NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	136.09
Volume:	156.545
LogP:	1.829
LogD:	1.632
LogS:	-1.21
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	1.597
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.132
MDCK Permeability:	2.774430686258711e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.061
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.867
Plasma Protein Binding (PPB):	63.943084716796875%
Volume Distribution (VD):	3.186
Pgp-substrate:	43.60904312133789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.575
CYP1A2-substrate:	0.24
CYP2C19-inhibitor:	0.207
CYP2C19-substrate:	0.523
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.176
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.319
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	7.163
Half-life (T1/2):	0.676

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.017
Drug-inuced Liver Injury (DILI):	0.077
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.232
Carcinogencity:	0.404
Eye Corrosion:	0.436
Eye Irritation:	0.989
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC133050

Natural Product ID:	NPC133050
*Common Name:**	2-Phenylpropan-2-Ol
IUPAC Name:	2-phenylpropan-2-ol
Synonyms:
Standard InCHIKey:	BDCFWIDZNLCTMF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H12O/c1-9(2,10)8-6-4-3-5-7-8/h3-7,10H,1-2H3
SMILES:	CC(c1ccccc1)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3185495
PubChem CID:	12053
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[12880307]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Stems	n.a.	n.a.	PMID[17663584]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[18186611]
NPO30193	Mycoplasma genitalium	Species	Mycoplasmataceae	Bacteria	n.a.	n.a.	n.a.	PMID[22817898]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Steamed Roots	n.a.	n.a.	PMID[26200131]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14105.3	Panax pseudo-ginseng wall. var. notoginseng (burk.) hoo et tseng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21891	Panax notoginseng	Species	Araliaceae	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
NPO17550	NPC133050	Other	Shoot	0.01	0.01	0.01	mg/100g	Database [DUKE]

☑ 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	4
Potency	4

Activity Type	# Activity
Organism	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MLC	=	0.96	%	PMID[450150]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MLC	=	0.78	%	PMID[450150]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MLC	=	0.71	%	PMID[450150]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MLC	=	0.93	%	PMID[450150]
NPT2	Others	Unspecified		Potency	n.a.	65739.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	52219	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	41479	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	58.6	nM	PubChem BioAssay data set

☑ 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 NPC133050 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	229
0.1-0.2	1910
0.2-0.3	5272
0.3-0.4	14011
0.4-0.5	12423
0.5-0.6	6626
0.6-0.7	1744
0.7-0.8	410
0.8-0.85	51
0.85-0.9	10
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC168855
0.9494	High Similarity	NPC474354
0.9375	High Similarity	NPC474211
0.9351	High Similarity	NPC328178
0.92	High Similarity	NPC189371
0.9125	High Similarity	NPC304538
0.9114	High Similarity	NPC87299
0.9114	High Similarity	NPC103326
0.9114	High Similarity	NPC99394
0.9114	High Similarity	NPC329319
0.9036	High Similarity	NPC1793
0.9	High Similarity	NPC172984
0.8987	High Similarity	NPC117180
0.8902	High Similarity	NPC93843
0.8718	High Similarity	NPC66655
0.8659	High Similarity	NPC95429
0.8608	High Similarity	NPC224544
0.8506	High Similarity	NPC306074
0.8506	High Similarity	NPC304541
0.8488	Intermediate Similarity	NPC242240
0.8488	Intermediate Similarity	NPC123273
0.8488	Intermediate Similarity	NPC258219
0.8488	Intermediate Similarity	NPC318325
0.8471	Intermediate Similarity	NPC307235
0.8471	Intermediate Similarity	NPC407
0.8471	Intermediate Similarity	NPC23167
0.8409	Intermediate Similarity	NPC55903
0.8391	Intermediate Similarity	NPC79917
0.8372	Intermediate Similarity	NPC113460
0.8372	Intermediate Similarity	NPC27974
0.8372	Intermediate Similarity	NPC199567
0.8372	Intermediate Similarity	NPC25493
0.8353	Intermediate Similarity	NPC197783
0.8353	Intermediate Similarity	NPC155393
0.8333	Intermediate Similarity	NPC108218
0.8315	Intermediate Similarity	NPC316301
0.8315	Intermediate Similarity	NPC152415
0.8315	Intermediate Similarity	NPC289769
0.8315	Intermediate Similarity	NPC27323
0.8295	Intermediate Similarity	NPC155908
0.8276	Intermediate Similarity	NPC280347
0.8276	Intermediate Similarity	NPC177420
0.8235	Intermediate Similarity	NPC243166
0.8235	Intermediate Similarity	NPC286904
0.8235	Intermediate Similarity	NPC248817
0.8235	Intermediate Similarity	NPC175313
0.8222	Intermediate Similarity	NPC8392
0.8202	Intermediate Similarity	NPC162314
0.8202	Intermediate Similarity	NPC147284
0.8202	Intermediate Similarity	NPC3358
0.8202	Intermediate Similarity	NPC210497
0.8202	Intermediate Similarity	NPC94139
0.8202	Intermediate Similarity	NPC306884
0.8202	Intermediate Similarity	NPC271440
0.8182	Intermediate Similarity	NPC55561
0.8182	Intermediate Similarity	NPC192
0.814	Intermediate Similarity	NPC211237
0.814	Intermediate Similarity	NPC198747
0.8132	Intermediate Similarity	NPC312132
0.8132	Intermediate Similarity	NPC259512
0.8118	Intermediate Similarity	NPC124436
0.8118	Intermediate Similarity	NPC265146
0.8111	Intermediate Similarity	NPC245187
0.809	Intermediate Similarity	NPC45040
0.809	Intermediate Similarity	NPC128645
0.809	Intermediate Similarity	NPC204210
0.8077	Intermediate Similarity	NPC208302
0.8068	Intermediate Similarity	NPC70436
0.8065	Intermediate Similarity	NPC72729
0.8046	Intermediate Similarity	NPC184169
0.8043	Intermediate Similarity	NPC6597
0.8043	Intermediate Similarity	NPC77492
0.8043	Intermediate Similarity	NPC225464
0.8043	Intermediate Similarity	NPC79241
0.8023	Intermediate Similarity	NPC150837
0.8022	Intermediate Similarity	NPC144682
0.8022	Intermediate Similarity	NPC26244
0.8022	Intermediate Similarity	NPC21959
0.8022	Intermediate Similarity	NPC222146
0.8	Intermediate Similarity	NPC325292
0.8	Intermediate Similarity	NPC138117
0.7978	Intermediate Similarity	NPC300017
0.7976	Intermediate Similarity	NPC475199
0.7976	Intermediate Similarity	NPC283012
0.7957	Intermediate Similarity	NPC299762
0.7957	Intermediate Similarity	NPC252821
0.7957	Intermediate Similarity	NPC122005
0.7957	Intermediate Similarity	NPC33675
0.7957	Intermediate Similarity	NPC92730
0.7955	Intermediate Similarity	NPC19680
0.7935	Intermediate Similarity	NPC473388
0.7912	Intermediate Similarity	NPC151715
0.7912	Intermediate Similarity	NPC128062
0.7912	Intermediate Similarity	NPC76938
0.7907	Intermediate Similarity	NPC99482
0.7895	Intermediate Similarity	NPC19856
0.7889	Intermediate Similarity	NPC231150
0.7889	Intermediate Similarity	NPC314690
0.7889	Intermediate Similarity	NPC270547
0.7882	Intermediate Similarity	NPC146703
0.7882	Intermediate Similarity	NPC477770
0.7872	Intermediate Similarity	NPC225506
0.7872	Intermediate Similarity	NPC469481
0.7865	Intermediate Similarity	NPC98772
0.7857	Intermediate Similarity	NPC242628
0.7849	Intermediate Similarity	NPC474073
0.7826	Intermediate Similarity	NPC313650
0.7826	Intermediate Similarity	NPC274678
0.7826	Intermediate Similarity	NPC32714
0.7812	Intermediate Similarity	NPC315794
0.7789	Intermediate Similarity	NPC154905
0.7789	Intermediate Similarity	NPC51015
0.7789	Intermediate Similarity	NPC252105
0.7789	Intermediate Similarity	NPC60373
0.7766	Intermediate Similarity	NPC128723
0.7765	Intermediate Similarity	NPC106313
0.7753	Intermediate Similarity	NPC104216
0.7742	Intermediate Similarity	NPC82664
0.7742	Intermediate Similarity	NPC216520
0.7742	Intermediate Similarity	NPC292730
0.7742	Intermediate Similarity	NPC132271
0.7742	Intermediate Similarity	NPC202986
0.7738	Intermediate Similarity	NPC164449
0.7738	Intermediate Similarity	NPC184030
0.7738	Intermediate Similarity	NPC192623
0.7732	Intermediate Similarity	NPC471133
0.7727	Intermediate Similarity	NPC322387
0.7717	Intermediate Similarity	NPC215351
0.7717	Intermediate Similarity	NPC20142
0.7708	Intermediate Similarity	NPC108497
0.7692	Intermediate Similarity	NPC78954
0.7692	Intermediate Similarity	NPC82770
0.7692	Intermediate Similarity	NPC239931
0.7684	Intermediate Similarity	NPC174911
0.7684	Intermediate Similarity	NPC211885
0.7684	Intermediate Similarity	NPC248396
0.7684	Intermediate Similarity	NPC129373
0.7684	Intermediate Similarity	NPC289117
0.7684	Intermediate Similarity	NPC48730
0.766	Intermediate Similarity	NPC156313
0.766	Intermediate Similarity	NPC260000
0.766	Intermediate Similarity	NPC152097
0.766	Intermediate Similarity	NPC164514
0.766	Intermediate Similarity	NPC229242
0.766	Intermediate Similarity	NPC303611
0.766	Intermediate Similarity	NPC32674
0.766	Intermediate Similarity	NPC475078
0.766	Intermediate Similarity	NPC108606
0.766	Intermediate Similarity	NPC290515
0.766	Intermediate Similarity	NPC226096
0.7653	Intermediate Similarity	NPC310456
0.7653	Intermediate Similarity	NPC53740
0.7647	Intermediate Similarity	NPC165212
0.764	Intermediate Similarity	NPC304760
0.7629	Intermediate Similarity	NPC475225
0.7629	Intermediate Similarity	NPC120719
0.7629	Intermediate Similarity	NPC475580
0.7629	Intermediate Similarity	NPC238696
0.7619	Intermediate Similarity	NPC469894
0.7609	Intermediate Similarity	NPC29373
0.7609	Intermediate Similarity	NPC181709
0.7604	Intermediate Similarity	NPC12221
0.7604	Intermediate Similarity	NPC25458
0.7604	Intermediate Similarity	NPC304873
0.7582	Intermediate Similarity	NPC300478
0.7582	Intermediate Similarity	NPC47950
0.7582	Intermediate Similarity	NPC312304
0.7579	Intermediate Similarity	NPC260775
0.7579	Intermediate Similarity	NPC216468
0.7579	Intermediate Similarity	NPC51333
0.7579	Intermediate Similarity	NPC80027
0.7579	Intermediate Similarity	NPC78119
0.7579	Intermediate Similarity	NPC132078
0.7579	Intermediate Similarity	NPC217621
0.7579	Intermediate Similarity	NPC280869
0.7576	Intermediate Similarity	NPC27252
0.7576	Intermediate Similarity	NPC66834
0.7576	Intermediate Similarity	NPC472980
0.7576	Intermediate Similarity	NPC472979
0.7558	Intermediate Similarity	NPC73637
0.7558	Intermediate Similarity	NPC121478
0.7551	Intermediate Similarity	NPC138942
0.7551	Intermediate Similarity	NPC243601
0.7551	Intermediate Similarity	NPC47284
0.7526	Intermediate Similarity	NPC146798
0.7526	Intermediate Similarity	NPC313030
0.7526	Intermediate Similarity	NPC53051
0.7526	Intermediate Similarity	NPC269212
0.7526	Intermediate Similarity	NPC71002
0.7526	Intermediate Similarity	NPC222522
0.7526	Intermediate Similarity	NPC168303
0.7526	Intermediate Similarity	NPC242342
0.7526	Intermediate Similarity	NPC302219
0.7526	Intermediate Similarity	NPC471228
0.7526	Intermediate Similarity	NPC24404
0.7526	Intermediate Similarity	NPC94351
0.7526	Intermediate Similarity	NPC235762
0.7526	Intermediate Similarity	NPC85479
0.7526	Intermediate Similarity	NPC106396
0.7526	Intermediate Similarity	NPC168829

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 NPC133050 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	1069
0.2-0.3	1370
0.3-0.4	3106
0.4-0.5	1968
0.5-0.6	995
0.6-0.7	291
0.7-0.8	63
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8718	High Similarity	NPD9294	Approved
0.8409	Intermediate Similarity	NPD845	Approved
0.8315	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD288	Approved
0.8118	Intermediate Similarity	NPD111	Approved
0.8065	Intermediate Similarity	NPD1616	Discontinued
0.8022	Intermediate Similarity	NPD2860	Approved
0.8022	Intermediate Similarity	NPD844	Approved
0.8022	Intermediate Similarity	NPD1809	Phase 2
0.8022	Intermediate Similarity	NPD2859	Approved
0.7979	Intermediate Similarity	NPD4818	Approved
0.7979	Intermediate Similarity	NPD4817	Approved
0.7957	Intermediate Similarity	NPD3020	Approved
0.7912	Intermediate Similarity	NPD2933	Approved
0.7912	Intermediate Similarity	NPD2934	Approved
0.7872	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4658	Approved
0.7708	Intermediate Similarity	NPD3683	Approved
0.7708	Intermediate Similarity	NPD3680	Approved
0.7708	Intermediate Similarity	NPD4656	Approved
0.7708	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3682	Approved
0.7708	Intermediate Similarity	NPD4231	Approved
0.7708	Intermediate Similarity	NPD3681	Approved
0.7708	Intermediate Similarity	NPD4229	Approved
0.7692	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD9612	Approved
0.766	Intermediate Similarity	NPD9609	Approved
0.766	Intermediate Similarity	NPD9611	Approved
0.764	Intermediate Similarity	NPD1101	Approved
0.7604	Intermediate Similarity	NPD940	Approved
0.7604	Intermediate Similarity	NPD846	Approved
0.7475	Intermediate Similarity	NPD1444	Approved
0.7475	Intermediate Similarity	NPD1445	Approved
0.7474	Intermediate Similarity	NPD9495	Approved
0.7473	Intermediate Similarity	NPD1090	Approved
0.7473	Intermediate Similarity	NPD1089	Approved
0.7473	Intermediate Similarity	NPD1086	Approved
0.7471	Intermediate Similarity	NPD9491	Approved
0.7449	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD9250	Approved
0.7423	Intermediate Similarity	NPD854	Approved
0.7423	Intermediate Similarity	NPD855	Approved
0.7391	Intermediate Similarity	NPD530	Approved
0.7363	Intermediate Similarity	NPD800	Approved
0.7353	Intermediate Similarity	NPD4253	Approved
0.7353	Intermediate Similarity	NPD4254	Approved
0.734	Intermediate Similarity	NPD1693	Approved
0.7327	Intermediate Similarity	NPD4717	Approved
0.7327	Intermediate Similarity	NPD4718	Approved
0.7327	Intermediate Similarity	NPD4720	Approved
0.7312	Intermediate Similarity	NPD752	Approved
0.7312	Intermediate Similarity	NPD1088	Approved
0.7283	Intermediate Similarity	NPD9258	Approved
0.7283	Intermediate Similarity	NPD9256	Approved
0.7282	Intermediate Similarity	NPD2499	Approved
0.7282	Intermediate Similarity	NPD2500	Approved
0.7273	Intermediate Similarity	NPD9610	Approved
0.7273	Intermediate Similarity	NPD310	Approved
0.7273	Intermediate Similarity	NPD309	Approved
0.7273	Intermediate Similarity	NPD9608	Approved
0.7273	Intermediate Similarity	NPD1237	Approved
0.7273	Intermediate Similarity	NPD315	Approved
0.7273	Intermediate Similarity	NPD10	Approved
0.7273	Intermediate Similarity	NPD311	Approved
0.7273	Intermediate Similarity	NPD314	Approved
0.7255	Intermediate Similarity	NPD1792	Phase 2
0.7255	Intermediate Similarity	NPD3022	Approved
0.7255	Intermediate Similarity	NPD3021	Approved
0.7253	Intermediate Similarity	NPD531	Approved
0.7241	Intermediate Similarity	NPD226	Approved
0.7234	Intermediate Similarity	NPD720	Approved
0.7234	Intermediate Similarity	NPD719	Approved
0.7234	Intermediate Similarity	NPD1409	Phase 3
0.7229	Intermediate Similarity	NPD9087	Approved
0.7228	Intermediate Similarity	NPD2342	Discontinued
0.7204	Intermediate Similarity	NPD1239	Approved
0.7143	Intermediate Similarity	NPD2229	Approved
0.7143	Intermediate Similarity	NPD9538	Approved
0.7143	Intermediate Similarity	NPD9716	Approved
0.7143	Intermediate Similarity	NPD2228	Approved
0.7143	Intermediate Similarity	NPD1087	Approved
0.7143	Intermediate Similarity	NPD2234	Approved
0.7128	Intermediate Similarity	NPD9251	Approved
0.7111	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4750	Phase 3
0.7079	Intermediate Similarity	NPD3971	Phase 1
0.7059	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7635	Approved
0.7041	Intermediate Similarity	NPD9712	Approved
0.7041	Intermediate Similarity	NPD2066	Phase 3
0.7011	Intermediate Similarity	NPD9490	Approved
0.701	Intermediate Similarity	NPD1564	Approved
0.701	Intermediate Similarity	NPD1565	Approved
0.701	Intermediate Similarity	NPD1566	Phase 3
0.7	Intermediate Similarity	NPD1415	Approved
0.7	Intermediate Similarity	NPD9500	Approved
0.699	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5347	Phase 2
0.6989	Remote Similarity	NPD5346	Phase 2
0.6979	Remote Similarity	NPD3772	Phase 3
0.6979	Remote Similarity	NPD688	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3028	Approved
0.697	Remote Similarity	NPD2550	Approved
0.697	Remote Similarity	NPD2553	Approved
0.697	Remote Similarity	NPD2558	Approved
0.697	Remote Similarity	NPD2555	Approved
0.697	Remote Similarity	NPD2549	Approved
0.697	Remote Similarity	NPD2552	Approved
0.697	Remote Similarity	NPD1242	Phase 1
0.6962	Remote Similarity	NPD675	Discontinued
0.6957	Remote Similarity	NPD4793	Discontinued
0.6952	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9273	Approved
0.6939	Remote Similarity	NPD9711	Approved
0.6939	Remote Similarity	NPD9710	Approved
0.6931	Remote Similarity	NPD3047	Approved
0.6931	Remote Similarity	NPD3048	Approved
0.6931	Remote Similarity	NPD3046	Approved
0.6916	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD1793	Approved
0.6916	Remote Similarity	NPD1791	Approved
0.69	Remote Similarity	NPD4719	Phase 2
0.69	Remote Similarity	NPD4189	Approved
0.69	Remote Similarity	NPD4188	Approved
0.6897	Remote Similarity	NPD9088	Approved
0.6897	Remote Similarity	NPD225	Approved
0.6897	Remote Similarity	NPD227	Approved
0.6893	Remote Similarity	NPD9532	Phase 3
0.6857	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4198	Discontinued
0.6852	Remote Similarity	NPD6671	Approved
0.6848	Remote Similarity	NPD9259	Approved
0.6848	Remote Similarity	NPD9257	Approved
0.6837	Remote Similarity	NPD1875	Phase 1
0.6832	Remote Similarity	NPD1929	Approved
0.6832	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1930	Approved
0.6832	Remote Similarity	NPD6647	Phase 2
0.6827	Remote Similarity	NPD2684	Approved
0.6822	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7741	Discontinued
0.6809	Remote Similarity	NPD9249	Phase 1
0.6804	Remote Similarity	NPD4814	Discontinued
0.6796	Remote Similarity	NPD968	Approved
0.6792	Remote Similarity	NPD228	Approved
0.6789	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5909	Discontinued
0.6762	Remote Similarity	NPD5237	Approved
0.6762	Remote Similarity	NPD5239	Approved
0.6762	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5235	Approved
0.6762	Remote Similarity	NPD5240	Approved
0.6762	Remote Similarity	NPD5236	Approved
0.6759	Remote Similarity	NPD5951	Approved
0.6759	Remote Similarity	NPD2629	Approved
0.6759	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD475	Phase 2
0.6757	Remote Similarity	NPD4105	Approved
0.6757	Remote Similarity	NPD4102	Approved
0.6747	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4119	Approved
0.6731	Remote Similarity	NPD290	Approved
0.6731	Remote Similarity	NPD6406	Approved
0.6701	Remote Similarity	NPD3719	Approved
0.6701	Remote Similarity	NPD1563	Approved
0.6701	Remote Similarity	NPD3718	Approved
0.6701	Remote Similarity	NPD1202	Approved
0.6698	Remote Similarity	NPD2201	Approved
0.6697	Remote Similarity	NPD255	Approved
0.6697	Remote Similarity	NPD256	Approved
0.6696	Remote Similarity	NPD5305	Approved
0.6696	Remote Similarity	NPD5306	Approved
0.6696	Remote Similarity	NPD4059	Approved
0.6696	Remote Similarity	NPD7725	Approved
0.6667	Remote Similarity	NPD3091	Approved
0.6667	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5303	Approved
0.6667	Remote Similarity	NPD5304	Approved
0.6637	Remote Similarity	NPD4136	Approved
0.6637	Remote Similarity	NPD4135	Approved
0.6637	Remote Similarity	NPD4106	Approved
0.6636	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3524	Approved
0.6635	Remote Similarity	NPD2551	Approved
0.6635	Remote Similarity	NPD3526	Approved
0.6635	Remote Similarity	NPD2559	Approved
0.6634	Remote Similarity	NPD9248	Phase 1
0.6607	Remote Similarity	NPD1710	Approved
0.6607	Remote Similarity	NPD4093	Discontinued
0.6606	Remote Similarity	NPD9618	Approved
0.6606	Remote Similarity	NPD9614	Approved
0.6604	Remote Similarity	NPD9713	Approved
0.6602	Remote Similarity	NPD164	Approved
0.6598	Remote Similarity	NPD6690	Approved
0.6593	Remote Similarity	NPD9089	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