NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	3.137
LogD:	2.768
LogS:	-3.61
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	4.216
Fsp3:	0.667
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:	-4.674
MDCK Permeability:	1.7681884855846874e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	77.477783203125%
Volume Distribution (VD):	0.776
Pgp-substrate:	22.510597229003906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.182
CYP1A2-substrate:	0.338
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.174
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.268
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	8.918
Half-life (T1/2):	0.149

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.26
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.135
Maximum Recommended Daily Dose:	0.773
Skin Sensitization:	0.266
Carcinogencity:	0.629
Eye Corrosion:	0.319
Eye Irritation:	0.647
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC7382

Natural Product ID:	NPC7382
*Common Name:**	1Beta-Hydroxy-10Betah-Guaia-4,11-Dien-3-One
IUPAC Name:	(5R,8R,8aS)-8a-hydroxy-3,8-dimethyl-5-prop-1-en-2-yl-1,4,5,6,7,8-hexahydroazulen-2-one
Synonyms:
Standard InCHIKey:	ZRPQZLPROFXWRW-HCKVZZMMSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9(2)12-6-5-10(3)15(17)8-14(16)11(4)13(15)7-12/h10,12,17H,1,5-8H2,2-4H3/t10-,12-,15+/m1/s1
SMILES:	CC(=C)[C@@H]1CC[C@H]([C@@]2(C(=C(C)C(=O)C2)C1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505152
PubChem CID:	44566710
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002874] Guaianes

*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
NPO7630	Cyperus longus	Species	Cyperaceae	Eukaryota	n.a.	Egyptian herbal medicine	n.a.	PMID[15104485]
NPO7630	Cyperus longus	Species	Cyperaceae	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	1
Others	4

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	83000.0	nM	PMID[567412]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	58.0	%	PMID[567412]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	13.5	%	PMID[567412]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	-1.1	%	PMID[567412]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	-4.5	%	PMID[567412]

☑ 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 NPC7382 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	185
0.1-0.2	1532
0.2-0.3	8100
0.3-0.4	17067
0.4-0.5	9425
0.5-0.6	5003
0.6-0.7	1248
0.7-0.8	118
0.8-0.85	9
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9315	High Similarity	NPC476624
0.9315	High Similarity	NPC472013
0.9296	High Similarity	NPC89374
0.9167	High Similarity	NPC182848
0.8919	High Similarity	NPC476627
0.8684	High Similarity	NPC138492
0.8684	High Similarity	NPC824
0.8684	High Similarity	NPC233352
0.8611	High Similarity	NPC29328
0.8608	High Similarity	NPC476628
0.8533	High Similarity	NPC472014
0.8462	Intermediate Similarity	NPC20262
0.8462	Intermediate Similarity	NPC256750
0.8356	Intermediate Similarity	NPC469737
0.8333	Intermediate Similarity	NPC171665
0.8312	Intermediate Similarity	NPC301769
0.8312	Intermediate Similarity	NPC32758
0.831	Intermediate Similarity	NPC476626
0.8267	Intermediate Similarity	NPC77501
0.8219	Intermediate Similarity	NPC280256
0.8205	Intermediate Similarity	NPC287817
0.8205	Intermediate Similarity	NPC74445
0.8193	Intermediate Similarity	NPC170775
0.8158	Intermediate Similarity	NPC25908
0.8158	Intermediate Similarity	NPC141346
0.8158	Intermediate Similarity	NPC115719
0.8158	Intermediate Similarity	NPC473437
0.8158	Intermediate Similarity	NPC142759
0.8158	Intermediate Similarity	NPC124289
0.8108	Intermediate Similarity	NPC106309
0.8077	Intermediate Similarity	NPC471890
0.8077	Intermediate Similarity	NPC84185
0.8077	Intermediate Similarity	NPC66677
0.8049	Intermediate Similarity	NPC476043
0.8	Intermediate Similarity	NPC300940
0.8	Intermediate Similarity	NPC133844
0.7838	Intermediate Similarity	NPC67608
0.7808	Intermediate Similarity	NPC278895
0.7778	Intermediate Similarity	NPC474329
0.7778	Intermediate Similarity	NPC474304
0.7763	Intermediate Similarity	NPC275098
0.775	Intermediate Similarity	NPC164218
0.775	Intermediate Similarity	NPC45495
0.7733	Intermediate Similarity	NPC18543
0.7711	Intermediate Similarity	NPC474853
0.7711	Intermediate Similarity	NPC179006
0.7692	Intermediate Similarity	NPC472305
0.7674	Intermediate Similarity	NPC77337
0.7662	Intermediate Similarity	NPC206875
0.7647	Intermediate Similarity	NPC20603
0.7625	Intermediate Similarity	NPC7232
0.7595	Intermediate Similarity	NPC34110
0.759	Intermediate Similarity	NPC90446
0.7564	Intermediate Similarity	NPC251435
0.7564	Intermediate Similarity	NPC474011
0.747	Intermediate Similarity	NPC65350
0.7468	Intermediate Similarity	NPC151622
0.7468	Intermediate Similarity	NPC7629
0.7468	Intermediate Similarity	NPC469646
0.7468	Intermediate Similarity	NPC215481
0.7467	Intermediate Similarity	NPC476614
0.7442	Intermediate Similarity	NPC58532
0.7442	Intermediate Similarity	NPC472677
0.7442	Intermediate Similarity	NPC474854
0.7432	Intermediate Similarity	NPC197089
0.7416	Intermediate Similarity	NPC167219
0.7412	Intermediate Similarity	NPC194417
0.7407	Intermediate Similarity	NPC229204
0.7403	Intermediate Similarity	NPC288667
0.7375	Intermediate Similarity	NPC86917
0.7375	Intermediate Similarity	NPC257666
0.7375	Intermediate Similarity	NPC266193
0.7368	Intermediate Similarity	NPC469914
0.7342	Intermediate Similarity	NPC201263
0.7326	Intermediate Similarity	NPC237540
0.7317	Intermediate Similarity	NPC30675
0.7308	Intermediate Similarity	NPC247586
0.7297	Intermediate Similarity	NPC61473
0.7294	Intermediate Similarity	NPC125290
0.7284	Intermediate Similarity	NPC169095
0.7284	Intermediate Similarity	NPC471409
0.7284	Intermediate Similarity	NPC207772
0.7284	Intermediate Similarity	NPC275494
0.7284	Intermediate Similarity	NPC478122
0.7284	Intermediate Similarity	NPC19443
0.7284	Intermediate Similarity	NPC192006
0.726	Intermediate Similarity	NPC190049
0.725	Intermediate Similarity	NPC263582
0.7237	Intermediate Similarity	NPC476629
0.7229	Intermediate Similarity	NPC59994
0.7229	Intermediate Similarity	NPC136150
0.7229	Intermediate Similarity	NPC47031
0.7229	Intermediate Similarity	NPC78677
0.7222	Intermediate Similarity	NPC40206
0.7209	Intermediate Similarity	NPC472869
0.7206	Intermediate Similarity	NPC474141
0.7195	Intermediate Similarity	NPC308038
0.7191	Intermediate Similarity	NPC111114
0.7191	Intermediate Similarity	NPC300312
0.7191	Intermediate Similarity	NPC144629
0.7191	Intermediate Similarity	NPC261607
0.7179	Intermediate Similarity	NPC144627
0.7179	Intermediate Similarity	NPC84790
0.7174	Intermediate Similarity	NPC477949
0.716	Intermediate Similarity	NPC97377
0.716	Intermediate Similarity	NPC103987
0.716	Intermediate Similarity	NPC53581
0.7159	Intermediate Similarity	NPC205548
0.7143	Intermediate Similarity	NPC193347
0.7143	Intermediate Similarity	NPC7414
0.7143	Intermediate Similarity	NPC477269
0.7143	Intermediate Similarity	NPC477271
0.7143	Intermediate Similarity	NPC469325
0.7143	Intermediate Similarity	NPC477270
0.7143	Intermediate Similarity	NPC261341
0.7143	Intermediate Similarity	NPC129080
0.7125	Intermediate Similarity	NPC469669
0.7125	Intermediate Similarity	NPC469678
0.7125	Intermediate Similarity	NPC475771
0.7111	Intermediate Similarity	NPC37816
0.7111	Intermediate Similarity	NPC135776
0.7108	Intermediate Similarity	NPC104120
0.7108	Intermediate Similarity	NPC69271
0.7108	Intermediate Similarity	NPC74673
0.7108	Intermediate Similarity	NPC472301
0.7108	Intermediate Similarity	NPC476625
0.7108	Intermediate Similarity	NPC157895
0.7108	Intermediate Similarity	NPC148685
0.7093	Intermediate Similarity	NPC132629
0.7093	Intermediate Similarity	NPC15838
0.7093	Intermediate Similarity	NPC261380
0.7093	Intermediate Similarity	NPC245434
0.7079	Intermediate Similarity	NPC472866
0.7073	Intermediate Similarity	NPC62336
0.7073	Intermediate Similarity	NPC63445
0.7073	Intermediate Similarity	NPC222210
0.7073	Intermediate Similarity	NPC297996
0.7073	Intermediate Similarity	NPC475994
0.7065	Intermediate Similarity	NPC9812
0.7059	Intermediate Similarity	NPC62214
0.7045	Intermediate Similarity	NPC472870
0.7045	Intermediate Similarity	NPC72397
0.7037	Intermediate Similarity	NPC279537
0.7037	Intermediate Similarity	NPC76966
0.7037	Intermediate Similarity	NPC186554
0.7037	Intermediate Similarity	NPC271070
0.7033	Intermediate Similarity	NPC53685
0.7024	Intermediate Similarity	NPC325031
0.7024	Intermediate Similarity	NPC226068
0.7024	Intermediate Similarity	NPC275766
0.7024	Intermediate Similarity	NPC470241
0.7013	Intermediate Similarity	NPC469679
0.7013	Intermediate Similarity	NPC469688
0.7	Intermediate Similarity	NPC167049
0.7	Intermediate Similarity	NPC469691
0.7	Intermediate Similarity	NPC476705
0.6988	Remote Similarity	NPC181195
0.6988	Remote Similarity	NPC281138
0.6988	Remote Similarity	NPC258231
0.6988	Remote Similarity	NPC201225
0.6988	Remote Similarity	NPC469617
0.6988	Remote Similarity	NPC261125
0.6977	Remote Similarity	NPC165287
0.6977	Remote Similarity	NPC7927
0.6977	Remote Similarity	NPC476412
0.6977	Remote Similarity	NPC156485
0.6977	Remote Similarity	NPC19849
0.6977	Remote Similarity	NPC472865
0.6977	Remote Similarity	NPC248758
0.6977	Remote Similarity	NPC230527
0.6977	Remote Similarity	NPC472864
0.6977	Remote Similarity	NPC144258
0.6974	Remote Similarity	NPC100719
0.6974	Remote Similarity	NPC166791
0.6974	Remote Similarity	NPC322035
0.6974	Remote Similarity	NPC308294
0.6974	Remote Similarity	NPC142423
0.6966	Remote Similarity	NPC268298
0.6966	Remote Similarity	NPC32922
0.6966	Remote Similarity	NPC41217
0.6966	Remote Similarity	NPC232747
0.6962	Remote Similarity	NPC471660
0.6957	Remote Similarity	NPC192962
0.6951	Remote Similarity	NPC74995
0.6951	Remote Similarity	NPC15975
0.6951	Remote Similarity	NPC195785
0.6951	Remote Similarity	NPC61952
0.6947	Remote Similarity	NPC206079
0.6947	Remote Similarity	NPC477950
0.6941	Remote Similarity	NPC145963
0.6941	Remote Similarity	NPC85772
0.6941	Remote Similarity	NPC92226
0.6941	Remote Similarity	NPC93590
0.6933	Remote Similarity	NPC150162
0.6932	Remote Similarity	NPC287079
0.6932	Remote Similarity	NPC136948
0.6932	Remote Similarity	NPC201658
0.6923	Remote Similarity	NPC477449
0.6923	Remote Similarity	NPC477448
0.6915	Remote Similarity	NPC64742

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 NPC7382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	2336
0.2-0.3	4069
0.3-0.4	1861
0.4-0.5	478
0.5-0.6	178
0.6-0.7	32
0.7-0.8	3
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
0.7349	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7341	Phase 2
0.7294	Intermediate Similarity	NPD5363	Approved
0.7209	Intermediate Similarity	NPD4519	Discontinued
0.7209	Intermediate Similarity	NPD4623	Approved
0.72	Intermediate Similarity	NPD7331	Phase 2
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD4270	Approved
0.7143	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD4269	Approved
0.7011	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4197	Approved
0.6905	Remote Similarity	NPD4252	Approved
0.6897	Remote Similarity	NPD5329	Approved
0.6889	Remote Similarity	NPD5785	Approved
0.686	Remote Similarity	NPD5362	Discontinued
0.6824	Remote Similarity	NPD5369	Approved
0.6818	Remote Similarity	NPD4690	Approved
0.6818	Remote Similarity	NPD5690	Phase 2
0.6818	Remote Similarity	NPD4688	Approved
0.6818	Remote Similarity	NPD4693	Phase 3
0.6818	Remote Similarity	NPD4689	Approved
0.6818	Remote Similarity	NPD5786	Approved
0.6818	Remote Similarity	NPD5280	Approved
0.6818	Remote Similarity	NPD4694	Approved
0.6818	Remote Similarity	NPD5205	Approved
0.6818	Remote Similarity	NPD4138	Approved
0.6782	Remote Similarity	NPD3133	Approved
0.6782	Remote Similarity	NPD3666	Approved
0.6782	Remote Similarity	NPD3665	Phase 1
0.6774	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4518	Approved
0.66	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4753	Phase 2
0.6569	Remote Similarity	NPD6371	Approved
0.6522	Remote Similarity	NPD4096	Approved
0.6512	Remote Similarity	NPD4695	Discontinued
0.6512	Remote Similarity	NPD4819	Approved
0.6512	Remote Similarity	NPD4821	Approved
0.6512	Remote Similarity	NPD4822	Approved
0.6512	Remote Similarity	NPD4820	Approved
0.6489	Remote Similarity	NPD5282	Discontinued
0.6477	Remote Similarity	NPD7154	Phase 3
0.6452	Remote Similarity	NPD5281	Approved
0.6452	Remote Similarity	NPD5284	Approved
0.6444	Remote Similarity	NPD3618	Phase 1
0.6444	Remote Similarity	NPD5279	Phase 3
0.6437	Remote Similarity	NPD4692	Approved
0.6437	Remote Similarity	NPD4139	Approved
0.6395	Remote Similarity	NPD4195	Approved
0.6383	Remote Similarity	NPD4202	Approved
0.6364	Remote Similarity	NPD3667	Approved
0.6333	Remote Similarity	NPD1696	Phase 3
0.6322	Remote Similarity	NPD5368	Approved
0.6292	Remote Similarity	NPD4788	Approved
0.6292	Remote Similarity	NPD5332	Approved
0.6292	Remote Similarity	NPD5331	Approved
0.6279	Remote Similarity	NPD4268	Approved
0.6279	Remote Similarity	NPD4271	Approved
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD4790	Discontinued
0.625	Remote Similarity	NPD4629	Approved
0.6237	Remote Similarity	NPD1695	Approved
0.6237	Remote Similarity	NPD5328	Approved
0.6222	Remote Similarity	NPD4786	Approved
0.6211	Remote Similarity	NPD5133	Approved
0.62	Remote Similarity	NPD5211	Phase 2
0.618	Remote Similarity	NPD6435	Approved
0.618	Remote Similarity	NPD5209	Approved
0.6154	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5208	Approved
0.6122	Remote Similarity	NPD6084	Phase 2
0.6122	Remote Similarity	NPD6083	Phase 2
0.6122	Remote Similarity	NPD4755	Approved
0.6105	Remote Similarity	NPD5693	Phase 1
0.6105	Remote Similarity	NPD6079	Approved
0.6098	Remote Similarity	NPD4137	Phase 3
0.6087	Remote Similarity	NPD7521	Approved
0.6087	Remote Similarity	NPD7334	Approved
0.6087	Remote Similarity	NPD6409	Approved
0.6087	Remote Similarity	NPD7146	Approved
0.6087	Remote Similarity	NPD6684	Approved
0.6087	Remote Similarity	NPD5330	Approved
0.6078	Remote Similarity	NPD5141	Approved
0.6067	Remote Similarity	NPD857	Phase 3
0.6064	Remote Similarity	NPD6080	Approved
0.6064	Remote Similarity	NPD6904	Approved
0.6064	Remote Similarity	NPD6673	Approved
0.6061	Remote Similarity	NPD5696	Approved
0.6042	Remote Similarity	NPD5778	Approved
0.6042	Remote Similarity	NPD5779	Approved
0.6026	Remote Similarity	NPD368	Approved
0.6024	Remote Similarity	NPD4747	Approved
0.6024	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD5692	Phase 3
0.6	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD5285	Approved
0.5978	Remote Similarity	NPD1694	Approved
0.5977	Remote Similarity	NPD4756	Discovery
0.5957	Remote Similarity	NPD6903	Approved
0.5957	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5276	Approved
0.5941	Remote Similarity	NPD5223	Approved
0.5938	Remote Similarity	NPD5694	Approved
0.5938	Remote Similarity	NPD6050	Approved
0.5914	Remote Similarity	NPD6098	Approved
0.5895	Remote Similarity	NPD5370	Suspended
0.5882	Remote Similarity	NPD5091	Approved
0.5882	Remote Similarity	NPD5225	Approved
0.5882	Remote Similarity	NPD5226	Approved
0.5882	Remote Similarity	NPD5224	Approved
0.5882	Remote Similarity	NPD4633	Approved
0.587	Remote Similarity	NPD3668	Phase 3
0.5867	Remote Similarity	NPD342	Phase 1
0.5859	Remote Similarity	NPD5221	Approved
0.5859	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4697	Phase 3
0.5859	Remote Similarity	NPD5222	Approved
0.5842	Remote Similarity	NPD6404	Discontinued
0.5825	Remote Similarity	NPD5174	Approved
0.5825	Remote Similarity	NPD5175	Approved
0.5825	Remote Similarity	NPD4754	Approved
0.5816	Remote Similarity	NPD6001	Approved
0.5814	Remote Similarity	NPD4058	Approved
0.5814	Remote Similarity	NPD5733	Approved
0.5814	Remote Similarity	NPD4687	Approved
0.5811	Remote Similarity	NPD3172	Approved
0.5806	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5173	Approved
0.5794	Remote Similarity	NPD4634	Approved
0.5789	Remote Similarity	NPD6672	Approved
0.5789	Remote Similarity	NPD5737	Approved
0.5773	Remote Similarity	NPD7983	Approved
0.5773	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD7515	Phase 2
0.5766	Remote Similarity	NPD7115	Discovery
0.5765	Remote Similarity	NPD4243	Approved
0.5758	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD4249	Approved
0.5743	Remote Similarity	NPD4225	Approved
0.5733	Remote Similarity	NPD3194	Approved
0.5733	Remote Similarity	NPD3195	Phase 2
0.5733	Remote Similarity	NPD3196	Approved
0.5733	Remote Similarity	NPD4266	Approved
0.5732	Remote Similarity	NPD3704	Approved
0.573	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6101	Approved
0.5729	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4768	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5688	Remote Similarity	NPD6053	Discontinued
0.5686	Remote Similarity	NPD7639	Approved
0.5686	Remote Similarity	NPD7640	Approved
0.5684	Remote Similarity	NPD4250	Approved
0.5684	Remote Similarity	NPD4251	Approved
0.5684	Remote Similarity	NPD3573	Approved
0.567	Remote Similarity	NPD6698	Approved
0.567	Remote Similarity	NPD46	Approved
0.566	Remote Similarity	NPD5697	Approved
0.566	Remote Similarity	NPD5701	Approved
0.5657	Remote Similarity	NPD7748	Approved
0.5641	Remote Similarity	NPD287	Approved
0.5632	Remote Similarity	NPD4785	Approved
0.5632	Remote Similarity	NPD4784	Approved
0.5632	Remote Similarity	NPD6926	Approved
0.5632	Remote Similarity	NPD6924	Approved
0.5612	Remote Similarity	NPD7637	Suspended
0.5612	Remote Similarity	NPD6411	Approved
0.561	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD5128	Approved
0.5607	Remote Similarity	NPD6881	Approved
0.5607	Remote Similarity	NPD7320	Approved
0.5607	Remote Similarity	NPD4730	Approved
0.5607	Remote Similarity	NPD6899	Approved
0.5607	Remote Similarity	NPD6011	Approved
0.5607	Remote Similarity	NPD4729	Approved
0.5604	Remote Similarity	NPD7332	Phase 2
0.5604	Remote Similarity	NPD6931	Approved
0.5604	Remote Similarity	NPD6930	Phase 2
0.56	Remote Similarity	NPD5654	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