Structure

Physi-Chem Properties

Molecular Weight:  504.16
Volume:  470.491
LogP:  1.029
LogD:  0.682
LogS:  -3.222
# Rotatable Bonds:  4
TPSA:  161.96
# H-Bond Aceptor:  11
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.325
Synthetic Accessibility Score:  6.767
Fsp3:  0.64
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:  -5.67
MDCK Permeability:  6.292723264778033e-05
Pgp-inhibitor:  0.016
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.051
20% Bioavailability (F20%):  0.132
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.109
Plasma Protein Binding (PPB):  63.544185638427734%
Volume Distribution (VD):  0.511
Pgp-substrate:  38.639347076416016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.504
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.069
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.025
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.111
CYP3A4-inhibitor:  0.479
CYP3A4-substrate:  0.205

ADMET: Excretion

Clearance (CL):  2.799
Half-life (T1/2):  0.8

ADMET: Toxicity

hERG Blockers:  0.053
Human Hepatotoxicity (H-HT):  0.853
Drug-inuced Liver Injury (DILI):  0.953
AMES Toxicity:  0.065
Rat Oral Acute Toxicity:  0.669
Maximum Recommended Daily Dose:  0.681
Skin Sensitization:  0.16
Carcinogencity:  0.067
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.906

Download Data

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

  Natural Product: NPC476008

Natural Product ID:  NPC476008
Common Name*:   Sergeolide
IUPAC Name:   n.a.
Synonyms:   Sergeolide; Sergiolide
Standard InCHIKey:  ZZKFDOQILIXHHH-UAXMYPJESA-N
Standard InCHI:  InChI=1S/C25H28O11/c1-9-11-5-15(27)35-13(11)7-23(3)12(9)6-14-24-8-33-25(22(31)32-4,20(29)16(28)18(23)24)19(24)17(21(30)36-14)34-10(2)26/h5,7,9,12,14,16-20,28-29H,6,8H2,1-4H3/t9-,12+,14-,16-,17-,18-,19-,20+,23+,24-,25-/m1/s1
SMILES:  C[C@@H]1C2=CC(=O)OC2=C[C@@]2(C)[C@H]1C[C@@H]1[C@]34CO[C@]([C@@H]4[C@H](C(=O)O1)OC(=O)C)([C@H]([C@@H]([C@H]23)O)O)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL521373
PubChem CID:   44575805
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0002119] Quassinoids

*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
NPO33214 cedronia granatensis Species n.a. n.a. n.a. n.a. n.a. PMID[1517739]
NPO4057 Picrolemma pseudocoffea Species n.a. n.a. n.a. n.a. n.a. PMID[6533270]
NPO4057 Picrolemma pseudocoffea Species n.a. n.a. 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
NPT381 Cell Line OVCAR-8 Homo sapiens LC50 = 776.25 nM PMID[495014]
NPT146 Cell Line SK-OV-3 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT382 Cell Line OVCAR-5 Homo sapiens LC50 = 3311.31 nM PMID[495014]
NPT404 Cell Line CCRF-CEM Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT116 Cell Line HL-60 Homo sapiens LC50 = 57.54 nM PMID[495014]
NPT111 Cell Line K562 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT112 Cell Line MOLT-4 Homo sapiens LC50 = 3890.45 nM PMID[495014]
NPT389 Cell Line RPMI-8226 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT385 Cell Line SR Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT81 Cell Line A549 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT394 Cell Line EKVX Homo sapiens LC50 = 891.25 nM PMID[495014]
NPT732 Cell Line HOP-18 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT379 Cell Line HOP-62 Homo sapiens LC50 = 1905.46 nM PMID[495014]
NPT372 Cell Line HOP-92 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT405 Cell Line NCI-H226 Homo sapiens LC50 = 66.07 nM PMID[495014]
NPT370 Cell Line NCI-H23 Homo sapiens LC50 = 70.79 nM PMID[495014]
NPT397 Cell Line NCI-H460 Homo sapiens LC50 = 457.09 nM PMID[495014]
NPT455 Cell Line NCI-H522 Homo sapiens LC50 = 15.85 nM PMID[495014]
NPT576 Cell Line DMS-114 Homo sapiens LC50 = 36.31 nM PMID[495014]
NPT572 Cell Line DMS-273 Homo sapiens LC50 = 109.65 nM PMID[495014]
NPT407 Cell Line COLO 205 Homo sapiens LC50 = 21.88 nM PMID[495014]
NPT391 Cell Line HCC 2998 Homo sapiens LC50 = 28.84 nM PMID[495014]
NPT393 Cell Line HCT-116 Homo sapiens LC50 = 128.82 nM PMID[495014]
NPT148 Cell Line HCT-15 Homo sapiens LC50 = 1905.46 nM PMID[495014]
NPT139 Cell Line HT-29 Homo sapiens LC50 = 3801.89 nM PMID[495014]
NPT386 Cell Line KM12 Homo sapiens LC50 = 436.52 nM PMID[495014]
NPT575 Cell Line KM-20L2 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT323 Cell Line SW-620 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT395 Cell Line SF-268 Homo sapiens LC50 = 2089.3 nM PMID[495014]
NPT399 Cell Line SF-295 Homo sapiens LC50 = 380.19 nM PMID[495014]
NPT374 Cell Line SF-539 Homo sapiens LC50 = 25.7 nM PMID[495014]
NPT383 Cell Line SNB-19 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT392 Cell Line SNB-75 Homo sapiens LC50 = 38.9 nM PMID[495014]
NPT578 Cell Line SNB-78 Homo sapiens LC50 = 2511.89 nM PMID[495014]
NPT380 Cell Line U-251 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT574 Cell Line XF498 Homo sapiens LC50 = 58.88 nM PMID[495014]
NPT390 Cell Line LOX IMVI Homo sapiens LC50 = 288.4 nM PMID[495014]
NPT375 Cell Line Malme-3M Homo sapiens LC50 = 12.02 nM PMID[495014]
NPT387 Cell Line M14 Homo sapiens LC50 = 20.89 nM PMID[495014]
NPT170 Cell Line SK-MEL-28 Homo sapiens LC50 = 120.23 nM PMID[495014]
NPT147 Cell Line SK-MEL-2 Homo sapiens LC50 = 26.92 nM PMID[495014]
NPT373 Cell Line SK-MEL-5 Homo sapiens LC50 = 6.607 nM PMID[495014]
NPT403 Cell Line UACC-257 Homo sapiens LC50 = 58.88 nM PMID[495014]
NPT398 Cell Line UACC-62 Homo sapiens LC50 = 32.36 nM PMID[495014]
NPT458 Cell Line IGROV-1 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT377 Cell Line OVCAR-3 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT456 Cell Line OVCAR-4 Homo sapiens LC50 = 44.67 nM PMID[495014]
NPT376 Cell Line A498 Homo sapiens LC50 = 57.54 nM PMID[495014]
NPT369 Cell Line ACHN Homo sapiens LC50 = 3388.44 nM PMID[495014]
NPT308 Cell Line CAKI-1 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT406 Cell Line RXF 393 Homo sapiens LC50 = 51.29 nM PMID[495014]
NPT368 Cell Line SN12C Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT384 Cell Line TK-10 Homo sapiens LC50 = 3981.07 nM PMID[495014]
NPT371 Cell Line UO-31 Homo sapiens LC50 = 2884.03 nM PMID[495014]
NPT579 Cell Line DLD-1 Homo sapiens LC50 = 3235.94 nM PMID[495014]
NPT573 Cell Line M19-MEL Homo sapiens LC50 = 19.95 nM PMID[495014]
NPT168 Cell Line P388 Mus musculus T/C = 169.0 % PMID[495015]
NPT165 Cell Line HeLa Homo sapiens IC50 < 1000.0 nM PMID[495016]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. LC50 = 407.38 nM PMID[495014]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. LC50 = 3981.07 nM PMID[495014]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. LC50 = 67.61 nM PMID[495014]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. LC50 = 3715.35 nM PMID[495014]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 3.8 nM PMID[495016]
NPT2 Others Unspecified INH = 0.07 uM PMID[495016]

☑ 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 NPC476008 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
0.9914 High Similarity NPC477745
0.9487 High Similarity NPC312833
0.9407 High Similarity NPC265557
0.9407 High Similarity NPC105926
0.9407 High Similarity NPC91693
0.9407 High Similarity NPC18945
0.9328 High Similarity NPC476729
0.9328 High Similarity NPC24651
0.9244 High Similarity NPC67251
0.9076 High Similarity NPC470779
0.8983 High Similarity NPC470776
0.8983 High Similarity NPC17772
0.8908 High Similarity NPC470777
0.8898 High Similarity NPC473590
0.8889 High Similarity NPC45218
0.8889 High Similarity NPC268238
0.8889 High Similarity NPC323821
0.8889 High Similarity NPC143268
0.8819 High Similarity NPC262813
0.8814 High Similarity NPC173686
0.8814 High Similarity NPC89929
0.8814 High Similarity NPC16081
0.8803 High Similarity NPC94509
0.875 High Similarity NPC190065
0.875 High Similarity NPC141215
0.875 High Similarity NPC251998
0.875 High Similarity NPC471089
0.8739 High Similarity NPC474654
0.8739 High Similarity NPC176513
0.8739 High Similarity NPC97908
0.8739 High Similarity NPC470854
0.8739 High Similarity NPC287343
0.8739 High Similarity NPC146432
0.8739 High Similarity NPC470775
0.8739 High Similarity NPC122033
0.8739 High Similarity NPC470778
0.8729 High Similarity NPC299849
0.8699 High Similarity NPC470922
0.8682 High Similarity NPC596
0.8682 High Similarity NPC140045
0.8682 High Similarity NPC295885
0.8667 High Similarity NPC251310
0.8661 High Similarity NPC168879
0.8655 High Similarity NPC40632
0.8655 High Similarity NPC328374
0.8655 High Similarity NPC251236
0.8655 High Similarity NPC474734
0.8655 High Similarity NPC96312
0.8655 High Similarity NPC213084
0.8655 High Similarity NPC190185
0.8644 High Similarity NPC49451
0.8644 High Similarity NPC478212
0.8629 High Similarity NPC181999
0.8605 High Similarity NPC243014
0.8583 High Similarity NPC53396
0.8583 High Similarity NPC98249
0.8583 High Similarity NPC478204
0.8571 High Similarity NPC473798
0.8525 High Similarity NPC478051
0.8525 High Similarity NPC112038
0.8525 High Similarity NPC472004
0.8525 High Similarity NPC107338
0.8525 High Similarity NPC109607
0.8512 High Similarity NPC188667
0.8512 High Similarity NPC297179
0.8512 High Similarity NPC108581
0.8512 High Similarity NPC478205
0.8512 High Similarity NPC478206
0.8512 High Similarity NPC204552
0.8512 High Similarity NPC284707
0.85 High Similarity NPC207217
0.8487 Intermediate Similarity NPC208998
0.8487 Intermediate Similarity NPC7921
0.8455 Intermediate Similarity NPC102822
0.8455 Intermediate Similarity NPC477046
0.8443 Intermediate Similarity NPC476529
0.8443 Intermediate Similarity NPC475775
0.8438 Intermediate Similarity NPC102316
0.8425 Intermediate Similarity NPC476851
0.8413 Intermediate Similarity NPC470780
0.839 Intermediate Similarity NPC478209
0.8359 Intermediate Similarity NPC476852
0.8347 Intermediate Similarity NPC134869
0.8347 Intermediate Similarity NPC478216
0.8347 Intermediate Similarity NPC474046
0.8347 Intermediate Similarity NPC470628
0.8347 Intermediate Similarity NPC152199
0.8347 Intermediate Similarity NPC259306
0.8347 Intermediate Similarity NPC235539
0.8346 Intermediate Similarity NPC475636
0.8346 Intermediate Similarity NPC295220
0.8333 Intermediate Similarity NPC198539
0.8333 Intermediate Similarity NPC87662
0.8319 Intermediate Similarity NPC146945
0.8319 Intermediate Similarity NPC171888
0.8319 Intermediate Similarity NPC97939
0.8319 Intermediate Similarity NPC247031
0.8319 Intermediate Similarity NPC100329
0.8319 Intermediate Similarity NPC132790
0.8308 Intermediate Similarity NPC242486
0.8308 Intermediate Similarity NPC15215
0.8306 Intermediate Similarity NPC472000
0.8306 Intermediate Similarity NPC471999
0.8305 Intermediate Similarity NPC478210
0.8295 Intermediate Similarity NPC478154
0.8293 Intermediate Similarity NPC469488
0.8291 Intermediate Similarity NPC302788
0.8281 Intermediate Similarity NPC54614
0.8281 Intermediate Similarity NPC231529
0.8281 Intermediate Similarity NPC309096
0.8279 Intermediate Similarity NPC58662
0.8279 Intermediate Similarity NPC469684
0.8279 Intermediate Similarity NPC473968
0.8264 Intermediate Similarity NPC469877
0.8264 Intermediate Similarity NPC178289
0.8264 Intermediate Similarity NPC18547
0.8264 Intermediate Similarity NPC474906
0.8264 Intermediate Similarity NPC470919
0.8264 Intermediate Similarity NPC117712
0.825 Intermediate Similarity NPC11252
0.825 Intermediate Similarity NPC269530
0.825 Intermediate Similarity NPC289312
0.825 Intermediate Similarity NPC474516
0.825 Intermediate Similarity NPC302146
0.8235 Intermediate Similarity NPC478211
0.8235 Intermediate Similarity NPC472666
0.8231 Intermediate Similarity NPC478151
0.822 Intermediate Similarity NPC293850
0.8217 Intermediate Similarity NPC25998
0.8217 Intermediate Similarity NPC478155
0.8217 Intermediate Similarity NPC476074
0.8217 Intermediate Similarity NPC329993
0.8217 Intermediate Similarity NPC475377
0.8217 Intermediate Similarity NPC478065
0.8217 Intermediate Similarity NPC134914
0.8217 Intermediate Similarity NPC301639
0.8217 Intermediate Similarity NPC262796
0.8217 Intermediate Similarity NPC475167
0.8217 Intermediate Similarity NPC264566
0.8217 Intermediate Similarity NPC173435
0.8217 Intermediate Similarity NPC172374
0.8217 Intermediate Similarity NPC45346
0.8217 Intermediate Similarity NPC478064
0.8211 Intermediate Similarity NPC106644
0.8211 Intermediate Similarity NPC240509
0.8211 Intermediate Similarity NPC21326
0.8205 Intermediate Similarity NPC34768
0.8203 Intermediate Similarity NPC476859
0.8203 Intermediate Similarity NPC188291
0.8197 Intermediate Similarity NPC477509
0.8182 Intermediate Similarity NPC469463
0.8182 Intermediate Similarity NPC51978
0.8182 Intermediate Similarity NPC477126
0.8182 Intermediate Similarity NPC471204
0.8182 Intermediate Similarity NPC469496
0.8182 Intermediate Similarity NPC469454
0.8182 Intermediate Similarity NPC475966
0.8175 Intermediate Similarity NPC227397
0.8175 Intermediate Similarity NPC120724
0.8167 Intermediate Similarity NPC179798
0.8167 Intermediate Similarity NPC474846
0.8167 Intermediate Similarity NPC304180
0.8167 Intermediate Similarity NPC469655
0.8167 Intermediate Similarity NPC201992
0.8167 Intermediate Similarity NPC469656
0.8154 Intermediate Similarity NPC254614
0.8154 Intermediate Similarity NPC476193
0.8154 Intermediate Similarity NPC100390
0.8154 Intermediate Similarity NPC478153
0.8154 Intermediate Similarity NPC478152
0.8154 Intermediate Similarity NPC478150
0.8151 Intermediate Similarity NPC27814
0.8145 Intermediate Similarity NPC473636
0.8145 Intermediate Similarity NPC77689
0.8145 Intermediate Similarity NPC476107
0.8145 Intermediate Similarity NPC19028
0.8145 Intermediate Similarity NPC9674
0.814 Intermediate Similarity NPC264192
0.814 Intermediate Similarity NPC476854
0.814 Intermediate Similarity NPC477196
0.8136 Intermediate Similarity NPC144854
0.8136 Intermediate Similarity NPC202524
0.8136 Intermediate Similarity NPC3316
0.813 Intermediate Similarity NPC134430
0.8125 Intermediate Similarity NPC471357
0.8125 Intermediate Similarity NPC117702
0.8125 Intermediate Similarity NPC470882
0.8125 Intermediate Similarity NPC469757
0.8125 Intermediate Similarity NPC146456
0.8099 Intermediate Similarity NPC472002
0.8095 Intermediate Similarity NPC222688
0.8095 Intermediate Similarity NPC269642
0.8092 Intermediate Similarity NPC88668
0.8083 Intermediate Similarity NPC210005
0.8083 Intermediate Similarity NPC5103
0.808 Intermediate Similarity NPC109973
0.8077 Intermediate Similarity NPC476863
0.8077 Intermediate Similarity NPC476862
0.8077 Intermediate Similarity NPC476855
0.8077 Intermediate Similarity NPC477197

  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 NPC476008 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
0.8 Intermediate Similarity NPD7319 Approved
0.7917 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7851 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7795 Intermediate Similarity NPD6319 Approved
0.7787 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7769 Intermediate Similarity NPD7507 Approved
0.7752 Intermediate Similarity NPD8328 Phase 3
0.7557 Intermediate Similarity NPD7492 Approved
0.7541 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD6059 Approved
0.7519 Intermediate Similarity NPD6054 Approved
0.7519 Intermediate Similarity NPD7736 Approved
0.75 Intermediate Similarity NPD6616 Approved
0.748 Intermediate Similarity NPD6686 Approved
0.7462 Intermediate Similarity NPD8517 Approved
0.7462 Intermediate Similarity NPD8513 Phase 3
0.7462 Intermediate Similarity NPD6015 Approved
0.7462 Intermediate Similarity NPD8516 Approved
0.7462 Intermediate Similarity NPD8515 Approved
0.7462 Intermediate Similarity NPD6016 Approved
0.7444 Intermediate Similarity NPD7078 Approved
0.7444 Intermediate Similarity NPD8293 Discontinued
0.7442 Intermediate Similarity NPD7516 Approved
0.7422 Intermediate Similarity NPD7115 Discovery
0.7422 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6372 Approved
0.7419 Intermediate Similarity NPD6373 Approved
0.7405 Intermediate Similarity NPD6370 Approved
0.7405 Intermediate Similarity NPD5988 Approved
0.7395 Intermediate Similarity NPD4225 Approved
0.7381 Intermediate Similarity NPD8297 Approved
0.7364 Intermediate Similarity NPD7328 Approved
0.7364 Intermediate Similarity NPD7327 Approved
0.7339 Intermediate Similarity NPD7320 Approved
0.7328 Intermediate Similarity NPD7503 Approved
0.7328 Intermediate Similarity NPD6921 Approved
0.7323 Intermediate Similarity NPD4632 Approved
0.7317 Intermediate Similarity NPD7128 Approved
0.7317 Intermediate Similarity NPD5739 Approved
0.7317 Intermediate Similarity NPD6675 Approved
0.7317 Intermediate Similarity NPD6402 Approved
0.7302 Intermediate Similarity NPD6649 Approved
0.7302 Intermediate Similarity NPD6650 Approved
0.7258 Intermediate Similarity NPD5701 Approved
0.7258 Intermediate Similarity NPD5697 Approved
0.72 Intermediate Similarity NPD6881 Approved
0.72 Intermediate Similarity NPD6899 Approved
0.7197 Intermediate Similarity NPD8380 Approved
0.7197 Intermediate Similarity NPD8378 Approved
0.7197 Intermediate Similarity NPD8296 Approved
0.7197 Intermediate Similarity NPD8379 Approved
0.7197 Intermediate Similarity NPD8335 Approved
0.7154 Intermediate Similarity NPD6009 Approved
0.7143 Intermediate Similarity NPD6014 Approved
0.7143 Intermediate Similarity NPD6012 Approved
0.7143 Intermediate Similarity NPD6013 Approved
0.7121 Intermediate Similarity NPD8294 Approved
0.7121 Intermediate Similarity NPD8377 Approved
0.7109 Intermediate Similarity NPD6882 Approved
0.7107 Intermediate Similarity NPD7638 Approved
0.7101 Intermediate Similarity NPD7260 Phase 2
0.7087 Intermediate Similarity NPD6883 Approved
0.7087 Intermediate Similarity NPD4634 Approved
0.7087 Intermediate Similarity NPD7290 Approved
0.7087 Intermediate Similarity NPD7102 Approved
0.7068 Intermediate Similarity NPD8033 Approved
0.7068 Intermediate Similarity NPD5983 Phase 2
0.7063 Intermediate Similarity NPD6011 Approved
0.7059 Intermediate Similarity NPD8074 Phase 3
0.705 Intermediate Similarity NPD6845 Suspended
0.7049 Intermediate Similarity NPD7639 Approved
0.7049 Intermediate Similarity NPD7640 Approved
0.704 Intermediate Similarity NPD6008 Approved
0.7031 Intermediate Similarity NPD6869 Approved
0.7031 Intermediate Similarity NPD6617 Approved
0.7031 Intermediate Similarity NPD8130 Phase 1
0.7031 Intermediate Similarity NPD6847 Approved
0.7008 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD6033 Approved
0.6984 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6977 Remote Similarity NPD6053 Discontinued
0.6963 Remote Similarity NPD7604 Phase 2
0.6917 Remote Similarity NPD5282 Discontinued
0.6899 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6885 Remote Similarity NPD4755 Approved
0.6861 Remote Similarity NPD6336 Discontinued
0.6853 Remote Similarity NPD7966 Clinical (unspecified phase)
0.685 Remote Similarity NPD6412 Phase 2
0.6829 Remote Similarity NPD5696 Approved
0.6818 Remote Similarity NPD6274 Approved
0.68 Remote Similarity NPD5211 Phase 2
0.6794 Remote Similarity NPD8133 Approved
0.6774 Remote Similarity NPD5286 Approved
0.6774 Remote Similarity NPD4696 Approved
0.6774 Remote Similarity NPD5285 Approved
0.6774 Remote Similarity NPD4700 Approved
0.6769 Remote Similarity NPD8413 Clinical (unspecified phase)
0.675 Remote Similarity NPD6411 Approved
0.6748 Remote Similarity NPD6083 Phase 2
0.6748 Remote Similarity NPD6084 Phase 2
0.6748 Remote Similarity NPD7902 Approved
0.6694 Remote Similarity NPD5779 Approved
0.6694 Remote Similarity NPD5778 Approved
0.6693 Remote Similarity NPD5141 Approved
0.6691 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7100 Approved
0.6667 Remote Similarity NPD5225 Approved
0.6667 Remote Similarity NPD6698 Approved
0.6667 Remote Similarity NPD4697 Phase 3
0.6667 Remote Similarity NPD4633 Approved
0.6667 Remote Similarity NPD5226 Approved
0.6667 Remote Similarity NPD5224 Approved
0.6667 Remote Similarity NPD46 Approved
0.6667 Remote Similarity NPD7101 Approved
0.6642 Remote Similarity NPD6317 Approved
0.6641 Remote Similarity NPD4767 Approved
0.6641 Remote Similarity NPD4768 Approved
0.6639 Remote Similarity NPD7748 Approved
0.6614 Remote Similarity NPD5174 Approved
0.6614 Remote Similarity NPD5175 Approved
0.6612 Remote Similarity NPD7515 Phase 2
0.6612 Remote Similarity NPD7983 Approved
0.6593 Remote Similarity NPD6335 Approved
0.6593 Remote Similarity NPD6314 Approved
0.6593 Remote Similarity NPD6313 Approved
0.6587 Remote Similarity NPD5344 Discontinued
0.6587 Remote Similarity NPD5223 Approved
0.6585 Remote Similarity NPD5695 Phase 3
0.6585 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6583 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6583 Remote Similarity NPD6101 Approved
0.6569 Remote Similarity NPD6908 Approved
0.6569 Remote Similarity NPD6909 Approved
0.6565 Remote Similarity NPD6371 Approved
0.6555 Remote Similarity NPD3573 Approved
0.6538 Remote Similarity NPD4729 Approved
0.6538 Remote Similarity NPD4730 Approved
0.6535 Remote Similarity NPD7632 Discontinued
0.6532 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6532 Remote Similarity NPD5222 Approved
0.6532 Remote Similarity NPD5221 Approved
0.6508 Remote Similarity NPD6648 Approved
0.6504 Remote Similarity NPD7900 Approved
0.6504 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6491 Remote Similarity NPD8434 Phase 2
0.6484 Remote Similarity NPD4754 Approved
0.648 Remote Similarity NPD5173 Approved
0.6475 Remote Similarity NPD5693 Phase 1
0.6471 Remote Similarity NPD3618 Phase 1
0.6463 Remote Similarity NPD6333 Approved
0.6463 Remote Similarity NPD6334 Approved
0.6457 Remote Similarity NPD1700 Approved
0.6446 Remote Similarity NPD5328 Approved
0.6446 Remote Similarity NPD7799 Discontinued
0.6444 Remote Similarity NPD6868 Approved
0.6439 Remote Similarity NPD5249 Phase 3
0.6439 Remote Similarity NPD5247 Approved
0.6439 Remote Similarity NPD5250 Approved
0.6439 Remote Similarity NPD5251 Approved
0.6439 Remote Similarity NPD5248 Approved
0.6434 Remote Similarity NPD5956 Approved
0.6423 Remote Similarity NPD6399 Phase 3
0.6412 Remote Similarity NPD5128 Approved
0.641 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6387 Remote Similarity NPD1694 Approved
0.6374 Remote Similarity NPD8407 Phase 2
0.6364 Remote Similarity NPD6672 Approved
0.6364 Remote Similarity NPD5737 Approved
0.6341 Remote Similarity NPD6079 Approved
0.6341 Remote Similarity NPD7637 Suspended
0.632 Remote Similarity NPD5210 Approved
0.632 Remote Similarity NPD6356 Clinical (unspecified phase)
0.632 Remote Similarity NPD4629 Approved
0.6311 Remote Similarity NPD4753 Phase 2
0.6311 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6299 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6294 Remote Similarity NPD8368 Discontinued
0.629 Remote Similarity NPD4202 Approved
0.6269 Remote Similarity NPD5216 Approved
0.6269 Remote Similarity NPD5217 Approved
0.6269 Remote Similarity NPD5215 Approved
0.626 Remote Similarity NPD5692 Phase 3
0.626 Remote Similarity NPD7838 Discovery
0.6258 Remote Similarity NPD7236 Approved
0.6241 Remote Similarity NPD6067 Discontinued
0.622 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6218 Remote Similarity NPD6110 Phase 1
0.6216 Remote Similarity NPD8387 Clinical (unspecified phase)
0.621 Remote Similarity NPD5284 Approved
0.621 Remote Similarity NPD5281 Approved
0.621 Remote Similarity NPD8035 Phase 2
0.621 Remote Similarity NPD5694 Approved
0.621 Remote Similarity NPD6050 Approved
0.621 Remote Similarity NPD8034 Phase 2
0.6198 Remote Similarity NPD5279 Phase 3
0.6198 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6194 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6194 Remote Similarity NPD5135 Approved
0.6194 Remote Similarity NPD5169 Approved
0.6179 Remote Similarity NPD6080 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