Structure

Physi-Chem Properties

Molecular Weight:  324.02
Volume:  280.169
LogP:  1.542
LogD:  1.608
LogS:  -4.012
# Rotatable Bonds:  1
TPSA:  81.08
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.734
Synthetic Accessibility Score:  5.692
Fsp3:  0.385
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:  -4.851
MDCK Permeability:  2.1499245121958666e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.043
20% Bioavailability (F20%):  0.06
30% Bioavailability (F30%):  0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.537
Plasma Protein Binding (PPB):  64.01468658447266%
Volume Distribution (VD):  0.644
Pgp-substrate:  31.708457946777344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.19
CYP1A2-substrate:  0.3
CYP2C19-inhibitor:  0.909
CYP2C19-substrate:  0.939
CYP2C9-inhibitor:  0.932
CYP2C9-substrate:  0.832
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.129
CYP3A4-inhibitor:  0.478
CYP3A4-substrate:  0.969

ADMET: Excretion

Clearance (CL):  11.4
Half-life (T1/2):  0.819

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.149
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.055
Rat Oral Acute Toxicity:  0.512
Maximum Recommended Daily Dose:  0.006
Skin Sensitization:  0.777
Carcinogencity:  0.627
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.015

Download Data

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

  Natural Product: NPC166169

Natural Product ID:  NPC166169
Common Name*:   BNNLUYCZQNYABS-CHWSQXEVSA-N
IUPAC Name:   n.a.
Synonyms:   5A,6-Didehydrogliotoxin
Standard InCHIKey:  BNNLUYCZQNYABS-CHWSQXEVSA-N
Standard InCHI:  InChI=1S/C13H12N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,16-17H,5-6H2,1H3/t12-,13-/m1/s1
SMILES:  CN1C(=O)[C@]23Cc4cccc(c4N2C(=O)[C@@]1(CO)SS3)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1950961
PubChem CID:   13989137
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0002013] Indolecarboxylic acids 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
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10479323]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12350167]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[14640527]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota Axinella verrucosa Mediterranean n.a. PMID[14738391]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15043411]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Sussex Inlet, New South Wales, Australia n.a. PMID[15104517]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15332862]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Berkeley Pit lake n.a. PMID[17970594]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. New Zealand n.a. PMID[19323568]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19326880]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20452770]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. North Sea n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Limonium tubiflorum n.a. PMID[21146414]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21916432]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22148349]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22458669]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23360521]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23477451]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23603293]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23972215]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24437979]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31433188]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[9392888]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO9410 Saussurea macrota Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12137 Elysia tuca Species Placobranchidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10070 Scorzonera latifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3593 Lagochilus inebrians Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO45 Sterculia parviflora Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO677 Parmelia abessinica Species Parmeliaceae 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
NPT168 Cell Line P388 Mus musculus IC50 = 56.0 nM PMID[550402]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens IC50 = 2600.0 nM PMID[550402]

☑ 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 NPC166169 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
0.9458 High Similarity NPC302235
0.797 Intermediate Similarity NPC475609
0.7963 Intermediate Similarity NPC470301
0.7727 Intermediate Similarity NPC33507
0.7472 Intermediate Similarity NPC472114
0.7472 Intermediate Similarity NPC472115
0.7421 Intermediate Similarity NPC470485
0.7385 Intermediate Similarity NPC1464
0.7316 Intermediate Similarity NPC470483
0.7287 Intermediate Similarity NPC262725
0.7268 Intermediate Similarity NPC265642
0.7268 Intermediate Similarity NPC138615
0.7268 Intermediate Similarity NPC218733
0.7268 Intermediate Similarity NPC132874
0.7222 Intermediate Similarity NPC471124
0.7112 Intermediate Similarity NPC39822
0.711 Intermediate Similarity NPC146370
0.7095 Intermediate Similarity NPC471122
0.702 Intermediate Similarity NPC138830
0.7015 Intermediate Similarity NPC195787
0.7015 Intermediate Similarity NPC246140
0.7005 Intermediate Similarity NPC112937
0.7 Intermediate Similarity NPC301163
0.699 Remote Similarity NPC170333
0.6985 Remote Similarity NPC469732
0.6978 Remote Similarity NPC328270
0.6978 Remote Similarity NPC204867
0.6976 Remote Similarity NPC470481
0.6976 Remote Similarity NPC470482
0.6954 Remote Similarity NPC161804
0.6934 Remote Similarity NPC477394
0.6923 Remote Similarity NPC204970
0.6923 Remote Similarity NPC473004
0.6915 Remote Similarity NPC477179
0.6901 Remote Similarity NPC266994
0.6897 Remote Similarity NPC478075
0.6895 Remote Similarity NPC116096
0.6891 Remote Similarity NPC21425
0.6881 Remote Similarity NPC470484
0.6881 Remote Similarity NPC254850
0.6881 Remote Similarity NPC477178
0.6881 Remote Similarity NPC477180
0.6881 Remote Similarity NPC477181
0.6869 Remote Similarity NPC316282
0.6863 Remote Similarity NPC330683
0.6863 Remote Similarity NPC329567
0.6862 Remote Similarity NPC129624
0.685 Remote Similarity NPC67904
0.6847 Remote Similarity NPC470490
0.6847 Remote Similarity NPC477174
0.6847 Remote Similarity NPC477173
0.6845 Remote Similarity NPC257390
0.6837 Remote Similarity NPC74216
0.6831 Remote Similarity NPC191863
0.6831 Remote Similarity NPC133470
0.6831 Remote Similarity NPC289776
0.6821 Remote Similarity NPC251439
0.6814 Remote Similarity NPC470488
0.6794 Remote Similarity NPC234772
0.678 Remote Similarity NPC475259
0.678 Remote Similarity NPC471945
0.678 Remote Similarity NPC470491
0.678 Remote Similarity NPC471950
0.6777 Remote Similarity NPC288110
0.6777 Remote Similarity NPC222046
0.6776 Remote Similarity NPC122886
0.6772 Remote Similarity NPC476441
0.6761 Remote Similarity NPC125852
0.6761 Remote Similarity NPC71539
0.6761 Remote Similarity NPC148124
0.6761 Remote Similarity NPC250960
0.6753 Remote Similarity NPC150308
0.6749 Remote Similarity NPC476098
0.6748 Remote Similarity NPC471951
0.6748 Remote Similarity NPC471946
0.6748 Remote Similarity NPC477160
0.6744 Remote Similarity NPC242159
0.6744 Remote Similarity NPC313694
0.6742 Remote Similarity NPC473491
0.6742 Remote Similarity NPC470784
0.6742 Remote Similarity NPC474183
0.6739 Remote Similarity NPC472120
0.6739 Remote Similarity NPC472117
0.6739 Remote Similarity NPC472101
0.6735 Remote Similarity NPC5630
0.6732 Remote Similarity NPC212123
0.6732 Remote Similarity NPC270918
0.672 Remote Similarity NPC470548
0.6719 Remote Similarity NPC197335
0.6719 Remote Similarity NPC270301
0.6716 Remote Similarity NPC133156
0.6716 Remote Similarity NPC470489
0.6715 Remote Similarity NPC191817
0.6715 Remote Similarity NPC475359
0.6714 Remote Similarity NPC99724
0.6713 Remote Similarity NPC248903
0.6713 Remote Similarity NPC471513
0.6713 Remote Similarity NPC470480
0.6704 Remote Similarity NPC144691
0.6703 Remote Similarity NPC29285
0.6701 Remote Similarity NPC473007
0.6701 Remote Similarity NPC92803
0.6686 Remote Similarity NPC109580
0.6685 Remote Similarity NPC476268
0.6684 Remote Similarity NPC314659
0.6684 Remote Similarity NPC18890
0.6683 Remote Similarity NPC230313
0.6667 Remote Similarity NPC16188
0.6667 Remote Similarity NPC137627
0.6667 Remote Similarity NPC10653
0.6667 Remote Similarity NPC318525
0.6667 Remote Similarity NPC100863
0.6667 Remote Similarity NPC26928
0.6667 Remote Similarity NPC113946
0.6667 Remote Similarity NPC262166
0.6667 Remote Similarity NPC472106
0.6651 Remote Similarity NPC470821
0.6651 Remote Similarity NPC159815
0.665 Remote Similarity NPC22689
0.665 Remote Similarity NPC473569
0.665 Remote Similarity NPC174629
0.665 Remote Similarity NPC473008
0.665 Remote Similarity NPC105055
0.6649 Remote Similarity NPC469915
0.6636 Remote Similarity NPC46259
0.6622 Remote Similarity NPC184680
0.662 Remote Similarity NPC219397
0.6616 Remote Similarity NPC203628
0.6614 Remote Similarity NPC89831
0.6611 Remote Similarity NPC233702
0.6605 Remote Similarity NPC478141
0.6598 Remote Similarity NPC477159
0.6592 Remote Similarity NPC315829
0.6592 Remote Similarity NPC470785
0.658 Remote Similarity NPC298320
0.6579 Remote Similarity NPC139085
0.6579 Remote Similarity NPC214626
0.6579 Remote Similarity NPC477185
0.6579 Remote Similarity NPC476425
0.6579 Remote Similarity NPC251212
0.6575 Remote Similarity NPC477397
0.657 Remote Similarity NPC53344
0.6566 Remote Similarity NPC474059
0.6566 Remote Similarity NPC45389
0.6562 Remote Similarity NPC477187
0.6561 Remote Similarity NPC475204
0.6561 Remote Similarity NPC475123
0.6561 Remote Similarity NPC472118
0.656 Remote Similarity NPC473458
0.6559 Remote Similarity NPC476231
0.6559 Remote Similarity NPC85651
0.6554 Remote Similarity NPC471680
0.655 Remote Similarity NPC254957
0.6546 Remote Similarity NPC476428
0.6545 Remote Similarity NPC136797
0.6545 Remote Similarity NPC476227
0.6545 Remote Similarity NPC279871
0.6542 Remote Similarity NPC37957
0.6538 Remote Similarity NPC68967
0.6537 Remote Similarity NPC471436
0.6533 Remote Similarity NPC28510
0.6528 Remote Similarity NPC287152
0.6528 Remote Similarity NPC474815
0.652 Remote Similarity NPC127178
0.6519 Remote Similarity NPC241392
0.6516 Remote Similarity NPC477516
0.6515 Remote Similarity NPC284706
0.6509 Remote Similarity NPC2905
0.6509 Remote Similarity NPC148391
0.6505 Remote Similarity NPC309531
0.6505 Remote Similarity NPC472102
0.6504 Remote Similarity NPC477395
0.6503 Remote Similarity NPC244509
0.6497 Remote Similarity NPC87391
0.6493 Remote Similarity NPC127996
0.6493 Remote Similarity NPC305542
0.6493 Remote Similarity NPC10732
0.6488 Remote Similarity NPC232600
0.6486 Remote Similarity NPC244336
0.6485 Remote Similarity NPC303214
0.6484 Remote Similarity NPC202198
0.6482 Remote Similarity NPC128582
0.648 Remote Similarity NPC470824
0.6473 Remote Similarity NPC268077
0.6473 Remote Similarity NPC473422
0.6471 Remote Similarity NPC176983
0.6465 Remote Similarity NPC473815
0.6465 Remote Similarity NPC313804
0.6465 Remote Similarity NPC315804
0.6462 Remote Similarity NPC151781
0.6462 Remote Similarity NPC74562
0.6462 Remote Similarity NPC316181
0.6462 Remote Similarity NPC30749
0.6461 Remote Similarity NPC308197
0.6449 Remote Similarity NPC305984
0.6445 Remote Similarity NPC82541
0.6443 Remote Similarity NPC269750
0.6443 Remote Similarity NPC194671
0.6439 Remote Similarity NPC249040
0.6436 Remote Similarity NPC243626

  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 NPC166169 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
0.7095 Intermediate Similarity NPD5294 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD7449 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5137 Approved
0.6863 Remote Similarity NPD2907 Approved
0.6863 Remote Similarity NPD2906 Approved
0.6862 Remote Similarity NPD5603 Clinical (unspecified phase)
0.6816 Remote Similarity NPD6321 Discontinued
0.6811 Remote Similarity NPD5823 Approved
0.6804 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6798 Remote Similarity NPD4467 Phase 2
0.6798 Remote Similarity NPD4465 Phase 2
0.6796 Remote Similarity NPD5860 Discontinued
0.6796 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6782 Remote Similarity NPD7071 Clinical (unspecified phase)
0.6772 Remote Similarity NPD1544 Phase 1
0.6769 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6769 Remote Similarity NPD5620 Clinical (unspecified phase)
0.6758 Remote Similarity NPD1769 Discontinued
0.6754 Remote Similarity NPD6654 Clinical (unspecified phase)
0.6731 Remote Similarity NPD4492 Approved
0.6731 Remote Similarity NPD4494 Approved
0.6723 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6716 Remote Similarity NPD6644 Discontinued
0.6701 Remote Similarity NPD2327 Clinical (unspecified phase)
0.6699 Remote Similarity NPD4082 Approved
0.6682 Remote Similarity NPD3940 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7603 Discontinued
0.6618 Remote Similarity NPD6795 Clinical (unspecified phase)
0.6618 Remote Similarity NPD3472 Approved
0.6618 Remote Similarity NPD4022 Approved
0.6596 Remote Similarity NPD7126 Discontinued
0.6593 Remote Similarity NPD5639 Clinical (unspecified phase)
0.6584 Remote Similarity NPD5197 Approved
0.6584 Remote Similarity NPD5196 Approved
0.6584 Remote Similarity NPD5194 Approved
0.6584 Remote Similarity NPD5071 Phase 2
0.658 Remote Similarity NPD6878 Phase 2
0.658 Remote Similarity NPD6879 Phase 2
0.658 Remote Similarity NPD5445 Approved
0.6555 Remote Similarity NPD3372 Discontinued
0.6553 Remote Similarity NPD5102 Clinical (unspecified phase)
0.6553 Remote Similarity NPD4456 Clinical (unspecified phase)
0.6553 Remote Similarity NPD1294 Discontinued
0.6548 Remote Similarity NPD4515 Suspended
0.6538 Remote Similarity NPD6376 Discontinued
0.6536 Remote Similarity NPD3141 Discontinued
0.6532 Remote Similarity NPD2791 Discontinued
0.6528 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6524 Remote Similarity NPD1945 Phase 1
0.6513 Remote Similarity NPD3253 Clinical (unspecified phase)
0.6495 Remote Similarity NPD6297 Approved
0.6493 Remote Similarity NPD3888 Discontinued
0.649 Remote Similarity NPD4596 Phase 1
0.6462 Remote Similarity NPD4455 Discontinued
0.6458 Remote Similarity NPD5938 Phase 3
0.6452 Remote Similarity NPD6060 Clinical (unspecified phase)
0.6452 Remote Similarity NPD8356 Approved
0.6447 Remote Similarity NPD6853 Approved
0.6447 Remote Similarity NPD6851 Approved
0.6445 Remote Similarity NPD4493 Discontinued
0.6439 Remote Similarity NPD6805 Discontinued
0.6436 Remote Similarity NPD2098 Approved
0.6435 Remote Similarity NPD3783 Clinical (unspecified phase)
0.6432 Remote Similarity NPD6395 Phase 2
0.6432 Remote Similarity NPD4201 Clinical (unspecified phase)
0.6432 Remote Similarity NPD6396 Clinical (unspecified phase)
0.6432 Remote Similarity NPD4897 Phase 2
0.6432 Remote Similarity NPD8025 Phase 2
0.6425 Remote Similarity NPD6645 Clinical (unspecified phase)
0.6422 Remote Similarity NPD7820 Phase 3
0.6418 Remote Similarity NPD3479 Discontinued
0.6411 Remote Similarity NPD6518 Discontinued
0.641 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6409 Remote Similarity NPD8430 Approved
0.6408 Remote Similarity NPD6238 Discontinued
0.64 Remote Similarity NPD6982 Phase 2
0.6398 Remote Similarity NPD3893 Discontinued
0.6398 Remote Similarity NPD7735 Clinical (unspecified phase)
0.6393 Remote Similarity NPD7821 Clinical (unspecified phase)
0.6392 Remote Similarity NPD5313 Approved
0.6392 Remote Similarity NPD3793 Phase 3
0.6392 Remote Similarity NPD6020 Phase 2
0.6392 Remote Similarity NPD5312 Approved
0.6387 Remote Similarity NPD5186 Approved
0.6387 Remote Similarity NPD5183 Approved
0.6387 Remote Similarity NPD4652 Approved
0.6387 Remote Similarity NPD5847 Phase 1
0.6384 Remote Similarity NPD3391 Approved
0.6381 Remote Similarity NPD8027 Approved
0.6381 Remote Similarity NPD6593 Clinical (unspecified phase)
0.6378 Remote Similarity NPD3684 Discontinued
0.6374 Remote Similarity NPD5942 Approved
0.6374 Remote Similarity NPD5941 Approved
0.6374 Remote Similarity NPD4432 Discontinued
0.6373 Remote Similarity NPD7324 Discontinued
0.6369 Remote Similarity NPD5024 Approved
0.6369 Remote Similarity NPD4430 Phase 2
0.6368 Remote Similarity NPD2162 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6283 Phase 2
0.6364 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7186 Phase 3
0.6364 Remote Similarity NPD6557 Phase 2
0.6359 Remote Similarity NPD5433 Clinical (unspecified phase)
0.6359 Remote Similarity NPD3437 Discontinued
0.6354 Remote Similarity NPD3975 Discontinued
0.6349 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6346 Remote Similarity NPD7205 Discontinued
0.6345 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6338 Remote Similarity NPD7178 Clinical (unspecified phase)
0.6333 Remote Similarity NPD7043 Discontinued
0.633 Remote Similarity NPD5967 Approved
0.633 Remote Similarity NPD2097 Approved
0.6329 Remote Similarity NPD3416 Discontinued
0.6324 Remote Similarity NPD4121 Phase 3
0.6324 Remote Similarity NPD4120 Approved
0.6324 Remote Similarity NPD3229 Phase 2
0.6318 Remote Similarity NPD7628 Phase 3
0.6318 Remote Similarity NPD5896 Clinical (unspecified phase)
0.6318 Remote Similarity NPD7630 Phase 3
0.6318 Remote Similarity NPD7617 Discontinued
0.6318 Remote Similarity NPD7629 Clinical (unspecified phase)
0.6313 Remote Similarity NPD7281 Phase 3
0.6313 Remote Similarity NPD7280 Phase 3
0.631 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6308 Remote Similarity NPD5521 Clinical (unspecified phase)
0.6308 Remote Similarity NPD3449 Discontinued
0.6305 Remote Similarity NPD5610 Approved
0.6303 Remote Similarity NPD2916 Discontinued
0.6302 Remote Similarity NPD1293 Approved
0.6301 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6293 Remote Similarity NPD5195 Discontinued
0.629 Remote Similarity NPD5743 Approved
0.629 Remote Similarity NPD5742 Approved
0.629 Remote Similarity NPD5741 Approved
0.6284 Remote Similarity NPD4682 Phase 2
0.6281 Remote Similarity NPD6021 Clinical (unspecified phase)
0.6279 Remote Similarity NPD4562 Clinical (unspecified phase)
0.6278 Remote Similarity NPD6199 Discontinued
0.6276 Remote Similarity NPD5900 Clinical (unspecified phase)
0.6273 Remote Similarity NPD3912 Discontinued
0.6268 Remote Similarity NPD6478 Clinical (unspecified phase)
0.6267 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6262 Remote Similarity NPD4668 Phase 2
0.6256 Remote Similarity NPD5507 Approved
0.6256 Remote Similarity NPD5506 Approved
0.6256 Remote Similarity NPD7805 Phase 3
0.625 Remote Similarity NPD7566 Clinical (unspecified phase)
0.625 Remote Similarity NPD2017 Approved
0.625 Remote Similarity NPD2888 Approved
0.625 Remote Similarity NPD2889 Approved
0.625 Remote Similarity NPD2890 Approved
0.625 Remote Similarity NPD6457 Approved
0.6245 Remote Similarity NPD7432 Phase 2
0.6244 Remote Similarity NPD5582 Discontinued
0.6243 Remote Similarity NPD7600 Phase 2
0.6239 Remote Similarity NPD2899 Discontinued
0.6238 Remote Similarity NPD5113 Approved
0.6238 Remote Similarity NPD5114 Approved
0.6238 Remote Similarity NPD5112 Approved
0.6237 Remote Similarity NPD6607 Clinical (unspecified phase)
0.6232 Remote Similarity NPD6874 Approved
0.6224 Remote Similarity NPD5600 Discontinued
0.6223 Remote Similarity NPD5715 Clinical (unspecified phase)
0.6222 Remote Similarity NPD4885 Approved
0.622 Remote Similarity NPD956 Clinical (unspecified phase)
0.6215 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6212 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6209 Remote Similarity NPD6260 Discontinued
0.6207 Remote Similarity NPD5994 Discontinued
0.6207 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6205 Remote Similarity NPD3423 Phase 2
0.6205 Remote Similarity NPD3422 Phase 3
0.6199 Remote Similarity NPD5566 Clinical (unspecified phase)
0.6197 Remote Similarity NPD3986 Discontinued
0.6195 Remote Similarity NPD6493 Phase 3
0.619 Remote Similarity NPD7599 Phase 2
0.619 Remote Similarity NPD7064 Clinical (unspecified phase)
0.6188 Remote Similarity NPD7412 Clinical (unspecified phase)
0.6176 Remote Similarity NPD6665 Discontinued
0.6175 Remote Similarity NPD8149 Discontinued
0.6175 Remote Similarity NPD160 Clinical (unspecified phase)
0.6173 Remote Similarity NPD2361 Approved
0.6173 Remote Similarity NPD4498 Clinical (unspecified phase)
0.6173 Remote Similarity NPD8022 Clinical (unspecified phase)
0.6168 Remote Similarity NPD4997 Clinical (unspecified phase)
0.6166 Remote Similarity NPD2680 Approved
0.6166 Remote Similarity NPD6379 Discontinued
0.6166 Remote Similarity NPD2681 Approved
0.6164 Remote Similarity NPD7203 Clinical (unspecified phase)
0.6162 Remote Similarity NPD6293 Clinical (unspecified phase)
0.6159 Remote Similarity NPD1000 Clinical (unspecified phase)
0.6158 Remote Similarity NPD4428 Discontinued
0.6158 Remote Similarity NPD5928 Phase 1
0.6158 Remote Similarity NPD5316 Approved
0.6158 Remote Similarity NPD3321 Discontinued
0.6154 Remote Similarity NPD5609 Approved
0.6154 Remote Similarity NPD5997 Discontinued
0.6154 Remote Similarity NPD5608 Approved
0.6149 Remote Similarity NPD5263 Approved
0.6143 Remote Similarity NPD3263 Phase 3

  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