NPASS Compound

Structure

NPC273248 OpenBabel07101719242D 25 27 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 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 5.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 4.3301 -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 3.4641 1.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 25 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 22 2 0 0 0 0 13 20 1 0 0 0 0 13 21 1 1 0 0 0 14 17 1 0 0 0 0 14 19 2 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 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 25 1 0 0 0 0 21 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.21
Volume:	370.718
LogP:	5.205
LogD:	4.015
LogS:	-4.613
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	3.859
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.758
MDCK Permeability:	1.959725886990782e-05
Pgp-inhibitor:	0.162
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.715
30% Bioavailability (F30%):	0.203

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.231
Plasma Protein Binding (PPB):	98.70128631591797%
Volume Distribution (VD):	2.726
Pgp-substrate:	2.7851221561431885%

ADMET: Metabolism

CYP1A2-inhibitor:	0.434
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.421
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.567
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.387
CYP2D6-substrate:	0.397
CYP3A4-inhibitor:	0.385
CYP3A4-substrate:	0.456

ADMET: Excretion

Clearance (CL):	3.677
Half-life (T1/2):	0.1

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.134
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.213
Skin Sensitization:	0.798
Carcinogencity:	0.095
Eye Corrosion:	0.003
Eye Irritation:	0.741
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC273248

Natural Product ID:	NPC273248
*Common Name:**	Inuroyleanol
IUPAC Name:	(4aS,10aS)-5,8-dihydroxy-6-methoxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
Synonyms:	Inuroyleanol
Standard InCHIKey:	ACKWWYIXLTYJCG-ZSEKCTLFSA-N
Standard InCHI:	InChI=1S/C21H30O4/c1-11(2)14-17(23)15-12(22)10-13-20(3,4)8-7-9-21(13,5)16(15)18(24)19(14)25-6/h11,13,23-24H,7-10H2,1-6H3/t13-,21-/m0/s1
SMILES:	CC(C)c1c(c2C(=O)C[C@H]3C(C)(C)CCC[C@]3(C)c2c(c1OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813347
PubChem CID:	15386508
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO13465	Salvia broussonetii	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[15969497]
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	roots	Santa Maria, South Brazil	2007-Dec	PMID[21775156]
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13465	Salvia broussonetii	Species	Lamiaceae	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
EC50	1
IC50	7
Others	3

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	>	80000.0	nM	PMID[496037]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30000.0	nM	PMID[496039]
NPT793	Cell Line	MOLT-3	Homo sapiens	IC50	>	30000.0	nM	PMID[496039]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	20800.0	nM	PMID[496039]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	11100.0	nM	PMID[496039]
NPT926	Cell Line	SK-MEL-1	Homo sapiens	IC50	>	30000.0	nM	PMID[496039]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	120000.0	nM	PMID[496037]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	106.0	%	PMID[496038]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	119.0	%	PMID[496038]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	0.0	%	PMID[496038]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	EC50	>	100.0	microg/cm2	PMID[496038]

☑ 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 NPC273248 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	425
0.1-0.2	1891
0.2-0.3	3900
0.3-0.4	9676
0.4-0.5	9194
0.5-0.6	4424
0.6-0.7	5939
0.7-0.8	6017
0.8-0.85	1051
0.85-0.9	142
0.9-0.95	33
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC161778
0.96	High Similarity	NPC25850
0.96	High Similarity	NPC276815
0.9536	High Similarity	NPC283301
0.9419	High Similarity	NPC102372
0.9231	High Similarity	NPC208120
0.9231	High Similarity	NPC173587
0.9231	High Similarity	NPC29055
0.9178	High Similarity	NPC92079
0.9177	High Similarity	NPC232936
0.9172	High Similarity	NPC21016
0.9172	High Similarity	NPC146584
0.9161	High Similarity	NPC84571
0.9161	High Similarity	NPC161947
0.9161	High Similarity	NPC155302
0.9119	High Similarity	NPC213416
0.9108	High Similarity	NPC475055
0.9103	High Similarity	NPC87431
0.9103	High Similarity	NPC311740
0.9032	High Similarity	NPC37543
0.9032	High Similarity	NPC199463
0.9026	High Similarity	NPC472048
0.902	High Similarity	NPC218628
0.8987	High Similarity	NPC270837
0.8987	High Similarity	NPC236132
0.8987	High Similarity	NPC220313
0.8968	High Similarity	NPC77807
0.8968	High Similarity	NPC5379
0.8968	High Similarity	NPC474167
0.8968	High Similarity	NPC470762
0.8968	High Similarity	NPC14561
0.8924	High Similarity	NPC470694
0.8924	High Similarity	NPC294965
0.8917	High Similarity	NPC14353
0.8917	High Similarity	NPC228785
0.8917	High Similarity	NPC56085
0.891	High Similarity	NPC178976
0.891	High Similarity	NPC179732
0.8889	High Similarity	NPC50269
0.8861	High Similarity	NPC278052
0.8861	High Similarity	NPC61010
0.8861	High Similarity	NPC32694
0.8861	High Similarity	NPC66288
0.8861	High Similarity	NPC40491
0.8854	High Similarity	NPC100123
0.8854	High Similarity	NPC45846
0.8839	High Similarity	NPC107109
0.8824	High Similarity	NPC303989
0.8812	High Similarity	NPC26386
0.8812	High Similarity	NPC25361
0.8805	High Similarity	NPC215612
0.8797	High Similarity	NPC45146
0.8797	High Similarity	NPC320359
0.8797	High Similarity	NPC80375
0.8797	High Similarity	NPC235018
0.8797	High Similarity	NPC119224
0.879	High Similarity	NPC165977
0.879	High Similarity	NPC300727
0.879	High Similarity	NPC241904
0.879	High Similarity	NPC217677
0.8782	High Similarity	NPC134287
0.8782	High Similarity	NPC130589
0.8773	High Similarity	NPC158226
0.8765	High Similarity	NPC163130
0.8765	High Similarity	NPC165979
0.8758	High Similarity	NPC37870
0.8758	High Similarity	NPC476058
0.875	High Similarity	NPC101769
0.875	High Similarity	NPC197168
0.875	High Similarity	NPC7483
0.875	High Similarity	NPC248638
0.875	High Similarity	NPC152659
0.875	High Similarity	NPC236521
0.8742	High Similarity	NPC65746
0.8742	High Similarity	NPC472275
0.8734	High Similarity	NPC235448
0.8734	High Similarity	NPC476242
0.8726	High Similarity	NPC274730
0.8726	High Similarity	NPC142339
0.8718	High Similarity	NPC477047
0.8718	High Similarity	NPC477048
0.8718	High Similarity	NPC93552
0.8696	High Similarity	NPC472450
0.8696	High Similarity	NPC275780
0.8696	High Similarity	NPC239752
0.8696	High Similarity	NPC473286
0.8696	High Similarity	NPC326520
0.8693	High Similarity	NPC251188
0.8688	High Similarity	NPC25152
0.8679	High Similarity	NPC297212
0.8679	High Similarity	NPC475886
0.8679	High Similarity	NPC474287
0.8671	High Similarity	NPC78103
0.8671	High Similarity	NPC180011
0.8671	High Similarity	NPC79053
0.8671	High Similarity	NPC236796
0.8671	High Similarity	NPC78225
0.8671	High Similarity	NPC36852
0.8671	High Similarity	NPC219867
0.8671	High Similarity	NPC469584
0.8671	High Similarity	NPC262286
0.8662	High Similarity	NPC39184
0.8662	High Similarity	NPC68727
0.8654	High Similarity	NPC149889
0.8654	High Similarity	NPC268992
0.8654	High Similarity	NPC312338
0.8654	High Similarity	NPC51824
0.8654	High Similarity	NPC113608
0.8654	High Similarity	NPC470337
0.8654	High Similarity	NPC470338
0.865	High Similarity	NPC49487
0.865	High Similarity	NPC476637
0.865	High Similarity	NPC99613
0.8645	High Similarity	NPC472279
0.8645	High Similarity	NPC294646
0.8642	High Similarity	NPC170245
0.8642	High Similarity	NPC29160
0.8642	High Similarity	NPC39091
0.8636	High Similarity	NPC131451
0.8636	High Similarity	NPC15329
0.8634	High Similarity	NPC303460
0.8634	High Similarity	NPC146134
0.8634	High Similarity	NPC23298
0.8634	High Similarity	NPC207690
0.8634	High Similarity	NPC306321
0.8634	High Similarity	NPC189473
0.8631	High Similarity	NPC240508
0.8625	High Similarity	NPC278427
0.8625	High Similarity	NPC266314
0.8625	High Similarity	NPC474186
0.8625	High Similarity	NPC475883
0.8625	High Similarity	NPC474351
0.8625	High Similarity	NPC474187
0.8618	High Similarity	NPC309169
0.8618	High Similarity	NPC196941
0.8616	High Similarity	NPC315157
0.8616	High Similarity	NPC46736
0.8616	High Similarity	NPC85121
0.8616	High Similarity	NPC250214
0.8616	High Similarity	NPC172770
0.8616	High Similarity	NPC185258
0.8616	High Similarity	NPC95936
0.8608	High Similarity	NPC191146
0.8608	High Similarity	NPC115853
0.8608	High Similarity	NPC68093
0.8608	High Similarity	NPC138243
0.8599	High Similarity	NPC250557
0.8599	High Similarity	NPC124714
0.8599	High Similarity	NPC89474
0.8598	High Similarity	NPC109827
0.8598	High Similarity	NPC124470
0.859	High Similarity	NPC45291
0.859	High Similarity	NPC19980
0.859	High Similarity	NPC78505
0.859	High Similarity	NPC302783
0.859	High Similarity	NPC473201
0.8589	High Similarity	NPC126204
0.8589	High Similarity	NPC6588
0.8589	High Similarity	NPC117854
0.8589	High Similarity	NPC477154
0.8589	High Similarity	NPC234331
0.8581	High Similarity	NPC134293
0.8581	High Similarity	NPC102003
0.8581	High Similarity	NPC92722
0.8571	High Similarity	NPC229632
0.8571	High Similarity	NPC52692
0.8571	High Similarity	NPC52204
0.8563	High Similarity	NPC77179
0.8563	High Similarity	NPC23553
0.8562	High Similarity	NPC200746
0.8562	High Similarity	NPC246478
0.8562	High Similarity	NPC476280
0.8562	High Similarity	NPC36217
0.8562	High Similarity	NPC476980
0.8562	High Similarity	NPC185617
0.8553	High Similarity	NPC187745
0.8553	High Similarity	NPC223787
0.8553	High Similarity	NPC472914
0.8553	High Similarity	NPC161960
0.8553	High Similarity	NPC245758
0.8553	High Similarity	NPC302258
0.8553	High Similarity	NPC96167
0.8553	High Similarity	NPC472911
0.8553	High Similarity	NPC222814
0.8553	High Similarity	NPC136674
0.8553	High Similarity	NPC472910
0.8553	High Similarity	NPC472913
0.8553	High Similarity	NPC304008
0.8544	High Similarity	NPC234485
0.8544	High Similarity	NPC16286
0.8544	High Similarity	NPC113906
0.8537	High Similarity	NPC475805
0.8535	High Similarity	NPC474993
0.8535	High Similarity	NPC100263
0.8535	High Similarity	NPC100971
0.8535	High Similarity	NPC245382
0.8535	High Similarity	NPC471982
0.8535	High Similarity	NPC180944
0.8535	High Similarity	NPC121522
0.8535	High Similarity	NPC269451

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 NPC273248 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	1128
0.2-0.3	2144
0.3-0.4	2727
0.4-0.5	1653
0.5-0.6	760
0.6-0.7	272
0.7-0.8	86
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD7473	Discontinued
0.8571	High Similarity	NPD6232	Discontinued
0.8481	Intermediate Similarity	NPD2801	Approved
0.825	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2532	Approved
0.8205	Intermediate Similarity	NPD2533	Approved
0.8205	Intermediate Similarity	NPD2534	Approved
0.82	Intermediate Similarity	NPD6651	Approved
0.8187	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD2800	Approved
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7952	Intermediate Similarity	NPD6959	Discontinued
0.7927	Intermediate Similarity	NPD3882	Suspended
0.7917	Intermediate Similarity	NPD6166	Phase 2
0.7917	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1511	Approved
0.7812	Intermediate Similarity	NPD1512	Approved
0.775	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4380	Phase 2
0.7719	Intermediate Similarity	NPD3818	Discontinued
0.7711	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7651	Intermediate Similarity	NPD3817	Phase 2
0.764	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7074	Phase 3
0.7619	Intermediate Similarity	NPD6234	Discontinued
0.7613	Intermediate Similarity	NPD1607	Approved
0.76	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7819	Suspended
0.7588	Intermediate Similarity	NPD5711	Approved
0.7588	Intermediate Similarity	NPD5710	Approved
0.7578	Intermediate Similarity	NPD7390	Discontinued
0.7572	Intermediate Similarity	NPD7054	Approved
0.7545	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD37	Approved
0.7529	Intermediate Similarity	NPD7472	Approved
0.7516	Intermediate Similarity	NPD1510	Phase 2
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7484	Intermediate Similarity	NPD1240	Approved
0.7484	Intermediate Similarity	NPD943	Approved
0.7468	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD6100	Approved
0.7468	Intermediate Similarity	NPD2935	Discontinued
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7075	Discontinued
0.7405	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7386	Intermediate Similarity	NPD6797	Phase 2
0.7381	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3226	Approved
0.7345	Intermediate Similarity	NPD7251	Discontinued
0.7326	Intermediate Similarity	NPD1247	Approved
0.7321	Intermediate Similarity	NPD6801	Discontinued
0.7314	Intermediate Similarity	NPD7228	Approved
0.7312	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7808	Phase 3
0.7288	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1549	Phase 2
0.7262	Intermediate Similarity	NPD7411	Suspended
0.7251	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6559	Discontinued
0.7229	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD230	Phase 1
0.7205	Intermediate Similarity	NPD2346	Discontinued
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7178	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6799	Approved
0.7151	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD2796	Approved
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7135	Intermediate Similarity	NPD5402	Approved
0.7134	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7199	Phase 2
0.7102	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7768	Phase 2
0.709	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7003	Approved
0.7073	Intermediate Similarity	NPD4628	Phase 3
0.7073	Intermediate Similarity	NPD3750	Approved
0.7072	Intermediate Similarity	NPD8312	Approved
0.7072	Intermediate Similarity	NPD8313	Approved
0.707	Intermediate Similarity	NPD3027	Phase 3
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7045	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5408	Approved
0.7037	Intermediate Similarity	NPD5405	Approved
0.7037	Intermediate Similarity	NPD5404	Approved
0.7037	Intermediate Similarity	NPD5406	Approved
0.7012	Intermediate Similarity	NPD6674	Discontinued
0.7011	Intermediate Similarity	NPD919	Approved
0.7005	Intermediate Similarity	NPD6535	Approved
0.7005	Intermediate Similarity	NPD6534	Approved
0.6979	Remote Similarity	NPD7697	Approved
0.6979	Remote Similarity	NPD7696	Phase 3
0.6979	Remote Similarity	NPD7698	Approved
0.6957	Remote Similarity	NPD8434	Phase 2
0.6946	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7870	Phase 2
0.6943	Remote Similarity	NPD9494	Approved
0.6943	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7871	Phase 2
0.6937	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3620	Phase 2
0.6927	Remote Similarity	NPD3751	Discontinued
0.6927	Remote Similarity	NPD6823	Phase 2
0.6923	Remote Similarity	NPD7701	Phase 2
0.6923	Remote Similarity	NPD1470	Approved
0.6909	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7801	Approved
0.6899	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7699	Phase 2
0.6895	Remote Similarity	NPD7700	Phase 2
0.6894	Remote Similarity	NPD447	Suspended
0.6893	Remote Similarity	NPD3787	Discontinued
0.6883	Remote Similarity	NPD1201	Approved
0.6871	Remote Similarity	NPD2799	Discontinued
0.6868	Remote Similarity	NPD7240	Approved
0.6867	Remote Similarity	NPD8166	Discontinued
0.6867	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7874	Approved
0.6853	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1613	Approved
0.6831	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1551	Phase 2
0.6826	Remote Similarity	NPD6190	Approved
0.6824	Remote Similarity	NPD920	Approved
0.6818	Remote Similarity	NPD7783	Phase 2
0.6818	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7985	Registered
0.6805	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7229	Phase 3
0.6796	Remote Similarity	NPD7286	Phase 2
0.6795	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3300	Phase 2
0.6772	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6212	Phase 3
0.6772	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6213	Phase 3
0.6768	Remote Similarity	NPD3748	Approved
0.675	Remote Similarity	NPD4625	Phase 3
0.6744	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8127	Discontinued
0.6731	Remote Similarity	NPD3972	Approved
0.6731	Remote Similarity	NPD9269	Phase 2
0.6725	Remote Similarity	NPD5403	Approved
0.6723	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2403	Approved
0.6721	Remote Similarity	NPD5953	Discontinued
0.6711	Remote Similarity	NPD7340	Approved
0.6708	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2313	Discontinued
0.6708	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1243	Approved
0.6705	Remote Similarity	NPD7028	Phase 2
0.6701	Remote Similarity	NPD2493	Approved
0.6701	Remote Similarity	NPD2494	Approved
0.6687	Remote Similarity	NPD2344	Approved
0.6686	Remote Similarity	NPD5761	Phase 2
0.6686	Remote Similarity	NPD1653	Approved
0.6686	Remote Similarity	NPD5760	Phase 2
0.6685	Remote Similarity	NPD7685	Pre-registration
0.6684	Remote Similarity	NPD4582	Approved
0.6684	Remote Similarity	NPD4583	Approved
0.6667	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD4665	Approved
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD5242	Approved
0.6648	Remote Similarity	NPD5353	Approved
0.6646	Remote Similarity	NPD6696	Suspended
0.6646	Remote Similarity	NPD1283	Approved
0.6633	Remote Similarity	NPD4004	Approved
0.6633	Remote Similarity	NPD4002	Approved
0.6623	Remote Similarity	NPD1398	Phase 1
0.6615	Remote Similarity	NPD3452	Approved
0.6615	Remote Similarity	NPD3450	Approved
0.6608	Remote Similarity	NPD5401	Approved
0.6608	Remote Similarity	NPD642	Clinical (unspecified phase)

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