NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	263.425
LogP:	2.116
LogD:	1.993
LogS:	-3.86
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.696
Synthetic Accessibility Score:	5.702
Fsp3:	0.8
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:	-4.503
MDCK Permeability:	2.004203815886285e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.256
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.981
Plasma Protein Binding (PPB):	60.341209411621094%
Volume Distribution (VD):	1.141
Pgp-substrate:	39.627288818359375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.731
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.437
CYP3A4-substrate:	0.858

ADMET: Excretion

Clearance (CL):	6.922
Half-life (T1/2):	0.488

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.366
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.824
Maximum Recommended Daily Dose:	0.421
Skin Sensitization:	0.076
Carcinogencity:	0.919
Eye Corrosion:	0.081
Eye Irritation:	0.792
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC471941

Natural Product ID:	NPC471941
*Common Name:**	LUADJIBUFOIMNV-HTSBLVJZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LUADJIBUFOIMNV-HTSBLVJZSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9-4-5-11-10(9)6-15(18)12(17)7-13(11,2)14(15,3)8-16/h5,9-10,16,18H,4,6-8H2,1-3H3/t9-,10-,13+,14?,15-/m0/s1
SMILES:	CC1CC=C2C1CC3(C(=O)CC2(C3(C)CO)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3309440
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1951.0	nM	PMID[501105]

☑ 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 NPC471941 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	168
0.1-0.2	1313
0.2-0.3	6482
0.3-0.4	15411
0.4-0.5	7349
0.5-0.6	6903
0.6-0.7	4346
0.7-0.8	703
0.8-0.85	17
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8587	High Similarity	NPC49371
0.8495	Intermediate Similarity	NPC18509
0.8333	Intermediate Similarity	NPC310010
0.8333	Intermediate Similarity	NPC326627
0.8316	Intermediate Similarity	NPC144956
0.8261	Intermediate Similarity	NPC233118
0.8247	Intermediate Similarity	NPC191892
0.8152	Intermediate Similarity	NPC168027
0.8152	Intermediate Similarity	NPC185936
0.8132	Intermediate Similarity	NPC76879
0.8125	Intermediate Similarity	NPC474720
0.809	Intermediate Similarity	NPC36350
0.809	Intermediate Similarity	NPC474218
0.8068	Intermediate Similarity	NPC64600
0.8061	Intermediate Similarity	NPC311612
0.8061	Intermediate Similarity	NPC117185
0.8043	Intermediate Similarity	NPC171441
0.8041	Intermediate Similarity	NPC237190
0.8022	Intermediate Similarity	NPC328539
0.8	Intermediate Similarity	NPC192428
0.8	Intermediate Similarity	NPC20688
0.8	Intermediate Similarity	NPC327115
0.8	Intermediate Similarity	NPC476043
0.8	Intermediate Similarity	NPC165873
0.798	Intermediate Similarity	NPC137657
0.7978	Intermediate Similarity	NPC237712
0.7978	Intermediate Similarity	NPC144258
0.7978	Intermediate Similarity	NPC82902
0.7959	Intermediate Similarity	NPC87351
0.7938	Intermediate Similarity	NPC15390
0.7935	Intermediate Similarity	NPC474245
0.7935	Intermediate Similarity	NPC477943
0.7935	Intermediate Similarity	NPC275740
0.7935	Intermediate Similarity	NPC86319
0.7917	Intermediate Similarity	NPC470834
0.7912	Intermediate Similarity	NPC472497
0.7912	Intermediate Similarity	NPC472484
0.7912	Intermediate Similarity	NPC472482
0.7912	Intermediate Similarity	NPC472481
0.7907	Intermediate Similarity	NPC19443
0.79	Intermediate Similarity	NPC196528
0.7879	Intermediate Similarity	NPC111323
0.7865	Intermediate Similarity	NPC474748
0.7865	Intermediate Similarity	NPC476082
0.7865	Intermediate Similarity	NPC278648
0.7849	Intermediate Similarity	NPC126993
0.7843	Intermediate Similarity	NPC214644
0.7835	Intermediate Similarity	NPC191565
0.7826	Intermediate Similarity	NPC143767
0.7826	Intermediate Similarity	NPC131470
0.7826	Intermediate Similarity	NPC477710
0.7826	Intermediate Similarity	NPC193360
0.7822	Intermediate Similarity	NPC44063
0.7822	Intermediate Similarity	NPC185
0.7805	Intermediate Similarity	NPC475952
0.7802	Intermediate Similarity	NPC469994
0.7802	Intermediate Similarity	NPC472494
0.7802	Intermediate Similarity	NPC472491
0.7802	Intermediate Similarity	NPC51014
0.7778	Intermediate Similarity	NPC321187
0.7778	Intermediate Similarity	NPC470840
0.7778	Intermediate Similarity	NPC58841
0.7778	Intermediate Similarity	NPC477915
0.7778	Intermediate Similarity	NPC329043
0.7778	Intermediate Similarity	NPC161423
0.7778	Intermediate Similarity	NPC227064
0.7755	Intermediate Similarity	NPC83709
0.7753	Intermediate Similarity	NPC193347
0.7742	Intermediate Similarity	NPC472971
0.7742	Intermediate Similarity	NPC472970
0.7742	Intermediate Similarity	NPC119416
0.7742	Intermediate Similarity	NPC2983
0.7732	Intermediate Similarity	NPC190554
0.7727	Intermediate Similarity	NPC164999
0.7723	Intermediate Similarity	NPC257353
0.7717	Intermediate Similarity	NPC317590
0.7717	Intermediate Similarity	NPC90652
0.7717	Intermediate Similarity	NPC472495
0.7708	Intermediate Similarity	NPC259286
0.7708	Intermediate Similarity	NPC473170
0.7708	Intermediate Similarity	NPC472485
0.7708	Intermediate Similarity	NPC472932
0.77	Intermediate Similarity	NPC168575
0.77	Intermediate Similarity	NPC140723
0.7692	Intermediate Similarity	NPC43775
0.7692	Intermediate Similarity	NPC469948
0.7692	Intermediate Similarity	NPC202868
0.7684	Intermediate Similarity	NPC477520
0.7684	Intermediate Similarity	NPC12722
0.7684	Intermediate Similarity	NPC125180
0.7684	Intermediate Similarity	NPC470376
0.7684	Intermediate Similarity	NPC470375
0.7684	Intermediate Similarity	NPC69454
0.7684	Intermediate Similarity	NPC472930
0.767	Intermediate Similarity	NPC2766
0.7667	Intermediate Similarity	NPC118800
0.7667	Intermediate Similarity	NPC472498
0.766	Intermediate Similarity	NPC46758
0.766	Intermediate Similarity	NPC320026
0.766	Intermediate Similarity	NPC183283
0.766	Intermediate Similarity	NPC477711
0.766	Intermediate Similarity	NPC134321
0.766	Intermediate Similarity	NPC129913
0.766	Intermediate Similarity	NPC128672
0.7653	Intermediate Similarity	NPC147954
0.7647	Intermediate Similarity	NPC477916
0.7647	Intermediate Similarity	NPC43285
0.7647	Intermediate Similarity	NPC58370
0.7647	Intermediate Similarity	NPC83744
0.7634	Intermediate Similarity	NPC310752
0.7634	Intermediate Similarity	NPC292491
0.7634	Intermediate Similarity	NPC328313
0.7634	Intermediate Similarity	NPC474677
0.7634	Intermediate Similarity	NPC471722
0.7634	Intermediate Similarity	NPC470417
0.7634	Intermediate Similarity	NPC472483
0.7634	Intermediate Similarity	NPC53911
0.7629	Intermediate Similarity	NPC173272
0.7629	Intermediate Similarity	NPC96859
0.7629	Intermediate Similarity	NPC249954
0.7629	Intermediate Similarity	NPC305483
0.7629	Intermediate Similarity	NPC477853
0.7629	Intermediate Similarity	NPC328162
0.7624	Intermediate Similarity	NPC29705
0.7624	Intermediate Similarity	NPC204833
0.7624	Intermediate Similarity	NPC209502
0.7619	Intermediate Similarity	NPC280782
0.7614	Intermediate Similarity	NPC229204
0.7614	Intermediate Similarity	NPC215843
0.7609	Intermediate Similarity	NPC72133
0.7609	Intermediate Similarity	NPC94755
0.7604	Intermediate Similarity	NPC111015
0.7604	Intermediate Similarity	NPC196485
0.7604	Intermediate Similarity	NPC298919
0.7604	Intermediate Similarity	NPC209662
0.7604	Intermediate Similarity	NPC245972
0.76	Intermediate Similarity	NPC185530
0.76	Intermediate Similarity	NPC473424
0.7596	Intermediate Similarity	NPC235077
0.7586	Intermediate Similarity	NPC197659
0.7586	Intermediate Similarity	NPC276769
0.7582	Intermediate Similarity	NPC59453
0.7582	Intermediate Similarity	NPC472480
0.7582	Intermediate Similarity	NPC214043
0.7582	Intermediate Similarity	NPC146683
0.7582	Intermediate Similarity	NPC473246
0.7582	Intermediate Similarity	NPC470812
0.7582	Intermediate Similarity	NPC221758
0.7582	Intermediate Similarity	NPC85774
0.7579	Intermediate Similarity	NPC110657
0.7579	Intermediate Similarity	NPC154101
0.7579	Intermediate Similarity	NPC23434
0.7579	Intermediate Similarity	NPC86266
0.7579	Intermediate Similarity	NPC212301
0.7579	Intermediate Similarity	NPC63748
0.7576	Intermediate Similarity	NPC110149
0.7576	Intermediate Similarity	NPC112167
0.7576	Intermediate Similarity	NPC154072
0.7573	Intermediate Similarity	NPC469508
0.7573	Intermediate Similarity	NPC329417
0.7556	Intermediate Similarity	NPC151519
0.7556	Intermediate Similarity	NPC48362
0.7553	Intermediate Similarity	NPC97032
0.7553	Intermediate Similarity	NPC1015
0.7553	Intermediate Similarity	NPC32830
0.7553	Intermediate Similarity	NPC54689
0.7553	Intermediate Similarity	NPC475921
0.7553	Intermediate Similarity	NPC31985
0.7553	Intermediate Similarity	NPC474704
0.7551	Intermediate Similarity	NPC472689
0.7551	Intermediate Similarity	NPC477267
0.7551	Intermediate Similarity	NPC472690
0.7551	Intermediate Similarity	NPC477268
0.7549	Intermediate Similarity	NPC260268
0.7549	Intermediate Similarity	NPC476027
0.7549	Intermediate Similarity	NPC296945
0.7549	Intermediate Similarity	NPC319077
0.7549	Intermediate Similarity	NPC149047
0.7549	Intermediate Similarity	NPC50692
0.7549	Intermediate Similarity	NPC85829
0.7549	Intermediate Similarity	NPC97202
0.7549	Intermediate Similarity	NPC171137
0.7549	Intermediate Similarity	NPC150531
0.7549	Intermediate Similarity	NPC152695
0.7549	Intermediate Similarity	NPC202167
0.7549	Intermediate Similarity	NPC48733
0.7549	Intermediate Similarity	NPC214264
0.7549	Intermediate Similarity	NPC49958
0.7549	Intermediate Similarity	NPC302607
0.7547	Intermediate Similarity	NPC108721
0.7547	Intermediate Similarity	NPC73300
0.7528	Intermediate Similarity	NPC172013
0.7528	Intermediate Similarity	NPC233352
0.7528	Intermediate Similarity	NPC824
0.7528	Intermediate Similarity	NPC472478
0.7528	Intermediate Similarity	NPC138492
0.7527	Intermediate Similarity	NPC159046
0.7527	Intermediate Similarity	NPC472493
0.7527	Intermediate Similarity	NPC474684
0.7527	Intermediate Similarity	NPC233836

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 NPC471941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1834
0.2-0.3	4363
0.3-0.4	1932
0.4-0.5	450
0.5-0.6	161
0.6-0.7	153
0.7-0.8	99
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8495	Intermediate Similarity	NPD4755	Approved
0.8333	Intermediate Similarity	NPD4753	Phase 2
0.8316	Intermediate Similarity	NPD4700	Approved
0.8316	Intermediate Similarity	NPD4696	Approved
0.8316	Intermediate Similarity	NPD5286	Approved
0.8316	Intermediate Similarity	NPD5285	Approved
0.8144	Intermediate Similarity	NPD5224	Approved
0.8144	Intermediate Similarity	NPD5226	Approved
0.8144	Intermediate Similarity	NPD4633	Approved
0.8144	Intermediate Similarity	NPD5225	Approved
0.8144	Intermediate Similarity	NPD5211	Phase 2
0.8085	Intermediate Similarity	NPD5210	Approved
0.8085	Intermediate Similarity	NPD4629	Approved
0.8061	Intermediate Similarity	NPD5174	Approved
0.8061	Intermediate Similarity	NPD5175	Approved
0.8041	Intermediate Similarity	NPD5223	Approved
0.8	Intermediate Similarity	NPD4697	Phase 3
0.798	Intermediate Similarity	NPD5141	Approved
0.7978	Intermediate Similarity	NPD4197	Approved
0.7935	Intermediate Similarity	NPD5328	Approved
0.7921	Intermediate Similarity	NPD7320	Approved
0.79	Intermediate Similarity	NPD5739	Approved
0.79	Intermediate Similarity	NPD7128	Approved
0.79	Intermediate Similarity	NPD6675	Approved
0.79	Intermediate Similarity	NPD6402	Approved
0.79	Intermediate Similarity	NPD4768	Approved
0.79	Intermediate Similarity	NPD4767	Approved
0.7889	Intermediate Similarity	NPD5329	Approved
0.7879	Intermediate Similarity	NPD4754	Approved
0.7872	Intermediate Similarity	NPD4202	Approved
0.7843	Intermediate Similarity	NPD6373	Approved
0.7843	Intermediate Similarity	NPD6372	Approved
0.7822	Intermediate Similarity	NPD5701	Approved
0.7822	Intermediate Similarity	NPD5697	Approved
0.7812	Intermediate Similarity	NPD5221	Approved
0.7812	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5222	Approved
0.7802	Intermediate Similarity	NPD5280	Approved
0.7802	Intermediate Similarity	NPD5690	Phase 2
0.7802	Intermediate Similarity	NPD3618	Phase 1
0.7802	Intermediate Similarity	NPD4694	Approved
0.7778	Intermediate Similarity	NPD3133	Approved
0.7778	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD3666	Approved
0.7766	Intermediate Similarity	NPD6079	Approved
0.7753	Intermediate Similarity	NPD4221	Approved
0.7753	Intermediate Similarity	NPD4223	Phase 3
0.7745	Intermediate Similarity	NPD4730	Approved
0.7745	Intermediate Similarity	NPD6881	Approved
0.7745	Intermediate Similarity	NPD4729	Approved
0.7745	Intermediate Similarity	NPD6899	Approved
0.7745	Intermediate Similarity	NPD5128	Approved
0.7732	Intermediate Similarity	NPD5173	Approved
0.7732	Intermediate Similarity	NPD6083	Phase 2
0.7732	Intermediate Similarity	NPD6084	Phase 2
0.7708	Intermediate Similarity	NPD5695	Phase 3
0.7692	Intermediate Similarity	NPD6649	Approved
0.7692	Intermediate Similarity	NPD6650	Approved
0.767	Intermediate Similarity	NPD6014	Approved
0.767	Intermediate Similarity	NPD6013	Approved
0.767	Intermediate Similarity	NPD6012	Approved
0.7653	Intermediate Similarity	NPD5696	Approved
0.7609	Intermediate Similarity	NPD5279	Phase 3
0.7596	Intermediate Similarity	NPD7102	Approved
0.7596	Intermediate Similarity	NPD5247	Approved
0.7596	Intermediate Similarity	NPD7290	Approved
0.7596	Intermediate Similarity	NPD5250	Approved
0.7596	Intermediate Similarity	NPD4634	Approved
0.7596	Intermediate Similarity	NPD6883	Approved
0.7596	Intermediate Similarity	NPD5249	Phase 3
0.7596	Intermediate Similarity	NPD5248	Approved
0.7596	Intermediate Similarity	NPD5251	Approved
0.7582	Intermediate Similarity	NPD4786	Approved
0.7573	Intermediate Similarity	NPD6011	Approved
0.7556	Intermediate Similarity	NPD3667	Approved
0.7524	Intermediate Similarity	NPD8130	Phase 1
0.7524	Intermediate Similarity	NPD6617	Approved
0.7524	Intermediate Similarity	NPD5215	Approved
0.7524	Intermediate Similarity	NPD5217	Approved
0.7524	Intermediate Similarity	NPD5216	Approved
0.7524	Intermediate Similarity	NPD6869	Approved
0.7524	Intermediate Similarity	NPD6847	Approved
0.7473	Intermediate Similarity	NPD4788	Approved
0.7453	Intermediate Similarity	NPD8297	Approved
0.7453	Intermediate Similarity	NPD6882	Approved
0.7429	Intermediate Similarity	NPD5169	Approved
0.7429	Intermediate Similarity	NPD5135	Approved
0.7429	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4138	Approved
0.7419	Intermediate Similarity	NPD4689	Approved
0.7419	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5205	Approved
0.7419	Intermediate Similarity	NPD4690	Approved
0.7419	Intermediate Similarity	NPD4693	Phase 3
0.7419	Intermediate Similarity	NPD4688	Approved
0.7358	Intermediate Similarity	NPD5127	Approved
0.7358	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4139	Approved
0.7253	Intermediate Similarity	NPD4692	Approved
0.7248	Intermediate Similarity	NPD6274	Approved
0.7234	Intermediate Similarity	NPD6098	Approved
0.7222	Intermediate Similarity	NPD4632	Approved
0.7216	Intermediate Similarity	NPD5281	Approved
0.7216	Intermediate Similarity	NPD5284	Approved
0.7172	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5167	Approved
0.7143	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD5133	Approved
0.7111	Intermediate Similarity	NPD3617	Approved
0.708	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6015	Approved
0.708	Intermediate Similarity	NPD6016	Approved
0.7075	Intermediate Similarity	NPD5168	Approved
0.7071	Intermediate Similarity	NPD6001	Approved
0.7054	Intermediate Similarity	NPD7100	Approved
0.7054	Intermediate Similarity	NPD7101	Approved
0.7048	Intermediate Similarity	NPD6008	Approved
0.7033	Intermediate Similarity	NPD4195	Approved
0.7027	Intermediate Similarity	NPD6317	Approved
0.7027	Intermediate Similarity	NPD6009	Approved
0.7018	Intermediate Similarity	NPD5988	Approved
0.7018	Intermediate Similarity	NPD6370	Approved
0.701	Intermediate Similarity	NPD6673	Approved
0.701	Intermediate Similarity	NPD6904	Approved
0.701	Intermediate Similarity	NPD6080	Approved
0.6991	Remote Similarity	NPD6319	Approved
0.697	Remote Similarity	NPD6399	Phase 3
0.6964	Remote Similarity	NPD6313	Approved
0.6964	Remote Similarity	NPD6314	Approved
0.6964	Remote Similarity	NPD6335	Approved
0.6957	Remote Similarity	NPD5368	Approved
0.6957	Remote Similarity	NPD7525	Registered
0.6947	Remote Similarity	NPD1696	Phase 3
0.6947	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5207	Approved
0.6939	Remote Similarity	NPD4096	Approved
0.6939	Remote Similarity	NPD5692	Phase 3
0.693	Remote Similarity	NPD6909	Approved
0.693	Remote Similarity	NPD6908	Approved
0.6923	Remote Similarity	NPD5091	Approved
0.6907	Remote Similarity	NPD5737	Approved
0.6907	Remote Similarity	NPD6903	Approved
0.6907	Remote Similarity	NPD6672	Approved
0.6897	Remote Similarity	NPD7492	Approved
0.6889	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD7146	Approved
0.6875	Remote Similarity	NPD5330	Approved
0.6875	Remote Similarity	NPD6684	Approved
0.6875	Remote Similarity	NPD7521	Approved
0.6869	Remote Similarity	NPD5694	Approved
0.6869	Remote Similarity	NPD6050	Approved
0.6869	Remote Similarity	NPD5693	Phase 1
0.6842	Remote Similarity	NPD3668	Phase 3
0.6838	Remote Similarity	NPD6616	Approved
0.6818	Remote Similarity	NPD4243	Approved
0.6809	Remote Similarity	NPD6435	Approved
0.6783	Remote Similarity	NPD5983	Phase 2
0.678	Remote Similarity	NPD7078	Approved
0.678	Remote Similarity	NPD8293	Discontinued
0.6774	Remote Similarity	NPD4695	Discontinued
0.6737	Remote Similarity	NPD5362	Discontinued
0.6735	Remote Similarity	NPD4518	Approved
0.6735	Remote Similarity	NPD5208	Approved
0.6735	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5282	Discontinued
0.6723	Remote Similarity	NPD7736	Approved
0.6706	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4789	Approved
0.6702	Remote Similarity	NPD5369	Approved
0.6701	Remote Similarity	NPD4623	Approved
0.6701	Remote Similarity	NPD4519	Discontinued
0.67	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6637	Remote Similarity	NPD6868	Approved
0.6596	Remote Similarity	NPD4748	Discontinued
0.6593	Remote Similarity	NPD3703	Phase 2
0.6593	Remote Similarity	NPD7339	Approved
0.6593	Remote Similarity	NPD4190	Phase 3
0.6593	Remote Similarity	NPD6942	Approved
0.6593	Remote Similarity	NPD5275	Approved
0.6591	Remote Similarity	NPD3698	Phase 2
0.6583	Remote Similarity	NPD6033	Approved
0.6559	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6336	Discontinued
0.6535	Remote Similarity	NPD8034	Phase 2
0.6535	Remote Similarity	NPD8035	Phase 2
0.6531	Remote Similarity	NPD5786	Approved
0.6522	Remote Similarity	NPD6933	Approved
0.6517	Remote Similarity	NPD4747	Approved
0.6517	Remote Similarity	NPD4244	Approved
0.6517	Remote Similarity	NPD4245	Approved
0.6514	Remote Similarity	NPD6412	Phase 2
0.6505	Remote Similarity	NPD1698	Clinical (unspecified phase)

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