Structure

Physi-Chem Properties

Molecular Weight:  700.42
Volume:  729.697
LogP:  6.061
LogD:  4.289
LogS:  -5.174
# Rotatable Bonds:  12
TPSA:  131.5
# H-Bond Aceptor:  10
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.159
Synthetic Accessibility Score:  5.645
Fsp3:  0.825
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
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:  -5.262
MDCK Permeability:  6.089680755394511e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.702
30% Bioavailability (F30%):  0.807

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.04
Plasma Protein Binding (PPB):  79.93863677978516%
Volume Distribution (VD):  1.918
Pgp-substrate:  10.267820358276367%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.023
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.55
CYP2C9-inhibitor:  0.223
CYP2C9-substrate:  0.023
CYP2D6-inhibitor:  0.467
CYP2D6-substrate:  0.035
CYP3A4-inhibitor:  0.412
CYP3A4-substrate:  0.78

ADMET: Excretion

Clearance (CL):  2.951
Half-life (T1/2):  0.162

ADMET: Toxicity

hERG Blockers:  0.038
Human Hepatotoxicity (H-HT):  0.385
Drug-inuced Liver Injury (DILI):  0.933
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.292
Maximum Recommended Daily Dose:  0.095
Skin Sensitization:  0.938
Carcinogencity:  0.062
Eye Corrosion:  0.448
Eye Irritation:  0.134
Respiratory Toxicity:  0.946

Download Data

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

  Natural Product: NPC475178

Natural Product ID:  NPC475178
Common Name*:   [(1R,3S,3Ar,5As,5Bs,6S,7Ar,9R,10R,11As,13Ar,13Br)-1,6,9,10-Tetraacetyloxy-5A,8,8,11A,13A-Pentamethyl-3-Propan-2-Yl-1,2,3,4,5,5B,6,7,7A,9,10,11,13,13B-Tetradecahydrocyclopenta[A]Chrysen-3A-Yl]Methyl Acetate
IUPAC Name:   [(1R,3S,3aR,5aS,5bS,6S,7aR,9R,10R,11aS,13aR,13bR)-1,6,9,10-tetraacetyloxy-5a,8,8,11a,13a-pentamethyl-3-propan-2-yl-1,2,3,4,5,5b,6,7,7a,9,10,11,13,13b-tetradecahydrocyclopenta[a]chrysen-3a-yl]methyl acetate
Synonyms:  
Standard InCHIKey:  KAFKWCHAVNDCBL-IIUXYXQJSA-N
Standard InCHI:  InChI=1S/C40H60O10/c1-21(2)28-17-30(48-24(5)43)34-39(12)14-13-27-33(38(39,11)15-16-40(28,34)20-46-22(3)41)29(47-23(4)42)18-32-36(8,9)35(50-26(7)45)31(49-25(6)44)19-37(27,32)10/h13,21,28-35H,14-20H2,1-12H3/t28-,29-,30+,31+,32-,33-,34+,35-,37+,38-,39+,40+/m0/s1
SMILES:  CC(=O)OC[C@]12CC[C@@]3([C@]([C@H]2[C@@H](C[C@H]1C(C)C)OC(=O)C)(C)CC=C1[C@H]3[C@@H](OC(=O)C)C[C@@H]2[C@]1(C)C[C@H]([C@@H](C2(C)C)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL500193
PubChem CID:   21629626
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
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[12350148]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[12762798]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[21044847]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. root n.a. PMID[21973054]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota roots n.a. n.a. PMID[21973054]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16607 Rubia yunnanensis Species Rubiaceae 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
NPT2 Others Unspecified Inhibition = 25.5 % PMID[459535]
NPT2 Others Unspecified Inhibition = 18.7 % PMID[459535]
NPT2 Others Unspecified Inhibition = 9.5 % PMID[459535]
NPT2 Others Unspecified Inhibition = 7.7 % PMID[459535]
NPT2 Others Unspecified Inhibition = 28.4 % PMID[459535]

☑ 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 NPC475178 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
0.9663 High Similarity NPC473678
0.9362 High Similarity NPC155974
0.9255 High Similarity NPC208358
0.9213 High Similarity NPC470612
0.9213 High Similarity NPC470613
0.914 High Similarity NPC253115
0.914 High Similarity NPC304899
0.9043 High Similarity NPC475033
0.9043 High Similarity NPC475032
0.8673 High Similarity NPC476471
0.8673 High Similarity NPC475344
0.86 High Similarity NPC475571
0.8586 High Similarity NPC474124
0.8558 High Similarity NPC144068
0.8544 High Similarity NPC114188
0.85 High Similarity NPC473543
0.8444 Intermediate Similarity NPC473742
0.8416 Intermediate Similarity NPC278628
0.8416 Intermediate Similarity NPC231530
0.84 Intermediate Similarity NPC473523
0.8384 Intermediate Similarity NPC476132
0.8384 Intermediate Similarity NPC475617
0.837 Intermediate Similarity NPC286153
0.8367 Intermediate Similarity NPC102426
0.8367 Intermediate Similarity NPC470068
0.8367 Intermediate Similarity NPC300179
0.83 Intermediate Similarity NPC470053
0.8298 Intermediate Similarity NPC105495
0.8283 Intermediate Similarity NPC476195
0.828 Intermediate Similarity NPC478104
0.8252 Intermediate Similarity NPC295980
0.8252 Intermediate Similarity NPC94529
0.8247 Intermediate Similarity NPC241047
0.8242 Intermediate Similarity NPC139206
0.8242 Intermediate Similarity NPC132386
0.8235 Intermediate Similarity NPC473199
0.8202 Intermediate Similarity NPC44083
0.8202 Intermediate Similarity NPC153987
0.82 Intermediate Similarity NPC289670
0.82 Intermediate Similarity NPC470054
0.8182 Intermediate Similarity NPC247233
0.8182 Intermediate Similarity NPC477875
0.8182 Intermediate Similarity NPC470066
0.8182 Intermediate Similarity NPC477876
0.8182 Intermediate Similarity NPC470067
0.8173 Intermediate Similarity NPC43976
0.8173 Intermediate Similarity NPC51925
0.8173 Intermediate Similarity NPC125361
0.8173 Intermediate Similarity NPC296761
0.8173 Intermediate Similarity NPC154085
0.8172 Intermediate Similarity NPC474970
0.8172 Intermediate Similarity NPC24277
0.8163 Intermediate Similarity NPC169270
0.8163 Intermediate Similarity NPC306797
0.8163 Intermediate Similarity NPC471903
0.8163 Intermediate Similarity NPC276103
0.8163 Intermediate Similarity NPC111834
0.8163 Intermediate Similarity NPC54248
0.8163 Intermediate Similarity NPC292718
0.8155 Intermediate Similarity NPC234160
0.8144 Intermediate Similarity NPC474922
0.8137 Intermediate Similarity NPC152966
0.8132 Intermediate Similarity NPC286786
0.8111 Intermediate Similarity NPC304194
0.81 Intermediate Similarity NPC474571
0.81 Intermediate Similarity NPC473510
0.81 Intermediate Similarity NPC254567
0.81 Intermediate Similarity NPC230546
0.8081 Intermediate Similarity NPC274793
0.8077 Intermediate Similarity NPC472988
0.8077 Intermediate Similarity NPC88701
0.8077 Intermediate Similarity NPC38217
0.8058 Intermediate Similarity NPC242748
0.8039 Intermediate Similarity NPC475623
0.8039 Intermediate Similarity NPC473694
0.8039 Intermediate Similarity NPC471467
0.8039 Intermediate Similarity NPC475334
0.8039 Intermediate Similarity NPC85742
0.8022 Intermediate Similarity NPC195334
0.8022 Intermediate Similarity NPC290495
0.8022 Intermediate Similarity NPC108476
0.802 Intermediate Similarity NPC96784
0.802 Intermediate Similarity NPC235920
0.8019 Intermediate Similarity NPC250481
0.8019 Intermediate Similarity NPC285410
0.8019 Intermediate Similarity NPC470748
0.8019 Intermediate Similarity NPC263827
0.8019 Intermediate Similarity NPC65167
0.8 Intermediate Similarity NPC305835
0.7981 Intermediate Similarity NPC473469
0.7981 Intermediate Similarity NPC473586
0.798 Intermediate Similarity NPC94905
0.798 Intermediate Similarity NPC8954
0.798 Intermediate Similarity NPC88009
0.7961 Intermediate Similarity NPC85593
0.7961 Intermediate Similarity NPC201144
0.7961 Intermediate Similarity NPC181104
0.7961 Intermediate Similarity NPC475331
0.7961 Intermediate Similarity NPC473577
0.7961 Intermediate Similarity NPC80809
0.7961 Intermediate Similarity NPC288502
0.7961 Intermediate Similarity NPC121518
0.7961 Intermediate Similarity NPC475335
0.7961 Intermediate Similarity NPC103298
0.7961 Intermediate Similarity NPC474550
0.7961 Intermediate Similarity NPC31430
0.7961 Intermediate Similarity NPC312774
0.7961 Intermediate Similarity NPC475585
0.7957 Intermediate Similarity NPC239362
0.7957 Intermediate Similarity NPC209802
0.7957 Intermediate Similarity NPC124172
0.7944 Intermediate Similarity NPC280782
0.7941 Intermediate Similarity NPC31085
0.7941 Intermediate Similarity NPC154452
0.7941 Intermediate Similarity NPC136816
0.7941 Intermediate Similarity NPC177701
0.7941 Intermediate Similarity NPC22388
0.7938 Intermediate Similarity NPC234335
0.7938 Intermediate Similarity NPC219516
0.7928 Intermediate Similarity NPC471406
0.7928 Intermediate Similarity NPC475358
0.7928 Intermediate Similarity NPC473566
0.7925 Intermediate Similarity NPC197428
0.7921 Intermediate Similarity NPC7341
0.7921 Intermediate Similarity NPC473200
0.7917 Intermediate Similarity NPC473647
0.7905 Intermediate Similarity NPC475263
0.7905 Intermediate Similarity NPC473517
0.7905 Intermediate Similarity NPC7213
0.7905 Intermediate Similarity NPC258323
0.79 Intermediate Similarity NPC210337
0.789 Intermediate Similarity NPC63609
0.7885 Intermediate Similarity NPC186668
0.7885 Intermediate Similarity NPC477877
0.7885 Intermediate Similarity NPC119855
0.7885 Intermediate Similarity NPC473476
0.7885 Intermediate Similarity NPC470055
0.7885 Intermediate Similarity NPC475290
0.7885 Intermediate Similarity NPC60315
0.7885 Intermediate Similarity NPC473923
0.7885 Intermediate Similarity NPC469874
0.7885 Intermediate Similarity NPC470056
0.7885 Intermediate Similarity NPC220217
0.7879 Intermediate Similarity NPC279974
0.7864 Intermediate Similarity NPC16573
0.7864 Intermediate Similarity NPC160583
0.7864 Intermediate Similarity NPC475701
0.7864 Intermediate Similarity NPC472821
0.7864 Intermediate Similarity NPC473198
0.7857 Intermediate Similarity NPC26046
0.7849 Intermediate Similarity NPC110778
0.7843 Intermediate Similarity NPC160734
0.7843 Intermediate Similarity NPC25177
0.7843 Intermediate Similarity NPC309425
0.7843 Intermediate Similarity NPC295110
0.7843 Intermediate Similarity NPC121072
0.7843 Intermediate Similarity NPC472023
0.7843 Intermediate Similarity NPC49532
0.7843 Intermediate Similarity NPC247701
0.7843 Intermediate Similarity NPC268829
0.7843 Intermediate Similarity NPC4831
0.7843 Intermediate Similarity NPC129372
0.7843 Intermediate Similarity NPC222875
0.7843 Intermediate Similarity NPC144486
0.7843 Intermediate Similarity NPC21064
0.7843 Intermediate Similarity NPC47566
0.7843 Intermediate Similarity NPC88000
0.7838 Intermediate Similarity NPC304260
0.7838 Intermediate Similarity NPC29639
0.7838 Intermediate Similarity NPC44899
0.7838 Intermediate Similarity NPC5883
0.7835 Intermediate Similarity NPC471896
0.7835 Intermediate Similarity NPC123252
0.7835 Intermediate Similarity NPC219937
0.7835 Intermediate Similarity NPC194485
0.7835 Intermediate Similarity NPC53890
0.7822 Intermediate Similarity NPC119036
0.7822 Intermediate Similarity NPC280825
0.7822 Intermediate Similarity NPC234287
0.7822 Intermediate Similarity NPC469725
0.7822 Intermediate Similarity NPC477928
0.7818 Intermediate Similarity NPC203862
0.7818 Intermediate Similarity NPC152615
0.7818 Intermediate Similarity NPC477807
0.7818 Intermediate Similarity NPC93883
0.7812 Intermediate Similarity NPC160304
0.7812 Intermediate Similarity NPC475664
0.7812 Intermediate Similarity NPC473879
0.7812 Intermediate Similarity NPC470542
0.781 Intermediate Similarity NPC470170
0.781 Intermediate Similarity NPC226642
0.781 Intermediate Similarity NPC470169
0.781 Intermediate Similarity NPC475781
0.7802 Intermediate Similarity NPC47808
0.7798 Intermediate Similarity NPC477808
0.7789 Intermediate Similarity NPC264127
0.7789 Intermediate Similarity NPC137306
0.7789 Intermediate Similarity NPC478094
0.7789 Intermediate Similarity NPC84121
0.7788 Intermediate Similarity NPC470062

  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 NPC475178 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
0.7714 Intermediate Similarity NPD6008 Approved
0.7699 Intermediate Similarity NPD8033 Approved
0.7679 Intermediate Similarity NPD7516 Approved
0.7647 Intermediate Similarity NPD7638 Approved
0.7629 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD8294 Approved
0.7611 Intermediate Similarity NPD8377 Approved
0.7589 Intermediate Similarity NPD7328 Approved
0.7589 Intermediate Similarity NPD7327 Approved
0.7573 Intermediate Similarity NPD7640 Approved
0.7573 Intermediate Similarity NPD7639 Approved
0.7551 Intermediate Similarity NPD6051 Approved
0.7544 Intermediate Similarity NPD8296 Approved
0.7544 Intermediate Similarity NPD8380 Approved
0.7544 Intermediate Similarity NPD8335 Approved
0.7544 Intermediate Similarity NPD8379 Approved
0.7544 Intermediate Similarity NPD8378 Approved
0.75 Intermediate Similarity NPD6399 Phase 3
0.7455 Intermediate Similarity NPD8297 Approved
0.7426 Intermediate Similarity NPD7900 Approved
0.7426 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD6409 Approved
0.7423 Intermediate Similarity NPD6684 Approved
0.7423 Intermediate Similarity NPD5330 Approved
0.7423 Intermediate Similarity NPD7334 Approved
0.7423 Intermediate Similarity NPD7146 Approved
0.7423 Intermediate Similarity NPD7521 Approved
0.74 Intermediate Similarity NPD8034 Phase 2
0.74 Intermediate Similarity NPD8035 Phase 2
0.734 Intermediate Similarity NPD7525 Registered
0.7273 Intermediate Similarity NPD6903 Approved
0.7255 Intermediate Similarity NPD7748 Approved
0.7241 Intermediate Similarity NPD7503 Approved
0.7232 Intermediate Similarity NPD4632 Approved
0.7222 Intermediate Similarity NPD6402 Approved
0.7222 Intermediate Similarity NPD5739 Approved
0.7222 Intermediate Similarity NPD7128 Approved
0.7222 Intermediate Similarity NPD6675 Approved
0.7212 Intermediate Similarity NPD7902 Approved
0.7184 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD6372 Approved
0.7182 Intermediate Similarity NPD6373 Approved
0.7167 Intermediate Similarity NPD7736 Approved
0.7156 Intermediate Similarity NPD6412 Phase 2
0.7155 Intermediate Similarity NPD6319 Approved
0.7143 Intermediate Similarity NPD7507 Approved
0.71 Intermediate Similarity NPD6672 Approved
0.71 Intermediate Similarity NPD5737 Approved
0.7097 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6899 Approved
0.7091 Intermediate Similarity NPD7320 Approved
0.7091 Intermediate Similarity NPD6881 Approved
0.7071 Intermediate Similarity NPD6098 Approved
0.7054 Intermediate Similarity NPD6650 Approved
0.7054 Intermediate Similarity NPD8130 Phase 1
0.7054 Intermediate Similarity NPD6649 Approved
0.7043 Intermediate Similarity NPD6009 Approved
0.703 Intermediate Similarity NPD6673 Approved
0.703 Intermediate Similarity NPD6080 Approved
0.703 Intermediate Similarity NPD6904 Approved
0.7027 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5701 Approved
0.7 Intermediate Similarity NPD5697 Approved
0.6991 Remote Similarity NPD6882 Approved
0.6989 Remote Similarity NPD6942 Approved
0.6989 Remote Similarity NPD7339 Approved
0.6975 Remote Similarity NPD7604 Phase 2
0.697 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6967 Remote Similarity NPD7319 Approved
0.6964 Remote Similarity NPD7102 Approved
0.6964 Remote Similarity NPD6883 Approved
0.6964 Remote Similarity NPD7290 Approved
0.6949 Remote Similarity NPD5983 Phase 2
0.6944 Remote Similarity NPD7632 Discontinued
0.6942 Remote Similarity NPD8293 Discontinued
0.6937 Remote Similarity NPD6011 Approved
0.693 Remote Similarity NPD8133 Approved
0.6917 Remote Similarity NPD7492 Approved
0.6903 Remote Similarity NPD6847 Approved
0.6903 Remote Similarity NPD6617 Approved
0.6903 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6903 Remote Similarity NPD6869 Approved
0.6893 Remote Similarity NPD7515 Phase 2
0.6887 Remote Similarity NPD6083 Phase 2
0.6887 Remote Similarity NPD6084 Phase 2
0.6875 Remote Similarity NPD6012 Approved
0.6875 Remote Similarity NPD6014 Approved
0.6875 Remote Similarity NPD7645 Phase 2
0.6875 Remote Similarity NPD6013 Approved
0.6869 Remote Similarity NPD4786 Approved
0.6864 Remote Similarity NPD6054 Approved
0.6864 Remote Similarity NPD6059 Approved
0.686 Remote Similarity NPD6616 Approved
0.686 Remote Similarity NPD6336 Discontinued
0.6847 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6832 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6832 Remote Similarity NPD7524 Approved
0.6827 Remote Similarity NPD4202 Approved
0.6803 Remote Similarity NPD7078 Approved
0.6765 Remote Similarity NPD5208 Approved
0.6762 Remote Similarity NPD6001 Approved
0.6752 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6752 Remote Similarity NPD7115 Discovery
0.675 Remote Similarity NPD6370 Approved
0.6731 Remote Similarity NPD6050 Approved
0.6731 Remote Similarity NPD5693 Phase 1
0.6729 Remote Similarity NPD4755 Approved
0.6702 Remote Similarity NPD4784 Approved
0.6702 Remote Similarity NPD4785 Approved
0.67 Remote Similarity NPD7338 Clinical (unspecified phase)
0.67 Remote Similarity NPD3668 Phase 3
0.6699 Remote Similarity NPD5328 Approved
0.6698 Remote Similarity NPD5695 Phase 3
0.6694 Remote Similarity NPD8328 Phase 3
0.6667 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6016 Approved
0.6667 Remote Similarity NPD3667 Approved
0.6667 Remote Similarity NPD4243 Approved
0.6667 Remote Similarity NPD5696 Approved
0.6667 Remote Similarity NPD6015 Approved
0.6635 Remote Similarity NPD5692 Phase 3
0.6612 Remote Similarity NPD5988 Approved
0.6606 Remote Similarity NPD4700 Approved
0.6606 Remote Similarity NPD5286 Approved
0.6606 Remote Similarity NPD4696 Approved
0.6606 Remote Similarity NPD5285 Approved
0.66 Remote Similarity NPD6695 Phase 3
0.6579 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6571 Remote Similarity NPD6079 Approved
0.6571 Remote Similarity NPD5694 Approved
0.6571 Remote Similarity NPD7637 Suspended
0.6569 Remote Similarity NPD3618 Phase 1
0.6557 Remote Similarity NPD6067 Discontinued
0.6555 Remote Similarity NPD6335 Approved
0.6545 Remote Similarity NPD5223 Approved
0.6535 Remote Similarity NPD3666 Approved
0.6535 Remote Similarity NPD3133 Approved
0.6535 Remote Similarity NPD3665 Phase 1
0.6531 Remote Similarity NPD4195 Approved
0.6525 Remote Similarity NPD6274 Approved
0.6522 Remote Similarity NPD4634 Approved
0.6514 Remote Similarity NPD4225 Approved
0.6509 Remote Similarity NPD8171 Discontinued
0.6505 Remote Similarity NPD3573 Approved
0.6505 Remote Similarity NPD7750 Discontinued
0.65 Remote Similarity NPD7101 Approved
0.65 Remote Similarity NPD7100 Approved
0.6491 Remote Similarity NPD6686 Approved
0.6486 Remote Similarity NPD4633 Approved
0.6486 Remote Similarity NPD5224 Approved
0.6486 Remote Similarity NPD5225 Approved
0.6486 Remote Similarity NPD5226 Approved
0.6486 Remote Similarity NPD5211 Phase 2
0.648 Remote Similarity NPD6033 Approved
0.6476 Remote Similarity NPD5207 Approved
0.6471 Remote Similarity NPD6317 Approved
0.6465 Remote Similarity NPD6928 Phase 2
0.6465 Remote Similarity NPD4748 Discontinued
0.646 Remote Similarity NPD4767 Approved
0.646 Remote Similarity NPD4768 Approved
0.6455 Remote Similarity NPD6648 Approved
0.6449 Remote Similarity NPD5707 Approved
0.6429 Remote Similarity NPD6115 Approved
0.6429 Remote Similarity NPD5175 Approved
0.6429 Remote Similarity NPD5174 Approved
0.6429 Remote Similarity NPD4754 Approved
0.6429 Remote Similarity NPD6697 Approved
0.6429 Remote Similarity NPD6118 Approved
0.6429 Remote Similarity NPD6114 Approved
0.6417 Remote Similarity NPD6313 Approved
0.6417 Remote Similarity NPD6314 Approved
0.6415 Remote Similarity NPD5281 Approved
0.6415 Remote Similarity NPD5284 Approved
0.641 Remote Similarity NPD6053 Discontinued
0.6396 Remote Similarity NPD5344 Discontinued
0.6393 Remote Similarity NPD6909 Approved
0.6393 Remote Similarity NPD6908 Approved
0.6392 Remote Similarity NPD6933 Approved
0.6381 Remote Similarity NPD4753 Phase 2
0.6372 Remote Similarity NPD5141 Approved
0.6364 Remote Similarity NPD6929 Approved
0.6354 Remote Similarity NPD6926 Approved
0.6354 Remote Similarity NPD6924 Approved
0.6348 Remote Similarity NPD4729 Approved
0.6348 Remote Similarity NPD4730 Approved
0.6337 Remote Similarity NPD4221 Approved
0.6337 Remote Similarity NPD4223 Phase 3
0.633 Remote Similarity NPD5221 Approved
0.633 Remote Similarity NPD5220 Clinical (unspecified phase)
0.633 Remote Similarity NPD5222 Approved
0.633 Remote Similarity NPD4697 Phase 3
0.6327 Remote Similarity NPD6116 Phase 1
0.6316 Remote Similarity NPD5777 Approved
0.6311 Remote Similarity NPD5329 Approved
0.63 Remote Similarity NPD6931 Approved
0.63 Remote Similarity NPD6930 Phase 2
0.6289 Remote Similarity NPD4190 Phase 3
0.6289 Remote Similarity NPD5275 Approved
0.6283 Remote Similarity NPD6052 Approved
0.6279 Remote Similarity NPD8449 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