Structure

Physi-Chem Properties

Molecular Weight:  322.25
Volume:  352.541
LogP:  3.551
LogD:  3.404
LogS:  -4.391
# Rotatable Bonds:  4
TPSA:  52.99
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.613
Synthetic Accessibility Score:  5.146
Fsp3:  0.9
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.725
MDCK Permeability:  2.2774234821554273e-05
Pgp-inhibitor:  0.024
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.241
Plasma Protein Binding (PPB):  87.2817611694336%
Volume Distribution (VD):  1.288
Pgp-substrate:  16.27734375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.014
CYP1A2-substrate:  0.749
CYP2C19-inhibitor:  0.036
CYP2C19-substrate:  0.91
CYP2C9-inhibitor:  0.069
CYP2C9-substrate:  0.081
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.113
CYP3A4-inhibitor:  0.86
CYP3A4-substrate:  0.671

ADMET: Excretion

Clearance (CL):  5.662
Half-life (T1/2):  0.334

ADMET: Toxicity

hERG Blockers:  0.05
Human Hepatotoxicity (H-HT):  0.179
Drug-inuced Liver Injury (DILI):  0.021
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.085
Maximum Recommended Daily Dose:  0.029
Skin Sensitization:  0.508
Carcinogencity:  0.029
Eye Corrosion:  0.5
Eye Irritation:  0.831
Respiratory Toxicity:  0.851

Download Data

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

  Natural Product: NPC477977

Natural Product ID:  NPC477977
Common Name*:   spongidine D
IUPAC Name:   2-[(4bR,10aS)-4b,7,7,10a-tetramethyl-6,6a,8,9,10,10b,11,12-octahydro-5H-naphtho[2,1-f]isoquinolin-2-ium-2-yl]ethanesulfonic acid
Synonyms:   spongidine D
Standard InCHIKey:  FVJKDVMYGYXUKD-AEDUHMMZSA-O
Standard InCHI:  InChI=1S/C23H35NO3S/c1-21(2)10-5-11-23(4)19(21)8-12-22(3)18-9-13-24(14-15-28(25,26)27)16-17(18)6-7-20(22)23/h9,13,16,19-20H,5-8,10-12,14-15H2,1-4H3/p+1/t19?,20?,22-,23-/m0/s1
SMILES:  C[C@]12CCCC(C1CC[C@@]3(C2CCC4=C3C=C[N+](=C4)CCS(=O)(=O)O)C)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   10453967
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines and derivatives
        • [CHEMONTID:0001764] Pyridinium derivatives

*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
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. Tongoa, Vanuatu Islands 1996 PMID[10757711]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[12662110]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[15497946]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. Tong-Yong City in the South Sea, Korea n.a. PMID[16905319]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[17567172]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[17988093]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[18407692]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. Indonesian n.a. PMID[24992702]

☑ 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
NPT2 Others Unspecified Inhibition = 0 % PMID[10757711]
NPT2 Others Unspecified Inhibition = 7.6 % PMID[10757711]
NPT2 Others Unspecified Inhibition = 48.2 % PMID[10757711]
NPT2 Others Unspecified Inhibition = 19.6 % PMID[10757711]
NPT2 Others Unspecified Inhibition = 37.6 % PMID[10757711]

☑ 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 NPC477977 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
0.8255 Intermediate Similarity NPC477974
0.7681 Intermediate Similarity NPC240136
0.7681 Intermediate Similarity NPC297486
0.7681 Intermediate Similarity NPC471402
0.764 Intermediate Similarity NPC477975
0.7535 Intermediate Similarity NPC329825
0.75 Intermediate Similarity NPC91958
0.7483 Intermediate Similarity NPC290094
0.7431 Intermediate Similarity NPC476322
0.7378 Intermediate Similarity NPC98187
0.7376 Intermediate Similarity NPC143603
0.7375 Intermediate Similarity NPC51054
0.7365 Intermediate Similarity NPC69914
0.7329 Intermediate Similarity NPC169625
0.7329 Intermediate Similarity NPC202957
0.7303 Intermediate Similarity NPC314102
0.7303 Intermediate Similarity NPC251722
0.7297 Intermediate Similarity NPC329896
0.7297 Intermediate Similarity NPC475090
0.7297 Intermediate Similarity NPC475105
0.7297 Intermediate Similarity NPC476131
0.723 Intermediate Similarity NPC89490
0.7222 Intermediate Similarity NPC469897
0.7202 Intermediate Similarity NPC477976
0.72 Intermediate Similarity NPC101165
0.7178 Intermediate Similarity NPC206819
0.7178 Intermediate Similarity NPC318065
0.7178 Intermediate Similarity NPC41257
0.7174 Intermediate Similarity NPC27802
0.7117 Intermediate Similarity NPC193740
0.7117 Intermediate Similarity NPC286427
0.7103 Intermediate Similarity NPC182570
0.7103 Intermediate Similarity NPC48564
0.7103 Intermediate Similarity NPC265605
0.7097 Intermediate Similarity NPC32002
0.7097 Intermediate Similarity NPC316811
0.7097 Intermediate Similarity NPC315348
0.7078 Intermediate Similarity NPC150259
0.707 Intermediate Similarity NPC20144
0.7047 Intermediate Similarity NPC471313
0.7047 Intermediate Similarity NPC471311
0.7032 Intermediate Similarity NPC169433
0.6981 Remote Similarity NPC469525
0.697 Remote Similarity NPC56765
0.6957 Remote Similarity NPC76540
0.6913 Remote Similarity NPC146373
0.6913 Remote Similarity NPC245244
0.6913 Remote Similarity NPC166424
0.6909 Remote Similarity NPC167635
0.6908 Remote Similarity NPC282398
0.6892 Remote Similarity NPC46358
0.6882 Remote Similarity NPC194411
0.6863 Remote Similarity NPC471322
0.6863 Remote Similarity NPC256893
0.6842 Remote Similarity NPC201634
0.6835 Remote Similarity NPC469783
0.6835 Remote Similarity NPC469767
0.6835 Remote Similarity NPC469779
0.6835 Remote Similarity NPC469768
0.6835 Remote Similarity NPC469780
0.6835 Remote Similarity NPC469784
0.6835 Remote Similarity NPC469761
0.6824 Remote Similarity NPC201700
0.681 Remote Similarity NPC40070
0.6807 Remote Similarity NPC129721
0.68 Remote Similarity NPC300688
0.6792 Remote Similarity NPC469766
0.6784 Remote Similarity NPC91895
0.6782 Remote Similarity NPC68354
0.6772 Remote Similarity NPC104483
0.6772 Remote Similarity NPC73767
0.677 Remote Similarity NPC285731
0.6768 Remote Similarity NPC470233
0.6763 Remote Similarity NPC275305
0.6763 Remote Similarity NPC37423
0.6759 Remote Similarity NPC476566
0.6746 Remote Similarity NPC478182
0.6743 Remote Similarity NPC215795
0.6743 Remote Similarity NPC176199
0.6733 Remote Similarity NPC27740
0.6727 Remote Similarity NPC200214
0.6707 Remote Similarity NPC33421
0.6707 Remote Similarity NPC53947
0.6705 Remote Similarity NPC471997
0.6688 Remote Similarity NPC29886
0.6688 Remote Similarity NPC261195
0.6687 Remote Similarity NPC471957
0.6687 Remote Similarity NPC470111
0.6686 Remote Similarity NPC151939
0.6667 Remote Similarity NPC110126
0.6667 Remote Similarity NPC470823
0.6667 Remote Similarity NPC216713
0.6647 Remote Similarity NPC90723
0.6647 Remote Similarity NPC473057
0.6646 Remote Similarity NPC471312
0.6646 Remote Similarity NPC84911
0.6627 Remote Similarity NPC44773
0.6627 Remote Similarity NPC200743
0.6627 Remote Similarity NPC215584
0.661 Remote Similarity NPC477042
0.6607 Remote Similarity NPC216643
0.6606 Remote Similarity NPC24678
0.6606 Remote Similarity NPC105818
0.6597 Remote Similarity NPC235843
0.6591 Remote Similarity NPC248454
0.6585 Remote Similarity NPC477134
0.6582 Remote Similarity NPC96102
0.6576 Remote Similarity NPC103230
0.657 Remote Similarity NPC49954
0.657 Remote Similarity NPC474561
0.6568 Remote Similarity NPC293487
0.6564 Remote Similarity NPC86288
0.6564 Remote Similarity NPC314372
0.6554 Remote Similarity NPC213468
0.6552 Remote Similarity NPC473901
0.6543 Remote Similarity NPC190296
0.6541 Remote Similarity NPC65408
0.6541 Remote Similarity NPC105127
0.6538 Remote Similarity NPC324611
0.6532 Remote Similarity NPC70949
0.6532 Remote Similarity NPC63751
0.6527 Remote Similarity NPC469760
0.6527 Remote Similarity NPC259644
0.6527 Remote Similarity NPC469786
0.6527 Remote Similarity NPC469765
0.6527 Remote Similarity NPC25008
0.6527 Remote Similarity NPC469763
0.6527 Remote Similarity NPC73952
0.6524 Remote Similarity NPC288838
0.6524 Remote Similarity NPC143872
0.6522 Remote Similarity NPC47190
0.6522 Remote Similarity NPC83987
0.6513 Remote Similarity NPC122718
0.6503 Remote Similarity NPC471323
0.6494 Remote Similarity NPC116961
0.6488 Remote Similarity NPC75540
0.6488 Remote Similarity NPC70922
0.6488 Remote Similarity NPC80597
0.6488 Remote Similarity NPC212376
0.6488 Remote Similarity NPC211572
0.6486 Remote Similarity NPC81561
0.6479 Remote Similarity NPC231655
0.6474 Remote Similarity NPC478183
0.6453 Remote Similarity NPC469541
0.6453 Remote Similarity NPC478184
0.6453 Remote Similarity NPC194640
0.6444 Remote Similarity NPC163055
0.6443 Remote Similarity NPC162689
0.6443 Remote Similarity NPC54102
0.6433 Remote Similarity NPC82295
0.6429 Remote Similarity NPC138842
0.6429 Remote Similarity NPC325903
0.642 Remote Similarity NPC279081
0.642 Remote Similarity NPC2949
0.6419 Remote Similarity NPC313449
0.6419 Remote Similarity NPC148140
0.6419 Remote Similarity NPC192209
0.6412 Remote Similarity NPC469762
0.64 Remote Similarity NPC11863
0.64 Remote Similarity NPC32534
0.6395 Remote Similarity NPC282231
0.6395 Remote Similarity NPC478185
0.6386 Remote Similarity NPC179787
0.6386 Remote Similarity NPC201380
0.6384 Remote Similarity NPC469938
0.6382 Remote Similarity NPC56856
0.638 Remote Similarity NPC476454
0.6379 Remote Similarity NPC160105
0.6374 Remote Similarity NPC92796
0.6374 Remote Similarity NPC6436
0.6374 Remote Similarity NPC475990
0.6374 Remote Similarity NPC135141
0.637 Remote Similarity NPC187036
0.6369 Remote Similarity NPC22079
0.6369 Remote Similarity NPC315320
0.6369 Remote Similarity NPC248462
0.6369 Remote Similarity NPC53044
0.6364 Remote Similarity NPC159856
0.6364 Remote Similarity NPC126492
0.6359 Remote Similarity NPC255909
0.6358 Remote Similarity NPC311276
0.6358 Remote Similarity NPC474217
0.6358 Remote Similarity NPC215519
0.6358 Remote Similarity NPC40779
0.6353 Remote Similarity NPC469785
0.6348 Remote Similarity NPC280852
0.6347 Remote Similarity NPC321911
0.6347 Remote Similarity NPC37548
0.6347 Remote Similarity NPC187951
0.6344 Remote Similarity NPC316018
0.6344 Remote Similarity NPC314058
0.6337 Remote Similarity NPC81229
0.6337 Remote Similarity NPC279918
0.6337 Remote Similarity NPC255229
0.6331 Remote Similarity NPC281094
0.6329 Remote Similarity NPC475450
0.6325 Remote Similarity NPC63545
0.6324 Remote Similarity NPC268966
0.6324 Remote Similarity NPC3715
0.6323 Remote Similarity NPC476140

  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 NPC477977 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
0.8092 Intermediate Similarity NPD4641 Discontinued
0.7823 Intermediate Similarity NPD792 Discontinued
0.7748 Intermediate Similarity NPD4510 Discontinued
0.7639 Intermediate Similarity NPD2119 Approved
0.7639 Intermediate Similarity NPD2118 Approved
0.7625 Intermediate Similarity NPD5315 Discontinued
0.7593 Intermediate Similarity NPD5636 Discontinued
0.745 Intermediate Similarity NPD4029 Approved
0.745 Intermediate Similarity NPD3944 Approved
0.745 Intermediate Similarity NPD4030 Approved
0.745 Intermediate Similarity NPD4028 Approved
0.745 Intermediate Similarity NPD3942 Approved
0.7439 Intermediate Similarity NPD2641 Approved
0.7439 Intermediate Similarity NPD2640 Approved
0.7375 Intermediate Similarity NPD6026 Approved
0.7365 Intermediate Similarity NPD3476 Approved
0.7365 Intermediate Similarity NPD3475 Approved
0.7362 Intermediate Similarity NPD6635 Approved
0.7346 Intermediate Similarity NPD1404 Approved
0.7346 Intermediate Similarity NPD1403 Approved
0.7333 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD4824 Approved
0.7319 Intermediate Similarity NPD4823 Approved
0.7273 Intermediate Similarity NPD2639 Approved
0.7273 Intermediate Similarity NPD2642 Approved
0.7229 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD2089 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD9583 Approved
0.7152 Intermediate Similarity NPD7469 Discontinued
0.7152 Intermediate Similarity NPD1993 Approved
0.7152 Intermediate Similarity NPD1994 Approved
0.7152 Intermediate Similarity NPD1995 Approved
0.7143 Intermediate Similarity NPD3609 Approved
0.7143 Intermediate Similarity NPD3610 Approved
0.7126 Intermediate Similarity NPD4638 Approved
0.7126 Intermediate Similarity NPD4639 Approved
0.7126 Intermediate Similarity NPD4640 Approved
0.7117 Intermediate Similarity NPD5541 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD7021 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD271 Approved
0.7103 Intermediate Similarity NPD268 Approved
0.7099 Intermediate Similarity NPD1328 Approved
0.7097 Intermediate Similarity NPD2069 Approved
0.7097 Intermediate Similarity NPD2068 Approved
0.7097 Intermediate Similarity NPD2072 Approved
0.7097 Intermediate Similarity NPD2070 Approved
0.7097 Intermediate Similarity NPD2073 Approved
0.7097 Intermediate Similarity NPD2074 Approved
0.7097 Intermediate Similarity NPD2075 Approved
0.7097 Intermediate Similarity NPD2071 Approved
0.7075 Intermediate Similarity NPD9357 Approved
0.7048 Intermediate Similarity NPD3323 Discontinued
0.7018 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD2145 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD5105 Approved
0.7011 Intermediate Similarity NPD5106 Approved
0.7 Intermediate Similarity NPD4703 Approved
0.7 Intermediate Similarity NPD4702 Approved
0.7 Intermediate Similarity NPD4547 Phase 3
0.6988 Remote Similarity NPD2385 Clinical (unspecified phase)
0.6964 Remote Similarity NPD6446 Discontinued
0.6957 Remote Similarity NPD3100 Discontinued
0.6951 Remote Similarity NPD2580 Discontinued
0.6937 Remote Similarity NPD6148 Clinical (unspecified phase)
0.6933 Remote Similarity NPD991 Phase 2
0.6933 Remote Similarity NPD992 Clinical (unspecified phase)
0.6928 Remote Similarity NPD1627 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2896 Discontinued
0.6919 Remote Similarity NPD6044 Discontinued
0.6894 Remote Similarity NPD1661 Suspended
0.6883 Remote Similarity NPD3385 Approved
0.686 Remote Similarity NPD3859 Clinical (unspecified phase)
0.6855 Remote Similarity NPD3717 Discontinued
0.6852 Remote Similarity NPD4374 Clinical (unspecified phase)
0.6839 Remote Similarity NPD2142 Approved
0.6839 Remote Similarity NPD2141 Approved
0.6839 Remote Similarity NPD2140 Approved
0.6826 Remote Similarity NPD6454 Clinical (unspecified phase)
0.6821 Remote Similarity NPD2771 Approved
0.6821 Remote Similarity NPD1598 Discontinued
0.6813 Remote Similarity NPD3813 Approved
0.6813 Remote Similarity NPD3401 Clinical (unspecified phase)
0.6813 Remote Similarity NPD751 Clinical (unspecified phase)
0.6813 Remote Similarity NPD1918 Clinical (unspecified phase)
0.681 Remote Similarity NPD2462 Phase 3
0.681 Remote Similarity NPD8353 Approved
0.681 Remote Similarity NPD8355 Approved
0.681 Remote Similarity NPD2465 Approved
0.681 Remote Similarity NPD2466 Phase 3
0.6806 Remote Similarity NPD269 Clinical (unspecified phase)
0.6782 Remote Similarity NPD3506 Approved
0.6782 Remote Similarity NPD3505 Approved
0.6768 Remote Similarity NPD3262 Approved
0.6766 Remote Similarity NPD1679 Approved
0.676 Remote Similarity NPD5590 Clinical (unspecified phase)
0.675 Remote Similarity NPD2007 Clinical (unspecified phase)
0.6743 Remote Similarity NPD4076 Approved
0.6743 Remote Similarity NPD2084 Discontinued
0.6743 Remote Similarity NPD4079 Approved
0.6742 Remote Similarity NPD6241 Phase 1
0.6732 Remote Similarity NPD3654 Approved
0.6727 Remote Similarity NPD8354 Approved
0.6725 Remote Similarity NPD7287 Clinical (unspecified phase)
0.6724 Remote Similarity NPD3348 Phase 2
0.6724 Remote Similarity NPD4075 Phase 2
0.6711 Remote Similarity NPD748 Clinical (unspecified phase)
0.6708 Remote Similarity NPD4509 Discontinued
0.6707 Remote Similarity NPD6497 Approved
0.6707 Remote Similarity NPD2172 Phase 1
0.6688 Remote Similarity NPD206 Clinical (unspecified phase)
0.6688 Remote Similarity NPD715 Phase 3
0.6687 Remote Similarity NPD1722 Approved
0.6686 Remote Similarity NPD2620 Phase 2
0.6686 Remote Similarity NPD2619 Clinical (unspecified phase)
0.6686 Remote Similarity NPD5400 Approved
0.6667 Remote Similarity NPD786 Approved
0.6667 Remote Similarity NPD4128 Approved
0.6629 Remote Similarity NPD6194 Discontinued
0.6629 Remote Similarity NPD7401 Clinical (unspecified phase)
0.6627 Remote Similarity NPD2511 Approved
0.6608 Remote Similarity NPD2719 Clinical (unspecified phase)
0.6608 Remote Similarity NPD2780 Approved
0.6608 Remote Similarity NPD2782 Approved
0.6608 Remote Similarity NPD2720 Phase 1
0.6593 Remote Similarity NPD6281 Approved
0.6591 Remote Similarity NPD4181 Approved
0.6588 Remote Similarity NPD6771 Discontinued
0.6588 Remote Similarity NPD4384 Clinical (unspecified phase)
0.6585 Remote Similarity NPD1270 Approved
0.6582 Remote Similarity NPD198 Clinical (unspecified phase)
0.6575 Remote Similarity NPD3961 Discontinued
0.6568 Remote Similarity NPD3433 Clinical (unspecified phase)
0.6568 Remote Similarity NPD5255 Approved
0.6566 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6562 Remote Similarity NPD768 Clinical (unspecified phase)
0.655 Remote Similarity NPD3583 Phase 2
0.6548 Remote Similarity NPD2748 Clinical (unspecified phase)
0.6545 Remote Similarity NPD2430 Phase 2
0.6543 Remote Similarity NPD2006 Phase 2
0.6543 Remote Similarity NPD4637 Clinical (unspecified phase)
0.6541 Remote Similarity NPD201 Phase 2
0.6541 Remote Similarity NPD200 Phase 2
0.6538 Remote Similarity NPD7233 Approved
0.6538 Remote Similarity NPD7175 Phase 1
0.6538 Remote Similarity NPD6363 Clinical (unspecified phase)
0.6538 Remote Similarity NPD7234 Approved
0.6534 Remote Similarity NPD3238 Discontinued
0.6532 Remote Similarity NPD2781 Approved
0.6532 Remote Similarity NPD5862 Discovery
0.6527 Remote Similarity NPD2012 Clinical (unspecified phase)
0.6527 Remote Similarity NPD2837 Discontinued
0.6527 Remote Similarity NPD3339 Approved
0.6517 Remote Similarity NPD6277 Clinical (unspecified phase)
0.6512 Remote Similarity NPD5744 Clinical (unspecified phase)
0.6509 Remote Similarity NPD2581 Approved
0.6509 Remote Similarity NPD2582 Approved
0.6503 Remote Similarity NPD5254 Discontinued
0.6497 Remote Similarity NPD8122 Approved
0.6497 Remote Similarity NPD8123 Approved
0.6497 Remote Similarity NPD2753 Discontinued
0.6497 Remote Similarity NPD4398 Clinical (unspecified phase)
0.6497 Remote Similarity NPD7111 Discontinued
0.6494 Remote Similarity NPD5412 Discontinued
0.6494 Remote Similarity NPD4973 Approved
0.6491 Remote Similarity NPD8026 Phase 1
0.6488 Remote Similarity NPD2809 Approved
0.6484 Remote Similarity NPD8431 Approved
0.6479 Remote Similarity NPD9098 Phase 3
0.6479 Remote Similarity NPD9099 Clinical (unspecified phase)
0.6474 Remote Similarity NPD3929 Clinical (unspecified phase)
0.6474 Remote Similarity NPD7561 Approved
0.6471 Remote Similarity NPD5418 Discontinued
0.6467 Remote Similarity NPD6626 Approved
0.6457 Remote Similarity NPD5934 Clinical (unspecified phase)
0.6455 Remote Similarity NPD5043 Discontinued
0.6453 Remote Similarity NPD8129 Discovery
0.6448 Remote Similarity NPD8110 Clinical (unspecified phase)
0.6444 Remote Similarity NPD5213 Clinical (unspecified phase)
0.6442 Remote Similarity NPD4047 Discontinued
0.6441 Remote Similarity NPD5100 Phase 3
0.6441 Remote Similarity NPD7402 Clinical (unspecified phase)
0.6441 Remote Similarity NPD5843 Discontinued
0.6438 Remote Similarity NPD45 Approved
0.6438 Remote Similarity NPD6554 Approved
0.6437 Remote Similarity NPD5069 Clinical (unspecified phase)
0.6432 Remote Similarity NPD7127 Clinical (unspecified phase)
0.6424 Remote Similarity NPD1683 Approved
0.642 Remote Similarity NPD3943 Clinical (unspecified phase)
0.642 Remote Similarity NPD1395 Clinical (unspecified phase)
0.6419 Remote Similarity NPD7481 Approved
0.6419 Remote Similarity NPD7480 Approved
0.6415 Remote Similarity NPD4880 Discontinued
0.6409 Remote Similarity NPD7564 Discontinued
0.6404 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6404 Remote Similarity NPD6203 Clinical (unspecified phase)
0.6402 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6402 Remote Similarity NPD6488 Phase 1
0.6393 Remote Similarity NPD7394 Phase 2
0.6393 Remote Similarity NPD2310 Clinical (unspecified phase)

  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