NPASS Compound

Structure

CID277369 OpenBabel06191716082D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 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 2.5981 1.5000 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 1.7321 -2.0000 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 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 1 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 -0.8660 -1.5000 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 -0.8660 -0.5000 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 -0.5000 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 0.0000 0.0000 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 8 1 0 0 0 0 4 10 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 13 2 0 0 0 0 7 12 1 0 0 0 0 7 21 1 0 0 0 0 8 1 1 6 0 0 0 8 21 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 18 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	287.755
LogP:	3.798
LogD:	2.737
LogS:	-3.917
# Rotatable Bonds:	2
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	3.037
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.992
MDCK Permeability:	1.222141509060748e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	95.47161102294922%
Volume Distribution (VD):	0.708
Pgp-substrate:	8.692893981933594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.889
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.17
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.415
CYP2C9-substrate:	0.813
CYP2D6-inhibitor:	0.414
CYP2D6-substrate:	0.682
CYP3A4-inhibitor:	0.244
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	13.227
Half-life (T1/2):	0.751

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.491
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.676
Rat Oral Acute Toxicity:	0.731
Maximum Recommended Daily Dose:	0.76
Skin Sensitization:	0.858
Carcinogencity:	0.449
Eye Corrosion:	0.004
Eye Irritation:	0.87
Respiratory Toxicity:	0.676

Download Data

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

Natural Product: NPC277369

Natural Product ID:	NPC277369
*Common Name:**	(S)-7,9-Dimethoxy-3-Methyl-3,4-Dihydro-1H-Benzo[G]Isochromene-5,10-Dione
IUPAC Name:	(3S)-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione
Synonyms:
Standard InCHIKey:	XOHGULAZSZLZHM-QMMMGPOBSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-8-4-10-12(7-21-8)16(18)14-11(15(10)17)5-9(19-2)6-13(14)20-3/h5-6,8H,4,7H2,1-3H3/t8-/m0/s1
SMILES:	COc1cc(OC)c2c(c1)C(=O)C1=C(C2=O)CO[C@H](C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL609285
PubChem CID:	45257195
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001649] Isochromanequinones [CHEMONTID:0002355] Benzoisochromanequinones

*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
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429996]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[17345316]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2140	Botryococcus braunii	Species	Botryococcaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7706	Bartlettina karwinskiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2140	Botryococcus braunii	Species	Botryococcaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9708	Aster verticillatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3035	Karwinskia humboldtiana	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
EC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	EC50	=	4460.0	nM	PMID[486400]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	EC50	=	12845.0	nM	PMID[486400]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	EC50	=	18035.0	nM	PMID[486400]

☑ 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 NPC277369 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	438
0.1-0.2	1655
0.2-0.3	4080
0.3-0.4	9941
0.4-0.5	8552
0.5-0.6	3741
0.6-0.7	6253
0.7-0.8	6125
0.8-0.85	1701
0.85-0.9	185
0.9-0.95	23
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC215451
0.9779	High Similarity	NPC109007
0.9296	High Similarity	NPC49282
0.9291	High Similarity	NPC167663
0.9241	High Similarity	NPC216917
0.9225	High Similarity	NPC475201
0.9178	High Similarity	NPC132990
0.9178	High Similarity	NPC46882
0.911	High Similarity	NPC470568
0.9091	High Similarity	NPC184702
0.9091	High Similarity	NPC189650
0.9085	High Similarity	NPC297985
0.9078	High Similarity	NPC156872
0.906	High Similarity	NPC472050
0.9054	High Similarity	NPC155686
0.9048	High Similarity	NPC470569
0.8986	High Similarity	NPC154683
0.8986	High Similarity	NPC40356
0.8986	High Similarity	NPC470340
0.898	High Similarity	NPC474660
0.8958	High Similarity	NPC19896
0.8951	High Similarity	NPC471644
0.8951	High Similarity	NPC471640
0.8921	High Similarity	NPC223354
0.8904	High Similarity	NPC289042
0.8904	High Similarity	NPC245584
0.8904	High Similarity	NPC56433
0.8904	High Similarity	NPC52106
0.8904	High Similarity	NPC118027
0.8904	High Similarity	NPC312929
0.8904	High Similarity	NPC190648
0.8904	High Similarity	NPC126767
0.8889	High Similarity	NPC472006
0.8889	High Similarity	NPC471639
0.8889	High Similarity	NPC471643
0.8865	High Similarity	NPC254741
0.8851	High Similarity	NPC473466
0.8851	High Similarity	NPC255641
0.8851	High Similarity	NPC147735
0.8851	High Similarity	NPC290954
0.8849	High Similarity	NPC182428
0.8844	High Similarity	NPC472056
0.8836	High Similarity	NPC470570
0.8828	High Similarity	NPC470932
0.8819	High Similarity	NPC469579
0.8819	High Similarity	NPC49108
0.8792	High Similarity	NPC232645
0.8792	High Similarity	NPC72958
0.8784	High Similarity	NPC97028
0.8784	High Similarity	NPC65775
0.8784	High Similarity	NPC97029
0.8784	High Similarity	NPC10027
0.8784	High Similarity	NPC158338
0.8784	High Similarity	NPC288036
0.8784	High Similarity	NPC100985
0.8784	High Similarity	NPC65589
0.8776	High Similarity	NPC474999
0.8767	High Similarity	NPC34482
0.8767	High Similarity	NPC28632
0.8759	High Similarity	NPC3732
0.8759	High Similarity	NPC476054
0.8758	High Similarity	NPC313368
0.875	High Similarity	NPC171094
0.875	High Similarity	NPC67650
0.875	High Similarity	NPC1704
0.875	High Similarity	NPC253822
0.875	High Similarity	NPC263483
0.8733	High Similarity	NPC87708
0.8733	High Similarity	NPC470338
0.8733	High Similarity	NPC51824
0.8733	High Similarity	NPC470337
0.8733	High Similarity	NPC268992
0.8733	High Similarity	NPC113608
0.8733	High Similarity	NPC180944
0.8732	High Similarity	NPC301341
0.8725	High Similarity	NPC294646
0.8716	High Similarity	NPC7025
0.8716	High Similarity	NPC172329
0.8716	High Similarity	NPC153417
0.8716	High Similarity	NPC27221
0.8716	High Similarity	NPC2569
0.8716	High Similarity	NPC256672
0.8707	High Similarity	NPC107625
0.8707	High Similarity	NPC472033
0.8707	High Similarity	NPC473927
0.8699	High Similarity	NPC48762
0.8693	High Similarity	NPC477410
0.869	High Similarity	NPC232021
0.869	High Similarity	NPC126534
0.869	High Similarity	NPC55832
0.869	High Similarity	NPC52789
0.869	High Similarity	NPC185607
0.869	High Similarity	NPC26051
0.869	High Similarity	NPC268204
0.869	High Similarity	NPC40118
0.8681	High Similarity	NPC469523
0.8681	High Similarity	NPC11566
0.8675	High Similarity	NPC93552
0.8675	High Similarity	NPC210942
0.8675	High Similarity	NPC169990
0.8675	High Similarity	NPC208806
0.8675	High Similarity	NPC214632
0.8671	High Similarity	NPC259685
0.8667	High Similarity	NPC478148
0.8667	High Similarity	NPC149526
0.8667	High Similarity	NPC474417
0.8667	High Similarity	NPC230848
0.8662	High Similarity	NPC99854
0.8662	High Similarity	NPC46869
0.8658	High Similarity	NPC4423
0.8658	High Similarity	NPC77325
0.8654	High Similarity	NPC316262
0.8654	High Similarity	NPC314653
0.8652	High Similarity	NPC292998
0.8652	High Similarity	NPC247743
0.8649	High Similarity	NPC34802
0.8649	High Similarity	NPC7943
0.8649	High Similarity	NPC123202
0.8649	High Similarity	NPC22005
0.8639	High Similarity	NPC171656
0.8639	High Similarity	NPC476055
0.8639	High Similarity	NPC471590
0.8639	High Similarity	NPC179970
0.8639	High Similarity	NPC472034
0.863	High Similarity	NPC469542
0.863	High Similarity	NPC51106
0.863	High Similarity	NPC84266
0.863	High Similarity	NPC310340
0.8627	High Similarity	NPC201127
0.8627	High Similarity	NPC246466
0.8623	High Similarity	NPC473907
0.8621	High Similarity	NPC204985
0.8621	High Similarity	NPC48624
0.8621	High Similarity	NPC80962
0.8621	High Similarity	NPC172250
0.8621	High Similarity	NPC265178
0.8621	High Similarity	NPC213659
0.8621	High Similarity	NPC259166
0.8621	High Similarity	NPC144118
0.8621	High Similarity	NPC472409
0.8621	High Similarity	NPC101366
0.8621	High Similarity	NPC326109
0.8621	High Similarity	NPC219917
0.8621	High Similarity	NPC215311
0.8618	High Similarity	NPC68727
0.8618	High Similarity	NPC226656
0.8618	High Similarity	NPC66508
0.8611	High Similarity	NPC25427
0.8611	High Similarity	NPC55162
0.8611	High Similarity	NPC12175
0.8611	High Similarity	NPC90665
0.8611	High Similarity	NPC278323
0.8611	High Similarity	NPC309154
0.8611	High Similarity	NPC279668
0.8609	High Similarity	NPC474843
0.8609	High Similarity	NPC288534
0.8601	High Similarity	NPC193792
0.8601	High Similarity	NPC161196
0.8601	High Similarity	NPC268081
0.8601	High Similarity	NPC284184
0.86	High Similarity	NPC295036
0.86	High Similarity	NPC225854
0.86	High Similarity	NPC85131
0.86	High Similarity	NPC202595
0.8592	High Similarity	NPC125269
0.8592	High Similarity	NPC470844
0.8591	High Similarity	NPC240253
0.8591	High Similarity	NPC240622
0.8591	High Similarity	NPC471642
0.8591	High Similarity	NPC476058
0.8591	High Similarity	NPC471641
0.8582	High Similarity	NPC101294
0.8582	High Similarity	NPC229646
0.8582	High Similarity	NPC473655
0.8581	High Similarity	NPC24136
0.8581	High Similarity	NPC469758
0.8581	High Similarity	NPC216314
0.8581	High Similarity	NPC120924
0.8581	High Similarity	NPC195919
0.8581	High Similarity	NPC290133
0.8581	High Similarity	NPC187282
0.8571	High Similarity	NPC324736
0.8571	High Similarity	NPC21599
0.8571	High Similarity	NPC59522
0.8571	High Similarity	NPC475705
0.8571	High Similarity	NPC182842
0.8571	High Similarity	NPC51887
0.8571	High Similarity	NPC471451
0.8571	High Similarity	NPC117836
0.8571	High Similarity	NPC470339
0.8571	High Similarity	NPC193703
0.8571	High Similarity	NPC477412
0.8571	High Similarity	NPC476178
0.8562	High Similarity	NPC94076
0.8562	High Similarity	NPC469404
0.8562	High Similarity	NPC474385
0.8562	High Similarity	NPC96692
0.8562	High Similarity	NPC182255
0.8561	High Similarity	NPC473894
0.8561	High Similarity	NPC211120

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 NPC277369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	994
0.2-0.3	1726
0.3-0.4	2666
0.4-0.5	1794
0.5-0.6	1056
0.6-0.7	381
0.7-0.8	137
0.8-0.85	19
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8865	High Similarity	NPD2796	Approved
0.8553	High Similarity	NPD7819	Suspended
0.8483	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1510	Phase 2
0.8389	Intermediate Similarity	NPD2532	Approved
0.8389	Intermediate Similarity	NPD2534	Approved
0.8389	Intermediate Similarity	NPD2533	Approved
0.828	Intermediate Similarity	NPD5494	Approved
0.8276	Intermediate Similarity	NPD3748	Approved
0.8267	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4380	Phase 2
0.8231	Intermediate Similarity	NPD1549	Phase 2
0.8228	Intermediate Similarity	NPD6959	Discontinued
0.8194	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1607	Approved
0.8125	Intermediate Similarity	NPD1240	Approved
0.8077	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.8054	Intermediate Similarity	NPD1243	Approved
0.8039	Intermediate Similarity	NPD920	Approved
0.8026	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8013	Intermediate Similarity	NPD6801	Discontinued
0.8013	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7962	Intermediate Similarity	NPD2801	Approved
0.7961	Intermediate Similarity	NPD6799	Approved
0.7949	Intermediate Similarity	NPD7411	Suspended
0.7933	Intermediate Similarity	NPD2800	Approved
0.7925	Intermediate Similarity	NPD7075	Discontinued
0.7911	Intermediate Similarity	NPD3817	Phase 2
0.7908	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3882	Suspended
0.7843	Intermediate Similarity	NPD1511	Approved
0.7821	Intermediate Similarity	NPD3226	Approved
0.7812	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7778	Intermediate Similarity	NPD1247	Approved
0.777	Intermediate Similarity	NPD6651	Approved
0.7764	Intermediate Similarity	NPD919	Approved
0.7758	Intermediate Similarity	NPD3818	Discontinued
0.7742	Intermediate Similarity	NPD1512	Approved
0.773	Intermediate Similarity	NPD5710	Approved
0.773	Intermediate Similarity	NPD5711	Approved
0.7711	Intermediate Similarity	NPD5844	Phase 1
0.7702	Intermediate Similarity	NPD3749	Approved
0.7697	Intermediate Similarity	NPD2654	Approved
0.7688	Intermediate Similarity	NPD5402	Approved
0.7682	Intermediate Similarity	NPD1471	Phase 3
0.7682	Intermediate Similarity	NPD2346	Discontinued
0.7647	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7768	Phase 2
0.764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6166	Phase 2
0.7616	Intermediate Similarity	NPD6100	Approved
0.7616	Intermediate Similarity	NPD6099	Approved
0.7616	Intermediate Similarity	NPD2935	Discontinued
0.7613	Intermediate Similarity	NPD7390	Discontinued
0.7606	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2798	Approved
0.7582	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD5403	Approved
0.7564	Intermediate Similarity	NPD5401	Approved
0.7552	Intermediate Similarity	NPD3972	Approved
0.755	Intermediate Similarity	NPD2799	Discontinued
0.7517	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7471	Intermediate Similarity	NPD6559	Discontinued
0.7456	Intermediate Similarity	NPD7074	Phase 3
0.7456	Intermediate Similarity	NPD7472	Approved
0.7451	Intermediate Similarity	NPD2344	Approved
0.7448	Intermediate Similarity	NPD1876	Approved
0.7419	Intermediate Similarity	NPD4628	Phase 3
0.7412	Intermediate Similarity	NPD5953	Discontinued
0.7412	Intermediate Similarity	NPD6797	Phase 2
0.74	Intermediate Similarity	NPD943	Approved
0.7394	Intermediate Similarity	NPD1651	Approved
0.7394	Intermediate Similarity	NPD5691	Approved
0.7383	Intermediate Similarity	NPD2313	Discontinued
0.7368	Intermediate Similarity	NPD7251	Discontinued
0.7351	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD230	Phase 1
0.7346	Intermediate Similarity	NPD37	Approved
0.7338	Intermediate Similarity	NPD1241	Discontinued
0.7337	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3751	Discontinued
0.7333	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7808	Phase 3
0.7326	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2403	Approved
0.732	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4965	Approved
0.7317	Intermediate Similarity	NPD4967	Phase 2
0.7317	Intermediate Similarity	NPD4966	Approved
0.7301	Intermediate Similarity	NPD1465	Phase 2
0.7273	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2309	Approved
0.7256	Intermediate Similarity	NPD5353	Approved
0.7256	Intermediate Similarity	NPD4288	Approved
0.7241	Intermediate Similarity	NPD1201	Approved
0.723	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6234	Discontinued
0.7209	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7229	Phase 3
0.7198	Intermediate Similarity	NPD6779	Approved
0.7198	Intermediate Similarity	NPD6776	Approved
0.7198	Intermediate Similarity	NPD6777	Approved
0.7198	Intermediate Similarity	NPD6782	Approved
0.7198	Intermediate Similarity	NPD6780	Approved
0.7198	Intermediate Similarity	NPD6778	Approved
0.7198	Intermediate Similarity	NPD6781	Approved
0.7193	Intermediate Similarity	NPD7286	Phase 2
0.7188	Intermediate Similarity	NPD6273	Approved
0.7183	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2979	Phase 3
0.7171	Intermediate Similarity	NPD4307	Phase 2
0.7166	Intermediate Similarity	NPD8151	Discontinued
0.7162	Intermediate Similarity	NPD3266	Approved
0.7162	Intermediate Similarity	NPD3267	Approved
0.7161	Intermediate Similarity	NPD5405	Approved
0.7161	Intermediate Similarity	NPD2438	Suspended
0.7161	Intermediate Similarity	NPD5406	Approved
0.7161	Intermediate Similarity	NPD5404	Approved
0.7161	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5242	Approved
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD4749	Approved
0.7134	Intermediate Similarity	NPD6280	Approved
0.7134	Intermediate Similarity	NPD6279	Approved
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1281	Approved
0.7114	Intermediate Similarity	NPD1019	Discontinued
0.7104	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4626	Approved
0.7103	Intermediate Similarity	NPD17	Approved
0.7101	Intermediate Similarity	NPD6808	Phase 2
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD7033	Discontinued
0.7091	Intermediate Similarity	NPD5760	Phase 2
0.7091	Intermediate Similarity	NPD5761	Phase 2
0.7089	Intermediate Similarity	NPD7003	Approved
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.7081	Intermediate Similarity	NPD7697	Approved
0.7081	Intermediate Similarity	NPD7435	Discontinued
0.7081	Intermediate Similarity	NPD7696	Phase 3
0.7081	Intermediate Similarity	NPD7698	Approved
0.7075	Intermediate Similarity	NPD9717	Approved
0.7062	Intermediate Similarity	NPD8150	Discontinued
0.7055	Intermediate Similarity	NPD7458	Discontinued
0.7049	Intermediate Similarity	NPD8285	Discontinued
0.7043	Intermediate Similarity	NPD7871	Phase 2
0.7043	Intermediate Similarity	NPD7870	Phase 2
0.7041	Intermediate Similarity	NPD7199	Phase 2
0.7039	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD411	Approved
0.7039	Intermediate Similarity	NPD3268	Approved
0.7039	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3764	Approved
0.703	Intermediate Similarity	NPD6844	Discontinued
0.702	Intermediate Similarity	NPD4908	Phase 1
0.7018	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4360	Phase 2
0.7017	Intermediate Similarity	NPD4363	Phase 3
0.7013	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1933	Approved
0.7013	Intermediate Similarity	NPD447	Suspended
0.7013	Intermediate Similarity	NPD5124	Phase 1
0.6993	Remote Similarity	NPD8032	Phase 2
0.6987	Remote Similarity	NPD4308	Phase 3
0.698	Remote Similarity	NPD1283	Approved
0.6971	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5890	Approved
0.697	Remote Similarity	NPD5889	Approved
0.6966	Remote Similarity	NPD9545	Approved
0.6959	Remote Similarity	NPD1608	Approved
0.6959	Remote Similarity	NPD7184	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data