Structure

Physi-Chem Properties

Molecular Weight:  578.22
Volume:  572.227
LogP:  5.576
LogD:  3.003
LogS:  -4.933
# Rotatable Bonds:  5
TPSA:  136.3
# H-Bond Aceptor:  10
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.256
Synthetic Accessibility Score:  4.551
Fsp3:  0.375
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:  -5.918
MDCK Permeability:  1.559004158480093e-05
Pgp-inhibitor:  0.914
Pgp-substrate:  0.983
Human Intestinal Absorption (HIA):  0.655
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.806

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.005
Plasma Protein Binding (PPB):  67.46577453613281%
Volume Distribution (VD):  0.61
Pgp-substrate:  29.72852325439453%

ADMET: Metabolism

CYP1A2-inhibitor:  0.058
CYP1A2-substrate:  0.984
CYP2C19-inhibitor:  0.018
CYP2C19-substrate:  0.882
CYP2C9-inhibitor:  0.03
CYP2C9-substrate:  0.763
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.43
CYP3A4-inhibitor:  0.061
CYP3A4-substrate:  0.166

ADMET: Excretion

Clearance (CL):  6.838
Half-life (T1/2):  0.143

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.305
Drug-inuced Liver Injury (DILI):  0.918
AMES Toxicity:  0.349
Rat Oral Acute Toxicity:  0.106
Maximum Recommended Daily Dose:  0.397
Skin Sensitization:  0.263
Carcinogencity:  0.023
Eye Corrosion:  0.003
Eye Irritation:  0.074
Respiratory Toxicity:  0.482

Download Data

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

  Natural Product: NPC174251

Natural Product ID:  NPC174251
Common Name*:   Sid24841469
IUPAC Name:   (3S,4S)-5-[(3S,4S)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl]-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-4,10-diol
Synonyms:  
Standard InCHIKey:  AVAQRWVGWWNBIN-CUAUGLLKSA-N
Standard InCHI:  InChI=1S/C32H34O10/c1-13-29(33)27-19(11-41-13)31(35)23-17(7-15(37-3)9-21(23)39-5)25(27)26-18-8-16(38-4)10-22(40-6)24(18)32(36)20-12-42-14(2)30(34)28(20)26/h7-10,13-14,29-30,33-36H,11-12H2,1-6H3/t13-,14-,29+,30+/m0/s1
SMILES:  COc1cc(OC)c2c(c1)c(c1c(c2O)CO[C@H]([C@H]1O)C)c1c2[C@H](O)[C@H](C)OCc2c(c2c1cc(OC)cc2OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL399293
PubChem CID:   10257591
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001610] Arylnaphthalene lignans

*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
NPO32515 Cordyceps sp. Under-species n.a. n.a. n.a. n.a. n.a. PMID[17887724]
NPO32514 Cordyceps sp. Under-species n.a. n.a. n.a. n.a. n.a. PMID[17887724]

☑ 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
NPT47 Individual Protein ATP-dependent DNA helicase Q1 Homo sapiens Potency = 25118.9 nM PMID[516368]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 25118.9 nM PMID[516368]
NPT1038 Individual Protein Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 50118.7 nM PMID[516368]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 35481.3 nM PMID[516368]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 316.2 nM PMID[516368]
NPT3 Individual Protein Thioredoxin glutathione reductase Schistosoma mansoni Potency = 3548.1 nM PMID[516368]
NPT53 Individual Protein 4'-phosphopantetheinyl transferase ffp Bacillus subtilis Potency = 25118.9 nM PMID[516368]
NPT442 Individual Protein Ferritin light chain Equus caballus Potency = 50118.7 nM PMID[516368]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 1990.5 nM PMID[516368]
NPT57 Individual Protein Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens IC50 = 2507.45 nM PMID[516368]
NPT58 Individual Protein Bloom syndrome protein Homo sapiens Potency = 31622.8 nM PMID[516368]
NPT59 Individual Protein DNA polymerase beta Homo sapiens Potency = 35481.3 nM PMID[516368]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 50118.7 nM PMID[516368]
NPT443 Individual Protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 31622.8 nM PMID[516368]
NPT1039 Individual Protein Envelope glycoprotein gp160 Human immunodeficiency virus 1 IC50 = 10100.0 nM PMID[516368]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 44668.4 nM PMID[516368]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 50118.7 nM PMID[516368]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 8912.5 nM PMID[516368]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 39810.7 nM PMID[516368]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 28183.8 nM PMID[516368]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 3981.1 nM PMID[516368]
NPT1417 Individual Protein Transcriptional regulator ERG Homo sapiens Potency n.a. 35481.3 nM PMID[516368]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 7.3 nM PMID[516368]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 44668.4 nM PMID[516368]
NPT446 Individual Protein Rap guanine nucleotide exchange factor 3 Homo sapiens Potency n.a. 35481.3 nM PMID[516368]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 25118.9 nM PMID[516368]
NPT1040 Individual Protein Human immunodeficiency virus type 1 Tat protein Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1) IC50 n.a. 30829.0 nM PMID[516368]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Inhibition < 50.0 % PMID[516367]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 8100.0 nM PMID[516367]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 31622.8 nM PMID[516368]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 44668.4 nM PMID[516368]
NPT795 Individual Protein Zinc finger protein mex-5 Caenorhabditis elegans EC50 > 300000.0 nM PMID[516368]
NPT3937 Protein-Protein Interaction Voltage-gated N-type calcium channel alpha-1B subunit/Amyloid beta A4 precursor protein-binding family A member 1 Homo sapiens IC50 = 4270.0 nM PMID[516368]
NPT2 Others Unspecified EC50 > 110000.0 nM PMID[516368]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 17782.8 nM PMID[516368]
NPT864 Individual Protein Lethal(3)malignant brain tumor-like protein 1 Homo sapiens Potency = 25118.9 nM PMID[516368]
NPT797 Individual Protein Cytoplasmic zinc-finger protein Caenorhabditis elegans EC50 > 300000.0 nM PMID[516368]
NPT4214 Protein Complex SUMO-activating enzyme Homo sapiens IC50 = 17090.0 nM PMID[516368]
NPT3937 Protein-Protein Interaction Voltage-gated N-type calcium channel alpha-1B subunit/Amyloid beta A4 precursor protein-binding family A member 1 Homo sapiens IC50 = 20300.0 nM PMID[516368]
NPT4214 Protein Complex SUMO-activating enzyme Homo sapiens IC50 = 6030.0 nM PMID[516368]
NPT21702 PROTEIN-PROTEIN INTERACTION Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 125892.5 nM PMID[516368]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 11689.1 nM PMID[516368]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 56234.1 nM PMID[516368]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 39810.7 nM PMID[516368]
NPT9 Individual Protein DNA polymerase eta Homo sapiens Potency n.a. 19952.6 nM PMID[516368]
NPT698 Individual Protein Regulator of G-protein signaling 4 Homo sapiens Potency n.a. 39810.7 nM PMID[516368]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[516368]
NPT821 Individual Protein Werner syndrome ATP-dependent helicase Homo sapiens Potency n.a. 50118.7 nM PMID[516368]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 50118.7 nM PMID[516368]
NPT920 Individual Protein Alpha-synuclein Homo sapiens Potency n.a. 5623.4 nM PMID[516368]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens Potency n.a. 21192.3 nM PMID[516368]
NPT2 Others Unspecified IC50 n.a. 4610.0 nM PMID[516368]

☑ 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 NPC174251 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 NPC153182
0.9928 High Similarity NPC274454
0.9928 High Similarity NPC215678
0.9514 High Similarity NPC162976
0.9514 High Similarity NPC118000
0.9514 High Similarity NPC205501
0.922 High Similarity NPC273623
0.9178 High Similarity NPC321657
0.9178 High Similarity NPC318373
0.9078 High Similarity NPC472646
0.9078 High Similarity NPC71465
0.9041 High Similarity NPC262297
0.9021 High Similarity NPC277331
0.9021 High Similarity NPC100482
0.9007 High Similarity NPC472649
0.9007 High Similarity NPC170328
0.9007 High Similarity NPC472648
0.9007 High Similarity NPC206525
0.9007 High Similarity NPC472647
0.9007 High Similarity NPC191462
0.9007 High Similarity NPC133463
0.8986 High Similarity NPC477612
0.8973 High Similarity NPC96576
0.8973 High Similarity NPC126291
0.8966 High Similarity NPC475492
0.8936 High Similarity NPC37410
0.8936 High Similarity NPC258780
0.8919 High Similarity NPC211561
0.8912 High Similarity NPC170103
0.8912 High Similarity NPC236202
0.8912 High Similarity NPC263940
0.8912 High Similarity NPC82917
0.8912 High Similarity NPC108811
0.8912 High Similarity NPC70409
0.8912 High Similarity NPC58190
0.8912 High Similarity NPC202742
0.8912 High Similarity NPC18185
0.8912 High Similarity NPC262911
0.8912 High Similarity NPC294558
0.8912 High Similarity NPC204770
0.8867 High Similarity NPC279406
0.8867 High Similarity NPC226809
0.8828 High Similarity NPC472088
0.8828 High Similarity NPC186033
0.8828 High Similarity NPC472087
0.8828 High Similarity NPC183709
0.8811 High Similarity NPC470308
0.8811 High Similarity NPC470307
0.8808 High Similarity NPC224161
0.8786 High Similarity NPC282508
0.8784 High Similarity NPC474397
0.8759 High Similarity NPC472089
0.875 High Similarity NPC46335
0.8742 High Similarity NPC59692
0.8742 High Similarity NPC325860
0.8742 High Similarity NPC476391
0.8742 High Similarity NPC233467
0.8741 High Similarity NPC471522
0.8725 High Similarity NPC20757
0.8725 High Similarity NPC281549
0.8725 High Similarity NPC227516
0.8716 High Similarity NPC14468
0.8716 High Similarity NPC102280
0.8716 High Similarity NPC248053
0.8716 High Similarity NPC155564
0.8714 High Similarity NPC254000
0.8707 High Similarity NPC171932
0.8707 High Similarity NPC28440
0.869 High Similarity NPC472090
0.869 High Similarity NPC472092
0.869 High Similarity NPC308768
0.869 High Similarity NPC472091
0.869 High Similarity NPC12668
0.8681 High Similarity NPC22902
0.8681 High Similarity NPC266006
0.8675 High Similarity NPC302915
0.8675 High Similarity NPC259707
0.8675 High Similarity NPC471403
0.8667 High Similarity NPC295573
0.8667 High Similarity NPC470208
0.8667 High Similarity NPC476969
0.8652 High Similarity NPC471517
0.8652 High Similarity NPC473309
0.863 High Similarity NPC265075
0.8627 High Similarity NPC157333
0.8621 High Similarity NPC218131
0.8621 High Similarity NPC243759
0.8621 High Similarity NPC105847
0.8621 High Similarity NPC275061
0.8621 High Similarity NPC114171
0.8621 High Similarity NPC220344
0.8621 High Similarity NPC230124
0.8621 High Similarity NPC6300
0.8621 High Similarity NPC132804
0.8621 High Similarity NPC243996
0.8618 High Similarity NPC473018
0.8618 High Similarity NPC44192
0.8618 High Similarity NPC469944
0.8618 High Similarity NPC120633
0.8618 High Similarity NPC226108
0.8618 High Similarity NPC272552
0.8618 High Similarity NPC157783
0.8618 High Similarity NPC46283
0.8618 High Similarity NPC322899
0.8618 High Similarity NPC134911
0.8611 High Similarity NPC472800
0.8609 High Similarity NPC225815
0.8609 High Similarity NPC145979
0.8609 High Similarity NPC469707
0.8609 High Similarity NPC158784
0.8609 High Similarity NPC214326
0.8609 High Similarity NPC260781
0.8609 High Similarity NPC218041
0.8609 High Similarity NPC469706
0.8609 High Similarity NPC182368
0.8609 High Similarity NPC9933
0.8609 High Similarity NPC185955
0.8601 High Similarity NPC473107
0.8601 High Similarity NPC476615
0.8601 High Similarity NPC476617
0.8601 High Similarity NPC476616
0.86 High Similarity NPC473876
0.8591 High Similarity NPC233980
0.8581 High Similarity NPC4809
0.8581 High Similarity NPC473845
0.8581 High Similarity NPC73517
0.8581 High Similarity NPC147743
0.8581 High Similarity NPC473108
0.8571 High Similarity NPC471064
0.8571 High Similarity NPC175838
0.8571 High Similarity NPC311293
0.8571 High Similarity NPC215300
0.8571 High Similarity NPC148366
0.8571 High Similarity NPC38017
0.8562 High Similarity NPC306267
0.8562 High Similarity NPC20050
0.8561 High Similarity NPC82299
0.8553 High Similarity NPC2745
0.8552 High Similarity NPC151656
0.8552 High Similarity NPC266453
0.8552 High Similarity NPC242715
0.8552 High Similarity NPC230919
0.8552 High Similarity NPC56329
0.8552 High Similarity NPC200935
0.8533 High Similarity NPC6702
0.8533 High Similarity NPC112819
0.8533 High Similarity NPC133209
0.8533 High Similarity NPC111134
0.8526 High Similarity NPC185231
0.8526 High Similarity NPC151474
0.8526 High Similarity NPC205613
0.8526 High Similarity NPC212614
0.8526 High Similarity NPC106601
0.8526 High Similarity NPC86630
0.8526 High Similarity NPC471404
0.8526 High Similarity NPC159526
0.8523 High Similarity NPC181615
0.8521 High Similarity NPC103799
0.8521 High Similarity NPC160623
0.8514 High Similarity NPC469630
0.8511 High Similarity NPC471519
0.8511 High Similarity NPC471518
0.8503 High Similarity NPC178054
0.85 High Similarity NPC53781
0.85 High Similarity NPC473221
0.8497 Intermediate Similarity NPC21902
0.8493 Intermediate Similarity NPC184613
0.8493 Intermediate Similarity NPC475836
0.8493 Intermediate Similarity NPC32630
0.8489 Intermediate Similarity NPC293801
0.8487 Intermediate Similarity NPC218801
0.8487 Intermediate Similarity NPC195561
0.8483 Intermediate Similarity NPC30632
0.8483 Intermediate Similarity NPC202846
0.8483 Intermediate Similarity NPC470802
0.8483 Intermediate Similarity NPC143139
0.8483 Intermediate Similarity NPC141717
0.8477 Intermediate Similarity NPC212142
0.8472 Intermediate Similarity NPC184269
0.8472 Intermediate Similarity NPC125649
0.8471 Intermediate Similarity NPC100936
0.8471 Intermediate Similarity NPC1253
0.8467 Intermediate Similarity NPC95652
0.8467 Intermediate Similarity NPC260397
0.8467 Intermediate Similarity NPC471608
0.8467 Intermediate Similarity NPC150714
0.8456 Intermediate Similarity NPC304894
0.8456 Intermediate Similarity NPC15659
0.8456 Intermediate Similarity NPC50250
0.8452 Intermediate Similarity NPC202104
0.8435 Intermediate Similarity NPC22317
0.8435 Intermediate Similarity NPC295719
0.8435 Intermediate Similarity NPC73505
0.8435 Intermediate Similarity NPC165026
0.8435 Intermediate Similarity NPC174787
0.8435 Intermediate Similarity NPC182509
0.8435 Intermediate Similarity NPC262189
0.8435 Intermediate Similarity NPC213607
0.8435 Intermediate Similarity NPC34431
0.8431 Intermediate Similarity NPC329343

  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 NPC174251 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
0.8322 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8302 Intermediate Similarity NPD6959 Discontinued
0.8252 Intermediate Similarity NPD4625 Phase 3
0.8182 Intermediate Similarity NPD4908 Phase 1
0.8082 Intermediate Similarity NPD1613 Approved
0.8082 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD3027 Phase 3
0.7945 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD7228 Approved
0.7925 Intermediate Similarity NPD8455 Phase 2
0.7895 Intermediate Similarity NPD6674 Discontinued
0.7862 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7808 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD5844 Phase 1
0.7708 Intermediate Similarity NPD4749 Approved
0.7706 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1610 Phase 2
0.7661 Intermediate Similarity NPD8312 Approved
0.7661 Intermediate Similarity NPD8313 Approved
0.764 Intermediate Similarity NPD37 Approved
0.7625 Intermediate Similarity NPD4380 Phase 2
0.7622 Intermediate Similarity NPD6234 Discontinued
0.7607 Intermediate Similarity NPD4967 Phase 2
0.7607 Intermediate Similarity NPD4965 Approved
0.7607 Intermediate Similarity NPD4966 Approved
0.7605 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD6166 Phase 2
0.759 Intermediate Similarity NPD6232 Discontinued
0.7588 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD7473 Discontinued
0.7546 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD7240 Approved
0.75 Intermediate Similarity NPD2861 Phase 2
0.75 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7768 Phase 2
0.7483 Intermediate Similarity NPD4060 Phase 1
0.7471 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD7390 Discontinued
0.7458 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD6559 Discontinued
0.7421 Intermediate Similarity NPD7447 Phase 1
0.7419 Intermediate Similarity NPD8151 Discontinued
0.7415 Intermediate Similarity NPD8651 Approved
0.7414 Intermediate Similarity NPD8053 Approved
0.7414 Intermediate Similarity NPD8054 Approved
0.7413 Intermediate Similarity NPD1548 Phase 1
0.7396 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD7819 Suspended
0.7378 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD3620 Phase 2
0.7368 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD7212 Phase 2
0.7358 Intermediate Similarity NPD7041 Phase 2
0.7358 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD7213 Phase 3
0.7355 Intermediate Similarity NPD6100 Approved
0.7355 Intermediate Similarity NPD6099 Approved
0.7347 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7074 Phase 3
0.732 Intermediate Similarity NPD5735 Approved
0.7312 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6696 Suspended
0.7278 Intermediate Similarity NPD3787 Discontinued
0.7267 Intermediate Similarity NPD7054 Approved
0.7246 Intermediate Similarity NPD7075 Discontinued
0.7239 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD4536 Approved
0.7226 Intermediate Similarity NPD4538 Approved
0.7226 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD7472 Approved
0.7219 Intermediate Similarity NPD7199 Phase 2
0.7212 Intermediate Similarity NPD1934 Approved
0.7208 Intermediate Similarity NPD5124 Phase 1
0.7208 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7808 Phase 3
0.7197 Intermediate Similarity NPD5762 Approved
0.7197 Intermediate Similarity NPD7266 Discontinued
0.7197 Intermediate Similarity NPD5763 Approved
0.7192 Intermediate Similarity NPD5125 Phase 3
0.7192 Intermediate Similarity NPD5126 Approved
0.7183 Intermediate Similarity NPD4869 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7229 Phase 3
0.717 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD1465 Phase 2
0.7168 Intermediate Similarity NPD8156 Discontinued
0.7161 Intermediate Similarity NPD4097 Suspended
0.7152 Intermediate Similarity NPD3018 Phase 2
0.7151 Intermediate Similarity NPD7680 Approved
0.7143 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7251 Discontinued
0.7133 Intermediate Similarity NPD3094 Phase 2
0.712 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD7097 Phase 1
0.7113 Intermediate Similarity NPD7843 Approved
0.711 Intermediate Similarity NPD8252 Approved
0.711 Intermediate Similarity NPD8251 Approved
0.711 Intermediate Similarity NPD8099 Discontinued
0.7099 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD2532 Approved
0.7099 Intermediate Similarity NPD2533 Approved
0.7099 Intermediate Similarity NPD2534 Approved
0.7099 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD1091 Approved
0.7086 Intermediate Similarity NPD6797 Phase 2
0.7083 Intermediate Similarity NPD7157 Approved
0.7075 Intermediate Similarity NPD4626 Approved
0.7073 Intermediate Similarity NPD1653 Approved
0.707 Intermediate Similarity NPD5960 Phase 3
0.707 Intermediate Similarity NPD5588 Approved
0.7068 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD7783 Phase 2
0.7066 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD7003 Approved
0.7059 Intermediate Similarity NPD7698 Approved
0.7059 Intermediate Similarity NPD7696 Phase 3
0.7059 Intermediate Similarity NPD7697 Approved
0.7048 Intermediate Similarity NPD7411 Suspended
0.7035 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD7340 Approved
0.7025 Intermediate Similarity NPD2438 Suspended
0.7021 Intermediate Similarity NPD7871 Phase 2
0.7021 Intermediate Similarity NPD4750 Phase 3
0.7021 Intermediate Similarity NPD7870 Phase 2
0.7013 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD3751 Discontinued
0.7007 Intermediate Similarity NPD5691 Approved
0.7005 Intermediate Similarity NPD6823 Phase 2
0.7 Intermediate Similarity NPD7906 Approved
0.7 Intermediate Similarity NPD7701 Phase 2
0.7 Intermediate Similarity NPD5327 Phase 3
0.7 Intermediate Similarity NPD1652 Phase 2
0.7 Intermediate Similarity NPD2982 Phase 2
0.7 Intermediate Similarity NPD2342 Discontinued
0.7 Intermediate Similarity NPD2983 Phase 2
0.6994 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6994 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6993 Remote Similarity NPD7635 Approved
0.6989 Remote Similarity NPD6779 Approved
0.6989 Remote Similarity NPD6777 Approved
0.6989 Remote Similarity NPD6781 Approved
0.6989 Remote Similarity NPD6776 Approved
0.6989 Remote Similarity NPD6782 Approved
0.6989 Remote Similarity NPD6780 Approved
0.6989 Remote Similarity NPD6778 Approved
0.6983 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6982 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6981 Remote Similarity NPD2029 Clinical (unspecified phase)
0.698 Remote Similarity NPD3092 Approved
0.6975 Remote Similarity NPD5058 Phase 3
0.6968 Remote Similarity NPD7435 Discontinued
0.6966 Remote Similarity NPD6671 Approved
0.6964 Remote Similarity NPD5929 Approved
0.6959 Remote Similarity NPD5494 Approved
0.6959 Remote Similarity NPD4666 Phase 3
0.6957 Remote Similarity NPD3892 Phase 2
0.6957 Remote Similarity NPD7466 Approved
0.6957 Remote Similarity NPD3750 Approved
0.6946 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6944 Remote Similarity NPD1398 Phase 1
0.6944 Remote Similarity NPD8150 Discontinued
0.6941 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6937 Remote Similarity NPD7037 Approved
0.6933 Remote Similarity NPD2981 Phase 2
0.6928 Remote Similarity NPD4005 Discontinued
0.6923 Remote Similarity NPD2238 Phase 2
0.6923 Remote Similarity NPD4140 Approved
0.6919 Remote Similarity NPD8127 Discontinued
0.6918 Remote Similarity NPD5406 Approved
0.6918 Remote Similarity NPD5408 Approved
0.6918 Remote Similarity NPD5405 Approved
0.6918 Remote Similarity NPD5404 Approved
0.6914 Remote Similarity NPD2677 Approved
0.6905 Remote Similarity NPD6801 Discontinued
0.6903 Remote Similarity NPD6798 Discontinued
0.6903 Remote Similarity NPD7985 Registered
0.6901 Remote Similarity NPD5709 Phase 3
0.6892 Remote Similarity NPD1651 Approved
0.6882 Remote Similarity NPD7700 Phase 2
0.6882 Remote Similarity NPD7699 Phase 2
0.6875 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6867 Remote Similarity NPD3705 Approved
0.6867 Remote Similarity NPD1611 Approved
0.6864 Remote Similarity NPD2801 Approved
0.6863 Remote Similarity NPD6584 Phase 3
0.686 Remote Similarity NPD6746 Phase 2
0.6855 Remote Similarity NPD4108 Discontinued
0.6852 Remote Similarity NPD4628 Phase 3
0.6852 Remote Similarity NPD7982 Clinical (unspecified phase)
0.6846 Remote Similarity NPD5846 Approved
0.6846 Remote Similarity NPD6516 Phase 2
0.6842 Remote Similarity NPD3749 Approved
0.6842 Remote Similarity NPD1283 Approved
0.6839 Remote Similarity NPD7875 Clinical (unspecified phase)

  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