Structure

Physi-Chem Properties

Molecular Weight:  630.3
Volume:  637.995
LogP:  3.763
LogD:  2.558
LogS:  -4.143
# Rotatable Bonds:  14
TPSA:  151.1
# H-Bond Aceptor:  11
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.151
Synthetic Accessibility Score:  5.987
Fsp3:  0.647
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:  -5.185
MDCK Permeability:  3.712707257363945e-05
Pgp-inhibitor:  0.996
Pgp-substrate:  0.708
Human Intestinal Absorption (HIA):  0.055
20% Bioavailability (F20%):  0.977
30% Bioavailability (F30%):  0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.066
Plasma Protein Binding (PPB):  90.65692901611328%
Volume Distribution (VD):  1.728
Pgp-substrate:  4.965545177459717%

ADMET: Metabolism

CYP1A2-inhibitor:  0.02
CYP1A2-substrate:  0.161
CYP2C19-inhibitor:  0.811
CYP2C19-substrate:  0.267
CYP2C9-inhibitor:  0.953
CYP2C9-substrate:  0.076
CYP2D6-inhibitor:  0.629
CYP2D6-substrate:  0.071
CYP3A4-inhibitor:  0.863
CYP3A4-substrate:  0.66

ADMET: Excretion

Clearance (CL):  5.801
Half-life (T1/2):  0.73

ADMET: Toxicity

hERG Blockers:  0.097
Human Hepatotoxicity (H-HT):  0.839
Drug-inuced Liver Injury (DILI):  0.816
AMES Toxicity:  0.04
Rat Oral Acute Toxicity:  0.558
Maximum Recommended Daily Dose:  0.938
Skin Sensitization:  0.484
Carcinogencity:  0.057
Eye Corrosion:  0.003
Eye Irritation:  0.056
Respiratory Toxicity:  0.779

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

  Natural Product: NPC475446

Natural Product ID:  NPC475446
Common Name*:   ((S)-2-((1R,4R,4Ar,5S,6R,8S,8Ar)-8-Acetoxy-8A-(Acetoxymethyl)-5,6-Dimethyl-4-((Z)-2-Methylbut-2-Enoyloxy)Octahydro-2H-Spiro[Naphthalene-1,2'-Oxirane]-5-Yl)-1-(5-Oxo-2,5-Dihydrofuran-3-Yl)Ethyl) 2-Methylbut-2-Enoate
IUPAC Name:   [(1R,4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-7,8-dimethyl-8-[(2S)-2-[(Z)-2-methylbut-2-enoyl]oxy-2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (Z)-2-methylbut-2-enoate
Synonyms:  
Standard InCHIKey:  BGAZAIQJEALJJF-KMNLRVGGSA-N
Standard InCHI:  InChI=1S/C34H46O11/c1-9-19(3)30(38)44-25-11-12-33(17-42-33)34(18-41-22(6)35)27(43-23(7)36)13-21(5)32(8,29(25)34)15-26(24-14-28(37)40-16-24)45-31(39)20(4)10-2/h9-10,14,21,25-27,29H,11-13,15-18H2,1-8H3/b19-9-,20-10-/t21-,25-,26+,27+,29-,32+,33+,34-/m1/s1
SMILES:  C/C=C(C(=O)O[C@@H]1CC[C@@]2([C@]3([C@H]1[C@@](C)(C[C@@H](C1=CC(=O)OC1)OC(=O)/C(=CC)/C)[C@H](C)C[C@@H]3OC(=O)C)COC(=O)C)CO2)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL505822
PubChem CID:   44566361
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002995] Pentacarboxylic acids and 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
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota flowering whole plant n.a. n.a. PMID[10425119]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[9748375]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17539 Ajuga decumbens Species Lamiaceae 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
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[492900]
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[492900]
NPT2 Others Unspecified Activity = 100.0 % PMID[492900]
NPT2 Others Unspecified Activity = 18.4 % PMID[492900]
NPT2 Others Unspecified Activity = 71.5 % PMID[492900]
NPT2 Others Unspecified Activity = 47.2 % PMID[492900]

☑ 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 NPC475446 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 NPC311241
0.989 High Similarity NPC107806
0.989 High Similarity NPC72647
0.9889 High Similarity NPC475380
0.9889 High Similarity NPC209297
0.978 High Similarity NPC100912
0.9667 High Similarity NPC140277
0.9457 High Similarity NPC194132
0.9368 High Similarity NPC475038
0.9368 High Similarity NPC109195
0.9111 High Similarity NPC93411
0.9032 High Similarity NPC161998
0.8925 High Similarity NPC7349
0.883 High Similarity NPC105490
0.8763 High Similarity NPC16601
0.8673 High Similarity NPC11974
0.8614 High Similarity NPC319438
0.8586 High Similarity NPC162973
0.8542 High Similarity NPC276110
0.8529 High Similarity NPC181994
0.85 High Similarity NPC471938
0.8495 Intermediate Similarity NPC106332
0.8447 Intermediate Similarity NPC322912
0.8431 Intermediate Similarity NPC216636
0.8416 Intermediate Similarity NPC471937
0.84 Intermediate Similarity NPC472552
0.84 Intermediate Similarity NPC471914
0.8384 Intermediate Similarity NPC324841
0.8384 Intermediate Similarity NPC471413
0.837 Intermediate Similarity NPC474013
0.8351 Intermediate Similarity NPC476519
0.8333 Intermediate Similarity NPC51719
0.83 Intermediate Similarity NPC472554
0.83 Intermediate Similarity NPC471412
0.8283 Intermediate Similarity NPC278673
0.8265 Intermediate Similarity NPC260796
0.8252 Intermediate Similarity NPC471205
0.8222 Intermediate Similarity NPC469802
0.8218 Intermediate Similarity NPC476081
0.82 Intermediate Similarity NPC38855
0.8191 Intermediate Similarity NPC102640
0.8191 Intermediate Similarity NPC475087
0.8182 Intermediate Similarity NPC51499
0.8163 Intermediate Similarity NPC111273
0.8163 Intermediate Similarity NPC471915
0.8155 Intermediate Similarity NPC218158
0.8155 Intermediate Similarity NPC471206
0.8137 Intermediate Similarity NPC120009
0.8137 Intermediate Similarity NPC165608
0.8137 Intermediate Similarity NPC160583
0.8125 Intermediate Similarity NPC78973
0.8105 Intermediate Similarity NPC69713
0.81 Intermediate Similarity NPC325229
0.81 Intermediate Similarity NPC275086
0.8095 Intermediate Similarity NPC475586
0.8085 Intermediate Similarity NPC102996
0.8085 Intermediate Similarity NPC131813
0.8081 Intermediate Similarity NPC29952
0.8081 Intermediate Similarity NPC134072
0.8081 Intermediate Similarity NPC234993
0.8077 Intermediate Similarity NPC122816
0.8065 Intermediate Similarity NPC96055
0.8065 Intermediate Similarity NPC306951
0.8065 Intermediate Similarity NPC32223
0.8043 Intermediate Similarity NPC471218
0.8041 Intermediate Similarity NPC78594
0.8041 Intermediate Similarity NPC473944
0.8021 Intermediate Similarity NPC170633
0.802 Intermediate Similarity NPC473545
0.802 Intermediate Similarity NPC472187
0.8019 Intermediate Similarity NPC253906
0.8 Intermediate Similarity NPC474921
0.8 Intermediate Similarity NPC264546
0.8 Intermediate Similarity NPC475263
0.8 Intermediate Similarity NPC166857
0.7982 Intermediate Similarity NPC470793
0.7981 Intermediate Similarity NPC477090
0.7981 Intermediate Similarity NPC119855
0.7981 Intermediate Similarity NPC34768
0.7981 Intermediate Similarity NPC220217
0.798 Intermediate Similarity NPC472441
0.7961 Intermediate Similarity NPC196471
0.7961 Intermediate Similarity NPC10232
0.7961 Intermediate Similarity NPC45897
0.7961 Intermediate Similarity NPC281378
0.7961 Intermediate Similarity NPC254202
0.7961 Intermediate Similarity NPC180204
0.7961 Intermediate Similarity NPC189588
0.7961 Intermediate Similarity NPC187302
0.7961 Intermediate Similarity NPC23584
0.7961 Intermediate Similarity NPC473523
0.7961 Intermediate Similarity NPC474822
0.7961 Intermediate Similarity NPC120321
0.7961 Intermediate Similarity NPC97487
0.7959 Intermediate Similarity NPC152778
0.7959 Intermediate Similarity NPC205034
0.7959 Intermediate Similarity NPC472640
0.7959 Intermediate Similarity NPC139692
0.7959 Intermediate Similarity NPC162615
0.7959 Intermediate Similarity NPC110022
0.7959 Intermediate Similarity NPC472641
0.7944 Intermediate Similarity NPC470076
0.7941 Intermediate Similarity NPC268829
0.7941 Intermediate Similarity NPC25177
0.7941 Intermediate Similarity NPC222875
0.7941 Intermediate Similarity NPC295110
0.7941 Intermediate Similarity NPC247701
0.7938 Intermediate Similarity NPC302280
0.7921 Intermediate Similarity NPC476800
0.7921 Intermediate Similarity NPC218107
0.7921 Intermediate Similarity NPC471366
0.7921 Intermediate Similarity NPC318917
0.7921 Intermediate Similarity NPC472186
0.7905 Intermediate Similarity NPC475074
0.7905 Intermediate Similarity NPC180744
0.7905 Intermediate Similarity NPC67321
0.7905 Intermediate Similarity NPC473586
0.7905 Intermediate Similarity NPC302788
0.7905 Intermediate Similarity NPC187435
0.7905 Intermediate Similarity NPC109376
0.79 Intermediate Similarity NPC165632
0.79 Intermediate Similarity NPC472997
0.79 Intermediate Similarity NPC472996
0.79 Intermediate Similarity NPC171598
0.79 Intermediate Similarity NPC16967
0.7895 Intermediate Similarity NPC471219
0.789 Intermediate Similarity NPC90472
0.789 Intermediate Similarity NPC43213
0.7889 Intermediate Similarity NPC189206
0.7885 Intermediate Similarity NPC477127
0.7885 Intermediate Similarity NPC473543
0.7879 Intermediate Similarity NPC57117
0.7879 Intermediate Similarity NPC477722
0.787 Intermediate Similarity NPC470063
0.7864 Intermediate Similarity NPC476471
0.7864 Intermediate Similarity NPC11956
0.7864 Intermediate Similarity NPC475344
0.7857 Intermediate Similarity NPC72845
0.7857 Intermediate Similarity NPC329842
0.7857 Intermediate Similarity NPC473675
0.785 Intermediate Similarity NPC177047
0.7843 Intermediate Similarity NPC47024
0.7843 Intermediate Similarity NPC271295
0.7843 Intermediate Similarity NPC473204
0.7843 Intermediate Similarity NPC251680
0.7838 Intermediate Similarity NPC470420
0.783 Intermediate Similarity NPC38948
0.783 Intermediate Similarity NPC470024
0.783 Intermediate Similarity NPC224660
0.783 Intermediate Similarity NPC88701
0.783 Intermediate Similarity NPC50124
0.7822 Intermediate Similarity NPC84335
0.7822 Intermediate Similarity NPC199099
0.7822 Intermediate Similarity NPC205143
0.7822 Intermediate Similarity NPC472188
0.7822 Intermediate Similarity NPC38530
0.7822 Intermediate Similarity NPC472998
0.7822 Intermediate Similarity NPC110937
0.7818 Intermediate Similarity NPC470075
0.7818 Intermediate Similarity NPC471816
0.7812 Intermediate Similarity NPC476600
0.781 Intermediate Similarity NPC172867
0.781 Intermediate Similarity NPC81630
0.781 Intermediate Similarity NPC88349
0.78 Intermediate Similarity NPC469583
0.78 Intermediate Similarity NPC474909
0.78 Intermediate Similarity NPC471372
0.78 Intermediate Similarity NPC281134
0.78 Intermediate Similarity NPC472189
0.78 Intermediate Similarity NPC471362
0.78 Intermediate Similarity NPC56369
0.7798 Intermediate Similarity NPC474937
0.7798 Intermediate Similarity NPC477126
0.7798 Intermediate Similarity NPC159333
0.7798 Intermediate Similarity NPC171126
0.7788 Intermediate Similarity NPC112009
0.7788 Intermediate Similarity NPC297617
0.7788 Intermediate Similarity NPC204731
0.7788 Intermediate Similarity NPC474124
0.7788 Intermediate Similarity NPC472821
0.7778 Intermediate Similarity NPC475657
0.7778 Intermediate Similarity NPC53555
0.7778 Intermediate Similarity NPC38232
0.7767 Intermediate Similarity NPC473160
0.7766 Intermediate Similarity NPC476927
0.7766 Intermediate Similarity NPC12283
0.7766 Intermediate Similarity NPC474193
0.7757 Intermediate Similarity NPC299590
0.7757 Intermediate Similarity NPC469370
0.7757 Intermediate Similarity NPC206618
0.7755 Intermediate Similarity NPC310479
0.7755 Intermediate Similarity NPC475776
0.7755 Intermediate Similarity NPC472642
0.7745 Intermediate Similarity NPC264378
0.7742 Intermediate Similarity NPC170303
0.7736 Intermediate Similarity NPC179380
0.7736 Intermediate Similarity NPC471601
0.7732 Intermediate Similarity NPC473879
0.7732 Intermediate Similarity NPC291665
0.7727 Intermediate Similarity NPC216665

  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 NPC475446 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
0.8077 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD7638 Approved
0.785 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD7639 Approved
0.7843 Intermediate Similarity NPD7640 Approved
0.7757 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD6648 Approved
0.766 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7596 Intermediate Similarity NPD5344 Discontinued
0.7522 Intermediate Similarity NPD7328 Approved
0.7522 Intermediate Similarity NPD7327 Approved
0.75 Intermediate Similarity NPD6686 Approved
0.7456 Intermediate Similarity NPD7516 Approved
0.7404 Intermediate Similarity NPD4225 Approved
0.7391 Intermediate Similarity NPD8294 Approved
0.7391 Intermediate Similarity NPD8377 Approved
0.7328 Intermediate Similarity NPD8378 Approved
0.7328 Intermediate Similarity NPD8033 Approved
0.7328 Intermediate Similarity NPD8335 Approved
0.7328 Intermediate Similarity NPD8296 Approved
0.7328 Intermediate Similarity NPD8380 Approved
0.7328 Intermediate Similarity NPD8379 Approved
0.7315 Intermediate Similarity NPD6008 Approved
0.7228 Intermediate Similarity NPD7838 Discovery
0.7196 Intermediate Similarity NPD7632 Discontinued
0.7184 Intermediate Similarity NPD7900 Approved
0.7184 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD7115 Discovery
0.7129 Intermediate Similarity NPD6051 Approved
0.7083 Intermediate Similarity NPD7507 Approved
0.7071 Intermediate Similarity NPD1694 Approved
0.7034 Intermediate Similarity NPD7503 Approved
0.7019 Intermediate Similarity NPD7748 Approved
0.6981 Remote Similarity NPD7902 Approved
0.693 Remote Similarity NPD8297 Approved
0.6911 Remote Similarity NPD7319 Approved
0.6893 Remote Similarity NPD46 Approved
0.6893 Remote Similarity NPD6698 Approved
0.6875 Remote Similarity NPD6881 Approved
0.6875 Remote Similarity NPD6899 Approved
0.6847 Remote Similarity NPD6402 Approved
0.6847 Remote Similarity NPD7128 Approved
0.6847 Remote Similarity NPD5739 Approved
0.6847 Remote Similarity NPD6675 Approved
0.6842 Remote Similarity NPD6649 Approved
0.6842 Remote Similarity NPD6650 Approved
0.6842 Remote Similarity NPD8130 Phase 1
0.6832 Remote Similarity NPD7521 Approved
0.6832 Remote Similarity NPD6684 Approved
0.6832 Remote Similarity NPD7334 Approved
0.6832 Remote Similarity NPD7146 Approved
0.6832 Remote Similarity NPD6409 Approved
0.6832 Remote Similarity NPD5330 Approved
0.6814 Remote Similarity NPD6373 Approved
0.6814 Remote Similarity NPD6372 Approved
0.6792 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6786 Remote Similarity NPD5697 Approved
0.6783 Remote Similarity NPD6882 Approved
0.6765 Remote Similarity NPD3573 Approved
0.6754 Remote Similarity NPD7290 Approved
0.6754 Remote Similarity NPD6883 Approved
0.6754 Remote Similarity NPD7102 Approved
0.6726 Remote Similarity NPD7320 Approved
0.6699 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6699 Remote Similarity NPD6672 Approved
0.6699 Remote Similarity NPD6903 Approved
0.6699 Remote Similarity NPD5737 Approved
0.6696 Remote Similarity NPD6847 Approved
0.6696 Remote Similarity NPD6617 Approved
0.6696 Remote Similarity NPD6869 Approved
0.6667 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6013 Approved
0.6667 Remote Similarity NPD6014 Approved
0.6667 Remote Similarity NPD6319 Approved
0.6667 Remote Similarity NPD6012 Approved
0.6667 Remote Similarity NPD7515 Phase 2
0.6667 Remote Similarity NPD5693 Phase 1
0.6637 Remote Similarity NPD5701 Approved
0.6635 Remote Similarity NPD1695 Approved
0.6606 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6604 Remote Similarity NPD6399 Phase 3
0.6581 Remote Similarity NPD4632 Approved
0.6581 Remote Similarity NPD8133 Approved
0.6579 Remote Similarity NPD6011 Approved
0.6579 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6566 Remote Similarity NPD7525 Registered
0.6514 Remote Similarity NPD6084 Phase 2
0.6514 Remote Similarity NPD6083 Phase 2
0.6509 Remote Similarity NPD8035 Phase 2
0.6509 Remote Similarity NPD8034 Phase 2
0.6509 Remote Similarity NPD7637 Suspended
0.6504 Remote Similarity NPD7604 Phase 2
0.6496 Remote Similarity NPD6053 Discontinued
0.6491 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6476 Remote Similarity NPD6673 Approved
0.6476 Remote Similarity NPD6080 Approved
0.6476 Remote Similarity NPD6904 Approved
0.6471 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6466 Remote Similarity NPD6371 Approved
0.6452 Remote Similarity NPD7492 Approved
0.6436 Remote Similarity NPD5209 Approved
0.6429 Remote Similarity NPD5211 Phase 2
0.6429 Remote Similarity NPD7736 Approved
0.6417 Remote Similarity NPD6009 Approved
0.641 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6408 Remote Similarity NPD1733 Clinical (unspecified phase)
0.64 Remote Similarity NPD6616 Approved
0.6396 Remote Similarity NPD4696 Approved
0.6396 Remote Similarity NPD5285 Approved
0.6396 Remote Similarity NPD5286 Approved
0.6393 Remote Similarity NPD6054 Approved
0.6389 Remote Similarity NPD6001 Approved
0.6379 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6695 Phase 3
0.6371 Remote Similarity NPD8328 Phase 3
0.6364 Remote Similarity NPD4755 Approved
0.6355 Remote Similarity NPD6079 Approved
0.6349 Remote Similarity NPD8293 Discontinued
0.6349 Remote Similarity NPD7078 Approved
0.6348 Remote Similarity NPD6412 Phase 2
0.6346 Remote Similarity NPD3618 Phase 1
0.6341 Remote Similarity NPD5983 Phase 2
0.6333 Remote Similarity NPD6274 Approved
0.633 Remote Similarity NPD5695 Phase 3
0.6321 Remote Similarity NPD5328 Approved
0.6316 Remote Similarity NPD5141 Approved
0.6311 Remote Similarity NPD7101 Approved
0.6311 Remote Similarity NPD7100 Approved
0.6306 Remote Similarity NPD5696 Approved
0.63 Remote Similarity NPD7645 Phase 2
0.6296 Remote Similarity NPD4202 Approved
0.629 Remote Similarity NPD6370 Approved
0.6286 Remote Similarity NPD7750 Discontinued
0.6283 Remote Similarity NPD5225 Approved
0.6283 Remote Similarity NPD5226 Approved
0.6283 Remote Similarity NPD4633 Approved
0.6283 Remote Similarity NPD5224 Approved
0.627 Remote Similarity NPD6336 Discontinued
0.6262 Remote Similarity NPD3168 Discontinued
0.626 Remote Similarity NPD6059 Approved
0.625 Remote Similarity NPD4700 Approved
0.623 Remote Similarity NPD6335 Approved
0.6228 Remote Similarity NPD5175 Approved
0.6228 Remote Similarity NPD5174 Approved
0.6226 Remote Similarity NPD5208 Approved
0.6224 Remote Similarity NPD8039 Approved
0.621 Remote Similarity NPD6016 Approved
0.621 Remote Similarity NPD6015 Approved
0.6204 Remote Similarity NPD6050 Approved
0.6195 Remote Similarity NPD5223 Approved
0.619 Remote Similarity NPD6098 Approved
0.6186 Remote Similarity NPD4634 Approved
0.616 Remote Similarity NPD5988 Approved
0.6154 Remote Similarity NPD4729 Approved
0.6154 Remote Similarity NPD4730 Approved
0.6148 Remote Similarity NPD6317 Approved
0.6147 Remote Similarity NPD5779 Approved
0.6147 Remote Similarity NPD5778 Approved
0.6132 Remote Similarity NPD7524 Approved
0.6126 Remote Similarity NPD5221 Approved
0.6126 Remote Similarity NPD5222 Approved
0.6126 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6121 Remote Similarity NPD4768 Approved
0.6121 Remote Similarity NPD4767 Approved
0.6111 Remote Similarity NPD5692 Phase 3
0.6098 Remote Similarity NPD6313 Approved
0.6098 Remote Similarity NPD6314 Approved
0.6095 Remote Similarity NPD7520 Clinical (unspecified phase)
0.608 Remote Similarity NPD8516 Approved
0.608 Remote Similarity NPD6908 Approved
0.608 Remote Similarity NPD8515 Approved
0.608 Remote Similarity NPD8517 Approved
0.608 Remote Similarity NPD8513 Phase 3
0.608 Remote Similarity NPD6909 Approved
0.608 Remote Similarity NPD6921 Approved
0.6078 Remote Similarity NPD6930 Phase 2
0.6078 Remote Similarity NPD6931 Approved
0.6071 Remote Similarity NPD5173 Approved
0.6066 Remote Similarity NPD6868 Approved
0.6055 Remote Similarity NPD5694 Approved
0.605 Remote Similarity NPD5249 Phase 3
0.605 Remote Similarity NPD5250 Approved
0.605 Remote Similarity NPD5251 Approved
0.605 Remote Similarity NPD5248 Approved
0.605 Remote Similarity NPD5247 Approved
0.6038 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6036 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6031 Remote Similarity NPD7260 Phase 2
0.6019 Remote Similarity NPD4753 Phase 2
0.6017 Remote Similarity NPD5128 Approved
0.6016 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6 Remote Similarity NPD3665 Phase 1
0.6 Remote Similarity NPD3666 Approved
0.6 Remote Similarity NPD3668 Phase 3
0.6 Remote Similarity NPD3133 Approved
0.6 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6 Remote Similarity NPD4786 Approved
0.6 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5982 Remote Similarity NPD7732 Phase 3

  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