Structure

Physi-Chem Properties

Molecular Weight:  656.39
Volume:  686.315
LogP:  5.399
LogD:  4.067
LogS:  -5.146
# Rotatable Bonds:  10
TPSA:  122.27
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.182
Synthetic Accessibility Score:  5.582
Fsp3:  0.816
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:  -5.257
MDCK Permeability:  5.0038917834172025e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.879
30% Bioavailability (F30%):  0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.182
Plasma Protein Binding (PPB):  82.73175811767578%
Volume Distribution (VD):  1.791
Pgp-substrate:  9.219338417053223%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.049
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.844
CYP2C9-inhibitor:  0.219
CYP2C9-substrate:  0.028
CYP2D6-inhibitor:  0.021
CYP2D6-substrate:  0.032
CYP3A4-inhibitor:  0.617
CYP3A4-substrate:  0.857

ADMET: Excretion

Clearance (CL):  3.797
Half-life (T1/2):  0.163

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.622
Drug-inuced Liver Injury (DILI):  0.874
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.921
Maximum Recommended Daily Dose:  0.652
Skin Sensitization:  0.29
Carcinogencity:  0.214
Eye Corrosion:  0.388
Eye Irritation:  0.122
Respiratory Toxicity:  0.977

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

  Natural Product: NPC475571

Natural Product ID:  NPC475571
Common Name*:   [(1R,3S,3Ar,5As,5Bs,6S,7Ar,10R,11As,13Ar,13Br)-1,6,10-Triacetyloxy-5A,8,8,11A,13A-Pentamethyl-9-Oxo-3-Propan-2-Yl-2,3,4,5,5B,6,7,7A,10,11,13,13B-Dodecahydro-1H-Cyclopenta[A]Chrysen-3A-Yl]Methyl Acetate
IUPAC Name:   [(1R,3S,3aR,5aS,5bS,6S,7aR,10R,11aS,13aR,13bR)-1,6,10-triacetyloxy-5a,8,8,11a,13a-pentamethyl-9-oxo-3-propan-2-yl-2,3,4,5,5b,6,7,7a,10,11,13,13b-dodecahydro-1H-cyclopenta[a]chrysen-3a-yl]methyl acetate
Synonyms:  
Standard InCHIKey:  VKJBSRVGGWUBNP-HOWSTPSFSA-N
Standard InCHI:  InChI=1S/C38H56O9/c1-20(2)26-16-28(46-23(5)41)32-37(11)13-12-25-31(36(37,10)14-15-38(26,32)19-44-21(3)39)27(45-22(4)40)17-30-34(7,8)33(43)29(47-24(6)42)18-35(25,30)9/h12,20,26-32H,13-19H2,1-11H3/t26-,27-,28+,29+,30-,31-,32+,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)C[C@H](C(=O)C2(C)C)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL508448
PubChem CID:   21629621
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 roots n.a. n.a. PMID[21973054]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. root 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 = 18.7 % PMID[505108]
NPT2 Others Unspecified Inhibition = 12.5 % PMID[505108]
NPT2 Others Unspecified Inhibition = 7.3 % PMID[505108]
NPT2 Others Unspecified Inhibition = 1.7 % PMID[505108]
NPT2 Others Unspecified Inhibition = 23.0 % PMID[505108]

☑ 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 NPC475571 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
0.9406 High Similarity NPC94529
0.9208 High Similarity NPC278628
0.9208 High Similarity NPC231530
0.8962 High Similarity NPC202889
0.8866 High Similarity NPC473678
0.8846 High Similarity NPC470269
0.8796 High Similarity NPC270958
0.8738 High Similarity NPC29705
0.8713 High Similarity NPC15390
0.8692 High Similarity NPC280782
0.8679 High Similarity NPC197428
0.8654 High Similarity NPC196528
0.8636 High Similarity NPC118638
0.86 High Similarity NPC475178
0.8544 High Similarity NPC271266
0.8544 High Similarity NPC308351
0.8519 High Similarity NPC71348
0.8519 High Similarity NPC170487
0.8515 High Similarity NPC190554
0.8462 Intermediate Similarity NPC140723
0.8454 Intermediate Similarity NPC470613
0.8454 Intermediate Similarity NPC470612
0.8426 Intermediate Similarity NPC118860
0.8426 Intermediate Similarity NPC231589
0.8426 Intermediate Similarity NPC214797
0.8426 Intermediate Similarity NPC470281
0.8416 Intermediate Similarity NPC253115
0.8416 Intermediate Similarity NPC42042
0.8416 Intermediate Similarity NPC304899
0.8365 Intermediate Similarity NPC22388
0.8302 Intermediate Similarity NPC50535
0.8302 Intermediate Similarity NPC470267
0.8286 Intermediate Similarity NPC469985
0.8273 Intermediate Similarity NPC194100
0.8273 Intermediate Similarity NPC472926
0.8273 Intermediate Similarity NPC52634
0.8261 Intermediate Similarity NPC267822
0.8252 Intermediate Similarity NPC260149
0.8252 Intermediate Similarity NPC271387
0.8252 Intermediate Similarity NPC58942
0.8252 Intermediate Similarity NPC477854
0.8252 Intermediate Similarity NPC176845
0.8252 Intermediate Similarity NPC153792
0.8241 Intermediate Similarity NPC258543
0.8241 Intermediate Similarity NPC241927
0.8235 Intermediate Similarity NPC173272
0.8235 Intermediate Similarity NPC58052
0.8235 Intermediate Similarity NPC111684
0.8224 Intermediate Similarity NPC44063
0.8224 Intermediate Similarity NPC86852
0.8224 Intermediate Similarity NPC251824
0.8208 Intermediate Similarity NPC310586
0.8208 Intermediate Similarity NPC47281
0.819 Intermediate Similarity NPC169818
0.8182 Intermediate Similarity NPC474679
0.8174 Intermediate Similarity NPC65858
0.8173 Intermediate Similarity NPC218383
0.8173 Intermediate Similarity NPC83709
0.8173 Intermediate Similarity NPC208358
0.8158 Intermediate Similarity NPC471406
0.8155 Intermediate Similarity NPC23680
0.8148 Intermediate Similarity NPC211224
0.8142 Intermediate Similarity NPC324253
0.8137 Intermediate Similarity NPC48330
0.8137 Intermediate Similarity NPC469599
0.8137 Intermediate Similarity NPC279974
0.8131 Intermediate Similarity NPC28791
0.8131 Intermediate Similarity NPC181265
0.8113 Intermediate Similarity NPC254202
0.8108 Intermediate Similarity NPC962
0.8103 Intermediate Similarity NPC43252
0.8103 Intermediate Similarity NPC135038
0.81 Intermediate Similarity NPC471896
0.8095 Intermediate Similarity NPC155974
0.8091 Intermediate Similarity NPC43775
0.8077 Intermediate Similarity NPC119036
0.8077 Intermediate Similarity NPC275439
0.8077 Intermediate Similarity NPC112753
0.8073 Intermediate Similarity NPC2766
0.8073 Intermediate Similarity NPC304495
0.8061 Intermediate Similarity NPC264127
0.8058 Intermediate Similarity NPC477853
0.8053 Intermediate Similarity NPC472927
0.8037 Intermediate Similarity NPC96268
0.8037 Intermediate Similarity NPC137657
0.8037 Intermediate Similarity NPC235889
0.8036 Intermediate Similarity NPC18547
0.8036 Intermediate Similarity NPC474906
0.8036 Intermediate Similarity NPC473798
0.802 Intermediate Similarity NPC470230
0.802 Intermediate Similarity NPC26888
0.8019 Intermediate Similarity NPC477054
0.8019 Intermediate Similarity NPC15396
0.8019 Intermediate Similarity NPC473928
0.8017 Intermediate Similarity NPC222688
0.8 Intermediate Similarity NPC472972
0.8 Intermediate Similarity NPC305039
0.8 Intermediate Similarity NPC163314
0.8 Intermediate Similarity NPC129689
0.8 Intermediate Similarity NPC109973
0.7982 Intermediate Similarity NPC258323
0.7982 Intermediate Similarity NPC293850
0.7981 Intermediate Similarity NPC226986
0.7981 Intermediate Similarity NPC216904
0.798 Intermediate Similarity NPC162107
0.798 Intermediate Similarity NPC46912
0.7965 Intermediate Similarity NPC96312
0.7965 Intermediate Similarity NPC40632
0.7965 Intermediate Similarity NPC266728
0.7965 Intermediate Similarity NPC235539
0.7965 Intermediate Similarity NPC152199
0.7965 Intermediate Similarity NPC251236
0.7965 Intermediate Similarity NPC328374
0.7965 Intermediate Similarity NPC134869
0.7965 Intermediate Similarity NPC49492
0.7965 Intermediate Similarity NPC148458
0.7963 Intermediate Similarity NPC265127
0.7963 Intermediate Similarity NPC469874
0.7961 Intermediate Similarity NPC184848
0.7961 Intermediate Similarity NPC69548
0.7961 Intermediate Similarity NPC473240
0.7961 Intermediate Similarity NPC474727
0.7959 Intermediate Similarity NPC98270
0.7946 Intermediate Similarity NPC250109
0.7944 Intermediate Similarity NPC159442
0.7944 Intermediate Similarity NPC275583
0.7944 Intermediate Similarity NPC36321
0.7944 Intermediate Similarity NPC191892
0.7941 Intermediate Similarity NPC79117
0.7941 Intermediate Similarity NPC470375
0.7941 Intermediate Similarity NPC206810
0.7941 Intermediate Similarity NPC470376
0.7928 Intermediate Similarity NPC115303
0.7925 Intermediate Similarity NPC477052
0.7925 Intermediate Similarity NPC477053
0.7925 Intermediate Similarity NPC477051
0.7925 Intermediate Similarity NPC474327
0.7925 Intermediate Similarity NPC253886
0.7925 Intermediate Similarity NPC121218
0.7921 Intermediate Similarity NPC148414
0.7921 Intermediate Similarity NPC175628
0.7921 Intermediate Similarity NPC111585
0.7913 Intermediate Similarity NPC473203
0.7913 Intermediate Similarity NPC472933
0.7913 Intermediate Similarity NPC475041
0.7909 Intermediate Similarity NPC77947
0.7909 Intermediate Similarity NPC286174
0.7905 Intermediate Similarity NPC475876
0.7905 Intermediate Similarity NPC114274
0.7905 Intermediate Similarity NPC477813
0.79 Intermediate Similarity NPC97884
0.79 Intermediate Similarity NPC28227
0.79 Intermediate Similarity NPC472220
0.7895 Intermediate Similarity NPC471854
0.7895 Intermediate Similarity NPC239273
0.789 Intermediate Similarity NPC144854
0.789 Intermediate Similarity NPC220974
0.789 Intermediate Similarity NPC3316
0.789 Intermediate Similarity NPC59530
0.789 Intermediate Similarity NPC176949
0.789 Intermediate Similarity NPC165873
0.789 Intermediate Similarity NPC201908
0.7885 Intermediate Similarity NPC29410
0.7885 Intermediate Similarity NPC200054
0.7885 Intermediate Similarity NPC305483
0.7885 Intermediate Similarity NPC476318
0.7885 Intermediate Similarity NPC96859
0.7885 Intermediate Similarity NPC476327
0.7885 Intermediate Similarity NPC49371
0.7885 Intermediate Similarity NPC328162
0.7881 Intermediate Similarity NPC473255
0.7879 Intermediate Similarity NPC91525
0.7879 Intermediate Similarity NPC10005
0.7879 Intermediate Similarity NPC195640
0.7879 Intermediate Similarity NPC9892
0.7879 Intermediate Similarity NPC329943
0.7876 Intermediate Similarity NPC469877
0.7876 Intermediate Similarity NPC470919
0.787 Intermediate Similarity NPC2436
0.787 Intermediate Similarity NPC477812
0.787 Intermediate Similarity NPC216245
0.787 Intermediate Similarity NPC228669
0.787 Intermediate Similarity NPC475036
0.787 Intermediate Similarity NPC164835
0.787 Intermediate Similarity NPC135854
0.787 Intermediate Similarity NPC470251
0.7864 Intermediate Similarity NPC159410
0.7864 Intermediate Similarity NPC245972
0.7864 Intermediate Similarity NPC196485
0.7864 Intermediate Similarity NPC111015
0.7863 Intermediate Similarity NPC269642
0.7857 Intermediate Similarity NPC264634
0.7857 Intermediate Similarity NPC471933
0.7857 Intermediate Similarity NPC11252
0.7857 Intermediate Similarity NPC100267
0.7857 Intermediate Similarity NPC475509
0.7857 Intermediate Similarity NPC130427
0.7857 Intermediate Similarity NPC475524
0.7857 Intermediate Similarity NPC289312
0.785 Intermediate Similarity NPC271980

  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 NPC475571 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
0.8476 Intermediate Similarity NPD6675 Approved
0.8476 Intermediate Similarity NPD6008 Approved
0.8476 Intermediate Similarity NPD6402 Approved
0.8476 Intermediate Similarity NPD5739 Approved
0.8476 Intermediate Similarity NPD7128 Approved
0.8411 Intermediate Similarity NPD6373 Approved
0.8411 Intermediate Similarity NPD6372 Approved
0.8349 Intermediate Similarity NPD8297 Approved
0.8318 Intermediate Similarity NPD6899 Approved
0.8318 Intermediate Similarity NPD6881 Approved
0.8318 Intermediate Similarity NPD7320 Approved
0.8257 Intermediate Similarity NPD8130 Phase 1
0.8257 Intermediate Similarity NPD6649 Approved
0.8257 Intermediate Similarity NPD6650 Approved
0.8224 Intermediate Similarity NPD5697 Approved
0.8224 Intermediate Similarity NPD5701 Approved
0.8182 Intermediate Similarity NPD6882 Approved
0.8165 Intermediate Similarity NPD7290 Approved
0.8165 Intermediate Similarity NPD6883 Approved
0.8165 Intermediate Similarity NPD7102 Approved
0.8148 Intermediate Similarity NPD6011 Approved
0.8091 Intermediate Similarity NPD6617 Approved
0.8091 Intermediate Similarity NPD6847 Approved
0.8091 Intermediate Similarity NPD6869 Approved
0.8091 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.8081 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.8081 Intermediate Similarity NPD6672 Approved
0.8081 Intermediate Similarity NPD5737 Approved
0.8073 Intermediate Similarity NPD6012 Approved
0.8073 Intermediate Similarity NPD6013 Approved
0.8073 Intermediate Similarity NPD6014 Approved
0.8061 Intermediate Similarity NPD6098 Approved
0.8 Intermediate Similarity NPD6904 Approved
0.8 Intermediate Similarity NPD6319 Approved
0.8 Intermediate Similarity NPD6673 Approved
0.8 Intermediate Similarity NPD6080 Approved
0.7983 Intermediate Similarity NPD7736 Approved
0.7946 Intermediate Similarity NPD4632 Approved
0.7941 Intermediate Similarity NPD6399 Phase 3
0.7895 Intermediate Similarity NPD6009 Approved
0.7879 Intermediate Similarity NPD7521 Approved
0.7879 Intermediate Similarity NPD7334 Approved
0.7879 Intermediate Similarity NPD6409 Approved
0.7879 Intermediate Similarity NPD7146 Approved
0.7879 Intermediate Similarity NPD5330 Approved
0.7879 Intermediate Similarity NPD6684 Approved
0.7864 Intermediate Similarity NPD7900 Approved
0.7864 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.781 Intermediate Similarity NPD6084 Phase 2
0.781 Intermediate Similarity NPD4755 Approved
0.781 Intermediate Similarity NPD6083 Phase 2
0.7797 Intermediate Similarity NPD7604 Phase 2
0.7778 Intermediate Similarity NPD5983 Phase 2
0.775 Intermediate Similarity NPD8293 Discontinued
0.7731 Intermediate Similarity NPD7492 Approved
0.7723 Intermediate Similarity NPD6903 Approved
0.7692 Intermediate Similarity NPD6059 Approved
0.7692 Intermediate Similarity NPD6054 Approved
0.7692 Intermediate Similarity NPD7748 Approved
0.7672 Intermediate Similarity NPD6335 Approved
0.767 Intermediate Similarity NPD6050 Approved
0.767 Intermediate Similarity NPD5693 Phase 1
0.767 Intermediate Similarity NPD8034 Phase 2
0.767 Intermediate Similarity NPD8035 Phase 2
0.7667 Intermediate Similarity NPD6616 Approved
0.7667 Intermediate Similarity NPD6336 Discontinued
0.7664 Intermediate Similarity NPD5285 Approved
0.7664 Intermediate Similarity NPD5286 Approved
0.7664 Intermediate Similarity NPD4696 Approved
0.7664 Intermediate Similarity NPD4700 Approved
0.7652 Intermediate Similarity NPD6274 Approved
0.7642 Intermediate Similarity NPD7902 Approved
0.7619 Intermediate Similarity NPD5695 Phase 3
0.7619 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD7101 Approved
0.7607 Intermediate Similarity NPD7100 Approved
0.7603 Intermediate Similarity NPD7078 Approved
0.7593 Intermediate Similarity NPD5223 Approved
0.7586 Intermediate Similarity NPD6317 Approved
0.7573 Intermediate Similarity NPD5692 Phase 3
0.757 Intermediate Similarity NPD7638 Approved
0.757 Intermediate Similarity NPD5696 Approved
0.7563 Intermediate Similarity NPD6370 Approved
0.7523 Intermediate Similarity NPD5224 Approved
0.7523 Intermediate Similarity NPD5211 Phase 2
0.7523 Intermediate Similarity NPD5225 Approved
0.7523 Intermediate Similarity NPD5226 Approved
0.7523 Intermediate Similarity NPD4633 Approved
0.7521 Intermediate Similarity NPD6313 Approved
0.7521 Intermediate Similarity NPD6314 Approved
0.75 Intermediate Similarity NPD8328 Phase 3
0.75 Intermediate Similarity NPD5694 Approved
0.75 Intermediate Similarity NPD7640 Approved
0.75 Intermediate Similarity NPD7639 Approved
0.7479 Intermediate Similarity NPD6908 Approved
0.7479 Intermediate Similarity NPD6015 Approved
0.7479 Intermediate Similarity NPD6016 Approved
0.7479 Intermediate Similarity NPD6909 Approved
0.7477 Intermediate Similarity NPD4768 Approved
0.7477 Intermediate Similarity NPD4767 Approved
0.7476 Intermediate Similarity NPD5328 Approved
0.7455 Intermediate Similarity NPD5175 Approved
0.7455 Intermediate Similarity NPD5174 Approved
0.7455 Intermediate Similarity NPD4754 Approved
0.7436 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD5988 Approved
0.7387 Intermediate Similarity NPD5141 Approved
0.7383 Intermediate Similarity NPD4697 Phase 3
0.7383 Intermediate Similarity NPD5221 Approved
0.7383 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD5222 Approved
0.7377 Intermediate Similarity NPD7507 Approved
0.7368 Intermediate Similarity NPD4634 Approved
0.735 Intermediate Similarity NPD6868 Approved
0.7345 Intermediate Similarity NPD4729 Approved
0.7345 Intermediate Similarity NPD4730 Approved
0.7333 Intermediate Similarity NPD7515 Phase 2
0.7333 Intermediate Similarity NPD6079 Approved
0.7327 Intermediate Similarity NPD4786 Approved
0.7315 Intermediate Similarity NPD5173 Approved
0.7282 Intermediate Similarity NPD3573 Approved
0.7264 Intermediate Similarity NPD4202 Approved
0.7258 Intermediate Similarity NPD6033 Approved
0.7257 Intermediate Similarity NPD6412 Phase 2
0.7255 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD5249 Phase 3
0.7217 Intermediate Similarity NPD5247 Approved
0.7217 Intermediate Similarity NPD5248 Approved
0.7217 Intermediate Similarity NPD5251 Approved
0.7217 Intermediate Similarity NPD5250 Approved
0.7212 Intermediate Similarity NPD5208 Approved
0.72 Intermediate Similarity NPD7319 Approved
0.7196 Intermediate Similarity NPD6001 Approved
0.7193 Intermediate Similarity NPD5128 Approved
0.719 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD3668 Phase 3
0.7143 Intermediate Similarity NPD4753 Phase 2
0.713 Intermediate Similarity NPD5654 Approved
0.7129 Intermediate Similarity NPD3667 Approved
0.7087 Intermediate Similarity NPD5329 Approved
0.7069 Intermediate Similarity NPD5169 Approved
0.7069 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD5135 Approved
0.7019 Intermediate Similarity NPD3618 Phase 1
0.7009 Intermediate Similarity NPD5127 Approved
0.7009 Intermediate Similarity NPD5215 Approved
0.7009 Intermediate Similarity NPD5217 Approved
0.7009 Intermediate Similarity NPD5216 Approved
0.7 Intermediate Similarity NPD5959 Approved
0.699 Remote Similarity NPD4197 Approved
0.699 Remote Similarity NPD3665 Phase 1
0.699 Remote Similarity NPD3133 Approved
0.699 Remote Similarity NPD3666 Approved
0.6983 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6051 Approved
0.6957 Remote Similarity NPD6614 Approved
0.6949 Remote Similarity NPD6053 Discontinued
0.6916 Remote Similarity NPD5207 Approved
0.6911 Remote Similarity NPD8033 Approved
0.6903 Remote Similarity NPD7632 Discontinued
0.6894 Remote Similarity NPD6333 Approved
0.6894 Remote Similarity NPD6334 Approved
0.6891 Remote Similarity NPD8133 Approved
0.686 Remote Similarity NPD7115 Discovery
0.6852 Remote Similarity NPD5284 Approved
0.6852 Remote Similarity NPD5281 Approved
0.6833 Remote Similarity NPD5167 Approved
0.6829 Remote Similarity NPD8294 Approved
0.6829 Remote Similarity NPD8377 Approved
0.6822 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5210 Approved
0.6818 Remote Similarity NPD4629 Approved
0.6804 Remote Similarity NPD5777 Approved
0.6803 Remote Similarity NPD7327 Approved
0.6803 Remote Similarity NPD7328 Approved
0.6796 Remote Similarity NPD4223 Phase 3
0.6796 Remote Similarity NPD4221 Approved
0.6774 Remote Similarity NPD8380 Approved
0.6774 Remote Similarity NPD8335 Approved
0.6774 Remote Similarity NPD8379 Approved
0.6774 Remote Similarity NPD8378 Approved
0.6774 Remote Similarity NPD8296 Approved
0.6765 Remote Similarity NPD7525 Registered
0.6752 Remote Similarity NPD5168 Approved
0.6752 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7516 Approved
0.6733 Remote Similarity NPD6114 Approved
0.6733 Remote Similarity NPD6115 Approved
0.6733 Remote Similarity NPD6697 Approved
0.6733 Remote Similarity NPD6118 Approved
0.6698 Remote Similarity NPD4694 Approved
0.6698 Remote Similarity NPD5280 Approved
0.6698 Remote Similarity NPD5690 Phase 2
0.6698 Remote Similarity NPD5279 Phase 3
0.6697 Remote Similarity NPD6411 Approved
0.6696 Remote Similarity NPD6052 Approved
0.6667 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6067 Discontinued
0.6638 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6635 Remote Similarity NPD6435 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