Structure

Physi-Chem Properties

Molecular Weight:  365.96
Volume:  260.488
LogP:  1.338
LogD:  0.258
LogS:  -2.159
# Rotatable Bonds:  6
TPSA:  81.5
# H-Bond Aceptor:  4
# H-Bond Donor:  5
# Rings:  1
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.671
Synthetic Accessibility Score:  2.967
Fsp3:  0.455
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.671
MDCK Permeability:  0.0016274790978059173
Pgp-inhibitor:  0.001
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.216
Plasma Protein Binding (PPB):  43.860069274902344%
Volume Distribution (VD):  1.049
Pgp-substrate:  47.868507385253906%

ADMET: Metabolism

CYP1A2-inhibitor:  0.943
CYP1A2-substrate:  0.514
CYP2C19-inhibitor:  0.062
CYP2C19-substrate:  0.506
CYP2C9-inhibitor:  0.019
CYP2C9-substrate:  0.502
CYP2D6-inhibitor:  0.66
CYP2D6-substrate:  0.883
CYP3A4-inhibitor:  0.113
CYP3A4-substrate:  0.255

ADMET: Excretion

Clearance (CL):  1.541
Half-life (T1/2):  0.564

ADMET: Toxicity

hERG Blockers:  0.251
Human Hepatotoxicity (H-HT):  0.232
Drug-inuced Liver Injury (DILI):  0.036
AMES Toxicity:  0.063
Rat Oral Acute Toxicity:  0.669
Maximum Recommended Daily Dose:  0.93
Skin Sensitization:  0.651
Carcinogencity:  0.087
Eye Corrosion:  0.087
Eye Irritation:  0.013
Respiratory Toxicity:  0.87

Download Data

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

  Natural Product: NPC474673

Natural Product ID:  NPC474673
Common Name*:   Hydroxymoloka'iamine
IUPAC Name:   2-amino-1-[4-(3-aminopropoxy)-3,5-dibromophenyl]ethanol
Synonyms:   Hydroxymoloka'Iamine
Standard InCHIKey:  LDAZBBKQQALEAP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H16Br2N2O2/c12-8-4-7(10(16)6-15)5-9(13)11(8)17-3-1-2-14/h4-5,10,16H,1-3,6,14-15H2
SMILES:  NCCCOc1c(Br)cc(cc1Br)C(CN)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479055
PubChem CID:   25016152
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002341] Phenol ethers

*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
NPO32567 suberea sp. Species Aplysinellidae Eukaryota n.a. n.a. n.a. PMID[11473442]
NPO733 Pseudoceratina arabica Species Pseudoceratinidae Eukaryota n.a. Red Sea n.a. PMID[18598078]
NPO32567 suberea sp. Species Aplysinellidae Eukaryota n.a. n.a. n.a. PMID[23964644]
NPO733 Pseudoceratina arabica Species Pseudoceratinidae 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
NPT370 Cell Line NCI-H23 Homo sapiens GI50 > 70000.0 nM PMID[559443]
NPT2477 Cell Line NUGC-3 Homo sapiens GI50 > 70000.0 nM PMID[559443]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 > 70000.0 nM PMID[559443]
NPT369 Cell Line ACHN Homo sapiens GI50 > 70000.0 nM PMID[559443]
NPT306 Cell Line PC-3 Homo sapiens GI50 > 70000.0 nM PMID[559443]
NPT148 Cell Line HCT-15 Homo sapiens GI50 > 70000.0 nM PMID[559443]

☑ 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 NPC474673 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
0.907 High Similarity NPC272463
0.9014 High Similarity NPC469711
0.8521 High Similarity NPC78530
0.8433 Intermediate Similarity NPC110131
0.8367 Intermediate Similarity NPC47672
0.8239 Intermediate Similarity NPC128877
0.8231 Intermediate Similarity NPC76412
0.82 Intermediate Similarity NPC233926
0.8194 Intermediate Similarity NPC308571
0.8079 Intermediate Similarity NPC156311
0.8077 Intermediate Similarity NPC115803
0.8014 Intermediate Similarity NPC135349
0.7902 Intermediate Similarity NPC470471
0.7815 Intermediate Similarity NPC258222
0.7793 Intermediate Similarity NPC470470
0.7727 Intermediate Similarity NPC59387
0.7582 Intermediate Similarity NPC109968
0.7544 Intermediate Similarity NPC474678
0.7544 Intermediate Similarity NPC471338
0.7533 Intermediate Similarity NPC470472
0.7517 Intermediate Similarity NPC474128
0.75 Intermediate Similarity NPC296085
0.75 Intermediate Similarity NPC475843
0.75 Intermediate Similarity NPC71629
0.7483 Intermediate Similarity NPC470248
0.7483 Intermediate Similarity NPC470249
0.7463 Intermediate Similarity NPC26524
0.7424 Intermediate Similarity NPC290566
0.7424 Intermediate Similarity NPC145638
0.7324 Intermediate Similarity NPC95733
0.7324 Intermediate Similarity NPC62101
0.731 Intermediate Similarity NPC135173
0.7305 Intermediate Similarity NPC116562
0.7297 Intermediate Similarity NPC235633
0.7294 Intermediate Similarity NPC77435
0.7294 Intermediate Similarity NPC259071
0.7288 Intermediate Similarity NPC471337
0.7273 Intermediate Similarity NPC29477
0.7273 Intermediate Similarity NPC320242
0.726 Intermediate Similarity NPC326599
0.726 Intermediate Similarity NPC329595
0.726 Intermediate Similarity NPC473724
0.7252 Intermediate Similarity NPC8302
0.7251 Intermediate Similarity NPC475658
0.7251 Intermediate Similarity NPC473892
0.7211 Intermediate Similarity NPC307123
0.7211 Intermediate Similarity NPC97870
0.7211 Intermediate Similarity NPC247018
0.7209 Intermediate Similarity NPC473409
0.7209 Intermediate Similarity NPC141405
0.7209 Intermediate Similarity NPC82741
0.72 Intermediate Similarity NPC213471
0.7193 Intermediate Similarity NPC8093
0.7193 Intermediate Similarity NPC121571
0.7163 Intermediate Similarity NPC318357
0.7152 Intermediate Similarity NPC477255
0.7151 Intermediate Similarity NPC471591
0.7143 Intermediate Similarity NPC11449
0.7143 Intermediate Similarity NPC227953
0.7133 Intermediate Similarity NPC211218
0.7121 Intermediate Similarity NPC42383
0.7101 Intermediate Similarity NPC213
0.7101 Intermediate Similarity NPC10286
0.7093 Intermediate Similarity NPC49172
0.709 Intermediate Similarity NPC97811
0.7075 Intermediate Similarity NPC474087
0.7045 Intermediate Similarity NPC38079
0.7045 Intermediate Similarity NPC108875
0.7044 Intermediate Similarity NPC73132
0.7044 Intermediate Similarity NPC471235
0.7044 Intermediate Similarity NPC235033
0.7039 Intermediate Similarity NPC470250
0.7039 Intermediate Similarity NPC40321
0.7037 Intermediate Similarity NPC54543
0.7034 Intermediate Similarity NPC141739
0.7034 Intermediate Similarity NPC136112
0.7029 Intermediate Similarity NPC235250
0.7027 Intermediate Similarity NPC475735
0.7015 Intermediate Similarity NPC251306
0.7014 Intermediate Similarity NPC473572
0.7014 Intermediate Similarity NPC474169
0.7014 Intermediate Similarity NPC328267
0.7011 Intermediate Similarity NPC471336
0.7011 Intermediate Similarity NPC470746
0.7006 Intermediate Similarity NPC469721
0.7006 Intermediate Similarity NPC202866
0.7 Intermediate Similarity NPC303993
0.6992 Remote Similarity NPC470393
0.6985 Remote Similarity NPC473358
0.698 Remote Similarity NPC158078
0.6977 Remote Similarity NPC477254
0.6972 Remote Similarity NPC263835
0.6972 Remote Similarity NPC180207
0.697 Remote Similarity NPC305205
0.6959 Remote Similarity NPC474091
0.6957 Remote Similarity NPC301735
0.6944 Remote Similarity NPC229213
0.6939 Remote Similarity NPC78061
0.6939 Remote Similarity NPC159987
0.6939 Remote Similarity NPC122359
0.6939 Remote Similarity NPC474147
0.6939 Remote Similarity NPC473708
0.6897 Remote Similarity NPC13020
0.6897 Remote Similarity NPC105999
0.6897 Remote Similarity NPC140359
0.6894 Remote Similarity NPC51633
0.6889 Remote Similarity NPC186469
0.6883 Remote Similarity NPC470709
0.6871 Remote Similarity NPC43706
0.6857 Remote Similarity NPC174607
0.6853 Remote Similarity NPC115627
0.6853 Remote Similarity NPC169207
0.6853 Remote Similarity NPC118522
0.6849 Remote Similarity NPC213414
0.6849 Remote Similarity NPC236265
0.6849 Remote Similarity NPC105513
0.6842 Remote Similarity NPC192596
0.6839 Remote Similarity NPC204546
0.6838 Remote Similarity NPC471495
0.6835 Remote Similarity NPC471488
0.6833 Remote Similarity NPC469731
0.6818 Remote Similarity NPC147847
0.68 Remote Similarity NPC226493
0.68 Remote Similarity NPC160081
0.6786 Remote Similarity NPC161696
0.6784 Remote Similarity NPC469979
0.6784 Remote Similarity NPC226001
0.6783 Remote Similarity NPC43275
0.677 Remote Similarity NPC152947
0.6763 Remote Similarity NPC115379
0.6761 Remote Similarity NPC120075
0.6754 Remote Similarity NPC471335
0.6753 Remote Similarity NPC197045
0.6744 Remote Similarity NPC110454
0.6744 Remote Similarity NPC126128
0.6744 Remote Similarity NPC298981
0.6744 Remote Similarity NPC207819
0.6744 Remote Similarity NPC473462
0.6742 Remote Similarity NPC125732
0.6742 Remote Similarity NPC100870
0.6739 Remote Similarity NPC46844
0.6736 Remote Similarity NPC321133
0.6733 Remote Similarity NPC85049
0.6733 Remote Similarity NPC99280
0.6721 Remote Similarity NPC123140
0.6712 Remote Similarity NPC296202
0.6711 Remote Similarity NPC291847
0.6692 Remote Similarity NPC20142
0.6692 Remote Similarity NPC215351
0.6691 Remote Similarity NPC21890
0.669 Remote Similarity NPC471486
0.669 Remote Similarity NPC269242
0.6687 Remote Similarity NPC277857
0.6687 Remote Similarity NPC115144
0.6667 Remote Similarity NPC313414
0.6667 Remote Similarity NPC17760
0.6667 Remote Similarity NPC475396
0.6648 Remote Similarity NPC248822
0.6646 Remote Similarity NPC79076
0.6646 Remote Similarity NPC178466
0.6646 Remote Similarity NPC63628
0.6645 Remote Similarity NPC474753
0.6645 Remote Similarity NPC204848
0.6645 Remote Similarity NPC470392
0.6645 Remote Similarity NPC14600
0.6645 Remote Similarity NPC312770
0.6645 Remote Similarity NPC160607
0.6645 Remote Similarity NPC41473
0.6644 Remote Similarity NPC7830
0.6643 Remote Similarity NPC142042
0.6629 Remote Similarity NPC214188
0.6629 Remote Similarity NPC74618
0.6629 Remote Similarity NPC301941
0.6628 Remote Similarity NPC225130
0.6623 Remote Similarity NPC478071
0.6623 Remote Similarity NPC262641
0.6623 Remote Similarity NPC245386
0.6622 Remote Similarity NPC109822
0.6622 Remote Similarity NPC137117
0.6622 Remote Similarity NPC94276
0.6621 Remote Similarity NPC93398
0.6621 Remote Similarity NPC60589
0.6621 Remote Similarity NPC258979
0.6621 Remote Similarity NPC8283
0.6621 Remote Similarity NPC469708
0.6619 Remote Similarity NPC88868
0.6619 Remote Similarity NPC231251
0.6619 Remote Similarity NPC25067
0.6611 Remote Similarity NPC64066
0.6603 Remote Similarity NPC197239
0.6603 Remote Similarity NPC259800
0.6603 Remote Similarity NPC241086
0.6603 Remote Similarity NPC318984
0.6603 Remote Similarity NPC326860
0.6603 Remote Similarity NPC271942
0.6603 Remote Similarity NPC328137
0.6603 Remote Similarity NPC318028
0.6603 Remote Similarity NPC317741
0.6603 Remote Similarity NPC282087
0.6603 Remote Similarity NPC36434

  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 NPC474673 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
0.7554 Intermediate Similarity NPD2231 Phase 2
0.7554 Intermediate Similarity NPD2235 Phase 2
0.7552 Intermediate Similarity NPD9718 Approved
0.7534 Intermediate Similarity NPD3052 Approved
0.7534 Intermediate Similarity NPD3054 Approved
0.7424 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD558 Phase 2
0.731 Intermediate Similarity NPD3180 Approved
0.731 Intermediate Similarity NPD3179 Approved
0.7273 Intermediate Similarity NPD1820 Approved
0.7273 Intermediate Similarity NPD1819 Approved
0.7273 Intermediate Similarity NPD1818 Approved
0.7273 Intermediate Similarity NPD1817 Approved
0.726 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD1423 Approved
0.7122 Intermediate Similarity NPD16 Approved
0.7122 Intermediate Similarity NPD856 Approved
0.7075 Intermediate Similarity NPD3165 Approved
0.7075 Intermediate Similarity NPD3166 Approved
0.7075 Intermediate Similarity NPD3164 Approved
0.7075 Intermediate Similarity NPD3167 Approved
0.7039 Intermediate Similarity NPD3175 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD1794 Approved
0.7014 Intermediate Similarity NPD2428 Approved
0.7014 Intermediate Similarity NPD2429 Approved
0.7013 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD600 Approved
0.7007 Intermediate Similarity NPD596 Approved
0.7006 Intermediate Similarity NPD3536 Discontinued
0.7 Intermediate Similarity NPD317 Approved
0.7 Intermediate Similarity NPD318 Approved
0.6986 Remote Similarity NPD3691 Phase 2
0.6986 Remote Similarity NPD3690 Phase 2
0.6981 Remote Similarity NPD3687 Approved
0.6981 Remote Similarity NPD3686 Approved
0.6972 Remote Similarity NPD2554 Approved
0.6972 Remote Similarity NPD2556 Approved
0.6903 Remote Similarity NPD4162 Approved
0.6903 Remote Similarity NPD3060 Approved
0.6897 Remote Similarity NPD3685 Discontinued
0.6884 Remote Similarity NPD821 Approved
0.6867 Remote Similarity NPD839 Approved
0.6867 Remote Similarity NPD840 Approved
0.6855 Remote Similarity NPD2183 Approved
0.6855 Remote Similarity NPD2184 Approved
0.6853 Remote Similarity NPD9384 Approved
0.6853 Remote Similarity NPD9381 Approved
0.6849 Remote Similarity NPD196 Phase 1
0.6846 Remote Similarity NPD5163 Phase 2
0.6846 Remote Similarity NPD6179 Discontinued
0.6839 Remote Similarity NPD7153 Discontinued
0.6835 Remote Similarity NPD594 Approved
0.6835 Remote Similarity NPD592 Approved
0.6828 Remote Similarity NPD2562 Approved
0.6828 Remote Similarity NPD2561 Approved
0.6815 Remote Similarity NPD2677 Approved
0.6792 Remote Similarity NPD6419 Discontinued
0.6781 Remote Similarity NPD6582 Phase 2
0.6781 Remote Similarity NPD6583 Phase 3
0.6779 Remote Similarity NPD2614 Approved
0.6755 Remote Similarity NPD3163 Approved
0.6755 Remote Similarity NPD3162 Approved
0.675 Remote Similarity NPD7527 Clinical (unspecified phase)
0.675 Remote Similarity NPD52 Approved
0.675 Remote Similarity NPD7526 Approved
0.675 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6736 Remote Similarity NPD2668 Approved
0.6736 Remote Similarity NPD2667 Approved
0.6715 Remote Similarity NPD2684 Approved
0.6711 Remote Similarity NPD3597 Clinical (unspecified phase)
0.671 Remote Similarity NPD2240 Approved
0.671 Remote Similarity NPD2239 Approved
0.6689 Remote Similarity NPD1129 Approved
0.6689 Remote Similarity NPD1770 Clinical (unspecified phase)
0.6689 Remote Similarity NPD1135 Approved
0.6689 Remote Similarity NPD1131 Approved
0.6689 Remote Similarity NPD1133 Approved
0.6689 Remote Similarity NPD1134 Approved
0.6688 Remote Similarity NPD5061 Approved
0.6688 Remote Similarity NPD5062 Approved
0.6688 Remote Similarity NPD2460 Phase 3
0.6688 Remote Similarity NPD2458 Approved
0.6688 Remote Similarity NPD2459 Approved
0.6687 Remote Similarity NPD3158 Phase 1
0.6687 Remote Similarity NPD3985 Discontinued
0.6687 Remote Similarity NPD3157 Approved
0.6667 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9608 Approved
0.6667 Remote Similarity NPD9614 Approved
0.6667 Remote Similarity NPD9610 Approved
0.6667 Remote Similarity NPD593 Approved
0.6667 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9618 Approved
0.6667 Remote Similarity NPD3049 Approved
0.6667 Remote Similarity NPD9622 Approved
0.6667 Remote Similarity NPD595 Approved
0.6645 Remote Similarity NPD5745 Approved
0.6645 Remote Similarity NPD3530 Approved
0.6645 Remote Similarity NPD3532 Approved
0.6645 Remote Similarity NPD3531 Approved
0.6645 Remote Similarity NPD6405 Approved
0.6645 Remote Similarity NPD6407 Approved
0.6644 Remote Similarity NPD6584 Phase 3
0.6625 Remote Similarity NPD1774 Approved
0.6604 Remote Similarity NPD5160 Discontinued
0.6603 Remote Similarity NPD1538 Phase 1
0.6603 Remote Similarity NPD1523 Approved
0.6603 Remote Similarity NPD1537 Approved
0.6603 Remote Similarity NPD1522 Approved
0.6603 Remote Similarity NPD1519 Approved
0.6601 Remote Similarity NPD2238 Phase 2
0.6597 Remote Similarity NPD1548 Phase 1
0.6584 Remote Similarity NPD2874 Phase 2
0.6582 Remote Similarity NPD4237 Approved
0.6582 Remote Similarity NPD4236 Phase 3
0.6581 Remote Similarity NPD1521 Approved
0.6581 Remote Similarity NPD1520 Approved
0.6581 Remote Similarity NPD1536 Approved
0.6577 Remote Similarity NPD3568 Approved
0.6577 Remote Similarity NPD3567 Approved
0.6573 Remote Similarity NPD3596 Phase 2
0.6566 Remote Similarity NPD5773 Approved
0.6566 Remote Similarity NPD5772 Approved
0.6562 Remote Similarity NPD3122 Phase 3
0.6561 Remote Similarity NPD1375 Discontinued
0.6545 Remote Similarity NPD6072 Discontinued
0.6541 Remote Similarity NPD9611 Approved
0.6541 Remote Similarity NPD9609 Approved
0.6541 Remote Similarity NPD9612 Approved
0.6538 Remote Similarity NPD2154 Approved
0.6538 Remote Similarity NPD2156 Approved
0.6538 Remote Similarity NPD2155 Approved
0.6536 Remote Similarity NPD2245 Discovery
0.6533 Remote Similarity NPD9621 Approved
0.6533 Remote Similarity NPD9620 Approved
0.6533 Remote Similarity NPD9619 Approved
0.6528 Remote Similarity NPD9613 Approved
0.6528 Remote Similarity NPD9615 Approved
0.6528 Remote Similarity NPD9616 Approved
0.6525 Remote Similarity NPD7843 Approved
0.6522 Remote Similarity NPD7212 Phase 2
0.6522 Remote Similarity NPD290 Approved
0.6522 Remote Similarity NPD7213 Phase 3
0.6513 Remote Similarity NPD5746 Approved
0.6509 Remote Similarity NPD5709 Phase 3
0.6506 Remote Similarity NPD4018 Clinical (unspecified phase)
0.6485 Remote Similarity NPD1009 Approved
0.6483 Remote Similarity NPD316 Approved
0.6483 Remote Similarity NPD6581 Approved
0.6483 Remote Similarity NPD6580 Approved
0.6481 Remote Similarity NPD4123 Phase 3
0.6471 Remote Similarity NPD1336 Approved
0.6471 Remote Similarity NPD4666 Phase 3
0.6471 Remote Similarity NPD597 Approved
0.6471 Remote Similarity NPD601 Approved
0.6471 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6471 Remote Similarity NPD598 Approved
0.6467 Remote Similarity NPD3465 Clinical (unspecified phase)
0.646 Remote Similarity NPD6666 Approved
0.646 Remote Similarity NPD6667 Approved
0.6449 Remote Similarity NPD968 Approved
0.6446 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6443 Remote Similarity NPD4129 Approved
0.6438 Remote Similarity NPD6830 Clinical (unspecified phase)
0.6433 Remote Similarity NPD7425 Clinical (unspecified phase)
0.6429 Remote Similarity NPD1132 Approved
0.6429 Remote Similarity NPD1136 Approved
0.6429 Remote Similarity NPD3558 Approved
0.6429 Remote Similarity NPD829 Discontinued
0.6429 Remote Similarity NPD3559 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3560 Approved
0.6429 Remote Similarity NPD3556 Approved
0.6429 Remote Similarity NPD3557 Approved
0.6429 Remote Similarity NPD1130 Approved
0.6424 Remote Similarity NPD859 Approved
0.6424 Remote Similarity NPD599 Approved
0.6424 Remote Similarity NPD858 Approved
0.6424 Remote Similarity NPD602 Approved
0.6419 Remote Similarity NPD1091 Approved
0.6419 Remote Similarity NPD1610 Phase 2
0.6415 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6415 Remote Similarity NPD2030 Discontinued
0.641 Remote Similarity NPD5314 Approved
0.6408 Remote Similarity NPD9379 Approved
0.6408 Remote Similarity NPD9377 Approved
0.6402 Remote Similarity NPD5586 Clinical (unspecified phase)
0.6395 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6392 Remote Similarity NPD2161 Phase 2
0.6392 Remote Similarity NPD3156 Discontinued
0.6389 Remote Similarity NPD7157 Approved
0.6389 Remote Similarity NPD2557 Approved
0.6387 Remote Similarity NPD3061 Approved
0.6387 Remote Similarity NPD3059 Approved
0.6387 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6387 Remote Similarity NPD3062 Approved
0.6384 Remote Similarity NPD1298 Discontinued
0.6382 Remote Similarity NPD2861 Phase 2
0.6382 Remote Similarity NPD4993 Discontinued
0.6382 Remote Similarity NPD1712 Approved
0.638 Remote Similarity NPD7447 Phase 1

  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