Structure

Physi-Chem Properties

Molecular Weight:  324.06
Volume:  308.752
LogP:  3.401
LogD:  2.712
LogS:  -4.224
# Rotatable Bonds:  1
TPSA:  78.13
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.693
Synthetic Accessibility Score:  3.791
Fsp3:  0.167
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:  -4.926
MDCK Permeability:  2.3222430172609165e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.373

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.036
Plasma Protein Binding (PPB):  81.73944091796875%
Volume Distribution (VD):  0.967
Pgp-substrate:  17.2968807220459%

ADMET: Metabolism

CYP1A2-inhibitor:  0.88
CYP1A2-substrate:  0.818
CYP2C19-inhibitor:  0.769
CYP2C19-substrate:  0.325
CYP2C9-inhibitor:  0.896
CYP2C9-substrate:  0.853
CYP2D6-inhibitor:  0.843
CYP2D6-substrate:  0.204
CYP3A4-inhibitor:  0.671
CYP3A4-substrate:  0.17

ADMET: Excretion

Clearance (CL):  2.732
Half-life (T1/2):  0.487

ADMET: Toxicity

hERG Blockers:  0.045
Human Hepatotoxicity (H-HT):  0.959
Drug-inuced Liver Injury (DILI):  0.974
AMES Toxicity:  0.99
Rat Oral Acute Toxicity:  0.937
Maximum Recommended Daily Dose:  0.945
Skin Sensitization:  0.695
Carcinogencity:  0.987
Eye Corrosion:  0.005
Eye Irritation:  0.257
Respiratory Toxicity:  0.936

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

  Natural Product: NPC211482

Natural Product ID:  NPC211482
Common Name*:   Sterigmatocystin
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  UTSVPXMQSFGQTM-DCXZOGHSSA-N
Standard InCHI:  InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
SMILES:  COc1cc2c([C@@H]3C=CO[C@@H]3O2)c2c1c(=O)c1c(cccc1o2)O
Synthetic Gene Cluster:   BGC0000011;BGC0000152;
ChEMBL Identifier:   CHEMBL524291
PubChem CID:   5280389
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0001817] Sterigmatocystins

*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
NPO27885.1 Aspergillus nidulans var. acristatus Varieties Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16872131]
NPO40600 Aspergillus sp. AST0036 Strain Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24251417]
NPO27885.1 Aspergillus nidulans var. acristatus Varieties Aspergillaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 2223.31 nM PMID[561981]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 1510.08 nM PMID[561981]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 3147.75 nM PMID[561981]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 5571.86 nM PMID[561981]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 10447.2 nM PMID[561981]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 13772.09 nM PMID[561981]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 42953.64 nM PMID[561981]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 107151.93 nM PMID[561981]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 7943.28 nM PMID[561981]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 125025.9 nM PMID[561981]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 12359.47 nM PMID[561981]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 3258.37 nM PMID[561981]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 6412.1 nM PMID[561981]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 14893.61 nM PMID[561981]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 4655.86 nM PMID[561981]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 6471.43 nM PMID[561981]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 7673.61 nM PMID[561981]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 33806.48 nM PMID[561981]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 683.91 nM PMID[561981]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 7533.56 nM PMID[561981]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 34994.52 nM PMID[561981]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 42169.65 nM PMID[561981]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 14157.94 nM PMID[561981]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 2679.17 nM PMID[561981]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 101157.95 nM PMID[561981]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 76032.63 nM PMID[561981]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 60394.86 nM PMID[561981]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 115.08 nM PMID[561981]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 17864.88 nM PMID[561981]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 4168.69 nM PMID[561981]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 2741.57 nM PMID[561981]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 7709.03 nM PMID[561981]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 3698.28 nM PMID[561981]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 8279.42 nM PMID[561981]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 15100.8 nM PMID[561981]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 12022.64 nM PMID[561981]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 19142.56 nM PMID[561981]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 1028.02 nM PMID[561981]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 24.49 nM PMID[561981]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 11641.26 nM PMID[561981]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 19678.86 nM PMID[561981]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 3881.5 nM PMID[561981]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 937.56 nM PMID[561981]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 381.07 nM PMID[561981]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 1803.02 nM PMID[561981]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 13899.53 nM PMID[561981]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 12302.69 nM PMID[561981]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 32359.37 nM PMID[561981]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 36057.86 nM PMID[561981]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 19054.61 nM PMID[561981]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 451.86 nM PMID[561981]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 20941.12 nM PMID[561981]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 75857.76 nM PMID[561981]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 5308.84 nM PMID[561981]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 13803.84 nM PMID[561981]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 1905.46 nM PMID[561981]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 5069.91 nM PMID[561981]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 30060.76 nM PMID[561981]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 18.17 % PMID[561982]
NPT81 Cell Line A549 Homo sapiens Selectivity ratio = 80.0 n.a. PMID[561983]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 2750.0 nM PMID[561983]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 3630.0 nM PMID[561983]
NPT395 Cell Line SF-268 Homo sapiens IC50 = 2960.0 nM PMID[561983]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 3410.0 nM PMID[561983]
NPT1233 Organism Mycotypha microspora Mycotypha microspora IZ = 11.0 mm PMID[561980]
NPT1234 Organism Chlorella fusca Chlorella fusca IZ = 5.0 mm PMID[561980]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -2.65 % PMID[561982]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3230.0 nM PMID[561983]

☑ 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 NPC211482 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 NPC476652
0.9545 High Similarity NPC93215
0.9545 High Similarity NPC310603
0.9467 High Similarity NPC318424
0.9236 High Similarity NPC471286
0.9236 High Similarity NPC91288
0.92 High Similarity NPC308200
0.9195 High Similarity NPC271288
0.9139 High Similarity NPC39195
0.9139 High Similarity NPC145467
0.9128 High Similarity NPC113770
0.9103 High Similarity NPC50430
0.9091 High Similarity NPC121910
0.9091 High Similarity NPC168805
0.9079 High Similarity NPC471114
0.9067 High Similarity NPC311144
0.9067 High Similarity NPC184649
0.9067 High Similarity NPC303185
0.906 High Similarity NPC202981
0.906 High Similarity NPC266725
0.9038 High Similarity NPC23817
0.9038 High Similarity NPC470606
0.902 High Similarity NPC321896
0.902 High Similarity NPC476185
0.902 High Similarity NPC471115
0.902 High Similarity NPC29777
0.9013 High Similarity NPC168085
0.9007 High Similarity NPC477955
0.9007 High Similarity NPC299011
0.9007 High Similarity NPC472629
0.9007 High Similarity NPC73320
0.9 High Similarity NPC85162
0.9 High Similarity NPC125894
0.9 High Similarity NPC77794
0.9 High Similarity NPC223812
0.9 High Similarity NPC278249
0.9 High Similarity NPC107177
0.9 High Similarity NPC81697
0.8993 High Similarity NPC213322
0.8993 High Similarity NPC324386
0.8993 High Similarity NPC3188
0.8993 High Similarity NPC312391
0.8993 High Similarity NPC4743
0.8986 High Similarity NPC316480
0.8981 High Similarity NPC470607
0.8981 High Similarity NPC308265
0.8981 High Similarity NPC40583
0.8968 High Similarity NPC213608
0.8968 High Similarity NPC1477
0.8968 High Similarity NPC106625
0.8961 High Similarity NPC472636
0.8961 High Similarity NPC290671
0.8961 High Similarity NPC471291
0.8961 High Similarity NPC325429
0.8954 High Similarity NPC317492
0.8954 High Similarity NPC473016
0.8947 High Similarity NPC10990
0.8947 High Similarity NPC300988
0.8944 High Similarity NPC320789
0.894 High Similarity NPC87486
0.894 High Similarity NPC470890
0.894 High Similarity NPC235217
0.894 High Similarity NPC71210
0.894 High Similarity NPC131579
0.894 High Similarity NPC473015
0.894 High Similarity NPC131568
0.894 High Similarity NPC473013
0.894 High Similarity NPC473014
0.894 High Similarity NPC124780
0.8933 High Similarity NPC167624
0.8933 High Similarity NPC107572
0.8933 High Similarity NPC194432
0.8933 High Similarity NPC66515
0.8933 High Similarity NPC177354
0.8933 High Similarity NPC1089
0.8933 High Similarity NPC228504
0.8933 High Similarity NPC32739
0.8933 High Similarity NPC166934
0.8933 High Similarity NPC182852
0.8933 High Similarity NPC64915
0.8933 High Similarity NPC265040
0.8933 High Similarity NPC328164
0.8933 High Similarity NPC40833
0.8933 High Similarity NPC148757
0.8933 High Similarity NPC76372
0.8933 High Similarity NPC37496
0.8933 High Similarity NPC161506
0.8933 High Similarity NPC324134
0.8933 High Similarity NPC296917
0.8933 High Similarity NPC76338
0.8933 High Similarity NPC10937
0.8933 High Similarity NPC306829
0.8933 High Similarity NPC227579
0.8933 High Similarity NPC324436
0.8933 High Similarity NPC125855
0.8933 High Similarity NPC220998
0.8933 High Similarity NPC223500
0.8933 High Similarity NPC78
0.8933 High Similarity NPC166482
0.8931 High Similarity NPC131745
0.8931 High Similarity NPC44947
0.8931 High Similarity NPC259834
0.8931 High Similarity NPC469575
0.8931 High Similarity NPC125991
0.8926 High Similarity NPC284550
0.8926 High Similarity NPC76445
0.8926 High Similarity NPC129853
0.8924 High Similarity NPC19554
0.8924 High Similarity NPC43971
0.8924 High Similarity NPC271479
0.8924 High Similarity NPC472320
0.8924 High Similarity NPC74749
0.8919 High Similarity NPC118813
0.8917 High Similarity NPC161650
0.891 High Similarity NPC470603
0.891 High Similarity NPC470605
0.891 High Similarity NPC87404
0.891 High Similarity NPC99233
0.891 High Similarity NPC470604
0.891 High Similarity NPC92395
0.8903 High Similarity NPC166067
0.8903 High Similarity NPC473996
0.8903 High Similarity NPC5871
0.8903 High Similarity NPC259182
0.8903 High Similarity NPC121001
0.8896 High Similarity NPC475825
0.8896 High Similarity NPC223375
0.8882 High Similarity NPC127059
0.8882 High Similarity NPC285630
0.8882 High Similarity NPC290133
0.8882 High Similarity NPC24136
0.8882 High Similarity NPC187282
0.8875 High Similarity NPC66087
0.8875 High Similarity NPC183672
0.8875 High Similarity NPC179198
0.8875 High Similarity NPC278419
0.8875 High Similarity NPC124155
0.8875 High Similarity NPC257566
0.8874 High Similarity NPC169591
0.8874 High Similarity NPC310130
0.8874 High Similarity NPC164980
0.8874 High Similarity NPC185276
0.8874 High Similarity NPC257097
0.8874 High Similarity NPC214166
0.8874 High Similarity NPC221432
0.8874 High Similarity NPC39329
0.8874 High Similarity NPC106985
0.8874 High Similarity NPC175504
0.8874 High Similarity NPC143896
0.8874 High Similarity NPC91560
0.8874 High Similarity NPC149026
0.8874 High Similarity NPC68104
0.8874 High Similarity NPC316816
0.8874 High Similarity NPC478086
0.8874 High Similarity NPC150408
0.8874 High Similarity NPC75049
0.8874 High Similarity NPC166138
0.8874 High Similarity NPC18585
0.8868 High Similarity NPC47923
0.8867 High Similarity NPC110038
0.8867 High Similarity NPC166689
0.8867 High Similarity NPC17170
0.8867 High Similarity NPC248372
0.8867 High Similarity NPC282300
0.8867 High Similarity NPC156190
0.8867 High Similarity NPC279650
0.8867 High Similarity NPC258630
0.8867 High Similarity NPC96408
0.8861 High Similarity NPC311574
0.8861 High Similarity NPC264932
0.8861 High Similarity NPC73511
0.8859 High Similarity NPC222342
0.8859 High Similarity NPC265871
0.8859 High Similarity NPC20709
0.8859 High Similarity NPC225153
0.8859 High Similarity NPC18260
0.8859 High Similarity NPC274784
0.8859 High Similarity NPC78913
0.8859 High Similarity NPC150648
0.8859 High Similarity NPC261234
0.8859 High Similarity NPC329203
0.8859 High Similarity NPC310135
0.8854 High Similarity NPC265480
0.8854 High Similarity NPC127406
0.8854 High Similarity NPC206378
0.8854 High Similarity NPC17521
0.8854 High Similarity NPC149368
0.8846 High Similarity NPC268950
0.8846 High Similarity NPC108706
0.8846 High Similarity NPC78021
0.8846 High Similarity NPC211158
0.8846 High Similarity NPC87304
0.8839 High Similarity NPC78835
0.8839 High Similarity NPC309512
0.8839 High Similarity NPC209142
0.8839 High Similarity NPC190217
0.8839 High Similarity NPC312549
0.8839 High Similarity NPC178484
0.8839 High Similarity NPC471675
0.8839 High Similarity NPC204561

  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 NPC211482 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
0.8816 High Similarity NPD4378 Clinical (unspecified phase)
0.8797 High Similarity NPD4381 Clinical (unspecified phase)
0.8725 High Similarity NPD1552 Clinical (unspecified phase)
0.8725 High Similarity NPD1550 Clinical (unspecified phase)
0.8671 High Similarity NPD8443 Clinical (unspecified phase)
0.8667 High Similarity NPD1549 Phase 2
0.8659 High Similarity NPD7804 Clinical (unspecified phase)
0.8608 High Similarity NPD2393 Clinical (unspecified phase)
0.8503 High Similarity NPD6559 Discontinued
0.8491 Intermediate Similarity NPD7819 Suspended
0.8485 Intermediate Similarity NPD3818 Discontinued
0.8481 Intermediate Similarity NPD7411 Suspended
0.8467 Intermediate Similarity NPD1510 Phase 2
0.8447 Intermediate Similarity NPD7075 Discontinued
0.8428 Intermediate Similarity NPD1934 Approved
0.8418 Intermediate Similarity NPD4380 Phase 2
0.8383 Intermediate Similarity NPD7074 Phase 3
0.8375 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8366 Intermediate Similarity NPD2800 Approved
0.8333 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD7054 Approved
0.8322 Intermediate Similarity NPD1240 Approved
0.8289 Intermediate Similarity NPD2796 Approved
0.8274 Intermediate Similarity NPD7472 Approved
0.8253 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD5494 Approved
0.8225 Intermediate Similarity NPD6797 Phase 2
0.8221 Intermediate Similarity NPD3749 Approved
0.8212 Intermediate Similarity NPD1607 Approved
0.8182 Intermediate Similarity NPD6959 Discontinued
0.8176 Intermediate Similarity NPD7251 Discontinued
0.816 Intermediate Similarity NPD7768 Phase 2
0.8153 Intermediate Similarity NPD1511 Approved
0.8129 Intermediate Similarity NPD7808 Phase 3
0.8113 Intermediate Similarity NPD920 Approved
0.8101 Intermediate Similarity NPD2533 Approved
0.8101 Intermediate Similarity NPD2532 Approved
0.8101 Intermediate Similarity NPD2534 Approved
0.8086 Intermediate Similarity NPD6801 Discontinued
0.8077 Intermediate Similarity NPD3750 Approved
0.8065 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.805 Intermediate Similarity NPD1512 Approved
0.8049 Intermediate Similarity NPD3882 Suspended
0.8038 Intermediate Similarity NPD6799 Approved
0.8037 Intermediate Similarity NPD2801 Approved
0.8023 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD1243 Approved
0.7987 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD6599 Discontinued
0.7962 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD1551 Phase 2
0.7929 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD6166 Phase 2
0.7929 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD2344 Approved
0.7882 Intermediate Similarity NPD7473 Discontinued
0.7879 Intermediate Similarity NPD3817 Phase 2
0.7871 Intermediate Similarity NPD2799 Discontinued
0.7829 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD2935 Discontinued
0.7811 Intermediate Similarity NPD6232 Discontinued
0.7756 Intermediate Similarity NPD3748 Approved
0.7751 Intermediate Similarity NPD7199 Phase 2
0.7742 Intermediate Similarity NPD6651 Approved
0.7725 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD2313 Discontinued
0.7703 Intermediate Similarity NPD1610 Phase 2
0.7702 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD5953 Discontinued
0.7697 Intermediate Similarity NPD4908 Phase 1
0.7688 Intermediate Similarity NPD7286 Phase 2
0.7688 Intermediate Similarity NPD2309 Approved
0.7688 Intermediate Similarity NPD5844 Phase 1
0.7683 Intermediate Similarity NPD3226 Approved
0.7683 Intermediate Similarity NPD7458 Discontinued
0.7682 Intermediate Similarity NPD2798 Approved
0.767 Intermediate Similarity NPD8313 Approved
0.767 Intermediate Similarity NPD8312 Approved
0.7669 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD2346 Discontinued
0.7633 Intermediate Similarity NPD6234 Discontinued
0.7633 Intermediate Similarity NPD919 Approved
0.7619 Intermediate Similarity NPD4965 Approved
0.7619 Intermediate Similarity NPD4966 Approved
0.7619 Intermediate Similarity NPD4967 Phase 2
0.7602 Intermediate Similarity NPD5710 Approved
0.7602 Intermediate Similarity NPD5711 Approved
0.7595 Intermediate Similarity NPD6099 Approved
0.7595 Intermediate Similarity NPD6100 Approved
0.7582 Intermediate Similarity NPD4360 Phase 2
0.7582 Intermediate Similarity NPD4363 Phase 3
0.7561 Intermediate Similarity NPD5403 Approved
0.7547 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD5401 Approved
0.7545 Intermediate Similarity NPD37 Approved
0.7544 Intermediate Similarity NPD1247 Approved
0.7541 Intermediate Similarity NPD4361 Phase 2
0.7541 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7228 Approved
0.7516 Intermediate Similarity NPD4628 Phase 3
0.7516 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD7584 Approved
0.75 Intermediate Similarity NPD1203 Approved
0.75 Intermediate Similarity NPD7229 Phase 3
0.75 Intermediate Similarity NPD8455 Phase 2
0.7485 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3268 Approved
0.7467 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD5402 Approved
0.7452 Intermediate Similarity NPD1933 Approved
0.7439 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD3751 Discontinued
0.7421 Intermediate Similarity NPD7033 Discontinued
0.7396 Intermediate Similarity NPD1465 Phase 2
0.7389 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD2797 Approved
0.738 Intermediate Similarity NPD6779 Approved
0.738 Intermediate Similarity NPD6776 Approved
0.738 Intermediate Similarity NPD6780 Approved
0.738 Intermediate Similarity NPD6781 Approved
0.738 Intermediate Similarity NPD6778 Approved
0.738 Intermediate Similarity NPD6782 Approved
0.738 Intermediate Similarity NPD6777 Approved
0.7378 Intermediate Similarity NPD7390 Discontinued
0.7356 Intermediate Similarity NPD3926 Phase 2
0.7355 Intermediate Similarity NPD6832 Phase 2
0.7342 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD5124 Phase 1
0.7329 Intermediate Similarity NPD6002 Phase 3
0.7329 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6004 Phase 3
0.7329 Intermediate Similarity NPD6005 Phase 3
0.7315 Intermediate Similarity NPD1548 Phase 1
0.7303 Intermediate Similarity NPD9717 Approved
0.7303 Intermediate Similarity NPD1608 Approved
0.7303 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD3787 Discontinued
0.7278 Intermediate Similarity NPD943 Approved
0.7273 Intermediate Similarity NPD3267 Approved
0.7273 Intermediate Similarity NPD3266 Approved
0.7268 Intermediate Similarity NPD4287 Approved
0.7263 Intermediate Similarity NPD7697 Approved
0.7263 Intermediate Similarity NPD7698 Approved
0.7263 Intermediate Similarity NPD7696 Phase 3
0.7263 Intermediate Similarity NPD7435 Discontinued
0.7262 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD3764 Approved
0.7254 Intermediate Similarity NPD8151 Discontinued
0.7247 Intermediate Similarity NPD1729 Discontinued
0.7239 Intermediate Similarity NPD2654 Approved
0.7237 Intermediate Similarity NPD422 Phase 1
0.7233 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD7871 Phase 2
0.7225 Intermediate Similarity NPD7870 Phase 2
0.7205 Intermediate Similarity NPD4308 Phase 3
0.7197 Intermediate Similarity NPD4625 Phase 3
0.7193 Intermediate Similarity NPD5760 Phase 2
0.7193 Intermediate Similarity NPD5761 Phase 2
0.7179 Intermediate Similarity NPD2861 Phase 2
0.7179 Intermediate Similarity NPD7783 Phase 2
0.7179 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD1613 Approved
0.7167 Intermediate Similarity NPD7685 Pre-registration
0.7167 Intermediate Similarity NPD7240 Approved
0.7158 Intermediate Similarity NPD8434 Phase 2
0.7157 Intermediate Similarity NPD7930 Approved
0.7151 Intermediate Similarity NPD4288 Approved
0.7151 Intermediate Similarity NPD2296 Approved
0.7135 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD230 Phase 1
0.7125 Intermediate Similarity NPD6355 Discontinued
0.712 Intermediate Similarity NPD6823 Phase 2
0.7119 Intermediate Similarity NPD2403 Approved
0.7117 Intermediate Similarity NPD1471 Phase 3
0.7113 Intermediate Similarity NPD7701 Phase 2
0.7113 Intermediate Similarity NPD7585 Approved
0.7112 Intermediate Similarity NPD6534 Approved
0.7112 Intermediate Similarity NPD6535 Approved
0.7105 Intermediate Similarity NPD17 Approved
0.7105 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD1653 Approved
0.7097 Intermediate Similarity NPD3225 Approved
0.7092 Intermediate Similarity NPD7801 Approved
0.7091 Intermediate Similarity NPD7003 Approved
0.7086 Intermediate Similarity NPD9545 Approved
0.707 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7583 Approved
0.7051 Intermediate Similarity NPD1164 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