NPASS Compound

Structure

NPC475970 OpenBabel07101718202D 35 39 0 0 1 0 0 0 0 0999 V2000 6.2053 1.6714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9454 -0.8386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8193 -0.0609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5439 -0.7133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7092 -2.4638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0181 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1420 -1.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3508 1.0688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 0.4164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4235 0.7675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1754 0.0325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2655 -2.6665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7246 -2.6024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3118 -2.4638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5689 -2.1149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2217 -0.1702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8969 0.4032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0026 0.7177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2208 -0.1862 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6629 -0.8119 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9179 -1.9419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1198 -2.1149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9273 0.3013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7272 0.0653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6166 -1.0146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0105 -1.5365 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2935 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5689 -1.1399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1198 -1.1399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7246 -0.6524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8716 -2.1446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 -3.0899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6545 0.3666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5245 -0.8884 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 18 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 18 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 24 1 0 0 0 0 19 2 1 1 0 0 0 19 27 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 6 0 0 0 21 25 1 0 0 0 0 21 31 1 6 0 0 0 22 29 1 0 0 0 0 22 32 2 0 0 0 0 23 30 1 1 0 0 0 23 35 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 29 1 1 0 0 0 27 28 1 6 0 0 0 28 30 1 6 0 0 0 29 30 1 6 0 0 0 30 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.32
Volume:	518.059
LogP:	3.829
LogD:	2.668
LogS:	-4.373
# Rotatable Bonds:	4
TPSA:	87.13
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.394
Synthetic Accessibility Score:	6.257
Fsp3:	0.8
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:	-5.366
MDCK Permeability:	2.7239178962190636e-05
Pgp-inhibitor:	0.296
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985
Plasma Protein Binding (PPB):	92.21867370605469%
Volume Distribution (VD):	0.531
Pgp-substrate:	7.408934116363525%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.618
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.9

ADMET: Excretion

Clearance (CL):	5.444
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.222
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.905
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.389
Carcinogencity:	0.739
Eye Corrosion:	0.004
Eye Irritation:	0.043
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC475970

Natural Product ID:	NPC475970
*Common Name:**	14Beta,15Beta-Epoxy-3Beta-Hydroxy-9-Oxo-11(10->8)-Abeolanosta-22-Cis,24-Trans-Dien-26-Oic Acid
IUPAC Name:	(2E,4Z,6R)-6-[(1'aR,3R,3'R,3aS,3'aR,6S,7aR,7'aS)-6-hydroxy-3',3a,3'a,7,7-pentamethyl-6'-oxospiro[1,2,4,5,6,7a-hexahydroindene-3,7'-1a,2,4,5-tetrahydroindeno[3,3a-b]oxirene]-3'-yl]-2-methylhepta-2,4-dienoic acid
Synonyms:
Standard InCHIKey:	UONZCNGOTPYRMX-LBUWXADRSA-N
Standard InCHI:	InChI=1S/C30H44O5/c1-18(24(33)34)9-8-10-19(2)27(6)17-23-30(35-23)28(27,7)15-13-22(32)29(30)16-11-20-25(3,4)21(31)12-14-26(20,29)5/h8-10,19-21,23,31H,11-17H2,1-7H3,(H,33,34)/b10-8-,18-9+/t19-,20+,21+,23-,26+,27-,28-,29-,30+/m1/s1
SMILES:	CC(C=CC=C(C)C(=O)O)C1(CC2C3(C1(CCC(=O)C34CCC5C4(CCC(C5(C)C)O)C)C)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519885
PubChem CID:	21574221
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	barks	n.a.	n.a.	PMID[15620248]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25515	Garcinia speciosa	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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	69600.0	nM	PMID[469895]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	70300.0	nM	PMID[469895]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	95700.0	nM	PMID[469895]

☑ 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 NPC475970 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	221
0.1-0.2	1133
0.2-0.3	4197
0.3-0.4	8908
0.4-0.5	13005
0.5-0.6	7744
0.6-0.7	5743
0.7-0.8	1653
0.8-0.85	81
0.85-0.9	9
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC475941
0.9709	High Similarity	NPC474901
0.8679	High Similarity	NPC72151
0.8673	High Similarity	NPC329736
0.8667	High Similarity	NPC282524
0.8596	High Similarity	NPC61520
0.8585	High Similarity	NPC320447
0.8496	Intermediate Similarity	NPC270929
0.8491	Intermediate Similarity	NPC224720
0.8491	Intermediate Similarity	NPC476240
0.8491	Intermediate Similarity	NPC476223
0.8482	Intermediate Similarity	NPC122056
0.8462	Intermediate Similarity	NPC250757
0.8462	Intermediate Similarity	NPC301534
0.844	Intermediate Similarity	NPC473284
0.8435	Intermediate Similarity	NPC264954
0.8403	Intermediate Similarity	NPC473253
0.8396	Intermediate Similarity	NPC266955
0.8396	Intermediate Similarity	NPC476274
0.8378	Intermediate Similarity	NPC179642
0.8362	Intermediate Similarity	NPC476962
0.8362	Intermediate Similarity	NPC474370
0.8333	Intermediate Similarity	NPC473283
0.8333	Intermediate Similarity	NPC475526
0.8333	Intermediate Similarity	NPC475050
0.8333	Intermediate Similarity	NPC329345
0.8318	Intermediate Similarity	NPC115899
0.8304	Intermediate Similarity	NPC474315
0.8302	Intermediate Similarity	NPC57079
0.8302	Intermediate Similarity	NPC108368
0.8288	Intermediate Similarity	NPC10064
0.8288	Intermediate Similarity	NPC170221
0.8286	Intermediate Similarity	NPC471153
0.8273	Intermediate Similarity	NPC220974
0.8269	Intermediate Similarity	NPC299100
0.8264	Intermediate Similarity	NPC470880
0.8261	Intermediate Similarity	NPC471854
0.8261	Intermediate Similarity	NPC286528
0.8261	Intermediate Similarity	NPC20302
0.8261	Intermediate Similarity	NPC470492
0.8261	Intermediate Similarity	NPC167606
0.8261	Intermediate Similarity	NPC140055
0.8241	Intermediate Similarity	NPC136289
0.8235	Intermediate Similarity	NPC8369
0.823	Intermediate Similarity	NPC476163
0.8224	Intermediate Similarity	NPC35751
0.8224	Intermediate Similarity	NPC477521
0.822	Intermediate Similarity	NPC153700
0.822	Intermediate Similarity	NPC88326
0.8214	Intermediate Similarity	NPC6206
0.8214	Intermediate Similarity	NPC76084
0.8198	Intermediate Similarity	NPC102843
0.819	Intermediate Similarity	NPC88310
0.819	Intermediate Similarity	NPC180950
0.819	Intermediate Similarity	NPC709
0.819	Intermediate Similarity	NPC50774
0.8174	Intermediate Similarity	NPC266728
0.8174	Intermediate Similarity	NPC49492
0.8165	Intermediate Similarity	NPC476237
0.8158	Intermediate Similarity	NPC73050
0.8158	Intermediate Similarity	NPC962
0.8158	Intermediate Similarity	NPC250109
0.8151	Intermediate Similarity	NPC469789
0.8151	Intermediate Similarity	NPC204812
0.8148	Intermediate Similarity	NPC118174
0.8148	Intermediate Similarity	NPC81530
0.8125	Intermediate Similarity	NPC475065
0.812	Intermediate Similarity	NPC476960
0.8108	Intermediate Similarity	NPC330011
0.8108	Intermediate Similarity	NPC44063
0.8108	Intermediate Similarity	NPC329048
0.8103	Intermediate Similarity	NPC183580
0.8103	Intermediate Similarity	NPC312824
0.8103	Intermediate Similarity	NPC474518
0.8103	Intermediate Similarity	NPC243065
0.8103	Intermediate Similarity	NPC239273
0.8103	Intermediate Similarity	NPC470493
0.8099	Intermediate Similarity	NPC473265
0.8099	Intermediate Similarity	NPC287423
0.8099	Intermediate Similarity	NPC470882
0.8087	Intermediate Similarity	NPC147912
0.8087	Intermediate Similarity	NPC67259
0.8083	Intermediate Similarity	NPC172154
0.8083	Intermediate Similarity	NPC81736
0.8083	Intermediate Similarity	NPC241456
0.8083	Intermediate Similarity	NPC32868
0.8083	Intermediate Similarity	NPC8374
0.8073	Intermediate Similarity	NPC155332
0.8073	Intermediate Similarity	NPC32577
0.8073	Intermediate Similarity	NPC114540
0.8073	Intermediate Similarity	NPC477915
0.807	Intermediate Similarity	NPC71348
0.807	Intermediate Similarity	NPC100267
0.807	Intermediate Similarity	NPC475524
0.807	Intermediate Similarity	NPC69291
0.8065	Intermediate Similarity	NPC469674
0.8056	Intermediate Similarity	NPC112167
0.8053	Intermediate Similarity	NPC16270
0.8051	Intermediate Similarity	NPC184555
0.8037	Intermediate Similarity	NPC2049
0.8037	Intermediate Similarity	NPC475894
0.8037	Intermediate Similarity	NPC474343
0.8037	Intermediate Similarity	NPC253826
0.8037	Intermediate Similarity	NPC107243
0.8036	Intermediate Similarity	NPC475418
0.8036	Intermediate Similarity	NPC220155
0.8036	Intermediate Similarity	NPC318363
0.8036	Intermediate Similarity	NPC473482
0.8034	Intermediate Similarity	NPC470420
0.8034	Intermediate Similarity	NPC257457
0.8034	Intermediate Similarity	NPC311554
0.8033	Intermediate Similarity	NPC473888
0.8018	Intermediate Similarity	NPC266570
0.8017	Intermediate Similarity	NPC293112
0.8017	Intermediate Similarity	NPC72772
0.8017	Intermediate Similarity	NPC469794
0.8017	Intermediate Similarity	NPC148458
0.8	Intermediate Similarity	NPC36321
0.8	Intermediate Similarity	NPC55602
0.8	Intermediate Similarity	NPC470310
0.8	Intermediate Similarity	NPC11895
0.8	Intermediate Similarity	NPC9848
0.8	Intermediate Similarity	NPC317210
0.8	Intermediate Similarity	NPC52634
0.8	Intermediate Similarity	NPC312017
0.8	Intermediate Similarity	NPC112009
0.8	Intermediate Similarity	NPC236390
0.8	Intermediate Similarity	NPC311612
0.7983	Intermediate Similarity	NPC470878
0.7983	Intermediate Similarity	NPC473256
0.7983	Intermediate Similarity	NPC67569
0.7982	Intermediate Similarity	NPC475099
0.7982	Intermediate Similarity	NPC470960
0.7982	Intermediate Similarity	NPC99411
0.7982	Intermediate Similarity	NPC472924
0.7981	Intermediate Similarity	NPC474842
0.7981	Intermediate Similarity	NPC475965
0.7967	Intermediate Similarity	NPC221414
0.7966	Intermediate Similarity	NPC473203
0.7965	Intermediate Similarity	NPC2766
0.7965	Intermediate Similarity	NPC214644
0.7963	Intermediate Similarity	NPC166745
0.7963	Intermediate Similarity	NPC103051
0.7963	Intermediate Similarity	NPC197386
0.7963	Intermediate Similarity	NPC316598
0.7963	Intermediate Similarity	NPC48647
0.7963	Intermediate Similarity	NPC235464
0.7963	Intermediate Similarity	NPC186810
0.7949	Intermediate Similarity	NPC470959
0.7949	Intermediate Similarity	NPC476965
0.7946	Intermediate Similarity	NPC470952
0.7946	Intermediate Similarity	NPC43063
0.7946	Intermediate Similarity	NPC472925
0.7946	Intermediate Similarity	NPC475294
0.7946	Intermediate Similarity	NPC79298
0.7946	Intermediate Similarity	NPC185
0.7944	Intermediate Similarity	NPC122324
0.7944	Intermediate Similarity	NPC242848
0.7944	Intermediate Similarity	NPC106425
0.7944	Intermediate Similarity	NPC29152
0.7944	Intermediate Similarity	NPC249954
0.7944	Intermediate Similarity	NPC151725
0.7931	Intermediate Similarity	NPC238667
0.7931	Intermediate Similarity	NPC284915
0.7928	Intermediate Similarity	NPC209502
0.7928	Intermediate Similarity	NPC118911
0.7928	Intermediate Similarity	NPC201763
0.7928	Intermediate Similarity	NPC309190
0.7928	Intermediate Similarity	NPC235889
0.7928	Intermediate Similarity	NPC204833
0.7925	Intermediate Similarity	NPC473435
0.7925	Intermediate Similarity	NPC473431
0.7925	Intermediate Similarity	NPC471078
0.7925	Intermediate Similarity	NPC473280
0.7925	Intermediate Similarity	NPC474690
0.7917	Intermediate Similarity	NPC23786
0.7917	Intermediate Similarity	NPC470265
0.7917	Intermediate Similarity	NPC269642
0.7917	Intermediate Similarity	NPC470419
0.7917	Intermediate Similarity	NPC170538
0.7913	Intermediate Similarity	NPC207251
0.7913	Intermediate Similarity	NPC147180
0.7913	Intermediate Similarity	NPC264634
0.7913	Intermediate Similarity	NPC285956
0.7909	Intermediate Similarity	NPC195290
0.7909	Intermediate Similarity	NPC473424
0.7909	Intermediate Similarity	NPC204450
0.7909	Intermediate Similarity	NPC87351
0.7905	Intermediate Similarity	NPC473986
0.7905	Intermediate Similarity	NPC474018
0.7899	Intermediate Similarity	NPC109973
0.7895	Intermediate Similarity	NPC197428
0.7895	Intermediate Similarity	NPC470496
0.789	Intermediate Similarity	NPC306856
0.789	Intermediate Similarity	NPC201406
0.789	Intermediate Similarity	NPC470074
0.789	Intermediate Similarity	NPC287833
0.789	Intermediate Similarity	NPC117685
0.789	Intermediate Similarity	NPC476303
0.789	Intermediate Similarity	NPC154072

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 NPC475970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1298
0.2-0.3	3701
0.3-0.4	2662
0.4-0.5	783
0.5-0.6	226
0.6-0.7	179
0.7-0.8	110
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD7115	Discovery
0.8198	Intermediate Similarity	NPD6899	Approved
0.8198	Intermediate Similarity	NPD7320	Approved
0.8198	Intermediate Similarity	NPD6881	Approved
0.8142	Intermediate Similarity	NPD6649	Approved
0.8142	Intermediate Similarity	NPD6650	Approved
0.8108	Intermediate Similarity	NPD5697	Approved
0.8053	Intermediate Similarity	NPD6883	Approved
0.8053	Intermediate Similarity	NPD7102	Approved
0.8053	Intermediate Similarity	NPD7290	Approved
0.8036	Intermediate Similarity	NPD6011	Approved
0.8018	Intermediate Similarity	NPD7128	Approved
0.8018	Intermediate Similarity	NPD6675	Approved
0.8018	Intermediate Similarity	NPD5739	Approved
0.8018	Intermediate Similarity	NPD6402	Approved
0.7982	Intermediate Similarity	NPD6617	Approved
0.7982	Intermediate Similarity	NPD8130	Phase 1
0.7982	Intermediate Similarity	NPD6847	Approved
0.7982	Intermediate Similarity	NPD6869	Approved
0.7965	Intermediate Similarity	NPD6014	Approved
0.7965	Intermediate Similarity	NPD6373	Approved
0.7965	Intermediate Similarity	NPD6372	Approved
0.7965	Intermediate Similarity	NPD6013	Approved
0.7965	Intermediate Similarity	NPD6012	Approved
0.7913	Intermediate Similarity	NPD6882	Approved
0.7913	Intermediate Similarity	NPD8297	Approved
0.7909	Intermediate Similarity	NPD5211	Phase 2
0.7857	Intermediate Similarity	NPD6008	Approved
0.7788	Intermediate Similarity	NPD5701	Approved
0.7768	Intermediate Similarity	NPD5141	Approved
0.7736	Intermediate Similarity	NPD6079	Approved
0.7727	Intermediate Similarity	NPD5285	Approved
0.7727	Intermediate Similarity	NPD5286	Approved
0.7727	Intermediate Similarity	NPD4696	Approved
0.7685	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7078	Approved
0.7658	Intermediate Similarity	NPD5223	Approved
0.7642	Intermediate Similarity	NPD7492	Approved
0.7642	Intermediate Similarity	NPD5785	Approved
0.7603	Intermediate Similarity	NPD6319	Approved
0.7603	Intermediate Similarity	NPD6054	Approved
0.7589	Intermediate Similarity	NPD5226	Approved
0.7589	Intermediate Similarity	NPD5225	Approved
0.7589	Intermediate Similarity	NPD4633	Approved
0.7589	Intermediate Similarity	NPD5224	Approved
0.7583	Intermediate Similarity	NPD6335	Approved
0.7581	Intermediate Similarity	NPD6616	Approved
0.7568	Intermediate Similarity	NPD7640	Approved
0.7568	Intermediate Similarity	NPD7639	Approved
0.7547	Intermediate Similarity	NPD5328	Approved
0.7545	Intermediate Similarity	NPD6083	Phase 2
0.7545	Intermediate Similarity	NPD4755	Approved
0.7545	Intermediate Similarity	NPD6084	Phase 2
0.7542	Intermediate Similarity	NPD4632	Approved
0.7541	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD5175	Approved
0.7522	Intermediate Similarity	NPD5174	Approved
0.7521	Intermediate Similarity	NPD7101	Approved
0.7521	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD6317	Approved
0.75	Intermediate Similarity	NPD5363	Approved
0.748	Intermediate Similarity	NPD6370	Approved
0.7477	Intermediate Similarity	NPD4225	Approved
0.7477	Intermediate Similarity	NPD7638	Approved
0.746	Intermediate Similarity	NPD7736	Approved
0.7455	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5222	Approved
0.7455	Intermediate Similarity	NPD5221	Approved
0.7453	Intermediate Similarity	NPD6903	Approved
0.7438	Intermediate Similarity	NPD6314	Approved
0.7438	Intermediate Similarity	NPD6313	Approved
0.7436	Intermediate Similarity	NPD4634	Approved
0.7429	Intermediate Similarity	NPD5786	Approved
0.7419	Intermediate Similarity	NPD7604	Phase 2
0.7417	Intermediate Similarity	NPD6274	Approved
0.7411	Intermediate Similarity	NPD4700	Approved
0.7407	Intermediate Similarity	NPD5284	Approved
0.7407	Intermediate Similarity	NPD5281	Approved
0.7407	Intermediate Similarity	NPD7637	Suspended
0.7398	Intermediate Similarity	NPD6016	Approved
0.7398	Intermediate Similarity	NPD6015	Approved
0.7387	Intermediate Similarity	NPD5173	Approved
0.7355	Intermediate Similarity	NPD6009	Approved
0.7339	Intermediate Similarity	NPD4202	Approved
0.7339	Intermediate Similarity	NPD5778	Approved
0.7339	Intermediate Similarity	NPD6399	Phase 3
0.7339	Intermediate Similarity	NPD5988	Approved
0.7339	Intermediate Similarity	NPD5779	Approved
0.7321	Intermediate Similarity	NPD5696	Approved
0.7317	Intermediate Similarity	NPD6059	Approved
0.7315	Intermediate Similarity	NPD5207	Approved
0.7297	Intermediate Similarity	NPD4697	Phase 3
0.7273	Intermediate Similarity	NPD6001	Approved
0.7273	Intermediate Similarity	NPD6868	Approved
0.7266	Intermediate Similarity	NPD7319	Approved
0.7265	Intermediate Similarity	NPD4729	Approved
0.7265	Intermediate Similarity	NPD4730	Approved
0.7264	Intermediate Similarity	NPD3618	Phase 1
0.7264	Intermediate Similarity	NPD6409	Approved
0.7264	Intermediate Similarity	NPD5330	Approved
0.7264	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6684	Approved
0.7264	Intermediate Similarity	NPD7334	Approved
0.7264	Intermediate Similarity	NPD7521	Approved
0.7264	Intermediate Similarity	NPD7146	Approved
0.7258	Intermediate Similarity	NPD5983	Phase 2
0.7248	Intermediate Similarity	NPD6411	Approved
0.7244	Intermediate Similarity	NPD8293	Discontinued
0.7217	Intermediate Similarity	NPD4754	Approved
0.7212	Intermediate Similarity	NPD4269	Approved
0.7212	Intermediate Similarity	NPD4270	Approved
0.7207	Intermediate Similarity	NPD5210	Approved
0.7207	Intermediate Similarity	NPD4629	Approved
0.7207	Intermediate Similarity	NPD5695	Phase 3
0.7165	Intermediate Similarity	NPD6336	Discontinued
0.7165	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5135	Approved
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD5250	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6908	Approved
0.712	Intermediate Similarity	NPD6909	Approved
0.7119	Intermediate Similarity	NPD5128	Approved
0.7117	Intermediate Similarity	NPD7748	Approved
0.7115	Intermediate Similarity	NPD5369	Approved
0.7094	Intermediate Similarity	NPD4767	Approved
0.7094	Intermediate Similarity	NPD4768	Approved
0.7091	Intermediate Similarity	NPD7515	Phase 2
0.7091	Intermediate Similarity	NPD5694	Approved
0.7091	Intermediate Similarity	NPD6050	Approved
0.7083	Intermediate Similarity	NPD5215	Approved
0.7083	Intermediate Similarity	NPD5216	Approved
0.7083	Intermediate Similarity	NPD5217	Approved
0.7083	Intermediate Similarity	NPD5127	Approved
0.708	Intermediate Similarity	NPD7902	Approved
0.7075	Intermediate Similarity	NPD3665	Phase 1
0.7075	Intermediate Similarity	NPD3666	Approved
0.7075	Intermediate Similarity	NPD3133	Approved
0.7064	Intermediate Similarity	NPD6101	Approved
0.7064	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6673	Approved
0.7064	Intermediate Similarity	NPD4753	Phase 2
0.7064	Intermediate Similarity	NPD6080	Approved
0.7064	Intermediate Similarity	NPD6904	Approved
0.7054	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3573	Approved
0.7025	Intermediate Similarity	NPD6053	Discontinued
0.7019	Intermediate Similarity	NPD4252	Approved
0.7	Intermediate Similarity	NPD5692	Phase 3
0.7	Intermediate Similarity	NPD6371	Approved
0.699	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7632	Discontinued
0.6972	Remote Similarity	NPD6672	Approved
0.6972	Remote Similarity	NPD5737	Approved
0.6944	Remote Similarity	NPD5279	Phase 3
0.6937	Remote Similarity	NPD5693	Phase 1
0.6937	Remote Similarity	NPD8035	Phase 2
0.6937	Remote Similarity	NPD8034	Phase 2
0.6923	Remote Similarity	NPD6033	Approved
0.6916	Remote Similarity	NPD4786	Approved
0.6911	Remote Similarity	NPD5167	Approved
0.6887	Remote Similarity	NPD6435	Approved
0.6887	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4221	Approved
0.6887	Remote Similarity	NPD4223	Phase 3
0.6852	Remote Similarity	NPD1694	Approved
0.6852	Remote Similarity	NPD5329	Approved
0.6852	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5168	Approved
0.6822	Remote Similarity	NPD5332	Approved
0.6822	Remote Similarity	NPD4788	Approved
0.6822	Remote Similarity	NPD5331	Approved
0.6818	Remote Similarity	NPD5208	Approved
0.6814	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD4790	Discontinued
0.6789	Remote Similarity	NPD6098	Approved
0.6789	Remote Similarity	NPD4694	Approved
0.6789	Remote Similarity	NPD5280	Approved
0.6789	Remote Similarity	NPD5690	Phase 2
0.6759	Remote Similarity	NPD4197	Approved
0.6729	Remote Similarity	NPD5209	Approved
0.6729	Remote Similarity	NPD3667	Approved
0.6719	Remote Similarity	NPD7503	Approved
0.6715	Remote Similarity	NPD6334	Approved
0.6715	Remote Similarity	NPD6333	Approved
0.6698	Remote Similarity	NPD5368	Approved
0.6697	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6695	Phase 3
0.6639	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6052	Approved
0.6638	Remote Similarity	NPD5959	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