Structure

Physi-Chem Properties

Molecular Weight:  680.2
Volume:  689.635
LogP:  6.652
LogD:  3.716
LogS:  -4.043
# Rotatable Bonds:  4
TPSA:  171.07
# H-Bond Aceptor:  9
# H-Bond Donor:  8
# Rings:  9
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.093
Synthetic Accessibility Score:  4.668
Fsp3:  0.143
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.204
MDCK Permeability:  5.456817689264426e-06
Pgp-inhibitor:  0.614
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.979
20% Bioavailability (F20%):  0.686
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  94.45276641845703%
Volume Distribution (VD):  0.628
Pgp-substrate:  5.1530232429504395%

ADMET: Metabolism

CYP1A2-inhibitor:  0.092
CYP1A2-substrate:  0.762
CYP2C19-inhibitor:  0.966
CYP2C19-substrate:  0.048
CYP2C9-inhibitor:  0.86
CYP2C9-substrate:  0.998
CYP2D6-inhibitor:  0.169
CYP2D6-substrate:  0.706
CYP3A4-inhibitor:  0.349
CYP3A4-substrate:  0.478

ADMET: Excretion

Clearance (CL):  7.518
Half-life (T1/2):  0.392

ADMET: Toxicity

hERG Blockers:  0.132
Human Hepatotoxicity (H-HT):  0.099
Drug-inuced Liver Injury (DILI):  0.712
AMES Toxicity:  0.272
Rat Oral Acute Toxicity:  0.889
Maximum Recommended Daily Dose:  0.982
Skin Sensitization:  0.951
Carcinogencity:  0.038
Eye Corrosion:  0.003
Eye Irritation:  0.898
Respiratory Toxicity:  0.033

Download Data

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

  Natural Product: NPC148516

Natural Product ID:  NPC148516
Common Name*:   Vaticanol A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MBGBQHRAJPLAPN-WTEBWGKASA-N
Standard InCHI:  InChI=1S/C42H32O9/c43-23-7-1-19(2-8-23)33-35(22-13-26(46)15-27(47)14-22)38-31(50)18-32-39-37(42(51-32)21-5-11-25(45)12-6-21)29-16-28(48)17-30(49)36(29)34(40(33)41(38)39)20-3-9-24(44)10-4-20/h1-18,33-35,37,40,42-50H/t33-,34-,35-,37-,40+,42+/m1/s1
SMILES:  c1cc(ccc1[C@@H]1[C@@H](c2cc(cc(c2)O)O)c2c(cc3c4[C@@H](c5cc(cc(c5[C@@H](c5ccc(cc5)O)[C@H]1c24)O)O)[C@H](c1ccc(cc1)O)O3)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL508745
PubChem CID:   44566412
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO5650 Eupatorium glutinosum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[12027751]
NPO1782 Piper caninum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[15270572]
NPO98 Leucosceptrum canum Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[15524427]
NPO6522 Polyalthia evecta Species Annonaceae Eukaryota roots n.a. n.a. PMID[16441071]
NPO6522 Polyalthia evecta Species Annonaceae Eukaryota n.a. root n.a. PMID[16441071]
NPO14000 Hopea exalata Species Dipterocarpaceae Eukaryota stem bark Botanical Garden at Jianfeng Town, Ledong County, Hainan Province, China 2004-JUL PMID[17190464]
NPO9804 Cinnamosma macrocarpa Species Canellaceae Eukaryota n.a. n.a. n.a. PMID[17286431]
NPO26194 Shorea roxburghii Species Dipterocarpaceae Eukaryota Barks n.a. n.a. PMID[22209731]
NPO11541 Curcuma xanthorrhiza Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2042 Garcinia bancana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10915 Heliotropium hirsutum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25661 Vatica rassak Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25661 Vatica rassak Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10915 Heliotropium hirsutum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2042 Garcinia bancana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11541 Curcuma xanthorrhiza Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16805 Senecio cisplatinus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14000 Hopea exalata Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26194 Shorea roxburghii Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25661 Vatica rassak Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9804 Cinnamosma macrocarpa Species Canellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14697 Ustilago esculenta Species Ustilaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13334 Senecio toluccanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11736 Bulla striata Species Bullidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11541 Curcuma xanthorrhiza Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14439 Marasmius oreades Species Marasmiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16691 Viguiera radula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14476 Sterculia alata Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11202 Maytenus imbricata Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO98 Leucosceptrum canum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10915 Heliotropium hirsutum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1782 Piper caninum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5650 Eupatorium glutinosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15640 Sideritis chamaedryfolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13778 Melandrium turkestanicum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO2042 Garcinia bancana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6522 Polyalthia evecta Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14958 Duguetia eximia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17995 Xeromphis spinosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9406 Cotula filicula Species Asteraceae 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
NPT462 Individual Protein Sucrase-isomaltase Rattus norvegicus IC50 = 148000.0 nM PMID[531419]
NPT826 Organism Magnaporthe oryzae Magnaporthe oryzae MIC = 3.12 ug.mL-1 PMID[531418]
NPT2705 Organism Alternaria solani Alternaria solani MIC = 6.25 ug.mL-1 PMID[531418]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum MIC = 12.7 ug.mL-1 PMID[531418]
NPT1199 Organism Valsa mali Valsa mali MIC = 20.1 ug.mL-1 PMID[531418]
NPT962 Organism Alternaria alternata Alternaria alternata MIC > 50.0 ug.mL-1 PMID[531418]
NPT2637 Organism Colletotrichum lagenarium Colletotrichum lagenarium MIC > 50.0 ug.mL-1 PMID[531418]
NPT671 Individual Protein Acidic alpha-glucosidase Rattus norvegicus IC50 = 218000.0 nM PMID[531419]
NPT68 Individual Protein Aldose reductase Rattus norvegicus IC50 = 23700.0 nM PMID[531419]

☑ 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 NPC148516 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 NPC177172
1.0 High Similarity NPC122980
1.0 High Similarity NPC180605
1.0 High Similarity NPC107862
0.986 High Similarity NPC224528
0.986 High Similarity NPC105073
0.986 High Similarity NPC233886
0.9718 High Similarity NPC111134
0.9653 High Similarity NPC218801
0.9586 High Similarity NPC157081
0.9521 High Similarity NPC120633
0.9521 High Similarity NPC473018
0.9444 High Similarity NPC6702
0.9444 High Similarity NPC242774
0.9444 High Similarity NPC133209
0.9444 High Similarity NPC237546
0.9444 High Similarity NPC224921
0.9444 High Similarity NPC231712
0.9444 High Similarity NPC112819
0.9306 High Similarity NPC149633
0.9241 High Similarity NPC14468
0.911 High Similarity NPC176804
0.911 High Similarity NPC71686
0.9091 High Similarity NPC174787
0.9091 High Similarity NPC213607
0.9091 High Similarity NPC182509
0.9078 High Similarity NPC11727
0.9078 High Similarity NPC15109
0.9078 High Similarity NPC125579
0.9007 High Similarity NPC157333
0.8951 High Similarity NPC470307
0.8951 High Similarity NPC470308
0.8947 High Similarity NPC202104
0.8881 High Similarity NPC471522
0.875 High Similarity NPC476391
0.875 High Similarity NPC141717
0.8716 High Similarity NPC304894
0.8716 High Similarity NPC15659
0.8699 High Similarity NPC273623
0.8671 High Similarity NPC473665
0.8662 High Similarity NPC237424
0.8662 High Similarity NPC473309
0.8662 High Similarity NPC238168
0.8662 High Similarity NPC48880
0.8649 High Similarity NPC163508
0.8649 High Similarity NPC173203
0.8627 High Similarity NPC233467
0.8627 High Similarity NPC59692
0.8611 High Similarity NPC476616
0.8611 High Similarity NPC476615
0.8611 High Similarity NPC476617
0.8611 High Similarity NPC473107
0.8609 High Similarity NPC20757
0.8609 High Similarity NPC329836
0.8609 High Similarity NPC227516
0.8608 High Similarity NPC261896
0.8592 High Similarity NPC254000
0.8562 High Similarity NPC472646
0.8562 High Similarity NPC71465
0.8552 High Similarity NPC258780
0.8552 High Similarity NPC37410
0.8521 High Similarity NPC471518
0.8521 High Similarity NPC471519
0.8514 High Similarity NPC277331
0.8514 High Similarity NPC100482
0.8506 High Similarity NPC226809
0.8506 High Similarity NPC279406
0.8497 Intermediate Similarity NPC477612
0.8493 Intermediate Similarity NPC170328
0.8493 Intermediate Similarity NPC472648
0.8493 Intermediate Similarity NPC133463
0.8493 Intermediate Similarity NPC472647
0.8493 Intermediate Similarity NPC206525
0.8493 Intermediate Similarity NPC472649
0.8493 Intermediate Similarity NPC191462
0.8467 Intermediate Similarity NPC475492
0.8452 Intermediate Similarity NPC224161
0.8442 Intermediate Similarity NPC324517
0.8442 Intermediate Similarity NPC329343
0.8442 Intermediate Similarity NPC321972
0.8421 Intermediate Similarity NPC204770
0.8421 Intermediate Similarity NPC70409
0.8421 Intermediate Similarity NPC108811
0.8421 Intermediate Similarity NPC82917
0.8421 Intermediate Similarity NPC202742
0.8421 Intermediate Similarity NPC236202
0.8421 Intermediate Similarity NPC18185
0.8421 Intermediate Similarity NPC262911
0.8421 Intermediate Similarity NPC294558
0.8421 Intermediate Similarity NPC174251
0.8421 Intermediate Similarity NPC153182
0.8421 Intermediate Similarity NPC58190
0.8421 Intermediate Similarity NPC170103
0.8421 Intermediate Similarity NPC263940
0.8414 Intermediate Similarity NPC469610
0.8411 Intermediate Similarity NPC181615
0.8403 Intermediate Similarity NPC300875
0.8403 Intermediate Similarity NPC236014
0.8403 Intermediate Similarity NPC282508
0.8403 Intermediate Similarity NPC476166
0.8403 Intermediate Similarity NPC8899
0.8403 Intermediate Similarity NPC207892
0.8403 Intermediate Similarity NPC280653
0.8403 Intermediate Similarity NPC17343
0.8403 Intermediate Similarity NPC471517
0.8403 Intermediate Similarity NPC181497
0.8403 Intermediate Similarity NPC129106
0.8403 Intermediate Similarity NPC228369
0.8403 Intermediate Similarity NPC164574
0.8403 Intermediate Similarity NPC150011
0.8403 Intermediate Similarity NPC268917
0.8403 Intermediate Similarity NPC271945
0.8403 Intermediate Similarity NPC118114
0.8403 Intermediate Similarity NPC12875
0.8403 Intermediate Similarity NPC196765
0.8403 Intermediate Similarity NPC129784
0.8403 Intermediate Similarity NPC206224
0.8397 Intermediate Similarity NPC46335
0.8356 Intermediate Similarity NPC296915
0.8356 Intermediate Similarity NPC225696
0.8356 Intermediate Similarity NPC198154
0.8356 Intermediate Similarity NPC223008
0.8356 Intermediate Similarity NPC115335
0.8356 Intermediate Similarity NPC97834
0.8355 Intermediate Similarity NPC96576
0.8355 Intermediate Similarity NPC260397
0.8355 Intermediate Similarity NPC215678
0.8355 Intermediate Similarity NPC274454
0.8345 Intermediate Similarity NPC469611
0.8345 Intermediate Similarity NPC13005
0.8333 Intermediate Similarity NPC277784
0.8333 Intermediate Similarity NPC27187
0.8333 Intermediate Similarity NPC470225
0.8323 Intermediate Similarity NPC471403
0.8313 Intermediate Similarity NPC90822
0.8312 Intermediate Similarity NPC470826
0.8312 Intermediate Similarity NPC295573
0.8312 Intermediate Similarity NPC211561
0.8312 Intermediate Similarity NPC470098
0.8312 Intermediate Similarity NPC321657
0.8312 Intermediate Similarity NPC473266
0.8312 Intermediate Similarity NPC318373
0.8312 Intermediate Similarity NPC476969
0.8312 Intermediate Similarity NPC470208
0.8311 Intermediate Similarity NPC94994
0.831 Intermediate Similarity NPC9292
0.831 Intermediate Similarity NPC145659
0.8301 Intermediate Similarity NPC320970
0.8301 Intermediate Similarity NPC320671
0.8301 Intermediate Similarity NPC262297
0.8301 Intermediate Similarity NPC328567
0.8301 Intermediate Similarity NPC327412
0.8264 Intermediate Similarity NPC93962
0.8258 Intermediate Similarity NPC118000
0.8258 Intermediate Similarity NPC205501
0.8258 Intermediate Similarity NPC162976
0.8239 Intermediate Similarity NPC73517
0.8239 Intermediate Similarity NPC147743
0.8239 Intermediate Similarity NPC125495
0.8239 Intermediate Similarity NPC113495
0.8239 Intermediate Similarity NPC470827
0.8239 Intermediate Similarity NPC4809
0.8235 Intermediate Similarity NPC317053
0.8235 Intermediate Similarity NPC155564
0.8235 Intermediate Similarity NPC102280
0.8235 Intermediate Similarity NPC248053
0.8235 Intermediate Similarity NPC324492
0.8205 Intermediate Similarity NPC259707
0.82 Intermediate Similarity NPC472091
0.82 Intermediate Similarity NPC472092
0.82 Intermediate Similarity NPC472090
0.82 Intermediate Similarity NPC221134
0.8194 Intermediate Similarity NPC47283
0.8194 Intermediate Similarity NPC39064
0.8194 Intermediate Similarity NPC53986
0.8194 Intermediate Similarity NPC38664
0.8188 Intermediate Similarity NPC474687
0.8187 Intermediate Similarity NPC86630
0.8187 Intermediate Similarity NPC471404
0.8187 Intermediate Similarity NPC159526
0.8187 Intermediate Similarity NPC470828
0.8187 Intermediate Similarity NPC205613
0.8187 Intermediate Similarity NPC106601
0.8187 Intermediate Similarity NPC212614
0.8187 Intermediate Similarity NPC151474
0.8182 Intermediate Similarity NPC471215
0.8182 Intermediate Similarity NPC262573
0.8169 Intermediate Similarity NPC97578
0.8163 Intermediate Similarity NPC77196
0.8163 Intermediate Similarity NPC85435
0.8158 Intermediate Similarity NPC184607
0.8156 Intermediate Similarity NPC120172
0.8153 Intermediate Similarity NPC469944
0.8153 Intermediate Similarity NPC134911
0.8153 Intermediate Similarity NPC44192
0.8153 Intermediate Similarity NPC272552
0.8153 Intermediate Similarity NPC322899
0.8153 Intermediate Similarity NPC226108
0.8153 Intermediate Similarity NPC46283
0.8151 Intermediate Similarity NPC211413

  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 NPC148516 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
0.8462 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD4908 Phase 1
0.8 Intermediate Similarity NPD2861 Phase 2
0.7958 Intermediate Similarity NPD1610 Phase 2
0.7891 Intermediate Similarity NPD4625 Phase 3
0.7676 Intermediate Similarity NPD1548 Phase 1
0.7669 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD6959 Discontinued
0.7651 Intermediate Similarity NPD7199 Phase 2
0.7628 Intermediate Similarity NPD3892 Phase 2
0.7616 Intermediate Similarity NPD1613 Approved
0.7616 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD5735 Approved
0.756 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6353 Approved
0.7515 Intermediate Similarity NPD7768 Phase 2
0.7483 Intermediate Similarity NPD4749 Approved
0.7483 Intermediate Similarity NPD5327 Phase 3
0.7467 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD7447 Phase 1
0.74 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7229 Phase 3
0.7394 Intermediate Similarity NPD7819 Suspended
0.7389 Intermediate Similarity NPD7037 Approved
0.7386 Intermediate Similarity NPD4060 Phase 1
0.7375 Intermediate Similarity NPD7213 Phase 3
0.7375 Intermediate Similarity NPD7212 Phase 2
0.7365 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7228 Approved
0.7325 Intermediate Similarity NPD5763 Approved
0.7325 Intermediate Similarity NPD5762 Approved
0.7321 Intermediate Similarity NPD6234 Discontinued
0.731 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD4967 Phase 2
0.7305 Intermediate Similarity NPD4965 Approved
0.7305 Intermediate Similarity NPD4966 Approved
0.7303 Intermediate Similarity NPD3027 Phase 3
0.7296 Intermediate Similarity NPD7466 Approved
0.729 Intermediate Similarity NPD2157 Approved
0.7289 Intermediate Similarity NPD8455 Phase 2
0.7273 Intermediate Similarity NPD4140 Approved
0.7267 Intermediate Similarity NPD7041 Phase 2
0.7267 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD37 Approved
0.7226 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD5124 Phase 1
0.72 Intermediate Similarity NPD6696 Suspended
0.7192 Intermediate Similarity NPD7741 Discontinued
0.7188 Intermediate Similarity NPD3750 Approved
0.7175 Intermediate Similarity NPD8313 Approved
0.7175 Intermediate Similarity NPD8312 Approved
0.7152 Intermediate Similarity NPD6100 Approved
0.7152 Intermediate Similarity NPD6099 Approved
0.7143 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD6674 Discontinued
0.7117 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD4624 Approved
0.7102 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD8651 Approved
0.7086 Intermediate Similarity NPD5844 Phase 1
0.7083 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD4097 Suspended
0.7066 Intermediate Similarity NPD7411 Suspended
0.7059 Intermediate Similarity NPD3749 Approved
0.7051 Intermediate Similarity NPD3620 Phase 2
0.7051 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD8053 Approved
0.7039 Intermediate Similarity NPD8054 Approved
0.7035 Intermediate Similarity NPD8127 Discontinued
0.7022 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6166 Phase 2
0.7011 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD4380 Phase 2
0.7 Intermediate Similarity NPD6002 Phase 3
0.7 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6005 Phase 3
0.7 Intermediate Similarity NPD6004 Phase 3
0.7 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.6993 Remote Similarity NPD6584 Phase 3
0.6975 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6971 Remote Similarity NPD7473 Discontinued
0.697 Remote Similarity NPD6273 Approved
0.6966 Remote Similarity NPD7240 Approved
0.6964 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6959 Remote Similarity NPD7831 Phase 2
0.6959 Remote Similarity NPD3091 Approved
0.6959 Remote Similarity NPD7075 Discontinued
0.6959 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6959 Remote Similarity NPD7833 Phase 2
0.6957 Remote Similarity NPD1549 Phase 2
0.6951 Remote Similarity NPD7390 Discontinued
0.6928 Remote Similarity NPD3094 Phase 2
0.6923 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7097 Phase 1
0.6918 Remote Similarity NPD7119 Phase 2
0.6909 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6906 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6355 Discontinued
0.6897 Remote Similarity NPD6232 Discontinued
0.6893 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6893 Remote Similarity NPD8156 Discontinued
0.6887 Remote Similarity NPD422 Phase 1
0.6887 Remote Similarity NPD3092 Approved
0.6879 Remote Similarity NPD8032 Phase 2
0.6879 Remote Similarity NPD5494 Approved
0.6875 Remote Similarity NPD3748 Approved
0.6875 Remote Similarity NPD5588 Approved
0.6872 Remote Similarity NPD6559 Discontinued
0.6871 Remote Similarity NPD7003 Approved
0.6871 Remote Similarity NPD6671 Approved
0.6845 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6839 Remote Similarity NPD5736 Approved
0.6839 Remote Similarity NPD3018 Phase 2
0.6836 Remote Similarity NPD8251 Approved
0.6836 Remote Similarity NPD8099 Discontinued
0.6836 Remote Similarity NPD8252 Approved
0.6824 Remote Similarity NPD1934 Approved
0.681 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6807 Remote Similarity NPD2532 Approved
0.6807 Remote Similarity NPD2534 Approved
0.6807 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6807 Remote Similarity NPD2533 Approved
0.68 Remote Similarity NPD3787 Discontinued
0.6797 Remote Similarity NPD6583 Phase 3
0.6797 Remote Similarity NPD6582 Phase 2
0.6793 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6784 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6781 Remote Similarity NPD7843 Approved
0.6772 Remote Similarity NPD6663 Approved
0.677 Remote Similarity NPD7033 Discontinued
0.677 Remote Similarity NPD1510 Phase 2
0.6763 Remote Similarity NPD4381 Clinical (unspecified phase)
0.676 Remote Similarity NPD7074 Phase 3
0.6757 Remote Similarity NPD7157 Approved
0.6755 Remote Similarity NPD3095 Discontinued
0.6755 Remote Similarity NPD4626 Approved
0.6748 Remote Similarity NPD970 Clinical (unspecified phase)
0.6742 Remote Similarity NPD3818 Discontinued
0.6742 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6739 Remote Similarity NPD7906 Approved
0.673 Remote Similarity NPD2238 Phase 2
0.6728 Remote Similarity NPD2796 Approved
0.6726 Remote Similarity NPD7427 Discontinued
0.6719 Remote Similarity NPD7680 Approved
0.6711 Remote Similarity NPD7340 Approved
0.6709 Remote Similarity NPD6798 Discontinued
0.6708 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6708 Remote Similarity NPD4536 Approved
0.6708 Remote Similarity NPD4538 Approved
0.6707 Remote Similarity NPD7019 Approved
0.6707 Remote Similarity NPD7020 Approved
0.6705 Remote Similarity NPD7773 Phase 2
0.6705 Remote Similarity NPD3882 Suspended
0.6704 Remote Similarity NPD7054 Approved
0.669 Remote Similarity NPD4750 Phase 3
0.6689 Remote Similarity NPD5691 Approved
0.6688 Remote Similarity NPD2983 Phase 2
0.6688 Remote Similarity NPD2982 Phase 2
0.6687 Remote Similarity NPD5058 Phase 3
0.6687 Remote Similarity NPD6666 Approved
0.6687 Remote Similarity NPD6667 Approved
0.6686 Remote Similarity NPD1653 Approved
0.6667 Remote Similarity NPD1091 Approved
0.6667 Remote Similarity NPD2342 Discontinued
0.6667 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6331 Phase 2
0.6667 Remote Similarity NPD7472 Approved
0.6667 Remote Similarity NPD4108 Discontinued
0.6667 Remote Similarity NPD5960 Phase 3
0.6648 Remote Similarity NPD7808 Phase 3
0.6648 Remote Similarity NPD7549 Discontinued
0.6647 Remote Similarity NPD1511 Approved
0.6646 Remote Similarity NPD7095 Approved
0.6645 Remote Similarity NPD5846 Approved
0.6645 Remote Similarity NPD6516 Phase 2
0.6645 Remote Similarity NPD4059 Approved
0.6631 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6628 Remote Similarity NPD6801 Discontinued
0.6626 Remote Similarity NPD5406 Approved
0.6626 Remote Similarity NPD5408 Approved
0.6626 Remote Similarity NPD4476 Approved
0.6626 Remote Similarity NPD5405 Approved
0.6626 Remote Similarity NPD4477 Approved
0.6626 Remote Similarity NPD5404 Approved
0.6624 Remote Similarity NPD1712 Approved
0.6623 Remote Similarity NPD1840 Phase 2
0.6623 Remote Similarity NPD2981 Phase 2
0.6622 Remote Similarity NPD5283 Phase 1
0.6612 Remote Similarity NPD7312 Approved
0.6612 Remote Similarity NPD7310 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