Structure

Physi-Chem Properties

Molecular Weight:  458.27
Volume:  480.881
LogP:  3.017
LogD:  2.368
LogS:  -3.945
# Rotatable Bonds:  4
TPSA:  105.58
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.674
Synthetic Accessibility Score:  4.855
Fsp3:  0.815
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.499
MDCK Permeability:  1.902781514218077e-05
Pgp-inhibitor:  0.276
Pgp-substrate:  0.008
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.69
Plasma Protein Binding (PPB):  75.04168701171875%
Volume Distribution (VD):  0.438
Pgp-substrate:  17.15291976928711%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.405
CYP2C19-inhibitor:  0.012
CYP2C19-substrate:  0.902
CYP2C9-inhibitor:  0.038
CYP2C9-substrate:  0.951
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.138
CYP3A4-inhibitor:  0.088
CYP3A4-substrate:  0.287

ADMET: Excretion

Clearance (CL):  11.949
Half-life (T1/2):  0.887

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.175
Drug-inuced Liver Injury (DILI):  0.06
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.676
Maximum Recommended Daily Dose:  0.157
Skin Sensitization:  0.029
Carcinogencity:  0.129
Eye Corrosion:  0.419
Eye Irritation:  0.065
Respiratory Toxicity:  0.694

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

  Natural Product: NPC37646

Natural Product ID:  NPC37646
Common Name*:   Lucidenic Acid A
IUPAC Name:   (4R)-4-[(5R,7S,10S,13R,14R,17R)-7-hydroxy-4,4,10,13,14-pentamethyl-3,11,15-trioxo-1,2,5,6,7,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
Synonyms:  
Standard InCHIKey:  INIPQDKLXQHEAJ-NCQSLMINSA-N
Standard InCHI:  InChI=1S/C27H38O6/c1-14(7-8-21(32)33)15-11-20(31)27(6)23-16(28)12-18-24(2,3)19(30)9-10-25(18,4)22(23)17(29)13-26(15,27)5/h14-16,18,28H,7-13H2,1-6H3,(H,32,33)/t14-,15-,16+,18+,25+,26-,27+/m1/s1
SMILES:  OC(=O)CC[C@H]([C@H]1CC(=O)[C@@]2([C@]1(C)CC(=O)C1=C2[C@@H](O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL460969
PubChem CID:   14109375
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
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytochem.2005.10.025]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[11520245]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[12045343]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[14695801]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[1791484]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. spore n.a. PMID[18827358]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting bodies Nagano, Japan 2008-MAY PMID[20039640]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[20384295]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting bodies n.a. n.a. PMID[20702092]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting bodies n.a. n.a. PMID[21924611]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[22014750]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[22044278]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota fruiting body n.a. n.a. PMID[22047696]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[26222905]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[9635497]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16609 Ganoderma sinense Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16609 Ganoderma sinense Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25269 Ganoderma lucidum Species Ganodermataceae 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
NPT65 Cell Line HepG2 Homo sapiens IC50 = 0.164 nM PMID[469152]
NPT91 Cell Line KB Homo sapiens IC50 = 16970.0 nM PMID[469152]
NPT168 Cell Line P388 Mus musculus IC50 = 17.0 nM PMID[469152]
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[469153]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 24040.0 nM PMID[469154]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 > 200000.0 nM PMID[469154]
NPT165 Cell Line HeLa Homo sapiens IC50 > 300000.0 nM PMID[469155]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 0.205 nM PMID[469152]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 27510.0 nM PMID[469152]
NPT2 Others Unspecified Activity = 0.0 % PMID[469153]
NPT2 Others Unspecified Activity = 22.7 % PMID[469153]
NPT2 Others Unspecified Activity = 73.0 % PMID[469153]
NPT2 Others Unspecified Activity = 96.1 % PMID[469153]
NPT2 Others Unspecified IC50 = 280.0 molar ratio PMID[469153]

☑ 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 NPC37646 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
0.9888 High Similarity NPC3772
0.9888 High Similarity NPC243525
0.9888 High Similarity NPC40765
0.9778 High Similarity NPC106557
0.9778 High Similarity NPC121339
0.9565 High Similarity NPC51370
0.9565 High Similarity NPC287833
0.9444 High Similarity NPC184870
0.9438 High Similarity NPC107690
0.9348 High Similarity NPC122294
0.9341 High Similarity NPC318282
0.9341 High Similarity NPC469995
0.9341 High Similarity NPC173875
0.9341 High Similarity NPC255809
0.9341 High Similarity NPC174948
0.9333 High Similarity NPC470254
0.9263 High Similarity NPC251017
0.9247 High Similarity NPC16021
0.9247 High Similarity NPC10364
0.9239 High Similarity NPC328371
0.9239 High Similarity NPC472941
0.9239 High Similarity NPC456
0.9149 High Similarity NPC144660
0.9149 High Similarity NPC299971
0.9149 High Similarity NPC205899
0.9149 High Similarity NPC307954
0.914 High Similarity NPC18319
0.913 High Similarity NPC241156
0.9072 High Similarity NPC51452
0.9032 High Similarity NPC125622
0.9 High Similarity NPC214387
0.898 High Similarity NPC473037
0.8958 High Similarity NPC204450
0.8958 High Similarity NPC293753
0.8958 High Similarity NPC56498
0.8958 High Similarity NPC281702
0.8958 High Similarity NPC234892
0.8958 High Similarity NPC195290
0.8947 High Similarity NPC157787
0.8947 High Similarity NPC88198
0.8925 High Similarity NPC297199
0.8913 High Similarity NPC25750
0.8913 High Similarity NPC472930
0.8901 High Similarity NPC477149
0.8901 High Similarity NPC477147
0.8889 High Similarity NPC295244
0.8866 High Similarity NPC55872
0.8866 High Similarity NPC236390
0.8854 High Similarity NPC302537
0.8854 High Similarity NPC472924
0.8854 High Similarity NPC163372
0.8842 High Similarity NPC471717
0.8842 High Similarity NPC197386
0.883 High Similarity NPC95565
0.883 High Similarity NPC7124
0.8817 High Similarity NPC166906
0.8804 High Similarity NPC63748
0.88 High Similarity NPC77947
0.88 High Similarity NPC286174
0.8776 High Similarity NPC28656
0.8764 High Similarity NPC473038
0.8763 High Similarity NPC308726
0.8763 High Similarity NPC119601
0.8737 High Similarity NPC320306
0.8737 High Similarity NPC43747
0.8723 High Similarity NPC470016
0.8723 High Similarity NPC317586
0.8713 High Similarity NPC272898
0.8713 High Similarity NPC473036
0.8713 High Similarity NPC129689
0.871 High Similarity NPC69454
0.8673 High Similarity NPC70967
0.8673 High Similarity NPC33973
0.8652 High Similarity NPC209882
0.8632 High Similarity NPC305483
0.8632 High Similarity NPC249954
0.8632 High Similarity NPC328162
0.8632 High Similarity NPC96859
0.8627 High Similarity NPC115303
0.8627 High Similarity NPC472928
0.8586 High Similarity NPC135854
0.8586 High Similarity NPC470251
0.8586 High Similarity NPC2436
0.8586 High Similarity NPC216245
0.8571 High Similarity NPC99909
0.8557 High Similarity NPC327431
0.8557 High Similarity NPC198880
0.8557 High Similarity NPC316964
0.8557 High Similarity NPC476274
0.8526 High Similarity NPC472932
0.8526 High Similarity NPC259286
0.8511 High Similarity NPC243866
0.85 High Similarity NPC323834
0.8495 Intermediate Similarity NPC289213
0.8495 Intermediate Similarity NPC469400
0.8478 Intermediate Similarity NPC143767
0.8478 Intermediate Similarity NPC131470
0.8469 Intermediate Similarity NPC476223
0.8469 Intermediate Similarity NPC124211
0.8469 Intermediate Similarity NPC476240
0.8469 Intermediate Similarity NPC224720
0.8454 Intermediate Similarity NPC166745
0.8454 Intermediate Similarity NPC235464
0.8421 Intermediate Similarity NPC469406
0.8416 Intermediate Similarity NPC472925
0.8404 Intermediate Similarity NPC233116
0.8387 Intermediate Similarity NPC123912
0.8387 Intermediate Similarity NPC54689
0.8387 Intermediate Similarity NPC86319
0.8387 Intermediate Similarity NPC275740
0.8384 Intermediate Similarity NPC136289
0.8384 Intermediate Similarity NPC53222
0.8352 Intermediate Similarity NPC94531
0.8352 Intermediate Similarity NPC474083
0.8352 Intermediate Similarity NPC311702
0.8352 Intermediate Similarity NPC123319
0.8333 Intermediate Similarity NPC469561
0.8333 Intermediate Similarity NPC271784
0.8333 Intermediate Similarity NPC476174
0.8316 Intermediate Similarity NPC206810
0.8298 Intermediate Similarity NPC183283
0.8298 Intermediate Similarity NPC20388
0.8298 Intermediate Similarity NPC48010
0.8286 Intermediate Similarity NPC472929
0.8283 Intermediate Similarity NPC81530
0.828 Intermediate Similarity NPC476796
0.828 Intermediate Similarity NPC242864
0.8265 Intermediate Similarity NPC48647
0.8261 Intermediate Similarity NPC28252
0.8261 Intermediate Similarity NPC322159
0.8261 Intermediate Similarity NPC55309
0.8261 Intermediate Similarity NPC72133
0.8247 Intermediate Similarity NPC155676
0.8242 Intermediate Similarity NPC165064
0.8242 Intermediate Similarity NPC473246
0.8235 Intermediate Similarity NPC185
0.8229 Intermediate Similarity NPC471720
0.8224 Intermediate Similarity NPC472927
0.8211 Intermediate Similarity NPC473998
0.8211 Intermediate Similarity NPC23434
0.8211 Intermediate Similarity NPC297265
0.82 Intermediate Similarity NPC473424
0.82 Intermediate Similarity NPC477915
0.8191 Intermediate Similarity NPC473999
0.8191 Intermediate Similarity NPC309603
0.8191 Intermediate Similarity NPC155479
0.8191 Intermediate Similarity NPC473039
0.8191 Intermediate Similarity NPC477943
0.819 Intermediate Similarity NPC285956
0.8182 Intermediate Similarity NPC218383
0.8173 Intermediate Similarity NPC470496
0.8173 Intermediate Similarity NPC37116
0.8172 Intermediate Similarity NPC136948
0.8172 Intermediate Similarity NPC159046
0.8172 Intermediate Similarity NPC233836
0.8172 Intermediate Similarity NPC187376
0.8163 Intermediate Similarity NPC216904
0.8163 Intermediate Similarity NPC475894
0.8163 Intermediate Similarity NPC23680
0.8163 Intermediate Similarity NPC107243
0.8163 Intermediate Similarity NPC253826
0.8152 Intermediate Similarity NPC472940
0.8152 Intermediate Similarity NPC472931
0.8152 Intermediate Similarity NPC11711
0.8152 Intermediate Similarity NPC471224
0.8152 Intermediate Similarity NPC8571
0.8144 Intermediate Similarity NPC200702
0.8144 Intermediate Similarity NPC271195
0.8144 Intermediate Similarity NPC48330
0.8132 Intermediate Similarity NPC470015
0.8132 Intermediate Similarity NPC168188
0.8132 Intermediate Similarity NPC41539
0.8125 Intermediate Similarity NPC214697
0.8125 Intermediate Similarity NPC152897
0.8125 Intermediate Similarity NPC66429
0.8119 Intermediate Similarity NPC111323
0.81 Intermediate Similarity NPC99411
0.8085 Intermediate Similarity NPC471722
0.8085 Intermediate Similarity NPC328539
0.8081 Intermediate Similarity NPC112753
0.8081 Intermediate Similarity NPC275439
0.8081 Intermediate Similarity NPC186810
0.8081 Intermediate Similarity NPC114274
0.8081 Intermediate Similarity NPC478056
0.8081 Intermediate Similarity NPC147954
0.8073 Intermediate Similarity NPC472933
0.8065 Intermediate Similarity NPC212843
0.8065 Intermediate Similarity NPC229717
0.8061 Intermediate Similarity NPC250757
0.8061 Intermediate Similarity NPC173272
0.8061 Intermediate Similarity NPC301534
0.8061 Intermediate Similarity NPC471463
0.8061 Intermediate Similarity NPC117133
0.8061 Intermediate Similarity NPC29152
0.8058 Intermediate Similarity NPC91034
0.8056 Intermediate Similarity NPC472934
0.8043 Intermediate Similarity NPC164577
0.8043 Intermediate Similarity NPC7927
0.8043 Intermediate Similarity NPC109512
0.8043 Intermediate Similarity NPC320801

  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 NPC37646 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
0.8191 Intermediate Similarity NPD5328 Approved
0.8021 Intermediate Similarity NPD6079 Approved
0.7879 Intermediate Similarity NPD4697 Phase 3
0.7872 Intermediate Similarity NPD3618 Phase 1
0.7788 Intermediate Similarity NPD7128 Approved
0.7788 Intermediate Similarity NPD5739 Approved
0.7788 Intermediate Similarity NPD6675 Approved
0.7788 Intermediate Similarity NPD6402 Approved
0.7755 Intermediate Similarity NPD6399 Phase 3
0.7736 Intermediate Similarity NPD6372 Approved
0.7736 Intermediate Similarity NPD6373 Approved
0.7723 Intermediate Similarity NPD5696 Approved
0.77 Intermediate Similarity NPD5222 Approved
0.77 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.77 Intermediate Similarity NPD5221 Approved
0.7684 Intermediate Similarity NPD5279 Phase 3
0.767 Intermediate Similarity NPD5211 Phase 2
0.766 Intermediate Similarity NPD3133 Approved
0.766 Intermediate Similarity NPD3665 Phase 1
0.766 Intermediate Similarity NPD4786 Approved
0.766 Intermediate Similarity NPD3666 Approved
0.7653 Intermediate Similarity NPD5281 Approved
0.7653 Intermediate Similarity NPD7515 Phase 2
0.7653 Intermediate Similarity NPD5284 Approved
0.7642 Intermediate Similarity NPD7320 Approved
0.7642 Intermediate Similarity NPD6899 Approved
0.7642 Intermediate Similarity NPD6881 Approved
0.7624 Intermediate Similarity NPD6084 Phase 2
0.7624 Intermediate Similarity NPD5173 Approved
0.7624 Intermediate Similarity NPD6083 Phase 2
0.7624 Intermediate Similarity NPD4755 Approved
0.76 Intermediate Similarity NPD4629 Approved
0.76 Intermediate Similarity NPD5695 Phase 3
0.76 Intermediate Similarity NPD5210 Approved
0.7593 Intermediate Similarity NPD6649 Approved
0.7593 Intermediate Similarity NPD6650 Approved
0.7547 Intermediate Similarity NPD5701 Approved
0.7547 Intermediate Similarity NPD5697 Approved
0.7526 Intermediate Similarity NPD6672 Approved
0.7526 Intermediate Similarity NPD5737 Approved
0.7524 Intermediate Similarity NPD5141 Approved
0.75 Intermediate Similarity NPD6684 Approved
0.75 Intermediate Similarity NPD7290 Approved
0.75 Intermediate Similarity NPD7334 Approved
0.75 Intermediate Similarity NPD7146 Approved
0.75 Intermediate Similarity NPD7521 Approved
0.75 Intermediate Similarity NPD6409 Approved
0.75 Intermediate Similarity NPD6883 Approved
0.75 Intermediate Similarity NPD7102 Approved
0.75 Intermediate Similarity NPD5330 Approved
0.7477 Intermediate Similarity NPD6011 Approved
0.7476 Intermediate Similarity NPD7640 Approved
0.7476 Intermediate Similarity NPD7639 Approved
0.7476 Intermediate Similarity NPD5285 Approved
0.7476 Intermediate Similarity NPD5286 Approved
0.7476 Intermediate Similarity NPD4700 Approved
0.7476 Intermediate Similarity NPD4696 Approved
0.7449 Intermediate Similarity NPD4753 Phase 2
0.7447 Intermediate Similarity NPD3667 Approved
0.7431 Intermediate Similarity NPD6617 Approved
0.7431 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD6869 Approved
0.7431 Intermediate Similarity NPD6847 Approved
0.7431 Intermediate Similarity NPD8130 Phase 1
0.7411 Intermediate Similarity NPD7115 Discovery
0.7407 Intermediate Similarity NPD6012 Approved
0.7407 Intermediate Similarity NPD6013 Approved
0.7407 Intermediate Similarity NPD6014 Approved
0.7404 Intermediate Similarity NPD5223 Approved
0.74 Intermediate Similarity NPD4202 Approved
0.7396 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD3617 Approved
0.7391 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD7638 Approved
0.7364 Intermediate Similarity NPD6882 Approved
0.7364 Intermediate Similarity NPD8297 Approved
0.7347 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD6903 Approved
0.7333 Intermediate Similarity NPD5226 Approved
0.7333 Intermediate Similarity NPD5225 Approved
0.7333 Intermediate Similarity NPD5224 Approved
0.7333 Intermediate Similarity NPD4633 Approved
0.7333 Intermediate Similarity NPD7632 Discontinued
0.7327 Intermediate Similarity NPD7748 Approved
0.732 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD7902 Approved
0.7264 Intermediate Similarity NPD4754 Approved
0.7264 Intermediate Similarity NPD5174 Approved
0.7264 Intermediate Similarity NPD5175 Approved
0.7263 Intermediate Similarity NPD4223 Phase 3
0.7263 Intermediate Similarity NPD4221 Approved
0.7255 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD5329 Approved
0.7184 Intermediate Similarity NPD7614 Phase 1
0.7174 Intermediate Similarity NPD6117 Approved
0.7168 Intermediate Similarity NPD6868 Approved
0.7158 Intermediate Similarity NPD4692 Approved
0.7158 Intermediate Similarity NPD4139 Approved
0.7143 Intermediate Similarity NPD5280 Approved
0.7143 Intermediate Similarity NPD6404 Discontinued
0.7143 Intermediate Similarity NPD4694 Approved
0.7143 Intermediate Similarity NPD5690 Phase 2
0.7143 Intermediate Similarity NPD4632 Approved
0.713 Intermediate Similarity NPD6008 Approved
0.713 Intermediate Similarity NPD4767 Approved
0.713 Intermediate Similarity NPD4768 Approved
0.7129 Intermediate Similarity NPD8035 Phase 2
0.7129 Intermediate Similarity NPD6050 Approved
0.7129 Intermediate Similarity NPD8034 Phase 2
0.7113 Intermediate Similarity NPD4197 Approved
0.7111 Intermediate Similarity NPD6081 Approved
0.71 Intermediate Similarity NPD6904 Approved
0.71 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD6080 Approved
0.71 Intermediate Similarity NPD6673 Approved
0.7097 Intermediate Similarity NPD6116 Phase 1
0.7043 Intermediate Similarity NPD6335 Approved
0.7041 Intermediate Similarity NPD1694 Approved
0.7041 Intermediate Similarity NPD5363 Approved
0.703 Intermediate Similarity NPD5207 Approved
0.703 Intermediate Similarity NPD5692 Phase 3
0.703 Intermediate Similarity NPD5785 Approved
0.7021 Intermediate Similarity NPD6115 Approved
0.7021 Intermediate Similarity NPD6114 Approved
0.7021 Intermediate Similarity NPD6697 Approved
0.7021 Intermediate Similarity NPD6118 Approved
0.7018 Intermediate Similarity NPD6274 Approved
0.701 Intermediate Similarity NPD4788 Approved
0.7 Intermediate Similarity NPD5168 Approved
0.7 Intermediate Similarity NPD5128 Approved
0.7 Intermediate Similarity NPD4729 Approved
0.7 Intermediate Similarity NPD4730 Approved
0.699 Remote Similarity NPD7901 Clinical (unspecified phase)
0.699 Remote Similarity NPD7900 Approved
0.6983 Remote Similarity NPD7101 Approved
0.6983 Remote Similarity NPD7100 Approved
0.697 Remote Similarity NPD4138 Approved
0.697 Remote Similarity NPD4693 Phase 3
0.697 Remote Similarity NPD5786 Approved
0.697 Remote Similarity NPD4688 Approved
0.697 Remote Similarity NPD4519 Discontinued
0.697 Remote Similarity NPD4689 Approved
0.697 Remote Similarity NPD4690 Approved
0.697 Remote Similarity NPD5205 Approved
0.697 Remote Similarity NPD4623 Approved
0.6961 Remote Similarity NPD5693 Phase 1
0.6961 Remote Similarity NPD5694 Approved
0.6961 Remote Similarity NPD6411 Approved
0.6957 Remote Similarity NPD6009 Approved
0.6957 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6317 Approved
0.6939 Remote Similarity NPD3668 Phase 3
0.6907 Remote Similarity NPD4269 Approved
0.6907 Remote Similarity NPD4270 Approved
0.6903 Remote Similarity NPD6053 Discontinued
0.6897 Remote Similarity NPD6314 Approved
0.6897 Remote Similarity NPD6313 Approved
0.6893 Remote Similarity NPD5779 Approved
0.6893 Remote Similarity NPD5778 Approved
0.6875 Remote Similarity NPD5250 Approved
0.6875 Remote Similarity NPD5249 Phase 3
0.6875 Remote Similarity NPD5248 Approved
0.6875 Remote Similarity NPD5169 Approved
0.6875 Remote Similarity NPD4634 Approved
0.6875 Remote Similarity NPD5135 Approved
0.6875 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5251 Approved
0.6875 Remote Similarity NPD5247 Approved
0.6864 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6909 Approved
0.6864 Remote Similarity NPD6908 Approved
0.6857 Remote Similarity NPD7732 Phase 3
0.6837 Remote Similarity NPD5362 Discontinued
0.6832 Remote Similarity NPD5208 Approved
0.6827 Remote Similarity NPD6001 Approved
0.6814 Remote Similarity NPD5127 Approved
0.6814 Remote Similarity NPD5215 Approved
0.6814 Remote Similarity NPD5217 Approved
0.6814 Remote Similarity NPD5216 Approved
0.68 Remote Similarity NPD6098 Approved
0.6786 Remote Similarity NPD4061 Clinical (unspecified phase)
0.678 Remote Similarity NPD6319 Approved
0.6774 Remote Similarity NPD5733 Approved
0.6774 Remote Similarity NPD7260 Phase 2
0.6765 Remote Similarity NPD6101 Approved
0.6765 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6762 Remote Similarity NPD5654 Approved
0.6757 Remote Similarity NPD6412 Phase 2
0.675 Remote Similarity NPD7604 Phase 2
0.6739 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6739 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6735 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6733 Remote Similarity NPD3573 Approved
0.6731 Remote Similarity NPD5133 Approved
0.6729 Remote Similarity NPD4225 Approved
0.6726 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6723 Remote Similarity NPD5983 Phase 2
0.672 Remote Similarity NPD6845 Suspended
0.6702 Remote Similarity NPD7339 Approved
0.6702 Remote Similarity NPD3703 Phase 2

  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