Structure

Physi-Chem Properties

Molecular Weight:  264.14
Volume:  269.578
LogP:  2.301
LogD:  2.31
LogS:  -3.54
# Rotatable Bonds:  0
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.516
Synthetic Accessibility Score:  4.804
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.741
MDCK Permeability:  1.1583846571738832e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.061
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.022
30% Bioavailability (F30%):  0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.928
Plasma Protein Binding (PPB):  58.897132873535156%
Volume Distribution (VD):  1.302
Pgp-substrate:  39.13812255859375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.473
CYP1A2-substrate:  0.777
CYP2C19-inhibitor:  0.295
CYP2C19-substrate:  0.81
CYP2C9-inhibitor:  0.063
CYP2C9-substrate:  0.054
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.102
CYP3A4-inhibitor:  0.205
CYP3A4-substrate:  0.467

ADMET: Excretion

Clearance (CL):  5.649
Half-life (T1/2):  0.218

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.429
Drug-inuced Liver Injury (DILI):  0.289
AMES Toxicity:  0.587
Rat Oral Acute Toxicity:  0.856
Maximum Recommended Daily Dose:  0.613
Skin Sensitization:  0.485
Carcinogencity:  0.908
Eye Corrosion:  0.075
Eye Irritation:  0.586
Respiratory Toxicity:  0.93

Download Data

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

  Natural Product: NPC287015

Natural Product ID:  NPC287015
Common Name*:   (3Ar,5As,8S,8As)-3A,5A-Dihydroxy-1,5,8-Trimethyl-7,8,8A,9-Tetrahydro-6H-Azuleno[6,5-B]Furan-2-One
IUPAC Name:   (3aR,5aS,8S,8aS)-3a,5a-dihydroxy-1,5,8-trimethyl-7,8,8a,9-tetrahydro-6H-azuleno[6,5-b]furan-2-one
Synonyms:  
Standard InCHIKey:  SEOLELWZKNPODR-YFZRIKAGSA-N
Standard InCHI:  InChI=1S/C15H20O4/c1-8-4-5-14(17)9(2)7-15(18)12(6-11(8)14)10(3)13(16)19-15/h7-8,11,17-18H,4-6H2,1-3H3/t8-,11-,14+,15+/m0/s1
SMILES:  O=C1O[C@]2(C(=C1C)C[C@@H]1[C@@](C(=C2)C)(O)CC[C@@H]1C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1095577
PubChem CID:   46211180
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001770] Guaianolides and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO2035 Daphne aurantiaca Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[20192236]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. flower n.a. PMID[21916433]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota flower buds n.a. n.a. PMID[23558238]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[27228307]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota Roots n.a. n.a. PMID[31150241]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[31860304]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[32223193]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2035 Daphne aurantiaca Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 310.0 nM PMID[459983]
NPT519 Cell Line SH-SY5Y Homo sapiens Activity = 87.7 % PMID[459984]
NPT519 Cell Line SH-SY5Y Homo sapiens Activity = 75.64 % PMID[459984]
NPT519 Cell Line SH-SY5Y Homo sapiens Activity = 4.25 % PMID[459984]
NPT519 Cell Line SH-SY5Y Homo sapiens Activity = 2.7 % PMID[459984]
NPT519 Cell Line SH-SY5Y Homo sapiens Activity = 5.37 % PMID[459984]

☑ 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 NPC287015 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 NPC146850
0.9146 High Similarity NPC290052
0.9048 High Similarity NPC191283
0.8539 High Similarity NPC272293
0.8539 High Similarity NPC40821
0.8539 High Similarity NPC32862
0.8471 Intermediate Similarity NPC53011
0.8471 Intermediate Similarity NPC16887
0.8471 Intermediate Similarity NPC154893
0.8471 Intermediate Similarity NPC37005
0.8372 Intermediate Similarity NPC471185
0.8118 Intermediate Similarity NPC78677
0.8118 Intermediate Similarity NPC59994
0.8111 Intermediate Similarity NPC301969
0.8111 Intermediate Similarity NPC471184
0.8111 Intermediate Similarity NPC37607
0.8065 Intermediate Similarity NPC98165
0.7978 Intermediate Similarity NPC45957
0.7978 Intermediate Similarity NPC471657
0.7957 Intermediate Similarity NPC67584
0.7957 Intermediate Similarity NPC52044
0.7957 Intermediate Similarity NPC220221
0.7955 Intermediate Similarity NPC245434
0.7895 Intermediate Similarity NPC221615
0.7872 Intermediate Similarity NPC213078
0.7841 Intermediate Similarity NPC474693
0.7789 Intermediate Similarity NPC161493
0.7789 Intermediate Similarity NPC477949
0.7766 Intermediate Similarity NPC469873
0.7766 Intermediate Similarity NPC37408
0.7766 Intermediate Similarity NPC170120
0.7753 Intermediate Similarity NPC473659
0.7753 Intermediate Similarity NPC475860
0.7753 Intermediate Similarity NPC474694
0.7738 Intermediate Similarity NPC152017
0.7738 Intermediate Similarity NPC476317
0.7732 Intermediate Similarity NPC150923
0.7692 Intermediate Similarity NPC242448
0.7667 Intermediate Similarity NPC67493
0.766 Intermediate Similarity NPC470013
0.766 Intermediate Similarity NPC127019
0.766 Intermediate Similarity NPC262133
0.766 Intermediate Similarity NPC323008
0.766 Intermediate Similarity NPC470010
0.7619 Intermediate Similarity NPC85831
0.7619 Intermediate Similarity NPC215215
0.7619 Intermediate Similarity NPC265921
0.7579 Intermediate Similarity NPC213698
0.7556 Intermediate Similarity NPC253604
0.7551 Intermediate Similarity NPC62670
0.7551 Intermediate Similarity NPC116139
0.7551 Intermediate Similarity NPC475099
0.7526 Intermediate Similarity NPC244411
0.75 Intermediate Similarity NPC91248
0.75 Intermediate Similarity NPC472819
0.7475 Intermediate Similarity NPC66110
0.7474 Intermediate Similarity NPC96541
0.7474 Intermediate Similarity NPC90453
0.7474 Intermediate Similarity NPC198853
0.7474 Intermediate Similarity NPC477131
0.7474 Intermediate Similarity NPC472467
0.7471 Intermediate Similarity NPC226226
0.7471 Intermediate Similarity NPC55304
0.7449 Intermediate Similarity NPC472826
0.7449 Intermediate Similarity NPC469864
0.7449 Intermediate Similarity NPC280963
0.7449 Intermediate Similarity NPC469872
0.7447 Intermediate Similarity NPC475925
0.7444 Intermediate Similarity NPC116613
0.7442 Intermediate Similarity NPC53581
0.7442 Intermediate Similarity NPC103987
0.7442 Intermediate Similarity NPC476439
0.7426 Intermediate Similarity NPC472818
0.7419 Intermediate Similarity NPC205548
0.7419 Intermediate Similarity NPC212664
0.7416 Intermediate Similarity NPC133844
0.74 Intermediate Similarity NPC124881
0.7396 Intermediate Similarity NPC476487
0.7396 Intermediate Similarity NPC329435
0.7396 Intermediate Similarity NPC476488
0.7391 Intermediate Similarity NPC160138
0.7386 Intermediate Similarity NPC10636
0.7374 Intermediate Similarity NPC295110
0.7374 Intermediate Similarity NPC25177
0.7374 Intermediate Similarity NPC268829
0.7374 Intermediate Similarity NPC247701
0.7374 Intermediate Similarity NPC222875
0.7363 Intermediate Similarity NPC300082
0.7363 Intermediate Similarity NPC204105
0.7363 Intermediate Similarity NPC476628
0.7363 Intermediate Similarity NPC284534
0.7363 Intermediate Similarity NPC235792
0.7356 Intermediate Similarity NPC222210
0.7356 Intermediate Similarity NPC470944
0.7356 Intermediate Similarity NPC63445
0.7353 Intermediate Similarity NPC472820
0.7333 Intermediate Similarity NPC471340
0.7327 Intermediate Similarity NPC200861
0.732 Intermediate Similarity NPC9812
0.7312 Intermediate Similarity NPC79549
0.7292 Intermediate Similarity NPC474338
0.7283 Intermediate Similarity NPC477668
0.7273 Intermediate Similarity NPC290802
0.7263 Intermediate Similarity NPC472468
0.7263 Intermediate Similarity NPC133698
0.7263 Intermediate Similarity NPC131209
0.7263 Intermediate Similarity NPC290651
0.7253 Intermediate Similarity NPC472957
0.7253 Intermediate Similarity NPC156485
0.7253 Intermediate Similarity NPC472958
0.7234 Intermediate Similarity NPC295312
0.7234 Intermediate Similarity NPC215556
0.7229 Intermediate Similarity NPC265574
0.7229 Intermediate Similarity NPC144647
0.7228 Intermediate Similarity NPC187302
0.7228 Intermediate Similarity NPC196471
0.7228 Intermediate Similarity NPC189588
0.7228 Intermediate Similarity NPC10232
0.7228 Intermediate Similarity NPC472821
0.7228 Intermediate Similarity NPC97487
0.7228 Intermediate Similarity NPC160583
0.7216 Intermediate Similarity NPC304886
0.7212 Intermediate Similarity NPC475030
0.7212 Intermediate Similarity NPC475274
0.72 Intermediate Similarity NPC477950
0.7191 Intermediate Similarity NPC186072
0.7188 Intermediate Similarity NPC135776
0.7188 Intermediate Similarity NPC258216
0.7174 Intermediate Similarity NPC471494
0.7172 Intermediate Similarity NPC64742
0.716 Intermediate Similarity NPC205618
0.716 Intermediate Similarity NPC469326
0.716 Intermediate Similarity NPC261782
0.7159 Intermediate Similarity NPC476627
0.7158 Intermediate Similarity NPC472466
0.7158 Intermediate Similarity NPC216284
0.7158 Intermediate Similarity NPC77337
0.7158 Intermediate Similarity NPC473448
0.7143 Intermediate Similarity NPC30502
0.7143 Intermediate Similarity NPC18019
0.7143 Intermediate Similarity NPC181298
0.7143 Intermediate Similarity NPC319861
0.7143 Intermediate Similarity NPC165632
0.7143 Intermediate Similarity NPC472473
0.7143 Intermediate Similarity NPC24956
0.7143 Intermediate Similarity NPC477667
0.7129 Intermediate Similarity NPC86077
0.7128 Intermediate Similarity NPC224652
0.7113 Intermediate Similarity NPC281775
0.7111 Intermediate Similarity NPC325031
0.7111 Intermediate Similarity NPC471661
0.7111 Intermediate Similarity NPC15978
0.7111 Intermediate Similarity NPC472471
0.71 Intermediate Similarity NPC70865
0.71 Intermediate Similarity NPC16601
0.71 Intermediate Similarity NPC130792
0.7097 Intermediate Similarity NPC311163
0.7097 Intermediate Similarity NPC471219
0.7097 Intermediate Similarity NPC474045
0.7097 Intermediate Similarity NPC137253
0.7097 Intermediate Similarity NPC64153
0.7097 Intermediate Similarity NPC261253
0.7087 Intermediate Similarity NPC223450
0.7087 Intermediate Similarity NPC186668
0.7087 Intermediate Similarity NPC119855
0.7087 Intermediate Similarity NPC243998
0.7087 Intermediate Similarity NPC220217
0.7083 Intermediate Similarity NPC221282
0.7083 Intermediate Similarity NPC2882
0.7083 Intermediate Similarity NPC155215
0.7083 Intermediate Similarity NPC78594
0.7079 Intermediate Similarity NPC471890
0.7079 Intermediate Similarity NPC472013
0.7079 Intermediate Similarity NPC476624
0.7079 Intermediate Similarity NPC66677
0.7079 Intermediate Similarity NPC84185
0.7079 Intermediate Similarity NPC204270
0.7075 Intermediate Similarity NPC262083
0.7075 Intermediate Similarity NPC471484
0.7071 Intermediate Similarity NPC213947
0.7071 Intermediate Similarity NPC170143
0.7071 Intermediate Similarity NPC231751
0.7071 Intermediate Similarity NPC476253
0.7071 Intermediate Similarity NPC471462
0.7071 Intermediate Similarity NPC108475
0.7071 Intermediate Similarity NPC47834
0.7065 Intermediate Similarity NPC471301
0.7065 Intermediate Similarity NPC471302
0.7059 Intermediate Similarity NPC183570
0.7059 Intermediate Similarity NPC280566
0.7053 Intermediate Similarity NPC32922
0.7053 Intermediate Similarity NPC268298
0.7053 Intermediate Similarity NPC232747
0.7053 Intermediate Similarity NPC225283
0.7045 Intermediate Similarity NPC84360
0.703 Intermediate Similarity NPC206079
0.703 Intermediate Similarity NPC298233
0.7021 Intermediate Similarity NPC471796
0.7021 Intermediate Similarity NPC237540
0.7011 Intermediate Similarity NPC89374

  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 NPC287015 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
0.7174 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5362 Discontinued
0.6931 Remote Similarity NPD7640 Approved
0.6931 Remote Similarity NPD7639 Approved
0.6915 Remote Similarity NPD4249 Approved
0.6875 Remote Similarity NPD1695 Approved
0.6857 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6852 Remote Similarity NPD6053 Discontinued
0.6842 Remote Similarity NPD4250 Approved
0.6842 Remote Similarity NPD4251 Approved
0.6832 Remote Similarity NPD7638 Approved
0.6822 Remote Similarity NPD6371 Approved
0.6774 Remote Similarity NPD5331 Approved
0.6774 Remote Similarity NPD5332 Approved
0.6739 Remote Similarity NPD4790 Discontinued
0.6696 Remote Similarity NPD7328 Approved
0.6696 Remote Similarity NPD7327 Approved
0.6637 Remote Similarity NPD7516 Approved
0.6633 Remote Similarity NPD5785 Approved
0.663 Remote Similarity NPD5790 Clinical (unspecified phase)
0.663 Remote Similarity NPD4820 Approved
0.663 Remote Similarity NPD4819 Approved
0.663 Remote Similarity NPD4822 Approved
0.663 Remote Similarity NPD4821 Approved
0.6579 Remote Similarity NPD8294 Approved
0.6579 Remote Similarity NPD8377 Approved
0.6566 Remote Similarity NPD5693 Phase 1
0.6522 Remote Similarity NPD8335 Approved
0.6522 Remote Similarity NPD8378 Approved
0.6522 Remote Similarity NPD8033 Approved
0.6522 Remote Similarity NPD8380 Approved
0.6522 Remote Similarity NPD8379 Approved
0.6522 Remote Similarity NPD8296 Approved
0.6505 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6465 Remote Similarity NPD7838 Discovery
0.6458 Remote Similarity NPD5363 Approved
0.6441 Remote Similarity NPD7507 Approved
0.6413 Remote Similarity NPD4271 Approved
0.6413 Remote Similarity NPD4268 Approved
0.6373 Remote Similarity NPD5695 Phase 3
0.6364 Remote Similarity NPD6051 Approved
0.6354 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6353 Remote Similarity NPD2685 Clinical (unspecified phase)
0.633 Remote Similarity NPD6686 Approved
0.6321 Remote Similarity NPD7632 Discontinued
0.6316 Remote Similarity NPD4270 Approved
0.6316 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6316 Remote Similarity NPD4269 Approved
0.63 Remote Similarity NPD46 Approved
0.63 Remote Similarity NPD6698 Approved
0.6281 Remote Similarity NPD7319 Approved
0.625 Remote Similarity NPD6083 Phase 2
0.625 Remote Similarity NPD7154 Phase 3
0.625 Remote Similarity NPD6084 Phase 2
0.6239 Remote Similarity NPD7503 Approved
0.6238 Remote Similarity NPD5284 Approved
0.6238 Remote Similarity NPD7637 Suspended
0.6238 Remote Similarity NPD5281 Approved
0.6237 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6226 Remote Similarity NPD5344 Discontinued
0.6224 Remote Similarity NPD5786 Approved
0.6214 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6211 Remote Similarity NPD5369 Approved
0.62 Remote Similarity NPD6080 Approved
0.62 Remote Similarity NPD6673 Approved
0.62 Remote Similarity NPD6904 Approved
0.619 Remote Similarity NPD5696 Approved
0.617 Remote Similarity NPD4195 Approved
0.6146 Remote Similarity NPD4223 Phase 3
0.6146 Remote Similarity NPD6435 Approved
0.6146 Remote Similarity NPD4221 Approved
0.6139 Remote Similarity NPD5692 Phase 3
0.6139 Remote Similarity NPD5207 Approved
0.6132 Remote Similarity NPD6648 Approved
0.6105 Remote Similarity NPD4252 Approved
0.61 Remote Similarity NPD5208 Approved
0.6082 Remote Similarity NPD6695 Phase 3
0.6078 Remote Similarity NPD6050 Approved
0.6078 Remote Similarity NPD5694 Approved
0.6058 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6038 Remote Similarity NPD4225 Approved
0.602 Remote Similarity NPD4197 Approved
0.602 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6 Remote Similarity NPD6008 Approved
0.5979 Remote Similarity NPD5209 Approved
0.5962 Remote Similarity NPD6001 Approved
0.596 Remote Similarity NPD5329 Approved
0.596 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5946 Remote Similarity NPD6412 Phase 2
0.5941 Remote Similarity NPD6903 Approved
0.5938 Remote Similarity NPD5368 Approved
0.59 Remote Similarity NPD6684 Approved
0.59 Remote Similarity NPD6409 Approved
0.59 Remote Similarity NPD6098 Approved
0.59 Remote Similarity NPD5690 Phase 2
0.59 Remote Similarity NPD5330 Approved
0.59 Remote Similarity NPD7334 Approved
0.59 Remote Similarity NPD4690 Approved
0.59 Remote Similarity NPD4693 Phase 3
0.59 Remote Similarity NPD4138 Approved
0.59 Remote Similarity NPD5205 Approved
0.59 Remote Similarity NPD7521 Approved
0.59 Remote Similarity NPD4689 Approved
0.59 Remote Similarity NPD5280 Approved
0.59 Remote Similarity NPD7146 Approved
0.59 Remote Similarity NPD4688 Approved
0.59 Remote Similarity NPD4694 Approved
0.5897 Remote Similarity NPD6009 Approved
0.5893 Remote Similarity NPD7320 Approved
0.5882 Remote Similarity NPD4753 Phase 2
0.5877 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5865 Remote Similarity NPD5779 Approved
0.5865 Remote Similarity NPD5778 Approved
0.5856 Remote Similarity NPD5739 Approved
0.5856 Remote Similarity NPD6402 Approved
0.5856 Remote Similarity NPD7128 Approved
0.5856 Remote Similarity NPD6675 Approved
0.5849 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5842 Remote Similarity NPD4751 Clinical (unspecified phase)
0.5842 Remote Similarity NPD7750 Discontinued
0.5842 Remote Similarity NPD7524 Approved
0.5826 Remote Similarity NPD6882 Approved
0.582 Remote Similarity NPD7492 Approved
0.581 Remote Similarity NPD5282 Discontinued
0.5804 Remote Similarity NPD5697 Approved
0.5804 Remote Similarity NPD5701 Approved
0.58 Remote Similarity NPD1694 Approved
0.5784 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5784 Remote Similarity NPD6672 Approved
0.5784 Remote Similarity NPD5737 Approved
0.5784 Remote Similarity NPD4518 Approved
0.5776 Remote Similarity NPD4632 Approved
0.5773 Remote Similarity NPD6931 Approved
0.5773 Remote Similarity NPD6930 Phase 2
0.5772 Remote Similarity NPD6616 Approved
0.5769 Remote Similarity NPD7983 Approved
0.5763 Remote Similarity NPD7115 Discovery
0.5761 Remote Similarity NPD4243 Approved
0.5755 Remote Similarity NPD5654 Approved
0.5752 Remote Similarity NPD6881 Approved
0.5752 Remote Similarity NPD6899 Approved
0.5752 Remote Similarity NPD6011 Approved
0.575 Remote Similarity NPD6059 Approved
0.575 Remote Similarity NPD6054 Approved
0.5726 Remote Similarity NPD8293 Discontinued
0.5726 Remote Similarity NPD7078 Approved
0.5714 Remote Similarity NPD4211 Phase 1
0.5714 Remote Similarity NPD6399 Phase 3
0.5702 Remote Similarity NPD6372 Approved
0.5702 Remote Similarity NPD6013 Approved
0.5702 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5702 Remote Similarity NPD6015 Approved
0.5702 Remote Similarity NPD6012 Approved
0.5702 Remote Similarity NPD6016 Approved
0.5702 Remote Similarity NPD6373 Approved
0.5702 Remote Similarity NPD6014 Approved
0.5701 Remote Similarity NPD7839 Suspended
0.57 Remote Similarity NPD3666 Approved
0.57 Remote Similarity NPD3133 Approved
0.57 Remote Similarity NPD3665 Phase 1
0.568 Remote Similarity NPD7736 Approved
0.5676 Remote Similarity NPD6052 Approved
0.5673 Remote Similarity NPD4096 Approved
0.567 Remote Similarity NPD6929 Approved
0.5656 Remote Similarity NPD6370 Approved
0.5656 Remote Similarity NPD5988 Approved
0.5652 Remote Similarity NPD6883 Approved
0.5652 Remote Similarity NPD7290 Approved
0.5652 Remote Similarity NPD7102 Approved
0.5652 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5648 Remote Similarity NPD5959 Approved
0.5638 Remote Similarity NPD4784 Approved
0.5638 Remote Similarity NPD4785 Approved
0.562 Remote Similarity NPD6319 Approved
0.5619 Remote Similarity NPD7087 Discontinued
0.5612 Remote Similarity NPD7514 Phase 3
0.5607 Remote Similarity NPD5210 Approved
0.5607 Remote Similarity NPD4629 Approved
0.5603 Remote Similarity NPD6649 Approved
0.5603 Remote Similarity NPD6650 Approved
0.5603 Remote Similarity NPD8130 Phase 1
0.5603 Remote Similarity NPD6617 Approved
0.5603 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5603 Remote Similarity NPD6869 Approved
0.5603 Remote Similarity NPD6847 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