199 Intermediate Similarity NPD3226 Approved
0.815 Intermediate Similarity NPD8312 Approved
0.815 Intermediate Similarity NPD8313 Approved
0.8107 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD6232 Discontinued
0.8038 Intermediate Similarity NPD7003 Approved
0.8036 Intermediate Similarity NPD6959 Discontinued
0.8034 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD8150 Discontinued
0.8 Intermediate Similarity NPD7819 Suspended
0.7952 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD2935 Discontinued
0.7879 Intermediate Similarity NPD7411 Suspended
0.7866 Intermediate Similarity NPD7458 Discontinued
0.7848 Intermediate Similarity NPD2346 Discontinued
0.7798 Intermediate Similarity NPD7768 Phase 2
0.773 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD8166 Discontinued
0.766 Intermediate Similarity NPD8320 Phase 1
0.766 Intermediate Similarity NPD8319 Approved
0.7651 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD3749 Approved
0.764 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD2533 Approved
0.7622 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD2534 Approved
0.7622 Intermediate Similarity NPD2532 Approved
0.761 Intermediate Similarity NPD2799 Discontinued
0.7592 Intermediate Similarity NPD8151 Discontinued
0.7582 Intermediate Similarity NPD1470 Approved
0.7566 Intermediate Similarity NPD7870 Phase 2
0.7566 Intermediate Similarity NPD7871 Phase 2
0.7564 Intermediate Similarity NPD3764 Approved
0.7527 Intermediate Similarity NPD7699 Phase 2
0.7527 Intermediate Similarity NPD7700 Phase 2
0.7513 Intermediate Similarity NPD7435 Discontinued
0.7469 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD6535 Approved
0.7459 Intermediate Similarity NPD6534 Approved
0.7458 Intermediate Similarity NPD5844 Phase 1
0.7442 Intermediate Similarity NPD7075 Discontinued
0.7421 Intermediate Similarity NPD7698 Approved
0.7421 Intermediate Similarity NPD7696 Phase 3
0.7421 Intermediate Similarity NPD7697 Approved
0.741 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD4380 Phase 2
0.7374 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7874 Approved
0.7354 Intermediate Similarity NPD6776 Approved
0.7354 Intermediate Similarity NPD6777 Approved
0.7354 Intermediate Similarity NPD6779 Approved
0.7354 Intermediate Similarity NPD6782 Approved
0.7354 Intermediate Similarity NPD6778 Approved
0.7354 Intermediate Similarity NPD6781 Approved
0.7354 Intermediate Similarity NPD6780 Approved
0.7342 Intermediate Similarity NPD2313 Discontinued
0.732 Intermediate Similarity NPD1201 Approved
0.7312 Intermediate Similarity NPD6212 Phase 3
0.7312 Intermediate Similarity NPD6213 Phase 3
0.7312 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD2344 Approved
0.7283 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3750 Approved
0.7268 Intermediate Similarity NPD7701 Phase 2
0.7267 Intermediate Similarity NPD1607 Approved
0.7267 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD6273 Approved
0.7245 Intermediate Similarity NPD7801 Approved
0.7244 Intermediate Similarity NPD1164 Approved
0.7233 Intermediate Similarity NPD3268 Approved
0.7228 Intermediate Similarity NPD8434 Phase 2
0.7225 Intermediate Similarity NPD8438 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD8285 Discontinued
0.7207 Intermediate Similarity NPD7177 Discontinued
0.7191 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD6166 Phase 2
0.7179 Intermediate Similarity NPD1283 Approved
0.7178 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1510 Phase 2
0.7178 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD7783 Phase 2
0.7152 Intermediate Similarity NPD9493 Approved
0.7143 Intermediate Similarity NPD1240 Approved
0.7143 Intermediate Similarity NPD6559 Discontinued
0.7126 Intermediate Similarity NPD2309 Approved
0.7111 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD6801 Discontinued
0.7107 Intermediate Similarity NPD6832 Phase 2
0.7101 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD6823 Phase 2
0.7093 Intermediate Similarity NPD6599 Discontinued
0.7091 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD1471 Phase 3
0.7089 Intermediate Similarity NPD2798 Approved
0.7083 Intermediate Similarity NPD7236 Approved
0.7079 Intermediate Similarity NPD5711 Approved
0.7079 Intermediate Similarity NPD5710 Approved
0.7077 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7239 Suspended
0.7073 Intermediate Similarity NPD4308 Phase 3
0.7069 Intermediate Similarity NPD8455 Phase 2
0.7069 Intermediate Similarity NPD2801 Approved
0.7066 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD7008 Discontinued
0.7062 Intermediate Similarity NPD5494 Approved
0.7048 Intermediate Similarity NPD1549 Phase 2
0.7045 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD943 Approved
0.7037 Intermediate Similarity NPD2979 Phase 3
0.7033 Intermediate Similarity NPD7472 Approved
0.7033 Intermediate Similarity NPD7074 Phase 3
0.7029 Intermediate Similarity NPD3817 Phase 2
0.7025 Intermediate Similarity NPD1203 Approved
0.7011 Intermediate Similarity NPD1934 Approved
0.7011 Intermediate Similarity NPD7808 Phase 3
0.6995 Remote Similarity NPD5953 Discontinued
0.6988 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6988 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6987 Remote Similarity NPD1281 Approved
0.6983 Remote Similarity NPD7229 Phase 3
0.6982 Remote Similarity NPD3300 Phase 2
0.6978 Remote Similarity NPD7054 Approved
0.6975 Remote Similarity NPD6663 Approved
0.6971 Remote Similarity NPD1465 Phase 2
0.697 Remote Similarity NPD3748 Approved
0.6968 Remote Similarity NPD4626 Approved
0.6964 Remote Similarity NPD4628 Phase 3
0.6957 Remote Similarity NPD7251 Discontinued
0.6957 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6941 Remote Similarity NPD6799 Approved
0.6941 Remote Similarity NPD1511 Approved
0.6937 Remote Similarity NPD5736 Approved
0.6932 Remote Similarity NPD5402 Approved
0.6928 Remote Similarity NPD6100 Approved
0.6928 Remote Similarity NPD1551 Phase 2
0.6928 Remote Similarity NPD2796 Approved
0.6928 Remote Similarity NPD2438 Suspended
0.6928 Remote Similarity NPD6099 Approved
0.6923 Remote Similarity NPD6190 Approved
0.6923 Remote Similarity NPD3818 Discontinued
0.6918 Remote Similarity NPD2797 Approved
0.6918 Remote Similarity NPD3266 Approved
0.6918 Remote Similarity NPD3267 Approved
0.6914 Remote Similarity NPD411 Approved
0.6909 Remote Similarity NPD7097 Phase 1
0.6902 Remote Similarity NPD6797 Phase 2
0.6893 Remote Similarity NPD3882 Suspended
0.689 Remote Similarity NPD447 Suspended
0.689 Remote Similarity NPD230 Phase 1
0.689 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6885 Remote Similarity NPD7286 Phase 2
0.6871 Remote Similarity NPD8032 Phase 2
0.6869 Remote Similarity NPD6973 Clinical (unspecified phase)
0.6867 Remote Similarity NPD651 Clinical (unspecified phase)
0.6864 Remote Similarity NPD1878 Clinical (unspecified phase)
0.686 Remote Similarity NPD1512 Approved
0.6859 Remote Similarity NPD3019 Approved
0.6851 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6848 Remote Similarity NPD6651 Approved
0.6839 Remote Similarity NPD9545 Approved
0.6835 Remote Similarity NPD9717 Approved
0.6835 Remote Similarity NPD3972 Approved
0.6833 Remote Similarity NPD8127 Discontinued
0.6831 Remote Similarity NPD7228 Approved
0.6831 Remote Similarity NPD3751 Discontinued
0.6829 Remote Similarity NPD4307 Phase 2
0.6829 Remote Similarity NPD4060 Phase 1
0.6828 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6821 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6821 Remote Similarity NPD920 Approved
0.6818 Remote Similarity NPD37 Approved
0.6816 Remote Similarity NPD6234 Discontinued
0.6805 Remote Similarity NPD2800 Approved
0.68 Remote Similarity NPD6585 Discontinued
0.6798 Remote Similarity NPD4967 Phase 2
0.6798 Remote Similarity NPD4965 Approved
0.6798 Remote Similarity NPD4966 Approved
0.6797 Remote Similarity NPD5951 Approved
0.6796 Remote Similarity NPD6808 Phase 2
0.6795 Remote Similarity NPD1651 Approved
0.6795 Remote Similarity NPD5691 Approved
0.6789 Remote Similarity NPD4287 Approved
0.6774 Remote Similarity NPD7685 Pre-registration
0.6768 Remote Similarity NPD7961 Discontinued

  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