Structure

Physi-Chem Properties

Molecular Weight:  372.16
Volume:  386.309
LogP:  3.077
LogD:  3.04
LogS:  -4.605
# Rotatable Bonds:  8
TPSA:  63.22
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.653
Synthetic Accessibility Score:  2.29
Fsp3:  0.286
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.757
MDCK Permeability:  4.0752354834694415e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.975
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.319

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  82.85759735107422%
Volume Distribution (VD):  0.612
Pgp-substrate:  14.576787948608398%

ADMET: Metabolism

CYP1A2-inhibitor:  0.316
CYP1A2-substrate:  0.982
CYP2C19-inhibitor:  0.435
CYP2C19-substrate:  0.914
CYP2C9-inhibitor:  0.248
CYP2C9-substrate:  0.913
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.918
CYP3A4-inhibitor:  0.618
CYP3A4-substrate:  0.862

ADMET: Excretion

Clearance (CL):  8.506
Half-life (T1/2):  0.79

ADMET: Toxicity

hERG Blockers:  0.08
Human Hepatotoxicity (H-HT):  0.1
Drug-inuced Liver Injury (DILI):  0.835
AMES Toxicity:  0.14
Rat Oral Acute Toxicity:  0.036
Maximum Recommended Daily Dose:  0.072
Skin Sensitization:  0.134
Carcinogencity:  0.045
Eye Corrosion:  0.003
Eye Irritation:  0.044
Respiratory Toxicity:  0.377

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

  Natural Product: NPC470961

Natural Product ID:  NPC470961
Common Name*:   Withacoagulin H
IUPAC Name:   (2R)-2-[(1S)-1-hydroxy-1-[(8R,9S,10R,13S,17R)-17-hydroxy-10,13-dimethyl-1-oxo-7,8,9,11,12,16-hexahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Synonyms:   Withacoagulin H
Standard InCHIKey:  UNWUYUBEZUQEBC-DREDRYRMSA-N
Standard InCHI:  InChI=1S/C28H36O6/c1-16-14-23(34-24(31)19(16)15-29)27(4,32)28(33)13-11-20-18-9-8-17-6-5-7-22(30)26(17,3)21(18)10-12-25(20,28)2/h5,7-8,11,18,21,23,29,32-33H,6,9-10,12-15H2,1-4H3/t18-,21-,23+,25-,26-,27-,28+/m0/s1
SMILES:  OCC1=C(C)C[C@@H](OC1=O)[C@@]([C@@]1(O)CC=C2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)C(=O)C=CC2)(O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2333672
PubChem CID:   71524298
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001125] Steroid lactones
          • [CHEMONTID:0001560] Withanolides 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
NPO13927 Withania coagulans Species Solanaceae Eukaryota fruits n.a. n.a. PMID[18952419]
NPO13927 Withania coagulans Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[23316950]
NPO13927 Withania coagulans Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13927 Withania coagulans Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13927 Withania coagulans Species Solanaceae 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 3100.0 nM PMID[551859]
NPT71 Cell Line HEK293 Homo sapiens Survival = 90.3 % PMID[551859]
NPT113 Cell Line RAW264.7 Mus musculus Survival = 70.4 % PMID[551859]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 100.0 % PMID[551859]
NPT2 Others Unspecified IC50 = 5000.0 nM PMID[551859]
NPT2 Others Unspecified Inhibition = 98.3 % PMID[551859]

☑ 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 NPC470961 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
0.9902 High Similarity NPC29133
0.9712 High Similarity NPC191620
0.9266 High Similarity NPC186525
0.9259 High Similarity NPC64318
0.9231 High Similarity NPC91034
0.9174 High Similarity NPC183580
0.9174 High Similarity NPC312824
0.9174 High Similarity NPC470493
0.9151 High Similarity NPC37116
0.9018 High Similarity NPC46570
0.9009 High Similarity NPC264954
0.9 High Similarity NPC286528
0.9 High Similarity NPC140055
0.9 High Similarity NPC470492
0.9 High Similarity NPC20302
0.9 High Similarity NPC167606
0.8991 High Similarity NPC147912
0.8991 High Similarity NPC67259
0.8981 High Similarity NPC236217
0.8962 High Similarity NPC220155
0.8938 High Similarity NPC107493
0.8929 High Similarity NPC474370
0.8919 High Similarity NPC709
0.8919 High Similarity NPC50774
0.8909 High Similarity NPC176840
0.8796 High Similarity NPC473627
0.8772 High Similarity NPC88326
0.8772 High Similarity NPC153700
0.8727 High Similarity NPC122056
0.8716 High Similarity NPC474315
0.8684 High Similarity NPC67569
0.8649 High Similarity NPC474181
0.8621 High Similarity NPC8374
0.8609 High Similarity NPC470265
0.8609 High Similarity NPC23786
0.8596 High Similarity NPC79579
0.8584 High Similarity NPC153440
0.8571 High Similarity NPC190286
0.8545 High Similarity NPC324683
0.8534 High Similarity NPC469789
0.8522 High Similarity NPC473256
0.8522 High Similarity NPC470878
0.8509 High Similarity NPC473274
0.8509 High Similarity NPC5292
0.8509 High Similarity NPC473270
0.8462 Intermediate Similarity NPC172154
0.8462 Intermediate Similarity NPC8369
0.8462 Intermediate Similarity NPC3381
0.8462 Intermediate Similarity NPC81736
0.8462 Intermediate Similarity NPC470494
0.8435 Intermediate Similarity NPC474585
0.8421 Intermediate Similarity NPC329736
0.8421 Intermediate Similarity NPC475913
0.8407 Intermediate Similarity NPC270929
0.839 Intermediate Similarity NPC293112
0.8376 Intermediate Similarity NPC11895
0.8364 Intermediate Similarity NPC475065
0.835 Intermediate Similarity NPC53685
0.8349 Intermediate Similarity NPC329048
0.8349 Intermediate Similarity NPC330011
0.8348 Intermediate Similarity NPC474179
0.8348 Intermediate Similarity NPC270850
0.8348 Intermediate Similarity NPC475834
0.8348 Intermediate Similarity NPC61520
0.8348 Intermediate Similarity NPC305260
0.8333 Intermediate Similarity NPC476965
0.8333 Intermediate Similarity NPC470959
0.8333 Intermediate Similarity NPC303697
0.8333 Intermediate Similarity NPC243065
0.8333 Intermediate Similarity NPC473175
0.8319 Intermediate Similarity NPC287903
0.8304 Intermediate Similarity NPC221144
0.8304 Intermediate Similarity NPC69291
0.8302 Intermediate Similarity NPC474012
0.8302 Intermediate Similarity NPC476299
0.8291 Intermediate Similarity NPC170538
0.8291 Intermediate Similarity NPC269642
0.8273 Intermediate Similarity NPC473482
0.8273 Intermediate Similarity NPC318363
0.8273 Intermediate Similarity NPC472825
0.8273 Intermediate Similarity NPC475418
0.8252 Intermediate Similarity NPC115021
0.8241 Intermediate Similarity NPC470954
0.8224 Intermediate Similarity NPC469657
0.8224 Intermediate Similarity NPC473174
0.8224 Intermediate Similarity NPC99411
0.8224 Intermediate Similarity NPC244456
0.822 Intermediate Similarity NPC473979
0.8208 Intermediate Similarity NPC316598
0.8208 Intermediate Similarity NPC235464
0.8208 Intermediate Similarity NPC98868
0.8208 Intermediate Similarity NPC197386
0.8208 Intermediate Similarity NPC166745
0.8198 Intermediate Similarity NPC41405
0.819 Intermediate Similarity NPC475041
0.8182 Intermediate Similarity NPC473284
0.8182 Intermediate Similarity NPC473593
0.8182 Intermediate Similarity NPC475294
0.8174 Intermediate Similarity NPC239273
0.8167 Intermediate Similarity NPC156797
0.8165 Intermediate Similarity NPC296950
0.8165 Intermediate Similarity NPC146731
0.8158 Intermediate Similarity NPC284915
0.8158 Intermediate Similarity NPC470953
0.8148 Intermediate Similarity NPC473163
0.8148 Intermediate Similarity NPC475320
0.8142 Intermediate Similarity NPC475524
0.8142 Intermediate Similarity NPC470063
0.8142 Intermediate Similarity NPC100267
0.812 Intermediate Similarity NPC476961
0.8113 Intermediate Similarity NPC53844
0.8113 Intermediate Similarity NPC476253
0.8103 Intermediate Similarity NPC257457
0.8103 Intermediate Similarity NPC311554
0.8099 Intermediate Similarity NPC245094
0.8095 Intermediate Similarity NPC171395
0.8087 Intermediate Similarity NPC148458
0.8083 Intermediate Similarity NPC473635
0.8077 Intermediate Similarity NPC474736
0.8073 Intermediate Similarity NPC476889
0.8073 Intermediate Similarity NPC475050
0.8056 Intermediate Similarity NPC310981
0.8056 Intermediate Similarity NPC472924
0.8049 Intermediate Similarity NPC231240
0.8037 Intermediate Similarity NPC478056
0.8037 Intermediate Similarity NPC471717
0.8036 Intermediate Similarity NPC472216
0.8036 Intermediate Similarity NPC137911
0.8036 Intermediate Similarity NPC284828
0.8036 Intermediate Similarity NPC173905
0.8036 Intermediate Similarity NPC228477
0.8036 Intermediate Similarity NPC47951
0.8036 Intermediate Similarity NPC5475
0.8033 Intermediate Similarity NPC231529
0.8033 Intermediate Similarity NPC476966
0.8019 Intermediate Similarity NPC328371
0.8019 Intermediate Similarity NPC117133
0.8019 Intermediate Similarity NPC456
0.8019 Intermediate Similarity NPC472941
0.8018 Intermediate Similarity NPC144459
0.8017 Intermediate Similarity NPC284068
0.8017 Intermediate Similarity NPC471854
0.8 Intermediate Similarity NPC472868
0.8 Intermediate Similarity NPC13385
0.8 Intermediate Similarity NPC318135
0.7984 Intermediate Similarity NPC316915
0.7982 Intermediate Similarity NPC473424
0.7982 Intermediate Similarity NPC40918
0.7982 Intermediate Similarity NPC476890
0.7982 Intermediate Similarity NPC269530
0.7981 Intermediate Similarity NPC177037
0.7981 Intermediate Similarity NPC472814
0.7967 Intermediate Similarity NPC196921
0.7967 Intermediate Similarity NPC220757
0.7966 Intermediate Similarity NPC476962
0.7965 Intermediate Similarity NPC5103
0.7965 Intermediate Similarity NPC235014
0.7965 Intermediate Similarity NPC5284
0.7963 Intermediate Similarity NPC54705
0.7961 Intermediate Similarity NPC5509
0.7949 Intermediate Similarity NPC288679
0.7946 Intermediate Similarity NPC177064
0.7946 Intermediate Similarity NPC151393
0.7944 Intermediate Similarity NPC253826
0.7944 Intermediate Similarity NPC156546
0.7944 Intermediate Similarity NPC107243
0.7944 Intermediate Similarity NPC202705
0.7931 Intermediate Similarity NPC470075
0.7931 Intermediate Similarity NPC476963
0.7928 Intermediate Similarity NPC266570
0.7928 Intermediate Similarity NPC472935
0.7928 Intermediate Similarity NPC477125
0.7928 Intermediate Similarity NPC189863
0.7928 Intermediate Similarity NPC60681
0.7925 Intermediate Similarity NPC472932
0.7925 Intermediate Similarity NPC318282
0.7925 Intermediate Similarity NPC209355
0.7925 Intermediate Similarity NPC469995
0.7925 Intermediate Similarity NPC33473
0.7925 Intermediate Similarity NPC173875
0.7925 Intermediate Similarity NPC174948
0.7917 Intermediate Similarity NPC204812
0.7917 Intermediate Similarity NPC120724
0.7913 Intermediate Similarity NPC255017
0.7913 Intermediate Similarity NPC25909
0.7913 Intermediate Similarity NPC469454
0.7913 Intermediate Similarity NPC469496
0.7913 Intermediate Similarity NPC469463
0.7909 Intermediate Similarity NPC111323
0.7909 Intermediate Similarity NPC95899
0.7909 Intermediate Similarity NPC474207
0.7909 Intermediate Similarity NPC475526
0.7909 Intermediate Similarity NPC72151
0.7909 Intermediate Similarity NPC236390
0.7909 Intermediate Similarity NPC264048
0.7909 Intermediate Similarity NPC474330
0.7909 Intermediate Similarity NPC329345
0.7909 Intermediate Similarity NPC473283
0.7909 Intermediate Similarity NPC26478
0.7909 Intermediate Similarity NPC324001

  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 NPC470961 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
0.9 High Similarity NPD7115 Discovery
0.787 Intermediate Similarity NPD4225 Approved
0.7807 Intermediate Similarity NPD6371 Approved
0.7778 Intermediate Similarity NPD6083 Phase 2
0.7778 Intermediate Similarity NPD6084 Phase 2
0.7757 Intermediate Similarity NPD5695 Phase 3
0.7714 Intermediate Similarity NPD5785 Approved
0.7672 Intermediate Similarity NPD8297 Approved
0.7632 Intermediate Similarity NPD6899 Approved
0.7632 Intermediate Similarity NPD6881 Approved
0.7544 Intermediate Similarity NPD5697 Approved
0.7521 Intermediate Similarity NPD6319 Approved
0.75 Intermediate Similarity NPD6883 Approved
0.75 Intermediate Similarity NPD7102 Approved
0.75 Intermediate Similarity NPD7290 Approved
0.7478 Intermediate Similarity NPD6686 Approved
0.7477 Intermediate Similarity NPD7640 Approved
0.7477 Intermediate Similarity NPD7639 Approved
0.7456 Intermediate Similarity NPD6675 Approved
0.7456 Intermediate Similarity NPD7128 Approved
0.7456 Intermediate Similarity NPD6402 Approved
0.7456 Intermediate Similarity NPD5739 Approved
0.7436 Intermediate Similarity NPD6617 Approved
0.7436 Intermediate Similarity NPD8130 Phase 1
0.7436 Intermediate Similarity NPD6869 Approved
0.7436 Intermediate Similarity NPD6649 Approved
0.7436 Intermediate Similarity NPD6847 Approved
0.7436 Intermediate Similarity NPD6650 Approved
0.7414 Intermediate Similarity NPD6013 Approved
0.7414 Intermediate Similarity NPD6014 Approved
0.7414 Intermediate Similarity NPD6012 Approved
0.7407 Intermediate Similarity NPD6399 Phase 3
0.7391 Intermediate Similarity NPD6412 Phase 2
0.7387 Intermediate Similarity NPD5696 Approved
0.7387 Intermediate Similarity NPD7638 Approved
0.7373 Intermediate Similarity NPD6053 Discontinued
0.7373 Intermediate Similarity NPD6882 Approved
0.7358 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD5211 Phase 2
0.7333 Intermediate Similarity NPD7521 Approved
0.7333 Intermediate Similarity NPD7334 Approved
0.7333 Intermediate Similarity NPD5330 Approved
0.7333 Intermediate Similarity NPD7146 Approved
0.7333 Intermediate Similarity NPD6409 Approved
0.7333 Intermediate Similarity NPD6684 Approved
0.7328 Intermediate Similarity NPD6011 Approved
0.7328 Intermediate Similarity NPD7320 Approved
0.7323 Intermediate Similarity NPD7319 Approved
0.7317 Intermediate Similarity NPD7503 Approved
0.7315 Intermediate Similarity NPD6411 Approved
0.7315 Intermediate Similarity NPD5281 Approved
0.7315 Intermediate Similarity NPD5284 Approved
0.7315 Intermediate Similarity NPD5693 Phase 1
0.7311 Intermediate Similarity NPD4632 Approved
0.729 Intermediate Similarity NPD4753 Phase 2
0.728 Intermediate Similarity NPD7492 Approved
0.7273 Intermediate Similarity NPD5210 Approved
0.7273 Intermediate Similarity NPD4629 Approved
0.7273 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD6372 Approved
0.7265 Intermediate Similarity NPD6373 Approved
0.7248 Intermediate Similarity NPD5778 Approved
0.7248 Intermediate Similarity NPD5779 Approved
0.7244 Intermediate Similarity NPD7736 Approved
0.7241 Intermediate Similarity NPD5701 Approved
0.7241 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD5363 Approved
0.7236 Intermediate Similarity NPD6054 Approved
0.7222 Intermediate Similarity NPD7507 Approved
0.7222 Intermediate Similarity NPD6616 Approved
0.7217 Intermediate Similarity NPD5141 Approved
0.7203 Intermediate Similarity NPD4634 Approved
0.7196 Intermediate Similarity NPD6672 Approved
0.7196 Intermediate Similarity NPD6903 Approved
0.7196 Intermediate Similarity NPD5737 Approved
0.7182 Intermediate Similarity NPD7748 Approved
0.717 Intermediate Similarity NPD5690 Phase 2
0.7168 Intermediate Similarity NPD5286 Approved
0.7168 Intermediate Similarity NPD4696 Approved
0.7168 Intermediate Similarity NPD5285 Approved
0.7165 Intermediate Similarity NPD7078 Approved
0.7156 Intermediate Similarity NPD6050 Approved
0.7156 Intermediate Similarity NPD7515 Phase 2
0.7156 Intermediate Similarity NPD6079 Approved
0.7156 Intermediate Similarity NPD7637 Suspended
0.7156 Intermediate Similarity NPD5694 Approved
0.7143 Intermediate Similarity NPD4786 Approved
0.7143 Intermediate Similarity NPD3665 Phase 1
0.7143 Intermediate Similarity NPD3133 Approved
0.7143 Intermediate Similarity NPD3666 Approved
0.713 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD6673 Approved
0.713 Intermediate Similarity NPD6101 Approved
0.713 Intermediate Similarity NPD6904 Approved
0.713 Intermediate Similarity NPD6080 Approved
0.712 Intermediate Similarity NPD6370 Approved
0.7119 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD1694 Approved
0.7064 Intermediate Similarity NPD5692 Phase 3
0.7064 Intermediate Similarity NPD5207 Approved
0.7048 Intermediate Similarity NPD5362 Discontinued
0.7048 Intermediate Similarity NPD7154 Phase 3
0.7043 Intermediate Similarity NPD5226 Approved
0.7043 Intermediate Similarity NPD5224 Approved
0.7043 Intermediate Similarity NPD5225 Approved
0.7043 Intermediate Similarity NPD4633 Approved
0.704 Intermediate Similarity NPD6015 Approved
0.704 Intermediate Similarity NPD6016 Approved
0.7016 Intermediate Similarity NPD7101 Approved
0.7016 Intermediate Similarity NPD7100 Approved
0.7009 Intermediate Similarity NPD5279 Phase 3
0.7009 Intermediate Similarity NPD4623 Approved
0.7009 Intermediate Similarity NPD4519 Discontinued
0.7 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.6992 Remote Similarity NPD6009 Approved
0.6991 Remote Similarity NPD4755 Approved
0.6991 Remote Similarity NPD7902 Approved
0.6984 Remote Similarity NPD5988 Approved
0.6983 Remote Similarity NPD5175 Approved
0.6983 Remote Similarity NPD5174 Approved
0.6972 Remote Similarity NPD5328 Approved
0.6972 Remote Similarity NPD6051 Approved
0.6964 Remote Similarity NPD6356 Clinical (unspecified phase)
0.696 Remote Similarity NPD6059 Approved
0.6957 Remote Similarity NPD5223 Approved
0.6952 Remote Similarity NPD4270 Approved
0.6952 Remote Similarity NPD3667 Approved
0.6952 Remote Similarity NPD4223 Phase 3
0.6952 Remote Similarity NPD4269 Approved
0.6952 Remote Similarity NPD4221 Approved
0.6937 Remote Similarity NPD4202 Approved
0.6935 Remote Similarity NPD7327 Approved
0.6935 Remote Similarity NPD6335 Approved
0.6935 Remote Similarity NPD7328 Approved
0.6929 Remote Similarity NPD7604 Phase 2
0.6916 Remote Similarity NPD5329 Approved
0.6911 Remote Similarity NPD6274 Approved
0.6909 Remote Similarity NPD46 Approved
0.6909 Remote Similarity NPD6698 Approved
0.6905 Remote Similarity NPD8033 Approved
0.6905 Remote Similarity NPD5983 Phase 2
0.6905 Remote Similarity NPD8513 Phase 3
0.6903 Remote Similarity NPD5221 Approved
0.6903 Remote Similarity NPD5222 Approved
0.6903 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6899 Remote Similarity NPD8293 Discontinued
0.6897 Remote Similarity NPD7632 Discontinued
0.6893 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6891 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6881 Remote Similarity NPD5208 Approved
0.688 Remote Similarity NPD7516 Approved
0.687 Remote Similarity NPD4700 Approved
0.686 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5369 Approved
0.6855 Remote Similarity NPD6317 Approved
0.6852 Remote Similarity NPD5786 Approved
0.6852 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6852 Remote Similarity NPD3618 Phase 1
0.6852 Remote Similarity NPD6098 Approved
0.6852 Remote Similarity NPD5280 Approved
0.6852 Remote Similarity NPD4694 Approved
0.6842 Remote Similarity NPD5173 Approved
0.6825 Remote Similarity NPD8294 Approved
0.6825 Remote Similarity NPD8377 Approved
0.6822 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6822 Remote Similarity NPD6336 Discontinued
0.6822 Remote Similarity NPD4197 Approved
0.6818 Remote Similarity NPD7285 Clinical (unspecified phase)
0.681 Remote Similarity NPD5344 Discontinued
0.68 Remote Similarity NPD6313 Approved
0.68 Remote Similarity NPD6314 Approved
0.6789 Remote Similarity NPD3573 Approved
0.6777 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6868 Approved
0.6772 Remote Similarity NPD8380 Approved
0.6772 Remote Similarity NPD8379 Approved
0.6772 Remote Similarity NPD8516 Approved
0.6772 Remote Similarity NPD8378 Approved
0.6772 Remote Similarity NPD8296 Approved
0.6772 Remote Similarity NPD8517 Approved
0.6772 Remote Similarity NPD8335 Approved
0.6772 Remote Similarity NPD8515 Approved
0.6762 Remote Similarity NPD4252 Approved
0.675 Remote Similarity NPD4730 Approved
0.675 Remote Similarity NPD4729 Approved
0.6748 Remote Similarity NPD8133 Approved
0.6746 Remote Similarity NPD4522 Approved
0.6729 Remote Similarity NPD4788 Approved
0.6726 Remote Similarity NPD7900 Approved
0.6726 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6724 Remote Similarity NPD6404 Discontinued
0.6723 Remote Similarity NPD6008 Approved
0.6697 Remote Similarity NPD4689 Approved
0.6697 Remote Similarity NPD4690 Approved
0.6697 Remote Similarity NPD4693 Phase 3
0.6697 Remote Similarity NPD5205 Approved
0.6697 Remote Similarity NPD4688 Approved
0.6697 Remote Similarity NPD4138 Approved
0.6696 Remote Similarity NPD7983 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