Structure

Physi-Chem Properties

Molecular Weight:  642.41
Volume:  680.161
LogP:  6.515
LogD:  4.582
LogS:  -5.624
# Rotatable Bonds:  10
TPSA:  105.2
# H-Bond Aceptor:  8
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.17
Synthetic Accessibility Score:  5.422
Fsp3:  0.842
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:  -5.127
MDCK Permeability:  3.869319334626198e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.741
30% Bioavailability (F30%):  0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.133
Plasma Protein Binding (PPB):  84.66034698486328%
Volume Distribution (VD):  1.699
Pgp-substrate:  8.919426918029785%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.03
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.772
CYP2C9-inhibitor:  0.21
CYP2C9-substrate:  0.023
CYP2D6-inhibitor:  0.04
CYP2D6-substrate:  0.037
CYP3A4-inhibitor:  0.572
CYP3A4-substrate:  0.795

ADMET: Excretion

Clearance (CL):  3.225
Half-life (T1/2):  0.045

ADMET: Toxicity

hERG Blockers:  0.132
Human Hepatotoxicity (H-HT):  0.295
Drug-inuced Liver Injury (DILI):  0.89
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.352
Maximum Recommended Daily Dose:  0.449
Skin Sensitization:  0.941
Carcinogencity:  0.126
Eye Corrosion:  0.704
Eye Irritation:  0.101
Respiratory Toxicity:  0.964

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

  Natural Product: NPC473678

Natural Product ID:  NPC473678
Common Name*:   [(1R,3S,3Ar,5As,5Bs,6S,7Ar,9S,11As,13Ar,13Br)-1,6,9-Triacetyloxy-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,9S,11aS,13aR,13bR)-1,6,9-triacetyloxy-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:  UHCYBXRFSQMBQD-YUUUWBKSSA-N
Standard InCHI:  InChI=1S/C38H58O8/c1-21(2)27-18-29(45-24(5)41)33-37(11)15-12-26-32(36(37,10)16-17-38(27,33)20-43-22(3)39)28(44-23(4)40)19-30-34(7,8)31(46-25(6)42)13-14-35(26,30)9/h12,21,27-33H,13-20H2,1-11H3/t27-,28-,29+,30-,31-,32-,33+,35+,36-,37+,38+/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)CC[C@@H](C2(C)C)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL448937
PubChem CID:   21629624
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 = 0.0 % PMID[501535]
NPT2 Others Unspecified Inhibition = -1.2 % PMID[501535]
NPT2 Others Unspecified Inhibition = 10.6 % PMID[501535]
NPT2 Others Unspecified Inhibition = 5.3 % PMID[501535]
NPT2 Others Unspecified Inhibition = 6.6 % PMID[501535]

☑ 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 NPC473678 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 NPC475178
0.9535 High Similarity NPC470612
0.9535 High Similarity NPC470613
0.9444 High Similarity NPC253115
0.9444 High Similarity NPC304899
0.914 High Similarity NPC208358
0.9043 High Similarity NPC155974
0.8866 High Similarity NPC475571
0.8736 High Similarity NPC473742
0.8723 High Similarity NPC475032
0.8723 High Similarity NPC475033
0.8673 High Similarity NPC278628
0.8673 High Similarity NPC231530
0.8652 High Similarity NPC286153
0.8556 High Similarity NPC478104
0.8523 High Similarity NPC132386
0.8523 High Similarity NPC139206
0.85 High Similarity NPC94529
0.8488 Intermediate Similarity NPC44083
0.8488 Intermediate Similarity NPC153987
0.8444 Intermediate Similarity NPC24277
0.8444 Intermediate Similarity NPC474970
0.8431 Intermediate Similarity NPC114188
0.8421 Intermediate Similarity NPC54248
0.8421 Intermediate Similarity NPC276103
0.8409 Intermediate Similarity NPC286786
0.8404 Intermediate Similarity NPC474922
0.8391 Intermediate Similarity NPC304194
0.8367 Intermediate Similarity NPC476471
0.8367 Intermediate Similarity NPC475344
0.8295 Intermediate Similarity NPC195334
0.8295 Intermediate Similarity NPC108476
0.8295 Intermediate Similarity NPC290495
0.8283 Intermediate Similarity NPC474124
0.8283 Intermediate Similarity NPC85742
0.8276 Intermediate Similarity NPC305835
0.8269 Intermediate Similarity NPC144068
0.8247 Intermediate Similarity NPC470068
0.8229 Intermediate Similarity NPC8954
0.8229 Intermediate Similarity NPC94905
0.8222 Intermediate Similarity NPC124172
0.8222 Intermediate Similarity NPC209802
0.82 Intermediate Similarity NPC473543
0.8191 Intermediate Similarity NPC234335
0.8182 Intermediate Similarity NPC470053
0.8182 Intermediate Similarity NPC22388
0.8172 Intermediate Similarity NPC105495
0.8172 Intermediate Similarity NPC473647
0.8155 Intermediate Similarity NPC197428
0.8137 Intermediate Similarity NPC295980
0.8125 Intermediate Similarity NPC279974
0.8119 Intermediate Similarity NPC119855
0.8119 Intermediate Similarity NPC473199
0.8119 Intermediate Similarity NPC220217
0.8111 Intermediate Similarity NPC110778
0.8105 Intermediate Similarity NPC26046
0.81 Intermediate Similarity NPC160583
0.81 Intermediate Similarity NPC473523
0.8085 Intermediate Similarity NPC194485
0.8085 Intermediate Similarity NPC53890
0.8085 Intermediate Similarity NPC123252
0.8085 Intermediate Similarity NPC219937
0.8085 Intermediate Similarity NPC471896
0.8081 Intermediate Similarity NPC470054
0.8081 Intermediate Similarity NPC295110
0.8081 Intermediate Similarity NPC25177
0.8081 Intermediate Similarity NPC476132
0.8081 Intermediate Similarity NPC222875
0.8081 Intermediate Similarity NPC268829
0.8081 Intermediate Similarity NPC475617
0.8081 Intermediate Similarity NPC247701
0.8068 Intermediate Similarity NPC47808
0.8065 Intermediate Similarity NPC473879
0.8065 Intermediate Similarity NPC470542
0.8065 Intermediate Similarity NPC160304
0.8061 Intermediate Similarity NPC119036
0.8061 Intermediate Similarity NPC102426
0.8061 Intermediate Similarity NPC470067
0.8061 Intermediate Similarity NPC470066
0.8061 Intermediate Similarity NPC300179
0.8043 Intermediate Similarity NPC264127
0.8043 Intermediate Similarity NPC137306
0.8043 Intermediate Similarity NPC84121
0.8041 Intermediate Similarity NPC471903
0.8039 Intermediate Similarity NPC475781
0.8039 Intermediate Similarity NPC234160
0.8022 Intermediate Similarity NPC299963
0.8022 Intermediate Similarity NPC475798
0.8022 Intermediate Similarity NPC127606
0.8021 Intermediate Similarity NPC3359
0.8 Intermediate Similarity NPC26888
0.8 Intermediate Similarity NPC1272
0.8 Intermediate Similarity NPC470614
0.8 Intermediate Similarity NPC177641
0.8 Intermediate Similarity NPC130840
0.8 Intermediate Similarity NPC472504
0.798 Intermediate Similarity NPC477972
0.798 Intermediate Similarity NPC20113
0.798 Intermediate Similarity NPC477968
0.798 Intermediate Similarity NPC476195
0.798 Intermediate Similarity NPC477971
0.798 Intermediate Similarity NPC228251
0.798 Intermediate Similarity NPC219285
0.798 Intermediate Similarity NPC161527
0.7978 Intermediate Similarity NPC269791
0.7961 Intermediate Similarity NPC38217
0.7961 Intermediate Similarity NPC472988
0.7959 Intermediate Similarity NPC177818
0.7959 Intermediate Similarity NPC190554
0.7957 Intermediate Similarity NPC46912
0.7957 Intermediate Similarity NPC162107
0.7941 Intermediate Similarity NPC242748
0.7938 Intermediate Similarity NPC69548
0.7938 Intermediate Similarity NPC474727
0.7938 Intermediate Similarity NPC281134
0.7938 Intermediate Similarity NPC184848
0.7938 Intermediate Similarity NPC241047
0.7935 Intermediate Similarity NPC191965
0.7935 Intermediate Similarity NPC98270
0.7925 Intermediate Similarity NPC202889
0.7921 Intermediate Similarity NPC10232
0.7921 Intermediate Similarity NPC196471
0.7921 Intermediate Similarity NPC475623
0.7921 Intermediate Similarity NPC189588
0.7921 Intermediate Similarity NPC475334
0.7921 Intermediate Similarity NPC473694
0.7921 Intermediate Similarity NPC187302
0.7921 Intermediate Similarity NPC472821
0.7921 Intermediate Similarity NPC97487
0.7921 Intermediate Similarity NPC140723
0.7917 Intermediate Similarity NPC470375
0.7917 Intermediate Similarity NPC242419
0.7917 Intermediate Similarity NPC470376
0.7917 Intermediate Similarity NPC235126
0.7917 Intermediate Similarity NPC38232
0.7912 Intermediate Similarity NPC193870
0.7912 Intermediate Similarity NPC477818
0.7912 Intermediate Similarity NPC141941
0.7912 Intermediate Similarity NPC5280
0.7905 Intermediate Similarity NPC470748
0.79 Intermediate Similarity NPC474022
0.79 Intermediate Similarity NPC289670
0.7895 Intermediate Similarity NPC148414
0.7895 Intermediate Similarity NPC111585
0.7895 Intermediate Similarity NPC175628
0.7895 Intermediate Similarity NPC10274
0.7885 Intermediate Similarity NPC43976
0.7885 Intermediate Similarity NPC296761
0.7885 Intermediate Similarity NPC125361
0.7885 Intermediate Similarity NPC154085
0.7885 Intermediate Similarity NPC51925
0.7879 Intermediate Similarity NPC260149
0.7879 Intermediate Similarity NPC477813
0.7879 Intermediate Similarity NPC58942
0.7879 Intermediate Similarity NPC477875
0.7879 Intermediate Similarity NPC477854
0.7879 Intermediate Similarity NPC247233
0.7879 Intermediate Similarity NPC477876
0.7872 Intermediate Similarity NPC97884
0.7872 Intermediate Similarity NPC472220
0.7864 Intermediate Similarity NPC473469
0.7857 Intermediate Similarity NPC173272
0.7857 Intermediate Similarity NPC299654
0.7857 Intermediate Similarity NPC306797
0.7857 Intermediate Similarity NPC111834
0.7857 Intermediate Similarity NPC169270
0.7857 Intermediate Similarity NPC42042
0.7857 Intermediate Similarity NPC292718
0.7849 Intermediate Similarity NPC10005
0.7849 Intermediate Similarity NPC91525
0.7849 Intermediate Similarity NPC9892
0.7849 Intermediate Similarity NPC201273
0.7849 Intermediate Similarity NPC168231
0.7849 Intermediate Similarity NPC102996
0.7849 Intermediate Similarity NPC329943
0.7843 Intermediate Similarity NPC121518
0.7843 Intermediate Similarity NPC181104
0.7843 Intermediate Similarity NPC29705
0.7843 Intermediate Similarity NPC473577
0.7843 Intermediate Similarity NPC80809
0.7843 Intermediate Similarity NPC475331
0.7843 Intermediate Similarity NPC85593
0.7843 Intermediate Similarity NPC474550
0.7843 Intermediate Similarity NPC152966
0.7843 Intermediate Similarity NPC475585
0.7843 Intermediate Similarity NPC288502
0.7843 Intermediate Similarity NPC201144
0.7843 Intermediate Similarity NPC475335
0.7843 Intermediate Similarity NPC103298
0.7843 Intermediate Similarity NPC31430
0.7835 Intermediate Similarity NPC304968
0.7835 Intermediate Similarity NPC128488
0.783 Intermediate Similarity NPC280782
0.7826 Intermediate Similarity NPC239362
0.7826 Intermediate Similarity NPC475509
0.7822 Intermediate Similarity NPC154452
0.7822 Intermediate Similarity NPC136816
0.7812 Intermediate Similarity NPC77099
0.7812 Intermediate Similarity NPC285184
0.7812 Intermediate Similarity NPC219516

  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 NPC473678 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
0.7941 Intermediate Similarity NPD6008 Approved
0.7879 Intermediate Similarity NPD7638 Approved
0.7872 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.78 Intermediate Similarity NPD7640 Approved
0.78 Intermediate Similarity NPD7639 Approved
0.7789 Intermediate Similarity NPD6051 Approved
0.7732 Intermediate Similarity NPD6399 Phase 3
0.766 Intermediate Similarity NPD7334 Approved
0.766 Intermediate Similarity NPD6409 Approved
0.766 Intermediate Similarity NPD5330 Approved
0.766 Intermediate Similarity NPD7146 Approved
0.766 Intermediate Similarity NPD6684 Approved
0.766 Intermediate Similarity NPD7521 Approved
0.7653 Intermediate Similarity NPD7900 Approved
0.7653 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7629 Intermediate Similarity NPD8035 Phase 2
0.7629 Intermediate Similarity NPD8034 Phase 2
0.7589 Intermediate Similarity NPD8033 Approved
0.7582 Intermediate Similarity NPD7525 Registered
0.75 Intermediate Similarity NPD6903 Approved
0.75 Intermediate Similarity NPD8294 Approved
0.75 Intermediate Similarity NPD8377 Approved
0.7477 Intermediate Similarity NPD7328 Approved
0.7477 Intermediate Similarity NPD7327 Approved
0.7475 Intermediate Similarity NPD7748 Approved
0.7434 Intermediate Similarity NPD8380 Approved
0.7434 Intermediate Similarity NPD8335 Approved
0.7434 Intermediate Similarity NPD8379 Approved
0.7434 Intermediate Similarity NPD8296 Approved
0.7434 Intermediate Similarity NPD8378 Approved
0.7429 Intermediate Similarity NPD6675 Approved
0.7429 Intermediate Similarity NPD7128 Approved
0.7429 Intermediate Similarity NPD6402 Approved
0.7429 Intermediate Similarity NPD5739 Approved
0.7426 Intermediate Similarity NPD7902 Approved
0.7411 Intermediate Similarity NPD7516 Approved
0.74 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD6373 Approved
0.7383 Intermediate Similarity NPD6372 Approved
0.7339 Intermediate Similarity NPD8297 Approved
0.7333 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD6672 Approved
0.732 Intermediate Similarity NPD5737 Approved
0.7292 Intermediate Similarity NPD6098 Approved
0.729 Intermediate Similarity NPD6881 Approved
0.729 Intermediate Similarity NPD7320 Approved
0.729 Intermediate Similarity NPD6899 Approved
0.7248 Intermediate Similarity NPD6649 Approved
0.7248 Intermediate Similarity NPD8130 Phase 1
0.7248 Intermediate Similarity NPD6650 Approved
0.7245 Intermediate Similarity NPD6904 Approved
0.7245 Intermediate Similarity NPD6673 Approved
0.7245 Intermediate Similarity NPD6080 Approved
0.7222 Intermediate Similarity NPD6942 Approved
0.7222 Intermediate Similarity NPD7339 Approved
0.7196 Intermediate Similarity NPD5697 Approved
0.7196 Intermediate Similarity NPD5701 Approved
0.7188 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD6882 Approved
0.7156 Intermediate Similarity NPD6883 Approved
0.7156 Intermediate Similarity NPD7290 Approved
0.7156 Intermediate Similarity NPD7102 Approved
0.7143 Intermediate Similarity NPD7632 Discontinued
0.713 Intermediate Similarity NPD7503 Approved
0.713 Intermediate Similarity NPD6011 Approved
0.7117 Intermediate Similarity NPD4632 Approved
0.71 Intermediate Similarity NPD7515 Phase 2
0.7097 Intermediate Similarity NPD7645 Phase 2
0.7091 Intermediate Similarity NPD6869 Approved
0.7091 Intermediate Similarity NPD6847 Approved
0.7091 Intermediate Similarity NPD6617 Approved
0.7091 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD6084 Phase 2
0.7087 Intermediate Similarity NPD6083 Phase 2
0.7083 Intermediate Similarity NPD4786 Approved
0.7064 Intermediate Similarity NPD6012 Approved
0.7064 Intermediate Similarity NPD6014 Approved
0.7064 Intermediate Similarity NPD6013 Approved
0.7059 Intermediate Similarity NPD7736 Approved
0.7043 Intermediate Similarity NPD6319 Approved
0.7041 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6412 Phase 2
0.7034 Intermediate Similarity NPD7507 Approved
0.703 Intermediate Similarity NPD4202 Approved
0.697 Remote Similarity NPD5208 Approved
0.6961 Remote Similarity NPD6001 Approved
0.6931 Remote Similarity NPD5693 Phase 1
0.6931 Remote Similarity NPD6050 Approved
0.693 Remote Similarity NPD6009 Approved
0.6923 Remote Similarity NPD4785 Approved
0.6923 Remote Similarity NPD4755 Approved
0.6923 Remote Similarity NPD4784 Approved
0.6907 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6907 Remote Similarity NPD3668 Phase 3
0.69 Remote Similarity NPD5328 Approved
0.6893 Remote Similarity NPD5695 Phase 3
0.6889 Remote Similarity NPD4243 Approved
0.6875 Remote Similarity NPD3667 Approved
0.6864 Remote Similarity NPD7604 Phase 2
0.686 Remote Similarity NPD7319 Approved
0.6857 Remote Similarity NPD5696 Approved
0.6838 Remote Similarity NPD5983 Phase 2
0.6833 Remote Similarity NPD8293 Discontinued
0.6832 Remote Similarity NPD5692 Phase 3
0.6814 Remote Similarity NPD8133 Approved
0.6807 Remote Similarity NPD7492 Approved
0.6804 Remote Similarity NPD6695 Phase 3
0.6792 Remote Similarity NPD5286 Approved
0.6792 Remote Similarity NPD5285 Approved
0.6792 Remote Similarity NPD4700 Approved
0.6792 Remote Similarity NPD4696 Approved
0.6768 Remote Similarity NPD3618 Phase 1
0.6765 Remote Similarity NPD6079 Approved
0.6765 Remote Similarity NPD7637 Suspended
0.6765 Remote Similarity NPD5694 Approved
0.6757 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6752 Remote Similarity NPD6059 Approved
0.6752 Remote Similarity NPD6054 Approved
0.675 Remote Similarity NPD6616 Approved
0.675 Remote Similarity NPD6336 Discontinued
0.6737 Remote Similarity NPD4195 Approved
0.6735 Remote Similarity NPD3665 Phase 1
0.6735 Remote Similarity NPD3666 Approved
0.6735 Remote Similarity NPD3133 Approved
0.6729 Remote Similarity NPD5223 Approved
0.6724 Remote Similarity NPD6335 Approved
0.67 Remote Similarity NPD7750 Discontinued
0.67 Remote Similarity NPD3573 Approved
0.6696 Remote Similarity NPD6274 Approved
0.6694 Remote Similarity NPD7078 Approved
0.6667 Remote Similarity NPD7100 Approved
0.6667 Remote Similarity NPD5225 Approved
0.6667 Remote Similarity NPD5224 Approved
0.6667 Remote Similarity NPD5211 Phase 2
0.6667 Remote Similarity NPD4633 Approved
0.6667 Remote Similarity NPD5207 Approved
0.6667 Remote Similarity NPD5226 Approved
0.6667 Remote Similarity NPD7101 Approved
0.6667 Remote Similarity NPD6928 Phase 2
0.6667 Remote Similarity NPD4748 Discontinued
0.6639 Remote Similarity NPD6370 Approved
0.6638 Remote Similarity NPD7115 Discovery
0.6638 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6638 Remote Similarity NPD6317 Approved
0.6636 Remote Similarity NPD4768 Approved
0.6636 Remote Similarity NPD4767 Approved
0.6635 Remote Similarity NPD5707 Approved
0.6632 Remote Similarity NPD6114 Approved
0.6632 Remote Similarity NPD6115 Approved
0.6632 Remote Similarity NPD6697 Approved
0.6632 Remote Similarity NPD6118 Approved
0.6606 Remote Similarity NPD5175 Approved
0.6606 Remote Similarity NPD5174 Approved
0.6606 Remote Similarity NPD4754 Approved
0.6602 Remote Similarity NPD5281 Approved
0.6602 Remote Similarity NPD5284 Approved
0.6583 Remote Similarity NPD8328 Phase 3
0.6581 Remote Similarity NPD6314 Approved
0.6581 Remote Similarity NPD6313 Approved
0.6579 Remote Similarity NPD6053 Discontinued
0.6577 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6569 Remote Similarity NPD4753 Phase 2
0.6562 Remote Similarity NPD6929 Approved
0.6559 Remote Similarity NPD6926 Approved
0.6559 Remote Similarity NPD6924 Approved
0.6555 Remote Similarity NPD6015 Approved
0.6555 Remote Similarity NPD6016 Approved
0.6555 Remote Similarity NPD6908 Approved
0.6555 Remote Similarity NPD6909 Approved
0.6549 Remote Similarity NPD4634 Approved
0.6545 Remote Similarity NPD5141 Approved
0.6535 Remote Similarity NPD7524 Approved
0.6531 Remote Similarity NPD4221 Approved
0.6531 Remote Similarity NPD4223 Phase 3
0.6526 Remote Similarity NPD6116 Phase 1
0.6522 Remote Similarity NPD5777 Approved
0.6518 Remote Similarity NPD4729 Approved
0.6518 Remote Similarity NPD4730 Approved
0.6509 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6509 Remote Similarity NPD5221 Approved
0.6509 Remote Similarity NPD5222 Approved
0.6509 Remote Similarity NPD4697 Phase 3
0.65 Remote Similarity NPD5329 Approved
0.65 Remote Similarity NPD5988 Approved
0.6495 Remote Similarity NPD6931 Approved
0.6495 Remote Similarity NPD6930 Phase 2
0.6489 Remote Similarity NPD5275 Approved
0.6489 Remote Similarity NPD4190 Phase 3
0.6455 Remote Similarity NPD6052 Approved
0.6449 Remote Similarity NPD5173 Approved
0.6446 Remote Similarity NPD6067 Discontinued
0.6421 Remote Similarity NPD6933 Approved
0.6421 Remote Similarity NPD6117 Approved
0.6417 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6415 Remote Similarity NPD5654 Approved
0.641 Remote Similarity NPD6868 Approved
0.6404 Remote Similarity NPD5248 Approved
0.6404 Remote Similarity NPD5251 Approved
0.6404 Remote Similarity NPD5247 Approved
0.6404 Remote Similarity NPD5249 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