NPASS Compound

Structure

CID149455 OpenBabel06191715522D 22 24 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 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 -0.8660 -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 1.7321 0.0000 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 -1.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -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 2.5981 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 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 -3.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 22 1 6 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.011
LogD:	3.686
LogS:	-4.091
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.855
Synthetic Accessibility Score:	3.926
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.623
MDCK Permeability:	1.9647586668725125e-05
Pgp-inhibitor:	0.66
Pgp-substrate:	0.463
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	94.82117462158203%
Volume Distribution (VD):	1.208
Pgp-substrate:	5.143143177032471%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.712
CYP2C19-inhibitor:	0.145
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.382
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.606
CYP3A4-substrate:	0.763

ADMET: Excretion

Clearance (CL):	10.866
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.252
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.497
Carcinogencity:	0.047
Eye Corrosion:	0.015
Eye Irritation:	0.45
Respiratory Toxicity:	0.546

Download Data

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

Natural Product: NPC149455

Natural Product ID:	NPC149455
*Common Name:**	7Beta,18-Dihydroxydehydroabietanol
IUPAC Name:	(1R,4aS,9S,10aR)-1-(hydroxymethyl)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-9-ol
Synonyms:	7Beta,18-Dihydroxydehydroabietanol
Standard InCHIKey:	PORHOKHIMOFMMH-LWYYNNOASA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13(2)14-6-7-16-15(10-14)17(22)11-18-19(3,12-21)8-5-9-20(16,18)4/h6-7,10,13,17-18,21-22H,5,8-9,11-12H2,1-4H3/t17-,18-,19-,20+/m0/s1
SMILES:	OC[C@]1(C)CCC[C@]2([C@H]1C[C@H](O)c1c2ccc(c1)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598565
PubChem CID:	21632835
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
NPO21179	Streptomyces griseoaurantiacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10048567]
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14307	Rhizopus oryzae	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20154	Cedrus atlantica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23157	Wigandia kunthii	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14307	Rhizopus oryzae	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13308	Polycitor adriaticus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21179	Streptomyces griseoaurantiacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22530	Vigna luteola	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22147	Goniothalamus macrophyllus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20154	Cedrus atlantica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21894	Psychotria granadensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22968	Elaeocarpus serratus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15469	Myodocarpus gracilis	Species	Myodocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6953.1	Aconitum sachalinense subsp. yezoense	Subspecies	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20425	Epimedium macranthum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23194	Berberis beaniana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21704	Papaver suaveolens	Species	Papaveraceae	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

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[450847]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[450847]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[450847]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[450847]

☑ 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 NPC149455 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	243
0.1-0.2	1215
0.2-0.3	2407
0.3-0.4	7549
0.4-0.5	12587
0.5-0.6	13728
0.6-0.7	4361
0.7-0.8	503
0.8-0.85	57
0.85-0.9	38
0.9-0.95	1
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472982
1.0	High Similarity	NPC64642
0.9703	High Similarity	NPC27252
0.9703	High Similarity	NPC472979
0.97	High Similarity	NPC243601
0.951	High Similarity	NPC472980
0.9307	High Similarity	NPC19856
0.9259	High Similarity	NPC472862
0.9	High Similarity	NPC324602
0.8929	High Similarity	NPC183339
0.8929	High Similarity	NPC133389
0.8929	High Similarity	NPC234337
0.8919	High Similarity	NPC471671
0.8909	High Similarity	NPC469663
0.8909	High Similarity	NPC92
0.8839	High Similarity	NPC469644
0.8829	High Similarity	NPC304510
0.8829	High Similarity	NPC172219
0.8796	High Similarity	NPC471188
0.8796	High Similarity	NPC111108
0.8772	High Similarity	NPC369
0.8772	High Similarity	NPC293831
0.875	High Similarity	NPC469609
0.8739	High Similarity	NPC219112
0.8739	High Similarity	NPC38893
0.8739	High Similarity	NPC477137
0.8739	High Similarity	NPC308311
0.8696	High Similarity	NPC182333
0.8696	High Similarity	NPC273336
0.8667	High Similarity	NPC56168
0.8661	High Similarity	NPC477136
0.8649	High Similarity	NPC35797
0.8649	High Similarity	NPC192948
0.8649	High Similarity	NPC147179
0.8621	High Similarity	NPC77691
0.8584	High Similarity	NPC154030
0.8571	High Similarity	NPC308828
0.8559	High Similarity	NPC268160
0.8522	High Similarity	NPC328504
0.85	High Similarity	NPC220596
0.8455	Intermediate Similarity	NPC471189
0.8403	Intermediate Similarity	NPC253681
0.8403	Intermediate Similarity	NPC5486
0.8381	Intermediate Similarity	NPC289117
0.8378	Intermediate Similarity	NPC228425
0.8376	Intermediate Similarity	NPC471794
0.8364	Intermediate Similarity	NPC133308
0.8305	Intermediate Similarity	NPC307139
0.8288	Intermediate Similarity	NPC176279
0.8288	Intermediate Similarity	NPC260323
0.8261	Intermediate Similarity	NPC164649
0.8261	Intermediate Similarity	NPC48342
0.8246	Intermediate Similarity	NPC212891
0.8241	Intermediate Similarity	NPC471133
0.8241	Intermediate Similarity	NPC471186
0.8235	Intermediate Similarity	NPC128645
0.823	Intermediate Similarity	NPC195922
0.822	Intermediate Similarity	NPC71094
0.8214	Intermediate Similarity	NPC250323
0.8208	Intermediate Similarity	NPC469481
0.8198	Intermediate Similarity	NPC141782
0.8198	Intermediate Similarity	NPC475002
0.8198	Intermediate Similarity	NPC132720
0.8198	Intermediate Similarity	NPC95126
0.8182	Intermediate Similarity	NPC471077
0.8167	Intermediate Similarity	NPC87985
0.8158	Intermediate Similarity	NPC469719
0.8136	Intermediate Similarity	NPC142198
0.8136	Intermediate Similarity	NPC77569
0.812	Intermediate Similarity	NPC260832
0.812	Intermediate Similarity	NPC68339
0.812	Intermediate Similarity	NPC135467
0.8119	Intermediate Similarity	NPC1793
0.8099	Intermediate Similarity	NPC325294
0.8099	Intermediate Similarity	NPC321822
0.8087	Intermediate Similarity	NPC141001
0.8087	Intermediate Similarity	NPC242764
0.8087	Intermediate Similarity	NPC471668
0.8087	Intermediate Similarity	NPC137496
0.8087	Intermediate Similarity	NPC247858
0.8087	Intermediate Similarity	NPC474358
0.8087	Intermediate Similarity	NPC257540
0.8087	Intermediate Similarity	NPC154511
0.8087	Intermediate Similarity	NPC105141
0.8087	Intermediate Similarity	NPC474387
0.8083	Intermediate Similarity	NPC181334
0.807	Intermediate Similarity	NPC471534
0.8067	Intermediate Similarity	NPC152946
0.8065	Intermediate Similarity	NPC476847
0.8053	Intermediate Similarity	NPC46940
0.8051	Intermediate Similarity	NPC472981
0.8036	Intermediate Similarity	NPC13482
0.8033	Intermediate Similarity	NPC186889
0.8018	Intermediate Similarity	NPC11554
0.8017	Intermediate Similarity	NPC4286
0.8017	Intermediate Similarity	NPC124030
0.8017	Intermediate Similarity	NPC76119
0.8	Intermediate Similarity	NPC142326
0.8	Intermediate Similarity	NPC471187
0.8	Intermediate Similarity	NPC94751
0.8	Intermediate Similarity	NPC93843
0.7984	Intermediate Similarity	NPC196193
0.7983	Intermediate Similarity	NPC475166
0.7982	Intermediate Similarity	NPC472222
0.7982	Intermediate Similarity	NPC472221
0.7982	Intermediate Similarity	NPC715
0.7982	Intermediate Similarity	NPC315794
0.7982	Intermediate Similarity	NPC169616
0.7965	Intermediate Similarity	NPC77772
0.7965	Intermediate Similarity	NPC322753
0.7965	Intermediate Similarity	NPC95716
0.7965	Intermediate Similarity	NPC151537
0.7961	Intermediate Similarity	NPC79917
0.7951	Intermediate Similarity	NPC100414
0.7951	Intermediate Similarity	NPC43000
0.7949	Intermediate Similarity	NPC206
0.7941	Intermediate Similarity	NPC199567
0.7931	Intermediate Similarity	NPC470820
0.7928	Intermediate Similarity	NPC151477
0.792	Intermediate Similarity	NPC312341
0.7917	Intermediate Similarity	NPC478058
0.7917	Intermediate Similarity	NPC11250
0.7913	Intermediate Similarity	NPC221275
0.7909	Intermediate Similarity	NPC117115
0.7886	Intermediate Similarity	NPC108164
0.7885	Intermediate Similarity	NPC314690
0.7881	Intermediate Similarity	NPC151197
0.7881	Intermediate Similarity	NPC476645
0.7881	Intermediate Similarity	NPC93071
0.7881	Intermediate Similarity	NPC126002
0.7863	Intermediate Similarity	NPC45794
0.7863	Intermediate Similarity	NPC16030
0.7851	Intermediate Similarity	NPC198014
0.7845	Intermediate Similarity	NPC84999
0.7845	Intermediate Similarity	NPC246760
0.7833	Intermediate Similarity	NPC253627
0.7822	Intermediate Similarity	NPC474211
0.7807	Intermediate Similarity	NPC470770
0.7807	Intermediate Similarity	NPC266937
0.78	Intermediate Similarity	NPC304538
0.7797	Intermediate Similarity	NPC254233
0.7795	Intermediate Similarity	NPC227719
0.7788	Intermediate Similarity	NPC58865
0.7769	Intermediate Similarity	NPC321402
0.7759	Intermediate Similarity	NPC249270
0.7759	Intermediate Similarity	NPC12656
0.775	Intermediate Similarity	NPC259703
0.775	Intermediate Similarity	NPC32322
0.7748	Intermediate Similarity	NPC99557
0.7748	Intermediate Similarity	NPC219286
0.7742	Intermediate Similarity	NPC476536
0.7739	Intermediate Similarity	NPC302371
0.7739	Intermediate Similarity	NPC62867
0.7739	Intermediate Similarity	NPC177962
0.7731	Intermediate Similarity	NPC238582
0.7731	Intermediate Similarity	NPC323074
0.7724	Intermediate Similarity	NPC137750
0.7723	Intermediate Similarity	NPC474354
0.7717	Intermediate Similarity	NPC59239
0.7717	Intermediate Similarity	NPC321086
0.77	Intermediate Similarity	NPC172984
0.7699	Intermediate Similarity	NPC262365
0.7698	Intermediate Similarity	NPC99795
0.7686	Intermediate Similarity	NPC162935
0.7686	Intermediate Similarity	NPC249340
0.7679	Intermediate Similarity	NPC21594
0.7679	Intermediate Similarity	NPC271274
0.7672	Intermediate Similarity	NPC319803
0.7672	Intermediate Similarity	NPC317869
0.7667	Intermediate Similarity	NPC233923
0.7667	Intermediate Similarity	NPC146673
0.7667	Intermediate Similarity	NPC325544
0.7667	Intermediate Similarity	NPC318581
0.7667	Intermediate Similarity	NPC477037
0.7661	Intermediate Similarity	NPC470724
0.7658	Intermediate Similarity	NPC238696
0.7658	Intermediate Similarity	NPC475225
0.7656	Intermediate Similarity	NPC310662
0.7652	Intermediate Similarity	NPC469912
0.7638	Intermediate Similarity	NPC78575
0.7636	Intermediate Similarity	NPC51015
0.7632	Intermediate Similarity	NPC314187
0.7624	Intermediate Similarity	NPC168855
0.7623	Intermediate Similarity	NPC176208
0.7623	Intermediate Similarity	NPC121168
0.7615	Intermediate Similarity	NPC68292
0.7611	Intermediate Similarity	NPC320439
0.7607	Intermediate Similarity	NPC473137
0.7607	Intermediate Similarity	NPC186933
0.7607	Intermediate Similarity	NPC107240
0.7603	Intermediate Similarity	NPC241001
0.76	Intermediate Similarity	NPC329319
0.76	Intermediate Similarity	NPC262936
0.76	Intermediate Similarity	NPC30491
0.76	Intermediate Similarity	NPC103326
0.76	Intermediate Similarity	NPC99394
0.76	Intermediate Similarity	NPC87299
0.7589	Intermediate Similarity	NPC471350
0.7586	Intermediate Similarity	NPC471179
0.7586	Intermediate Similarity	NPC473521

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 NPC149455 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	821
0.2-0.3	1259
0.3-0.4	2911
0.4-0.5	2258
0.5-0.6	1289
0.6-0.7	343
0.7-0.8	35
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD5700	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD3091	Approved
0.8136	Intermediate Similarity	NPD3092	Approved
0.8103	Intermediate Similarity	NPD7741	Discontinued
0.7966	Intermediate Similarity	NPD3095	Discontinued
0.7869	Intermediate Similarity	NPD3094	Phase 2
0.7768	Intermediate Similarity	NPD2342	Discontinued
0.7739	Intermediate Similarity	NPD7635	Approved
0.7667	Intermediate Similarity	NPD5126	Approved
0.7667	Intermediate Similarity	NPD5125	Phase 3
0.7607	Intermediate Similarity	NPD5951	Approved
0.7521	Intermediate Similarity	NPD7725	Approved
0.7521	Intermediate Similarity	NPD4059	Approved
0.7521	Intermediate Similarity	NPD3019	Approved
0.746	Intermediate Similarity	NPD5736	Approved
0.7458	Intermediate Similarity	NPD2629	Approved
0.7455	Intermediate Similarity	NPD3020	Approved
0.7395	Intermediate Similarity	NPD4198	Discontinued
0.7377	Intermediate Similarity	NPD2932	Approved
0.7355	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD1809	Phase 2
0.7328	Intermediate Similarity	NPD4750	Phase 3
0.7315	Intermediate Similarity	NPD845	Approved
0.7273	Intermediate Similarity	NPD288	Approved
0.7252	Intermediate Similarity	NPD5735	Approved
0.7248	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6663	Approved
0.7209	Intermediate Similarity	NPD7008	Discontinued
0.7197	Intermediate Similarity	NPD4097	Suspended
0.719	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD844	Approved
0.7182	Intermediate Similarity	NPD2859	Approved
0.7182	Intermediate Similarity	NPD2860	Approved
0.7176	Intermediate Similarity	NPD4140	Approved
0.7176	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3620	Phase 2
0.7154	Intermediate Similarity	NPD1710	Approved
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.712	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4624	Approved
0.71	Intermediate Similarity	NPD9294	Approved
0.7097	Intermediate Similarity	NPD2286	Discontinued
0.7091	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2933	Approved
0.7091	Intermediate Similarity	NPD6049	Phase 2
0.7091	Intermediate Similarity	NPD2934	Approved
0.709	Intermediate Similarity	NPD7742	Approved
0.709	Intermediate Similarity	NPD7743	Approved
0.7083	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD3026	Approved
0.704	Intermediate Similarity	NPD3023	Approved
0.7034	Intermediate Similarity	NPD3022	Approved
0.7034	Intermediate Similarity	NPD3021	Approved
0.7023	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3024	Approved
0.7016	Intermediate Similarity	NPD3025	Approved
0.7016	Intermediate Similarity	NPD4093	Discontinued
0.7009	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3317	Approved
0.696	Remote Similarity	NPD4626	Approved
0.696	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1751	Approved
0.696	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4625	Phase 3
0.694	Remote Similarity	NPD6353	Approved
0.693	Remote Similarity	NPD1616	Discontinued
0.6894	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3638	Discontinued
0.6884	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.687	Remote Similarity	NPD846	Approved
0.687	Remote Similarity	NPD2605	Approved
0.687	Remote Similarity	NPD940	Approved
0.687	Remote Similarity	NPD4818	Approved
0.687	Remote Similarity	NPD4719	Phase 2
0.687	Remote Similarity	NPD4817	Approved
0.687	Remote Similarity	NPD2606	Approved
0.6861	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1201	Approved
0.6842	Remote Similarity	NPD7714	Approved
0.6842	Remote Similarity	NPD7715	Approved
0.6833	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6696	Suspended
0.6818	Remote Similarity	NPD5156	Approved
0.6818	Remote Similarity	NPD5155	Approved
0.681	Remote Similarity	NPD4229	Approved
0.681	Remote Similarity	NPD4231	Approved
0.6807	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2861	Phase 2
0.6794	Remote Similarity	NPD3635	Approved
0.6794	Remote Similarity	NPD3637	Approved
0.6794	Remote Similarity	NPD3636	Approved
0.6791	Remote Similarity	NPD2238	Phase 2
0.6786	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD41	Approved
0.6765	Remote Similarity	NPD5886	Approved
0.6757	Remote Similarity	NPD1088	Approved
0.6752	Remote Similarity	NPD3048	Approved
0.6752	Remote Similarity	NPD1237	Approved
0.6752	Remote Similarity	NPD3047	Approved
0.6752	Remote Similarity	NPD3046	Approved
0.675	Remote Similarity	NPD1792	Phase 2
0.6748	Remote Similarity	NPD497	Approved
0.6746	Remote Similarity	NPD5691	Approved
0.6744	Remote Similarity	NPD4659	Approved
0.6742	Remote Similarity	NPD3595	Approved
0.6742	Remote Similarity	NPD3594	Approved
0.6742	Remote Similarity	NPD4908	Phase 1
0.6739	Remote Similarity	NPD4725	Approved
0.6739	Remote Similarity	NPD4726	Approved
0.6739	Remote Similarity	NPD4721	Approved
0.672	Remote Similarity	NPD7610	Discontinued
0.6718	Remote Similarity	NPD2195	Approved
0.6718	Remote Similarity	NPD2194	Approved
0.6714	Remote Similarity	NPD7003	Approved
0.6697	Remote Similarity	NPD1101	Approved
0.6696	Remote Similarity	NPD2066	Phase 3
0.6695	Remote Similarity	NPD5048	Discontinued
0.6693	Remote Similarity	NPD4589	Approved
0.6692	Remote Similarity	NPD8651	Approved
0.6692	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD2228	Approved
0.6667	Remote Similarity	NPD5408	Approved
0.6667	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD496	Approved
0.6667	Remote Similarity	NPD2229	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD5404	Approved
0.6667	Remote Similarity	NPD3682	Approved
0.6667	Remote Similarity	NPD4658	Approved
0.6667	Remote Similarity	NPD3680	Approved
0.6667	Remote Similarity	NPD6010	Discontinued
0.6667	Remote Similarity	NPD5405	Approved
0.6667	Remote Similarity	NPD495	Approved
0.6667	Remote Similarity	NPD2234	Approved
0.6667	Remote Similarity	NPD498	Approved
0.6667	Remote Similarity	NPD5406	Approved
0.6667	Remote Similarity	NPD4656	Approved
0.6643	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6674	Discontinued
0.6641	Remote Similarity	NPD4103	Phase 2
0.6641	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1470	Approved
0.664	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD1242	Phase 1
0.6637	Remote Similarity	NPD4814	Discontinued
0.6637	Remote Similarity	NPD688	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7236	Approved
0.6619	Remote Similarity	NPD5763	Approved
0.6619	Remote Similarity	NPD5762	Approved
0.6615	Remote Similarity	NPD4749	Approved
0.6615	Remote Similarity	NPD6025	Phase 1
0.6614	Remote Similarity	NPD1651	Approved
0.661	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD9612	Approved
0.6609	Remote Similarity	NPD9495	Approved
0.6609	Remote Similarity	NPD9611	Approved
0.6609	Remote Similarity	NPD9609	Approved
0.6594	Remote Similarity	NPD6586	Approved
0.6594	Remote Similarity	NPD6587	Approved
0.6591	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD1610	Phase 2
0.6585	Remote Similarity	NPD6858	Approved
0.6585	Remote Similarity	NPD7094	Approved
0.6581	Remote Similarity	NPD854	Approved
0.6581	Remote Similarity	NPD855	Approved
0.6577	Remote Similarity	NPD1086	Approved
0.6577	Remote Similarity	NPD1090	Approved
0.6577	Remote Similarity	NPD1089	Approved
0.6574	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7157	Approved
0.6557	Remote Similarity	NPD4253	Approved
0.6557	Remote Similarity	NPD4254	Approved
0.6549	Remote Similarity	NPD3719	Approved
0.6549	Remote Similarity	NPD3718	Approved
0.6542	Remote Similarity	NPD3971	Phase 1
0.6538	Remote Similarity	NPD2233	Approved
0.6538	Remote Similarity	NPD2230	Approved
0.6538	Remote Similarity	NPD2232	Approved
0.6535	Remote Similarity	NPD5303	Approved
0.6535	Remote Similarity	NPD7330	Discontinued
0.6535	Remote Similarity	NPD5304	Approved
0.6528	Remote Similarity	NPD3645	Discontinued
0.6528	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1930	Approved
0.6525	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6647	Phase 2
0.6525	Remote Similarity	NPD5765	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