NPASS Compound

Structure

CID87095 OpenBabel06191715422D 33 37 0 0 1 0 0 0 0 0999 V2000 -5.0594 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3729 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -2.9211 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 -2.4342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6865 -3.8947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 18 2 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 20 2 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 21 1 0 0 0 0 15 26 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 17 2 1 1 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 1 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 30 1 6 0 0 0 22 26 1 1 0 0 0 22 28 1 0 0 0 0 23 29 1 6 0 0 0 24 31 1 1 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 1 0 0 0 29 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.32
Volume:	494.609
LogP:	4.6
LogD:	4.338
LogS:	-4.306
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	5.109
Fsp3:	0.828
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:	-5.559
MDCK Permeability:	1.1213292964384891e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.768
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.197
Plasma Protein Binding (PPB):	94.98160552978516%
Volume Distribution (VD):	0.757
Pgp-substrate:	4.420598983764648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.477
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.214
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.581
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	1.703
Half-life (T1/2):	0.132

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.349
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.092
Carcinogencity:	0.19
Eye Corrosion:	0.722
Eye Irritation:	0.321
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC87095

Natural Product ID:	NPC87095
*Common Name:**	Ilekudinol B
IUPAC Name:	(1S,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-1,2,6a,6b,12a-pentamethyl-9-methylidene-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms:	ilekudinol B
Standard InCHIKey:	RDOIACMZJPLQIZ-FNVOJQHCSA-N
Standard InCHI:	InChI=1S/C29H44O4/c1-16-9-12-29(25(32)33)14-13-27(5)20(23(29)17(16)2)7-8-22-26(4)15-21(30)24(31)18(3)19(26)10-11-28(22,27)6/h7,16-17,19,21-24,30-31H,3,8-15H2,1-2,4-6H3,(H,32,33)/t16-,17+,19+,21-,22-,23+,24-,26+,27-,28-,29+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(=C)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@H]1C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523827
PubChem CID:	10647480
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425145]
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479318]
NPO4734	Syzygium nervosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27797185]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4734	Syzygium nervosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	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	4
Others	2

Activity Type	# Activity
Cell Line	3
CELL-LINE	2
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3065	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Rattus norvegicus	IC50	=	44000.0	nM	PMID[479163]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[479164]
NPT465	Cell Line	NCI-N87	Homo sapiens	IC50	=	9100.0	nM	PMID[479164]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[479164]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	0.123	mg/ml	PMID[479165]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	0.586	mg/ml	PMID[479165]

☑ 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 NPC87095 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	210
0.1-0.2	1265
0.2-0.3	4372
0.3-0.4	12370
0.4-0.5	10826
0.5-0.6	6014
0.6-0.7	5124
0.7-0.8	2024
0.8-0.85	206
0.85-0.9	150
0.9-0.95	126
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC300351
0.9545	High Similarity	NPC472149
0.9545	High Similarity	NPC306541
0.9545	High Similarity	NPC71074
0.9545	High Similarity	NPC84319
0.9545	High Similarity	NPC235884
0.9545	High Similarity	NPC52021
0.9545	High Similarity	NPC25299
0.9444	High Similarity	NPC96916
0.9438	High Similarity	NPC74855
0.9438	High Similarity	NPC275809
0.9438	High Similarity	NPC133579
0.9438	High Similarity	NPC136313
0.9438	High Similarity	NPC307335
0.9438	High Similarity	NPC474806
0.9432	High Similarity	NPC49320
0.9341	High Similarity	NPC173744
0.9341	High Similarity	NPC207922
0.9341	High Similarity	NPC204961
0.9341	High Similarity	NPC259733
0.9341	High Similarity	NPC158371
0.9341	High Similarity	NPC73004
0.9333	High Similarity	NPC299996
0.9333	High Similarity	NPC20235
0.9333	High Similarity	NPC145667
0.9333	High Similarity	NPC282395
0.9333	High Similarity	NPC88116
0.9333	High Similarity	NPC32407
0.9333	High Similarity	NPC231063
0.9333	High Similarity	NPC263548
0.9318	High Similarity	NPC274330
0.9318	High Similarity	NPC198664
0.9318	High Similarity	NPC143232
0.9239	High Similarity	NPC9613
0.9239	High Similarity	NPC259788
0.9239	High Similarity	NPC255589
0.9239	High Similarity	NPC43686
0.9239	High Similarity	NPC247139
0.9231	High Similarity	NPC32118
0.9231	High Similarity	NPC198245
0.9213	High Similarity	NPC111110
0.9213	High Similarity	NPC126369
0.9213	High Similarity	NPC470589
0.9205	High Similarity	NPC473242
0.9205	High Similarity	NPC470629
0.9205	High Similarity	NPC290690
0.9205	High Similarity	NPC182797
0.9205	High Similarity	NPC181225
0.9205	High Similarity	NPC17733
0.9205	High Similarity	NPC474512
0.9205	High Similarity	NPC52169
0.914	High Similarity	NPC29765
0.914	High Similarity	NPC111214
0.914	High Similarity	NPC271614
0.913	High Similarity	NPC230151
0.913	High Similarity	NPC25848
0.913	High Similarity	NPC116457
0.913	High Similarity	NPC201657
0.913	High Similarity	NPC305464
0.913	High Similarity	NPC307282
0.913	High Similarity	NPC19376
0.9121	High Similarity	NPC188102
0.9111	High Similarity	NPC187722
0.9101	High Similarity	NPC61543
0.9101	High Similarity	NPC225585
0.9101	High Similarity	NPC59263
0.9101	High Similarity	NPC270768
0.9101	High Similarity	NPC64872
0.9101	High Similarity	NPC234346
0.9101	High Similarity	NPC127689
0.9101	High Similarity	NPC121798
0.9101	High Similarity	NPC263393
0.9101	High Similarity	NPC470588
0.9101	High Similarity	NPC281524
0.9101	High Similarity	NPC25906
0.9101	High Similarity	NPC130520
0.9101	High Similarity	NPC293048
0.9101	High Similarity	NPC290972
0.9091	High Similarity	NPC98442
0.9091	High Similarity	NPC171203
0.9091	High Similarity	NPC18064
0.9091	High Similarity	NPC130577
0.9091	High Similarity	NPC307426
0.9091	High Similarity	NPC88716
0.9091	High Similarity	NPC293564
0.9091	High Similarity	NPC142415
0.9091	High Similarity	NPC102683
0.9091	High Similarity	NPC68160
0.9091	High Similarity	NPC51700
0.9091	High Similarity	NPC242468
0.9043	High Similarity	NPC35239
0.9032	High Similarity	NPC106112
0.9032	High Similarity	NPC261935
0.9032	High Similarity	NPC189880
0.9022	High Similarity	NPC53565
0.9011	High Similarity	NPC118519
0.9011	High Similarity	NPC202728
0.9011	High Similarity	NPC158059
0.9011	High Similarity	NPC229281
0.9	High Similarity	NPC210037
0.9	High Similarity	NPC290614
0.9	High Similarity	NPC273621
0.9	High Similarity	NPC227467
0.9	High Similarity	NPC474728
0.9	High Similarity	NPC18872
0.9	High Similarity	NPC7260
0.9	High Similarity	NPC477872
0.9	High Similarity	NPC130278
0.9	High Similarity	NPC120968
0.9	High Similarity	NPC46441
0.9	High Similarity	NPC291028
0.8989	High Similarity	NPC40552
0.8989	High Similarity	NPC246708
0.8977	High Similarity	NPC72638
0.8947	High Similarity	NPC233012
0.8947	High Similarity	NPC54909
0.8947	High Similarity	NPC256247
0.8936	High Similarity	NPC188833
0.8936	High Similarity	NPC174663
0.8925	High Similarity	NPC88847
0.8913	High Similarity	NPC209868
0.8913	High Similarity	NPC159365
0.8913	High Similarity	NPC91010
0.8913	High Similarity	NPC6818
0.8913	High Similarity	NPC114159
0.8913	High Similarity	NPC191412
0.8913	High Similarity	NPC296164
0.8901	High Similarity	NPC65120
0.8901	High Similarity	NPC324341
0.8901	High Similarity	NPC155120
0.8901	High Similarity	NPC4036
0.8901	High Similarity	NPC966
0.8901	High Similarity	NPC105189
0.8901	High Similarity	NPC288833
0.8901	High Similarity	NPC474525
0.8901	High Similarity	NPC145067
0.8901	High Similarity	NPC60755
0.8901	High Similarity	NPC470590
0.8901	High Similarity	NPC158030
0.8901	High Similarity	NPC228784
0.8901	High Similarity	NPC282616
0.8901	High Similarity	NPC285184
0.8901	High Similarity	NPC233455
0.8901	High Similarity	NPC38754
0.8901	High Similarity	NPC77099
0.8889	High Similarity	NPC161751
0.8889	High Similarity	NPC474972
0.8889	High Similarity	NPC474686
0.8889	High Similarity	NPC95246
0.8878	High Similarity	NPC301666
0.8876	High Similarity	NPC71507
0.8876	High Similarity	NPC477926
0.883	High Similarity	NPC203343
0.883	High Similarity	NPC312075
0.8817	High Similarity	NPC473240
0.8817	High Similarity	NPC290481
0.8804	High Similarity	NPC298554
0.8804	High Similarity	NPC214756
0.8804	High Similarity	NPC272075
0.8804	High Similarity	NPC295643
0.8804	High Similarity	NPC86368
0.8791	High Similarity	NPC113989
0.8791	High Similarity	NPC120840
0.8791	High Similarity	NPC172361
0.8791	High Similarity	NPC193750
0.8791	High Similarity	NPC86372
0.8778	High Similarity	NPC474511
0.8778	High Similarity	NPC1753
0.8776	High Similarity	NPC80566
0.8764	High Similarity	NPC187545
0.8764	High Similarity	NPC324063
0.8764	High Similarity	NPC56588
0.875	High Similarity	NPC180834
0.8723	High Similarity	NPC327179
0.8723	High Similarity	NPC157113
0.8723	High Similarity	NPC62516
0.8723	High Similarity	NPC476327
0.8723	High Similarity	NPC132824
0.8723	High Similarity	NPC476318
0.871	High Similarity	NPC80365
0.871	High Similarity	NPC470958
0.871	High Similarity	NPC474529
0.871	High Similarity	NPC470957
0.871	High Similarity	NPC222047
0.8696	High Similarity	NPC301244
0.8696	High Similarity	NPC471588
0.8696	High Similarity	NPC6255
0.8696	High Similarity	NPC475708
0.8696	High Similarity	NPC189520
0.8681	High Similarity	NPC30522
0.8673	High Similarity	NPC284865
0.8667	High Similarity	NPC73064
0.8667	High Similarity	NPC158141
0.8667	High Similarity	NPC173089
0.8652	High Similarity	NPC274724
0.8652	High Similarity	NPC133954
0.8632	High Similarity	NPC187933
0.8632	High Similarity	NPC470425
0.8617	High Similarity	NPC195715
0.8617	High Similarity	NPC148523

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 NPC87095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1583
0.2-0.3	3708
0.3-0.4	2421
0.4-0.5	778
0.5-0.6	238
0.6-0.7	210
0.7-0.8	23
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8901	High Similarity	NPD7515	Phase 2
0.8511	High Similarity	NPD7748	Approved
0.8247	Intermediate Similarity	NPD7902	Approved
0.8043	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7900	Approved
0.7938	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4786	Approved
0.7912	Intermediate Similarity	NPD3667	Approved
0.7835	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD7645	Phase 2
0.7708	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD3618	Phase 1
0.7551	Intermediate Similarity	NPD8035	Phase 2
0.7551	Intermediate Similarity	NPD8034	Phase 2
0.7549	Intermediate Similarity	NPD7640	Approved
0.7549	Intermediate Similarity	NPD7639	Approved
0.7526	Intermediate Similarity	NPD5328	Approved
0.7477	Intermediate Similarity	NPD7115	Discovery
0.7451	Intermediate Similarity	NPD7638	Approved
0.7423	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6079	Approved
0.7374	Intermediate Similarity	NPD6411	Approved
0.7368	Intermediate Similarity	NPD3668	Phase 3
0.7368	Intermediate Similarity	NPD3665	Phase 1
0.7368	Intermediate Similarity	NPD3666	Approved
0.7368	Intermediate Similarity	NPD3133	Approved
0.7315	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4225	Approved
0.7216	Intermediate Similarity	NPD6409	Approved
0.7216	Intermediate Similarity	NPD6684	Approved
0.7216	Intermediate Similarity	NPD7146	Approved
0.7216	Intermediate Similarity	NPD5330	Approved
0.7216	Intermediate Similarity	NPD7521	Approved
0.7216	Intermediate Similarity	NPD7334	Approved
0.7196	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD6402	Approved
0.7196	Intermediate Similarity	NPD5739	Approved
0.7196	Intermediate Similarity	NPD7128	Approved
0.7184	Intermediate Similarity	NPD6083	Phase 2
0.7184	Intermediate Similarity	NPD6084	Phase 2
0.7172	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6101	Approved
0.7168	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD7339	Approved
0.7129	Intermediate Similarity	NPD5779	Approved
0.7129	Intermediate Similarity	NPD4202	Approved
0.7129	Intermediate Similarity	NPD5778	Approved
0.7128	Intermediate Similarity	NPD4695	Discontinued
0.7128	Intermediate Similarity	NPD7525	Registered
0.7094	Intermediate Similarity	NPD8328	Phase 3
0.7087	Intermediate Similarity	NPD5221	Approved
0.7087	Intermediate Similarity	NPD5222	Approved
0.7087	Intermediate Similarity	NPD4697	Phase 3
0.7087	Intermediate Similarity	NPD7614	Phase 1
0.7087	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5211	Phase 2
0.7071	Intermediate Similarity	NPD6672	Approved
0.7071	Intermediate Similarity	NPD5737	Approved
0.7071	Intermediate Similarity	NPD6903	Approved
0.7065	Intermediate Similarity	NPD6117	Approved
0.7065	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7320	Approved
0.7064	Intermediate Similarity	NPD6881	Approved
0.7064	Intermediate Similarity	NPD6899	Approved
0.7033	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5173	Approved
0.7019	Intermediate Similarity	NPD4755	Approved
0.7	Intermediate Similarity	NPD4753	Phase 2
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6373	Approved
0.6989	Remote Similarity	NPD6116	Phase 1
0.6972	Remote Similarity	NPD6412	Phase 2
0.6972	Remote Similarity	NPD5701	Approved
0.6972	Remote Similarity	NPD5697	Approved
0.697	Remote Similarity	NPD3573	Approved
0.6964	Remote Similarity	NPD8297	Approved
0.6944	Remote Similarity	NPD5141	Approved
0.6937	Remote Similarity	NPD7290	Approved
0.6937	Remote Similarity	NPD7102	Approved
0.6937	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD7632	Discontinued
0.6915	Remote Similarity	NPD6115	Approved
0.6915	Remote Similarity	NPD6697	Approved
0.6915	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6114	Approved
0.6915	Remote Similarity	NPD6118	Approved
0.6909	Remote Similarity	NPD6686	Approved
0.6909	Remote Similarity	NPD6011	Approved
0.6903	Remote Similarity	NPD4632	Approved
0.6903	Remote Similarity	NPD8133	Approved
0.6887	Remote Similarity	NPD4700	Approved
0.6887	Remote Similarity	NPD4696	Approved
0.6887	Remote Similarity	NPD5286	Approved
0.6887	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD8130	Phase 1
0.6875	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6650	Approved
0.6875	Remote Similarity	NPD6617	Approved
0.6875	Remote Similarity	NPD6649	Approved
0.6875	Remote Similarity	NPD6847	Approved
0.6875	Remote Similarity	NPD6869	Approved
0.6869	Remote Similarity	NPD4623	Approved
0.6869	Remote Similarity	NPD5279	Phase 3
0.6869	Remote Similarity	NPD4519	Discontinued
0.6847	Remote Similarity	NPD6014	Approved
0.6847	Remote Similarity	NPD6013	Approved
0.6847	Remote Similarity	NPD6012	Approved
0.6827	Remote Similarity	NPD5695	Phase 3
0.6822	Remote Similarity	NPD5223	Approved
0.6814	Remote Similarity	NPD6882	Approved
0.6804	Remote Similarity	NPD4221	Approved
0.6804	Remote Similarity	NPD4223	Phase 3
0.6804	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5696	Approved
0.6774	Remote Similarity	NPD8264	Approved
0.6768	Remote Similarity	NPD5329	Approved
0.6762	Remote Similarity	NPD7732	Phase 3
0.6759	Remote Similarity	NPD5224	Approved
0.6759	Remote Similarity	NPD5226	Approved
0.6759	Remote Similarity	NPD5225	Approved
0.6759	Remote Similarity	NPD4633	Approved
0.6757	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5362	Discontinued
0.6735	Remote Similarity	NPD4788	Approved
0.6702	Remote Similarity	NPD6933	Approved
0.67	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6098	Approved
0.6699	Remote Similarity	NPD5281	Approved
0.6699	Remote Similarity	NPD7637	Suspended
0.6699	Remote Similarity	NPD5284	Approved
0.6697	Remote Similarity	NPD5174	Approved
0.6697	Remote Similarity	NPD4754	Approved
0.6697	Remote Similarity	NPD5175	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6638	Remote Similarity	NPD6868	Approved
0.6637	Remote Similarity	NPD4634	Approved
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7524	Approved
0.6634	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4269	Approved
0.6633	Remote Similarity	NPD4270	Approved
0.663	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6009	Approved
0.6577	Remote Similarity	NPD6008	Approved
0.6577	Remote Similarity	NPD4767	Approved
0.6577	Remote Similarity	NPD4768	Approved
0.6566	Remote Similarity	NPD7154	Phase 3
0.6562	Remote Similarity	NPD3617	Approved
0.6555	Remote Similarity	NPD6319	Approved
0.6538	Remote Similarity	NPD5693	Phase 1
0.6535	Remote Similarity	NPD5205	Approved
0.6535	Remote Similarity	NPD4690	Approved
0.6535	Remote Similarity	NPD4138	Approved
0.6535	Remote Similarity	NPD4689	Approved
0.6535	Remote Similarity	NPD4693	Phase 3
0.6535	Remote Similarity	NPD4688	Approved
0.6532	Remote Similarity	NPD7319	Approved
0.6525	Remote Similarity	NPD6335	Approved
0.6505	Remote Similarity	NPD6051	Approved
0.65	Remote Similarity	NPD8033	Approved
0.6496	Remote Similarity	NPD6274	Approved
0.6495	Remote Similarity	NPD6929	Approved
0.6489	Remote Similarity	NPD6924	Approved
0.6489	Remote Similarity	NPD6926	Approved
0.6471	Remote Similarity	NPD7100	Approved
0.6471	Remote Similarity	NPD7516	Approved
0.6471	Remote Similarity	NPD7101	Approved
0.646	Remote Similarity	NPD4729	Approved
0.646	Remote Similarity	NPD5168	Approved
0.646	Remote Similarity	NPD5128	Approved
0.646	Remote Similarity	NPD4730	Approved
0.6452	Remote Similarity	NPD7736	Approved
0.6442	Remote Similarity	NPD46	Approved
0.6442	Remote Similarity	NPD5785	Approved
0.6442	Remote Similarity	NPD6698	Approved
0.6441	Remote Similarity	NPD6317	Approved
0.6436	Remote Similarity	NPD5363	Approved
0.6436	Remote Similarity	NPD1694	Approved
0.6429	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD4819	Approved
0.6429	Remote Similarity	NPD4821	Approved
0.6429	Remote Similarity	NPD4252	Approved
0.6429	Remote Similarity	NPD6930	Phase 2
0.6429	Remote Similarity	NPD4822	Approved
0.6429	Remote Similarity	NPD6931	Approved
0.6422	Remote Similarity	NPD6404	Discontinued
0.6417	Remote Similarity	NPD8294	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