Structure

Physi-Chem Properties

Molecular Weight:  238.19
Volume:  265.827
LogP:  3.512
LogD:  3.489
LogS:  -3.609
# Rotatable Bonds:  1
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.69
Synthetic Accessibility Score:  4.446
Fsp3:  0.867
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:  -4.414
MDCK Permeability:  1.587400220159907e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.29
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.943
30% Bioavailability (F30%):  0.418

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.169
Plasma Protein Binding (PPB):  94.06229400634766%
Volume Distribution (VD):  1.161
Pgp-substrate:  3.612647294998169%

ADMET: Metabolism

CYP1A2-inhibitor:  0.142
CYP1A2-substrate:  0.265
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.814
CYP2C9-inhibitor:  0.079
CYP2C9-substrate:  0.722
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.228
CYP3A4-inhibitor:  0.159
CYP3A4-substrate:  0.314

ADMET: Excretion

Clearance (CL):  8.984
Half-life (T1/2):  0.45

ADMET: Toxicity

hERG Blockers:  0.049
Human Hepatotoxicity (H-HT):  0.229
Drug-inuced Liver Injury (DILI):  0.076
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.044
Maximum Recommended Daily Dose:  0.022
Skin Sensitization:  0.421
Carcinogencity:  0.031
Eye Corrosion:  0.477
Eye Irritation:  0.876
Respiratory Toxicity:  0.532

Download Data

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

  Natural Product: NPC220939

Natural Product ID:  NPC220939
Common Name*:   (+)-(1R,5R,6R,7S,10R)-Cadinan-3-Ene-1,5-Diol
IUPAC Name:   (1R,4aR,5R,8S,8aR)-2,5-dimethyl-8-propan-2-yl-4,5,6,7,8,8a-hexahydro-1H-naphthalene-1,4a-diol
Synonyms:  
Standard InCHIKey:  DICWRYPRNPIQED-QKGCVVFFSA-N
Standard InCHI:  InChI=1S/C15H26O2/c1-9(2)12-6-5-11(4)15(17)8-7-10(3)14(16)13(12)15/h7,9,11-14,16-17H,5-6,8H2,1-4H3/t11-,12+,13-,14+,15-/m1/s1
SMILES:  CC(C)[C@@H]1CC[C@@H](C)[C@@]2(CC=C(C)[C@@H]([C@@H]12)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463553
PubChem CID:   11160763
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO29315 Dictyopteris divaricata Species Dictyotaceae Eukaryota n.a. n.a. n.a. PMID[15497933]
NPO29315 Dictyopteris divaricata Species Dictyotaceae Eukaryota n.a. n.a. n.a. PMID[16180804]
NPO29315 Dictyopteris divaricata Species Dictyotaceae Eukaryota n.a. n.a. n.a. PMID[16989516]
NPO29315 Dictyopteris divaricata Species Dictyotaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[543830]
NPT547 Cell Line BGC-823 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[543830]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[543830]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[543830]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[543830]

☑ 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 NPC220939 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 NPC265485
0.9559 High Similarity NPC23954
0.9104 High Similarity NPC202017
0.9028 High Similarity NPC265588
0.9 High Similarity NPC242992
0.8857 High Similarity NPC92801
0.8841 High Similarity NPC96484
0.875 High Similarity NPC201048
0.875 High Similarity NPC476366
0.8732 High Similarity NPC164022
0.8732 High Similarity NPC477792
0.8649 High Similarity NPC91594
0.8649 High Similarity NPC470711
0.8649 High Similarity NPC470758
0.8592 High Similarity NPC34834
0.8571 High Similarity NPC276616
0.8551 High Similarity NPC326310
0.8514 High Similarity NPC470749
0.8507 High Similarity NPC282694
0.8507 High Similarity NPC79576
0.8507 High Similarity NPC194208
0.8472 Intermediate Similarity NPC471272
0.8472 Intermediate Similarity NPC167706
0.8451 Intermediate Similarity NPC474248
0.8442 Intermediate Similarity NPC249423
0.8442 Intermediate Similarity NPC476646
0.84 Intermediate Similarity NPC477425
0.84 Intermediate Similarity NPC477427
0.84 Intermediate Similarity NPC474826
0.84 Intermediate Similarity NPC477426
0.8382 Intermediate Similarity NPC174956
0.8378 Intermediate Similarity NPC133580
0.8378 Intermediate Similarity NPC32832
0.8375 Intermediate Similarity NPC6391
0.8358 Intermediate Similarity NPC66020
0.8358 Intermediate Similarity NPC240506
0.8354 Intermediate Similarity NPC205845
0.8333 Intermediate Similarity NPC49964
0.8333 Intermediate Similarity NPC101462
0.8333 Intermediate Similarity NPC87489
0.8333 Intermediate Similarity NPC155521
0.8312 Intermediate Similarity NPC295131
0.8312 Intermediate Similarity NPC96362
0.831 Intermediate Similarity NPC266578
0.831 Intermediate Similarity NPC471238
0.831 Intermediate Similarity NPC208999
0.8289 Intermediate Similarity NPC167891
0.8289 Intermediate Similarity NPC476314
0.8289 Intermediate Similarity NPC83351
0.8286 Intermediate Similarity NPC267027
0.8267 Intermediate Similarity NPC253190
0.8261 Intermediate Similarity NPC323424
0.8261 Intermediate Similarity NPC96793
0.8243 Intermediate Similarity NPC91858
0.8243 Intermediate Similarity NPC477138
0.8243 Intermediate Similarity NPC471797
0.8243 Intermediate Similarity NPC243342
0.8243 Intermediate Similarity NPC306727
0.8235 Intermediate Similarity NPC68679
0.8235 Intermediate Similarity NPC321867
0.8235 Intermediate Similarity NPC207007
0.8228 Intermediate Similarity NPC57370
0.8219 Intermediate Similarity NPC471271
0.8219 Intermediate Similarity NPC471268
0.8205 Intermediate Similarity NPC264245
0.8194 Intermediate Similarity NPC473893
0.8194 Intermediate Similarity NPC234511
0.8194 Intermediate Similarity NPC471560
0.8182 Intermediate Similarity NPC143182
0.8182 Intermediate Similarity NPC53744
0.8182 Intermediate Similarity NPC291379
0.8182 Intermediate Similarity NPC47982
0.8182 Intermediate Similarity NPC28862
0.8182 Intermediate Similarity NPC30986
0.8182 Intermediate Similarity NPC81306
0.8182 Intermediate Similarity NPC109546
0.8182 Intermediate Similarity NPC84694
0.8182 Intermediate Similarity NPC209430
0.8169 Intermediate Similarity NPC171225
0.8169 Intermediate Similarity NPC82337
0.8169 Intermediate Similarity NPC114651
0.8158 Intermediate Similarity NPC471798
0.8158 Intermediate Similarity NPC477924
0.8148 Intermediate Similarity NPC255143
0.8148 Intermediate Similarity NPC261266
0.8143 Intermediate Similarity NPC258595
0.8133 Intermediate Similarity NPC477923
0.8133 Intermediate Similarity NPC66566
0.8133 Intermediate Similarity NPC291503
0.8125 Intermediate Similarity NPC302360
0.8125 Intermediate Similarity NPC238485
0.8125 Intermediate Similarity NPC185568
0.8125 Intermediate Similarity NPC231310
0.8125 Intermediate Similarity NPC83702
0.8116 Intermediate Similarity NPC81615
0.8108 Intermediate Similarity NPC259049
0.8108 Intermediate Similarity NPC182717
0.8108 Intermediate Similarity NPC471799
0.8101 Intermediate Similarity NPC202389
0.8101 Intermediate Similarity NPC471408
0.8101 Intermediate Similarity NPC296701
0.8101 Intermediate Similarity NPC218616
0.8082 Intermediate Similarity NPC283316
0.8077 Intermediate Similarity NPC164840
0.8077 Intermediate Similarity NPC241290
0.8077 Intermediate Similarity NPC234193
0.8077 Intermediate Similarity NPC209944
0.8072 Intermediate Similarity NPC470361
0.8056 Intermediate Similarity NPC245795
0.8052 Intermediate Similarity NPC98386
0.8052 Intermediate Similarity NPC196753
0.8052 Intermediate Similarity NPC158662
0.8052 Intermediate Similarity NPC99168
0.8052 Intermediate Similarity NPC253807
0.8052 Intermediate Similarity NPC11908
0.8052 Intermediate Similarity NPC275910
0.8052 Intermediate Similarity NPC230295
0.8052 Intermediate Similarity NPC470396
0.8052 Intermediate Similarity NPC474216
0.8052 Intermediate Similarity NPC474989
0.8052 Intermediate Similarity NPC22955
0.8049 Intermediate Similarity NPC149224
0.8025 Intermediate Similarity NPC470360
0.8025 Intermediate Similarity NPC274448
0.8025 Intermediate Similarity NPC266511
0.8 Intermediate Similarity NPC101128
0.8 Intermediate Similarity NPC144650
0.8 Intermediate Similarity NPC474634
0.8 Intermediate Similarity NPC100334
0.8 Intermediate Similarity NPC68656
0.8 Intermediate Similarity NPC475789
0.8 Intermediate Similarity NPC470384
0.8 Intermediate Similarity NPC317458
0.7976 Intermediate Similarity NPC329596
0.7976 Intermediate Similarity NPC204188
0.7976 Intermediate Similarity NPC291484
0.7976 Intermediate Similarity NPC80561
0.7976 Intermediate Similarity NPC11216
0.7976 Intermediate Similarity NPC3345
0.7975 Intermediate Similarity NPC159148
0.7975 Intermediate Similarity NPC209620
0.7975 Intermediate Similarity NPC47761
0.7975 Intermediate Similarity NPC23852
0.7975 Intermediate Similarity NPC471270
0.7973 Intermediate Similarity NPC110799
0.7973 Intermediate Similarity NPC242001
0.7945 Intermediate Similarity NPC9942
0.7927 Intermediate Similarity NPC152808
0.7927 Intermediate Similarity NPC299068
0.7927 Intermediate Similarity NPC473226
0.7927 Intermediate Similarity NPC293287
0.7922 Intermediate Similarity NPC157996
0.7922 Intermediate Similarity NPC318495
0.7922 Intermediate Similarity NPC155986
0.7922 Intermediate Similarity NPC34177
0.7922 Intermediate Similarity NPC90979
0.7922 Intermediate Similarity NPC198968
0.7922 Intermediate Similarity NPC40394
0.7922 Intermediate Similarity NPC214570
0.7922 Intermediate Similarity NPC283619
0.7922 Intermediate Similarity NPC472805
0.7922 Intermediate Similarity NPC101475
0.7917 Intermediate Similarity NPC68703
0.7917 Intermediate Similarity NPC253303
0.7917 Intermediate Similarity NPC185874
0.7917 Intermediate Similarity NPC139207
0.7917 Intermediate Similarity NPC269077
0.7917 Intermediate Similarity NPC69649
0.7901 Intermediate Similarity NPC46320
0.7901 Intermediate Similarity NPC474047
0.7901 Intermediate Similarity NPC470077
0.7895 Intermediate Similarity NPC171148
0.7895 Intermediate Similarity NPC313179
0.7895 Intermediate Similarity NPC69383
0.7887 Intermediate Similarity NPC60837
0.7887 Intermediate Similarity NPC282619
0.7887 Intermediate Similarity NPC172613
0.7887 Intermediate Similarity NPC208198
0.7887 Intermediate Similarity NPC2728
0.7887 Intermediate Similarity NPC11555
0.7887 Intermediate Similarity NPC287339
0.7882 Intermediate Similarity NPC97404
0.7882 Intermediate Similarity NPC41554
0.7875 Intermediate Similarity NPC189972
0.7875 Intermediate Similarity NPC30166
0.7875 Intermediate Similarity NPC50964
0.7875 Intermediate Similarity NPC470049
0.7875 Intermediate Similarity NPC304285
0.7875 Intermediate Similarity NPC2524
0.7867 Intermediate Similarity NPC130665
0.7857 Intermediate Similarity NPC128066
0.7857 Intermediate Similarity NPC83200
0.7857 Intermediate Similarity NPC314727
0.7848 Intermediate Similarity NPC113024
0.7848 Intermediate Similarity NPC472301
0.7848 Intermediate Similarity NPC148685
0.7848 Intermediate Similarity NPC104120
0.7848 Intermediate Similarity NPC206062
0.7848 Intermediate Similarity NPC95124
0.7848 Intermediate Similarity NPC157895

  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 NPC220939 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
0.8235 Intermediate Similarity NPD368 Approved
0.7949 Intermediate Similarity NPD7645 Phase 2
0.7895 Intermediate Similarity NPD8264 Approved
0.7792 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD6942 Approved
0.7662 Intermediate Similarity NPD7339 Approved
0.7625 Intermediate Similarity NPD7525 Registered
0.7619 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7612 Intermediate Similarity NPD342 Phase 1
0.7407 Intermediate Similarity NPD6930 Phase 2
0.7407 Intermediate Similarity NPD6931 Approved
0.7308 Intermediate Similarity NPD6924 Approved
0.7308 Intermediate Similarity NPD6926 Approved
0.7284 Intermediate Similarity NPD6929 Approved
0.7229 Intermediate Similarity NPD3667 Approved
0.7195 Intermediate Similarity NPD4748 Discontinued
0.7195 Intermediate Similarity NPD7514 Phase 3
0.7195 Intermediate Similarity NPD7332 Phase 2
0.716 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6695 Phase 3
0.7125 Intermediate Similarity NPD6933 Approved
0.7093 Intermediate Similarity NPD3618 Phase 1
0.7059 Intermediate Similarity NPD4786 Approved
0.7059 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6925 Approved
0.7037 Intermediate Similarity NPD5776 Phase 2
0.6988 Remote Similarity NPD7509 Discontinued
0.6977 Remote Similarity NPD6893 Approved
0.6951 Remote Similarity NPD7145 Approved
0.6905 Remote Similarity NPD6902 Approved
0.6905 Remote Similarity NPD6898 Phase 1
0.6875 Remote Similarity NPD4785 Approved
0.6875 Remote Similarity NPD4784 Approved
0.6854 Remote Similarity NPD5328 Approved
0.6835 Remote Similarity NPD7151 Approved
0.6835 Remote Similarity NPD7152 Approved
0.6835 Remote Similarity NPD4243 Approved
0.6835 Remote Similarity NPD7150 Approved
0.6829 Remote Similarity NPD6932 Approved
0.6818 Remote Similarity NPD7524 Approved
0.6818 Remote Similarity NPD7750 Discontinued
0.6813 Remote Similarity NPD4202 Approved
0.6809 Remote Similarity NPD4225 Approved
0.6795 Remote Similarity NPD6923 Approved
0.6795 Remote Similarity NPD6922 Approved
0.6782 Remote Similarity NPD1696 Phase 3
0.6771 Remote Similarity NPD5211 Phase 2
0.6709 Remote Similarity NPD7144 Approved
0.6709 Remote Similarity NPD7143 Approved
0.6703 Remote Similarity NPD6079 Approved
0.6703 Remote Similarity NPD7515 Phase 2
0.6702 Remote Similarity NPD4755 Approved
0.6667 Remote Similarity NPD3665 Phase 1
0.6667 Remote Similarity NPD6683 Phase 2
0.6667 Remote Similarity NPD3133 Approved
0.6667 Remote Similarity NPD3666 Approved
0.6633 Remote Similarity NPD5141 Approved
0.663 Remote Similarity NPD5779 Approved
0.663 Remote Similarity NPD5778 Approved
0.6585 Remote Similarity NPD4190 Phase 3
0.6585 Remote Similarity NPD5275 Approved
0.6562 Remote Similarity NPD5286 Approved
0.6562 Remote Similarity NPD7639 Approved
0.6562 Remote Similarity NPD5285 Approved
0.6562 Remote Similarity NPD4700 Approved
0.6562 Remote Similarity NPD7640 Approved
0.6562 Remote Similarity NPD4696 Approved
0.6543 Remote Similarity NPD4732 Discontinued
0.6522 Remote Similarity NPD7087 Discontinued
0.6517 Remote Similarity NPD4623 Approved
0.6517 Remote Similarity NPD4519 Discontinued
0.6495 Remote Similarity NPD4159 Approved
0.6495 Remote Similarity NPD5344 Discontinued
0.6484 Remote Similarity NPD4753 Phase 2
0.6477 Remote Similarity NPD3668 Phase 3
0.6471 Remote Similarity NPD4195 Approved
0.6458 Remote Similarity NPD7638 Approved
0.6429 Remote Similarity NPD5224 Approved
0.6429 Remote Similarity NPD5226 Approved
0.6429 Remote Similarity NPD4633 Approved
0.6429 Remote Similarity NPD5225 Approved
0.6421 Remote Similarity NPD5222 Approved
0.6421 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6421 Remote Similarity NPD5221 Approved
0.6421 Remote Similarity NPD4697 Phase 3
0.6418 Remote Similarity NPD384 Approved
0.6418 Remote Similarity NPD385 Approved
0.6395 Remote Similarity NPD4820 Approved
0.6395 Remote Similarity NPD4819 Approved
0.6395 Remote Similarity NPD4822 Approved
0.6395 Remote Similarity NPD4821 Approved
0.6383 Remote Similarity NPD7748 Approved
0.6364 Remote Similarity NPD5175 Approved
0.6364 Remote Similarity NPD5174 Approved
0.6354 Remote Similarity NPD5173 Approved
0.6333 Remote Similarity NPD5279 Phase 3
0.6327 Remote Similarity NPD5223 Approved
0.6304 Remote Similarity NPD6101 Approved
0.6304 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6301 Remote Similarity NPD4219 Approved
0.6289 Remote Similarity NPD5290 Discontinued
0.6277 Remote Similarity NPD6399 Phase 3
0.6262 Remote Similarity NPD7115 Discovery
0.625 Remote Similarity NPD4221 Approved
0.625 Remote Similarity NPD4223 Phase 3
0.6238 Remote Similarity NPD4768 Approved
0.6238 Remote Similarity NPD6675 Approved
0.6238 Remote Similarity NPD5739 Approved
0.6238 Remote Similarity NPD6402 Approved
0.6238 Remote Similarity NPD7128 Approved
0.6238 Remote Similarity NPD4767 Approved
0.6237 Remote Similarity NPD3168 Discontinued
0.6224 Remote Similarity NPD6648 Approved
0.6222 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6207 Remote Similarity NPD4695 Discontinued
0.62 Remote Similarity NPD4754 Approved
0.6186 Remote Similarity NPD7902 Approved
0.6176 Remote Similarity NPD5697 Approved
0.6176 Remote Similarity NPD5701 Approved
0.6173 Remote Similarity NPD4267 Clinical (unspecified phase)
0.617 Remote Similarity NPD7637 Suspended
0.617 Remote Similarity NPD6411 Approved
0.6163 Remote Similarity NPD4271 Approved
0.6163 Remote Similarity NPD4268 Approved
0.6154 Remote Similarity NPD371 Approved
0.6154 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6146 Remote Similarity NPD4629 Approved
0.6146 Remote Similarity NPD5210 Approved
0.6129 Remote Similarity NPD6051 Approved
0.6117 Remote Similarity NPD6899 Approved
0.6117 Remote Similarity NPD4729 Approved
0.6117 Remote Similarity NPD6881 Approved
0.6117 Remote Similarity NPD4730 Approved
0.6117 Remote Similarity NPD7320 Approved
0.6117 Remote Similarity NPD5128 Approved
0.6111 Remote Similarity NPD4197 Approved
0.6111 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6064 Remote Similarity NPD7136 Phase 2
0.6058 Remote Similarity NPD6014 Approved
0.6058 Remote Similarity NPD6372 Approved
0.6058 Remote Similarity NPD6013 Approved
0.6058 Remote Similarity NPD6373 Approved
0.6058 Remote Similarity NPD6012 Approved
0.6044 Remote Similarity NPD5329 Approved
0.6044 Remote Similarity NPD1694 Approved
0.6023 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6023 Remote Similarity NPD5790 Clinical (unspecified phase)
0.602 Remote Similarity NPD6083 Phase 2
0.602 Remote Similarity NPD6084 Phase 2
0.6 Remote Similarity NPD4634 Approved
0.6 Remote Similarity NPD5332 Approved
0.6 Remote Similarity NPD5362 Discontinued
0.6 Remote Similarity NPD5250 Approved
0.6 Remote Similarity NPD7102 Approved
0.6 Remote Similarity NPD5249 Phase 3
0.6 Remote Similarity NPD5331 Approved
0.6 Remote Similarity NPD5248 Approved
0.6 Remote Similarity NPD7290 Approved
0.6 Remote Similarity NPD5247 Approved
0.6 Remote Similarity NPD7154 Phase 3
0.6 Remote Similarity NPD5251 Approved
0.6 Remote Similarity NPD6883 Approved
0.5979 Remote Similarity NPD5695 Phase 3
0.5978 Remote Similarity NPD4694 Approved
0.5978 Remote Similarity NPD4688 Approved
0.5978 Remote Similarity NPD4138 Approved
0.5978 Remote Similarity NPD4693 Phase 3
0.5978 Remote Similarity NPD5205 Approved
0.5978 Remote Similarity NPD4690 Approved
0.5978 Remote Similarity NPD5280 Approved
0.5978 Remote Similarity NPD5690 Phase 2
0.5978 Remote Similarity NPD4689 Approved
0.5974 Remote Similarity NPD1145 Discontinued
0.5962 Remote Similarity NPD6011 Approved
0.5955 Remote Similarity NPD4790 Discontinued
0.5943 Remote Similarity NPD5217 Approved
0.5943 Remote Similarity NPD6847 Approved
0.5943 Remote Similarity NPD8130 Phase 1
0.5943 Remote Similarity NPD6649 Approved
0.5943 Remote Similarity NPD6869 Approved
0.5943 Remote Similarity NPD5215 Approved
0.5943 Remote Similarity NPD6617 Approved
0.5943 Remote Similarity NPD6650 Approved
0.5943 Remote Similarity NPD5216 Approved
0.5941 Remote Similarity NPD7632 Discontinued
0.593 Remote Similarity NPD1346 Approved
0.5914 Remote Similarity NPD3573 Approved
0.5905 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5889 Remote Similarity NPD4269 Approved
0.5889 Remote Similarity NPD4270 Approved
0.5888 Remote Similarity NPD6882 Approved
0.5888 Remote Similarity NPD8297 Approved
0.5882 Remote Similarity NPD5700 Clinical (unspecified phase)
0.5876 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5876 Remote Similarity NPD7900 Approved
0.5851 Remote Similarity NPD4722 Approved
0.5851 Remote Similarity NPD4723 Approved
0.5849 Remote Similarity NPD5169 Approved
0.5849 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5849 Remote Similarity NPD5135 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