Structure

Physi-Chem Properties

Molecular Weight:  426.39
Volume:  490.807
LogP:  6.991
LogD:  5.866
LogS:  -6.327
# Rotatable Bonds:  1
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.421
Synthetic Accessibility Score:  4.663
Fsp3:  0.933
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -5.104
MDCK Permeability:  1.4101716260483954e-05
Pgp-inhibitor:  0.023
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.774
30% Bioavailability (F30%):  0.835

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.05
Plasma Protein Binding (PPB):  95.49597930908203%
Volume Distribution (VD):  1.24
Pgp-substrate:  1.7105093002319336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.043
CYP1A2-substrate:  0.563
CYP2C19-inhibitor:  0.079
CYP2C19-substrate:  0.949
CYP2C9-inhibitor:  0.125
CYP2C9-substrate:  0.489
CYP2D6-inhibitor:  0.062
CYP2D6-substrate:  0.888
CYP3A4-inhibitor:  0.345
CYP3A4-substrate:  0.469

ADMET: Excretion

Clearance (CL):  4.824
Half-life (T1/2):  0.125

ADMET: Toxicity

hERG Blockers:  0.137
Human Hepatotoxicity (H-HT):  0.083
Drug-inuced Liver Injury (DILI):  0.014
AMES Toxicity:  0.001
Rat Oral Acute Toxicity:  0.187
Maximum Recommended Daily Dose:  0.96
Skin Sensitization:  0.777
Carcinogencity:  0.012
Eye Corrosion:  0.995
Eye Irritation:  0.91
Respiratory Toxicity:  0.474

Download Data

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

  Natural Product: NPC62657

Natural Product ID:  NPC62657
Common Name*:   (1R,3Ar,5Ar,5Br,7As,9S,11Ar,11Br,13Ar,13Br)-3A,5A,5B,8,8,11A-Hexamethyl-1-Prop-1-En-2-Yl-1,2,3,4,5,6,7,7A,9,10,11,11B,12,13,13A,13B-Hexadecahydrocyclopenta[A]Chrysen-9-Ol
IUPAC Name:   (1R,3aR,5aR,5bR,7aS,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Synonyms:  
Standard InCHIKey:  MQYXUWHLBZFQQO-HEQGEZKBSA-N
Standard InCHI:  InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22+,23+,24-,25+,27+,28-,29+,30+/m0/s1
SMILES:  CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3348959
PubChem CID:   7092625
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO16699 Agave utahensis Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[19645463]
NPO3049 Rhinacanthus nasutus Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[8463799]
NPO3049 Rhinacanthus nasutus Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[8792629]
NPO3049 Rhinacanthus nasutus Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[9214738]
NPO27015 Valeriana hardwickii Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10884 Glycyrrhiza squamulosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16775 Thermopsis lanceolata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3049 Rhinacanthus nasutus Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10884 Glycyrrhiza squamulosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27015 Valeriana hardwickii Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16775 Thermopsis lanceolata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10884 Glycyrrhiza squamulosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16775 Thermopsis lanceolata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27015 Valeriana hardwickii Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8606 Mallotus repandus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3049 Rhinacanthus nasutus Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12707 Lithospermum canescens Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11678 Aeonium cuneatum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12218 Pulicaria wightiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27537 Litsea hayatae Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27329 Sedum stoloniferum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3166 Arenaria oreophila Species Scolopacidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4754 Yucca flexilis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27270 Buchholzia coriacea Species Capparaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO642 Artemisia bigelovii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1535 Solanum americanum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15300 Bipolaris zeicola Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16699 Agave utahensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27023 Flemingia stricta Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13891 Scolytus multistriatus Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16775 Thermopsis lanceolata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27006 Nepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11855 Streptomyces xanthocidicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11429 Matricaria parthenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14480 Tornabea scutellifera Species Physciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14435 Mnium hornum Species Mniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12738 Ajuga australis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11633 Kelletia kelletii Species Buccinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7720 Cyathocline purpurea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10884 Glycyrrhiza squamulosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12393 Xanthoparmelia subincerta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1774 Camassia leichtlinii Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16207 Acacia glaucescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16102 Senecio chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15984 Blainvillea rhomboidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13047 Epipolasis kushimotoensis Species Axinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13938 Plantago alpina Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13400 Elaeagnus pungens Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11453 Centaurea cadmea 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 14950.2 nM PMID[465280]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 66.8 nM PMID[465280]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 5304.5 nM PMID[465280]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 8407.1 nM PMID[465280]

☑ 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 NPC62657 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 NPC25511
1.0 High Similarity NPC192638
0.9855 High Similarity NPC104387
0.9855 High Similarity NPC240235
0.9855 High Similarity NPC178383
0.9855 High Similarity NPC231256
0.9855 High Similarity NPC212879
0.9714 High Similarity NPC78067
0.9714 High Similarity NPC278091
0.9714 High Similarity NPC86305
0.9714 High Similarity NPC14112
0.9714 High Similarity NPC93662
0.9706 High Similarity NPC111234
0.9577 High Similarity NPC248830
0.9577 High Similarity NPC212241
0.9577 High Similarity NPC119355
0.9577 High Similarity NPC202540
0.9559 High Similarity NPC45296
0.9444 High Similarity NPC42853
0.9444 High Similarity NPC102708
0.9429 High Similarity NPC49168
0.9429 High Similarity NPC254509
0.9429 High Similarity NPC5046
0.9429 High Similarity NPC196358
0.9429 High Similarity NPC145552
0.9315 High Similarity NPC80297
0.9315 High Similarity NPC116119
0.9315 High Similarity NPC472742
0.9315 High Similarity NPC49599
0.9315 High Similarity NPC49627
0.9315 High Similarity NPC475727
0.9296 High Similarity NPC3403
0.9296 High Similarity NPC200243
0.9296 High Similarity NPC185536
0.9296 High Similarity NPC70982
0.9296 High Similarity NPC230704
0.9286 High Similarity NPC195489
0.9189 High Similarity NPC475679
0.9167 High Similarity NPC237460
0.9167 High Similarity NPC91573
0.9155 High Similarity NPC472503
0.9155 High Similarity NPC308440
0.9143 High Similarity NPC301226
0.9041 High Similarity NPC331618
0.9041 High Similarity NPC257191
0.9014 High Similarity NPC211009
0.8919 High Similarity NPC85346
0.8919 High Similarity NPC285761
0.8919 High Similarity NPC477819
0.8919 High Similarity NPC301707
0.8919 High Similarity NPC167037
0.8919 High Similarity NPC244385
0.8919 High Similarity NPC472342
0.8919 High Similarity NPC31828
0.8919 High Similarity NPC302041
0.8919 High Similarity NPC65897
0.8919 High Similarity NPC138621
0.8919 High Similarity NPC6978
0.8919 High Similarity NPC477817
0.8904 High Similarity NPC189883
0.8831 High Similarity NPC5280
0.8831 High Similarity NPC246956
0.8831 High Similarity NPC475726
0.8831 High Similarity NPC472743
0.8824 High Similarity NPC476737
0.8824 High Similarity NPC27243
0.88 High Similarity NPC80530
0.88 High Similarity NPC273410
0.8784 High Similarity NPC260301
0.8784 High Similarity NPC307336
0.8784 High Similarity NPC138502
0.8767 High Similarity NPC257347
0.8767 High Similarity NPC121744
0.8767 High Similarity NPC322353
0.8767 High Similarity NPC103822
0.8767 High Similarity NPC471723
0.8767 High Similarity NPC141071
0.8767 High Similarity NPC144075
0.8767 High Similarity NPC118508
0.8718 High Similarity NPC475745
0.8718 High Similarity NPC474482
0.8718 High Similarity NPC264665
0.8718 High Similarity NPC74595
0.8696 High Similarity NPC142712
0.8684 High Similarity NPC102253
0.8684 High Similarity NPC13554
0.8684 High Similarity NPC322313
0.8684 High Similarity NPC78545
0.8684 High Similarity NPC71535
0.8684 High Similarity NPC236237
0.8667 High Similarity NPC472499
0.8667 High Similarity NPC472500
0.8667 High Similarity NPC312328
0.8667 High Similarity NPC472501
0.8649 High Similarity NPC122418
0.8649 High Similarity NPC134330
0.8649 High Similarity NPC38141
0.8649 High Similarity NPC46160
0.8649 High Similarity NPC120098
0.8649 High Similarity NPC129165
0.8649 High Similarity NPC290598
0.8649 High Similarity NPC30590
0.8649 High Similarity NPC202642
0.8649 High Similarity NPC300324
0.8649 High Similarity NPC73875
0.8649 High Similarity NPC27765
0.8649 High Similarity NPC240604
0.8649 High Similarity NPC265328
0.863 High Similarity NPC476736
0.863 High Similarity NPC100334
0.8611 High Similarity NPC164045
0.8608 High Similarity NPC264317
0.8608 High Similarity NPC294438
0.8608 High Similarity NPC292553
0.859 High Similarity NPC470929
0.8571 High Similarity NPC48079
0.8553 High Similarity NPC1319
0.8553 High Similarity NPC24504
0.8553 High Similarity NPC476316
0.8533 High Similarity NPC157996
0.8533 High Similarity NPC214570
0.8533 High Similarity NPC101475
0.8533 High Similarity NPC34177
0.8533 High Similarity NPC40394
0.8514 High Similarity NPC136188
0.8514 High Similarity NPC22105
0.8514 High Similarity NPC230301
0.8514 High Similarity NPC285893
0.8514 High Similarity NPC162742
0.8514 High Similarity NPC134847
0.8514 High Similarity NPC288035
0.8514 High Similarity NPC138374
0.8514 High Similarity NPC304309
0.8514 High Similarity NPC28657
0.8514 High Similarity NPC34700
0.85 High Similarity NPC12774
0.85 High Similarity NPC472738
0.85 High Similarity NPC168231
0.85 High Similarity NPC2783
0.85 High Similarity NPC98236
0.85 High Similarity NPC269396
0.8493 Intermediate Similarity NPC201373
0.8493 Intermediate Similarity NPC472506
0.8481 Intermediate Similarity NPC474233
0.8481 Intermediate Similarity NPC209802
0.8462 Intermediate Similarity NPC248886
0.8462 Intermediate Similarity NPC477599
0.8462 Intermediate Similarity NPC296701
0.8462 Intermediate Similarity NPC218616
0.8451 Intermediate Similarity NPC472741
0.8442 Intermediate Similarity NPC47149
0.8442 Intermediate Similarity NPC236112
0.8442 Intermediate Similarity NPC206735
0.8421 Intermediate Similarity NPC186191
0.8421 Intermediate Similarity NPC300499
0.8421 Intermediate Similarity NPC472502
0.8421 Intermediate Similarity NPC475
0.8421 Intermediate Similarity NPC275910
0.8421 Intermediate Similarity NPC22955
0.8421 Intermediate Similarity NPC205455
0.8421 Intermediate Similarity NPC196753
0.8421 Intermediate Similarity NPC99168
0.8421 Intermediate Similarity NPC253807
0.8421 Intermediate Similarity NPC470396
0.8421 Intermediate Similarity NPC98386
0.8421 Intermediate Similarity NPC158662
0.8421 Intermediate Similarity NPC474989
0.8421 Intermediate Similarity NPC230295
0.84 Intermediate Similarity NPC113733
0.84 Intermediate Similarity NPC470362
0.84 Intermediate Similarity NPC321016
0.84 Intermediate Similarity NPC107059
0.84 Intermediate Similarity NPC321381
0.84 Intermediate Similarity NPC106364
0.8395 Intermediate Similarity NPC264005
0.8395 Intermediate Similarity NPC33768
0.8395 Intermediate Similarity NPC4643
0.8395 Intermediate Similarity NPC269360
0.8395 Intermediate Similarity NPC57469
0.8382 Intermediate Similarity NPC71460
0.8382 Intermediate Similarity NPC148174
0.8382 Intermediate Similarity NPC218585
0.8378 Intermediate Similarity NPC469534
0.8378 Intermediate Similarity NPC469533
0.8378 Intermediate Similarity NPC469593
0.8354 Intermediate Similarity NPC110778
0.8354 Intermediate Similarity NPC207013
0.8354 Intermediate Similarity NPC113978
0.8354 Intermediate Similarity NPC232023
0.8354 Intermediate Similarity NPC85095
0.8354 Intermediate Similarity NPC211135
0.8354 Intermediate Similarity NPC477818
0.8354 Intermediate Similarity NPC216420
0.8333 Intermediate Similarity NPC129829
0.8333 Intermediate Similarity NPC210323
0.8333 Intermediate Similarity NPC157655
0.8333 Intermediate Similarity NPC474531
0.8333 Intermediate Similarity NPC254037
0.8312 Intermediate Similarity NPC201459
0.8312 Intermediate Similarity NPC30986

  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 NPC62657 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
0.8684 High Similarity NPD7525 Registered
0.8608 High Similarity NPD7520 Clinical (unspecified phase)
0.8514 High Similarity NPD7339 Approved
0.8514 High Similarity NPD6942 Approved
0.8312 Intermediate Similarity NPD7645 Phase 2
0.7922 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD8034 Phase 2
0.7791 Intermediate Similarity NPD8035 Phase 2
0.7662 Intermediate Similarity NPD6924 Approved
0.7662 Intermediate Similarity NPD6926 Approved
0.7632 Intermediate Similarity NPD7151 Approved
0.7632 Intermediate Similarity NPD7152 Approved
0.7632 Intermediate Similarity NPD7150 Approved
0.7632 Intermediate Similarity NPD4243 Approved
0.76 Intermediate Similarity NPD6922 Approved
0.76 Intermediate Similarity NPD6923 Approved
0.759 Intermediate Similarity NPD4786 Approved
0.7558 Intermediate Similarity NPD5328 Approved
0.75 Intermediate Similarity NPD4787 Phase 1
0.75 Intermediate Similarity NPD7144 Approved
0.75 Intermediate Similarity NPD7143 Approved
0.747 Intermediate Similarity NPD4788 Approved
0.7468 Intermediate Similarity NPD6933 Approved
0.7436 Intermediate Similarity NPD4785 Approved
0.7436 Intermediate Similarity NPD4784 Approved
0.7412 Intermediate Similarity NPD3618 Phase 1
0.7403 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6079 Approved
0.7349 Intermediate Similarity NPD3667 Approved
0.7317 Intermediate Similarity NPD4748 Discontinued
0.725 Intermediate Similarity NPD6117 Approved
0.7215 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD6929 Approved
0.7191 Intermediate Similarity NPD7515 Phase 2
0.716 Intermediate Similarity NPD6116 Phase 1
0.7143 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD4190 Phase 3
0.7125 Intermediate Similarity NPD5275 Approved
0.7111 Intermediate Similarity NPD4202 Approved
0.7108 Intermediate Similarity NPD6930 Phase 2
0.7108 Intermediate Similarity NPD6931 Approved
0.7108 Intermediate Similarity NPD7509 Discontinued
0.7073 Intermediate Similarity NPD6118 Approved
0.7073 Intermediate Similarity NPD6697 Approved
0.7073 Intermediate Similarity NPD6114 Approved
0.7073 Intermediate Similarity NPD6115 Approved
0.6977 Remote Similarity NPD3665 Phase 1
0.6977 Remote Similarity NPD3666 Approved
0.6977 Remote Similarity NPD3133 Approved
0.6951 Remote Similarity NPD6925 Approved
0.6951 Remote Similarity NPD6932 Approved
0.6951 Remote Similarity NPD5776 Phase 2
0.6915 Remote Similarity NPD7638 Approved
0.6914 Remote Similarity NPD3703 Phase 2
0.6905 Remote Similarity NPD6928 Phase 2
0.6882 Remote Similarity NPD4697 Phase 3
0.6882 Remote Similarity NPD5222 Approved
0.6882 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5221 Approved
0.6867 Remote Similarity NPD7145 Approved
0.686 Remote Similarity NPD6695 Phase 3
0.6848 Remote Similarity NPD7748 Approved
0.6842 Remote Similarity NPD7640 Approved
0.6842 Remote Similarity NPD7639 Approved
0.6835 Remote Similarity NPD4245 Approved
0.6835 Remote Similarity NPD4244 Approved
0.6835 Remote Similarity NPD4789 Approved
0.6809 Remote Similarity NPD4755 Approved
0.6809 Remote Similarity NPD5173 Approved
0.6795 Remote Similarity NPD5360 Phase 3
0.6795 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4195 Approved
0.6786 Remote Similarity NPD6683 Phase 2
0.6782 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6739 Remote Similarity NPD6399 Phase 3
0.6709 Remote Similarity NPD3698 Phase 2
0.6706 Remote Similarity NPD7514 Phase 3
0.6705 Remote Similarity NPD6893 Approved
0.6667 Remote Similarity NPD4700 Approved
0.6667 Remote Similarity NPD4696 Approved
0.6667 Remote Similarity NPD5285 Approved
0.6667 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5286 Approved
0.6632 Remote Similarity NPD7902 Approved
0.6629 Remote Similarity NPD5279 Phase 3
0.6628 Remote Similarity NPD6902 Approved
0.6623 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5223 Approved
0.6593 Remote Similarity NPD4753 Phase 2
0.6591 Remote Similarity NPD3668 Phase 3
0.6562 Remote Similarity NPD5290 Discontinued
0.6556 Remote Similarity NPD7524 Approved
0.6556 Remote Similarity NPD7750 Discontinued
0.6552 Remote Similarity NPD4221 Approved
0.6552 Remote Similarity NPD4223 Phase 3
0.6531 Remote Similarity NPD5224 Approved
0.6531 Remote Similarity NPD5226 Approved
0.6531 Remote Similarity NPD5225 Approved
0.6531 Remote Similarity NPD4633 Approved
0.6531 Remote Similarity NPD5211 Phase 2
0.6517 Remote Similarity NPD5329 Approved
0.6512 Remote Similarity NPD7332 Phase 2
0.6506 Remote Similarity NPD8264 Approved
0.65 Remote Similarity NPD5739 Approved
0.65 Remote Similarity NPD6402 Approved
0.65 Remote Similarity NPD7128 Approved
0.65 Remote Similarity NPD6675 Approved
0.6484 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6471 Remote Similarity NPD3671 Phase 1
0.6465 Remote Similarity NPD5175 Approved
0.6465 Remote Similarity NPD4754 Approved
0.6465 Remote Similarity NPD5174 Approved
0.6437 Remote Similarity NPD6898 Phase 1
0.6404 Remote Similarity NPD4197 Approved
0.64 Remote Similarity NPD5141 Approved
0.6375 Remote Similarity NPD6705 Phase 1
0.6373 Remote Similarity NPD6899 Approved
0.6373 Remote Similarity NPD7320 Approved
0.6373 Remote Similarity NPD6881 Approved
0.6364 Remote Similarity NPD7632 Discontinued
0.6341 Remote Similarity NPD4758 Discontinued
0.6337 Remote Similarity NPD4768 Approved
0.6337 Remote Similarity NPD4767 Approved
0.6324 Remote Similarity NPD385 Approved
0.6324 Remote Similarity NPD384 Approved
0.6316 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7900 Approved
0.6311 Remote Similarity NPD6372 Approved
0.6311 Remote Similarity NPD6373 Approved
0.6289 Remote Similarity NPD6084 Phase 2
0.6289 Remote Similarity NPD6083 Phase 2
0.6279 Remote Similarity NPD3617 Approved
0.6277 Remote Similarity NPD7087 Discontinued
0.6275 Remote Similarity NPD5701 Approved
0.6275 Remote Similarity NPD5697 Approved
0.6264 Remote Similarity NPD4690 Approved
0.6264 Remote Similarity NPD7146 Approved
0.6264 Remote Similarity NPD4138 Approved
0.6264 Remote Similarity NPD5330 Approved
0.6264 Remote Similarity NPD7521 Approved
0.6264 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6264 Remote Similarity NPD4693 Phase 3
0.6264 Remote Similarity NPD7334 Approved
0.6264 Remote Similarity NPD6684 Approved
0.6264 Remote Similarity NPD4689 Approved
0.6264 Remote Similarity NPD6409 Approved
0.6264 Remote Similarity NPD4688 Approved
0.6264 Remote Similarity NPD5205 Approved
0.625 Remote Similarity NPD7102 Approved
0.625 Remote Similarity NPD5210 Approved
0.625 Remote Similarity NPD7290 Approved
0.625 Remote Similarity NPD6883 Approved
0.625 Remote Similarity NPD4629 Approved
0.6237 Remote Similarity NPD6051 Approved
0.6214 Remote Similarity NPD5168 Approved
0.6214 Remote Similarity NPD4730 Approved
0.6214 Remote Similarity NPD6011 Approved
0.6214 Remote Similarity NPD4729 Approved
0.6214 Remote Similarity NPD5128 Approved
0.619 Remote Similarity NPD6617 Approved
0.619 Remote Similarity NPD6650 Approved
0.619 Remote Similarity NPD6847 Approved
0.619 Remote Similarity NPD8130 Phase 1
0.619 Remote Similarity NPD6869 Approved
0.619 Remote Similarity NPD6401 Clinical (unspecified phase)
0.619 Remote Similarity NPD6649 Approved
0.617 Remote Similarity NPD6701 Clinical (unspecified phase)
0.617 Remote Similarity NPD6700 Approved
0.6154 Remote Similarity NPD6012 Approved
0.6154 Remote Similarity NPD6013 Approved
0.6154 Remote Similarity NPD6014 Approved
0.6147 Remote Similarity NPD7328 Approved
0.6147 Remote Similarity NPD7327 Approved
0.6145 Remote Similarity NPD6081 Approved
0.6132 Remote Similarity NPD8297 Approved
0.6132 Remote Similarity NPD6882 Approved
0.6129 Remote Similarity NPD6903 Approved
0.6129 Remote Similarity NPD4722 Approved
0.6129 Remote Similarity NPD4723 Approved
0.6129 Remote Similarity NPD6672 Approved
0.6129 Remote Similarity NPD5737 Approved
0.6125 Remote Similarity NPD4224 Phase 2
0.6105 Remote Similarity NPD6703 Approved
0.6105 Remote Similarity NPD6702 Approved
0.61 Remote Similarity NPD4159 Approved
0.6095 Remote Similarity NPD4634 Approved
0.6095 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6095 Remote Similarity NPD5251 Approved
0.6095 Remote Similarity NPD5248 Approved
0.6095 Remote Similarity NPD5135 Approved
0.6095 Remote Similarity NPD5249 Phase 3
0.6095 Remote Similarity NPD5169 Approved
0.6095 Remote Similarity NPD5247 Approved
0.6095 Remote Similarity NPD5250 Approved
0.6092 Remote Similarity NPD5364 Discontinued
0.6091 Remote Similarity NPD7516 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