NPASS Compound

Structure

NPC473927 OpenBabel07101718222D 24 25 0 0 0 0 0 0 0 0999 V2000 -1.6654 -1.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4982 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4982 -3.3654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 2.4038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4982 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6654 -1.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4982 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4982 0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3309 -2.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4982 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6654 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -0.4808 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 -3.3309 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1636 -3.3654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 0.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6654 0.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3309 -1.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 22 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 16 1 0 0 0 0 10 19 2 0 0 0 0 11 20 2 0 0 0 0 11 23 1 0 0 0 0 12 21 2 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 17 18 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.11
Volume:	334.421
LogP:	2.56
LogD:	2.018
LogS:	-3.955
# Rotatable Bonds:	6
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	2.513
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.831
MDCK Permeability:	2.939823934866581e-05
Pgp-inhibitor:	0.261
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.125
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	79.44141387939453%
Volume Distribution (VD):	0.778
Pgp-substrate:	35.732505798339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.539
CYP2C19-inhibitor:	0.743
CYP2C19-substrate:	0.261
CYP2C9-inhibitor:	0.7
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.425
CYP3A4-inhibitor:	0.557
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	2.181
Half-life (T1/2):	0.639

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.006
Drug-inuced Liver Injury (DILI):	0.39
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.684
Maximum Recommended Daily Dose:	0.479
Skin Sensitization:	0.941
Carcinogencity:	0.092
Eye Corrosion:	0.04
Eye Irritation:	0.927
Respiratory Toxicity:	0.506

Download Data

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

Natural Product: NPC473927

Natural Product ID:	NPC473927
*Common Name:**	Isotorachrysone Peracetate
IUPAC Name:	(6-acetyl-5-acetyloxy-4-methoxy-7-methylnaphthalen-2-yl) acetate
Synonyms:	Isotorachrysone Peracetate
Standard InCHIKey:	GXAOBNBMYYIETJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O6/c1-9-6-13-7-14(23-11(3)20)8-15(22-5)17(13)18(24-12(4)21)16(9)10(2)19/h6-8H,1-5H3
SMILES:	COc1cc(OC(=O)C)cc2c1c(OC(=O)C)c(c(c2)C)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455376
PubChem CID:	10520436
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO23980	Rhamnus nakaharai	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8691213]
NPO23980	Rhamnus nakaharai	Species	Rhamnaceae	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	1
Others	6

Activity Type	# Activity
NON-MOLECULAR	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	82.7	%	PMID[459978]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[459978]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	16.8	%	PMID[459978]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	86.7	%	PMID[459978]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5100.0	nM	PMID[459978]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	13.0	%	PMID[459978]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	83.0	%	PMID[459978]

☑ 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 NPC473927 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	444
0.1-0.2	1736
0.2-0.3	4238
0.3-0.4	10395
0.4-0.5	7979
0.5-0.6	3820
0.6-0.7	5953
0.7-0.8	5562
0.8-0.85	2108
0.85-0.9	407
0.9-0.95	51
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC474660
0.9574	High Similarity	NPC189650
0.9514	High Similarity	NPC291049
0.9514	High Similarity	NPC233267
0.9448	High Similarity	NPC473466
0.9444	High Similarity	NPC105415
0.9384	High Similarity	NPC133856
0.932	High Similarity	NPC273483
0.9247	High Similarity	NPC288036
0.9247	High Similarity	NPC65589
0.9247	High Similarity	NPC158338
0.9247	High Similarity	NPC100985
0.9247	High Similarity	NPC97029
0.9247	High Similarity	NPC97028
0.9236	High Similarity	NPC134621
0.9195	High Similarity	NPC89625
0.9195	High Similarity	NPC149618
0.9189	High Similarity	NPC217447
0.9178	High Similarity	NPC7025
0.9178	High Similarity	NPC27221
0.9178	High Similarity	NPC256672
0.9172	High Similarity	NPC237208
0.9172	High Similarity	NPC225173
0.9172	High Similarity	NPC163846
0.9167	High Similarity	NPC95123
0.9167	High Similarity	NPC66404
0.9133	High Similarity	NPC146211
0.9122	High Similarity	NPC474417
0.9122	High Similarity	NPC232645
0.9122	High Similarity	NPC149526
0.9122	High Similarity	NPC72958
0.911	High Similarity	NPC22005
0.911	High Similarity	NPC125801
0.911	High Similarity	NPC123202
0.911	High Similarity	NPC7943
0.9103	High Similarity	NPC29577
0.9097	High Similarity	NPC84266
0.9097	High Similarity	NPC471639
0.9097	High Similarity	NPC471643
0.9097	High Similarity	NPC167663
0.9078	High Similarity	NPC268081
0.906	High Similarity	NPC87708
0.9054	High Similarity	NPC60413
0.9054	High Similarity	NPC158866
0.9054	High Similarity	NPC325983
0.9048	High Similarity	NPC37139
0.9041	High Similarity	NPC267509
0.9028	High Similarity	NPC105648
0.9028	High Similarity	NPC24075
0.9028	High Similarity	NPC471644
0.9028	High Similarity	NPC182255
0.9028	High Similarity	NPC471640
0.9028	High Similarity	NPC94076
0.9021	High Similarity	NPC473209
0.9014	High Similarity	NPC253616
0.9	High Similarity	NPC210942
0.9	High Similarity	NPC329844
0.9	High Similarity	NPC169990
0.8993	High Similarity	NPC189773
0.8993	High Similarity	NPC478148
0.8986	High Similarity	NPC6923
0.898	High Similarity	NPC34802
0.8973	High Similarity	NPC49282
0.8973	High Similarity	NPC32470
0.8961	High Similarity	NPC108767
0.8958	High Similarity	NPC171094
0.8958	High Similarity	NPC220106
0.8954	High Similarity	NPC143050
0.8951	High Similarity	NPC36414
0.8933	High Similarity	NPC175978
0.8933	High Similarity	NPC154683
0.8933	High Similarity	NPC40356
0.8926	High Similarity	NPC119929
0.8926	High Similarity	NPC150928
0.8919	High Similarity	NPC2569
0.8919	High Similarity	NPC172329
0.8904	High Similarity	NPC470932
0.8897	High Similarity	NPC250755
0.8889	High Similarity	NPC136095
0.8889	High Similarity	NPC474373
0.8889	High Similarity	NPC165172
0.8889	High Similarity	NPC472515
0.8882	High Similarity	NPC180924
0.8882	High Similarity	NPC4547
0.8881	High Similarity	NPC103001
0.8874	High Similarity	NPC472799
0.8867	High Similarity	NPC258249
0.8859	High Similarity	NPC329933
0.8851	High Similarity	NPC12305
0.8844	High Similarity	NPC312789
0.8836	High Similarity	NPC310340
0.8824	High Similarity	NPC246647
0.8824	High Similarity	NPC212967
0.8824	High Similarity	NPC96342
0.8824	High Similarity	NPC164110
0.8824	High Similarity	NPC263483
0.8811	High Similarity	NPC161196
0.88	High Similarity	NPC307780
0.88	High Similarity	NPC309979
0.88	High Similarity	NPC202595
0.879	High Similarity	NPC30027
0.8784	High Similarity	NPC470322
0.8784	High Similarity	NPC154217
0.8782	High Similarity	NPC156082
0.8767	High Similarity	NPC469579
0.8759	High Similarity	NPC472523
0.8759	High Similarity	NPC262635
0.8759	High Similarity	NPC168471
0.8758	High Similarity	NPC474983
0.875	High Similarity	NPC259685
0.8742	High Similarity	NPC227166
0.8733	High Similarity	NPC65775
0.8733	High Similarity	NPC10027
0.8726	High Similarity	NPC112981
0.8725	High Similarity	NPC190648
0.8725	High Similarity	NPC56433
0.8725	High Similarity	NPC126767
0.8725	High Similarity	NPC312929
0.8725	High Similarity	NPC245584
0.8725	High Similarity	NPC289042
0.8725	High Similarity	NPC118027
0.8716	High Similarity	NPC196137
0.8716	High Similarity	NPC1886
0.871	High Similarity	NPC186325
0.871	High Similarity	NPC47623
0.8707	High Similarity	NPC159721
0.8707	High Similarity	NPC36181
0.8707	High Similarity	NPC215451
0.8707	High Similarity	NPC277369
0.8707	High Similarity	NPC472006
0.8699	High Similarity	NPC275734
0.8699	High Similarity	NPC470856
0.8699	High Similarity	NPC67650
0.8699	High Similarity	NPC1704
0.8693	High Similarity	NPC148938
0.869	High Similarity	NPC17848
0.8684	High Similarity	NPC271681
0.8681	High Similarity	NPC254741
0.8681	High Similarity	NPC472516
0.8679	High Similarity	NPC99613
0.8679	High Similarity	NPC49487
0.8675	High Similarity	NPC470107
0.8675	High Similarity	NPC227122
0.8675	High Similarity	NPC470568
0.8675	High Similarity	NPC194379
0.8675	High Similarity	NPC295036
0.8675	High Similarity	NPC191104
0.8671	High Similarity	NPC20216
0.8671	High Similarity	NPC29160
0.8671	High Similarity	NPC470844
0.8667	High Similarity	NPC472056
0.8667	High Similarity	NPC240622
0.8667	High Similarity	NPC471641
0.8667	High Similarity	NPC471642
0.8667	High Similarity	NPC240253
0.8662	High Similarity	NPC101294
0.8662	High Similarity	NPC474350
0.8662	High Similarity	NPC473655
0.8658	High Similarity	NPC196114
0.8658	High Similarity	NPC181388
0.8658	High Similarity	NPC187282
0.8658	High Similarity	NPC130176
0.8658	High Similarity	NPC290133
0.8658	High Similarity	NPC24136
0.8658	High Similarity	NPC99454
0.8654	High Similarity	NPC189552
0.8654	High Similarity	NPC273467
0.8654	High Similarity	NPC66288
0.8649	High Similarity	NPC94794
0.8649	High Similarity	NPC196459
0.8649	High Similarity	NPC42540
0.8649	High Similarity	NPC87609
0.8649	High Similarity	NPC188632
0.8649	High Similarity	NPC470296
0.8649	High Similarity	NPC112791
0.8649	High Similarity	NPC184702
0.8649	High Similarity	NPC151607
0.8645	High Similarity	NPC85121
0.8645	High Similarity	NPC177650
0.8639	High Similarity	NPC254010
0.8639	High Similarity	NPC297985
0.8639	High Similarity	NPC49108
0.863	High Similarity	NPC472366
0.863	High Similarity	NPC109007
0.863	High Similarity	NPC11566
0.8627	High Similarity	NPC214632
0.8627	High Similarity	NPC473664
0.8627	High Similarity	NPC135522
0.8627	High Similarity	NPC475895
0.8627	High Similarity	NPC235333
0.8627	High Similarity	NPC477691
0.8625	High Similarity	NPC20543
0.8625	High Similarity	NPC239440
0.8621	High Similarity	NPC38153
0.8618	High Similarity	NPC312549
0.8618	High Similarity	NPC473732
0.8618	High Similarity	NPC209142
0.8618	High Similarity	NPC106372
0.8618	High Similarity	NPC470569
0.8618	High Similarity	NPC58668

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 NPC473927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	1020
0.2-0.3	1657
0.3-0.4	2639
0.4-0.5	1811
0.5-0.6	1066
0.6-0.7	394
0.7-0.8	141
0.8-0.85	38
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD7819	Suspended
0.8759	High Similarity	NPD1243	Approved
0.8591	High Similarity	NPD2534	Approved
0.8591	High Similarity	NPD2533	Approved
0.8591	High Similarity	NPD2532	Approved
0.8562	High Similarity	NPD970	Clinical (unspecified phase)
0.8553	High Similarity	NPD6599	Discontinued
0.8552	High Similarity	NPD2796	Approved
0.8535	High Similarity	NPD6959	Discontinued
0.8483	Intermediate Similarity	NPD3748	Approved
0.8481	Intermediate Similarity	NPD6232	Discontinued
0.8477	Intermediate Similarity	NPD920	Approved
0.8467	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7473	Discontinued
0.84	Intermediate Similarity	NPD6799	Approved
0.8387	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD7411	Suspended
0.8366	Intermediate Similarity	NPD3226	Approved
0.8344	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8291	Intermediate Similarity	NPD919	Approved
0.8269	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD2346	Discontinued
0.8228	Intermediate Similarity	NPD3749	Approved
0.8228	Intermediate Similarity	NPD7075	Discontinued
0.8219	Intermediate Similarity	NPD1607	Approved
0.8217	Intermediate Similarity	NPD3817	Phase 2
0.8205	Intermediate Similarity	NPD6801	Discontinued
0.82	Intermediate Similarity	NPD3750	Approved
0.8165	Intermediate Similarity	NPD7768	Phase 2
0.8148	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5494	Approved
0.8121	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD2799	Discontinued
0.8105	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD1240	Approved
0.8069	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1549	Phase 2
0.8056	Intermediate Similarity	NPD6832	Phase 2
0.8054	Intermediate Similarity	NPD2935	Discontinued
0.8054	Intermediate Similarity	NPD1551	Phase 2
0.8013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1510	Phase 2
0.7975	Intermediate Similarity	NPD1934	Approved
0.7943	Intermediate Similarity	NPD1281	Approved
0.7925	Intermediate Similarity	NPD2801	Approved
0.7922	Intermediate Similarity	NPD1511	Approved
0.7922	Intermediate Similarity	NPD7390	Discontinued
0.7914	Intermediate Similarity	NPD5710	Approved
0.7914	Intermediate Similarity	NPD5711	Approved
0.7905	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2800	Approved
0.7866	Intermediate Similarity	NPD3926	Phase 2
0.7857	Intermediate Similarity	NPD6559	Discontinued
0.7857	Intermediate Similarity	NPD1651	Approved
0.7848	Intermediate Similarity	NPD4380	Phase 2
0.7843	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD4628	Phase 3
0.7838	Intermediate Similarity	NPD2979	Phase 3
0.7826	Intermediate Similarity	NPD3882	Suspended
0.7821	Intermediate Similarity	NPD1512	Approved
0.7815	Intermediate Similarity	NPD6100	Approved
0.7815	Intermediate Similarity	NPD6099	Approved
0.7812	Intermediate Similarity	NPD1465	Phase 2
0.7801	Intermediate Similarity	NPD17	Approved
0.7785	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1283	Approved
0.7771	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1247	Approved
0.773	Intermediate Similarity	NPD5691	Approved
0.7725	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3267	Approved
0.7724	Intermediate Similarity	NPD3266	Approved
0.7718	Intermediate Similarity	NPD4307	Phase 2
0.7716	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2313	Discontinued
0.7697	Intermediate Similarity	NPD5408	Approved
0.7697	Intermediate Similarity	NPD5405	Approved
0.7697	Intermediate Similarity	NPD7229	Phase 3
0.7697	Intermediate Similarity	NPD2438	Suspended
0.7697	Intermediate Similarity	NPD5406	Approved
0.7697	Intermediate Similarity	NPD5404	Approved
0.7692	Intermediate Similarity	NPD5953	Discontinued
0.7692	Intermediate Similarity	NPD1611	Approved
0.7669	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5403	Approved
0.7654	Intermediate Similarity	NPD5402	Approved
0.7647	Intermediate Similarity	NPD1471	Phase 3
0.7643	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD5401	Approved
0.7639	Intermediate Similarity	NPD3972	Approved
0.7639	Intermediate Similarity	NPD1608	Approved
0.7635	Intermediate Similarity	NPD4625	Phase 3
0.7616	Intermediate Similarity	NPD6651	Approved
0.7613	Intermediate Similarity	NPD7003	Approved
0.7605	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6166	Phase 2
0.7603	Intermediate Similarity	NPD1203	Approved
0.7584	Intermediate Similarity	NPD3268	Approved
0.7584	Intermediate Similarity	NPD411	Approved
0.7584	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1296	Phase 2
0.7582	Intermediate Similarity	NPD2531	Phase 2
0.7574	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7286	Phase 2
0.7552	Intermediate Similarity	NPD4626	Approved
0.7548	Intermediate Similarity	NPD2654	Approved
0.7533	Intermediate Similarity	NPD8032	Phase 2
0.7532	Intermediate Similarity	NPD2344	Approved
0.7529	Intermediate Similarity	NPD7074	Phase 3
0.7517	Intermediate Similarity	NPD9717	Approved
0.7516	Intermediate Similarity	NPD4308	Phase 3
0.7515	Intermediate Similarity	NPD7177	Discontinued
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6273	Approved
0.7483	Intermediate Similarity	NPD2797	Approved
0.7471	Intermediate Similarity	NPD7054	Approved
0.7458	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4288	Approved
0.7434	Intermediate Similarity	NPD1933	Approved
0.7432	Intermediate Similarity	NPD2798	Approved
0.7432	Intermediate Similarity	NPD1019	Discontinued
0.7427	Intermediate Similarity	NPD7472	Approved
0.7425	Intermediate Similarity	NPD7199	Phase 2
0.7399	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6797	Phase 2
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7355	Intermediate Similarity	NPD4476	Approved
0.7355	Intermediate Similarity	NPD4477	Approved
0.7346	Intermediate Similarity	NPD7458	Discontinued
0.7342	Intermediate Similarity	NPD2309	Approved
0.7341	Intermediate Similarity	NPD7251	Discontinued
0.7337	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD422	Phase 1
0.732	Intermediate Similarity	NPD447	Suspended
0.7317	Intermediate Similarity	NPD37	Approved
0.7308	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7808	Phase 3
0.7297	Intermediate Similarity	NPD1876	Approved
0.729	Intermediate Similarity	NPD7033	Discontinued
0.7289	Intermediate Similarity	NPD4965	Approved
0.7289	Intermediate Similarity	NPD4967	Phase 2
0.7289	Intermediate Similarity	NPD4966	Approved
0.7283	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6808	Phase 2
0.7256	Intermediate Similarity	NPD5890	Approved
0.7256	Intermediate Similarity	NPD5889	Approved
0.7255	Intermediate Similarity	NPD943	Approved
0.7255	Intermediate Similarity	NPD4060	Phase 1
0.7247	Intermediate Similarity	NPD4287	Approved
0.7237	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5242	Approved
0.7234	Intermediate Similarity	NPD8151	Discontinued
0.7219	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8285	Discontinued
0.7211	Intermediate Similarity	NPD1201	Approved
0.7208	Intermediate Similarity	NPD5124	Phase 1
0.7208	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD230	Phase 1
0.7202	Intermediate Similarity	NPD6234	Discontinued
0.7195	Intermediate Similarity	NPD6585	Discontinued
0.7193	Intermediate Similarity	NPD2403	Approved
0.7192	Intermediate Similarity	NPD1778	Approved
0.7181	Intermediate Similarity	NPD3225	Approved
0.7176	Intermediate Similarity	NPD3787	Discontinued
0.716	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7783	Phase 2
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1164	Approved
0.7133	Intermediate Similarity	NPD1470	Approved
0.7125	Intermediate Similarity	NPD3887	Approved
0.7124	Intermediate Similarity	NPD3764	Approved
0.7114	Intermediate Similarity	NPD4749	Approved
0.7113	Intermediate Similarity	NPD5535	Approved
0.711	Intermediate Similarity	NPD3751	Discontinued
0.7108	Intermediate Similarity	NPD6280	Approved
0.7108	Intermediate Similarity	NPD6279	Approved
0.7105	Intermediate Similarity	NPD4908	Phase 1
0.7097	Intermediate Similarity	NPD6355	Discontinued
0.7093	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2353	Approved
0.7081	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1241	Discontinued
0.7059	Intermediate Similarity	NPD7435	Discontinued
0.7041	Intermediate Similarity	NPD6971	Discontinued
0.7039	Intermediate Similarity	NPD8150	Discontinued

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