Structure

Physi-Chem Properties

Molecular Weight:  576.13
Volume:  541.386
LogP:  2.758
LogD:  1.397
LogS:  -3.866
# Rotatable Bonds:  2
TPSA:  209.76
# H-Bond Aceptor:  12
# H-Bond Donor:  9
# Rings:  7
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.158
Synthetic Accessibility Score:  5.361
Fsp3:  0.2
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.773
MDCK Permeability:  5.377569777920144e-06
Pgp-inhibitor:  0.036
Pgp-substrate:  0.008
Human Intestinal Absorption (HIA):  0.428
20% Bioavailability (F20%):  0.88
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  91.0960464477539%
Volume Distribution (VD):  0.377
Pgp-substrate:  6.697143077850342%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.114
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.049
CYP2C9-inhibitor:  0.585
CYP2C9-substrate:  0.862
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.173
CYP3A4-inhibitor:  0.135
CYP3A4-substrate:  0.541

ADMET: Excretion

Clearance (CL):  10.356
Half-life (T1/2):  0.509

ADMET: Toxicity

hERG Blockers:  0.031
Human Hepatotoxicity (H-HT):  0.198
Drug-inuced Liver Injury (DILI):  0.875
AMES Toxicity:  0.487
Rat Oral Acute Toxicity:  0.617
Maximum Recommended Daily Dose:  0.553
Skin Sensitization:  0.955
Carcinogencity:  0.508
Eye Corrosion:  0.003
Eye Irritation:  0.9
Respiratory Toxicity:  0.044

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

  Natural Product: NPC322899

Natural Product ID:  NPC322899
Common Name*:   NSEWTSAADLNHNH-UAFVEXHRSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  NSEWTSAADLNHNH-UAFVEXHRSA-N
Standard InCHI:  InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26?,27-,29-,30+/m1/s1
SMILES:  Oc1cc(O)c2c(c1)O[C@@]1([C@@H](C2c2c(O1)cc(c1c2O[C@@H]([C@@H](C1)O)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL81646
PubChem CID:   44460468
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. 2007; 2008 DOI[10.1007/s11746-010-1589-7]
NPO3806 Garcinia morella Species Clusiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(00)90246-6]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. cotyledon n.a. PMID[11283027]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. seed n.a. PMID[12670184]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. seed n.a. PMID[21348467]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. PMID[22537213]
NPO25426 Arachis hypogaea Species n.a. n.a. Peanut Skins n.a. n.a. PMID[28231711]
NPO23044 Aesculus hippocastanum Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[3783160]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. Leaf n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. Oil n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. Seed n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO23044 Aesculus hippocastanum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3806 Garcinia morella Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO25426 Arachis hypogaea Species n.a. n.a. Oils n.a. Database[Phenol-Explorer]
NPO25426 Arachis hypogaea Species n.a. n.a. Seeds n.a. Database[Phenol-Explorer]
NPO23044 Aesculus hippocastanum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO3806 Garcinia morella Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3806 Garcinia morella Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23044 Aesculus hippocastanum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3806 Garcinia morella Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23044 Aesculus hippocastanum Species Sapindaceae 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
NPT316 Protein Family Protein kinase C (PKC) Homo sapiens IC50 > 100000.0 nM PMID[532768]

☑ 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 NPC322899 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 NPC134911
1.0 High Similarity NPC469944
1.0 High Similarity NPC226108
1.0 High Similarity NPC44192
1.0 High Similarity NPC272552
1.0 High Similarity NPC46283
0.9795 High Similarity NPC20050
0.9795 High Similarity NPC306267
0.9664 High Similarity NPC147743
0.9664 High Similarity NPC4809
0.9664 High Similarity NPC73517
0.9653 High Similarity NPC18185
0.9653 High Similarity NPC262911
0.9653 High Similarity NPC294558
0.9653 High Similarity NPC58190
0.9653 High Similarity NPC236202
0.9653 High Similarity NPC82917
0.9653 High Similarity NPC108811
0.9653 High Similarity NPC202742
0.9653 High Similarity NPC263940
0.9653 High Similarity NPC170103
0.9653 High Similarity NPC204770
0.9653 High Similarity NPC70409
0.96 High Similarity NPC106601
0.96 High Similarity NPC212614
0.96 High Similarity NPC185231
0.96 High Similarity NPC205613
0.96 High Similarity NPC159526
0.96 High Similarity NPC151474
0.96 High Similarity NPC86630
0.96 High Similarity NPC471404
0.9583 High Similarity NPC96576
0.9583 High Similarity NPC102280
0.9583 High Similarity NPC248053
0.9583 High Similarity NPC155564
0.9521 High Similarity NPC211561
0.9459 High Similarity NPC279406
0.9459 High Similarity NPC226809
0.9452 High Similarity NPC227516
0.9452 High Similarity NPC20757
0.9412 High Similarity NPC12326
0.9396 High Similarity NPC224161
0.9333 High Similarity NPC46335
0.9324 High Similarity NPC477612
0.931 High Similarity NPC28440
0.931 High Similarity NPC171932
0.9262 High Similarity NPC259707
0.9262 High Similarity NPC471403
0.9252 High Similarity NPC473480
0.9252 High Similarity NPC15538
0.9236 High Similarity NPC277331
0.9236 High Similarity NPC178054
0.9236 High Similarity NPC100482
0.92 High Similarity NPC59692
0.9189 High Similarity NPC280945
0.9178 High Similarity NPC138227
0.9178 High Similarity NPC469313
0.9178 High Similarity NPC168579
0.9178 High Similarity NPC76176
0.9156 High Similarity NPC1253
0.9156 High Similarity NPC100936
0.911 High Similarity NPC37793
0.9054 High Similarity NPC125755
0.9048 High Similarity NPC475492
0.9034 High Similarity NPC262189
0.9007 High Similarity NPC473621
0.8986 High Similarity NPC161700
0.8986 High Similarity NPC277867
0.8947 High Similarity NPC21902
0.8947 High Similarity NPC233467
0.894 High Similarity NPC472709
0.894 High Similarity NPC472710
0.8933 High Similarity NPC281549
0.8926 High Similarity NPC190714
0.8926 High Similarity NPC99515
0.8926 High Similarity NPC260397
0.8919 High Similarity NPC473108
0.8919 High Similarity NPC15659
0.8919 High Similarity NPC304894
0.8904 High Similarity NPC22317
0.8897 High Similarity NPC474390
0.8889 High Similarity NPC78809
0.8874 High Similarity NPC318373
0.8874 High Similarity NPC321657
0.8868 High Similarity NPC9309
0.8859 High Similarity NPC475096
0.8851 High Similarity NPC473044
0.8851 High Similarity NPC163508
0.8851 High Similarity NPC173203
0.8846 High Similarity NPC98083
0.8846 High Similarity NPC7543
0.8846 High Similarity NPC94220
0.8846 High Similarity NPC166456
0.8846 High Similarity NPC24339
0.8844 High Similarity NPC469661
0.8836 High Similarity NPC260741
0.8836 High Similarity NPC70682
0.8831 High Similarity NPC157333
0.8831 High Similarity NPC8712
0.8828 High Similarity NPC470802
0.8816 High Similarity NPC225815
0.8816 High Similarity NPC9933
0.8816 High Similarity NPC185955
0.8816 High Similarity NPC469706
0.8816 High Similarity NPC218041
0.8816 High Similarity NPC214326
0.8816 High Similarity NPC182368
0.8816 High Similarity NPC145979
0.8816 High Similarity NPC260781
0.8816 High Similarity NPC469707
0.8808 High Similarity NPC270751
0.8808 High Similarity NPC329836
0.8808 High Similarity NPC175976
0.8792 High Similarity NPC25292
0.8792 High Similarity NPC225445
0.8792 High Similarity NPC473045
0.8784 High Similarity NPC59841
0.8784 High Similarity NPC475084
0.8784 High Similarity NPC189115
0.8784 High Similarity NPC2613
0.8784 High Similarity NPC475891
0.8784 High Similarity NPC204347
0.8776 High Similarity NPC61783
0.8776 High Similarity NPC20520
0.8776 High Similarity NPC291101
0.8776 High Similarity NPC266197
0.8767 High Similarity NPC211549
0.8759 High Similarity NPC164787
0.8759 High Similarity NPC473413
0.8758 High Similarity NPC321972
0.8758 High Similarity NPC329343
0.8758 High Similarity NPC324517
0.875 High Similarity NPC476969
0.8742 High Similarity NPC31325
0.8742 High Similarity NPC474397
0.8742 High Similarity NPC114505
0.8742 High Similarity NPC224674
0.8742 High Similarity NPC227902
0.8742 High Similarity NPC101376
0.8742 High Similarity NPC275284
0.8742 High Similarity NPC213074
0.8742 High Similarity NPC193473
0.8742 High Similarity NPC15956
0.8742 High Similarity NPC39657
0.8734 High Similarity NPC155754
0.8734 High Similarity NPC109061
0.8734 High Similarity NPC124747
0.8733 High Similarity NPC181615
0.8733 High Similarity NPC23807
0.8725 High Similarity NPC81638
0.8725 High Similarity NPC252169
0.8725 High Similarity NPC472451
0.8725 High Similarity NPC116922
0.8718 High Similarity NPC165483
0.8716 High Similarity NPC87725
0.8716 High Similarity NPC35216
0.8716 High Similarity NPC471389
0.8716 High Similarity NPC263261
0.871 High Similarity NPC159922
0.8707 High Similarity NPC22517
0.8707 High Similarity NPC32630
0.8701 High Similarity NPC476391
0.8701 High Similarity NPC325860
0.8699 High Similarity NPC306441
0.8699 High Similarity NPC162659
0.8699 High Similarity NPC242028
0.8699 High Similarity NPC265433
0.8699 High Similarity NPC302701
0.8699 High Similarity NPC203230
0.8699 High Similarity NPC270456
0.8699 High Similarity NPC248727
0.8699 High Similarity NPC16435
0.8699 High Similarity NPC269091
0.8693 High Similarity NPC238140
0.869 High Similarity NPC66840
0.869 High Similarity NPC256307
0.8684 High Similarity NPC473876
0.8681 High Similarity NPC261619
0.8681 High Similarity NPC126029
0.8681 High Similarity NPC61477
0.8681 High Similarity NPC219876
0.8681 High Similarity NPC15658
0.8681 High Similarity NPC185604
0.8681 High Similarity NPC78770
0.8675 High Similarity NPC274454
0.8675 High Similarity NPC95652
0.8675 High Similarity NPC317053
0.8675 High Similarity NPC268515
0.8675 High Similarity NPC215678
0.8675 High Similarity NPC150714
0.8675 High Similarity NPC40222
0.8675 High Similarity NPC324492
0.8667 High Similarity NPC45257
0.8667 High Similarity NPC280092
0.8667 High Similarity NPC151704
0.8667 High Similarity NPC93323
0.8667 High Similarity NPC12641
0.8667 High Similarity NPC177597
0.8662 High Similarity NPC470827
0.8662 High Similarity NPC125495

  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 NPC322899 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
0.8681 High Similarity NPD1613 Approved
0.8681 High Similarity NPD1612 Clinical (unspecified phase)
0.8414 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8403 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD4908 Phase 1
0.8219 Intermediate Similarity NPD3027 Phase 3
0.8144 Intermediate Similarity NPD7074 Phase 3
0.8133 Intermediate Similarity NPD7228 Approved
0.8125 Intermediate Similarity NPD8455 Phase 2
0.8105 Intermediate Similarity NPD6674 Discontinued
0.8038 Intermediate Similarity NPD1653 Approved
0.8025 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD6166 Phase 2
0.8012 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD7054 Approved
0.7929 Intermediate Similarity NPD7472 Approved
0.7927 Intermediate Similarity NPD6234 Discontinued
0.7917 Intermediate Similarity NPD1610 Phase 2
0.7882 Intermediate Similarity NPD6797 Phase 2
0.784 Intermediate Similarity NPD37 Approved
0.7836 Intermediate Similarity NPD7251 Discontinued
0.7831 Intermediate Similarity NPD7199 Phase 2
0.7805 Intermediate Similarity NPD4965 Approved
0.7805 Intermediate Similarity NPD4966 Approved
0.7805 Intermediate Similarity NPD4967 Phase 2
0.7791 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD7266 Discontinued
0.7718 Intermediate Similarity NPD2861 Phase 2
0.7706 Intermediate Similarity NPD3818 Discontinued
0.7688 Intermediate Similarity NPD7808 Phase 3
0.7671 Intermediate Similarity NPD1091 Approved
0.7661 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD5844 Phase 1
0.7651 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD8312 Approved
0.7644 Intermediate Similarity NPD8313 Approved
0.7633 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD7240 Approved
0.7622 Intermediate Similarity NPD1934 Approved
0.7619 Intermediate Similarity NPD6959 Discontinued
0.7616 Intermediate Similarity NPD4625 Phase 3
0.7586 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD3787 Discontinued
0.7566 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6559 Discontinued
0.7517 Intermediate Similarity NPD1548 Phase 1
0.75 Intermediate Similarity NPD4380 Phase 2
0.7468 Intermediate Similarity NPD4060 Phase 1
0.745 Intermediate Similarity NPD4749 Approved
0.7436 Intermediate Similarity NPD7097 Phase 1
0.7425 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD5124 Phase 1
0.7401 Intermediate Similarity NPD8053 Approved
0.7401 Intermediate Similarity NPD8054 Approved
0.7391 Intermediate Similarity NPD5058 Phase 3
0.7365 Intermediate Similarity NPD1465 Phase 2
0.7353 Intermediate Similarity NPD5494 Approved
0.7346 Intermediate Similarity NPD7213 Phase 3
0.7346 Intermediate Similarity NPD7212 Phase 2
0.7333 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7680 Approved
0.7301 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD7447 Phase 1
0.7299 Intermediate Similarity NPD3751 Discontinued
0.7297 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD7549 Discontinued
0.7283 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7768 Phase 2
0.7267 Intermediate Similarity NPD6232 Discontinued
0.7263 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD2801 Approved
0.7255 Intermediate Similarity NPD3018 Phase 2
0.7244 Intermediate Similarity NPD3620 Phase 2
0.7244 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7473 Discontinued
0.7239 Intermediate Similarity NPD1511 Approved
0.7235 Intermediate Similarity NPD7075 Discontinued
0.7235 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD4536 Approved
0.7215 Intermediate Similarity NPD4538 Approved
0.7171 Intermediate Similarity NPD8651 Approved
0.717 Intermediate Similarity NPD5588 Approved
0.717 Intermediate Similarity NPD5960 Phase 3
0.7152 Intermediate Similarity NPD1512 Approved
0.7143 Intermediate Similarity NPD7411 Suspended
0.7118 Intermediate Similarity NPD3817 Phase 2
0.7105 Intermediate Similarity NPD2983 Phase 2
0.7105 Intermediate Similarity NPD2982 Phase 2
0.7099 Intermediate Similarity NPD1652 Phase 2
0.7086 Intermediate Similarity NPD3705 Approved
0.7081 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD3882 Suspended
0.7065 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD8156 Discontinued
0.7059 Intermediate Similarity NPD7819 Suspended
0.7059 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD5283 Phase 1
0.7041 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD2981 Phase 2
0.7033 Intermediate Similarity NPD4663 Approved
0.703 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD5402 Approved
0.7012 Intermediate Similarity NPD6190 Approved
0.7011 Intermediate Similarity NPD8127 Discontinued
0.7006 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6798 Discontinued
0.7006 Intermediate Similarity NPD8099 Discontinued
0.7006 Intermediate Similarity NPD8252 Approved
0.7006 Intermediate Similarity NPD8251 Approved
0.7006 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6801 Discontinued
0.6993 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6988 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6988 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5735 Approved
0.6975 Remote Similarity NPD5762 Approved
0.6975 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6975 Remote Similarity NPD5763 Approved
0.6975 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6971 Remote Similarity NPD7229 Phase 3
0.6961 Remote Similarity NPD4578 Approved
0.6961 Remote Similarity NPD4577 Approved
0.6959 Remote Similarity NPD7157 Approved
0.6959 Remote Similarity NPD8151 Discontinued
0.6957 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6954 Remote Similarity NPD5126 Approved
0.6954 Remote Similarity NPD5846 Approved
0.6954 Remote Similarity NPD5125 Phase 3
0.6954 Remote Similarity NPD6516 Phase 2
0.6951 Remote Similarity NPD3892 Phase 2
0.6951 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6951 Remote Similarity NPD3750 Approved
0.6951 Remote Similarity NPD7466 Approved
0.6944 Remote Similarity NPD7685 Pre-registration
0.6933 Remote Similarity NPD1549 Phase 2
0.6928 Remote Similarity NPD7041 Phase 2
0.6928 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6918 Remote Similarity NPD228 Approved
0.6914 Remote Similarity NPD6100 Approved
0.6914 Remote Similarity NPD6099 Approved
0.6905 Remote Similarity NPD5403 Approved
0.6902 Remote Similarity NPD7906 Approved
0.6897 Remote Similarity NPD3021 Approved
0.6897 Remote Similarity NPD3022 Approved
0.6893 Remote Similarity NPD2489 Approved
0.6893 Remote Similarity NPD27 Approved
0.689 Remote Similarity NPD5177 Phase 3
0.6888 Remote Similarity NPD7783 Phase 2
0.6888 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6887 Remote Similarity NPD1357 Approved
0.6886 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3051 Approved
0.6875 Remote Similarity NPD6355 Discontinued
0.6871 Remote Similarity NPD7843 Approved
0.6868 Remote Similarity NPD7311 Approved
0.6868 Remote Similarity NPD7310 Approved
0.6868 Remote Similarity NPD7312 Approved
0.6868 Remote Similarity NPD7313 Approved
0.6863 Remote Similarity NPD422 Phase 1
0.6859 Remote Similarity NPD6584 Phase 3
0.6855 Remote Similarity NPD6233 Phase 2
0.6852 Remote Similarity NPD4108 Discontinued
0.6848 Remote Similarity NPD6331 Phase 2
0.6846 Remote Similarity NPD6671 Approved
0.6836 Remote Similarity NPD2970 Approved
0.6836 Remote Similarity NPD2969 Approved
0.6835 Remote Similarity NPD7095 Approved
0.6831 Remote Similarity NPD7309 Approved
0.6829 Remote Similarity NPD2424 Discontinued
0.6829 Remote Similarity NPD7037 Approved
0.6828 Remote Similarity NPD2684 Approved
0.6824 Remote Similarity NPD7458 Discontinued
0.6821 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6813 Remote Similarity NPD4140 Approved
0.6813 Remote Similarity NPD1558 Phase 1
0.6811 Remote Similarity NPD6841 Approved
0.6811 Remote Similarity NPD6843 Phase 3
0.6811 Remote Similarity NPD6842 Approved
0.6807 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6807 Remote Similarity NPD2677 Approved
0.6806 Remote Similarity NPD6779 Approved
0.6806 Remote Similarity NPD6776 Approved
0.6806 Remote Similarity NPD6782 Approved
0.6806 Remote Similarity NPD6781 Approved
0.6806 Remote Similarity NPD6780 Approved
0.6806 Remote Similarity NPD6778 Approved
0.6806 Remote Similarity NPD6777 Approved
0.679 Remote Similarity NPD7119 Phase 2
0.6788 Remote Similarity NPD7421 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