NPASS Compound

Structure

NPC32832 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 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 2.5981 -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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 -0.5000 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 -1.5000 4.3301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 16 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 20 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 6 0 0 0 19 20 1 1 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.27
Volume:	361.097
LogP:	2.764
LogD:	2.927
LogS:	-3.815
# Rotatable Bonds:	5
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.676
Synthetic Accessibility Score:	4.431
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.438
MDCK Permeability:	2.2375976186594926e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.839
Plasma Protein Binding (PPB):	59.87958526611328%
Volume Distribution (VD):	1.227
Pgp-substrate:	27.68383026123047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.267
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.465
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.261
CYP3A4-inhibitor:	0.228
CYP3A4-substrate:	0.348

ADMET: Excretion

Clearance (CL):	5.224
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.919
Carcinogencity:	0.143
Eye Corrosion:	0.03
Eye Irritation:	0.765
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC32832

Natural Product ID:	NPC32832
*Common Name:**	(Z)-2-(2-((1R,2R,4As,8As)-1-Hydroxy-2,5,5,8A-Tetramethyldecahydronaphthalen-1-Yl)Ethyl)But-2-Ene-1,4-Diol
IUPAC Name:	(Z)-2-[2-[(1R,2R,4aS,8aS)-1-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-yl]ethyl]but-2-ene-1,4-diol
Synonyms:
Standard InCHIKey:	NNDLUXBYTPAACV-VFRSJJQYSA-N
Standard InCHI:	InChI=1S/C20H36O3/c1-15-6-7-17-18(2,3)10-5-11-19(17,4)20(15,23)12-8-16(14-22)9-13-21/h9,15,17,21-23H,5-8,10-14H2,1-4H3/b16-9-/t15-,17+,19+,20-/m1/s1
SMILES:	OC/C=C(/CC[C@@]1(O)[C@H](C)CC[C@@H]2[C@]1(C)CCCC2(C)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431869
PubChem CID:	71607614
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
NPO32859	leucas stelligera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24117130]

☑ 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	1
Others	9

Activity Type	# Activity
Cell Line	6
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	21.48	%	PMID[476624]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	9.07	%	PMID[476624]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	3.54	%	PMID[476624]
NPT19	Organism	Escherichia coli	Escherichia coli	GI	=	11.47	%	PMID[476624]
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	Inhibition	=	30.57	%	PMID[476624]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	IC90	=	46.52	ug.mL-1	PMID[476624]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	IC50	=	9.8	ug.mL-1	PMID[476624]

☑ 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 NPC32832 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	176
0.1-0.2	1442
0.2-0.3	5528
0.3-0.4	15127
0.4-0.5	9379
0.5-0.6	6352
0.6-0.7	3593
0.7-0.8	901
0.8-0.85	159
0.85-0.9	26
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9571	High Similarity	NPC476366
0.9571	High Similarity	NPC201048
0.9306	High Similarity	NPC470749
0.9296	High Similarity	NPC306727
0.9178	High Similarity	NPC470711
0.9178	High Similarity	NPC470758
0.9014	High Similarity	NPC167706
0.8986	High Similarity	NPC69649
0.8986	High Similarity	NPC68703
0.8947	High Similarity	NPC476646
0.8947	High Similarity	NPC249423
0.8919	High Similarity	NPC91594
0.8873	High Similarity	NPC34834
0.8816	High Similarity	NPC96362
0.8784	High Similarity	NPC253190
0.8784	High Similarity	NPC265588
0.8696	High Similarity	NPC258595
0.8667	High Similarity	NPC471798
0.8667	High Similarity	NPC130136
0.8625	High Similarity	NPC6391
0.8625	High Similarity	NPC261266
0.8611	High Similarity	NPC283316
0.8592	High Similarity	NPC245795
0.859	High Similarity	NPC296701
0.859	High Similarity	NPC2524
0.859	High Similarity	NPC218616
0.859	High Similarity	NPC155521
0.8571	High Similarity	NPC295131
0.8571	High Similarity	NPC476406
0.8553	High Similarity	NPC11908
0.8519	High Similarity	NPC476948
0.85	High Similarity	NPC470360
0.8493	Intermediate Similarity	NPC23954
0.8472	Intermediate Similarity	NPC9942
0.8462	Intermediate Similarity	NPC209620
0.8462	Intermediate Similarity	NPC23852
0.8451	Intermediate Similarity	NPC269077
0.8451	Intermediate Similarity	NPC117607
0.8451	Intermediate Similarity	NPC253303
0.8451	Intermediate Similarity	NPC101307
0.8451	Intermediate Similarity	NPC88454
0.8442	Intermediate Similarity	NPC30986
0.8442	Intermediate Similarity	NPC209430
0.8442	Intermediate Similarity	NPC472463
0.8421	Intermediate Similarity	NPC132542
0.8415	Intermediate Similarity	NPC133588
0.8395	Intermediate Similarity	NPC299068
0.8378	Intermediate Similarity	NPC265485
0.8378	Intermediate Similarity	NPC220939
0.8378	Intermediate Similarity	NPC474743
0.8378	Intermediate Similarity	NPC182717
0.8354	Intermediate Similarity	NPC49964
0.8354	Intermediate Similarity	NPC87489
0.8354	Intermediate Similarity	NPC50964
0.8333	Intermediate Similarity	NPC96484
0.8333	Intermediate Similarity	NPC281880
0.8333	Intermediate Similarity	NPC266578
0.8333	Intermediate Similarity	NPC94192
0.8313	Intermediate Similarity	NPC470361
0.8312	Intermediate Similarity	NPC83351
0.8312	Intermediate Similarity	NPC476314
0.8312	Intermediate Similarity	NPC167891
0.8312	Intermediate Similarity	NPC285761
0.831	Intermediate Similarity	NPC279434
0.8289	Intermediate Similarity	NPC247325
0.8289	Intermediate Similarity	NPC244488
0.8289	Intermediate Similarity	NPC63958
0.8286	Intermediate Similarity	NPC225415
0.8286	Intermediate Similarity	NPC101128
0.8267	Intermediate Similarity	NPC477138
0.8267	Intermediate Similarity	NPC100334
0.8267	Intermediate Similarity	NPC243342
0.8267	Intermediate Similarity	NPC91858
0.825	Intermediate Similarity	NPC476927
0.825	Intermediate Similarity	NPC82623
0.8243	Intermediate Similarity	NPC164022
0.8243	Intermediate Similarity	NPC477792
0.8243	Intermediate Similarity	NPC471272
0.8243	Intermediate Similarity	NPC242001
0.8228	Intermediate Similarity	NPC264245
0.8228	Intermediate Similarity	NPC242350
0.8228	Intermediate Similarity	NPC159148
0.8219	Intermediate Similarity	NPC476431
0.8219	Intermediate Similarity	NPC471560
0.8219	Intermediate Similarity	NPC234511
0.8219	Intermediate Similarity	NPC474248
0.8214	Intermediate Similarity	NPC204188
0.8214	Intermediate Similarity	NPC329596
0.8214	Intermediate Similarity	NPC3345
0.8214	Intermediate Similarity	NPC295668
0.8214	Intermediate Similarity	NPC291484
0.8214	Intermediate Similarity	NPC80561
0.8214	Intermediate Similarity	NPC11216
0.8205	Intermediate Similarity	NPC273410
0.8205	Intermediate Similarity	NPC80530
0.8205	Intermediate Similarity	NPC84694
0.8205	Intermediate Similarity	NPC47982
0.8205	Intermediate Similarity	NPC81306
0.8205	Intermediate Similarity	NPC28862
0.8205	Intermediate Similarity	NPC143182
0.8205	Intermediate Similarity	NPC109546
0.8205	Intermediate Similarity	NPC291379
0.8194	Intermediate Similarity	NPC114651
0.8194	Intermediate Similarity	NPC197805
0.8194	Intermediate Similarity	NPC171225
0.8193	Intermediate Similarity	NPC474668
0.8182	Intermediate Similarity	NPC472805
0.8182	Intermediate Similarity	NPC40394
0.8182	Intermediate Similarity	NPC31037
0.8182	Intermediate Similarity	NPC101475
0.8182	Intermediate Similarity	NPC90979
0.8182	Intermediate Similarity	NPC157996
0.8182	Intermediate Similarity	NPC34177
0.8171	Intermediate Similarity	NPC293287
0.8171	Intermediate Similarity	NPC152808
0.8171	Intermediate Similarity	NPC175145
0.8171	Intermediate Similarity	NPC139724
0.8171	Intermediate Similarity	NPC475069
0.8158	Intermediate Similarity	NPC133580
0.8158	Intermediate Similarity	NPC66566
0.8158	Intermediate Similarity	NPC477923
0.8158	Intermediate Similarity	NPC291503
0.8148	Intermediate Similarity	NPC474047
0.8148	Intermediate Similarity	NPC470077
0.8148	Intermediate Similarity	NPC231310
0.8148	Intermediate Similarity	NPC83702
0.8148	Intermediate Similarity	NPC102048
0.8148	Intermediate Similarity	NPC205845
0.8148	Intermediate Similarity	NPC474493
0.8143	Intermediate Similarity	NPC81615
0.8133	Intermediate Similarity	NPC471799
0.8133	Intermediate Similarity	NPC68443
0.8133	Intermediate Similarity	NPC130665
0.8125	Intermediate Similarity	NPC202389
0.8125	Intermediate Similarity	NPC248886
0.8125	Intermediate Similarity	NPC101462
0.8125	Intermediate Similarity	NPC470049
0.8125	Intermediate Similarity	NPC304285
0.8118	Intermediate Similarity	NPC41554
0.8118	Intermediate Similarity	NPC97404
0.8108	Intermediate Similarity	NPC92801
0.8108	Intermediate Similarity	NPC145498
0.8101	Intermediate Similarity	NPC287749
0.8101	Intermediate Similarity	NPC102253
0.8101	Intermediate Similarity	NPC324772
0.8101	Intermediate Similarity	NPC234193
0.8101	Intermediate Similarity	NPC164840
0.8101	Intermediate Similarity	NPC236237
0.8101	Intermediate Similarity	NPC241290
0.8101	Intermediate Similarity	NPC13554
0.8101	Intermediate Similarity	NPC209944
0.8101	Intermediate Similarity	NPC322313
0.8095	Intermediate Similarity	NPC187785
0.8095	Intermediate Similarity	NPC259875
0.8095	Intermediate Similarity	NPC101886
0.8082	Intermediate Similarity	NPC2648
0.8082	Intermediate Similarity	NPC276616
0.8082	Intermediate Similarity	NPC471238
0.8082	Intermediate Similarity	NPC160209
0.8082	Intermediate Similarity	NPC208999
0.8077	Intermediate Similarity	NPC98386
0.8077	Intermediate Similarity	NPC99168
0.8077	Intermediate Similarity	NPC167037
0.8077	Intermediate Similarity	NPC138621
0.8077	Intermediate Similarity	NPC253807
0.8077	Intermediate Similarity	NPC472502
0.8077	Intermediate Similarity	NPC230295
0.8077	Intermediate Similarity	NPC472500
0.8077	Intermediate Similarity	NPC475
0.8077	Intermediate Similarity	NPC300499
0.8077	Intermediate Similarity	NPC158662
0.8077	Intermediate Similarity	NPC474216
0.8077	Intermediate Similarity	NPC87604
0.8077	Intermediate Similarity	NPC470396
0.8077	Intermediate Similarity	NPC474989
0.8077	Intermediate Similarity	NPC472499
0.8077	Intermediate Similarity	NPC22955
0.8077	Intermediate Similarity	NPC6978
0.8077	Intermediate Similarity	NPC196753
0.8077	Intermediate Similarity	NPC148977
0.8077	Intermediate Similarity	NPC244385
0.8056	Intermediate Similarity	NPC202017
0.8056	Intermediate Similarity	NPC149680
0.8056	Intermediate Similarity	NPC476039
0.8056	Intermediate Similarity	NPC222366
0.8056	Intermediate Similarity	NPC286669
0.8052	Intermediate Similarity	NPC120098
0.8052	Intermediate Similarity	NPC27765
0.8052	Intermediate Similarity	NPC189883
0.8052	Intermediate Similarity	NPC106432
0.8052	Intermediate Similarity	NPC30590
0.8052	Intermediate Similarity	NPC237460
0.8052	Intermediate Similarity	NPC290598
0.8052	Intermediate Similarity	NPC122418
0.8052	Intermediate Similarity	NPC265328
0.8049	Intermediate Similarity	NPC318390
0.8049	Intermediate Similarity	NPC274448
0.8028	Intermediate Similarity	NPC323424
0.8028	Intermediate Similarity	NPC96793
0.8028	Intermediate Similarity	NPC68656

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 NPC32832 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1773
0.2-0.3	4050
0.3-0.4	2211
0.4-0.5	557
0.5-0.6	260
0.6-0.7	99
0.7-0.8	40
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
0.8101	Intermediate Similarity	NPD6931	Approved
0.8101	Intermediate Similarity	NPD7525	Registered
0.8101	Intermediate Similarity	NPD6930	Phase 2
0.7975	Intermediate Similarity	NPD6929	Approved
0.7975	Intermediate Similarity	NPD7645	Phase 2
0.7875	Intermediate Similarity	NPD7514	Phase 3
0.7875	Intermediate Similarity	NPD7332	Phase 2
0.7857	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6695	Phase 3
0.7792	Intermediate Similarity	NPD6924	Approved
0.7792	Intermediate Similarity	NPD6926	Approved
0.7722	Intermediate Similarity	NPD6925	Approved
0.7722	Intermediate Similarity	NPD5776	Phase 2
0.7711	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7339	Approved
0.7692	Intermediate Similarity	NPD8264	Approved
0.7692	Intermediate Similarity	NPD6942	Approved
0.7625	Intermediate Similarity	NPD7145	Approved
0.7625	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6893	Approved
0.7595	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6933	Approved
0.7561	Intermediate Similarity	NPD6898	Phase 1
0.7561	Intermediate Similarity	NPD6902	Approved
0.7532	Intermediate Similarity	NPD4243	Approved
0.75	Intermediate Similarity	NPD368	Approved
0.75	Intermediate Similarity	NPD6932	Approved
0.7442	Intermediate Similarity	NPD7750	Discontinued
0.7442	Intermediate Similarity	NPD7524	Approved
0.7439	Intermediate Similarity	NPD7509	Discontinued
0.7342	Intermediate Similarity	NPD4785	Approved
0.7342	Intermediate Similarity	NPD4784	Approved
0.7317	Intermediate Similarity	NPD6683	Phase 2
0.7312	Intermediate Similarity	NPD7640	Approved
0.7312	Intermediate Similarity	NPD7639	Approved
0.7273	Intermediate Similarity	NPD6923	Approved
0.7273	Intermediate Similarity	NPD6922	Approved
0.7204	Intermediate Similarity	NPD7638	Approved
0.7179	Intermediate Similarity	NPD7143	Approved
0.7179	Intermediate Similarity	NPD7144	Approved
0.7143	Intermediate Similarity	NPD342	Phase 1
0.7126	Intermediate Similarity	NPD3618	Phase 1
0.7111	Intermediate Similarity	NPD7087	Discontinued
0.7093	Intermediate Similarity	NPD4786	Approved
0.7089	Intermediate Similarity	NPD7152	Approved
0.7089	Intermediate Similarity	NPD7150	Approved
0.7089	Intermediate Similarity	NPD7151	Approved
0.7079	Intermediate Similarity	NPD5328	Approved
0.7059	Intermediate Similarity	NPD3667	Approved
0.7037	Intermediate Similarity	NPD4190	Phase 3
0.7037	Intermediate Similarity	NPD5275	Approved
0.6932	Remote Similarity	NPD4623	Approved
0.6932	Remote Similarity	NPD4519	Discontinued
0.6923	Remote Similarity	NPD6079	Approved
0.6923	Remote Similarity	NPD7515	Phase 2
0.6905	Remote Similarity	NPD4195	Approved
0.6897	Remote Similarity	NPD3666	Approved
0.6897	Remote Similarity	NPD3133	Approved
0.6897	Remote Similarity	NPD3665	Phase 1
0.6848	Remote Similarity	NPD4202	Approved
0.6824	Remote Similarity	NPD4748	Discontinued
0.679	Remote Similarity	NPD4732	Discontinued
0.6739	Remote Similarity	NPD7637	Suspended
0.6703	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6633	Remote Similarity	NPD7632	Discontinued
0.6633	Remote Similarity	NPD5211	Phase 2
0.663	Remote Similarity	NPD7136	Phase 2
0.6629	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5329	Approved
0.6596	Remote Similarity	NPD7748	Approved
0.6591	Remote Similarity	NPD4788	Approved
0.6575	Remote Similarity	NPD4219	Approved
0.6562	Remote Similarity	NPD4755	Approved
0.6556	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6051	Approved
0.6517	Remote Similarity	NPD4197	Approved
0.65	Remote Similarity	NPD5141	Approved
0.6489	Remote Similarity	NPD5778	Approved
0.6489	Remote Similarity	NPD5779	Approved
0.6458	Remote Similarity	NPD4697	Phase 3
0.6458	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5221	Approved
0.6458	Remote Similarity	NPD5222	Approved
0.6444	Remote Similarity	NPD1696	Phase 3
0.6437	Remote Similarity	NPD4695	Discontinued
0.6429	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD4700	Approved
0.6429	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD4696	Approved
0.642	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7902	Approved
0.6392	Remote Similarity	NPD6083	Phase 2
0.6392	Remote Similarity	NPD5173	Approved
0.6392	Remote Similarity	NPD6084	Phase 2
0.6374	Remote Similarity	NPD5205	Approved
0.6374	Remote Similarity	NPD4688	Approved
0.6374	Remote Similarity	NPD5279	Phase 3
0.6374	Remote Similarity	NPD4690	Approved
0.6374	Remote Similarity	NPD4693	Phase 3
0.6374	Remote Similarity	NPD4138	Approved
0.6374	Remote Similarity	NPD4689	Approved
0.6364	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD5344	Discontinued
0.6354	Remote Similarity	NPD5210	Approved
0.6354	Remote Similarity	NPD4629	Approved
0.6333	Remote Similarity	NPD3668	Phase 3
0.6327	Remote Similarity	NPD5290	Discontinued
0.6316	Remote Similarity	NPD6399	Phase 3
0.63	Remote Similarity	NPD5225	Approved
0.63	Remote Similarity	NPD5226	Approved
0.63	Remote Similarity	NPD5224	Approved
0.63	Remote Similarity	NPD4633	Approved
0.6292	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6402	Approved
0.6275	Remote Similarity	NPD5739	Approved
0.6275	Remote Similarity	NPD7128	Approved
0.6275	Remote Similarity	NPD6675	Approved
0.6239	Remote Similarity	NPD7327	Approved
0.6239	Remote Similarity	NPD7328	Approved
0.6238	Remote Similarity	NPD5175	Approved
0.6238	Remote Similarity	NPD4754	Approved
0.6238	Remote Similarity	NPD5174	Approved
0.6237	Remote Similarity	NPD4723	Approved
0.6237	Remote Similarity	NPD4722	Approved
0.6207	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3617	Approved
0.62	Remote Similarity	NPD4159	Approved
0.6196	Remote Similarity	NPD5690	Phase 2
0.6196	Remote Similarity	NPD7334	Approved
0.6196	Remote Similarity	NPD6409	Approved
0.6196	Remote Similarity	NPD5280	Approved
0.6196	Remote Similarity	NPD5330	Approved
0.6196	Remote Similarity	NPD7146	Approved
0.6196	Remote Similarity	NPD6684	Approved
0.6196	Remote Similarity	NPD4694	Approved
0.6196	Remote Similarity	NPD7521	Approved
0.619	Remote Similarity	NPD4634	Approved
0.6182	Remote Similarity	NPD7516	Approved
0.6154	Remote Similarity	NPD6686	Approved
0.6154	Remote Similarity	NPD6881	Approved
0.6154	Remote Similarity	NPD7320	Approved
0.6154	Remote Similarity	NPD6899	Approved
0.6147	Remote Similarity	NPD7115	Discovery
0.6145	Remote Similarity	NPD4787	Phase 1
0.6129	Remote Similarity	NPD3573	Approved
0.6126	Remote Similarity	NPD8377	Approved
0.6126	Remote Similarity	NPD8294	Approved
0.6117	Remote Similarity	NPD4768	Approved
0.6117	Remote Similarity	NPD4767	Approved
0.6117	Remote Similarity	NPD6640	Phase 3
0.61	Remote Similarity	NPD6648	Approved
0.6095	Remote Similarity	NPD6373	Approved
0.6095	Remote Similarity	NPD6372	Approved
0.6095	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4265	Approved
0.6082	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7900	Approved
0.6071	Remote Similarity	NPD8296	Approved
0.6071	Remote Similarity	NPD8380	Approved
0.6071	Remote Similarity	NPD8033	Approved
0.6071	Remote Similarity	NPD8335	Approved
0.6071	Remote Similarity	NPD8379	Approved
0.6071	Remote Similarity	NPD7503	Approved
0.6071	Remote Similarity	NPD8378	Approved
0.6067	Remote Similarity	NPD4819	Approved
0.6067	Remote Similarity	NPD4822	Approved
0.6067	Remote Similarity	NPD4821	Approved
0.6067	Remote Similarity	NPD4820	Approved
0.6064	Remote Similarity	NPD6672	Approved
0.6064	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5737	Approved
0.6064	Remote Similarity	NPD6903	Approved
0.6058	Remote Similarity	NPD6412	Phase 2
0.6058	Remote Similarity	NPD5697	Approved
0.6058	Remote Similarity	NPD5701	Approved
0.6047	Remote Similarity	NPD3703	Phase 2
0.6042	Remote Similarity	NPD8035	Phase 2
0.6042	Remote Similarity	NPD6411	Approved
0.6042	Remote Similarity	NPD8034	Phase 2
0.6038	Remote Similarity	NPD7102	Approved
0.6038	Remote Similarity	NPD6883	Approved
0.6038	Remote Similarity	NPD7290	Approved
0.6023	Remote Similarity	NPD6114	Approved
0.6023	Remote Similarity	NPD6118	Approved
0.6023	Remote Similarity	NPD6697	Approved
0.6023	Remote Similarity	NPD6115	Approved
0.6022	Remote Similarity	NPD6098	Approved
0.602	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5695	Phase 3
0.6019	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD385	Approved
0.6	Remote Similarity	NPD4692	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD4139	Approved
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD5128	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