NPASS Compound

Structure

CID317053 OpenBabel06191716132D 42 46 0 0 1 0 0 0 0 0999 V2000 -4.0492 -6.2230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0011 3.4765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5447 -2.6517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4582 -3.0584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8402 -4.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0209 -0.9410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2129 -2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7357 -3.2394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6142 -1.8546 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6197 -1.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5627 -4.0529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7537 -4.6407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8221 -2.8327 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4118 -0.7719 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4763 -4.4597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8583 -5.6352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9561 -3.3327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2778 -0.2719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 36 1 0 0 0 0 2 37 1 0 0 0 0 3 38 1 0 0 0 0 4 39 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 18 1 0 0 0 0 7 22 2 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 21 1 0 0 0 0 10 16 2 0 0 0 0 10 23 1 0 0 0 0 11 17 2 0 0 0 0 11 24 1 0 0 0 0 12 17 1 0 0 0 0 12 25 2 0 0 0 0 13 32 1 0 0 0 0 14 41 1 0 0 0 0 15 40 1 0 0 0 0 18 27 1 0 0 0 0 18 30 2 0 0 0 0 19 14 1 6 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 15 1 6 0 0 0 20 29 1 0 0 0 0 21 23 2 0 0 0 0 21 33 1 0 0 0 0 22 30 1 0 0 0 0 22 34 1 0 0 0 0 23 36 1 0 0 0 0 24 31 2 0 0 0 0 24 37 1 0 0 0 0 25 31 1 0 0 0 0 25 38 1 0 0 0 0 26 13 1 1 0 0 0 26 27 1 0 0 0 0 26 42 1 0 0 0 0 27 35 1 1 0 0 0 28 16 1 1 0 0 0 28 40 1 0 0 0 0 29 17 1 1 0 0 0 29 41 1 0 0 0 0 30 39 1 0 0 0 0 31 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.23
Volume:	574.914
LogP:	2.2
LogD:	2.473
LogS:	-4.282
# Rotatable Bonds:	11
TPSA:	145.53
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.262
Synthetic Accessibility Score:	4.493
Fsp3:	0.419
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.582
MDCK Permeability:	2.0188421331113204e-05
Pgp-inhibitor:	0.42
Pgp-substrate:	0.419
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	79.65795135498047%
Volume Distribution (VD):	0.52
Pgp-substrate:	16.388118743896484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.602
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.752
CYP2C9-inhibitor:	0.517
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.305
CYP2D6-substrate:	0.406
CYP3A4-inhibitor:	0.722
CYP3A4-substrate:	0.722

ADMET: Excretion

Clearance (CL):	4.405
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.393
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.348
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.424
Skin Sensitization:	0.913
Carcinogencity:	0.098
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.052

Download Data

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

Natural Product: NPC317053

Natural Product ID:	NPC317053
*Common Name:**	(-)-(7R,7'r,7''r,8S,8's,8''s)-4',4''-Dihydroxy-3,3',3'',5-Tetramethoxy-7,9':7',9-Diepoxy-4,8''-Oxy-8,8'-Sesquineolignan-7'',9''-Diol
IUPAC Name:	(1R,2S)-2-[4-[(3R,3aS,6R,6aS)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenoxy]-1-(3-hydroxy-2-methoxyphenyl)propane-1,3-diol
Synonyms:
Standard InCHIKey:	QHRLSLOEICSBNJ-UOILNLDMSA-N
Standard InCHI:	InChI=1S/C31H36O11/c1-36-23-10-16(8-9-21(23)33)28-19-14-41-29(20(19)15-40-28)17-11-24(37-2)31(25(12-17)38-3)42-26(13-32)27(35)18-6-5-7-22(34)30(18)39-4/h5-12,19-20,26-29,32-35H,13-15H2,1-4H3/t19-,20-,26+,27-,28+,29+/m1/s1
SMILES:	COC1=CC(=CC(=C1OC(CO)C(C2=C(C(=CC=C2)O)OC)O)OC)C3C4COC(C4CO3)C5=CC(=C(C=C5)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797775
PubChem CID:	56680033
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid 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
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22690646]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	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

Activity Type	# Activity
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	<	30.0	%	PMID[483331]

☑ 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 NPC317053 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	464
0.1-0.2	1390
0.2-0.3	4039
0.3-0.4	10751
0.4-0.5	8131
0.5-0.6	4555
0.6-0.7	7491
0.7-0.8	4431
0.8-0.85	952
0.85-0.9	434
0.9-0.95	44
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC324492
0.9928	High Similarity	NPC320970
0.9928	High Similarity	NPC320671
0.9928	High Similarity	NPC328567
0.9928	High Similarity	NPC327412
0.9855	High Similarity	NPC114119
0.9855	High Similarity	NPC470097
0.9855	High Similarity	NPC471415
0.9714	High Similarity	NPC260397
0.965	High Similarity	NPC329343
0.965	High Similarity	NPC324517
0.965	High Similarity	NPC321972
0.9565	High Similarity	NPC291101
0.9565	High Similarity	NPC266197
0.951	High Similarity	NPC473266
0.951	High Similarity	NPC470826
0.951	High Similarity	NPC470098
0.9504	High Similarity	NPC181615
0.9424	High Similarity	NPC184797
0.9424	High Similarity	NPC309124
0.9357	High Similarity	NPC178054
0.9357	High Similarity	NPC263261
0.9357	High Similarity	NPC311530
0.9357	High Similarity	NPC87725
0.9353	High Similarity	NPC236306
0.9353	High Similarity	NPC473739
0.9353	High Similarity	NPC22517
0.9353	High Similarity	NPC232164
0.9348	High Similarity	NPC77861
0.9291	High Similarity	NPC107161
0.9286	High Similarity	NPC254759
0.9286	High Similarity	NPC160283
0.9286	High Similarity	NPC55793
0.9275	High Similarity	NPC99572
0.9275	High Similarity	NPC165155
0.9275	High Similarity	NPC24490
0.9275	High Similarity	NPC141765
0.9275	High Similarity	NPC34103
0.9275	High Similarity	NPC126409
0.9252	High Similarity	NPC470769
0.9241	High Similarity	NPC55158
0.9241	High Similarity	NPC51328
0.9241	High Similarity	NPC286235
0.9225	High Similarity	NPC477616
0.922	High Similarity	NPC247291
0.922	High Similarity	NPC471389
0.9214	High Similarity	NPC292882
0.9209	High Similarity	NPC16435
0.9209	High Similarity	NPC248727
0.9209	High Similarity	NPC162659
0.9209	High Similarity	NPC270456
0.9209	High Similarity	NPC265433
0.9209	High Similarity	NPC306441
0.9203	High Similarity	NPC287745
0.9203	High Similarity	NPC326095
0.9203	High Similarity	NPC244983
0.9189	High Similarity	NPC157333
0.9178	High Similarity	NPC477612
0.9172	High Similarity	NPC20757
0.9172	High Similarity	NPC248132
0.9172	High Similarity	NPC227516
0.9172	High Similarity	NPC329836
0.9172	High Similarity	NPC130449
0.9161	High Similarity	NPC93323
0.9161	High Similarity	NPC304894
0.9161	High Similarity	NPC63879
0.9161	High Similarity	NPC45257
0.9161	High Similarity	NPC280092
0.9161	High Similarity	NPC15659
0.9161	High Similarity	NPC12641
0.9149	High Similarity	NPC22317
0.9149	High Similarity	NPC27495
0.9143	High Similarity	NPC477938
0.9137	High Similarity	NPC234333
0.9137	High Similarity	NPC260898
0.9137	High Similarity	NPC47398
0.9137	High Similarity	NPC112939
0.9137	High Similarity	NPC94750
0.9137	High Similarity	NPC474206
0.9137	High Similarity	NPC470356
0.9137	High Similarity	NPC121812
0.9137	High Similarity	NPC61946
0.9137	High Similarity	NPC93783
0.9137	High Similarity	NPC112246
0.913	High Similarity	NPC475840
0.913	High Similarity	NPC158331
0.911	High Similarity	NPC211561
0.9103	High Similarity	NPC39657
0.9091	High Similarity	NPC102044
0.9091	High Similarity	NPC173203
0.9091	High Similarity	NPC163508
0.9091	High Similarity	NPC47633
0.9091	High Similarity	NPC469630
0.9091	High Similarity	NPC85264
0.9085	High Similarity	NPC470372
0.9078	High Similarity	NPC25966
0.9078	High Similarity	NPC471388
0.9078	High Similarity	NPC319647
0.9078	High Similarity	NPC70682
0.9078	High Similarity	NPC127218
0.9078	High Similarity	NPC245207
0.9078	High Similarity	NPC260741
0.9071	High Similarity	NPC29799
0.9071	High Similarity	NPC227503
0.9071	High Similarity	NPC209985
0.9071	High Similarity	NPC230734
0.9071	High Similarity	NPC302701
0.9071	High Similarity	NPC10737
0.9071	High Similarity	NPC177160
0.9071	High Similarity	NPC472336
0.9071	High Similarity	NPC269091
0.9071	High Similarity	NPC54743
0.9071	High Similarity	NPC263367
0.9071	High Similarity	NPC156502
0.9071	High Similarity	NPC474639
0.9071	High Similarity	NPC472334
0.9071	High Similarity	NPC477939
0.9065	High Similarity	NPC170694
0.9065	High Similarity	NPC317380
0.9065	High Similarity	NPC478085
0.9058	High Similarity	NPC160991
0.9058	High Similarity	NPC175067
0.9058	High Similarity	NPC184447
0.9058	High Similarity	NPC470752
0.9058	High Similarity	NPC7903
0.9058	High Similarity	NPC35932
0.9058	High Similarity	NPC16208
0.9058	High Similarity	NPC204215
0.9048	High Similarity	NPC472710
0.9048	High Similarity	NPC472709
0.9041	High Similarity	NPC301961
0.9041	High Similarity	NPC166584
0.9028	High Similarity	NPC171932
0.9028	High Similarity	NPC28440
0.9021	High Similarity	NPC302506
0.9007	High Similarity	NPC103976
0.9007	High Similarity	NPC102904
0.9007	High Similarity	NPC176051
0.9007	High Similarity	NPC276490
0.9007	High Similarity	NPC474390
0.9007	High Similarity	NPC470827
0.9007	High Similarity	NPC107551
0.9007	High Similarity	NPC474282
0.9007	High Similarity	NPC211549
0.9007	High Similarity	NPC326797
0.9	High Similarity	NPC151224
0.9	High Similarity	NPC134968
0.9	High Similarity	NPC472337
0.9	High Similarity	NPC202104
0.9	High Similarity	NPC164787
0.8993	High Similarity	NPC263064
0.8993	High Similarity	NPC229442
0.8993	High Similarity	NPC168059
0.8993	High Similarity	NPC11060
0.8986	High Similarity	NPC469613
0.8986	High Similarity	NPC30043
0.8986	High Similarity	NPC309787
0.8986	High Similarity	NPC470096
0.8986	High Similarity	NPC161557
0.8986	High Similarity	NPC228346
0.8986	High Similarity	NPC158079
0.8986	High Similarity	NPC470095
0.8986	High Similarity	NPC7171
0.8986	High Similarity	NPC469625
0.8986	High Similarity	NPC472597
0.8986	High Similarity	NPC27843
0.8986	High Similarity	NPC40432
0.8986	High Similarity	NPC474017
0.8986	High Similarity	NPC115207
0.8973	High Similarity	NPC21776
0.8973	High Similarity	NPC204770
0.8973	High Similarity	NPC236202
0.8973	High Similarity	NPC263940
0.8973	High Similarity	NPC58190
0.8973	High Similarity	NPC82917
0.8973	High Similarity	NPC70409
0.8973	High Similarity	NPC101376
0.8973	High Similarity	NPC108811
0.8973	High Similarity	NPC294558
0.8973	High Similarity	NPC202742
0.8973	High Similarity	NPC18185
0.8973	High Similarity	NPC262911
0.8973	High Similarity	NPC16269
0.8973	High Similarity	NPC170103
0.8966	High Similarity	NPC279298
0.8966	High Similarity	NPC180953
0.8966	High Similarity	NPC22150
0.8966	High Similarity	NPC38041
0.8966	High Similarity	NPC475096
0.8958	High Similarity	NPC81638
0.8951	High Similarity	NPC35216
0.8947	High Similarity	NPC470828
0.8944	High Similarity	NPC184613
0.8944	High Similarity	NPC6300
0.8944	High Similarity	NPC114171
0.8944	High Similarity	NPC230124
0.8944	High Similarity	NPC260842
0.8936	High Similarity	NPC234952
0.8936	High Similarity	NPC470802
0.8936	High Similarity	NPC173660

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 NPC317053 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	827
0.2-0.3	1874
0.3-0.4	2807
0.4-0.5	1670
0.5-0.6	970
0.6-0.7	531
0.7-0.8	106
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8921	High Similarity	NPD1612	Clinical (unspecified phase)
0.8921	High Similarity	NPD1613	Approved
0.8841	High Similarity	NPD3027	Phase 3
0.8633	High Similarity	NPD1529	Clinical (unspecified phase)
0.8561	High Similarity	NPD1530	Clinical (unspecified phase)
0.85	High Similarity	NPD4908	Phase 1
0.838	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6234	Discontinued
0.8239	Intermediate Similarity	NPD7199	Phase 2
0.8217	Intermediate Similarity	NPD4967	Phase 2
0.8217	Intermediate Similarity	NPD4966	Approved
0.8217	Intermediate Similarity	NPD4965	Approved
0.821	Intermediate Similarity	NPD7228	Approved
0.8129	Intermediate Similarity	NPD1610	Phase 2
0.8086	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6166	Phase 2
0.8086	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD2861	Phase 2
0.8025	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1934	Approved
0.8025	Intermediate Similarity	NPD37	Approved
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1653	Approved
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7877	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1548	Phase 1
0.7829	Intermediate Similarity	NPD6674	Discontinued
0.7793	Intermediate Similarity	NPD3018	Phase 2
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.777	Intermediate Similarity	NPD3620	Phase 2
0.777	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3882	Suspended
0.7762	Intermediate Similarity	NPD4749	Approved
0.775	Intermediate Similarity	NPD2801	Approved
0.7725	Intermediate Similarity	NPD7054	Approved
0.7692	Intermediate Similarity	NPD7240	Approved
0.7687	Intermediate Similarity	NPD4625	Phase 3
0.7679	Intermediate Similarity	NPD7472	Approved
0.7639	Intermediate Similarity	NPD2982	Phase 2
0.7639	Intermediate Similarity	NPD2983	Phase 2
0.7619	Intermediate Similarity	NPD5844	Phase 1
0.7609	Intermediate Similarity	NPD5283	Phase 1
0.76	Intermediate Similarity	NPD5735	Approved
0.7597	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2981	Phase 2
0.7533	Intermediate Similarity	NPD4060	Phase 1
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1511	Approved
0.7515	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD7157	Approved
0.75	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3817	Phase 2
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7483	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7447	Phase 1
0.7468	Intermediate Similarity	NPD7266	Discontinued
0.7466	Intermediate Similarity	NPD8651	Approved
0.7464	Intermediate Similarity	NPD228	Approved
0.7442	Intermediate Similarity	NPD7808	Phase 3
0.7436	Intermediate Similarity	NPD7466	Approved
0.7427	Intermediate Similarity	NPD6797	Phase 2
0.7425	Intermediate Similarity	NPD6232	Discontinued
0.7421	Intermediate Similarity	NPD1512	Approved
0.7414	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7843	Approved
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7212	Phase 2
0.7405	Intermediate Similarity	NPD7213	Phase 3
0.74	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6559	Discontinued
0.7379	Intermediate Similarity	NPD1091	Approved
0.7379	Intermediate Similarity	NPD3705	Approved
0.7377	Intermediate Similarity	NPD7680	Approved
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8054	Approved
0.7356	Intermediate Similarity	NPD8053	Approved
0.7355	Intermediate Similarity	NPD5763	Approved
0.7355	Intermediate Similarity	NPD5762	Approved
0.7348	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4380	Phase 2
0.7341	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7549	Discontinued
0.7338	Intermediate Similarity	NPD5588	Approved
0.733	Intermediate Similarity	NPD7906	Approved
0.7325	Intermediate Similarity	NPD3892	Phase 2
0.7321	Intermediate Similarity	NPD7229	Phase 3
0.7319	Intermediate Similarity	NPD3022	Approved
0.7319	Intermediate Similarity	NPD3021	Approved
0.7317	Intermediate Similarity	NPD1465	Phase 2
0.7303	Intermediate Similarity	NPD1558	Phase 1
0.729	Intermediate Similarity	NPD6100	Approved
0.729	Intermediate Similarity	NPD6099	Approved
0.7289	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7075	Discontinued
0.7285	Intermediate Similarity	NPD6798	Discontinued
0.7279	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4538	Approved
0.7273	Intermediate Similarity	NPD4663	Approved
0.7273	Intermediate Similarity	NPD4536	Approved
0.7273	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD8127	Discontinued
0.7261	Intermediate Similarity	NPD1652	Phase 2
0.7261	Intermediate Similarity	NPD5177	Phase 3
0.7255	Intermediate Similarity	NPD5124	Phase 1
0.7255	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6671	Approved
0.7248	Intermediate Similarity	NPD6584	Phase 3
0.7246	Intermediate Similarity	NPD2684	Approved
0.7244	Intermediate Similarity	NPD3540	Phase 1
0.7244	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6516	Phase 2
0.7241	Intermediate Similarity	NPD5846	Approved
0.7239	Intermediate Similarity	NPD4678	Approved
0.7239	Intermediate Similarity	NPD4675	Approved
0.7235	Intermediate Similarity	NPD2489	Approved
0.7235	Intermediate Similarity	NPD27	Approved
0.7233	Intermediate Similarity	NPD5058	Phase 3
0.7219	Intermediate Similarity	NPD7095	Approved
0.7219	Intermediate Similarity	NPD3051	Approved
0.7215	Intermediate Similarity	NPD6331	Phase 2
0.7212	Intermediate Similarity	NPD8455	Phase 2
0.72	Intermediate Similarity	NPD4578	Approved
0.72	Intermediate Similarity	NPD7311	Approved
0.72	Intermediate Similarity	NPD7312	Approved
0.72	Intermediate Similarity	NPD4577	Approved
0.72	Intermediate Similarity	NPD7313	Approved
0.72	Intermediate Similarity	NPD7310	Approved
0.7179	Intermediate Similarity	NPD3539	Phase 1
0.7178	Intermediate Similarity	NPD4005	Discontinued
0.7176	Intermediate Similarity	NPD2969	Approved
0.7176	Intermediate Similarity	NPD2970	Approved
0.7174	Intermediate Similarity	NPD290	Approved
0.7172	Intermediate Similarity	NPD1357	Approved
0.717	Intermediate Similarity	NPD6190	Approved
0.717	Intermediate Similarity	NPD2677	Approved
0.7169	Intermediate Similarity	NPD2560	Approved
0.7169	Intermediate Similarity	NPD2563	Approved
0.7162	Intermediate Similarity	NPD5327	Phase 3
0.7162	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6959	Discontinued
0.7159	Intermediate Similarity	NPD7309	Approved
0.7152	Intermediate Similarity	NPD4236	Phase 3
0.7152	Intermediate Similarity	NPD4237	Approved
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7768	Phase 2
0.7125	Intermediate Similarity	NPD7124	Phase 2
0.7124	Intermediate Similarity	NPD6233	Phase 2
0.7118	Intermediate Similarity	NPD6071	Discontinued
0.7115	Intermediate Similarity	NPD5960	Phase 3
0.7115	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6696	Suspended
0.711	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7819	Suspended
0.7107	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4110	Phase 3
0.7107	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6353	Approved
0.7097	Intermediate Similarity	NPD6653	Approved
0.7091	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1549	Phase 2
0.7078	Intermediate Similarity	NPD2238	Phase 2
0.7078	Intermediate Similarity	NPD4140	Approved
0.7078	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3926	Phase 2
0.707	Intermediate Similarity	NPD2161	Phase 2
0.7067	Intermediate Similarity	NPD3094	Phase 2
0.7066	Intermediate Similarity	NPD5402	Approved
0.7051	Intermediate Similarity	NPD7097	Phase 1
0.7048	Intermediate Similarity	NPD6801	Discontinued
0.7047	Intermediate Similarity	NPD6582	Phase 2
0.7047	Intermediate Similarity	NPD6583	Phase 3
0.7044	Intermediate Similarity	NPD3060	Approved
0.7037	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6004	Phase 3
0.7025	Intermediate Similarity	NPD6005	Phase 3
0.7025	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1375	Discontinued
0.7025	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6002	Phase 3
0.7018	Intermediate Similarity	NPD3787	Discontinued
0.7011	Intermediate Similarity	NPD8156	Discontinued
0.7006	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2977	Approved
0.7006	Intermediate Similarity	NPD2978	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data