NPASS Compound

Structure

NPC38952 OpenBabel07101719512D 23 26 0 0 1 0 0 0 0 0999 V2000 -3.4563 1.4382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1216 3.1376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1882 -0.7277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1882 -0.7277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3118 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5016 0.0494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3118 0.4984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6882 1.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2005 0.2097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4940 1.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7984 2.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8173 1.9980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0646 0.4984 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1593 2.7511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1782 2.5578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1450 1.6115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6882 0.1384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0646 1.2185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5129 0.8584 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4825 3.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4798 3.3109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 10 13 2 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 6 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 19 8 1 6 0 0 0 20 9 1 1 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	338.712
LogP:	3.979
LogD:	3.668
LogS:	-5.315
# Rotatable Bonds:	1
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	5.804
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.873
MDCK Permeability:	2.382308230153285e-05
Pgp-inhibitor:	0.887
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.191
30% Bioavailability (F30%):	0.192

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224
Plasma Protein Binding (PPB):	94.6288070678711%
Volume Distribution (VD):	1.523
Pgp-substrate:	3.2886080741882324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.176
CYP1A2-substrate:	0.858
CYP2C19-inhibitor:	0.545
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.694
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.444
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.82
CYP3A4-substrate:	0.322

ADMET: Excretion

Clearance (CL):	3.241
Half-life (T1/2):	0.146

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.314
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.308
Rat Oral Acute Toxicity:	0.45
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.336
Carcinogencity:	0.651
Eye Corrosion:	0.005
Eye Irritation:	0.686
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC38952

Natural Product ID:	NPC38952
*Common Name:**	Pachyphyllone
IUPAC Name:	n.a.
Synonyms:	Pachyphyllone
Standard InCHIKey:	UXYAZXBEJDOGCG-VHKYSDTDSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-12(2)13-10-20-9-6-14-18(3,4)7-5-8-19(14,11-23-20)17(20)16(22)15(13)21/h10,12,14,22H,5-9,11H2,1-4H3/t14-,19+,20+/m0/s1
SMILES:	CC(C)C1=C[C@]23CC[C@H]4C(C)(C)CCC[C@]4(CO3)C2=C(C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491878
PubChem CID:	44566415
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
NPO20067	Salvia pachyphylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190465]
NPO2794	Salvia clevelandii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190465]
NPO2794	Salvia clevelandii	Species	Lamiaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	GI50	=	14000.0	nM	PMID[554082]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	23000.0	nM	PMID[554082]
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	=	36000.0	nM	PMID[554082]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	32000.0	nM	PMID[554082]
NPT1723	Cell Line	HBL-100	Homo sapiens	GI50	=	22000.0	nM	PMID[554082]

☑ 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 NPC38952 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	162
0.1-0.2	1098
0.2-0.3	4069
0.3-0.4	10297
0.4-0.5	12418
0.5-0.6	7369
0.6-0.7	5548
0.7-0.8	1682
0.8-0.85	51
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC212369
0.8471	Intermediate Similarity	NPC170394
0.8352	Intermediate Similarity	NPC474396
0.8352	Intermediate Similarity	NPC210216
0.8352	Intermediate Similarity	NPC50488
0.8261	Intermediate Similarity	NPC475823
0.8261	Intermediate Similarity	NPC474209
0.8211	Intermediate Similarity	NPC73858
0.8172	Intermediate Similarity	NPC72845
0.8172	Intermediate Similarity	NPC472975
0.8111	Intermediate Similarity	NPC6185
0.8111	Intermediate Similarity	NPC241512
0.8105	Intermediate Similarity	NPC295347
0.8085	Intermediate Similarity	NPC242637
0.8065	Intermediate Similarity	NPC221111
0.8065	Intermediate Similarity	NPC280149
0.8022	Intermediate Similarity	NPC471219
0.8022	Intermediate Similarity	NPC329692
0.802	Intermediate Similarity	NPC475294
0.8	Intermediate Similarity	NPC472265
0.8	Intermediate Similarity	NPC57117
0.7957	Intermediate Similarity	NPC5509
0.7955	Intermediate Similarity	NPC476809
0.7955	Intermediate Similarity	NPC108955
0.7938	Intermediate Similarity	NPC208094
0.7938	Intermediate Similarity	NPC474343
0.7938	Intermediate Similarity	NPC170131
0.7931	Intermediate Similarity	NPC476808
0.7921	Intermediate Similarity	NPC478052
0.7917	Intermediate Similarity	NPC316215
0.7917	Intermediate Similarity	NPC183012
0.7912	Intermediate Similarity	NPC8518
0.7912	Intermediate Similarity	NPC132228
0.7912	Intermediate Similarity	NPC474680
0.7912	Intermediate Similarity	NPC133652
0.7912	Intermediate Similarity	NPC263997
0.79	Intermediate Similarity	NPC131366
0.79	Intermediate Similarity	NPC476848
0.7895	Intermediate Similarity	NPC109305
0.7872	Intermediate Similarity	NPC310479
0.7872	Intermediate Similarity	NPC182136
0.7872	Intermediate Similarity	NPC113393
0.7865	Intermediate Similarity	NPC55869
0.7849	Intermediate Similarity	NPC307298
0.7826	Intermediate Similarity	NPC472974
0.7826	Intermediate Similarity	NPC94666
0.7822	Intermediate Similarity	NPC472868
0.7812	Intermediate Similarity	NPC23170
0.7812	Intermediate Similarity	NPC476415
0.7802	Intermediate Similarity	NPC237712
0.7802	Intermediate Similarity	NPC33913
0.7802	Intermediate Similarity	NPC476412
0.7789	Intermediate Similarity	NPC49420
0.7789	Intermediate Similarity	NPC186363
0.7789	Intermediate Similarity	NPC233345
0.7789	Intermediate Similarity	NPC475806
0.7778	Intermediate Similarity	NPC474012
0.7778	Intermediate Similarity	NPC155521
0.7778	Intermediate Similarity	NPC476299
0.7778	Intermediate Similarity	NPC103486
0.7766	Intermediate Similarity	NPC309603
0.7766	Intermediate Similarity	NPC168131
0.7766	Intermediate Similarity	NPC472973
0.7766	Intermediate Similarity	NPC177141
0.7766	Intermediate Similarity	NPC73995
0.7766	Intermediate Similarity	NPC119416
0.7766	Intermediate Similarity	NPC473999
0.7755	Intermediate Similarity	NPC84335
0.7755	Intermediate Similarity	NPC73911
0.7755	Intermediate Similarity	NPC253826
0.7755	Intermediate Similarity	NPC38530
0.7753	Intermediate Similarity	NPC2482
0.7745	Intermediate Similarity	NPC477125
0.7723	Intermediate Similarity	NPC179208
0.7717	Intermediate Similarity	NPC86316
0.7717	Intermediate Similarity	NPC65661
0.7717	Intermediate Similarity	NPC189311
0.7717	Intermediate Similarity	NPC106416
0.7708	Intermediate Similarity	NPC152778
0.7708	Intermediate Similarity	NPC229976
0.7708	Intermediate Similarity	NPC271652
0.7708	Intermediate Similarity	NPC472303
0.7708	Intermediate Similarity	NPC162615
0.7708	Intermediate Similarity	NPC139692
0.7708	Intermediate Similarity	NPC38232
0.7708	Intermediate Similarity	NPC205034
0.77	Intermediate Similarity	NPC472643
0.77	Intermediate Similarity	NPC472637
0.7692	Intermediate Similarity	NPC476927
0.7692	Intermediate Similarity	NPC105803
0.7692	Intermediate Similarity	NPC288281
0.7692	Intermediate Similarity	NPC22611
0.7684	Intermediate Similarity	NPC78973
0.7684	Intermediate Similarity	NPC273199
0.7684	Intermediate Similarity	NPC152467
0.7684	Intermediate Similarity	NPC253186
0.7684	Intermediate Similarity	NPC476369
0.7684	Intermediate Similarity	NPC476437
0.7684	Intermediate Similarity	NPC51486
0.7684	Intermediate Similarity	NPC48010
0.7684	Intermediate Similarity	NPC223093
0.7677	Intermediate Similarity	NPC218107
0.7677	Intermediate Similarity	NPC478056
0.7677	Intermediate Similarity	NPC316598
0.7677	Intermediate Similarity	NPC159763
0.7677	Intermediate Similarity	NPC278386
0.7677	Intermediate Similarity	NPC473154
0.7677	Intermediate Similarity	NPC124512
0.7674	Intermediate Similarity	NPC22134
0.767	Intermediate Similarity	NPC110496
0.7667	Intermediate Similarity	NPC474731
0.7667	Intermediate Similarity	NPC474759
0.7667	Intermediate Similarity	NPC473217
0.7667	Intermediate Similarity	NPC474752
0.7667	Intermediate Similarity	NPC82986
0.7667	Intermediate Similarity	NPC474085
0.7667	Intermediate Similarity	NPC474683
0.7667	Intermediate Similarity	NPC121984
0.7667	Intermediate Similarity	NPC6663
0.7667	Intermediate Similarity	NPC7505
0.766	Intermediate Similarity	NPC215831
0.766	Intermediate Similarity	NPC48107
0.7653	Intermediate Similarity	NPC94337
0.7653	Intermediate Similarity	NPC16967
0.7653	Intermediate Similarity	NPC29952
0.7642	Intermediate Similarity	NPC475524
0.7642	Intermediate Similarity	NPC100267
0.7634	Intermediate Similarity	NPC470050
0.7634	Intermediate Similarity	NPC20688
0.7634	Intermediate Similarity	NPC327115
0.7634	Intermediate Similarity	NPC131813
0.7634	Intermediate Similarity	NPC51014
0.7634	Intermediate Similarity	NPC472985
0.7634	Intermediate Similarity	NPC474732
0.7634	Intermediate Similarity	NPC474733
0.7634	Intermediate Similarity	NPC474778
0.7634	Intermediate Similarity	NPC31564
0.7634	Intermediate Similarity	NPC145879
0.7634	Intermediate Similarity	NPC472986
0.7634	Intermediate Similarity	NPC470051
0.7629	Intermediate Similarity	NPC191521
0.7629	Intermediate Similarity	NPC245972
0.7629	Intermediate Similarity	NPC196485
0.7629	Intermediate Similarity	NPC8993
0.7629	Intermediate Similarity	NPC472976
0.7629	Intermediate Similarity	NPC279410
0.7629	Intermediate Similarity	NPC119562
0.7629	Intermediate Similarity	NPC472977
0.7624	Intermediate Similarity	NPC273005
0.7624	Intermediate Similarity	NPC469606
0.7624	Intermediate Similarity	NPC31058
0.7614	Intermediate Similarity	NPC257666
0.7614	Intermediate Similarity	NPC219809
0.7614	Intermediate Similarity	NPC266193
0.7614	Intermediate Similarity	NPC203403
0.7609	Intermediate Similarity	NPC30486
0.7609	Intermediate Similarity	NPC96055
0.7609	Intermediate Similarity	NPC53385
0.7609	Intermediate Similarity	NPC144258
0.7609	Intermediate Similarity	NPC470077
0.7604	Intermediate Similarity	NPC329842
0.7604	Intermediate Similarity	NPC185936
0.7604	Intermediate Similarity	NPC473998
0.7604	Intermediate Similarity	NPC190442
0.7604	Intermediate Similarity	NPC248913
0.7604	Intermediate Similarity	NPC472978
0.7604	Intermediate Similarity	NPC26865
0.7604	Intermediate Similarity	NPC303697
0.7604	Intermediate Similarity	NPC168027
0.7604	Intermediate Similarity	NPC289479
0.76	Intermediate Similarity	NPC201406
0.76	Intermediate Similarity	NPC471413
0.76	Intermediate Similarity	NPC117685
0.76	Intermediate Similarity	NPC472644
0.7596	Intermediate Similarity	NPC189075
0.7596	Intermediate Similarity	NPC472825
0.7596	Intermediate Similarity	NPC177064
0.7596	Intermediate Similarity	NPC275539
0.7582	Intermediate Similarity	NPC471218
0.7582	Intermediate Similarity	NPC92226
0.7582	Intermediate Similarity	NPC48362
0.7582	Intermediate Similarity	NPC470049
0.7582	Intermediate Similarity	NPC151519
0.7579	Intermediate Similarity	NPC472475
0.7579	Intermediate Similarity	NPC472240
0.7579	Intermediate Similarity	NPC326627
0.7579	Intermediate Similarity	NPC174342
0.7579	Intermediate Similarity	NPC472477
0.7579	Intermediate Similarity	NPC146554
0.7579	Intermediate Similarity	NPC76879
0.7579	Intermediate Similarity	NPC82876
0.7579	Intermediate Similarity	NPC310010
0.7579	Intermediate Similarity	NPC68148
0.7579	Intermediate Similarity	NPC65615
0.7579	Intermediate Similarity	NPC474245
0.7579	Intermediate Similarity	NPC36668
0.7579	Intermediate Similarity	NPC118011
0.7579	Intermediate Similarity	NPC262858
0.7576	Intermediate Similarity	NPC76266
0.7576	Intermediate Similarity	NPC151488

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 NPC38952 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1296
0.2-0.3	3782
0.3-0.4	2618
0.4-0.5	848
0.5-0.6	178
0.6-0.7	149
0.7-0.8	134
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
0.7955	Intermediate Similarity	NPD4695	Discontinued
0.7677	Intermediate Similarity	NPD4225	Approved
0.7634	Intermediate Similarity	NPD3618	Phase 1
0.7609	Intermediate Similarity	NPD4197	Approved
0.7582	Intermediate Similarity	NPD3667	Approved
0.7579	Intermediate Similarity	NPD4753	Phase 2
0.7528	Intermediate Similarity	NPD3617	Approved
0.7527	Intermediate Similarity	NPD5329	Approved
0.7527	Intermediate Similarity	NPD1696	Phase 3
0.75	Intermediate Similarity	NPD7638	Approved
0.7475	Intermediate Similarity	NPD5221	Approved
0.7475	Intermediate Similarity	NPD5222	Approved
0.7475	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5211	Phase 2
0.7447	Intermediate Similarity	NPD4623	Approved
0.7447	Intermediate Similarity	NPD4519	Discontinued
0.7447	Intermediate Similarity	NPD5690	Phase 2
0.7444	Intermediate Similarity	NPD4195	Approved
0.7426	Intermediate Similarity	NPD7639	Approved
0.7426	Intermediate Similarity	NPD4696	Approved
0.7426	Intermediate Similarity	NPD5285	Approved
0.7426	Intermediate Similarity	NPD7640	Approved
0.7426	Intermediate Similarity	NPD5286	Approved
0.7423	Intermediate Similarity	NPD5693	Phase 1
0.7423	Intermediate Similarity	NPD6079	Approved
0.7419	Intermediate Similarity	NPD3665	Phase 1
0.7419	Intermediate Similarity	NPD3133	Approved
0.7419	Intermediate Similarity	NPD4786	Approved
0.7419	Intermediate Similarity	NPD3666	Approved
0.74	Intermediate Similarity	NPD6083	Phase 2
0.74	Intermediate Similarity	NPD5173	Approved
0.74	Intermediate Similarity	NPD6084	Phase 2
0.74	Intermediate Similarity	NPD4755	Approved
0.7396	Intermediate Similarity	NPD5328	Approved
0.7391	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4221	Approved
0.7391	Intermediate Similarity	NPD4223	Phase 3
0.7374	Intermediate Similarity	NPD5210	Approved
0.7374	Intermediate Similarity	NPD4629	Approved
0.7374	Intermediate Similarity	NPD5695	Phase 3
0.7353	Intermediate Similarity	NPD5223	Approved
0.7347	Intermediate Similarity	NPD4202	Approved
0.734	Intermediate Similarity	NPD1694	Approved
0.7333	Intermediate Similarity	NPD5697	Approved
0.7327	Intermediate Similarity	NPD5696	Approved
0.7308	Intermediate Similarity	NPD5141	Approved
0.73	Intermediate Similarity	NPD4697	Phase 3
0.7292	Intermediate Similarity	NPD6672	Approved
0.7292	Intermediate Similarity	NPD5737	Approved
0.7282	Intermediate Similarity	NPD5225	Approved
0.7282	Intermediate Similarity	NPD4633	Approved
0.7282	Intermediate Similarity	NPD5224	Approved
0.7282	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD7748	Approved
0.7264	Intermediate Similarity	NPD6011	Approved
0.7264	Intermediate Similarity	NPD6881	Approved
0.7264	Intermediate Similarity	NPD6899	Approved
0.7263	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5280	Approved
0.7263	Intermediate Similarity	NPD5279	Phase 3
0.7263	Intermediate Similarity	NPD4694	Approved
0.7255	Intermediate Similarity	NPD4700	Approved
0.7238	Intermediate Similarity	NPD5739	Approved
0.7238	Intermediate Similarity	NPD7128	Approved
0.7238	Intermediate Similarity	NPD6675	Approved
0.7238	Intermediate Similarity	NPD6402	Approved
0.7212	Intermediate Similarity	NPD5175	Approved
0.7212	Intermediate Similarity	NPD5174	Approved
0.7207	Intermediate Similarity	NPD7115	Discovery
0.7196	Intermediate Similarity	NPD6012	Approved
0.7196	Intermediate Similarity	NPD6013	Approved
0.7196	Intermediate Similarity	NPD6014	Approved
0.7188	Intermediate Similarity	NPD3573	Approved
0.7172	Intermediate Similarity	NPD6399	Phase 3
0.717	Intermediate Similarity	NPD5701	Approved
0.713	Intermediate Similarity	NPD6883	Approved
0.713	Intermediate Similarity	NPD7290	Approved
0.713	Intermediate Similarity	NPD7102	Approved
0.7111	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7320	Approved
0.7083	Intermediate Similarity	NPD4693	Phase 3
0.7083	Intermediate Similarity	NPD4689	Approved
0.7083	Intermediate Similarity	NPD7146	Approved
0.7083	Intermediate Similarity	NPD4688	Approved
0.7083	Intermediate Similarity	NPD5330	Approved
0.7083	Intermediate Similarity	NPD4138	Approved
0.7083	Intermediate Similarity	NPD6409	Approved
0.7083	Intermediate Similarity	NPD7334	Approved
0.7083	Intermediate Similarity	NPD6684	Approved
0.7083	Intermediate Similarity	NPD5205	Approved
0.7083	Intermediate Similarity	NPD4690	Approved
0.7083	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7515	Phase 2
0.7064	Intermediate Similarity	NPD6649	Approved
0.7064	Intermediate Similarity	NPD8130	Phase 1
0.7064	Intermediate Similarity	NPD6847	Approved
0.7064	Intermediate Similarity	NPD6617	Approved
0.7064	Intermediate Similarity	NPD6869	Approved
0.7064	Intermediate Similarity	NPD6650	Approved
0.7059	Intermediate Similarity	NPD7902	Approved
0.7053	Intermediate Similarity	NPD3668	Phase 3
0.7048	Intermediate Similarity	NPD4754	Approved
0.7041	Intermediate Similarity	NPD6673	Approved
0.7041	Intermediate Similarity	NPD6904	Approved
0.7041	Intermediate Similarity	NPD6080	Approved
0.7041	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6372	Approved
0.7037	Intermediate Similarity	NPD6373	Approved
0.7	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD7339	Approved
0.7	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD8297	Approved
0.6947	Remote Similarity	NPD4788	Approved
0.6944	Remote Similarity	NPD5128	Approved
0.6944	Remote Similarity	NPD4730	Approved
0.6944	Remote Similarity	NPD4729	Approved
0.6939	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6903	Approved
0.6916	Remote Similarity	NPD4767	Approved
0.6916	Remote Similarity	NPD4768	Approved
0.6909	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6098	Approved
0.6882	Remote Similarity	NPD7645	Phase 2
0.6869	Remote Similarity	NPD6051	Approved
0.6863	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5251	Approved
0.6818	Remote Similarity	NPD4634	Approved
0.6818	Remote Similarity	NPD5247	Approved
0.6818	Remote Similarity	NPD5135	Approved
0.6818	Remote Similarity	NPD5248	Approved
0.6818	Remote Similarity	NPD5169	Approved
0.6818	Remote Similarity	NPD5249	Phase 3
0.6818	Remote Similarity	NPD5250	Approved
0.6818	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6274	Approved
0.6809	Remote Similarity	NPD7525	Registered
0.68	Remote Similarity	NPD5692	Phase 3
0.6792	Remote Similarity	NPD7632	Discontinued
0.6789	Remote Similarity	NPD5168	Approved
0.6786	Remote Similarity	NPD4632	Approved
0.6768	Remote Similarity	NPD5208	Approved
0.6765	Remote Similarity	NPD5282	Discontinued
0.6765	Remote Similarity	NPD7900	Approved
0.6765	Remote Similarity	NPD6001	Approved
0.6765	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6008	Approved
0.6757	Remote Similarity	NPD5217	Approved
0.6757	Remote Similarity	NPD5216	Approved
0.6757	Remote Similarity	NPD5127	Approved
0.6757	Remote Similarity	NPD5215	Approved
0.6754	Remote Similarity	NPD6317	Approved
0.6742	Remote Similarity	NPD4691	Approved
0.6733	Remote Similarity	NPD5694	Approved
0.6733	Remote Similarity	NPD6050	Approved
0.6727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6054	Approved
0.6703	Remote Similarity	NPD4784	Approved
0.6703	Remote Similarity	NPD4785	Approved
0.6696	Remote Similarity	NPD6335	Approved
0.6696	Remote Similarity	NPD6313	Approved
0.6696	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5133	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD6015	Approved
0.6638	Remote Similarity	NPD7101	Approved
0.6638	Remote Similarity	NPD7100	Approved
0.6636	Remote Similarity	NPD6686	Approved
0.6636	Remote Similarity	NPD5091	Approved
0.6634	Remote Similarity	NPD5207	Approved
0.6632	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4137	Phase 3
0.661	Remote Similarity	NPD5988	Approved
0.661	Remote Similarity	NPD6370	Approved
0.6609	Remote Similarity	NPD6009	Approved
0.6581	Remote Similarity	NPD6059	Approved
0.6581	Remote Similarity	NPD6319	Approved
0.6579	Remote Similarity	NPD5167	Approved
0.6569	Remote Similarity	NPD5284	Approved
0.6569	Remote Similarity	NPD5281	Approved
0.6556	Remote Similarity	NPD4747	Approved
0.6542	Remote Similarity	NPD4159	Approved
0.6525	Remote Similarity	NPD5983	Phase 2
0.6522	Remote Similarity	NPD6924	Approved
0.6522	Remote Similarity	NPD6926	Approved
0.6522	Remote Similarity	NPD4058	Approved
0.65	Remote Similarity	NPD7492	Approved
0.6471	Remote Similarity	NPD4096	Approved
0.6458	Remote Similarity	NPD4748	Discontinued
0.6452	Remote Similarity	NPD4190	Phase 3
0.6452	Remote Similarity	NPD5275	Approved
0.6452	Remote Similarity	NPD8264	Approved
0.6446	Remote Similarity	NPD6616	Approved
0.6436	Remote Similarity	NPD4518	Approved
0.6429	Remote Similarity	NPD6695	Phase 3

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