Structure

Physi-Chem Properties

Molecular Weight:  456.32
Volume:  494.609
LogP:  4.048
LogD:  3.607
LogS:  -4.124
# Rotatable Bonds:  2
TPSA:  77.76
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.463
Synthetic Accessibility Score:  4.925
Fsp3:  0.828
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:  -5.509
MDCK Permeability:  6.683377705485327e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.961
30% Bioavailability (F30%):  0.576

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.862
Plasma Protein Binding (PPB):  82.1705551147461%
Volume Distribution (VD):  0.537
Pgp-substrate:  13.913347244262695%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.288
CYP2C19-inhibitor:  0.006
CYP2C19-substrate:  0.75
CYP2C9-inhibitor:  0.05
CYP2C9-substrate:  0.097
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.151
CYP3A4-inhibitor:  0.37
CYP3A4-substrate:  0.167

ADMET: Excretion

Clearance (CL):  2.616
Half-life (T1/2):  0.344

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.487
Drug-inuced Liver Injury (DILI):  0.025
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.952
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.115
Carcinogencity:  0.367
Eye Corrosion:  0.12
Eye Irritation:  0.19
Respiratory Toxicity:  0.983

Download Data

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Similar NPs/Drugs  

  Natural Product: NPC130520

Natural Product ID:  NPC130520
Common Name*:   30-Norhederagenin
IUPAC Name:   (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-6a,6b,9,12a-tetramethyl-2-methylidene-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:   30-Norhederagenin
Standard InCHIKey:  FKUBIEWSGBVADJ-VZBPFLCRSA-N
Standard InCHI:  InChI=1S/C29H44O4/c1-18-8-13-29(24(32)33)15-14-27(4)19(20(29)16-18)6-7-22-25(2)11-10-23(31)26(3,17-30)21(25)9-12-28(22,27)5/h6,20-23,30-31H,1,7-17H2,2-5H3,(H,32,33)/t20-,21+,22+,23-,25-,26-,27+,28+,29-/m0/s1
SMILES:  OC[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(=C)CC1)C(=O)O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1081326
PubChem CID:   21596158
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid 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
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Anhui province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Gansu province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Henan province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Shandong province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Shanxi province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. DOI[10.2174/092986712800229032]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. PMID[11339628]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. bark n.a. PMID[17260795]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. PMID[19402674]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. Daejeon, Korea 2007-Jan PMID[19670875]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[19721258]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[19772486]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[20806783]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[20822014]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[21782011]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota roots Whitessence Srl, Viterbo, Italy 2005-OCT PMID[21954959]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. root n.a. PMID[21954959]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[22190295]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. root n.a. PMID[22547314]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota root bark Bozhou, Anhui Province, China 2010-AUG PMID[24377852]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. flower n.a. PMID[24504864]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota Flowers LuoYang, HeNan, China n.a. PMID[24621197]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[26838074]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[27313650]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[27429639]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[29741372]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds DingXi, GanSu, China early autumn (from August to the beginning of September PMID[32545196]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds LanZhou, GanSu, China early autumn (from August to the beginning of September PMID[32545196]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds HeZe, ShanDong, China early autumn (from August to the beginning of September PMID[32545196]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[32951423]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Xinjiang,China PMID[33063333]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China Maturation PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 10 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 20 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 30 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 40 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 10 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 50 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 20 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 60 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 30 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 70 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 40 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 50 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 80 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 60 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 90 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China Maturation PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 70 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 80 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 90 days after pollination PMID[33131958]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21458 Radix paeoniae rubra Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15265 Paeonia rockii Species Paeoniaceae 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 Survival = 65.0 % PMID[518774]
NPT65 Cell Line HepG2 Homo sapiens Survival = 84.6 % PMID[518774]
NPT65 Cell Line HepG2 Homo sapiens Survival = 96.7 % PMID[518774]
NPT65 Cell Line HepG2 Homo sapiens Survival = 100.0 % PMID[518774]
NPT203 Individual Protein Carboxylesterase 2 Homo sapiens IC50 = 1900.0 nM PMID[518776]
NPT166 Individual Protein Acyl coenzyme A:cholesterol acyltransferase Homo sapiens IC50 = 100.0 nM PMID[518776]
NPT68 Individual Protein Aldose reductase Rattus norvegicus IC50 = 28800.0 nM PMID[518775]
NPT35 Others n.a. IC50 > 500000.0 nM PMID[518775]
NPT2 Others Unspecified Ratio IC50 = 30.0 n.a. PMID[518776]

☑ 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 NPC130520 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
1.0 High Similarity NPC263393
1.0 High Similarity NPC234346
1.0 High Similarity NPC225585
1.0 High Similarity NPC293048
1.0 High Similarity NPC121798
1.0 High Similarity NPC270768
1.0 High Similarity NPC61543
1.0 High Similarity NPC59263
1.0 High Similarity NPC127689
0.9881 High Similarity NPC126369
0.9881 High Similarity NPC470589
0.9881 High Similarity NPC130278
0.9881 High Similarity NPC111110
0.988 High Similarity NPC52169
0.988 High Similarity NPC182797
0.9765 High Similarity NPC228784
0.9765 High Similarity NPC155120
0.9765 High Similarity NPC324341
0.9765 High Similarity NPC282616
0.9765 High Similarity NPC288833
0.9765 High Similarity NPC966
0.9762 High Similarity NPC274330
0.9762 High Similarity NPC198664
0.9762 High Similarity NPC143232
0.9762 High Similarity NPC64872
0.9762 High Similarity NPC290972
0.9762 High Similarity NPC25906
0.9759 High Similarity NPC98442
0.9759 High Similarity NPC307426
0.9759 High Similarity NPC293564
0.9759 High Similarity NPC130577
0.9759 High Similarity NPC51700
0.9759 High Similarity NPC88716
0.9759 High Similarity NPC68160
0.9759 High Similarity NPC242468
0.9759 High Similarity NPC142415
0.9759 High Similarity NPC171203
0.9759 High Similarity NPC102683
0.9759 High Similarity NPC18064
0.9651 High Similarity NPC229281
0.9651 High Similarity NPC86368
0.9647 High Similarity NPC210037
0.9647 High Similarity NPC290614
0.9647 High Similarity NPC291028
0.9647 High Similarity NPC120968
0.9647 High Similarity NPC86372
0.9647 High Similarity NPC273621
0.9647 High Similarity NPC18872
0.9647 High Similarity NPC227467
0.9647 High Similarity NPC172361
0.9647 High Similarity NPC477872
0.9647 High Similarity NPC7260
0.9643 High Similarity NPC17733
0.9643 High Similarity NPC290690
0.9643 High Similarity NPC470629
0.9643 High Similarity NPC246708
0.9643 High Similarity NPC473242
0.9643 High Similarity NPC40552
0.9643 High Similarity NPC181225
0.9643 High Similarity NPC474512
0.9639 High Similarity NPC72638
0.954 High Similarity NPC6818
0.954 High Similarity NPC222047
0.954 High Similarity NPC191412
0.954 High Similarity NPC145667
0.954 High Similarity NPC88116
0.954 High Similarity NPC299996
0.954 High Similarity NPC231063
0.954 High Similarity NPC114159
0.954 High Similarity NPC282395
0.954 High Similarity NPC263548
0.954 High Similarity NPC159365
0.954 High Similarity NPC20235
0.954 High Similarity NPC32407
0.9535 High Similarity NPC187722
0.9535 High Similarity NPC105189
0.9535 High Similarity NPC65120
0.9535 High Similarity NPC471588
0.9535 High Similarity NPC158030
0.9535 High Similarity NPC71074
0.9535 High Similarity NPC306541
0.9535 High Similarity NPC235884
0.9535 High Similarity NPC84319
0.9535 High Similarity NPC300351
0.9535 High Similarity NPC4036
0.9535 High Similarity NPC25299
0.9535 High Similarity NPC52021
0.9535 High Similarity NPC145067
0.9535 High Similarity NPC6255
0.9535 High Similarity NPC472149
0.9535 High Similarity NPC233455
0.9535 High Similarity NPC474525
0.9535 High Similarity NPC475708
0.9529 High Similarity NPC470588
0.9529 High Similarity NPC474972
0.9529 High Similarity NPC161751
0.9529 High Similarity NPC95246
0.9432 High Similarity NPC148523
0.9425 High Similarity NPC214756
0.9425 High Similarity NPC307335
0.9425 High Similarity NPC298554
0.9425 High Similarity NPC158059
0.9425 High Similarity NPC202728
0.9425 High Similarity NPC136313
0.9425 High Similarity NPC295643
0.9425 High Similarity NPC272075
0.9425 High Similarity NPC118490
0.9425 High Similarity NPC275809
0.9425 High Similarity NPC118519
0.9425 High Similarity NPC74855
0.9419 High Similarity NPC474728
0.9419 High Similarity NPC46441
0.9419 High Similarity NPC193750
0.9419 High Similarity NPC120840
0.9419 High Similarity NPC113989
0.9419 High Similarity NPC49320
0.9405 High Similarity NPC213412
0.9326 High Similarity NPC116457
0.9326 High Similarity NPC476318
0.9326 High Similarity NPC307282
0.9326 High Similarity NPC204961
0.9326 High Similarity NPC173744
0.9326 High Similarity NPC25848
0.9326 High Similarity NPC19376
0.9326 High Similarity NPC305464
0.9326 High Similarity NPC476327
0.9326 High Similarity NPC73004
0.9326 High Similarity NPC201657
0.9326 High Similarity NPC98874
0.9326 High Similarity NPC132824
0.9318 High Similarity NPC474529
0.9318 High Similarity NPC80365
0.9318 High Similarity NPC91010
0.9318 High Similarity NPC78580
0.9318 High Similarity NPC209868
0.9318 High Similarity NPC23621
0.9318 High Similarity NPC184006
0.931 High Similarity NPC38754
0.931 High Similarity NPC77099
0.931 High Similarity NPC60755
0.931 High Similarity NPC470590
0.931 High Similarity NPC285184
0.9302 High Similarity NPC474686
0.9302 High Similarity NPC30522
0.9294 High Similarity NPC71507
0.9286 High Similarity NPC133954
0.9222 High Similarity NPC476878
0.9222 High Similarity NPC247139
0.9222 High Similarity NPC9613
0.9222 High Similarity NPC106112
0.9222 High Similarity NPC261935
0.9222 High Similarity NPC476879
0.9213 High Similarity NPC96916
0.9213 High Similarity NPC473240
0.9213 High Similarity NPC474727
0.9213 High Similarity NPC139570
0.9213 High Similarity NPC83693
0.9213 High Similarity NPC32118
0.9213 High Similarity NPC195715
0.9213 High Similarity NPC23241
0.9213 High Similarity NPC198245
0.9205 High Similarity NPC474436
0.9205 High Similarity NPC63118
0.9205 High Similarity NPC474806
0.9205 High Similarity NPC49776
0.9205 High Similarity NPC133579
0.9176 High Similarity NPC95594
0.9176 High Similarity NPC73038
0.9176 High Similarity NPC475862
0.9176 High Similarity NPC74363
0.9176 High Similarity NPC477579
0.9176 High Similarity NPC235341
0.9167 High Similarity NPC171789
0.9121 High Similarity NPC174663
0.9121 High Similarity NPC111214
0.9121 High Similarity NPC271614
0.9121 High Similarity NPC164349
0.9121 High Similarity NPC29765
0.9111 High Similarity NPC157113
0.9111 High Similarity NPC207922
0.9111 High Similarity NPC62516
0.9111 High Similarity NPC259733
0.9111 High Similarity NPC327179
0.9111 High Similarity NPC158371
0.9111 High Similarity NPC230151
0.9101 High Similarity NPC60692
0.9101 High Similarity NPC87095
0.9101 High Similarity NPC188102
0.9101 High Similarity NPC296164
0.9101 High Similarity NPC74751
0.9091 High Similarity NPC301244
0.908 High Similarity NPC281524
0.908 High Similarity NPC475921
0.908 High Similarity NPC474704
0.907 High Similarity NPC46912
0.907 High Similarity NPC158141
0.907 High Similarity NPC173089
0.907 High Similarity NPC73064
0.907 High Similarity NPC162107
0.9022 High Similarity NPC35239

  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 NPC130520 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
0.9535 High Similarity NPD7515 Phase 2
0.9101 High Similarity NPD7748 Approved
0.8804 High Similarity NPD7902 Approved
0.8621 High Similarity NPD7520 Clinical (unspecified phase)
0.8571 High Similarity NPD7645 Phase 2
0.8478 Intermediate Similarity NPD7900 Approved
0.8478 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.8111 Intermediate Similarity NPD3618 Phase 1
0.809 Intermediate Similarity NPD4786 Approved
0.8068 Intermediate Similarity NPD3667 Approved
0.8065 Intermediate Similarity NPD8034 Phase 2
0.8065 Intermediate Similarity NPD8035 Phase 2
0.8043 Intermediate Similarity NPD5328 Approved
0.7979 Intermediate Similarity NPD6399 Phase 3
0.7872 Intermediate Similarity NPD6079 Approved
0.7849 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7822 Intermediate Similarity NPD6675 Approved
0.7822 Intermediate Similarity NPD6402 Approved
0.7822 Intermediate Similarity NPD7128 Approved
0.7822 Intermediate Similarity NPD5739 Approved
0.7755 Intermediate Similarity NPD7638 Approved
0.7742 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD3666 Approved
0.7692 Intermediate Similarity NPD3665 Phase 1
0.7692 Intermediate Similarity NPD3133 Approved
0.7684 Intermediate Similarity NPD6411 Approved
0.7677 Intermediate Similarity NPD7640 Approved
0.7677 Intermediate Similarity NPD7639 Approved
0.767 Intermediate Similarity NPD6881 Approved
0.767 Intermediate Similarity NPD6899 Approved
0.767 Intermediate Similarity NPD7320 Approved
0.7653 Intermediate Similarity NPD4755 Approved
0.7653 Intermediate Similarity NPD6083 Phase 2
0.7653 Intermediate Similarity NPD6084 Phase 2
0.764 Intermediate Similarity NPD7525 Registered
0.7604 Intermediate Similarity NPD4202 Approved
0.7596 Intermediate Similarity NPD6372 Approved
0.7596 Intermediate Similarity NPD6373 Approved
0.7586 Intermediate Similarity NPD6117 Approved
0.7573 Intermediate Similarity NPD5701 Approved
0.7573 Intermediate Similarity NPD5697 Approved
0.7551 Intermediate Similarity NPD5222 Approved
0.7551 Intermediate Similarity NPD4697 Phase 3
0.7551 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD5221 Approved
0.7527 Intermediate Similarity NPD6684 Approved
0.7527 Intermediate Similarity NPD7334 Approved
0.7527 Intermediate Similarity NPD5330 Approved
0.7527 Intermediate Similarity NPD7521 Approved
0.7527 Intermediate Similarity NPD6409 Approved
0.7527 Intermediate Similarity NPD7146 Approved
0.7524 Intermediate Similarity NPD7102 Approved
0.7524 Intermediate Similarity NPD7290 Approved
0.7524 Intermediate Similarity NPD6883 Approved
0.75 Intermediate Similarity NPD5286 Approved
0.75 Intermediate Similarity NPD3668 Phase 3
0.75 Intermediate Similarity NPD6116 Phase 1
0.75 Intermediate Similarity NPD4700 Approved
0.75 Intermediate Similarity NPD4696 Approved
0.75 Intermediate Similarity NPD5285 Approved
0.7475 Intermediate Similarity NPD5173 Approved
0.7474 Intermediate Similarity NPD6101 Approved
0.7474 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD4753 Phase 2
0.7453 Intermediate Similarity NPD8130 Phase 1
0.7453 Intermediate Similarity NPD6617 Approved
0.7453 Intermediate Similarity NPD6650 Approved
0.7453 Intermediate Similarity NPD6869 Approved
0.7453 Intermediate Similarity NPD6649 Approved
0.7453 Intermediate Similarity NPD6847 Approved
0.7447 Intermediate Similarity NPD3573 Approved
0.7429 Intermediate Similarity NPD6012 Approved
0.7429 Intermediate Similarity NPD6014 Approved
0.7429 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD6013 Approved
0.7416 Intermediate Similarity NPD6114 Approved
0.7416 Intermediate Similarity NPD6697 Approved
0.7416 Intermediate Similarity NPD6115 Approved
0.7416 Intermediate Similarity NPD6118 Approved
0.7383 Intermediate Similarity NPD6882 Approved
0.7383 Intermediate Similarity NPD8297 Approved
0.7374 Intermediate Similarity NPD7614 Phase 1
0.7368 Intermediate Similarity NPD6903 Approved
0.7368 Intermediate Similarity NPD6672 Approved
0.7368 Intermediate Similarity NPD5737 Approved
0.7356 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD5224 Approved
0.7353 Intermediate Similarity NPD5211 Phase 2
0.7353 Intermediate Similarity NPD5226 Approved
0.7353 Intermediate Similarity NPD5225 Approved
0.7353 Intermediate Similarity NPD4633 Approved
0.7345 Intermediate Similarity NPD8328 Phase 3
0.7333 Intermediate Similarity NPD6011 Approved
0.729 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD5175 Approved
0.7282 Intermediate Similarity NPD5174 Approved
0.7273 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7339 Approved
0.7273 Intermediate Similarity NPD7115 Discovery
0.7273 Intermediate Similarity NPD5695 Phase 3
0.7273 Intermediate Similarity NPD6942 Approved
0.7255 Intermediate Similarity NPD5223 Approved
0.7253 Intermediate Similarity NPD4695 Discontinued
0.7228 Intermediate Similarity NPD5696 Approved
0.7212 Intermediate Similarity NPD5141 Approved
0.7191 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD5279 Phase 3
0.7143 Intermediate Similarity NPD4767 Approved
0.7143 Intermediate Similarity NPD4768 Approved
0.7115 Intermediate Similarity NPD4754 Approved
0.71 Intermediate Similarity NPD4629 Approved
0.71 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD5210 Approved
0.7097 Intermediate Similarity NPD4221 Approved
0.7097 Intermediate Similarity NPD4223 Phase 3
0.7075 Intermediate Similarity NPD6412 Phase 2
0.7071 Intermediate Similarity NPD5778 Approved
0.7071 Intermediate Similarity NPD5779 Approved
0.7059 Intermediate Similarity NPD4225 Approved
0.7053 Intermediate Similarity NPD5329 Approved
0.703 Intermediate Similarity NPD7732 Phase 3
0.7027 Intermediate Similarity NPD6274 Approved
0.7027 Intermediate Similarity NPD6868 Approved
0.7021 Intermediate Similarity NPD4788 Approved
0.7019 Intermediate Similarity NPD7632 Discontinued
0.7009 Intermediate Similarity NPD4729 Approved
0.7009 Intermediate Similarity NPD4730 Approved
0.7009 Intermediate Similarity NPD5128 Approved
0.7 Intermediate Similarity NPD4632 Approved
0.6991 Remote Similarity NPD7100 Approved
0.6991 Remote Similarity NPD7101 Approved
0.6979 Remote Similarity NPD6098 Approved
0.697 Remote Similarity NPD5281 Approved
0.697 Remote Similarity NPD5284 Approved
0.6947 Remote Similarity NPD4197 Approved
0.6944 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6673 Approved
0.6939 Remote Similarity NPD6904 Approved
0.6939 Remote Similarity NPD6080 Approved
0.6932 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6932 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6915 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6903 Remote Similarity NPD6335 Approved
0.6897 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6897 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6881 Remote Similarity NPD4634 Approved
0.6881 Remote Similarity NPD5249 Phase 3
0.6881 Remote Similarity NPD5247 Approved
0.6881 Remote Similarity NPD5248 Approved
0.6881 Remote Similarity NPD5250 Approved
0.6881 Remote Similarity NPD5251 Approved
0.687 Remote Similarity NPD6909 Approved
0.687 Remote Similarity NPD6908 Approved
0.6852 Remote Similarity NPD6686 Approved
0.6852 Remote Similarity NPD5168 Approved
0.6848 Remote Similarity NPD3617 Approved
0.6848 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6847 Remote Similarity NPD8133 Approved
0.6822 Remote Similarity NPD6008 Approved
0.6818 Remote Similarity NPD5215 Approved
0.6818 Remote Similarity NPD5217 Approved
0.6818 Remote Similarity NPD5216 Approved
0.6814 Remote Similarity NPD6009 Approved
0.6814 Remote Similarity NPD6317 Approved
0.6807 Remote Similarity NPD7736 Approved
0.6804 Remote Similarity NPD4138 Approved
0.6804 Remote Similarity NPD5205 Approved
0.6804 Remote Similarity NPD4688 Approved
0.6804 Remote Similarity NPD4689 Approved
0.6804 Remote Similarity NPD4623 Approved
0.6804 Remote Similarity NPD4519 Discontinued
0.6804 Remote Similarity NPD4690 Approved
0.6804 Remote Similarity NPD4693 Phase 3
0.6783 Remote Similarity NPD6319 Approved
0.678 Remote Similarity NPD7507 Approved
0.6754 Remote Similarity NPD6314 Approved
0.6754 Remote Similarity NPD6313 Approved
0.6727 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6727 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6727 Remote Similarity NPD5135 Approved
0.6727 Remote Similarity NPD5169 Approved
0.6703 Remote Similarity NPD3703 Phase 2
0.6702 Remote Similarity NPD5368 Approved
0.6702 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6701 Remote Similarity NPD1694 Approved
0.6697 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6695 Remote Similarity NPD7492 Approved
0.6667 Remote Similarity NPD5127 Approved
0.6667 Remote Similarity NPD5208 Approved
0.6667 Remote Similarity NPD6001 Approved
0.6639 Remote Similarity NPD6616 Approved
0.6638 Remote Similarity NPD6059 Approved
0.6638 Remote Similarity NPD6054 Approved
0.6634 Remote Similarity NPD7637 Suspended
0.6634 Remote Similarity NPD5693 Phase 1
0.6634 Remote Similarity NPD6050 Approved
0.6633 Remote Similarity NPD5280 Approved
0.6633 Remote Similarity NPD5690 Phase 2
0.6633 Remote Similarity NPD4694 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