NPASS Compound

Structure

NPC196448 OpenBabel07101718242D 32 35 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 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 -3.4345 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 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 -3.4641 -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 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 C 0 0 2 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 0.8660 -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 -1.7321 0.0000 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 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 0.9781 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 -2.0000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 0.1691 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 12 1 0 0 0 0 2 12 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 26 1 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 17 2 0 0 0 0 13 3 1 6 0 0 0 13 25 1 0 0 0 0 13 31 1 0 0 0 0 14 27 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 16 21 1 0 0 0 0 16 22 2 0 0 0 0 17 22 1 0 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 18 24 2 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 19 25 1 0 0 0 0 20 28 1 0 0 0 0 21 29 2 0 0 0 0 22 32 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.2
Volume:	455.676
LogP:	5.788
LogD:	3.098
LogS:	-3.43
# Rotatable Bonds:	3
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	4.005
Fsp3:	0.423
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.833
MDCK Permeability:	1.2889361642010044e-05
Pgp-inhibitor:	0.532
Pgp-substrate:	0.314
Human Intestinal Absorption (HIA):	0.623
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	83.9333724975586%
Volume Distribution (VD):	1.49
Pgp-substrate:	13.5195951461792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.383
CYP1A2-substrate:	0.503
CYP2C19-inhibitor:	0.634
CYP2C19-substrate:	0.206
CYP2C9-inhibitor:	0.834
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.138
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.215
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	3.082
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.916
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.926
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.744
Carcinogencity:	0.346
Eye Corrosion:	0.003
Eye Irritation:	0.169
Respiratory Toxicity:	0.173

Download Data

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

Natural Product: NPC196448

Natural Product ID:	NPC196448
*Common Name:**	Scortechinone U
IUPAC Name:	(2R)-5,8-dihydroxy-10-(2-hydroxypropan-2-yl)-1,1,2-trimethyl-4-(3-methylbut-2-enyl)-2H-furo[2,3-c]xanthen-6-one
Synonyms:	Scortechinone U
Standard InCHIKey:	UZFQFSWIIKYKFR-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C26H30O6/c1-12(2)8-9-15-20(28)18-21(29)16-10-14(27)11-17(26(6,7)30)22(16)32-24(18)19-23(15)31-13(3)25(19,4)5/h8,10-11,13,27-28,30H,9H2,1-7H3/t13-/m1/s1
SMILES:	CC(=CCc1c(c2c(=O)c3cc(cc(c3oc2c2c1O[C@H](C)C2(C)C)C(C)(C)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486992
PubChem CID:	44559274
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003517] 2-prenylated xanthones

*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
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16038540]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	292000.0	nM	PMID[451738]

☑ 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 NPC196448 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	415
0.1-0.2	1640
0.2-0.3	3452
0.3-0.4	8535
0.4-0.5	10208
0.5-0.6	3922
0.6-0.7	5499
0.7-0.8	4809
0.8-0.85	2422
0.85-0.9	1603
0.9-0.95	186
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9548	High Similarity	NPC473313
0.9548	High Similarity	NPC329669
0.9548	High Similarity	NPC472278
0.94	High Similarity	NPC266499
0.9363	High Similarity	NPC473286
0.9338	High Similarity	NPC476185
0.9338	High Similarity	NPC321896
0.9333	High Similarity	NPC37135
0.9333	High Similarity	NPC186397
0.9329	High Similarity	NPC187282
0.9329	High Similarity	NPC290133
0.9329	High Similarity	NPC24136
0.9299	High Similarity	NPC18100
0.9276	High Similarity	NPC473131
0.9276	High Similarity	NPC470675
0.9272	High Similarity	NPC471114
0.9272	High Similarity	NPC317492
0.9272	High Similarity	NPC223988
0.9267	High Similarity	NPC10990
0.9267	High Similarity	NPC300988
0.925	High Similarity	NPC472276
0.9241	High Similarity	NPC472277
0.9236	High Similarity	NPC472402
0.9231	High Similarity	NPC471976
0.9216	High Similarity	NPC474843
0.9216	High Similarity	NPC473996
0.9216	High Similarity	NPC5871
0.9211	High Similarity	NPC37348
0.9211	High Similarity	NPC227122
0.9211	High Similarity	NPC472633
0.9211	High Similarity	NPC101957
0.9211	High Similarity	NPC120105
0.9205	High Similarity	NPC39195
0.9205	High Similarity	NPC168085
0.9187	High Similarity	NPC288813
0.9182	High Similarity	NPC170245
0.9177	High Similarity	NPC205265
0.9177	High Similarity	NPC273959
0.9177	High Similarity	NPC472281
0.9172	High Similarity	NPC30655
0.9172	High Similarity	NPC74854
0.9172	High Similarity	NPC45124
0.9172	High Similarity	NPC472275
0.9172	High Similarity	NPC3629
0.9167	High Similarity	NPC172770
0.9167	High Similarity	NPC185258
0.9156	High Similarity	NPC213608
0.9156	High Similarity	NPC1477
0.9156	High Similarity	NPC178964
0.9156	High Similarity	NPC280530
0.9156	High Similarity	NPC95842
0.915	High Similarity	NPC472580
0.915	High Similarity	NPC472636
0.9139	High Similarity	NPC308200
0.9133	High Similarity	NPC209040
0.9133	High Similarity	NPC470890
0.9128	High Similarity	NPC73028
0.9119	High Similarity	NPC326520
0.9119	High Similarity	NPC37183
0.9114	High Similarity	NPC81679
0.9108	High Similarity	NPC470810
0.9108	High Similarity	NPC476283
0.9103	High Similarity	NPC79053
0.9103	High Similarity	NPC65504
0.9097	High Similarity	NPC471116
0.9097	High Similarity	NPC113906
0.9091	High Similarity	NPC477957
0.9091	High Similarity	NPC476238
0.9091	High Similarity	NPC31627
0.9091	High Similarity	NPC327269
0.9085	High Similarity	NPC29777
0.9085	High Similarity	NPC471115
0.9085	High Similarity	NPC472421
0.9079	High Similarity	NPC145467
0.9073	High Similarity	NPC477955
0.9073	High Similarity	NPC472629
0.9073	High Similarity	NPC299011
0.9068	High Similarity	NPC152477
0.9067	High Similarity	NPC91560
0.9067	High Similarity	NPC316816
0.9067	High Similarity	NPC75049
0.9067	High Similarity	NPC164980
0.9067	High Similarity	NPC166138
0.9067	High Similarity	NPC18585
0.9067	High Similarity	NPC169591
0.9067	High Similarity	NPC175504
0.9067	High Similarity	NPC221432
0.9067	High Similarity	NPC68104
0.9067	High Similarity	NPC478086
0.9067	High Similarity	NPC106985
0.9067	High Similarity	NPC150408
0.9067	High Similarity	NPC149026
0.9067	High Similarity	NPC214166
0.9067	High Similarity	NPC39329
0.9067	High Similarity	NPC257097
0.9067	High Similarity	NPC143896
0.9067	High Similarity	NPC310130
0.9062	High Similarity	NPC128293
0.9062	High Similarity	NPC173292
0.9062	High Similarity	NPC277480
0.906	High Similarity	NPC17170
0.906	High Similarity	NPC96408
0.906	High Similarity	NPC156190
0.906	High Similarity	NPC279650
0.906	High Similarity	NPC258630
0.906	High Similarity	NPC166689
0.9057	High Similarity	NPC124038
0.9057	High Similarity	NPC475985
0.9057	High Similarity	NPC100849
0.9051	High Similarity	NPC187354
0.9051	High Similarity	NPC32694
0.9051	High Similarity	NPC474186
0.9045	High Similarity	NPC40583
0.9032	High Similarity	NPC472462
0.9032	High Similarity	NPC74924
0.9032	High Similarity	NPC183874
0.9032	High Similarity	NPC135522
0.9032	High Similarity	NPC469405
0.9026	High Similarity	NPC472423
0.9026	High Similarity	NPC471675
0.9026	High Similarity	NPC474744
0.9026	High Similarity	NPC244577
0.9026	High Similarity	NPC263384
0.9026	High Similarity	NPC305965
0.9026	High Similarity	NPC474772
0.9026	High Similarity	NPC232645
0.9026	High Similarity	NPC471676
0.9026	High Similarity	NPC472420
0.9026	High Similarity	NPC72958
0.9026	High Similarity	NPC472422
0.9026	High Similarity	NPC170169
0.902	High Similarity	NPC178202
0.902	High Similarity	NPC65775
0.902	High Similarity	NPC473016
0.902	High Similarity	NPC10027
0.9013	High Similarity	NPC296998
0.9013	High Similarity	NPC23728
0.9013	High Similarity	NPC473077
0.9013	High Similarity	NPC110303
0.9007	High Similarity	NPC311741
0.9007	High Similarity	NPC311144
0.9007	High Similarity	NPC117716
0.9007	High Similarity	NPC271288
0.9007	High Similarity	NPC197252
0.9007	High Similarity	NPC131568
0.9007	High Similarity	NPC224714
0.9007	High Similarity	NPC470674
0.9007	High Similarity	NPC470673
0.9007	High Similarity	NPC473015
0.9007	High Similarity	NPC234629
0.9007	High Similarity	NPC476055
0.9007	High Similarity	NPC184649
0.9007	High Similarity	NPC131579
0.9007	High Similarity	NPC473013
0.9007	High Similarity	NPC236766
0.9007	High Similarity	NPC87486
0.9007	High Similarity	NPC124780
0.9007	High Similarity	NPC303185
0.9	High Similarity	NPC148757
0.9	High Similarity	NPC76338
0.9	High Similarity	NPC66515
0.9	High Similarity	NPC316262
0.9	High Similarity	NPC306829
0.9	High Similarity	NPC169479
0.9	High Similarity	NPC166934
0.9	High Similarity	NPC300053
0.9	High Similarity	NPC159855
0.9	High Similarity	NPC32739
0.9	High Similarity	NPC227579
0.9	High Similarity	NPC76372
0.9	High Similarity	NPC37496
0.9	High Similarity	NPC265040
0.9	High Similarity	NPC144499
0.9	High Similarity	NPC324134
0.9	High Similarity	NPC40833
0.9	High Similarity	NPC64915
0.9	High Similarity	NPC220998
0.9	High Similarity	NPC223500
0.9	High Similarity	NPC182852
0.9	High Similarity	NPC125855
0.9	High Similarity	NPC328164
0.9	High Similarity	NPC10937
0.9	High Similarity	NPC147145
0.9	High Similarity	NPC324436
0.9	High Similarity	NPC1089
0.9	High Similarity	NPC167624
0.9	High Similarity	NPC194432
0.9	High Similarity	NPC166482
0.9	High Similarity	NPC108433
0.9	High Similarity	NPC78
0.9	High Similarity	NPC228504
0.9	High Similarity	NPC161506
0.9	High Similarity	NPC177354
0.9	High Similarity	NPC314653
0.9	High Similarity	NPC107572
0.9	High Similarity	NPC296917
0.8994	High Similarity	NPC470694
0.8993	High Similarity	NPC182421
0.8987	High Similarity	NPC475886
0.8987	High Similarity	NPC304839

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 NPC196448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	961
0.2-0.3	1645
0.3-0.4	2590
0.4-0.5	1987
0.5-0.6	1048
0.6-0.7	368
0.7-0.8	139
0.8-0.85	43
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.891	High Similarity	NPD2393	Clinical (unspecified phase)
0.8868	High Similarity	NPD5494	Approved
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.8733	High Similarity	NPD1549	Phase 2
0.8675	High Similarity	NPD2800	Approved
0.8671	High Similarity	NPD7819	Suspended
0.8667	High Similarity	NPD1550	Clinical (unspecified phase)
0.8667	High Similarity	NPD1552	Clinical (unspecified phase)
0.8616	High Similarity	NPD8443	Clinical (unspecified phase)
0.8608	High Similarity	NPD1934	Approved
0.8599	High Similarity	NPD4380	Phase 2
0.858	High Similarity	NPD6959	Discontinued
0.8553	High Similarity	NPD2801	Approved
0.8516	High Similarity	NPD7410	Clinical (unspecified phase)
0.8509	High Similarity	NPD7075	Discontinued
0.8477	Intermediate Similarity	NPD2796	Approved
0.8447	Intermediate Similarity	NPD3882	Suspended
0.8438	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7411	Suspended
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8397	Intermediate Similarity	NPD2534	Approved
0.8397	Intermediate Similarity	NPD2533	Approved
0.8397	Intermediate Similarity	NPD2532	Approved
0.8323	Intermediate Similarity	NPD3818	Discontinued
0.8282	Intermediate Similarity	NPD3749	Approved
0.8282	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1240	Approved
0.8235	Intermediate Similarity	NPD6559	Discontinued
0.8235	Intermediate Similarity	NPD2935	Discontinued
0.8221	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1511	Approved
0.8204	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6166	Phase 2
0.8204	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD5844	Phase 1
0.8158	Intermediate Similarity	NPD1607	Approved
0.8148	Intermediate Similarity	NPD6801	Discontinued
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.8117	Intermediate Similarity	NPD6100	Approved
0.8117	Intermediate Similarity	NPD6099	Approved
0.8113	Intermediate Similarity	NPD1512	Approved
0.811	Intermediate Similarity	NPD7768	Phase 2
0.8063	Intermediate Similarity	NPD920	Approved
0.8059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD5402	Approved
0.8025	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD1247	Approved
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD6799	Approved
0.7977	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6232	Discontinued
0.7962	Intermediate Similarity	NPD1243	Approved
0.7962	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7054	Approved
0.7949	Intermediate Similarity	NPD2344	Approved
0.7941	Intermediate Similarity	NPD7473	Discontinued
0.7939	Intermediate Similarity	NPD3817	Phase 2
0.7937	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD6651	Approved
0.7911	Intermediate Similarity	NPD3750	Approved
0.7907	Intermediate Similarity	NPD7472	Approved
0.7874	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5711	Approved
0.787	Intermediate Similarity	NPD5710	Approved
0.7861	Intermediate Similarity	NPD6797	Phase 2
0.7853	Intermediate Similarity	NPD3226	Approved
0.7834	Intermediate Similarity	NPD2346	Discontinued
0.7821	Intermediate Similarity	NPD2799	Discontinued
0.7821	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7251	Discontinued
0.7812	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7771	Intermediate Similarity	NPD7808	Phase 3
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7759	Intermediate Similarity	NPD5953	Discontinued
0.7759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2309	Approved
0.7746	Intermediate Similarity	NPD7286	Phase 2
0.7719	Intermediate Similarity	NPD3926	Phase 2
0.7716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8434	Phase 2
0.7692	Intermediate Similarity	NPD919	Approved
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7665	Intermediate Similarity	NPD5760	Phase 2
0.7665	Intermediate Similarity	NPD5761	Phase 2
0.7662	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7654	Intermediate Similarity	NPD7390	Discontinued
0.7622	Intermediate Similarity	NPD5403	Approved
0.7595	Intermediate Similarity	NPD3748	Approved
0.7586	Intermediate Similarity	NPD3751	Discontinued
0.7582	Intermediate Similarity	NPD2861	Phase 2
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD943	Approved
0.7558	Intermediate Similarity	NPD7229	Phase 3
0.7548	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD4363	Phase 3
0.7541	Intermediate Similarity	NPD4360	Phase 2
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4908	Phase 1
0.7527	Intermediate Similarity	NPD6778	Approved
0.7527	Intermediate Similarity	NPD6782	Approved
0.7527	Intermediate Similarity	NPD6777	Approved
0.7527	Intermediate Similarity	NPD6779	Approved
0.7527	Intermediate Similarity	NPD6781	Approved
0.7527	Intermediate Similarity	NPD6776	Approved
0.7527	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6844	Discontinued
0.75	Intermediate Similarity	NPD5401	Approved
0.7484	Intermediate Similarity	NPD4625	Phase 3
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7457	Intermediate Similarity	NPD3787	Discontinued
0.7444	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7425	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7416	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7435	Discontinued
0.7407	Intermediate Similarity	NPD7697	Approved
0.7407	Intermediate Similarity	NPD7696	Phase 3
0.7407	Intermediate Similarity	NPD7698	Approved
0.7405	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4361	Phase 2
0.7405	Intermediate Similarity	NPD230	Phase 1
0.7396	Intermediate Similarity	NPD37	Approved
0.7391	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6234	Discontinued
0.7368	Intermediate Similarity	NPD7871	Phase 2
0.7368	Intermediate Similarity	NPD7870	Phase 2
0.7368	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD4965	Approved
0.7349	Intermediate Similarity	NPD6273	Approved
0.7342	Intermediate Similarity	NPD1613	Approved
0.7342	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1203	Approved
0.7325	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3764	Approved
0.7322	Intermediate Similarity	NPD4287	Approved
0.7321	Intermediate Similarity	NPD7458	Discontinued
0.732	Intermediate Similarity	NPD4749	Approved
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7303	Intermediate Similarity	NPD1729	Discontinued
0.7301	Intermediate Similarity	NPD2654	Approved
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5124	Phase 1
0.7296	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2798	Approved
0.7288	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1471	Phase 3
0.7273	Intermediate Similarity	NPD6696	Suspended
0.7273	Intermediate Similarity	NPD2403	Approved
0.7263	Intermediate Similarity	NPD6823	Phase 2
0.7258	Intermediate Similarity	NPD6534	Approved
0.7258	Intermediate Similarity	NPD6535	Approved
0.7255	Intermediate Similarity	NPD3972	Approved
0.7254	Intermediate Similarity	NPD7701	Phase 2
0.7244	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2424	Discontinued
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1470	Approved
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.7215	Intermediate Similarity	NPD3268	Approved
0.7209	Intermediate Similarity	NPD2296	Approved
0.7202	Intermediate Similarity	NPD7584	Approved
0.72	Intermediate Similarity	NPD7199	Phase 2
0.7197	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7228	Approved
0.7188	Intermediate Similarity	NPD447	Suspended
0.7184	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7874	Approved
0.7179	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD7699	Phase 2
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD7801	Approved
0.7127	Intermediate Similarity	NPD6104	Discontinued
0.7126	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5404	Approved
0.7117	Intermediate Similarity	NPD5406	Approved
0.7117	Intermediate Similarity	NPD5405	Approved
0.7117	Intermediate Similarity	NPD5408	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