NPASS Compound

Structure

NPC98624 OpenBabel07101719122D 46 50 0 0 1 0 0 0 0 0999 V2000 11.1303 -1.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1599 3.5113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6958 3.5113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6958 2.5113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6303 -2.3034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1303 -3.1694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5618 4.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5618 1.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4278 2.5113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1303 -1.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9666 -1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6939 -2.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7902 -1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5618 2.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1303 -1.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4278 0.5113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6357 -0.4668 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1303 -3.1694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6303 -2.3034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2938 2.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 -2.2804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9811 -3.2315 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9592 -3.4394 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6283 -2.6962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6303 -0.5713 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2938 1.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3193 -1.7452 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5618 5.0113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7847 -1.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6303 -4.0354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3119 -3.9746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2682 -4.3905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6065 -2.9042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -2.5772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1970 -0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6303 -2.3034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1599 2.5113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9885 -1.0020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -1.5373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0370 0.3422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 40 1 0 0 0 0 2 41 1 0 0 0 0 3 4 1 0 0 0 0 3 7 1 0 0 0 0 4 15 1 0 0 0 0 5 6 2 0 0 0 0 5 16 1 0 0 0 0 6 19 1 0 0 0 0 7 32 1 0 0 0 0 8 15 2 0 0 0 0 8 17 1 0 0 0 0 9 15 1 0 0 0 0 9 21 2 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 42 1 0 0 0 0 12 43 1 0 0 0 0 13 31 1 0 0 0 0 13 33 1 0 0 0 0 14 31 1 0 0 0 0 14 44 1 0 0 0 0 17 18 1 0 0 0 0 17 27 2 0 0 0 0 18 11 1 1 0 0 0 18 26 1 0 0 0 0 19 20 2 0 0 0 0 19 34 1 0 0 0 0 20 40 1 0 0 0 0 21 27 1 0 0 0 0 21 41 1 0 0 0 0 22 12 1 1 0 0 0 22 23 1 0 0 0 0 22 45 1 0 0 0 0 23 24 1 0 0 0 0 23 35 1 6 0 0 0 24 25 1 0 0 0 0 24 36 1 1 0 0 0 25 29 1 0 0 0 0 25 37 1 6 0 0 0 26 16 1 6 0 0 0 26 46 1 0 0 0 0 27 46 1 0 0 0 0 28 30 1 0 0 0 0 28 31 1 6 0 0 0 28 38 1 0 0 0 0 29 42 1 1 0 0 0 29 45 1 0 0 0 0 30 43 1 1 0 0 0 30 44 1 0 0 0 0 31 39 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.25
Volume:	617.984
LogP:	-0.012
LogD:	-0.101
LogS:	-2.452
# Rotatable Bonds:	13
TPSA:	226.45
# H-Bond Aceptor:	15
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.127
Synthetic Accessibility Score:	5.047
Fsp3:	0.613
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.385
MDCK Permeability:	1.7695421774988063e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.943
20% Bioavailability (F20%):	0.404
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	53.841514587402344%
Volume Distribution (VD):	0.292
Pgp-substrate:	21.327571868896484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.356
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.382

ADMET: Excretion

Clearance (CL):	1.504
Half-life (T1/2):	0.626

ADMET: Toxicity

hERG Blockers:	0.474
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.583
AMES Toxicity:	0.403
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.945
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.047

Download Data

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

Natural Product: NPC98624

Natural Product ID:	NPC98624
*Common Name:**	(7S,8R)-Dihydrodehydrodiconiferyl Alcohol 9-O-Beta-D-Apiofuranosyl-(1->6)-O-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	LSDNKHHWXXGUFE-PSZXWCQTSA-N
Standard InCHI:	InChI=1S/C31H42O15/c1-40-20-10-16(5-6-19(20)34)26-18(17-8-15(4-3-7-32)9-21(41-2)27(17)46-26)11-42-29-25(37)24(36)23(35)22(45-29)12-43-30-28(38)31(39,13-33)14-44-30/h5-6,8-10,18,22-26,28-30,32-39H,3-4,7,11-14H2,1-2H3/t18-,22+,23+,24-,25+,26+,28-,29+,30+,31+/m0/s1
SMILES:	OCCCc1cc(OC)c2c(c1)[C@H](CO[C@@H]1O[C@H](CO[C@@H]3OC[C@]([C@H]3O)(O)CO)[C@H]([C@@H]([C@H]1O)O)O)[C@H](O2)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509402
PubChem CID:	24878740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO33006	neoalsomitra integrifoliola	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18396904]

☑ 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

Activity Type	# Activity
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	29.2	%	PMID[569787]

☑ 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 NPC98624 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	441
0.1-0.2	1368
0.2-0.3	3362
0.3-0.4	8156
0.4-0.5	9984
0.5-0.6	5726
0.6-0.7	8533
0.7-0.8	4063
0.8-0.85	754
0.85-0.9	242
0.9-0.95	67
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC31325
0.9789	High Similarity	NPC275284
0.9789	High Similarity	NPC224674
0.9789	High Similarity	NPC193473
0.9789	High Similarity	NPC114505
0.9789	High Similarity	NPC213074
0.9789	High Similarity	NPC15956
0.9718	High Similarity	NPC112861
0.9648	High Similarity	NPC22150
0.9648	High Similarity	NPC38041
0.9648	High Similarity	NPC279298
0.9648	High Similarity	NPC476301
0.9648	High Similarity	NPC43508
0.9648	High Similarity	NPC18979
0.9577	High Similarity	NPC84181
0.9577	High Similarity	NPC129417
0.9577	High Similarity	NPC79429
0.9577	High Similarity	NPC471667
0.9577	High Similarity	NPC217635
0.9577	High Similarity	NPC470235
0.9577	High Similarity	NPC283995
0.9507	High Similarity	NPC477898
0.9507	High Similarity	NPC185307
0.9507	High Similarity	NPC470950
0.9507	High Similarity	NPC46092
0.9452	High Similarity	NPC472710
0.9452	High Similarity	NPC475224
0.9452	High Similarity	NPC472709
0.9437	High Similarity	NPC253878
0.9437	High Similarity	NPC476356
0.9437	High Similarity	NPC246947
0.9384	High Similarity	NPC51328
0.9384	High Similarity	NPC55158
0.9384	High Similarity	NPC286235
0.9375	High Similarity	NPC469586
0.9366	High Similarity	NPC472711
0.9366	High Similarity	NPC471414
0.9315	High Similarity	NPC270751
0.9315	High Similarity	NPC248132
0.9315	High Similarity	NPC130449
0.9252	High Similarity	NPC44452
0.9247	High Similarity	NPC39657
0.9225	High Similarity	NPC156376
0.9205	High Similarity	NPC228357
0.92	High Similarity	NPC159922
0.9178	High Similarity	NPC276753
0.9178	High Similarity	NPC205796
0.9167	High Similarity	NPC302506
0.9155	High Similarity	NPC138738
0.9155	High Similarity	NPC470413
0.911	High Similarity	NPC180953
0.911	High Similarity	NPC475096
0.9097	High Similarity	NPC471908
0.9085	High Similarity	NPC478269
0.9085	High Similarity	NPC156502
0.9085	High Similarity	NPC177160
0.9085	High Similarity	NPC52277
0.9085	High Similarity	NPC54743
0.9085	High Similarity	NPC263367
0.9085	High Similarity	NPC29799
0.9085	High Similarity	NPC209985
0.9085	High Similarity	NPC477939
0.9085	High Similarity	NPC177035
0.9085	High Similarity	NPC199459
0.9085	High Similarity	NPC10737
0.9067	High Similarity	NPC302610
0.9054	High Similarity	NPC226153
0.9054	High Similarity	NPC304048
0.9054	High Similarity	NPC166584
0.9054	High Similarity	NPC71726
0.9054	High Similarity	NPC301961
0.9048	High Similarity	NPC190714
0.9048	High Similarity	NPC99515
0.9041	High Similarity	NPC472712
0.9041	High Similarity	NPC187774
0.9041	High Similarity	NPC472713
0.9041	High Similarity	NPC473046
0.9041	High Similarity	NPC471063
0.9041	High Similarity	NPC164183
0.9041	High Similarity	NPC118385
0.9041	High Similarity	NPC179521
0.9028	High Similarity	NPC106944
0.9021	High Similarity	NPC304152
0.9014	High Similarity	NPC135777
0.9014	High Similarity	NPC142547
0.9014	High Similarity	NPC184938
0.9014	High Similarity	NPC101624
0.8986	High Similarity	NPC227902
0.898	High Similarity	NPC286245
0.898	High Similarity	NPC272619
0.8973	High Similarity	NPC278961
0.8973	High Similarity	NPC81638
0.8973	High Similarity	NPC265154
0.8973	High Similarity	NPC113680
0.8968	High Similarity	NPC478267
0.8958	High Similarity	NPC193666
0.8958	High Similarity	NPC123526
0.8958	High Similarity	NPC88640
0.8954	High Similarity	NPC11411
0.8944	High Similarity	NPC470881
0.8944	High Similarity	NPC170779
0.8944	High Similarity	NPC187616
0.8944	High Similarity	NPC90083
0.8944	High Similarity	NPC187194
0.8944	High Similarity	NPC193026
0.8944	High Similarity	NPC476411
0.8944	High Similarity	NPC49603
0.894	High Similarity	NPC474442
0.8933	High Similarity	NPC238140
0.8933	High Similarity	NPC183380
0.8926	High Similarity	NPC175976
0.8924	High Similarity	NPC208818
0.8919	High Similarity	NPC324492
0.8919	High Similarity	NPC226540
0.8919	High Similarity	NPC125755
0.8919	High Similarity	NPC241846
0.8919	High Similarity	NPC162193
0.8919	High Similarity	NPC93610
0.8919	High Similarity	NPC260397
0.8919	High Similarity	NPC317053
0.8912	High Similarity	NPC253015
0.8912	High Similarity	NPC25292
0.8912	High Similarity	NPC473045
0.8912	High Similarity	NPC471065
0.8904	High Similarity	NPC189115
0.8904	High Similarity	NPC5262
0.8904	High Similarity	NPC475084
0.8904	High Similarity	NPC469559
0.8904	High Similarity	NPC472714
0.8904	High Similarity	NPC131971
0.8897	High Similarity	NPC55793
0.8882	High Similarity	NPC245615
0.8882	High Similarity	NPC61604
0.8882	High Similarity	NPC299706
0.8882	High Similarity	NPC115466
0.8881	High Similarity	NPC79957
0.8881	High Similarity	NPC174191
0.8873	High Similarity	NPC169973
0.8873	High Similarity	NPC26394
0.8873	High Similarity	NPC6836
0.8873	High Similarity	NPC25821
0.8867	High Similarity	NPC240521
0.8867	High Similarity	NPC55715
0.8867	High Similarity	NPC95392
0.8867	High Similarity	NPC35877
0.8859	High Similarity	NPC328567
0.8859	High Similarity	NPC320671
0.8859	High Similarity	NPC327412
0.8859	High Similarity	NPC320970
0.8851	High Similarity	NPC42716
0.8851	High Similarity	NPC307466
0.8851	High Similarity	NPC11422
0.8851	High Similarity	NPC178014
0.8851	High Similarity	NPC161700
0.8851	High Similarity	NPC474749
0.8851	High Similarity	NPC277867
0.8844	High Similarity	NPC473044
0.8836	High Similarity	NPC263261
0.8836	High Similarity	NPC469661
0.8836	High Similarity	NPC87725
0.8831	High Similarity	NPC478055
0.8831	High Similarity	NPC163635
0.8828	High Similarity	NPC183781
0.8819	High Similarity	NPC77861
0.8816	High Similarity	NPC21902
0.8811	High Similarity	NPC35731
0.8811	High Similarity	NPC478085
0.8808	High Similarity	NPC214326
0.8808	High Similarity	NPC469706
0.8808	High Similarity	NPC260781
0.8808	High Similarity	NPC218041
0.8808	High Similarity	NPC182368
0.8808	High Similarity	NPC145979
0.8808	High Similarity	NPC9933
0.8808	High Similarity	NPC469707
0.8808	High Similarity	NPC225815
0.8808	High Similarity	NPC185955
0.8803	High Similarity	NPC181049
0.8803	High Similarity	NPC104077
0.8803	High Similarity	NPC219671
0.8803	High Similarity	NPC147616
0.8803	High Similarity	NPC4940
0.8803	High Similarity	NPC252833
0.8803	High Similarity	NPC230219
0.8803	High Similarity	NPC207400
0.8803	High Similarity	NPC106739
0.8803	High Similarity	NPC471505
0.8803	High Similarity	NPC259742
0.88	High Similarity	NPC130959
0.88	High Similarity	NPC474940
0.88	High Similarity	NPC474795
0.88	High Similarity	NPC159697
0.88	High Similarity	NPC303013
0.8784	High Similarity	NPC63879
0.8784	High Similarity	NPC168579
0.8784	High Similarity	NPC470097
0.8784	High Similarity	NPC133251
0.8784	High Similarity	NPC45257
0.8784	High Similarity	NPC76176
0.8784	High Similarity	NPC93323

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 NPC98624 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	775
0.2-0.3	1775
0.3-0.4	2787
0.4-0.5	1803
0.5-0.6	1041
0.6-0.7	516
0.7-0.8	108
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8581	High Similarity	NPD6674	Discontinued
0.8344	Intermediate Similarity	NPD7228	Approved
0.8288	Intermediate Similarity	NPD1613	Approved
0.8288	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6234	Discontinued
0.8125	Intermediate Similarity	NPD4965	Approved
0.8125	Intermediate Similarity	NPD4966	Approved
0.8125	Intermediate Similarity	NPD4967	Phase 2
0.8082	Intermediate Similarity	NPD3027	Phase 3
0.8079	Intermediate Similarity	NPD7266	Discontinued
0.8025	Intermediate Similarity	NPD1653	Approved
0.8014	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD2861	Phase 2
0.7945	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD37	Approved
0.7935	Intermediate Similarity	NPD5058	Phase 3
0.7927	Intermediate Similarity	NPD7199	Phase 2
0.7917	Intermediate Similarity	NPD7074	Phase 3
0.7904	Intermediate Similarity	NPD3818	Discontinued
0.7902	Intermediate Similarity	NPD1091	Approved
0.7857	Intermediate Similarity	NPD7054	Approved
0.7824	Intermediate Similarity	NPD7240	Approved
0.7811	Intermediate Similarity	NPD7472	Approved
0.7785	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8455	Phase 2
0.7778	Intermediate Similarity	NPD3705	Approved
0.7746	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4060	Phase 1
0.7651	Intermediate Similarity	NPD4908	Phase 1
0.7616	Intermediate Similarity	NPD6559	Discontinued
0.7616	Intermediate Similarity	NPD7685	Pre-registration
0.7616	Intermediate Similarity	NPD7251	Discontinued
0.7572	Intermediate Similarity	NPD7808	Phase 3
0.7569	Intermediate Similarity	NPD1357	Approved
0.7566	Intermediate Similarity	NPD3620	Phase 2
0.7566	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6797	Phase 2
0.755	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD8651	Approved
0.75	Intermediate Similarity	NPD1934	Approved
0.7484	Intermediate Similarity	NPD5588	Approved
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7473	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7097	Phase 1
0.7419	Intermediate Similarity	NPD4538	Approved
0.7419	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4536	Approved
0.7405	Intermediate Similarity	NPD7680	Approved
0.7403	Intermediate Similarity	NPD5735	Approved
0.7397	Intermediate Similarity	NPD5126	Approved
0.7397	Intermediate Similarity	NPD5125	Phase 3
0.7394	Intermediate Similarity	NPD5283	Phase 1
0.7389	Intermediate Similarity	NPD5762	Approved
0.7389	Intermediate Similarity	NPD5763	Approved
0.7368	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6166	Phase 2
0.7365	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2977	Approved
0.7349	Intermediate Similarity	NPD2978	Approved
0.733	Intermediate Similarity	NPD8313	Approved
0.733	Intermediate Similarity	NPD7313	Approved
0.733	Intermediate Similarity	NPD7310	Approved
0.733	Intermediate Similarity	NPD7312	Approved
0.733	Intermediate Similarity	NPD7311	Approved
0.733	Intermediate Similarity	NPD8312	Approved
0.7321	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4749	Approved
0.7292	Intermediate Similarity	NPD7157	Approved
0.7292	Intermediate Similarity	NPD6671	Approved
0.729	Intermediate Similarity	NPD6355	Discontinued
0.7288	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7309	Approved
0.7278	Intermediate Similarity	NPD1375	Discontinued
0.7267	Intermediate Similarity	NPD27	Approved
0.7267	Intermediate Similarity	NPD6696	Suspended
0.7267	Intermediate Similarity	NPD2489	Approved
0.7263	Intermediate Similarity	NPD7906	Approved
0.7261	Intermediate Similarity	NPD4108	Discontinued
0.7261	Intermediate Similarity	NPD5960	Phase 3
0.7254	Intermediate Similarity	NPD228	Approved
0.725	Intermediate Similarity	NPD6331	Phase 2
0.7241	Intermediate Similarity	NPD5844	Phase 1
0.7235	Intermediate Similarity	NPD5494	Approved
0.7209	Intermediate Similarity	NPD2970	Approved
0.7209	Intermediate Similarity	NPD2969	Approved
0.7207	Intermediate Similarity	NPD4663	Approved
0.7205	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7843	Approved
0.72	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8127	Discontinued
0.7179	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5124	Phase 1
0.717	Intermediate Similarity	NPD6004	Phase 3
0.717	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6005	Phase 3
0.717	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6002	Phase 3
0.7167	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3882	Suspended
0.7151	Intermediate Similarity	NPD3051	Approved
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD2801	Approved
0.7135	Intermediate Similarity	NPD4578	Approved
0.7135	Intermediate Similarity	NPD4577	Approved
0.7127	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2424	Discontinued
0.7124	Intermediate Similarity	NPD3018	Phase 2
0.7118	Intermediate Similarity	NPD7075	Discontinued
0.7115	Intermediate Similarity	NPD1558	Phase 1
0.7113	Intermediate Similarity	NPD3022	Approved
0.7113	Intermediate Similarity	NPD3021	Approved
0.7086	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5177	Phase 3
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4380	Phase 2
0.7066	Intermediate Similarity	NPD7028	Phase 2
0.7052	Intermediate Similarity	NPD6071	Discontinued
0.7052	Intermediate Similarity	NPD3787	Discontinued
0.7049	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7033	Discontinued
0.7042	Intermediate Similarity	NPD2684	Approved
0.7037	Intermediate Similarity	NPD4110	Phase 3
0.7037	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7473	Discontinued
0.7025	Intermediate Similarity	NPD6653	Approved
0.7025	Intermediate Similarity	NPD6353	Approved
0.7006	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD2563	Approved
0.7	Intermediate Similarity	NPD2560	Approved
0.7	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3817	Phase 2
0.7	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6190	Approved
0.6994	Remote Similarity	NPD2677	Approved
0.6988	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6798	Discontinued
0.6978	Remote Similarity	NPD6842	Approved
0.6978	Remote Similarity	NPD6841	Approved
0.6978	Remote Similarity	NPD6843	Phase 3
0.6975	Remote Similarity	NPD4237	Approved
0.6975	Remote Similarity	NPD4236	Phase 3
0.6974	Remote Similarity	NPD5327	Phase 3
0.6974	Remote Similarity	NPD2983	Phase 2
0.6974	Remote Similarity	NPD2982	Phase 2
0.6972	Remote Similarity	NPD290	Approved
0.697	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6232	Discontinued
0.6951	Remote Similarity	NPD6667	Approved
0.6951	Remote Similarity	NPD6666	Approved
0.6948	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7819	Suspended
0.6941	Remote Similarity	NPD5772	Approved
0.6941	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5929	Approved
0.6941	Remote Similarity	NPD1465	Phase 2
0.6941	Remote Similarity	NPD5773	Approved
0.6933	Remote Similarity	NPD4535	Phase 3
0.6933	Remote Similarity	NPD4628	Phase 3
0.6933	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6072	Discontinued
0.6909	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1511	Approved
0.6909	Remote Similarity	NPD7041	Phase 2
0.6908	Remote Similarity	NPD2981	Phase 2
0.6905	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2238	Phase 2
0.6894	Remote Similarity	NPD6099	Approved
0.6894	Remote Similarity	NPD6100	Approved
0.6894	Remote Similarity	NPD2161	Phase 2
0.6893	Remote Similarity	NPD3751	Discontinued
0.6892	Remote Similarity	NPD7340	Approved
0.6889	Remote Similarity	NPD7549	Discontinued
0.6886	Remote Similarity	NPD5976	Discontinued
0.6883	Remote Similarity	NPD3094	Phase 2
0.6879	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1652	Phase 2
0.6871	Remote Similarity	NPD3060	Approved
0.6867	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7229	Phase 3
0.6848	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4210	Discontinued
0.6839	Remote Similarity	NPD4666	Phase 3
0.6839	Remote Similarity	NPD6584	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