Structure

Physi-Chem Properties

Molecular Weight:  534.15
Volume:  517.702
LogP:  4.928
LogD:  2.376
LogS:  -7.157
# Rotatable Bonds:  6
TPSA:  151.98
# H-Bond Aceptor:  10
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.189
Synthetic Accessibility Score:  4.341
Fsp3:  0.31
Lipinski Rule-of-5:  Accepted
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:  -5.149
MDCK Permeability:  8.597958185418975e-06
Pgp-inhibitor:  0.207
Pgp-substrate:  0.756
Human Intestinal Absorption (HIA):  0.243
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.009
Plasma Protein Binding (PPB):  80.02509307861328%
Volume Distribution (VD):  1.052
Pgp-substrate:  21.3736515045166%

ADMET: Metabolism

CYP1A2-inhibitor:  0.418
CYP1A2-substrate:  0.756
CYP2C19-inhibitor:  0.116
CYP2C19-substrate:  0.137
CYP2C9-inhibitor:  0.586
CYP2C9-substrate:  0.908
CYP2D6-inhibitor:  0.068
CYP2D6-substrate:  0.196
CYP3A4-inhibitor:  0.088
CYP3A4-substrate:  0.072

ADMET: Excretion

Clearance (CL):  1.204
Half-life (T1/2):  0.152

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.044
Drug-inuced Liver Injury (DILI):  0.84
AMES Toxicity:  0.291
Rat Oral Acute Toxicity:  0.033
Maximum Recommended Daily Dose:  0.183
Skin Sensitization:  0.221
Carcinogencity:  0.092
Eye Corrosion:  0.003
Eye Irritation:  0.303
Respiratory Toxicity:  0.063

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General Info & Identifiers & Properties  
Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC469486

Natural Product ID:  NPC469486
Common Name*:   Cercosporin
IUPAC Name:   n.a.
Synonyms:   Cercosporin
Standard InCHIKey:  DGAZLNHJYDOWLG-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C29H26O10/c1-10(30)5-12-18-19-13(6-11(2)31)29(37-4)27(35)21-15(33)8-17-23(25(19)21)22-16(38-9-39-17)7-14(32)20(24(18)22)26(34)28(12)36-3/h7-8,10-11,30-33H,5-6,9H2,1-4H3
SMILES:  COC1=C(CC(O)C)c2c3C(=C(OC)C(=O)c4c3c3c5c2c(C1=O)c(O)cc5OCOc3cc4O)CC(O)C
Synthetic Gene Cluster:   BGC0001541;BGC0001542;
ChEMBL Identifier:   CHEMBL1080283
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002903] Perylenequinones

*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
NPO17999 Sonneratia alba Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[19835393]
NPO17999 Sonneratia alba Species Lythraceae 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. 1573.98 nM PMID[508806]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 1399.59 nM PMID[508806]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 2142.89 nM PMID[508806]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 1629.3 nM PMID[508806]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 968.28 nM PMID[508806]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 2301.44 nM PMID[508806]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2133.04 nM PMID[508806]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 1520.55 nM PMID[508806]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 374.11 nM PMID[508806]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 1999.86 nM PMID[508806]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 1866.38 nM PMID[508806]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 1986.09 nM PMID[508806]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 1749.85 nM PMID[508806]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 1717.91 nM PMID[508806]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 1737.8 nM PMID[508806]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 2884.03 nM PMID[508806]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 905.73 nM PMID[508806]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 2494.59 nM PMID[508806]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 1367.73 nM PMID[508806]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 2618.18 nM PMID[508806]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 663.74 nM PMID[508806]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 2098.94 nM PMID[508806]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 1819.7 nM PMID[508806]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 1288.25 nM PMID[508806]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 1621.81 nM PMID[508806]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 1823.9 nM PMID[508806]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 2103.78 nM PMID[508806]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 1380.38 nM PMID[508806]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 711.21 nM PMID[508806]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 1545.25 nM PMID[508806]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 300.61 nM PMID[508806]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 1651.96 nM PMID[508806]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 2382.32 nM PMID[508806]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 1559.55 nM PMID[508806]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 1807.17 nM PMID[508806]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1386.76 nM PMID[508806]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 1563.15 nM PMID[508806]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 427.56 nM PMID[508806]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 4140.0 nM PMID[508806]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 449.78 nM PMID[508806]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 1782.38 nM PMID[508806]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 6011.74 nM PMID[508806]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 1914.26 nM PMID[508806]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 1694.34 nM PMID[508806]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 2152.78 nM PMID[508806]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 2660.73 nM PMID[508806]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 1958.84 nM PMID[508806]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 1339.68 nM PMID[508806]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 2722.7 nM PMID[508806]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 2290.87 nM PMID[508806]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 363.92 nM PMID[508806]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 1857.8 nM PMID[508806]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 1270.57 nM PMID[508806]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 157.76 nM PMID[508806]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 2576.32 nM PMID[508806]
NPT26688 PROTEIN COMPLEX TCF4-CTNNB1 complex Homo sapiens IC50 = 8700.0 nM PMID[508807]

☑ 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 NPC469486 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 NPC264063
0.9814 High Similarity NPC229051
0.9691 High Similarity NPC131862
0.9371 High Similarity NPC228654
0.9255 High Similarity NPC219686
0.9217 High Similarity NPC470336
0.9217 High Similarity NPC470335
0.8941 High Similarity NPC470334
0.8895 High Similarity NPC470332
0.8876 High Similarity NPC470333
0.8862 High Similarity NPC472058
0.8862 High Similarity NPC470341
0.8862 High Similarity NPC234497
0.8862 High Similarity NPC324522
0.8862 High Similarity NPC105414
0.881 High Similarity NPC259905
0.8802 High Similarity NPC178851
0.878 High Similarity NPC324736
0.8779 High Similarity NPC277710
0.8779 High Similarity NPC299149
0.8779 High Similarity NPC114257
0.8779 High Similarity NPC153578
0.8765 High Similarity NPC213052
0.8757 High Similarity NPC298778
0.8743 High Similarity NPC472057
0.8743 High Similarity NPC469664
0.8743 High Similarity NPC472051
0.8735 High Similarity NPC472059
0.8735 High Similarity NPC15374
0.8728 High Similarity NPC315221
0.872 High Similarity NPC474637
0.8706 High Similarity NPC5029
0.8706 High Similarity NPC271385
0.8706 High Similarity NPC111536
0.8706 High Similarity NPC76128
0.8706 High Similarity NPC30432
0.8698 High Similarity NPC470206
0.8698 High Similarity NPC470207
0.8683 High Similarity NPC290160
0.8683 High Similarity NPC472053
0.8678 High Similarity NPC313452
0.8663 High Similarity NPC475246
0.8663 High Similarity NPC46958
0.8642 High Similarity NPC470569
0.8625 High Similarity NPC34802
0.8614 High Similarity NPC186325
0.8614 High Similarity NPC472060
0.8614 High Similarity NPC472052
0.8614 High Similarity NPC470342
0.8605 High Similarity NPC63105
0.8605 High Similarity NPC477991
0.8605 High Similarity NPC474345
0.8605 High Similarity NPC3718
0.8605 High Similarity NPC68381
0.8605 High Similarity NPC477992
0.8598 High Similarity NPC66508
0.8598 High Similarity NPC226656
0.858 High Similarity NPC477835
0.858 High Similarity NPC87583
0.858 High Similarity NPC470568
0.858 High Similarity NPC147735
0.8571 High Similarity NPC475662
0.8571 High Similarity NPC473631
0.8571 High Similarity NPC293227
0.8571 High Similarity NPC473717
0.8571 High Similarity NPC472841
0.8563 High Similarity NPC70318
0.8563 High Similarity NPC273467
0.8563 High Similarity NPC472261
0.8563 High Similarity NPC18380
0.8563 High Similarity NPC189552
0.8555 High Similarity NPC475233
0.8554 High Similarity NPC177650
0.8547 High Similarity NPC98776
0.8547 High Similarity NPC472054
0.8547 High Similarity NPC85368
0.8547 High Similarity NPC470199
0.8547 High Similarity NPC314459
0.8547 High Similarity NPC154986
0.8539 High Similarity NPC314672
0.8528 High Similarity NPC72958
0.8528 High Similarity NPC232645
0.8528 High Similarity NPC474417
0.8528 High Similarity NPC149526
0.8519 High Similarity NPC329933
0.8514 High Similarity NPC477860
0.8514 High Similarity NPC475161
0.8512 High Similarity NPC216752
0.8506 High Similarity NPC477683
0.8506 High Similarity NPC477682
0.8506 High Similarity NPC47191
0.8503 High Similarity NPC292863
0.8503 High Similarity NPC312993
0.8503 High Similarity NPC284495
0.8503 High Similarity NPC184326
0.8497 Intermediate Similarity NPC470454
0.8497 Intermediate Similarity NPC470667
0.8497 Intermediate Similarity NPC199533
0.8492 Intermediate Similarity NPC48474
0.8491 Intermediate Similarity NPC84266
0.8488 Intermediate Similarity NPC477836
0.8488 Intermediate Similarity NPC473113
0.848 Intermediate Similarity NPC473095
0.848 Intermediate Similarity NPC222455
0.848 Intermediate Similarity NPC473202
0.848 Intermediate Similarity NPC473096
0.8476 Intermediate Similarity NPC87708
0.8475 Intermediate Similarity NPC475220
0.8475 Intermediate Similarity NPC475352
0.8475 Intermediate Similarity NPC229817
0.8475 Intermediate Similarity NPC221140
0.8475 Intermediate Similarity NPC473686
0.8471 Intermediate Similarity NPC178173
0.8466 Intermediate Similarity NPC325983
0.8466 Intermediate Similarity NPC290954
0.8466 Intermediate Similarity NPC255641
0.8462 Intermediate Similarity NPC66087
0.8462 Intermediate Similarity NPC278419
0.8462 Intermediate Similarity NPC179198
0.8457 Intermediate Similarity NPC84494
0.8457 Intermediate Similarity NPC245059
0.8457 Intermediate Similarity NPC244903
0.8457 Intermediate Similarity NPC212290
0.8453 Intermediate Similarity NPC470195
0.8453 Intermediate Similarity NPC470196
0.8453 Intermediate Similarity NPC316274
0.8453 Intermediate Similarity NPC470197
0.8453 Intermediate Similarity NPC282474
0.8453 Intermediate Similarity NPC470198
0.8453 Intermediate Similarity NPC470193
0.8453 Intermediate Similarity NPC470194
0.8453 Intermediate Similarity NPC470200
0.8452 Intermediate Similarity NPC137232
0.8443 Intermediate Similarity NPC195167
0.8443 Intermediate Similarity NPC51760
0.8434 Intermediate Similarity NPC164244
0.8434 Intermediate Similarity NPC146211
0.843 Intermediate Similarity NPC477573
0.843 Intermediate Similarity NPC477572
0.843 Intermediate Similarity NPC477571
0.8428 Intermediate Similarity NPC94076
0.8428 Intermediate Similarity NPC182255
0.8427 Intermediate Similarity NPC105591
0.8424 Intermediate Similarity NPC193200
0.8424 Intermediate Similarity NPC329844
0.8424 Intermediate Similarity NPC155686
0.8421 Intermediate Similarity NPC473094
0.8415 Intermediate Similarity NPC478148
0.8415 Intermediate Similarity NPC230848
0.8409 Intermediate Similarity NPC470452
0.8409 Intermediate Similarity NPC470448
0.8409 Intermediate Similarity NPC164047
0.8409 Intermediate Similarity NPC470453
0.8405 Intermediate Similarity NPC100985
0.8405 Intermediate Similarity NPC158338
0.8405 Intermediate Similarity NPC97028
0.8405 Intermediate Similarity NPC288036
0.8405 Intermediate Similarity NPC65589
0.8405 Intermediate Similarity NPC80370
0.8405 Intermediate Similarity NPC97029
0.8402 Intermediate Similarity NPC259834
0.8402 Intermediate Similarity NPC131745
0.84 Intermediate Similarity NPC5671
0.8395 Intermediate Similarity NPC190648
0.8395 Intermediate Similarity NPC312929
0.8395 Intermediate Similarity NPC290194
0.8395 Intermediate Similarity NPC245584
0.8395 Intermediate Similarity NPC126767
0.8395 Intermediate Similarity NPC289042
0.8395 Intermediate Similarity NPC56433
0.8395 Intermediate Similarity NPC118027
0.8393 Intermediate Similarity NPC472618
0.8391 Intermediate Similarity NPC186800
0.8391 Intermediate Similarity NPC294629
0.8391 Intermediate Similarity NPC146803
0.8389 Intermediate Similarity NPC321046
0.8385 Intermediate Similarity NPC28632
0.8383 Intermediate Similarity NPC281137
0.8383 Intermediate Similarity NPC282390
0.8383 Intermediate Similarity NPC246466
0.838 Intermediate Similarity NPC205721
0.8373 Intermediate Similarity NPC68727
0.8372 Intermediate Similarity NPC54903
0.8372 Intermediate Similarity NPC286074
0.8372 Intermediate Similarity NPC5319
0.8365 Intermediate Similarity NPC110810
0.8364 Intermediate Similarity NPC470340
0.8364 Intermediate Similarity NPC154683
0.8364 Intermediate Similarity NPC51824
0.8364 Intermediate Similarity NPC113608
0.8364 Intermediate Similarity NPC470338
0.8364 Intermediate Similarity NPC268992
0.8364 Intermediate Similarity NPC40356
0.8364 Intermediate Similarity NPC473967
0.8364 Intermediate Similarity NPC273483
0.8364 Intermediate Similarity NPC470337
0.8363 Intermediate Similarity NPC85047
0.8363 Intermediate Similarity NPC30027
0.8363 Intermediate Similarity NPC17274
0.8363 Intermediate Similarity NPC120857

  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 NPC469486 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
0.8788 High Similarity NPD6959 Discontinued
0.8372 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8324 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8294 Intermediate Similarity NPD6232 Discontinued
0.8256 Intermediate Similarity NPD7473 Discontinued
0.821 Intermediate Similarity NPD7390 Discontinued
0.8171 Intermediate Similarity NPD6797 Phase 2
0.8125 Intermediate Similarity NPD7251 Discontinued
0.8125 Intermediate Similarity NPD6559 Discontinued
0.8092 Intermediate Similarity NPD6166 Phase 2
0.8092 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD7808 Phase 3
0.8059 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8049 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD4380 Phase 2
0.8011 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD7074 Phase 3
0.7988 Intermediate Similarity NPD7819 Suspended
0.7955 Intermediate Similarity NPD7054 Approved
0.7955 Intermediate Similarity NPD5844 Phase 1
0.7953 Intermediate Similarity NPD7075 Discontinued
0.7939 Intermediate Similarity NPD2532 Approved
0.7939 Intermediate Similarity NPD2533 Approved
0.7939 Intermediate Similarity NPD2534 Approved
0.7929 Intermediate Similarity NPD6801 Discontinued
0.7914 Intermediate Similarity NPD6780 Approved
0.7914 Intermediate Similarity NPD6777 Approved
0.7914 Intermediate Similarity NPD6779 Approved
0.7914 Intermediate Similarity NPD6776 Approved
0.7914 Intermediate Similarity NPD6781 Approved
0.7914 Intermediate Similarity NPD6778 Approved
0.7914 Intermediate Similarity NPD6782 Approved
0.791 Intermediate Similarity NPD7472 Approved
0.7886 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7884 Intermediate Similarity NPD7435 Discontinued
0.7882 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD7411 Suspended
0.7865 Intermediate Similarity NPD8151 Discontinued
0.7842 Intermediate Similarity NPD7870 Phase 2
0.7842 Intermediate Similarity NPD7871 Phase 2
0.7833 Intermediate Similarity NPD8313 Approved
0.7833 Intermediate Similarity NPD8312 Approved
0.7831 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7797 Intermediate Similarity NPD3751 Discontinued
0.7797 Intermediate Similarity NPD3818 Discontinued
0.7789 Intermediate Similarity NPD7698 Approved
0.7789 Intermediate Similarity NPD7696 Phase 3
0.7789 Intermediate Similarity NPD7697 Approved
0.7778 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD37 Approved
0.7716 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD1510 Phase 2
0.7702 Intermediate Similarity NPD1607 Approved
0.7688 Intermediate Similarity NPD7768 Phase 2
0.7683 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD3787 Discontinued
0.7667 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6535 Approved
0.7647 Intermediate Similarity NPD6534 Approved
0.7641 Intermediate Similarity NPD7874 Approved
0.7641 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD3817 Phase 2
0.7629 Intermediate Similarity NPD7701 Phase 2
0.7622 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD1934 Approved
0.7609 Intermediate Similarity NPD8150 Discontinued
0.7602 Intermediate Similarity NPD6599 Discontinued
0.7586 Intermediate Similarity NPD4965 Approved
0.7586 Intermediate Similarity NPD4966 Approved
0.7586 Intermediate Similarity NPD4967 Phase 2
0.7586 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD1240 Approved
0.7576 Intermediate Similarity NPD1549 Phase 2
0.7544 Intermediate Similarity NPD7458 Discontinued
0.7544 Intermediate Similarity NPD3226 Approved
0.7543 Intermediate Similarity NPD3749 Approved
0.7529 Intermediate Similarity NPD5402 Approved
0.7526 Intermediate Similarity NPD7699 Phase 2
0.7526 Intermediate Similarity NPD7700 Phase 2
0.7513 Intermediate Similarity NPD7783 Phase 2
0.7513 Intermediate Similarity NPD7801 Approved
0.7513 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7228 Approved
0.75 Intermediate Similarity NPD6234 Discontinued
0.7486 Intermediate Similarity NPD3882 Suspended
0.7485 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD3750 Approved
0.7485 Intermediate Similarity NPD6651 Approved
0.7474 Intermediate Similarity NPD8320 Phase 1
0.7474 Intermediate Similarity NPD8319 Approved
0.7471 Intermediate Similarity NPD1512 Approved
0.7461 Intermediate Similarity NPD6823 Phase 2
0.7456 Intermediate Similarity NPD6799 Approved
0.7455 Intermediate Similarity NPD2796 Approved
0.7455 Intermediate Similarity NPD5406 Approved
0.7455 Intermediate Similarity NPD5408 Approved
0.7455 Intermediate Similarity NPD5404 Approved
0.7455 Intermediate Similarity NPD2935 Discontinued
0.7455 Intermediate Similarity NPD5405 Approved
0.7442 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.743 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD5403 Approved
0.7425 Intermediate Similarity NPD2800 Approved
0.7381 Intermediate Similarity NPD7003 Approved
0.7374 Intermediate Similarity NPD5710 Approved
0.7374 Intermediate Similarity NPD5711 Approved
0.7371 Intermediate Similarity NPD2801 Approved
0.7366 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD5494 Approved
0.7353 Intermediate Similarity NPD1511 Approved
0.7353 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD7199 Phase 2
0.731 Intermediate Similarity NPD5401 Approved
0.731 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1465 Phase 2
0.7273 Intermediate Similarity NPD8455 Phase 2
0.7225 Intermediate Similarity NPD6212 Phase 3
0.7225 Intermediate Similarity NPD6213 Phase 3
0.7225 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD2346 Discontinued
0.7186 Intermediate Similarity NPD3748 Approved
0.7172 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD7240 Approved
0.7143 Intermediate Similarity NPD6099 Approved
0.7143 Intermediate Similarity NPD6100 Approved
0.7143 Intermediate Similarity NPD1551 Phase 2
0.7126 Intermediate Similarity NPD920 Approved
0.7111 Intermediate Similarity NPD919 Approved
0.7088 Intermediate Similarity NPD7229 Phase 3
0.7083 Intermediate Similarity NPD2799 Discontinued
0.7076 Intermediate Similarity NPD4628 Phase 3
0.7076 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD3926 Phase 2
0.7033 Intermediate Similarity NPD1247 Approved
0.703 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD7177 Discontinued
0.7021 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD1243 Approved
0.7005 Intermediate Similarity NPD5953 Discontinued
0.7 Intermediate Similarity NPD1201 Approved
0.6994 Remote Similarity NPD2798 Approved
0.6989 Remote Similarity NPD7286 Phase 2
0.6982 Remote Similarity NPD651 Clinical (unspecified phase)
0.697 Remote Similarity NPD4625 Phase 3
0.6965 Remote Similarity NPD7584 Approved
0.6963 Remote Similarity NPD8434 Phase 2
0.6933 Remote Similarity NPD1470 Approved
0.6928 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4360 Phase 2
0.6923 Remote Similarity NPD4363 Phase 3
0.6916 Remote Similarity NPD8067 Phase 3
0.6914 Remote Similarity NPD642 Clinical (unspecified phase)
0.6909 Remote Similarity NPD4908 Phase 1
0.6901 Remote Similarity NPD2344 Approved
0.6897 Remote Similarity NPD643 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6273 Approved
0.6871 Remote Similarity NPD1283 Approved
0.6857 Remote Similarity NPD8366 Approved
0.6854 Remote Similarity NPD8059 Phase 3
0.6854 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6845 Remote Similarity NPD943 Approved
0.6845 Remote Similarity NPD7799 Discontinued
0.6839 Remote Similarity NPD6190 Approved
0.6821 Remote Similarity NPD6674 Discontinued
0.6813 Remote Similarity NPD1651 Approved
0.6812 Remote Similarity NPD7930 Approved
0.68 Remote Similarity NPD3300 Phase 2
0.6789 Remote Similarity NPD7685 Pre-registration
0.6788 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6784 Remote Similarity NPD7237 Clinical (unspecified phase)
0.675 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6746 Remote Similarity NPD2979 Phase 3
0.6746 Remote Similarity NPD4060 Phase 1
0.6744 Remote Similarity NPD2438 Suspended
0.6743 Remote Similarity NPD2309 Approved
0.6739 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6733 Remote Similarity NPD7680 Approved
0.6729 Remote Similarity NPD8491 Approved
0.6726 Remote Similarity NPD2313 Discontinued
0.6726 Remote Similarity NPD3764 Approved
0.6726 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6726 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6726 Remote Similarity NPD6798 Discontinued
0.6718 Remote Similarity NPD4287 Approved
0.6716 Remote Similarity NPD6973 Clinical (unspecified phase)
0.6714 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6706 Remote Similarity NPD230 Phase 1
0.6705 Remote Similarity NPD1471 Phase 3
0.6703 Remote Similarity NPD6746 Phase 2
0.6698 Remote Similarity NPD8469 Approved
0.6687 Remote Similarity NPD1281 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