NPASS Compound

Structure

CID323627 OpenBabel06191716172D 49 53 0 0 1 0 0 0 0 0999 V2000 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 2.5981 -0.5000 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 -3.4641 -3.0000 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 -5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -3.4641 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 3 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 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.0622 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 1 6 2 0 0 0 0 1 7 1 0 0 0 0 2 8 2 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 4 14 1 0 0 0 0 5 13 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 12 22 2 0 0 0 0 13 23 2 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 27 2 0 0 0 0 17 27 1 0 0 0 0 18 28 2 0 0 0 0 19 28 1 0 0 0 0 20 29 2 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 32 1 0 0 0 0 26 33 1 0 0 0 0 27 30 1 0 0 0 0 28 31 1 0 0 0 0 29 33 1 0 0 0 0 30 36 1 0 0 0 0 31 37 1 0 0 0 0 32 38 1 0 0 0 0 32 42 2 0 0 0 0 33 49 1 0 0 0 0 34 43 2 0 0 0 0 34 44 1 0 0 0 0 35 45 2 0 0 0 0 35 46 1 0 0 0 0 36 39 2 0 0 0 0 36 40 1 0 0 0 0 37 39 1 0 0 0 0 37 41 2 0 0 0 0 38 40 2 0 0 0 0 38 41 1 0 0 0 0 39 47 1 0 0 0 0 40 48 1 0 0 0 0 41 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	660.27
Volume:	700.412
LogP:	6.913
LogD:	3.606
LogS:	-3.035
# Rotatable Bonds:	15
TPSA:	141.36
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.073
Synthetic Accessibility Score:	4.317
Fsp3:	0.244
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.916
MDCK Permeability:	9.542735824652482e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.862
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	102.78498840332031%
Volume Distribution (VD):	0.137
Pgp-substrate:	0.2698429524898529%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.697
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.875
CYP2C9-inhibitor:	0.899
CYP2C9-substrate:	0.999
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.178
CYP3A4-inhibitor:	0.103
CYP3A4-substrate:	0.581

ADMET: Excretion

Clearance (CL):	-0.358
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.113
Carcinogencity:	0.058
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.266

Download Data

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

Natural Product: NPC323627

Natural Product ID:	NPC323627
*Common Name:**	(+/-)-Chartaceone C
IUPAC Name:	(E)-7-[8-[(E)-6-carboxy-1-phenylhex-2-enyl]-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-6-yl]-7-phenylhept-5-enoic acid
Synonyms:	(+/-)-Chartaceone C
Standard InCHIKey:	RGZSPQYXJSDKAN-FWSOMWAYSA-N
Standard InCHI:	InChI=1S/C41H40O8/c42-32-26-33(29-20-10-3-11-21-29)49-41-37(31(28-18-8-2-9-19-28)23-13-5-15-25-35(45)46)39(47)36(40(48)38(32)41)30(27-16-6-1-7-17-27)22-12-4-14-24-34(43)44/h1-3,6-13,16-23,30-31,33,47-48H,4-5,14-15,24-26H2,(H,43,44)(H,45,46)/b22-12+,23-13+
SMILES:	OC(=O)CCC/C=C/C(c1c(O)c2C(=O)CC(Oc2c(c1O)C(c1ccccc1)/C=C/CCCC(=O)O)c1ccccc1)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1940603
PubChem CID:	56834069
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO11348	Cryptocarya chartacea	Species	Lauraceae	Eukaryota	n.a.	trunk bark	n.a.	PMID[22050318]
NPO11348	Cryptocarya chartacea	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[22050318]
NPO11348	Cryptocarya chartacea	Species	Lauraceae	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

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	GI	=	0.0	%	PMID[459853]
NPT2	Others	Unspecified		IC50	=	4200.0	nM	PMID[459853]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[459853]

☑ 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 NPC323627 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	376
0.1-0.2	1509
0.2-0.3	3283
0.3-0.4	8001
0.4-0.5	10923
0.5-0.6	3880
0.6-0.7	6063
0.7-0.8	5774
0.8-0.85	2045
0.85-0.9	717
0.9-0.95	112
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC322459
1.0	High Similarity	NPC324358
1.0	High Similarity	NPC318527
0.9667	High Similarity	NPC121568
0.9605	High Similarity	NPC1796
0.9605	High Similarity	NPC257166
0.9542	High Similarity	NPC51247
0.9542	High Similarity	NPC15815
0.9533	High Similarity	NPC78835
0.9533	High Similarity	NPC309512
0.9533	High Similarity	NPC204561
0.9533	High Similarity	NPC317715
0.9533	High Similarity	NPC316960
0.9533	High Similarity	NPC148945
0.9481	High Similarity	NPC42965
0.9481	High Similarity	NPC98023
0.9481	High Similarity	NPC226462
0.9481	High Similarity	NPC195136
0.9474	High Similarity	NPC79375
0.9474	High Similarity	NPC37253
0.947	High Similarity	NPC39154
0.947	High Similarity	NPC115601
0.947	High Similarity	NPC208011
0.947	High Similarity	NPC78324
0.9416	High Similarity	NPC105584
0.9412	High Similarity	NPC32867
0.9412	High Similarity	NPC69531
0.9404	High Similarity	NPC178484
0.9359	High Similarity	NPC473012
0.9355	High Similarity	NPC121647
0.9351	High Similarity	NPC475184
0.9351	High Similarity	NPC208258
0.9346	High Similarity	NPC182555
0.9346	High Similarity	NPC66441
0.9346	High Similarity	NPC300668
0.9346	High Similarity	NPC134171
0.9342	High Similarity	NPC174086
0.9333	High Similarity	NPC122894
0.9299	High Similarity	NPC473009
0.9295	High Similarity	NPC312273
0.9295	High Similarity	NPC175513
0.9295	High Similarity	NPC301256
0.9295	High Similarity	NPC114652
0.929	High Similarity	NPC295090
0.9276	High Similarity	NPC209142
0.9276	High Similarity	NPC312549
0.9272	High Similarity	NPC3642
0.9272	High Similarity	NPC132345
0.9241	High Similarity	NPC473010
0.9231	High Similarity	NPC114147
0.9226	High Similarity	NPC271741
0.9226	High Similarity	NPC287789
0.9221	High Similarity	NPC201227
0.9221	High Similarity	NPC258474
0.9216	High Similarity	NPC43345
0.92	High Similarity	NPC228779
0.9182	High Similarity	NPC251336
0.9172	High Similarity	NPC97812
0.9167	High Similarity	NPC51760
0.9161	High Similarity	NPC56049
0.9161	High Similarity	NPC61112
0.9161	High Similarity	NPC198489
0.9161	High Similarity	NPC54830
0.9161	High Similarity	NPC309648
0.9156	High Similarity	NPC324447
0.915	High Similarity	NPC476551
0.915	High Similarity	NPC476553
0.915	High Similarity	NPC476552
0.9145	High Similarity	NPC104236
0.9145	High Similarity	NPC19238
0.9145	High Similarity	NPC164205
0.9139	High Similarity	NPC261271
0.9139	High Similarity	NPC475348
0.9133	High Similarity	NPC470136
0.9133	High Similarity	NPC470135
0.9133	High Similarity	NPC39045
0.9114	High Similarity	NPC473011
0.9097	High Similarity	NPC186227
0.9097	High Similarity	NPC265624
0.9097	High Similarity	NPC52611
0.9097	High Similarity	NPC205026
0.9097	High Similarity	NPC100049
0.9097	High Similarity	NPC215203
0.9097	High Similarity	NPC150908
0.9097	High Similarity	NPC14606
0.9097	High Similarity	NPC159707
0.9097	High Similarity	NPC158027
0.9097	High Similarity	NPC121649
0.9097	High Similarity	NPC248739
0.9079	High Similarity	NPC152233
0.9073	High Similarity	NPC470134
0.9073	High Similarity	NPC470131
0.9073	High Similarity	NPC470132
0.9073	High Similarity	NPC470133
0.9073	High Similarity	NPC473078
0.9073	High Similarity	NPC109183
0.9057	High Similarity	NPC63438
0.9045	High Similarity	NPC123544
0.9045	High Similarity	NPC195167
0.9032	High Similarity	NPC72425
0.9032	High Similarity	NPC194593
0.9032	High Similarity	NPC303485
0.9032	High Similarity	NPC71061
0.9032	High Similarity	NPC290830
0.9026	High Similarity	NPC111112
0.9026	High Similarity	NPC138299
0.9026	High Similarity	NPC67322
0.9026	High Similarity	NPC222713
0.902	High Similarity	NPC288840
0.902	High Similarity	NPC473016
0.902	High Similarity	NPC291746
0.9018	High Similarity	NPC168789
0.9007	High Similarity	NPC282957
0.9007	High Similarity	NPC235217
0.9007	High Similarity	NPC271288
0.9007	High Similarity	NPC194949
0.9007	High Similarity	NPC473014
0.8987	High Similarity	NPC292863
0.8987	High Similarity	NPC184326
0.8961	High Similarity	NPC474735
0.8957	High Similarity	NPC477529
0.8954	High Similarity	NPC145467
0.8947	High Similarity	NPC127059
0.8947	High Similarity	NPC25844
0.8947	High Similarity	NPC285630
0.8947	High Similarity	NPC181388
0.8947	High Similarity	NPC470322
0.8944	High Similarity	NPC224851
0.8944	High Similarity	NPC320741
0.8944	High Similarity	NPC171985
0.894	High Similarity	NPC278249
0.894	High Similarity	NPC85162
0.894	High Similarity	NPC77794
0.894	High Similarity	NPC81697
0.894	High Similarity	NPC107177
0.894	High Similarity	NPC223812
0.894	High Similarity	NPC125894
0.894	High Similarity	NPC185276
0.8938	High Similarity	NPC38591
0.8933	High Similarity	NPC248372
0.8933	High Similarity	NPC110038
0.8931	High Similarity	NPC137232
0.8931	High Similarity	NPC92589
0.8931	High Similarity	NPC18380
0.8924	High Similarity	NPC55443
0.8924	High Similarity	NPC90497
0.8924	High Similarity	NPC18699
0.8917	High Similarity	NPC471787
0.8903	High Similarity	NPC290671
0.8896	High Similarity	NPC76047
0.8896	High Similarity	NPC476365
0.8896	High Similarity	NPC469932
0.8889	High Similarity	NPC296998
0.8889	High Similarity	NPC10990
0.8889	High Similarity	NPC283234
0.8889	High Similarity	NPC473077
0.8889	High Similarity	NPC300988
0.8889	High Similarity	NPC140120
0.8889	High Similarity	NPC308200
0.8882	High Similarity	NPC196137
0.8882	High Similarity	NPC131568
0.8882	High Similarity	NPC131579
0.8882	High Similarity	NPC473013
0.8882	High Similarity	NPC471473
0.8882	High Similarity	NPC471524
0.8882	High Similarity	NPC471523
0.8882	High Similarity	NPC178627
0.8882	High Similarity	NPC197252
0.8882	High Similarity	NPC236766
0.8882	High Similarity	NPC1886
0.8882	High Similarity	NPC473015
0.8882	High Similarity	NPC469935
0.8875	High Similarity	NPC15374
0.8874	High Similarity	NPC125855
0.8874	High Similarity	NPC228504
0.8874	High Similarity	NPC107572
0.8874	High Similarity	NPC167624
0.8874	High Similarity	NPC227579
0.8874	High Similarity	NPC324436
0.8874	High Similarity	NPC220998
0.8874	High Similarity	NPC223500
0.8874	High Similarity	NPC64915
0.8874	High Similarity	NPC296917
0.8874	High Similarity	NPC166934
0.8874	High Similarity	NPC1089
0.8874	High Similarity	NPC161506
0.8874	High Similarity	NPC265040
0.8874	High Similarity	NPC37496
0.8874	High Similarity	NPC328164
0.8874	High Similarity	NPC32739
0.8874	High Similarity	NPC324134
0.8874	High Similarity	NPC10937
0.8874	High Similarity	NPC76338
0.8874	High Similarity	NPC182852
0.8874	High Similarity	NPC148757
0.8874	High Similarity	NPC78
0.8874	High Similarity	NPC166482
0.8874	High Similarity	NPC194432
0.8874	High Similarity	NPC76372
0.8874	High Similarity	NPC306829

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 NPC323627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	951
0.2-0.3	1568
0.3-0.4	2546
0.4-0.5	2033
0.5-0.6	1131
0.6-0.7	384
0.7-0.8	161
0.8-0.85	34
0.85-0.9	11
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9346	High Similarity	NPD8443	Clinical (unspecified phase)
0.9241	High Similarity	NPD7852	Clinical (unspecified phase)
0.9038	High Similarity	NPD7768	Phase 2
0.9026	High Similarity	NPD7411	Suspended
0.891	High Similarity	NPD7819	Suspended
0.8861	High Similarity	NPD7075	Discontinued
0.8812	High Similarity	NPD6959	Discontinued
0.8758	High Similarity	NPD7410	Clinical (unspecified phase)
0.8671	High Similarity	NPD7096	Clinical (unspecified phase)
0.8667	High Similarity	NPD1550	Clinical (unspecified phase)
0.8667	High Similarity	NPD1552	Clinical (unspecified phase)
0.8609	High Similarity	NPD1549	Phase 2
0.8599	High Similarity	NPD4380	Phase 2
0.8516	High Similarity	NPD4378	Clinical (unspecified phase)
0.8509	High Similarity	NPD3749	Approved
0.8494	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6166	Phase 2
0.8313	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8284	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.8258	Intermediate Similarity	NPD3750	Approved
0.8246	Intermediate Similarity	NPD8313	Approved
0.8246	Intermediate Similarity	NPD8312	Approved
0.8235	Intermediate Similarity	NPD2796	Approved
0.8148	Intermediate Similarity	NPD1934	Approved
0.8118	Intermediate Similarity	NPD7074	Phase 3
0.8101	Intermediate Similarity	NPD6799	Approved
0.8098	Intermediate Similarity	NPD8455	Phase 2
0.8084	Intermediate Similarity	NPD6232	Discontinued
0.8063	Intermediate Similarity	NPD5403	Approved
0.8059	Intermediate Similarity	NPD5844	Phase 1
0.8059	Intermediate Similarity	NPD7054	Approved
0.8026	Intermediate Similarity	NPD1240	Approved
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8013	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7977	Intermediate Similarity	NPD7808	Phase 3
0.7964	Intermediate Similarity	NPD5494	Approved
0.7939	Intermediate Similarity	NPD3817	Phase 2
0.7937	Intermediate Similarity	NPD2532	Approved
0.7937	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD2533	Approved
0.7937	Intermediate Similarity	NPD2534	Approved
0.7937	Intermediate Similarity	NPD5401	Approved
0.7935	Intermediate Similarity	NPD2799	Discontinued
0.7935	Intermediate Similarity	NPD3748	Approved
0.7922	Intermediate Similarity	NPD6651	Approved
0.7922	Intermediate Similarity	NPD1607	Approved
0.7921	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6559	Discontinued
0.7919	Intermediate Similarity	NPD7251	Discontinued
0.7881	Intermediate Similarity	NPD4908	Phase 1
0.7875	Intermediate Similarity	NPD7390	Discontinued
0.7875	Intermediate Similarity	NPD1511	Approved
0.7874	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6797	Phase 2
0.7861	Intermediate Similarity	NPD5953	Discontinued
0.7853	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7458	Discontinued
0.7848	Intermediate Similarity	NPD2800	Approved
0.7845	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5402	Approved
0.7812	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD1512	Approved
0.7778	Intermediate Similarity	NPD2313	Discontinued
0.7771	Intermediate Similarity	NPD2801	Approved
0.7771	Intermediate Similarity	NPD5408	Approved
0.7771	Intermediate Similarity	NPD5404	Approved
0.7771	Intermediate Similarity	NPD5406	Approved
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7771	Intermediate Similarity	NPD5405	Approved
0.7746	Intermediate Similarity	NPD7286	Phase 2
0.7744	Intermediate Similarity	NPD3226	Approved
0.7742	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5124	Phase 1
0.7736	Intermediate Similarity	NPD1243	Approved
0.773	Intermediate Similarity	NPD920	Approved
0.7716	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7003	Approved
0.7688	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.7679	Intermediate Similarity	NPD3882	Suspended
0.767	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6832	Phase 2
0.7611	Intermediate Similarity	NPD4287	Approved
0.761	Intermediate Similarity	NPD2346	Discontinued
0.7579	Intermediate Similarity	NPD8151	Discontinued
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1203	Approved
0.756	Intermediate Similarity	NPD1465	Phase 2
0.7558	Intermediate Similarity	NPD7229	Phase 3
0.7548	Intermediate Similarity	NPD3268	Approved
0.7547	Intermediate Similarity	NPD6099	Approved
0.7547	Intermediate Similarity	NPD6100	Approved
0.7541	Intermediate Similarity	NPD4360	Phase 2
0.7541	Intermediate Similarity	NPD4363	Phase 3
0.7533	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD8150	Discontinued
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7457	Intermediate Similarity	NPD5710	Approved
0.7457	Intermediate Similarity	NPD5711	Approved
0.7451	Intermediate Similarity	NPD2797	Approved
0.7417	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7783	Phase 2
0.7407	Intermediate Similarity	NPD7435	Discontinued
0.7399	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7177	Discontinued
0.7384	Intermediate Similarity	NPD919	Approved
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7871	Phase 2
0.7368	Intermediate Similarity	NPD7870	Phase 2
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7349	Intermediate Similarity	NPD6273	Approved
0.7348	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6798	Discontinued
0.7325	Intermediate Similarity	NPD3764	Approved
0.7317	Intermediate Similarity	NPD2309	Approved
0.7316	Intermediate Similarity	NPD7696	Phase 3
0.7316	Intermediate Similarity	NPD7697	Approved
0.7316	Intermediate Similarity	NPD7698	Approved
0.7314	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7097	Phase 1
0.731	Intermediate Similarity	NPD4288	Approved
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7296	Intermediate Similarity	NPD6355	Discontinued
0.729	Intermediate Similarity	NPD2798	Approved
0.7288	Intermediate Similarity	NPD3751	Discontinued
0.7288	Intermediate Similarity	NPD7228	Approved
0.7273	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3225	Approved
0.7268	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7874	Approved
0.7255	Intermediate Similarity	NPD9717	Approved
0.7255	Intermediate Similarity	NPD1608	Approved
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7235	Intermediate Similarity	NPD5890	Approved
0.7235	Intermediate Similarity	NPD5889	Approved
0.7226	Intermediate Similarity	NPD3267	Approved
0.7226	Intermediate Similarity	NPD3266	Approved
0.7219	Intermediate Similarity	NPD4361	Phase 2
0.7219	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3926	Phase 2
0.7202	Intermediate Similarity	NPD7584	Approved
0.7202	Intermediate Similarity	NPD7427	Discontinued
0.7193	Intermediate Similarity	NPD37	Approved
0.719	Intermediate Similarity	NPD422	Phase 1
0.7188	Intermediate Similarity	NPD8319	Approved
0.7188	Intermediate Similarity	NPD8320	Phase 1
0.7186	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6234	Discontinued
0.7178	Intermediate Similarity	NPD6005	Phase 3
0.7178	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6004	Phase 3
0.7178	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6002	Phase 3
0.7168	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD4966	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.716	Intermediate Similarity	NPD4308	Phase 3
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD7699	Phase 2
0.7126	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD943	Approved
0.7118	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1164	Approved
0.7105	Intermediate Similarity	NPD8285	Discontinued
0.7102	Intermediate Similarity	NPD8127	Discontinued
0.7093	Intermediate Similarity	NPD7577	Discontinued
0.7083	Intermediate Similarity	NPD6823	Phase 2
0.7083	Intermediate Similarity	NPD7447	Phase 1
0.7081	Intermediate Similarity	NPD1933	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