NPASS Compound

Structure

NPC310135 OpenBabel07101718282D 22 24 0 0 1 0 0 0 0 0999 V2000 3.4641 -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 -2.5981 0.5000 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 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 -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 0.0000 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 1.7321 2.0000 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 0.5000 0.0000 C 0 0 1 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 0.8660 1.5000 0.0000 C 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 -0.8660 -1.5000 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 3.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 11 2 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 14 10 1 6 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	2.826
LogD:	2.664
LogS:	-4.08
# Rotatable Bonds:	2
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	2.951
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.794
MDCK Permeability:	1.3371648492466193e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	94.68122100830078%
Volume Distribution (VD):	0.758
Pgp-substrate:	7.163038730621338%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.893
CYP2C19-inhibitor:	0.768
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.79
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.655
CYP2D6-substrate:	0.854
CYP3A4-inhibitor:	0.764
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	15.581
Half-life (T1/2):	0.694

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.146
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.918
Carcinogencity:	0.487
Eye Corrosion:	0.017
Eye Irritation:	0.937
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC310135

Natural Product ID:	NPC310135
*Common Name:**	Artocarpanone
IUPAC Name:	(2S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-2,3-dihydrochromen-4-one
Synonyms:	Artocarpanone
Standard InCHIKey:	FQGBGNHGEUOZIW-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)10-3-2-8(17)4-11(10)18/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
SMILES:	COc1cc(c2C(=O)C[C@@H](c3ccc(cc3O)O)Oc2c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467194
PubChem CID:	15298902
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(95)00135-T]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Wood	n.a.	n.a.	PMID[23113717]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	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	4

Activity Type	# Activity
NON-MOLECULAR	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.1	%	PMID[526094]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	90.2	%	PMID[526094]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	38.6	%	PMID[526094]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[526094]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	41000.0	nM	PMID[526094]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	90700.0	nM	PMID[526094]

☑ 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 NPC310135 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	343
0.1-0.2	1523
0.2-0.3	3905
0.3-0.4	10266
0.4-0.5	8020
0.5-0.6	3583
0.6-0.7	5564
0.7-0.8	5341
0.8-0.85	2236
0.85-0.9	1168
0.9-0.95	571
0.95-1	177

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC265871
1.0	High Similarity	NPC20709
1.0	High Similarity	NPC329203
1.0	High Similarity	NPC150648
1.0	High Similarity	NPC225153
1.0	High Similarity	NPC222342
1.0	High Similarity	NPC274784
0.9925	High Similarity	NPC6407
0.9925	High Similarity	NPC188243
0.9925	High Similarity	NPC110228
0.9852	High Similarity	NPC213322
0.9852	High Similarity	NPC4743
0.9852	High Similarity	NPC312391
0.9852	High Similarity	NPC324386
0.9851	High Similarity	NPC140890
0.985	High Similarity	NPC107586
0.985	High Similarity	NPC243083
0.985	High Similarity	NPC287246
0.985	High Similarity	NPC79943
0.985	High Similarity	NPC296490
0.985	High Similarity	NPC12296
0.985	High Similarity	NPC13768
0.985	High Similarity	NPC32441
0.985	High Similarity	NPC295261
0.9779	High Similarity	NPC223500
0.9779	High Similarity	NPC161506
0.9779	High Similarity	NPC296917
0.9779	High Similarity	NPC324134
0.9779	High Similarity	NPC182852
0.9779	High Similarity	NPC194432
0.9779	High Similarity	NPC220998
0.9779	High Similarity	NPC148757
0.9779	High Similarity	NPC32739
0.9779	High Similarity	NPC37496
0.9779	High Similarity	NPC166934
0.9779	High Similarity	NPC107572
0.9779	High Similarity	NPC76338
0.9779	High Similarity	NPC306829
0.9779	High Similarity	NPC78
0.9779	High Similarity	NPC265040
0.9779	High Similarity	NPC125855
0.9779	High Similarity	NPC167624
0.9779	High Similarity	NPC10937
0.9779	High Similarity	NPC228504
0.9779	High Similarity	NPC166482
0.9779	High Similarity	NPC324436
0.9779	High Similarity	NPC76372
0.9779	High Similarity	NPC177354
0.9779	High Similarity	NPC66515
0.9779	High Similarity	NPC328164
0.9779	High Similarity	NPC64915
0.9779	High Similarity	NPC227579
0.9779	High Similarity	NPC40833
0.9779	High Similarity	NPC1089
0.9778	High Similarity	NPC129853
0.9778	High Similarity	NPC284550
0.9778	High Similarity	NPC76445
0.9776	High Similarity	NPC472460
0.9776	High Similarity	NPC118813
0.9776	High Similarity	NPC99333
0.9776	High Similarity	NPC280284
0.9776	High Similarity	NPC188947
0.9776	High Similarity	NPC147686
0.9776	High Similarity	NPC329225
0.9708	High Similarity	NPC175504
0.9708	High Similarity	NPC278249
0.9708	High Similarity	NPC143896
0.9708	High Similarity	NPC223812
0.9708	High Similarity	NPC85162
0.9708	High Similarity	NPC75049
0.9708	High Similarity	NPC39329
0.9708	High Similarity	NPC316816
0.9708	High Similarity	NPC310130
0.9708	High Similarity	NPC150408
0.9708	High Similarity	NPC81697
0.9708	High Similarity	NPC91560
0.9708	High Similarity	NPC68104
0.9708	High Similarity	NPC164980
0.9708	High Similarity	NPC149026
0.9708	High Similarity	NPC185276
0.9708	High Similarity	NPC214166
0.9708	High Similarity	NPC221432
0.9708	High Similarity	NPC257097
0.9708	High Similarity	NPC125894
0.9708	High Similarity	NPC107177
0.9708	High Similarity	NPC169591
0.9708	High Similarity	NPC77794
0.9708	High Similarity	NPC478086
0.9706	High Similarity	NPC156190
0.9706	High Similarity	NPC166689
0.9706	High Similarity	NPC258630
0.9706	High Similarity	NPC96408
0.9706	High Similarity	NPC279650
0.9706	High Similarity	NPC3188
0.9706	High Similarity	NPC248372
0.9706	High Similarity	NPC110038
0.9706	High Similarity	NPC17170
0.9704	High Similarity	NPC261234
0.9701	High Similarity	NPC275055
0.9701	High Similarity	NPC290291
0.9701	High Similarity	NPC84585
0.9701	High Similarity	NPC476480
0.9638	High Similarity	NPC131568
0.9638	High Similarity	NPC209040
0.9638	High Similarity	NPC236766
0.9638	High Similarity	NPC235217
0.9638	High Similarity	NPC197252
0.9638	High Similarity	NPC473013
0.9638	High Similarity	NPC473014
0.9638	High Similarity	NPC131579
0.9638	High Similarity	NPC473015
0.9635	High Similarity	NPC202981
0.9635	High Similarity	NPC73028
0.963	High Similarity	NPC124269
0.9627	High Similarity	NPC124784
0.9627	High Similarity	NPC29353
0.9627	High Similarity	NPC234133
0.9627	High Similarity	NPC473887
0.9627	High Similarity	NPC47815
0.9627	High Similarity	NPC231772
0.9627	High Similarity	NPC127447
0.9627	High Similarity	NPC194281
0.9568	High Similarity	NPC83357
0.9568	High Similarity	NPC109183
0.9568	High Similarity	NPC214774
0.9568	High Similarity	NPC301276
0.9568	High Similarity	NPC470134
0.9568	High Similarity	NPC142405
0.9568	High Similarity	NPC176229
0.9568	High Similarity	NPC20488
0.9568	High Similarity	NPC470132
0.9568	High Similarity	NPC312973
0.9568	High Similarity	NPC88964
0.9568	High Similarity	NPC267375
0.9568	High Similarity	NPC246948
0.9568	High Similarity	NPC285630
0.9568	High Similarity	NPC470133
0.9568	High Similarity	NPC475052
0.9568	High Similarity	NPC127059
0.9568	High Similarity	NPC470131
0.9568	High Similarity	NPC473078
0.9568	High Similarity	NPC111786
0.9568	High Similarity	NPC67805
0.9568	High Similarity	NPC470647
0.9568	High Similarity	NPC195621
0.9568	High Similarity	NPC472629
0.9568	High Similarity	NPC54577
0.9565	High Similarity	NPC113770
0.9559	High Similarity	NPC316480
0.9559	High Similarity	NPC18260
0.9559	High Similarity	NPC78913
0.9556	High Similarity	NPC250266
0.9556	High Similarity	NPC266597
0.9556	High Similarity	NPC188879
0.9552	High Similarity	NPC239495
0.9552	High Similarity	NPC9985
0.9552	High Similarity	NPC99854
0.95	High Similarity	NPC23728
0.95	High Similarity	NPC296998
0.95	High Similarity	NPC472627
0.95	High Similarity	NPC110303
0.95	High Similarity	NPC476182
0.95	High Similarity	NPC40086
0.95	High Similarity	NPC122828
0.95	High Similarity	NPC300988
0.95	High Similarity	NPC176869
0.95	High Similarity	NPC473077
0.95	High Similarity	NPC3779
0.95	High Similarity	NPC211466
0.95	High Similarity	NPC10990
0.95	High Similarity	NPC44721
0.95	High Similarity	NPC283234
0.9496	High Similarity	NPC470135
0.9496	High Similarity	NPC110776
0.9496	High Similarity	NPC271590
0.9496	High Similarity	NPC87486
0.9496	High Similarity	NPC271288
0.9496	High Similarity	NPC124780
0.9496	High Similarity	NPC184649
0.9496	High Similarity	NPC470136
0.9496	High Similarity	NPC470890
0.9496	High Similarity	NPC303185
0.9496	High Similarity	NPC39045
0.9496	High Similarity	NPC311144
0.9496	High Similarity	NPC319752
0.9493	High Similarity	NPC147145
0.9489	High Similarity	NPC182421
0.9489	High Similarity	NPC241100
0.9489	High Similarity	NPC69769
0.9489	High Similarity	NPC159275
0.9485	High Similarity	NPC201395
0.9481	High Similarity	NPC13408
0.9481	High Similarity	NPC240593
0.9433	High Similarity	NPC132592
0.9433	High Similarity	NPC161191
0.9433	High Similarity	NPC160821
0.9429	High Similarity	NPC187282
0.9429	High Similarity	NPC474161
0.9429	High Similarity	NPC476153
0.9429	High Similarity	NPC299011

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 NPC310135 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	925
0.2-0.3	1524
0.3-0.4	2540
0.4-0.5	1910
0.5-0.6	1230
0.6-0.7	492
0.7-0.8	145
0.8-0.85	37
0.85-0.9	21
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.985	High Similarity	NPD1550	Clinical (unspecified phase)
0.985	High Similarity	NPD1552	Clinical (unspecified phase)
0.9776	High Similarity	NPD1549	Phase 2
0.9265	High Similarity	NPD1510	Phase 2
0.9254	High Similarity	NPD1240	Approved
0.922	High Similarity	NPD4378	Clinical (unspecified phase)
0.9197	High Similarity	NPD2796	Approved
0.9172	High Similarity	NPD1934	Approved
0.9118	High Similarity	NPD1607	Approved
0.911	High Similarity	NPD2393	Clinical (unspecified phase)
0.9048	High Similarity	NPD8443	Clinical (unspecified phase)
0.8973	High Similarity	NPD7411	Suspended
0.8951	High Similarity	NPD7410	Clinical (unspecified phase)
0.8926	High Similarity	NPD7075	Discontinued
0.8904	High Similarity	NPD4380	Phase 2
0.8851	High Similarity	NPD7096	Clinical (unspecified phase)
0.88	High Similarity	NPD4381	Clinical (unspecified phase)
0.875	High Similarity	NPD1511	Approved
0.875	High Similarity	NPD6799	Approved
0.8725	High Similarity	NPD7819	Suspended
0.8658	High Similarity	NPD6801	Discontinued
0.863	High Similarity	NPD1512	Approved
0.86	High Similarity	NPD2801	Approved
0.8581	High Similarity	NPD6167	Clinical (unspecified phase)
0.8581	High Similarity	NPD6166	Phase 2
0.8581	High Similarity	NPD6168	Clinical (unspecified phase)
0.8551	High Similarity	NPD6859	Clinical (unspecified phase)
0.8542	High Similarity	NPD3750	Approved
0.8523	High Similarity	NPD6599	Discontinued
0.8521	High Similarity	NPD1551	Phase 2
0.8506	High Similarity	NPD6959	Discontinued
0.8487	Intermediate Similarity	NPD3882	Suspended
0.8472	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8433	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD3749	Approved
0.8418	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD7768	Phase 2
0.8365	Intermediate Similarity	NPD7074	Phase 3
0.8345	Intermediate Similarity	NPD2800	Approved
0.8322	Intermediate Similarity	NPD5403	Approved
0.8311	Intermediate Similarity	NPD5401	Approved
0.8302	Intermediate Similarity	NPD7054	Approved
0.8301	Intermediate Similarity	NPD3817	Phase 2
0.825	Intermediate Similarity	NPD7472	Approved
0.8247	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD3818	Discontinued
0.8207	Intermediate Similarity	NPD2344	Approved
0.8205	Intermediate Similarity	NPD5494	Approved
0.8199	Intermediate Similarity	NPD6797	Phase 2
0.8194	Intermediate Similarity	NPD3748	Approved
0.8188	Intermediate Similarity	NPD1203	Approved
0.8182	Intermediate Similarity	NPD6651	Approved
0.8163	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD1610	Phase 2
0.8148	Intermediate Similarity	NPD7251	Discontinued
0.8143	Intermediate Similarity	NPD4908	Phase 1
0.8134	Intermediate Similarity	NPD1548	Phase 1
0.8098	Intermediate Similarity	NPD7808	Phase 3
0.8095	Intermediate Similarity	NPD1243	Approved
0.8079	Intermediate Similarity	NPD920	Approved
0.8069	Intermediate Similarity	NPD7033	Discontinued
0.8054	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD4628	Phase 3
0.8037	Intermediate Similarity	NPD6559	Discontinued
0.8028	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6099	Approved
0.8014	Intermediate Similarity	NPD6100	Approved
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.8014	Intermediate Similarity	NPD6832	Phase 2
0.7988	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2309	Approved
0.7975	Intermediate Similarity	NPD5953	Discontinued
0.7971	Intermediate Similarity	NPD9717	Approved
0.7963	Intermediate Similarity	NPD7286	Phase 2
0.7949	Intermediate Similarity	NPD5402	Approved
0.7947	Intermediate Similarity	NPD2534	Approved
0.7947	Intermediate Similarity	NPD2532	Approved
0.7947	Intermediate Similarity	NPD2533	Approved
0.7947	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD2799	Discontinued
0.7917	Intermediate Similarity	NPD943	Approved
0.7902	Intermediate Similarity	NPD3268	Approved
0.7902	Intermediate Similarity	NPD2313	Discontinued
0.7899	Intermediate Similarity	NPD422	Phase 1
0.7875	Intermediate Similarity	NPD6232	Discontinued
0.7853	Intermediate Similarity	NPD5844	Phase 1
0.784	Intermediate Similarity	NPD7473	Discontinued
0.7823	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD2797	Approved
0.7793	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1613	Approved
0.7758	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2798	Approved
0.7742	Intermediate Similarity	NPD3226	Approved
0.774	Intermediate Similarity	NPD1933	Approved
0.774	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5124	Phase 1
0.7737	Intermediate Similarity	NPD9545	Approved
0.7733	Intermediate Similarity	NPD4363	Phase 3
0.7733	Intermediate Similarity	NPD4360	Phase 2
0.7733	Intermediate Similarity	NPD2654	Approved
0.773	Intermediate Similarity	NPD3225	Approved
0.7718	Intermediate Similarity	NPD2346	Discontinued
0.7712	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4308	Phase 3
0.7688	Intermediate Similarity	NPD919	Approved
0.7682	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3266	Approved
0.7676	Intermediate Similarity	NPD3267	Approved
0.7658	Intermediate Similarity	NPD1465	Phase 2
0.7655	Intermediate Similarity	NPD6798	Discontinued
0.7639	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1241	Discontinued
0.7619	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD3926	Phase 2
0.7593	Intermediate Similarity	NPD1247	Approved
0.7591	Intermediate Similarity	NPD9493	Approved
0.7589	Intermediate Similarity	NPD1608	Approved
0.7589	Intermediate Similarity	NPD3972	Approved
0.7569	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1296	Phase 2
0.7532	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD6104	Discontinued
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD4288	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4361	Phase 2
0.7485	Intermediate Similarity	NPD1729	Discontinued
0.747	Intermediate Similarity	NPD3751	Discontinued
0.7466	Intermediate Similarity	NPD4625	Phase 3
0.7448	Intermediate Similarity	NPD2861	Phase 2
0.7439	Intermediate Similarity	NPD5710	Approved
0.7439	Intermediate Similarity	NPD5711	Approved
0.7432	Intermediate Similarity	NPD4307	Phase 2
0.7419	Intermediate Similarity	NPD7212	Phase 2
0.7419	Intermediate Similarity	NPD7213	Phase 3
0.7415	Intermediate Similarity	NPD411	Approved
0.7415	Intermediate Similarity	NPD3764	Approved
0.7413	Intermediate Similarity	NPD4749	Approved
0.7405	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4287	Approved
0.7394	Intermediate Similarity	NPD1201	Approved
0.7391	Intermediate Similarity	NPD2296	Approved
0.7386	Intermediate Similarity	NPD1652	Phase 2
0.7383	Intermediate Similarity	NPD447	Suspended
0.7383	Intermediate Similarity	NPD6355	Discontinued
0.7376	Intermediate Similarity	NPD17	Approved
0.7375	Intermediate Similarity	NPD6844	Discontinued
0.7372	Intermediate Similarity	NPD4662	Approved
0.7372	Intermediate Similarity	NPD4661	Approved
0.7365	Intermediate Similarity	NPD6233	Phase 2
0.7357	Intermediate Similarity	NPD1894	Discontinued
0.7349	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3027	Phase 3
0.7343	Intermediate Similarity	NPD1481	Phase 2
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.7318	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3142	Approved
0.7315	Intermediate Similarity	NPD3140	Approved
0.7314	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5889	Approved
0.7312	Intermediate Similarity	NPD5890	Approved
0.731	Intermediate Similarity	NPD1470	Approved
0.7308	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7458	Discontinued
0.729	Intermediate Similarity	NPD3887	Approved
0.729	Intermediate Similarity	NPD2354	Approved
0.7273	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD1535	Discovery
0.7268	Intermediate Similarity	NPD7584	Approved
0.7267	Intermediate Similarity	NPD7577	Discontinued
0.7261	Intermediate Similarity	NPD7447	Phase 1
0.7255	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1471	Phase 3
0.7241	Intermediate Similarity	NPD1876	Approved
0.7237	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7229	Phase 3
0.7209	Intermediate Similarity	NPD8313	Approved
0.7209	Intermediate Similarity	NPD8312	Approved
0.7208	Intermediate Similarity	NPD2424	Discontinued
0.7192	Intermediate Similarity	NPD1164	Approved
0.7186	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6280	Approved
0.716	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6279	Approved
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6585	Discontinued
0.7134	Intermediate Similarity	NPD7440	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