NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.18
Volume:	248.481
LogP:	3.24
LogD:	3.597
LogS:	-4.045
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	5.597
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.548
MDCK Permeability:	3.219190693926066e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.717
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.939
Plasma Protein Binding (PPB):	73.24658966064453%
Volume Distribution (VD):	1.157
Pgp-substrate:	24.60492706298828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.242
CYP1A2-substrate:	0.753
CYP2C19-inhibitor:	0.165
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.487
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.134
CYP3A4-substrate:	0.323

ADMET: Excretion

Clearance (CL):	7.97
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.064
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.947
Carcinogencity:	0.065
Eye Corrosion:	0.962
Eye Irritation:	0.98
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC475704

Natural Product ID:	NPC475704
*Common Name:**	Alpha-Santalol
IUPAC Name:	(Z)-5-[(1R,3R,6S)-2,3-dimethyl-4,5,6,7-tetrahydro-1H-tricyclo[2.2.1.0^{2,6}]heptan-3-yl]-2-methylpent-2-en-1-ol
Synonyms:	(Z)-Alpha-Santalol
Standard InCHIKey:	PDEQKAVEYSOLJX-RQGDDBKYSA-N
Standard InCHI:	InChI=1S/C15H24O/c1-10(9-16)5-4-6-14(2)11-7-12-13(8-11)15(12,14)3/h5,11-13,16H,4,6-9H2,1-3H3/b10-5-/t11?,12-,13+,14-,15?/m1/s1
SMILES:	OC/C(=CCC[C@]1(C)C2C[C@@H]3C1(C)[C@@H]3C2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512210
PubChem CID:	11085337
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974602]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17691	Santalum album	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17691	Santalum album	Species	Santalaceae	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
GI50	7
MIC	8
Others	18

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	18
Organism	10
Protein Family	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3013	Cell Line	HN5	Homo sapiens	LC50	=	12200.0	nM	PMID[455073]
NPT3013	Cell Line	HN5	Homo sapiens	TGI	=	8200.0	nM	PMID[455073]
NPT3013	Cell Line	HN5	Homo sapiens	GI50	=	5300.0	nM	PMID[455073]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	IZ	=	21.6	mm	PMID[455072]
NPT452	Organism	Helicobacter pylori SS1	Helicobacter pylori SS1	IZ	=	11.5	mm	PMID[455072]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	15.6	ug.mL-1	PMID[455072]
NPT452	Organism	Helicobacter pylori SS1	Helicobacter pylori SS1	MIC	=	31.3	ug.mL-1	PMID[455072]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	7.8	ug.mL-1	PMID[455072]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	31.3	ug.mL-1	PMID[455072]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	10800.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	11600.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	9000.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	7700.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	11000.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	14000.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	9200.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	6000.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	5300.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	5400.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	7600.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	7700.0	nM	PMID[455073]
NPT3014	Protein Family	Tubulin	Sus scrofa	FC	=	7000.0	n.a.	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4600.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	3500.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	3400.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	3900.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	5500.0	nM	PMID[455073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4500.0	nM	PMID[455073]

☑ 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 NPC475704 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	186
0.1-0.2	3906
0.2-0.3	18706
0.3-0.4	10580
0.4-0.5	7476
0.5-0.6	1692
0.6-0.7	140
0.7-0.8	6
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9672	High Similarity	NPC135650
0.9492	High Similarity	NPC47840
0.9492	High Similarity	NPC234264
0.918	High Similarity	NPC124112
0.8689	High Similarity	NPC309825
0.8182	Intermediate Similarity	NPC162309
0.8028	Intermediate Similarity	NPC313185
0.7887	Intermediate Similarity	NPC309178
0.7778	Intermediate Similarity	NPC11130
0.7761	Intermediate Similarity	NPC187619
0.7746	Intermediate Similarity	NPC234527
0.7746	Intermediate Similarity	NPC14352
0.7606	Intermediate Similarity	NPC471662
0.7576	Intermediate Similarity	NPC147524
0.7536	Intermediate Similarity	NPC136813
0.7536	Intermediate Similarity	NPC308522
0.7536	Intermediate Similarity	NPC74885
0.7536	Intermediate Similarity	NPC477791
0.75	Intermediate Similarity	NPC19569
0.746	Intermediate Similarity	NPC298299
0.7432	Intermediate Similarity	NPC247325
0.7432	Intermediate Similarity	NPC244488
0.7429	Intermediate Similarity	NPC160209
0.7429	Intermediate Similarity	NPC167527
0.7424	Intermediate Similarity	NPC471081
0.7397	Intermediate Similarity	NPC471659
0.7377	Intermediate Similarity	NPC244038
0.7353	Intermediate Similarity	NPC309300
0.7353	Intermediate Similarity	NPC107540
0.7286	Intermediate Similarity	NPC114651
0.7286	Intermediate Similarity	NPC171225
0.726	Intermediate Similarity	NPC474743
0.7213	Intermediate Similarity	NPC182102
0.7213	Intermediate Similarity	NPC26960
0.7213	Intermediate Similarity	NPC200129
0.72	Intermediate Similarity	NPC310643
0.72	Intermediate Similarity	NPC471658
0.7143	Intermediate Similarity	NPC28862
0.7143	Intermediate Similarity	NPC143182
0.7143	Intermediate Similarity	NPC84694
0.7143	Intermediate Similarity	NPC30986
0.7143	Intermediate Similarity	NPC81306
0.7143	Intermediate Similarity	NPC109546
0.7143	Intermediate Similarity	NPC47982
0.7143	Intermediate Similarity	NPC209430
0.7105	Intermediate Similarity	NPC34019
0.7083	Intermediate Similarity	NPC474248
0.7077	Intermediate Similarity	NPC55412
0.7077	Intermediate Similarity	NPC249645
0.7059	Intermediate Similarity	NPC210346
0.7051	Intermediate Similarity	NPC234193
0.7049	Intermediate Similarity	NPC62755
0.7042	Intermediate Similarity	NPC68703
0.7042	Intermediate Similarity	NPC69649
0.7027	Intermediate Similarity	NPC474140
0.7013	Intermediate Similarity	NPC474216
0.7013	Intermediate Similarity	NPC85346
0.7013	Intermediate Similarity	NPC65897
0.7013	Intermediate Similarity	NPC302041
0.7	Intermediate Similarity	NPC477009
0.7	Intermediate Similarity	NPC475789
0.7	Intermediate Similarity	NPC82623
0.7	Intermediate Similarity	NPC238352
0.6986	Remote Similarity	NPC34834
0.6986	Remote Similarity	NPC254845
0.6962	Remote Similarity	NPC23852
0.6962	Remote Similarity	NPC209620
0.6962	Remote Similarity	NPC4166
0.6962	Remote Similarity	NPC264245
0.6957	Remote Similarity	NPC474155
0.6957	Remote Similarity	NPC473759
0.6957	Remote Similarity	NPC474480
0.6944	Remote Similarity	NPC224532
0.6944	Remote Similarity	NPC96484
0.6914	Remote Similarity	NPC194937
0.6914	Remote Similarity	NPC476038
0.6914	Remote Similarity	NPC474047
0.6912	Remote Similarity	NPC135648
0.6912	Remote Similarity	NPC176621
0.6901	Remote Similarity	NPC202017
0.6892	Remote Similarity	NPC469343
0.6892	Remote Similarity	NPC471660
0.6875	Remote Similarity	NPC218616
0.6875	Remote Similarity	NPC49964
0.6875	Remote Similarity	NPC189972
0.6875	Remote Similarity	NPC50964
0.6875	Remote Similarity	NPC101462
0.6875	Remote Similarity	NPC87489
0.6875	Remote Similarity	NPC311092
0.6875	Remote Similarity	NPC296701
0.6875	Remote Similarity	NPC202389
0.6857	Remote Similarity	NPC110241
0.6857	Remote Similarity	NPC96793
0.6857	Remote Similarity	NPC323424
0.6849	Remote Similarity	NPC269877
0.6849	Remote Similarity	NPC167272
0.6849	Remote Similarity	NPC473893
0.6849	Remote Similarity	NPC471560
0.6842	Remote Similarity	NPC136188
0.6842	Remote Similarity	NPC263698
0.6842	Remote Similarity	NPC471723
0.6842	Remote Similarity	NPC288035
0.6842	Remote Similarity	NPC28657
0.6842	Remote Similarity	NPC141071
0.6842	Remote Similarity	NPC162742
0.6842	Remote Similarity	NPC257347
0.6842	Remote Similarity	NPC230301
0.6842	Remote Similarity	NPC285893
0.6842	Remote Similarity	NPC304309
0.6842	Remote Similarity	NPC471468
0.6842	Remote Similarity	NPC22105
0.6842	Remote Similarity	NPC134847
0.6835	Remote Similarity	NPC209944
0.6835	Remote Similarity	NPC241290
0.6835	Remote Similarity	NPC164840
0.6829	Remote Similarity	NPC283733
0.6818	Remote Similarity	NPC48891
0.6812	Remote Similarity	NPC469728
0.6795	Remote Similarity	NPC477514
0.6795	Remote Similarity	NPC473943
0.6795	Remote Similarity	NPC312328
0.679	Remote Similarity	NPC134481
0.679	Remote Similarity	NPC470384
0.679	Remote Similarity	NPC41539
0.679	Remote Similarity	NPC317458
0.679	Remote Similarity	NPC474634
0.6786	Remote Similarity	NPC67872
0.678	Remote Similarity	NPC141777
0.678	Remote Similarity	NPC166362
0.678	Remote Similarity	NPC227670
0.6765	Remote Similarity	NPC5698
0.6757	Remote Similarity	NPC9161
0.6757	Remote Similarity	NPC49422
0.6757	Remote Similarity	NPC189745
0.6757	Remote Similarity	NPC286154
0.6753	Remote Similarity	NPC46160
0.6753	Remote Similarity	NPC129165
0.6753	Remote Similarity	NPC300324
0.6753	Remote Similarity	NPC134330
0.6753	Remote Similarity	NPC237460
0.6753	Remote Similarity	NPC321016
0.6753	Remote Similarity	NPC470362
0.6753	Remote Similarity	NPC107059
0.6753	Remote Similarity	NPC113733
0.6753	Remote Similarity	NPC189883
0.6753	Remote Similarity	NPC321381
0.6753	Remote Similarity	NPC240604
0.6753	Remote Similarity	NPC126969
0.6753	Remote Similarity	NPC202642
0.675	Remote Similarity	NPC474683
0.675	Remote Similarity	NPC82986
0.675	Remote Similarity	NPC474759
0.675	Remote Similarity	NPC474731
0.675	Remote Similarity	NPC47761
0.675	Remote Similarity	NPC474752
0.675	Remote Similarity	NPC7505
0.6714	Remote Similarity	NPC211291
0.6714	Remote Similarity	NPC133368
0.6712	Remote Similarity	NPC471238
0.6711	Remote Similarity	NPC469533
0.6711	Remote Similarity	NPC469534
0.6711	Remote Similarity	NPC201048
0.6711	Remote Similarity	NPC476366
0.6711	Remote Similarity	NPC469593
0.6707	Remote Similarity	NPC231310
0.6707	Remote Similarity	NPC185568
0.6707	Remote Similarity	NPC238485
0.6707	Remote Similarity	NPC205845
0.6667	Remote Similarity	NPC155986
0.6667	Remote Similarity	NPC251666
0.6667	Remote Similarity	NPC252809
0.6667	Remote Similarity	NPC470049
0.6667	Remote Similarity	NPC477792
0.6667	Remote Similarity	NPC81907
0.6667	Remote Similarity	NPC472465
0.6667	Remote Similarity	NPC240506
0.6667	Remote Similarity	NPC331618
0.6667	Remote Similarity	NPC66020
0.6667	Remote Similarity	NPC257191
0.6667	Remote Similarity	NPC323153
0.6667	Remote Similarity	NPC176171
0.6667	Remote Similarity	NPC214570
0.6667	Remote Similarity	NPC148163
0.6667	Remote Similarity	NPC476039
0.6667	Remote Similarity	NPC148216
0.6667	Remote Similarity	NPC198968
0.6667	Remote Similarity	NPC286669
0.6667	Remote Similarity	NPC318495
0.6667	Remote Similarity	NPC304983
0.6667	Remote Similarity	NPC222366
0.6667	Remote Similarity	NPC474884
0.6667	Remote Similarity	NPC250977
0.6667	Remote Similarity	NPC130209
0.6667	Remote Similarity	NPC232247
0.6627	Remote Similarity	NPC472931
0.6627	Remote Similarity	NPC266511
0.6627	Remote Similarity	NPC472940
0.6627	Remote Similarity	NPC471224
0.6627	Remote Similarity	NPC274448
0.6627	Remote Similarity	NPC474083

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 NPC475704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	3771
0.2-0.3	4109
0.3-0.4	713
0.4-0.5	293
0.5-0.6	75
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7077	Intermediate Similarity	NPD4219	Approved
0.6962	Remote Similarity	NPD6902	Approved
0.6849	Remote Similarity	NPD6923	Approved
0.6849	Remote Similarity	NPD6922	Approved
0.6842	Remote Similarity	NPD6942	Approved
0.6842	Remote Similarity	NPD7339	Approved
0.6757	Remote Similarity	NPD7143	Approved
0.6757	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD342	Phase 1
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6625	Remote Similarity	NPD7514	Phase 3
0.6582	Remote Similarity	NPD7145	Approved
0.6582	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD368	Approved
0.6538	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6929	Approved
0.6494	Remote Similarity	NPD6926	Approved
0.6494	Remote Similarity	NPD6924	Approved
0.6471	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4243	Approved
0.642	Remote Similarity	NPD6931	Approved
0.642	Remote Similarity	NPD7525	Registered
0.642	Remote Similarity	NPD7332	Phase 2
0.642	Remote Similarity	NPD6930	Phase 2
0.641	Remote Similarity	NPD8264	Approved
0.6375	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD6933	Approved
0.6282	Remote Similarity	NPD4785	Approved
0.6282	Remote Similarity	NPD4784	Approved
0.625	Remote Similarity	NPD6932	Approved
0.6203	Remote Similarity	NPD4190	Phase 3
0.6203	Remote Similarity	NPD5275	Approved
0.619	Remote Similarity	NPD5331	Approved
0.619	Remote Similarity	NPD6695	Phase 3
0.619	Remote Similarity	NPD5332	Approved
0.6145	Remote Similarity	NPD4790	Discontinued
0.6145	Remote Similarity	NPD6898	Phase 1
0.6118	Remote Similarity	NPD4786	Approved
0.6118	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6683	Phase 2
0.6071	Remote Similarity	NPD3667	Approved
0.6047	Remote Similarity	NPD1696	Phase 3
0.6047	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD5362	Discontinued
0.593	Remote Similarity	NPD3665	Phase 1
0.593	Remote Similarity	NPD3133	Approved
0.593	Remote Similarity	NPD3666	Approved
0.5909	Remote Similarity	NPD7750	Discontinued
0.5909	Remote Similarity	NPD7524	Approved
0.5904	Remote Similarity	NPD4195	Approved
0.5897	Remote Similarity	NPD4747	Approved
0.589	Remote Similarity	NPD4191	Approved
0.589	Remote Similarity	NPD4193	Approved
0.589	Remote Similarity	NPD4194	Approved
0.589	Remote Similarity	NPD4192	Approved
0.5862	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7509	Discontinued
0.5833	Remote Similarity	NPD4748	Discontinued
0.5824	Remote Similarity	NPD7637	Suspended
0.5806	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD3618	Phase 1
0.5795	Remote Similarity	NPD5279	Phase 3
0.5781	Remote Similarity	NPD4265	Approved
0.5778	Remote Similarity	NPD5328	Approved
0.5778	Remote Similarity	NPD4753	Phase 2
0.5769	Remote Similarity	NPD4137	Phase 3
0.5714	Remote Similarity	NPD7645	Phase 2
0.5698	Remote Similarity	NPD4223	Phase 3
0.5698	Remote Similarity	NPD4221	Approved
0.5696	Remote Similarity	NPD6939	Phase 2
0.5696	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD4691	Approved
0.5679	Remote Similarity	NPD5733	Approved
0.5679	Remote Similarity	NPD4687	Approved
0.5652	Remote Similarity	NPD7087	Discontinued
0.5652	Remote Similarity	NPD6079	Approved
0.5647	Remote Similarity	NPD4822	Approved
0.5647	Remote Similarity	NPD4820	Approved
0.5647	Remote Similarity	NPD4821	Approved
0.5647	Remote Similarity	NPD4819	Approved
0.5625	Remote Similarity	NPD5276	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