NPASS Compound

Structure

NPC471068 OpenBabel07101719152D 33 34 0 0 1 0 0 0 0 0999 V2000 -14.7224 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1603 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -6.0622 -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 -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 -8.6603 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5263 -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 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 -9.5263 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 20 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 31 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 21 23 2 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 15 1 1 0 0 0 24 27 1 0 0 0 0 24 33 1 0 0 0 0 25 28 2 0 0 0 0 25 33 1 0 0 0 0 26 29 2 0 0 0 0 26 32 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.27
Volume:	492.721
LogP:	5.855
LogD:	4.425
LogS:	-5.115
# Rotatable Bonds:	15
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	3.25
Fsp3:	0.556
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:	-4.684
MDCK Permeability:	3.497056241030805e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	98.58484649658203%
Volume Distribution (VD):	0.436
Pgp-substrate:	1.850062370300293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.254
CYP1A2-substrate:	0.525
CYP2C19-inhibitor:	0.713
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.508
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.527
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.628
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	6.695
Half-life (T1/2):	0.319

ADMET: Toxicity

hERG Blockers:	0.153
Human Hepatotoxicity (H-HT):	0.607
Drug-inuced Liver Injury (DILI):	0.815
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.681
Skin Sensitization:	0.924
Carcinogencity:	0.105
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC471068

Natural Product ID:	NPC471068
*Common Name:**	R-(+)-Marmin-6'-Octanoate
IUPAC Name:	[(E,3R)-2-hydroxy-2,6-dimethyl-8-(2-oxochromen-7-yl)oxyoct-6-en-3-yl] octanoate
Synonyms:	R-(+)-Marmin-6'-octanoate
Standard InCHIKey:	ZEGHXNCKKXBSHJ-BKWQBPKISA-N
Standard InCHI:	InChI=1S/C27H38O6/c1-5-6-7-8-9-10-25(28)33-24(27(3,4)30)15-11-20(2)17-18-31-22-14-12-21-13-16-26(29)32-23(21)19-22/h12-14,16-17,19,24,30H,5-11,15,18H2,1-4H3/b20-17+/t24-/m1/s1
SMILES:	CCCCCCCC(=O)O[C@@H](C(O)(C)C)CC/C(=C/COc1ccc2c(c1)oc(=O)cc2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346914
PubChem CID:	71584574
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18760601]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[21875114]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434131]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26247834]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30579794]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	3

Activity Type	# Activity
Others	3
PROTEIN COMPLEX	100

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	39.0	%	PMID[541987]
NPT2	Others	Unspecified		Inhibition	=	28.0	%	PMID[541987]
NPT2	Others	Unspecified		Inhibition	=	30.0	%	PMID[541987]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	=	3710.0	nM	PMID[541987]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	=	3080.0	nM	PMID[541987]

☑ 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 NPC471068 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	344
0.1-0.2	1415
0.2-0.3	3673
0.3-0.4	8452
0.4-0.5	10217
0.5-0.6	4118
0.6-0.7	6143
0.7-0.8	5203
0.8-0.85	2349
0.85-0.9	611
0.9-0.95	156
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471069
0.9924	High Similarity	NPC471071
0.9924	High Similarity	NPC471072
0.9924	High Similarity	NPC471070
0.9394	High Similarity	NPC469449
0.9389	High Similarity	NPC272650
0.9389	High Similarity	NPC29734
0.9389	High Similarity	NPC267336
0.9313	High Similarity	NPC113098
0.9259	High Similarity	NPC155963
0.9191	High Similarity	NPC151946
0.9124	High Similarity	NPC312881
0.9111	High Similarity	NPC472525
0.9058	High Similarity	NPC287286
0.9058	High Similarity	NPC195357
0.9058	High Similarity	NPC152771
0.9044	High Similarity	NPC38099
0.9044	High Similarity	NPC26954
0.9037	High Similarity	NPC213173
0.9037	High Similarity	NPC224475
0.9037	High Similarity	NPC98179
0.9037	High Similarity	NPC253574
0.9037	High Similarity	NPC180716
0.9037	High Similarity	NPC62366
0.9015	High Similarity	NPC469453
0.8978	High Similarity	NPC232246
0.8978	High Similarity	NPC153818
0.8971	High Similarity	NPC61499
0.8971	High Similarity	NPC33986
0.8963	High Similarity	NPC7526
0.8963	High Similarity	NPC222036
0.8939	High Similarity	NPC121740
0.8939	High Similarity	NPC258567
0.8939	High Similarity	NPC224774
0.8921	High Similarity	NPC155552
0.8913	High Similarity	NPC211110
0.8913	High Similarity	NPC279573
0.8905	High Similarity	NPC78746
0.8905	High Similarity	NPC283331
0.8905	High Similarity	NPC283019
0.8905	High Similarity	NPC128529
0.8905	High Similarity	NPC471630
0.8905	High Similarity	NPC224543
0.8905	High Similarity	NPC160727
0.8905	High Similarity	NPC476455
0.8905	High Similarity	NPC55615
0.8905	High Similarity	NPC177281
0.8905	High Similarity	NPC149320
0.8905	High Similarity	NPC188380
0.8897	High Similarity	NPC198381
0.8897	High Similarity	NPC74655
0.8897	High Similarity	NPC267412
0.8897	High Similarity	NPC100986
0.8897	High Similarity	NPC84894
0.8897	High Similarity	NPC50896
0.8897	High Similarity	NPC47163
0.8897	High Similarity	NPC55149
0.8897	High Similarity	NPC195343
0.8897	High Similarity	NPC319859
0.8897	High Similarity	NPC164269
0.8897	High Similarity	NPC18804
0.8897	High Similarity	NPC326600
0.8897	High Similarity	NPC307412
0.8897	High Similarity	NPC204353
0.8897	High Similarity	NPC260265
0.8897	High Similarity	NPC287182
0.8897	High Similarity	NPC127888
0.8897	High Similarity	NPC166672
0.8889	High Similarity	NPC14248
0.8889	High Similarity	NPC103116
0.8872	High Similarity	NPC185066
0.8865	High Similarity	NPC471824
0.8849	High Similarity	NPC71903
0.8841	High Similarity	NPC294456
0.8841	High Similarity	NPC184861
0.8841	High Similarity	NPC225106
0.8841	High Similarity	NPC212124
0.8841	High Similarity	NPC281014
0.8832	High Similarity	NPC472424
0.8832	High Similarity	NPC281241
0.8832	High Similarity	NPC471909
0.8832	High Similarity	NPC86892
0.8832	High Similarity	NPC471625
0.8824	High Similarity	NPC31849
0.8824	High Similarity	NPC318400
0.8824	High Similarity	NPC207002
0.8824	High Similarity	NPC167111
0.8824	High Similarity	NPC471910
0.8824	High Similarity	NPC133956
0.8824	High Similarity	NPC296624
0.8806	High Similarity	NPC474289
0.8794	High Similarity	NPC229916
0.8786	High Similarity	NPC170812
0.8786	High Similarity	NPC310370
0.8786	High Similarity	NPC183642
0.8777	High Similarity	NPC327612
0.8777	High Similarity	NPC307883
0.8777	High Similarity	NPC73078
0.8777	High Similarity	NPC148738
0.8777	High Similarity	NPC319870
0.875	High Similarity	NPC175159
0.8731	High Similarity	NPC472519
0.8712	High Similarity	NPC201667
0.8712	High Similarity	NPC73413
0.8696	High Similarity	NPC229128
0.8696	High Similarity	NPC469675
0.8692	High Similarity	NPC180006
0.8692	High Similarity	NPC235190
0.8692	High Similarity	NPC163200
0.8686	High Similarity	NPC55147
0.8686	High Similarity	NPC54503
0.8686	High Similarity	NPC2363
0.8676	High Similarity	NPC472517
0.8671	High Similarity	NPC85624
0.8671	High Similarity	NPC469701
0.8671	High Similarity	NPC295696
0.8667	High Similarity	NPC168710
0.8657	High Similarity	NPC243688
0.8652	High Similarity	NPC300611
0.8643	High Similarity	NPC221046
0.8636	High Similarity	NPC273772
0.8636	High Similarity	NPC472518
0.8636	High Similarity	NPC109675
0.8633	High Similarity	NPC246177
0.8633	High Similarity	NPC317045
0.8633	High Similarity	NPC223616
0.863	High Similarity	NPC107197
0.8613	High Similarity	NPC194277
0.8611	High Similarity	NPC205361
0.8603	High Similarity	NPC80170
0.8592	High Similarity	NPC184053
0.8581	High Similarity	NPC256141
0.8571	High Similarity	NPC131198
0.8571	High Similarity	NPC27671
0.8571	High Similarity	NPC180351
0.8562	High Similarity	NPC146388
0.8561	High Similarity	NPC96286
0.8561	High Similarity	NPC248429
0.8552	High Similarity	NPC471764
0.8552	High Similarity	NPC87950
0.8552	High Similarity	NPC296377
0.8551	High Similarity	NPC163557
0.8542	High Similarity	NPC71739
0.8542	High Similarity	NPC76657
0.8538	High Similarity	NPC298796
0.8538	High Similarity	NPC281356
0.8531	High Similarity	NPC119640
0.8531	High Similarity	NPC183646
0.8521	High Similarity	NPC215512
0.8521	High Similarity	NPC476442
0.8511	High Similarity	NPC253616
0.8511	High Similarity	NPC332594
0.8507	High Similarity	NPC93219
0.8507	High Similarity	NPC471828
0.8507	High Similarity	NPC244495
0.8507	High Similarity	NPC471827
0.8503	High Similarity	NPC100818
0.8503	High Similarity	NPC146014
0.85	High Similarity	NPC103409
0.8496	Intermediate Similarity	NPC315807
0.8493	Intermediate Similarity	NPC14875
0.8493	Intermediate Similarity	NPC139839
0.8493	Intermediate Similarity	NPC169510
0.8485	Intermediate Similarity	NPC187868
0.8485	Intermediate Similarity	NPC52247
0.8483	Intermediate Similarity	NPC212697
0.8483	Intermediate Similarity	NPC171656
0.8483	Intermediate Similarity	NPC287275
0.8478	Intermediate Similarity	NPC307289
0.8473	Intermediate Similarity	NPC31314
0.8473	Intermediate Similarity	NPC474874
0.8472	Intermediate Similarity	NPC471763
0.8472	Intermediate Similarity	NPC476457
0.8467	Intermediate Similarity	NPC19242
0.8467	Intermediate Similarity	NPC279218
0.8467	Intermediate Similarity	NPC108937
0.8467	Intermediate Similarity	NPC32463
0.8462	Intermediate Similarity	NPC96705
0.8462	Intermediate Similarity	NPC152306
0.8462	Intermediate Similarity	NPC471587
0.8462	Intermediate Similarity	NPC265547
0.8456	Intermediate Similarity	NPC199204
0.8456	Intermediate Similarity	NPC157212
0.8444	Intermediate Similarity	NPC471826
0.8444	Intermediate Similarity	NPC188327
0.8444	Intermediate Similarity	NPC234109
0.844	Intermediate Similarity	NPC268081
0.8433	Intermediate Similarity	NPC291899
0.8431	Intermediate Similarity	NPC14822
0.8429	Intermediate Similarity	NPC66705
0.8425	Intermediate Similarity	NPC474302
0.8425	Intermediate Similarity	NPC469700
0.8417	Intermediate Similarity	NPC141822
0.8417	Intermediate Similarity	NPC205797
0.8417	Intermediate Similarity	NPC241165
0.8417	Intermediate Similarity	NPC142563
0.8417	Intermediate Similarity	NPC1220
0.8417	Intermediate Similarity	NPC291551
0.8414	Intermediate Similarity	NPC226722
0.8411	Intermediate Similarity	NPC469936

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 NPC471068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	857
0.2-0.3	1750
0.3-0.4	2573
0.4-0.5	1945
0.5-0.6	1137
0.6-0.7	406
0.7-0.8	118
0.8-0.85	46
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD6859	Clinical (unspecified phase)
0.8542	High Similarity	NPD6799	Approved
0.8523	High Similarity	NPD7096	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD422	Phase 1
0.8417	Intermediate Similarity	NPD5124	Phase 1
0.8417	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD1652	Phase 2
0.8355	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD6798	Discontinued
0.8333	Intermediate Similarity	NPD1296	Phase 2
0.8322	Intermediate Similarity	NPD6599	Discontinued
0.8286	Intermediate Similarity	NPD6355	Discontinued
0.8243	Intermediate Similarity	NPD5403	Approved
0.8235	Intermediate Similarity	NPD2797	Approved
0.8231	Intermediate Similarity	NPD5401	Approved
0.8207	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD4628	Phase 3
0.8207	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD2796	Approved
0.8112	Intermediate Similarity	NPD3748	Approved
0.8071	Intermediate Similarity	NPD3268	Approved
0.8069	Intermediate Similarity	NPD1549	Phase 2
0.8058	Intermediate Similarity	NPD6832	Phase 2
0.8052	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7819	Suspended
0.8026	Intermediate Similarity	NPD7411	Suspended
0.8014	Intermediate Similarity	NPD6233	Phase 2
0.8014	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3817	Phase 2
0.7986	Intermediate Similarity	NPD7033	Discontinued
0.7961	Intermediate Similarity	NPD4380	Phase 2
0.7935	Intermediate Similarity	NPD7768	Phase 2
0.7931	Intermediate Similarity	NPD1551	Phase 2
0.7929	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD3225	Approved
0.7887	Intermediate Similarity	NPD4062	Phase 3
0.7883	Intermediate Similarity	NPD9717	Approved
0.7871	Intermediate Similarity	NPD5402	Approved
0.7867	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4308	Phase 3
0.7862	Intermediate Similarity	NPD1510	Phase 2
0.7857	Intermediate Similarity	NPD1934	Approved
0.7842	Intermediate Similarity	NPD3267	Approved
0.7842	Intermediate Similarity	NPD3266	Approved
0.7838	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD1240	Approved
0.7829	Intermediate Similarity	NPD1653	Approved
0.7823	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1548	Phase 1
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.777	Intermediate Similarity	NPD1243	Approved
0.7763	Intermediate Similarity	NPD920	Approved
0.7733	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1607	Approved
0.7714	Intermediate Similarity	NPD1203	Approved
0.7708	Intermediate Similarity	NPD4307	Phase 2
0.7707	Intermediate Similarity	NPD3882	Suspended
0.7703	Intermediate Similarity	NPD2424	Discontinued
0.7692	Intermediate Similarity	NPD2801	Approved
0.7676	Intermediate Similarity	NPD4908	Phase 1
0.7671	Intermediate Similarity	NPD7097	Phase 1
0.7669	Intermediate Similarity	NPD1241	Discontinued
0.7669	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1894	Discontinued
0.7643	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7199	Phase 2
0.7622	Intermediate Similarity	NPD7095	Approved
0.7619	Intermediate Similarity	NPD2799	Discontinued
0.7615	Intermediate Similarity	NPD1358	Approved
0.761	Intermediate Similarity	NPD919	Approved
0.7607	Intermediate Similarity	NPD3818	Discontinued
0.7594	Intermediate Similarity	NPD7843	Approved
0.7586	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1613	Approved
0.758	Intermediate Similarity	NPD8455	Phase 2
0.7569	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2935	Discontinued
0.7568	Intermediate Similarity	NPD6100	Approved
0.7568	Intermediate Similarity	NPD6099	Approved
0.7566	Intermediate Similarity	NPD1511	Approved
0.7561	Intermediate Similarity	NPD7054	Approved
0.7557	Intermediate Similarity	NPD2684	Approved
0.7554	Intermediate Similarity	NPD1610	Phase 2
0.7554	Intermediate Similarity	NPD1091	Approved
0.7547	Intermediate Similarity	NPD3749	Approved
0.7536	Intermediate Similarity	NPD1778	Approved
0.7535	Intermediate Similarity	NPD1019	Discontinued
0.7534	Intermediate Similarity	NPD4340	Discontinued
0.7534	Intermediate Similarity	NPD230	Phase 1
0.7534	Intermediate Similarity	NPD447	Suspended
0.7531	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6559	Discontinued
0.7518	Intermediate Similarity	NPD9545	Approved
0.7517	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6004	Phase 3
0.7517	Intermediate Similarity	NPD6005	Phase 3
0.7517	Intermediate Similarity	NPD6002	Phase 3
0.7515	Intermediate Similarity	NPD7074	Phase 3
0.7515	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD3027	Phase 3
0.7485	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7481	Intermediate Similarity	NPD290	Approved
0.747	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1465	Phase 2
0.7468	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1512	Approved
0.7468	Intermediate Similarity	NPD5049	Phase 3
0.7467	Intermediate Similarity	NPD4534	Discontinued
0.7466	Intermediate Similarity	NPD4060	Phase 1
0.7463	Intermediate Similarity	NPD5535	Approved
0.7462	Intermediate Similarity	NPD9697	Approved
0.7448	Intermediate Similarity	NPD2313	Discontinued
0.7436	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2354	Approved
0.7434	Intermediate Similarity	NPD3887	Approved
0.7431	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7157	Approved
0.7425	Intermediate Similarity	NPD7251	Discontinued
0.7421	Intermediate Similarity	NPD4288	Approved
0.7419	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1933	Approved
0.7415	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5647	Approved
0.7407	Intermediate Similarity	NPD8127	Discontinued
0.7405	Intermediate Similarity	NPD3134	Approved
0.7405	Intermediate Similarity	NPD37	Approved
0.7403	Intermediate Similarity	NPD2533	Approved
0.7403	Intermediate Similarity	NPD2534	Approved
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2532	Approved
0.74	Intermediate Similarity	NPD5762	Approved
0.74	Intermediate Similarity	NPD5763	Approved
0.7394	Intermediate Similarity	NPD8651	Approved
0.7391	Intermediate Similarity	NPD6234	Discontinued
0.7386	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7808	Phase 3
0.7381	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4965	Approved
0.7375	Intermediate Similarity	NPD4967	Phase 2
0.7375	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4110	Phase 3
0.7368	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6653	Approved
0.7365	Intermediate Similarity	NPD6797	Phase 2
0.7362	Intermediate Similarity	NPD7229	Phase 3
0.7361	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3496	Discontinued
0.7357	Intermediate Similarity	NPD3847	Discontinued
0.7351	Intermediate Similarity	NPD5958	Discontinued
0.7349	Intermediate Similarity	NPD7286	Phase 2
0.7346	Intermediate Similarity	NPD5494	Approved
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4476	Approved
0.7333	Intermediate Similarity	NPD2239	Approved
0.7333	Intermediate Similarity	NPD2240	Approved
0.7333	Intermediate Similarity	NPD4477	Approved
0.7329	Intermediate Similarity	NPD6971	Discontinued
0.7329	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD411	Approved
0.7324	Intermediate Similarity	NPD4749	Approved
0.732	Intermediate Similarity	NPD6190	Approved
0.731	Intermediate Similarity	NPD2614	Approved
0.7305	Intermediate Similarity	NPD1535	Discovery
0.7305	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5953	Discontinued
0.7256	Intermediate Similarity	NPD6232	Discontinued
0.7254	Intermediate Similarity	NPD1481	Phase 2
0.7248	Intermediate Similarity	NPD6651	Approved
0.7246	Intermediate Similarity	NPD9493	Approved
0.7244	Intermediate Similarity	NPD6273	Approved
0.7229	Intermediate Similarity	NPD7473	Discontinued
0.7226	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6362	Approved
0.7219	Intermediate Similarity	NPD6032	Approved
0.7215	Intermediate Similarity	NPD7458	Discontinued
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5691	Approved
0.7211	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3764	Approved
0.7205	Intermediate Similarity	NPD5353	Approved
0.719	Intermediate Similarity	NPD2800	Approved
0.7186	Intermediate Similarity	NPD7228	Approved
0.7186	Intermediate Similarity	NPD3751	Discontinued
0.7176	Intermediate Similarity	NPD7549	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