Structure

Physi-Chem Properties

Molecular Weight:  514.37
Volume:  555.287
LogP:  6.179
LogD:  4.344
LogS:  -4.068
# Rotatable Bonds:  4
TPSA:  83.83
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.32
Synthetic Accessibility Score:  4.851
Fsp3:  0.875
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:  -5.48
MDCK Permeability:  1.625620097911451e-05
Pgp-inhibitor:  0.274
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.026
20% Bioavailability (F20%):  0.094
30% Bioavailability (F30%):  0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.346
Plasma Protein Binding (PPB):  87.41959381103516%
Volume Distribution (VD):  0.68
Pgp-substrate:  8.175493240356445%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.144
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.669
CYP2C9-inhibitor:  0.162
CYP2C9-substrate:  0.214
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.084
CYP3A4-inhibitor:  0.398
CYP3A4-substrate:  0.23

ADMET: Excretion

Clearance (CL):  1.897
Half-life (T1/2):  0.035

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.559
Drug-inuced Liver Injury (DILI):  0.023
AMES Toxicity:  0.039
Rat Oral Acute Toxicity:  0.414
Maximum Recommended Daily Dose:  0.88
Skin Sensitization:  0.03
Carcinogencity:  0.495
Eye Corrosion:  0.112
Eye Irritation:  0.133
Respiratory Toxicity:  0.978

Download Data

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

  Natural Product: NPC474727

Natural Product ID:  NPC474727
Common Name*:   25-Acetoxy-3R-Hydroxyolean-12-En-28-Oic Acid
IUPAC Name:   (4aS,6aS,6aS,6bR,10R,12aS,14bS)-12a-(acetyloxymethyl)-10-hydroxy-2,2,6a,6b,9,9-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:  
Standard InCHIKey:  FHWNEUNAQWTXBE-LPRJUICTSA-N
Standard InCHI:  InChI=1S/C32H50O5/c1-20(33)37-19-32-13-11-25(34)28(4,5)23(32)10-12-30(7)24(32)9-8-21-22-18-27(2,3)14-16-31(22,26(35)36)17-15-29(21,30)6/h8,22-25,34H,9-19H2,1-7H3,(H,35,36)/t22-,23?,24-,25+,29+,30+,31-,32+/m0/s1
SMILES:  CC(=O)OC[C@]12CC[C@H](C(C)(C)C1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3CC(C)(C)CC[C@@]3(CC[C@@]12C)C(=O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL480497
PubChem CID:   11420932
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
NPO40714 Cones liquidamber styraciflua Strain n.a. n.a. n.a. n.a. n.a. PMID[15270558]
NPO32560 liquidamber styraciflua Species n.a. n.a. n.a. n.a. n.a. PMID[16441087]

☑ 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
NPT306 Cell Line PC-3 Homo sapiens GI50 = 11481.54 nM PMID[470196]
NPT90 Cell Line DU-145 Homo sapiens GI50 = 13182.57 nM PMID[470196]
NPT2723 Cell Line MKN-74 Homo sapiens GI50 = 7762.47 nM PMID[470196]
NPT1097 Cell Line MKN-45 Homo sapiens GI50 = 17782.79 nM PMID[470196]
NPT1179 Cell Line MKN-28 Homo sapiens GI50 = 5623.41 nM PMID[470196]
NPT2722 Cell Line St-4 Homo sapiens GI50 = 9120.11 nM PMID[470196]
NPT369 Cell Line ACHN Homo sapiens GI50 = 5370.32 nM PMID[470196]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 = 20417.38 nM PMID[470196]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 = 11220.18 nM PMID[470196]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 = 18197.01 nM PMID[470196]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 = 10000.0 nM PMID[470196]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 = 10964.78 nM PMID[470196]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 = 11220.18 nM PMID[470196]
NPT576 Cell Line DMS-114 Homo sapiens GI50 = 13489.63 nM PMID[470196]
NPT572 Cell Line DMS-273 Homo sapiens GI50 = 6309.57 nM PMID[470196]
NPT81 Cell Line A549 Homo sapiens GI50 = 4265.8 nM PMID[470196]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 13803.84 nM PMID[470196]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 = 13803.84 nM PMID[470196]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 = 18620.87 nM PMID[470196]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 = 8511.38 nM PMID[470196]
NPT393 Cell Line HCT-116 Homo sapiens GI50 = 4570.88 nM PMID[470196]
NPT148 Cell Line HCT-15 Homo sapiens GI50 = 6456.54 nM PMID[470196]
NPT139 Cell Line HT-29 Homo sapiens GI50 = 3388.44 nM PMID[470196]
NPT386 Cell Line KM12 Homo sapiens GI50 = 5128.61 nM PMID[470196]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 = 28183.83 nM PMID[470196]
NPT578 Cell Line SNB-78 Homo sapiens GI50 = 15848.93 nM PMID[470196]
NPT392 Cell Line SNB-75 Homo sapiens GI50 = 15848.93 nM PMID[470196]
NPT374 Cell Line SF-539 Homo sapiens GI50 = 6309.57 nM PMID[470196]
NPT399 Cell Line SF-295 Homo sapiens GI50 = 8709.64 nM PMID[470196]
NPT395 Cell Line SF-268 Homo sapiens GI50 = 15488.17 nM PMID[470196]
NPT380 Cell Line U-251 Homo sapiens GI50 = 6025.6 nM PMID[470196]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 = 19498.45 nM PMID[470196]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 8317.64 nM PMID[470196]
NPT2398 Cell Line MKN-7 Homo sapiens GI50 = 6606.93 nM PMID[470196]
NPT168 Cell Line P388 Mus musculus ED50 = 28.22 uM PMID[470197]
NPT81 Cell Line A549 Homo sapiens ED50 = 13.31 uM PMID[470197]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 10964.78 nM PMID[470196]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 11748.98 nM PMID[470196]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 10715.19 nM PMID[470196]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 7943.28 nM PMID[470196]

☑ 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 NPC474727 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
0.9778 High Similarity NPC476878
0.9778 High Similarity NPC476879
0.9551 High Similarity NPC86368
0.9545 High Similarity NPC120840
0.9545 High Similarity NPC113989
0.9457 High Similarity NPC260149
0.9457 High Similarity NPC58942
0.9438 High Similarity NPC285184
0.9438 High Similarity NPC77099
0.9438 High Similarity NPC60755
0.9438 High Similarity NPC470590
0.9432 High Similarity NPC30522
0.9326 High Similarity NPC474728
0.9318 High Similarity NPC182797
0.9318 High Similarity NPC246708
0.9318 High Similarity NPC40552
0.9318 High Similarity NPC52169
0.9247 High Similarity NPC475876
0.9239 High Similarity NPC230151
0.9239 High Similarity NPC327179
0.9231 High Similarity NPC78580
0.9231 High Similarity NPC184006
0.9231 High Similarity NPC74751
0.9231 High Similarity NPC23621
0.9231 High Similarity NPC159365
0.9231 High Similarity NPC296164
0.9222 High Similarity NPC475708
0.9213 High Similarity NPC143232
0.9213 High Similarity NPC121798
0.9213 High Similarity NPC263393
0.9213 High Similarity NPC61543
0.9213 High Similarity NPC59263
0.9213 High Similarity NPC225585
0.9213 High Similarity NPC234346
0.9213 High Similarity NPC470588
0.9213 High Similarity NPC290972
0.9213 High Similarity NPC25906
0.9213 High Similarity NPC198664
0.9213 High Similarity NPC127689
0.9213 High Similarity NPC293048
0.9213 High Similarity NPC130520
0.9213 High Similarity NPC270768
0.9213 High Similarity NPC274330
0.9213 High Similarity NPC64872
0.9205 High Similarity NPC162107
0.9205 High Similarity NPC88716
0.9205 High Similarity NPC46912
0.9205 High Similarity NPC18064
0.9205 High Similarity NPC102683
0.9205 High Similarity NPC68160
0.9205 High Similarity NPC51700
0.9205 High Similarity NPC142415
0.9205 High Similarity NPC130577
0.9205 High Similarity NPC242468
0.9205 High Similarity NPC171203
0.9205 High Similarity NPC293564
0.9205 High Similarity NPC307426
0.9205 High Similarity NPC98442
0.913 High Similarity NPC23241
0.913 High Similarity NPC473240
0.913 High Similarity NPC195715
0.9121 High Similarity NPC307335
0.9121 High Similarity NPC295643
0.9121 High Similarity NPC74855
0.9121 High Similarity NPC63118
0.9121 High Similarity NPC474436
0.9121 High Similarity NPC136313
0.9121 High Similarity NPC49776
0.9121 High Similarity NPC214756
0.9121 High Similarity NPC272075
0.9111 High Similarity NPC273621
0.9111 High Similarity NPC470589
0.9111 High Similarity NPC126369
0.9111 High Similarity NPC130278
0.9111 High Similarity NPC111110
0.9111 High Similarity NPC477872
0.9111 High Similarity NPC210037
0.9111 High Similarity NPC7260
0.9111 High Similarity NPC18872
0.9111 High Similarity NPC120968
0.9111 High Similarity NPC290614
0.9111 High Similarity NPC291028
0.9111 High Similarity NPC227467
0.9101 High Similarity NPC181225
0.9101 High Similarity NPC470629
0.9101 High Similarity NPC474512
0.9101 High Similarity NPC473242
0.9101 High Similarity NPC290690
0.9101 High Similarity NPC17733
0.9091 High Similarity NPC10005
0.9091 High Similarity NPC329943
0.9091 High Similarity NPC91525
0.9091 High Similarity NPC72638
0.9091 High Similarity NPC9892
0.9091 High Similarity NPC325594
0.9072 High Similarity NPC477877
0.9043 High Similarity NPC471966
0.9032 High Similarity NPC25848
0.9032 High Similarity NPC476327
0.9032 High Similarity NPC476318
0.9032 High Similarity NPC307282
0.9032 High Similarity NPC19376
0.9032 High Similarity NPC305464
0.9022 High Similarity NPC474963
0.9022 High Similarity NPC91010
0.9011 High Similarity NPC282616
0.9011 High Similarity NPC288833
0.9011 High Similarity NPC235884
0.9011 High Similarity NPC300351
0.9011 High Similarity NPC155120
0.9011 High Similarity NPC84319
0.9011 High Similarity NPC145067
0.9011 High Similarity NPC105189
0.9011 High Similarity NPC4036
0.9011 High Similarity NPC474525
0.9011 High Similarity NPC233455
0.9011 High Similarity NPC324341
0.9011 High Similarity NPC71074
0.9011 High Similarity NPC158030
0.9011 High Similarity NPC52021
0.9011 High Similarity NPC966
0.9011 High Similarity NPC228784
0.9011 High Similarity NPC187722
0.9011 High Similarity NPC306541
0.9011 High Similarity NPC472149
0.9011 High Similarity NPC25299
0.9011 High Similarity NPC65120
0.9 High Similarity NPC474972
0.9 High Similarity NPC475049
0.9 High Similarity NPC161751
0.9 High Similarity NPC95246
0.8977 High Similarity NPC191965
0.8947 High Similarity NPC475156
0.8947 High Similarity NPC473576
0.8936 High Similarity NPC26413
0.8936 High Similarity NPC43686
0.8936 High Similarity NPC158347
0.8936 High Similarity NPC189880
0.8925 High Similarity NPC279974
0.8913 High Similarity NPC275809
0.8913 High Similarity NPC229281
0.8913 High Similarity NPC158059
0.8913 High Similarity NPC118519
0.8913 High Similarity NPC202728
0.8913 High Similarity NPC298554
0.8901 High Similarity NPC86372
0.8901 High Similarity NPC46441
0.8901 High Similarity NPC172361
0.8901 High Similarity NPC193750
0.8901 High Similarity NPC49320
0.8889 High Similarity NPC224145
0.8876 High Similarity NPC84121
0.8876 High Similarity NPC73038
0.8876 High Similarity NPC137306
0.8854 High Similarity NPC476132
0.8854 High Similarity NPC233012
0.8854 High Similarity NPC54909
0.8842 High Similarity NPC164349
0.8842 High Similarity NPC119036
0.883 High Similarity NPC98874
0.8817 High Similarity NPC114159
0.8817 High Similarity NPC231063
0.8817 High Similarity NPC222047
0.8817 High Similarity NPC20235
0.8817 High Similarity NPC282395
0.8817 High Similarity NPC474529
0.8817 High Similarity NPC299996
0.8817 High Similarity NPC6818
0.8817 High Similarity NPC145667
0.8817 High Similarity NPC209868
0.8817 High Similarity NPC191412
0.8817 High Similarity NPC263548
0.8817 High Similarity NPC32407
0.8817 High Similarity NPC88116
0.8804 High Similarity NPC471588
0.8804 High Similarity NPC38754
0.8804 High Similarity NPC6255
0.88 High Similarity NPC237503
0.88 High Similarity NPC167383
0.88 High Similarity NPC57362
0.88 High Similarity NPC306746
0.88 High Similarity NPC204407
0.88 High Similarity NPC310546
0.8791 High Similarity NPC474686
0.8788 High Similarity NPC473538
0.8788 High Similarity NPC283849
0.8778 High Similarity NPC71507
0.8764 High Similarity NPC133954
0.875 High Similarity NPC200752
0.875 High Similarity NPC476195
0.8737 High Similarity NPC259788
0.8737 High Similarity NPC255589
0.8723 High Similarity NPC139570
0.8723 High Similarity NPC148523
0.8723 High Similarity NPC96916
0.8723 High Similarity NPC198245
0.8713 High Similarity NPC279554
0.8713 High Similarity NPC476880
0.8713 High Similarity NPC476884
0.8713 High Similarity NPC136877

  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 NPC474727 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
0.9231 High Similarity NPD7748 Approved
0.9011 High Similarity NPD7515 Phase 2
0.8936 High Similarity NPD7902 Approved
0.8617 High Similarity NPD7900 Approved
0.8617 High Similarity NPD7901 Clinical (unspecified phase)
0.8265 Intermediate Similarity NPD7638 Approved
0.8211 Intermediate Similarity NPD8035 Phase 2
0.8211 Intermediate Similarity NPD8034 Phase 2
0.8182 Intermediate Similarity NPD7640 Approved
0.8182 Intermediate Similarity NPD7639 Approved
0.8152 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.809 Intermediate Similarity NPD7645 Phase 2
0.7938 Intermediate Similarity NPD6399 Phase 3
0.7905 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7788 Intermediate Similarity NPD8328 Phase 3
0.7727 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD3618 Phase 1
0.766 Intermediate Similarity NPD4786 Approved
0.7634 Intermediate Similarity NPD3667 Approved
0.7629 Intermediate Similarity NPD5328 Approved
0.7619 Intermediate Similarity NPD6675 Approved
0.7619 Intermediate Similarity NPD6402 Approved
0.7619 Intermediate Similarity NPD7128 Approved
0.7619 Intermediate Similarity NPD5739 Approved
0.75 Intermediate Similarity NPD6684 Approved
0.75 Intermediate Similarity NPD7632 Discontinued
0.75 Intermediate Similarity NPD7334 Approved
0.75 Intermediate Similarity NPD7521 Approved
0.75 Intermediate Similarity NPD6409 Approved
0.75 Intermediate Similarity NPD7146 Approved
0.75 Intermediate Similarity NPD5330 Approved
0.7477 Intermediate Similarity NPD6881 Approved
0.7477 Intermediate Similarity NPD7320 Approved
0.7477 Intermediate Similarity NPD6899 Approved
0.7475 Intermediate Similarity NPD6079 Approved
0.7475 Intermediate Similarity NPD6411 Approved
0.7451 Intermediate Similarity NPD6083 Phase 2
0.7451 Intermediate Similarity NPD6084 Phase 2
0.7449 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD8130 Phase 1
0.7423 Intermediate Similarity NPD3573 Approved
0.7407 Intermediate Similarity NPD6372 Approved
0.7407 Intermediate Similarity NPD6373 Approved
0.7391 Intermediate Similarity NPD6118 Approved
0.7391 Intermediate Similarity NPD6115 Approved
0.7391 Intermediate Similarity NPD6114 Approved
0.7391 Intermediate Similarity NPD6697 Approved
0.7383 Intermediate Similarity NPD6412 Phase 2
0.7383 Intermediate Similarity NPD5701 Approved
0.7383 Intermediate Similarity NPD5697 Approved
0.7364 Intermediate Similarity NPD8297 Approved
0.7347 Intermediate Similarity NPD6672 Approved
0.7347 Intermediate Similarity NPD5737 Approved
0.7347 Intermediate Similarity NPD6903 Approved
0.7339 Intermediate Similarity NPD7102 Approved
0.7339 Intermediate Similarity NPD6883 Approved
0.7339 Intermediate Similarity NPD7290 Approved
0.7315 Intermediate Similarity NPD6011 Approved
0.7297 Intermediate Similarity NPD4632 Approved
0.7297 Intermediate Similarity NPD8133 Approved
0.7292 Intermediate Similarity NPD3133 Approved
0.7292 Intermediate Similarity NPD3666 Approved
0.7292 Intermediate Similarity NPD3665 Phase 1
0.729 Intermediate Similarity NPD6008 Approved
0.7273 Intermediate Similarity NPD6617 Approved
0.7273 Intermediate Similarity NPD6869 Approved
0.7273 Intermediate Similarity NPD6649 Approved
0.7273 Intermediate Similarity NPD6847 Approved
0.7273 Intermediate Similarity NPD6650 Approved
0.7273 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6101 Approved
0.7273 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD6014 Approved
0.7248 Intermediate Similarity NPD6013 Approved
0.7248 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD6012 Approved
0.7234 Intermediate Similarity NPD7525 Registered
0.7228 Intermediate Similarity NPD5778 Approved
0.7228 Intermediate Similarity NPD5779 Approved
0.7228 Intermediate Similarity NPD4202 Approved
0.7227 Intermediate Similarity NPD7736 Approved
0.7207 Intermediate Similarity NPD6882 Approved
0.7184 Intermediate Similarity NPD4697 Phase 3
0.7184 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD5221 Approved
0.7184 Intermediate Similarity NPD5222 Approved
0.7174 Intermediate Similarity NPD6117 Approved
0.7156 Intermediate Similarity NPD6686 Approved
0.7115 Intermediate Similarity NPD5173 Approved
0.7115 Intermediate Similarity NPD4755 Approved
0.7113 Intermediate Similarity NPD3668 Phase 3
0.7105 Intermediate Similarity NPD6009 Approved
0.7105 Intermediate Similarity NPD7115 Discovery
0.7097 Intermediate Similarity NPD6116 Phase 1
0.7087 Intermediate Similarity NPD5695 Phase 3
0.7087 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD6319 Approved
0.7059 Intermediate Similarity NPD7507 Approved
0.7048 Intermediate Similarity NPD5696 Approved
0.7034 Intermediate Similarity NPD7604 Phase 2
0.7027 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD7614 Phase 1
0.7019 Intermediate Similarity NPD7732 Phase 3
0.7018 Intermediate Similarity NPD6868 Approved
0.7009 Intermediate Similarity NPD5983 Phase 2
0.7 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8293 Discontinued
0.6981 Remote Similarity NPD5286 Approved
0.6981 Remote Similarity NPD5285 Approved
0.6981 Remote Similarity NPD4700 Approved
0.6981 Remote Similarity NPD4696 Approved
0.6975 Remote Similarity NPD7492 Approved
0.697 Remote Similarity NPD6098 Approved
0.6957 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6931 Remote Similarity NPD6904 Approved
0.6931 Remote Similarity NPD6080 Approved
0.6931 Remote Similarity NPD6673 Approved
0.6931 Remote Similarity NPD4753 Phase 2
0.6923 Remote Similarity NPD8377 Approved
0.6923 Remote Similarity NPD6059 Approved
0.6923 Remote Similarity NPD8294 Approved
0.6923 Remote Similarity NPD6054 Approved
0.6917 Remote Similarity NPD6616 Approved
0.6917 Remote Similarity NPD6336 Discontinued
0.6916 Remote Similarity NPD5223 Approved
0.6907 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6335 Approved
0.6887 Remote Similarity NPD4225 Approved
0.6885 Remote Similarity NPD7319 Approved
0.6882 Remote Similarity NPD7339 Approved
0.6882 Remote Similarity NPD6942 Approved
0.6875 Remote Similarity NPD4695 Discontinued
0.687 Remote Similarity NPD6274 Approved
0.6864 Remote Similarity NPD8380 Approved
0.6864 Remote Similarity NPD8033 Approved
0.6864 Remote Similarity NPD8379 Approved
0.6864 Remote Similarity NPD8296 Approved
0.6864 Remote Similarity NPD8378 Approved
0.6864 Remote Similarity NPD8335 Approved
0.686 Remote Similarity NPD7078 Approved
0.6852 Remote Similarity NPD4633 Approved
0.6852 Remote Similarity NPD5226 Approved
0.6852 Remote Similarity NPD5225 Approved
0.6852 Remote Similarity NPD5211 Phase 2
0.6852 Remote Similarity NPD5224 Approved
0.6838 Remote Similarity NPD7101 Approved
0.6838 Remote Similarity NPD7100 Approved
0.681 Remote Similarity NPD6317 Approved
0.6809 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6807 Remote Similarity NPD6370 Approved
0.68 Remote Similarity NPD3574 Clinical (unspecified phase)
0.68 Remote Similarity NPD5279 Phase 3
0.6796 Remote Similarity NPD7637 Suspended
0.6789 Remote Similarity NPD5175 Approved
0.6789 Remote Similarity NPD5174 Approved
0.6789 Remote Similarity NPD4754 Approved
0.6757 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6752 Remote Similarity NPD7327 Approved
0.6752 Remote Similarity NPD7328 Approved
0.6752 Remote Similarity NPD6314 Approved
0.6752 Remote Similarity NPD6313 Approved
0.675 Remote Similarity NPD6067 Discontinued
0.6735 Remote Similarity NPD4221 Approved
0.6735 Remote Similarity NPD4223 Phase 3
0.6727 Remote Similarity NPD5141 Approved
0.6726 Remote Similarity NPD4634 Approved
0.6723 Remote Similarity NPD6909 Approved
0.6723 Remote Similarity NPD6908 Approved
0.6723 Remote Similarity NPD6015 Approved
0.6723 Remote Similarity NPD6016 Approved
0.6702 Remote Similarity NPD3703 Phase 2
0.67 Remote Similarity NPD5329 Approved
0.67 Remote Similarity NPD1694 Approved
0.6695 Remote Similarity NPD7516 Approved
0.6667 Remote Similarity NPD5208 Approved
0.6667 Remote Similarity NPD4788 Approved
0.6667 Remote Similarity NPD5988 Approved
0.6667 Remote Similarity NPD4768 Approved
0.6667 Remote Similarity NPD6001 Approved
0.6667 Remote Similarity NPD4767 Approved
0.6635 Remote Similarity NPD5693 Phase 1
0.6635 Remote Similarity NPD5284 Approved
0.6635 Remote Similarity NPD5281 Approved
0.6635 Remote Similarity NPD6050 Approved
0.6609 Remote Similarity NPD6053 Discontinued
0.6604 Remote Similarity NPD5210 Approved
0.6604 Remote Similarity NPD4629 Approved
0.6602 Remote Similarity NPD6051 Approved
0.66 Remote Similarity NPD4197 Approved
0.6583 Remote Similarity NPD8516 Approved
0.6583 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6583 Remote Similarity NPD8515 Approved
0.6583 Remote Similarity NPD8517 Approved
0.6583 Remote Similarity NPD7503 Approved
0.6583 Remote Similarity NPD8513 Phase 3
0.6559 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6559 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6549 Remote Similarity NPD4729 Approved
0.6549 Remote Similarity NPD5168 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