NPASS Compound

Structure

NPC291001 OpenBabel07101719142D 23 25 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 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 -4.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.8660 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 -1.7321 -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 -3.4641 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -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 1 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 0.8660 -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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 21 2 0 0 0 0 12 14 1 0 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 15 19 1 0 0 0 0 15 20 1 1 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 20 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	4.091
LogD:	3.406
LogS:	-3.684
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.627
Synthetic Accessibility Score:	3.894
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.748
MDCK Permeability:	1.7901076716952957e-05
Pgp-inhibitor:	0.83
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	95.13577270507812%
Volume Distribution (VD):	5.237
Pgp-substrate:	1.8502991199493408%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.796
CYP2C19-inhibitor:	0.135
CYP2C19-substrate:	0.701
CYP2C9-inhibitor:	0.147
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.864
CYP2D6-substrate:	0.552
CYP3A4-inhibitor:	0.518
CYP3A4-substrate:	0.331

ADMET: Excretion

Clearance (CL):	3.164
Half-life (T1/2):	0.287

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.319
Rat Oral Acute Toxicity:	0.254
Maximum Recommended Daily Dose:	0.814
Skin Sensitization:	0.954
Carcinogencity:	0.086
Eye Corrosion:	0.015
Eye Irritation:	0.921
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC291001

Natural Product ID:	NPC291001
*Common Name:**	Carnosaldehyde
IUPAC Name:	(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carbaldehyde
Synonyms:
Standard InCHIKey:	RCVGXYUBWJMZTF-MGPUTAFESA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-12(2)14-10-13-6-7-15-19(3,4)8-5-9-20(15,11-21)16(13)18(23)17(14)22/h10-12,15,22-23H,5-9H2,1-4H3/t15-,20+/m0/s1
SMILES:	CC(C)c1cc2CC[C@H]3C(C)(C)CCC[C@]3(C=O)c2c(c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2376099
PubChem CID:	71712255
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
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096857]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23507152]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6098	Salvia officinalis	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1651	Individual Protein	Nuclear factor erythroid 2-related factor 2	Mus musculus	FC	=	50.0	n.a.	PMID[541376]

☑ 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 NPC291001 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	308
0.1-0.2	1411
0.2-0.3	2998
0.3-0.4	8285
0.4-0.5	11102
0.5-0.6	6795
0.6-0.7	10147
0.7-0.8	1475
0.8-0.85	134
0.85-0.9	34
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.936	High Similarity	NPC137750
0.9231	High Similarity	NPC111845
0.916	High Similarity	NPC293454
0.912	High Similarity	NPC11250
0.9091	High Similarity	NPC153088
0.9084	High Similarity	NPC138472
0.9037	High Similarity	NPC471853
0.9037	High Similarity	NPC476534
0.8905	High Similarity	NPC248068
0.8889	High Similarity	NPC253627
0.8846	High Similarity	NPC3009
0.8828	High Similarity	NPC181334
0.8797	High Similarity	NPC477139
0.8777	High Similarity	NPC126707
0.875	High Similarity	NPC471187
0.875	High Similarity	NPC230811
0.8682	High Similarity	NPC15127
0.8676	High Similarity	NPC49911
0.8676	High Similarity	NPC277559
0.8652	High Similarity	NPC191899
0.8652	High Similarity	NPC474991
0.8652	High Similarity	NPC246229
0.8647	High Similarity	NPC471851
0.8643	High Similarity	NPC309169
0.8643	High Similarity	NPC196941
0.8626	High Similarity	NPC176130
0.8626	High Similarity	NPC78364
0.8626	High Similarity	NPC84672
0.8626	High Similarity	NPC69424
0.8594	High Similarity	NPC249340
0.8594	High Similarity	NPC162935
0.8593	High Similarity	NPC202225
0.8582	High Similarity	NPC84786
0.8571	High Similarity	NPC199936
0.8571	High Similarity	NPC108129
0.8561	High Similarity	NPC272907
0.8561	High Similarity	NPC2681
0.8529	High Similarity	NPC103082
0.8527	High Similarity	NPC176208
0.8521	High Similarity	NPC58752
0.8519	High Similarity	NPC476282
0.8519	High Similarity	NPC49742
0.8519	High Similarity	NPC78307
0.8516	High Similarity	NPC32322
0.8516	High Similarity	NPC259703
0.8507	High Similarity	NPC243305
0.85	High Similarity	NPC184935
0.8496	Intermediate Similarity	NPC276238
0.8492	Intermediate Similarity	NPC16030
0.8485	Intermediate Similarity	NPC72667
0.8478	Intermediate Similarity	NPC141368
0.8478	Intermediate Similarity	NPC206207
0.8473	Intermediate Similarity	NPC87985
0.8468	Intermediate Similarity	NPC317869
0.8462	Intermediate Similarity	NPC52692
0.8462	Intermediate Similarity	NPC127046
0.8462	Intermediate Similarity	NPC470757
0.8462	Intermediate Similarity	NPC198014
0.8451	Intermediate Similarity	NPC68441
0.845	Intermediate Similarity	NPC154696
0.8414	Intermediate Similarity	NPC470037
0.8409	Intermediate Similarity	NPC254492
0.8406	Intermediate Similarity	NPC475957
0.8397	Intermediate Similarity	NPC199273
0.8394	Intermediate Similarity	NPC258502
0.8392	Intermediate Similarity	NPC476535
0.8387	Intermediate Similarity	NPC471179
0.8385	Intermediate Similarity	NPC121168
0.8385	Intermediate Similarity	NPC471794
0.8372	Intermediate Similarity	NPC241001
0.837	Intermediate Similarity	NPC476847
0.8358	Intermediate Similarity	NPC303910
0.8358	Intermediate Similarity	NPC171460
0.8357	Intermediate Similarity	NPC3218
0.8333	Intermediate Similarity	NPC192948
0.8333	Intermediate Similarity	NPC35797
0.8322	Intermediate Similarity	NPC470038
0.8322	Intermediate Similarity	NPC75295
0.8295	Intermediate Similarity	NPC478121
0.8276	Intermediate Similarity	NPC471852
0.8268	Intermediate Similarity	NPC38893
0.8268	Intermediate Similarity	NPC477137
0.8268	Intermediate Similarity	NPC308311
0.8248	Intermediate Similarity	NPC4170
0.8235	Intermediate Similarity	NPC41847
0.8227	Intermediate Similarity	NPC470035
0.8217	Intermediate Similarity	NPC42657
0.8214	Intermediate Similarity	NPC469681
0.8214	Intermediate Similarity	NPC416
0.8214	Intermediate Similarity	NPC469680
0.8214	Intermediate Similarity	NPC61398
0.8214	Intermediate Similarity	NPC471974
0.8203	Intermediate Similarity	NPC304510
0.8203	Intermediate Similarity	NPC172219
0.8201	Intermediate Similarity	NPC7464
0.8194	Intermediate Similarity	NPC258856
0.8168	Intermediate Similarity	NPC474115
0.8163	Intermediate Similarity	NPC476532
0.816	Intermediate Similarity	NPC176279
0.816	Intermediate Similarity	NPC260323
0.8154	Intermediate Similarity	NPC190501
0.8154	Intermediate Similarity	NPC318552
0.8148	Intermediate Similarity	NPC201069
0.8148	Intermediate Similarity	NPC96024
0.8148	Intermediate Similarity	NPC234175
0.814	Intermediate Similarity	NPC471671
0.8138	Intermediate Similarity	NPC39361
0.8134	Intermediate Similarity	NPC71610
0.8129	Intermediate Similarity	NPC252343
0.8125	Intermediate Similarity	NPC219112
0.8125	Intermediate Similarity	NPC92
0.8125	Intermediate Similarity	NPC469663
0.8116	Intermediate Similarity	NPC294226
0.8112	Intermediate Similarity	NPC469855
0.8112	Intermediate Similarity	NPC471972
0.8112	Intermediate Similarity	NPC30846
0.8112	Intermediate Similarity	NPC477209
0.8112	Intermediate Similarity	NPC471971
0.811	Intermediate Similarity	NPC268160
0.8108	Intermediate Similarity	NPC75377
0.8106	Intermediate Similarity	NPC282577
0.8106	Intermediate Similarity	NPC321402
0.8102	Intermediate Similarity	NPC312341
0.8095	Intermediate Similarity	NPC142654
0.8085	Intermediate Similarity	NPC51531
0.8085	Intermediate Similarity	NPC91887
0.8085	Intermediate Similarity	NPC149773
0.8085	Intermediate Similarity	NPC165191
0.8085	Intermediate Similarity	NPC245760
0.8085	Intermediate Similarity	NPC23667
0.8085	Intermediate Similarity	NPC157284
0.8085	Intermediate Similarity	NPC297797
0.8085	Intermediate Similarity	NPC46242
0.8085	Intermediate Similarity	NPC473479
0.8085	Intermediate Similarity	NPC114333
0.8085	Intermediate Similarity	NPC473779
0.8085	Intermediate Similarity	NPC28592
0.8085	Intermediate Similarity	NPC289358
0.8085	Intermediate Similarity	NPC5014
0.8085	Intermediate Similarity	NPC50615
0.8085	Intermediate Similarity	NPC469857
0.8085	Intermediate Similarity	NPC477849
0.8085	Intermediate Similarity	NPC42384
0.8082	Intermediate Similarity	NPC10842
0.8077	Intermediate Similarity	NPC469644
0.8074	Intermediate Similarity	NPC476536
0.8074	Intermediate Similarity	NPC30491
0.8074	Intermediate Similarity	NPC262936
0.8069	Intermediate Similarity	NPC225351
0.8062	Intermediate Similarity	NPC174087
0.8062	Intermediate Similarity	NPC477136
0.8058	Intermediate Similarity	NPC213122
0.8054	Intermediate Similarity	NPC476533
0.8047	Intermediate Similarity	NPC147179
0.8045	Intermediate Similarity	NPC273683
0.8043	Intermediate Similarity	NPC165612
0.8042	Intermediate Similarity	NPC92079
0.8041	Intermediate Similarity	NPC474191
0.8029	Intermediate Similarity	NPC99795
0.8028	Intermediate Similarity	NPC294330
0.8014	Intermediate Similarity	NPC471152
0.8013	Intermediate Similarity	NPC213401
0.8	Intermediate Similarity	NPC91694
0.8	Intermediate Similarity	NPC469856
0.8	Intermediate Similarity	NPC62051
0.8	Intermediate Similarity	NPC469854
0.8	Intermediate Similarity	NPC300603
0.7987	Intermediate Similarity	NPC124842
0.7986	Intermediate Similarity	NPC192597
0.7986	Intermediate Similarity	NPC141817
0.7986	Intermediate Similarity	NPC11314
0.7986	Intermediate Similarity	NPC227719
0.7986	Intermediate Similarity	NPC229218
0.7986	Intermediate Similarity	NPC169214
0.7986	Intermediate Similarity	NPC176030
0.7984	Intermediate Similarity	NPC471668
0.7984	Intermediate Similarity	NPC308828
0.7974	Intermediate Similarity	NPC21046
0.7972	Intermediate Similarity	NPC78987
0.7972	Intermediate Similarity	NPC82336
0.7972	Intermediate Similarity	NPC473527
0.7971	Intermediate Similarity	NPC78575
0.7971	Intermediate Similarity	NPC93015
0.7971	Intermediate Similarity	NPC85342
0.7969	Intermediate Similarity	NPC195922
0.7958	Intermediate Similarity	NPC477593
0.7956	Intermediate Similarity	NPC131684
0.7956	Intermediate Similarity	NPC206028
0.7955	Intermediate Similarity	NPC164852
0.7953	Intermediate Similarity	NPC250323
0.7941	Intermediate Similarity	NPC471077
0.7941	Intermediate Similarity	NPC473787
0.7939	Intermediate Similarity	NPC176893
0.7937	Intermediate Similarity	NPC141782
0.7933	Intermediate Similarity	NPC164912
0.7931	Intermediate Similarity	NPC100242
0.7929	Intermediate Similarity	NPC194970
0.7926	Intermediate Similarity	NPC131799
0.7926	Intermediate Similarity	NPC123506
0.7914	Intermediate Similarity	NPC59239

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 NPC291001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	922
0.2-0.3	1421
0.3-0.4	2807
0.4-0.5	2119
0.5-0.6	1138
0.6-0.7	416
0.7-0.8	34
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8451	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD3019	Approved
0.8015	Intermediate Similarity	NPD2932	Approved
0.7793	Intermediate Similarity	NPD8166	Discontinued
0.7714	Intermediate Similarity	NPD6663	Approved
0.7681	Intermediate Similarity	NPD5736	Approved
0.763	Intermediate Similarity	NPD3092	Approved
0.7594	Intermediate Similarity	NPD3091	Approved
0.7578	Intermediate Similarity	NPD3021	Approved
0.7578	Intermediate Similarity	NPD3022	Approved
0.7569	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3026	Approved
0.7556	Intermediate Similarity	NPD3023	Approved
0.7537	Intermediate Similarity	NPD3024	Approved
0.7537	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD3025	Approved
0.7535	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3620	Phase 2
0.7422	Intermediate Similarity	NPD2342	Discontinued
0.741	Intermediate Similarity	NPD3094	Phase 2
0.7405	Intermediate Similarity	NPD7635	Approved
0.7372	Intermediate Similarity	NPD1201	Approved
0.7338	Intermediate Similarity	NPD1283	Approved
0.7315	Intermediate Similarity	NPD7003	Approved
0.7305	Intermediate Similarity	NPD9494	Approved
0.7292	Intermediate Similarity	NPD943	Approved
0.7286	Intermediate Similarity	NPD1470	Approved
0.7285	Intermediate Similarity	NPD7390	Discontinued
0.7279	Intermediate Similarity	NPD5406	Approved
0.7279	Intermediate Similarity	NPD5404	Approved
0.7279	Intermediate Similarity	NPD5405	Approved
0.7279	Intermediate Similarity	NPD5408	Approved
0.7226	Intermediate Similarity	NPD4059	Approved
0.7226	Intermediate Similarity	NPD3095	Discontinued
0.7205	Intermediate Similarity	NPD6232	Discontinued
0.7178	Intermediate Similarity	NPD7473	Discontinued
0.7177	Intermediate Similarity	NPD1809	Phase 2
0.7164	Intermediate Similarity	NPD5951	Approved
0.7162	Intermediate Similarity	NPD6099	Approved
0.7162	Intermediate Similarity	NPD6100	Approved
0.7161	Intermediate Similarity	NPD7458	Discontinued
0.7153	Intermediate Similarity	NPD1651	Approved
0.7152	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6234	Discontinued
0.7122	Intermediate Similarity	NPD1281	Approved
0.7095	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4060	Phase 1
0.7037	Intermediate Similarity	NPD2629	Approved
0.7025	Intermediate Similarity	NPD37	Approved
0.7008	Intermediate Similarity	NPD3020	Approved
0.6993	Remote Similarity	NPD3300	Phase 2
0.6984	Remote Similarity	NPD288	Approved
0.6978	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4626	Approved
0.6963	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4097	Suspended
0.694	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2979	Phase 3
0.6934	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6190	Approved
0.6917	Remote Similarity	NPD4750	Phase 3
0.6905	Remote Similarity	NPD844	Approved
0.6903	Remote Similarity	NPD2532	Approved
0.6903	Remote Similarity	NPD2534	Approved
0.6903	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3645	Discontinued
0.6903	Remote Similarity	NPD2533	Approved
0.6901	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1755	Approved
0.6894	Remote Similarity	NPD4967	Phase 2
0.6894	Remote Similarity	NPD4965	Approved
0.6894	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4966	Approved
0.6892	Remote Similarity	NPD230	Phase 1
0.6886	Remote Similarity	NPD5844	Phase 1
0.688	Remote Similarity	NPD845	Approved
0.6871	Remote Similarity	NPD8032	Phase 2
0.6863	Remote Similarity	NPD4628	Phase 3
0.6863	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4110	Phase 3
0.6859	Remote Similarity	NPD6273	Approved
0.6857	Remote Similarity	NPD2286	Discontinued
0.6857	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD9269	Phase 2
0.6831	Remote Similarity	NPD3972	Approved
0.6828	Remote Similarity	NPD4208	Discontinued
0.6826	Remote Similarity	NPD7228	Approved
0.6825	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4140	Approved
0.6824	Remote Similarity	NPD825	Approved
0.6824	Remote Similarity	NPD826	Approved
0.6822	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2438	Suspended
0.6813	Remote Similarity	NPD1934	Approved
0.6797	Remote Similarity	NPD6674	Discontinued
0.6786	Remote Similarity	NPD4093	Discontinued
0.6786	Remote Similarity	NPD5691	Approved
0.6784	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5735	Approved
0.6776	Remote Similarity	NPD2346	Discontinued
0.6772	Remote Similarity	NPD2860	Approved
0.6772	Remote Similarity	NPD2859	Approved
0.677	Remote Similarity	NPD2801	Approved
0.6759	Remote Similarity	NPD4624	Approved
0.6759	Remote Similarity	NPD258	Approved
0.6759	Remote Similarity	NPD257	Approved
0.6743	Remote Similarity	NPD2490	Approved
0.6743	Remote Similarity	NPD2488	Approved
0.6739	Remote Similarity	NPD3317	Approved
0.6738	Remote Similarity	NPD1751	Approved
0.6735	Remote Similarity	NPD7008	Discontinued
0.6731	Remote Similarity	NPD2421	Approved
0.6731	Remote Similarity	NPD2420	Approved
0.6731	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6959	Discontinued
0.6727	Remote Similarity	NPD7199	Phase 2
0.6711	Remote Similarity	NPD2935	Discontinued
0.6711	Remote Similarity	NPD4476	Approved
0.6711	Remote Similarity	NPD2531	Phase 2
0.6711	Remote Similarity	NPD4477	Approved
0.6705	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD2934	Approved
0.6693	Remote Similarity	NPD2933	Approved
0.6691	Remote Similarity	NPD228	Approved
0.6691	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1164	Approved
0.6689	Remote Similarity	NPD3764	Approved
0.6689	Remote Similarity	NPD6798	Discontinued
0.6688	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3882	Suspended
0.6687	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5327	Phase 3
0.6667	Remote Similarity	NPD2605	Approved
0.6667	Remote Similarity	NPD2606	Approved
0.6667	Remote Similarity	NPD3657	Discovery
0.6647	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7743	Approved
0.6645	Remote Similarity	NPD7742	Approved
0.6644	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8127	Discontinued
0.6625	Remote Similarity	NPD3226	Approved
0.6624	Remote Similarity	NPD1511	Approved
0.6623	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7095	Approved
0.6622	Remote Similarity	NPD5156	Approved
0.6622	Remote Similarity	NPD5155	Approved
0.662	Remote Similarity	NPD1778	Approved
0.6619	Remote Similarity	NPD4198	Discontinued
0.6618	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6166	Phase 2
0.6607	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3635	Approved
0.6599	Remote Similarity	NPD3636	Approved
0.6599	Remote Similarity	NPD3637	Approved
0.6597	Remote Similarity	NPD1608	Approved
0.6594	Remote Similarity	NPD5283	Phase 1
0.6591	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8150	Discontinued
0.6564	Remote Similarity	NPD7819	Suspended
0.6564	Remote Similarity	NPD1465	Phase 2
0.6558	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD555	Phase 2
0.6554	Remote Similarity	NPD3594	Approved
0.6554	Remote Similarity	NPD3595	Approved
0.655	Remote Similarity	NPD5190	Phase 2
0.6549	Remote Similarity	NPD9268	Approved
0.6541	Remote Similarity	NPD1512	Approved
0.6536	Remote Similarity	NPD2799	Discontinued
0.6533	Remote Similarity	NPD259	Phase 1
0.6531	Remote Similarity	NPD2195	Approved
0.6531	Remote Similarity	NPD2194	Approved
0.6528	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6353	Approved
0.6513	Remote Similarity	NPD1607	Approved
0.651	Remote Similarity	NPD4625	Phase 3
0.651	Remote Similarity	NPD3027	Phase 3
0.6507	Remote Similarity	NPD6696	Suspended
0.6503	Remote Similarity	NPD4589	Approved
0.65	Remote Similarity	NPD7427	Discontinued
0.6491	Remote Similarity	NPD4603	Phase 2
0.6488	Remote Similarity	NPD7229	Phase 3
0.6486	Remote Similarity	NPD9569	Approved
0.6483	Remote Similarity	NPD4878	Approved
0.6481	Remote Similarity	NPD4380	Phase 2

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