NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.18
Volume:	263.191
LogP:	2.676
LogD:	2.504
LogS:	-2.263
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	4.587
Fsp3:	0.733
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:	-4.392
MDCK Permeability:	1.2623231668840162e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.045

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.91
Plasma Protein Binding (PPB):	81.57656860351562%
Volume Distribution (VD):	1.126
Pgp-substrate:	15.201338768005371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.233
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.123
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.447

ADMET: Excretion

Clearance (CL):	9.007
Half-life (T1/2):	0.342

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.206
Skin Sensitization:	0.062
Carcinogencity:	0.968
Eye Corrosion:	0.007
Eye Irritation:	0.518
Respiratory Toxicity:	0.766

Download Data

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

Natural Product: NPC473893

Natural Product ID:	NPC473893
*Common Name:**	11,12-Dihydroxy-6,10-Eremophiladiene
IUPAC Name:	2-[(8S,8aS)-8,8a-dimethyl-4,6,7,8-tetrahydro-3H-naphthalen-2-yl]propane-1,2-diol
Synonyms:
Standard InCHIKey:	IHQKZXXEUOQSEW-NFCBODTESA-N
Standard InCHI:	InChI=1S/C15H24O2/c1-11-5-4-6-12-7-8-13(9-14(11,12)2)15(3,17)10-16/h6,9,11,16-17H,4-5,7-8,10H2,1-3H3/t11-,14+,15?/m0/s1
SMILES:	C[C@H]1CCC=C2CCC(=C[C@]12C)C(C)(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454526
PubChem CID:	11953545
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6460	Lemnalia laevis	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16378367]
NPO14420	Lemnalia africana	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18247571]
NPO14420	Lemnalia africana	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8098734]
NPO14420	Lemnalia africana	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6460	Lemnalia laevis	Species	Nephtheidae	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
ED50	2
Others	1

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.21	ug ml-1	PMID[493520]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.33	ug ml-1	PMID[493520]
NPT27	Others	Unspecified		Activity	=	10.0	ug ml-1	PMID[493521]

☑ 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 NPC473893 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	169
0.1-0.2	1493
0.2-0.3	7371
0.3-0.4	17100
0.4-0.5	9259
0.5-0.6	5518
0.6-0.7	1486
0.7-0.8	270
0.8-0.85	24
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8657	High Similarity	NPC267027
0.8551	High Similarity	NPC471560
0.8529	High Similarity	NPC114651
0.8429	Intermediate Similarity	NPC34834
0.8382	Intermediate Similarity	NPC326310
0.8382	Intermediate Similarity	NPC202017
0.8378	Intermediate Similarity	NPC167891
0.8378	Intermediate Similarity	NPC83351
0.8286	Intermediate Similarity	NPC474248
0.8261	Intermediate Similarity	NPC68703
0.8261	Intermediate Similarity	NPC69649
0.8261	Intermediate Similarity	NPC171225
0.8219	Intermediate Similarity	NPC313179
0.8219	Intermediate Similarity	NPC171148
0.8219	Intermediate Similarity	NPC69383
0.8209	Intermediate Similarity	NPC81615
0.8194	Intermediate Similarity	NPC130665
0.8194	Intermediate Similarity	NPC220939
0.8194	Intermediate Similarity	NPC265485
0.8182	Intermediate Similarity	NPC66020
0.8182	Intermediate Similarity	NPC471408
0.8169	Intermediate Similarity	NPC189745
0.8143	Intermediate Similarity	NPC96484
0.8108	Intermediate Similarity	NPC265588
0.8088	Intermediate Similarity	NPC323424
0.8088	Intermediate Similarity	NPC290367
0.8088	Intermediate Similarity	NPC107540
0.8088	Intermediate Similarity	NPC96793
0.8082	Intermediate Similarity	NPC476366
0.8082	Intermediate Similarity	NPC201048
0.8077	Intermediate Similarity	NPC474634
0.8056	Intermediate Similarity	NPC471271
0.8056	Intermediate Similarity	NPC23954
0.8056	Intermediate Similarity	NPC471268
0.8056	Intermediate Similarity	NPC242992
0.8056	Intermediate Similarity	NPC477792
0.8	Intermediate Similarity	NPC91594
0.8	Intermediate Similarity	NPC82337
0.7975	Intermediate Similarity	NPC83702
0.7973	Intermediate Similarity	NPC66566
0.7973	Intermediate Similarity	NPC477923
0.7973	Intermediate Similarity	NPC32832
0.7971	Intermediate Similarity	NPC287339
0.7941	Intermediate Similarity	NPC174956
0.7917	Intermediate Similarity	NPC92801
0.791	Intermediate Similarity	NPC240506
0.7895	Intermediate Similarity	NPC476314
0.7887	Intermediate Similarity	NPC208999
0.7887	Intermediate Similarity	NPC471238
0.7867	Intermediate Similarity	NPC253190
0.7867	Intermediate Similarity	NPC274079
0.7867	Intermediate Similarity	NPC470749
0.7867	Intermediate Similarity	NPC477925
0.7857	Intermediate Similarity	NPC311736
0.7857	Intermediate Similarity	NPC279434
0.7857	Intermediate Similarity	NPC476406
0.7857	Intermediate Similarity	NPC250977
0.7848	Intermediate Similarity	NPC317458
0.7846	Intermediate Similarity	NPC48891
0.7838	Intermediate Similarity	NPC306727
0.7821	Intermediate Similarity	NPC264245
0.7821	Intermediate Similarity	NPC470298
0.7808	Intermediate Similarity	NPC471272
0.7808	Intermediate Similarity	NPC242001
0.7808	Intermediate Similarity	NPC164022
0.7794	Intermediate Similarity	NPC68679
0.7794	Intermediate Similarity	NPC321867
0.7794	Intermediate Similarity	NPC475251
0.7794	Intermediate Similarity	NPC207007
0.7792	Intermediate Similarity	NPC233295
0.7792	Intermediate Similarity	NPC28862
0.7792	Intermediate Similarity	NPC109546
0.7792	Intermediate Similarity	NPC47982
0.7792	Intermediate Similarity	NPC328714
0.7792	Intermediate Similarity	NPC81306
0.7792	Intermediate Similarity	NPC84694
0.7792	Intermediate Similarity	NPC143182
0.7778	Intermediate Similarity	NPC281316
0.7763	Intermediate Similarity	NPC470758
0.7763	Intermediate Similarity	NPC74995
0.7763	Intermediate Similarity	NPC477924
0.7763	Intermediate Similarity	NPC470711
0.7761	Intermediate Similarity	NPC122239
0.775	Intermediate Similarity	NPC238485
0.775	Intermediate Similarity	NPC185568
0.7746	Intermediate Similarity	NPC136813
0.7746	Intermediate Similarity	NPC163290
0.7733	Intermediate Similarity	NPC133580
0.7722	Intermediate Similarity	NPC87489
0.7722	Intermediate Similarity	NPC49964
0.7714	Intermediate Similarity	NPC258595
0.7714	Intermediate Similarity	NPC163678
0.7714	Intermediate Similarity	NPC471200
0.7703	Intermediate Similarity	NPC471799
0.7692	Intermediate Similarity	NPC241290
0.7692	Intermediate Similarity	NPC164840
0.7692	Intermediate Similarity	NPC96362
0.7692	Intermediate Similarity	NPC474592
0.7692	Intermediate Similarity	NPC209944
0.7692	Intermediate Similarity	NPC234193
0.7683	Intermediate Similarity	NPC245004
0.7681	Intermediate Similarity	NPC473759
0.7681	Intermediate Similarity	NPC473508
0.7681	Intermediate Similarity	NPC83200
0.7681	Intermediate Similarity	NPC474155
0.7671	Intermediate Similarity	NPC145498
0.7662	Intermediate Similarity	NPC475994
0.7662	Intermediate Similarity	NPC474216
0.7647	Intermediate Similarity	NPC135648
0.7647	Intermediate Similarity	NPC99487
0.7639	Intermediate Similarity	NPC117804
0.7639	Intermediate Similarity	NPC276616
0.7639	Intermediate Similarity	NPC216460
0.7632	Intermediate Similarity	NPC470525
0.7632	Intermediate Similarity	NPC263582
0.7632	Intermediate Similarity	NPC244488
0.7632	Intermediate Similarity	NPC247325
0.7632	Intermediate Similarity	NPC315261
0.7625	Intermediate Similarity	NPC475789
0.7625	Intermediate Similarity	NPC470384
0.7612	Intermediate Similarity	NPC155025
0.7606	Intermediate Similarity	NPC222366
0.7606	Intermediate Similarity	NPC286669
0.7606	Intermediate Similarity	NPC476039
0.76	Intermediate Similarity	NPC215050
0.76	Intermediate Similarity	NPC309178
0.76	Intermediate Similarity	NPC477138
0.76	Intermediate Similarity	NPC243342
0.76	Intermediate Similarity	NPC471797
0.7595	Intermediate Similarity	NPC249423
0.7595	Intermediate Similarity	NPC471270
0.7595	Intermediate Similarity	NPC476646
0.7595	Intermediate Similarity	NPC6663
0.7595	Intermediate Similarity	NPC209620
0.7595	Intermediate Similarity	NPC23852
0.7595	Intermediate Similarity	NPC47761
0.759	Intermediate Similarity	NPC474668
0.7571	Intermediate Similarity	NPC300593
0.7568	Intermediate Similarity	NPC167706
0.7564	Intermediate Similarity	NPC308038
0.7564	Intermediate Similarity	NPC19900
0.7564	Intermediate Similarity	NPC30986
0.7564	Intermediate Similarity	NPC152061
0.7564	Intermediate Similarity	NPC209430
0.7561	Intermediate Similarity	NPC472974
0.7561	Intermediate Similarity	NPC255143
0.7534	Intermediate Similarity	NPC9942
0.7532	Intermediate Similarity	NPC130136
0.7532	Intermediate Similarity	NPC325946
0.7532	Intermediate Similarity	NPC318495
0.7532	Intermediate Similarity	NPC198968
0.7532	Intermediate Similarity	NPC283619
0.7532	Intermediate Similarity	NPC155986
0.7531	Intermediate Similarity	NPC231310
0.7531	Intermediate Similarity	NPC205845
0.75	Intermediate Similarity	NPC475931
0.75	Intermediate Similarity	NPC202389
0.75	Intermediate Similarity	NPC115607
0.75	Intermediate Similarity	NPC477791
0.75	Intermediate Similarity	NPC189972
0.75	Intermediate Similarity	NPC291503
0.75	Intermediate Similarity	NPC470361
0.75	Intermediate Similarity	NPC38796
0.75	Intermediate Similarity	NPC197805
0.75	Intermediate Similarity	NPC49783
0.75	Intermediate Similarity	NPC114236
0.75	Intermediate Similarity	NPC158411
0.75	Intermediate Similarity	NPC50964
0.75	Intermediate Similarity	NPC20946
0.75	Intermediate Similarity	NPC101462
0.7468	Intermediate Similarity	NPC104120
0.7468	Intermediate Similarity	NPC148685
0.7468	Intermediate Similarity	NPC206062
0.7468	Intermediate Similarity	NPC471266
0.7468	Intermediate Similarity	NPC287749
0.7468	Intermediate Similarity	NPC236707
0.7468	Intermediate Similarity	NPC295131
0.7468	Intermediate Similarity	NPC113024
0.7468	Intermediate Similarity	NPC95124
0.7468	Intermediate Similarity	NPC157895
0.7467	Intermediate Similarity	NPC474140
0.7467	Intermediate Similarity	NPC186042
0.7467	Intermediate Similarity	NPC259049
0.7467	Intermediate Similarity	NPC474743
0.7463	Intermediate Similarity	NPC11130
0.7442	Intermediate Similarity	NPC310013
0.7439	Intermediate Similarity	NPC274448
0.7436	Intermediate Similarity	NPC275910
0.7436	Intermediate Similarity	NPC475980
0.7436	Intermediate Similarity	NPC62336
0.7436	Intermediate Similarity	NPC473943
0.7424	Intermediate Similarity	NPC227135
0.7424	Intermediate Similarity	NPC148163
0.7424	Intermediate Similarity	NPC148216
0.7424	Intermediate Similarity	NPC130209
0.7412	Intermediate Similarity	NPC80561
0.7412	Intermediate Similarity	NPC3345
0.7412	Intermediate Similarity	NPC11216
0.7412	Intermediate Similarity	NPC204188
0.7412	Intermediate Similarity	NPC291484

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 NPC473893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	2144
0.2-0.3	3962
0.3-0.4	2075
0.4-0.5	591
0.5-0.6	161
0.6-0.7	55
0.7-0.8	4
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8219	Intermediate Similarity	NPD8264	Approved
0.7794	Intermediate Similarity	NPD368	Approved
0.7632	Intermediate Similarity	NPD6933	Approved
0.7436	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD342	Phase 1
0.7403	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6926	Approved
0.7368	Intermediate Similarity	NPD6924	Approved
0.7273	Intermediate Similarity	NPD7339	Approved
0.7273	Intermediate Similarity	NPD6942	Approved
0.7262	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6930	Phase 2
0.725	Intermediate Similarity	NPD6931	Approved
0.725	Intermediate Similarity	NPD7514	Phase 3
0.725	Intermediate Similarity	NPD7332	Phase 2
0.7125	Intermediate Similarity	NPD6929	Approved
0.7089	Intermediate Similarity	NPD5776	Phase 2
0.7089	Intermediate Similarity	NPD6925	Approved
0.7067	Intermediate Similarity	NPD6922	Approved
0.7067	Intermediate Similarity	NPD6923	Approved
0.7059	Intermediate Similarity	NPD4219	Approved
0.7059	Intermediate Similarity	NPD7524	Approved
0.7	Intermediate Similarity	NPD7145	Approved
0.6988	Remote Similarity	NPD6695	Phase 3
0.6974	Remote Similarity	NPD7144	Approved
0.6974	Remote Similarity	NPD7143	Approved
0.6951	Remote Similarity	NPD6902	Approved
0.6951	Remote Similarity	NPD6898	Phase 1
0.6923	Remote Similarity	NPD4785	Approved
0.6923	Remote Similarity	NPD4784	Approved
0.6914	Remote Similarity	NPD7645	Phase 2
0.6905	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7152	Approved
0.6883	Remote Similarity	NPD7150	Approved
0.6883	Remote Similarity	NPD7151	Approved
0.6883	Remote Similarity	NPD4243	Approved
0.6875	Remote Similarity	NPD6932	Approved
0.6867	Remote Similarity	NPD3667	Approved
0.6829	Remote Similarity	NPD7509	Discontinued
0.6829	Remote Similarity	NPD4748	Discontinued
0.6829	Remote Similarity	NPD7525	Registered
0.6824	Remote Similarity	NPD1696	Phase 3
0.6824	Remote Similarity	NPD6893	Approved
0.6707	Remote Similarity	NPD6683	Phase 2
0.6706	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6625	Remote Similarity	NPD5275	Approved
0.6625	Remote Similarity	NPD4190	Phase 3
0.6582	Remote Similarity	NPD4732	Discontinued
0.6552	Remote Similarity	NPD4519	Discontinued
0.6552	Remote Similarity	NPD4623	Approved
0.6552	Remote Similarity	NPD5279	Phase 3
0.6512	Remote Similarity	NPD3666	Approved
0.6512	Remote Similarity	NPD3665	Phase 1
0.6512	Remote Similarity	NPD3133	Approved
0.6506	Remote Similarity	NPD4195	Approved
0.6489	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD4695	Discontinued
0.6374	Remote Similarity	NPD7087	Discontinued
0.6364	Remote Similarity	NPD3618	Phase 1
0.6333	Remote Similarity	NPD4753	Phase 2
0.6322	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5778	Approved
0.6304	Remote Similarity	NPD5779	Approved
0.6279	Remote Similarity	NPD4223	Phase 3
0.6279	Remote Similarity	NPD4221	Approved
0.6235	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4821	Approved
0.6235	Remote Similarity	NPD4819	Approved
0.6235	Remote Similarity	NPD4822	Approved
0.6235	Remote Similarity	NPD4820	Approved
0.6203	Remote Similarity	NPD791	Approved
0.6203	Remote Similarity	NPD15	Approved
0.6196	Remote Similarity	NPD6411	Approved
0.6196	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5280	Approved
0.618	Remote Similarity	NPD5690	Phase 2
0.618	Remote Similarity	NPD4694	Approved
0.6154	Remote Similarity	NPD5328	Approved
0.6145	Remote Similarity	NPD1346	Approved
0.6136	Remote Similarity	NPD3668	Phase 3
0.6136	Remote Similarity	NPD4197	Approved
0.6133	Remote Similarity	NPD4191	Approved
0.6133	Remote Similarity	NPD4193	Approved
0.6133	Remote Similarity	NPD4192	Approved
0.6133	Remote Similarity	NPD4194	Approved
0.6129	Remote Similarity	NPD4202	Approved
0.6087	Remote Similarity	NPD7136	Phase 2
0.6067	Remote Similarity	NPD5329	Approved
0.6061	Remote Similarity	NPD4265	Approved
0.6044	Remote Similarity	NPD4518	Approved
0.6026	Remote Similarity	NPD7331	Phase 2
0.6023	Remote Similarity	NPD5362	Discontinued
0.6023	Remote Similarity	NPD5331	Approved
0.6023	Remote Similarity	NPD5332	Approved
0.6022	Remote Similarity	NPD6079	Approved
0.6022	Remote Similarity	NPD7515	Phase 2
0.602	Remote Similarity	NPD4159	Approved
0.6	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD4268	Approved
0.6	Remote Similarity	NPD4138	Approved
0.6	Remote Similarity	NPD4688	Approved
0.6	Remote Similarity	NPD4629	Approved
0.6	Remote Similarity	NPD5205	Approved
0.6	Remote Similarity	NPD4693	Phase 3
0.6	Remote Similarity	NPD4690	Approved
0.6	Remote Similarity	NPD4271	Approved
0.6	Remote Similarity	NPD4689	Approved
0.5978	Remote Similarity	NPD6051	Approved
0.5978	Remote Similarity	NPD6101	Approved
0.5978	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4692	Approved
0.5977	Remote Similarity	NPD4139	Approved
0.5977	Remote Similarity	NPD4790	Discontinued
0.596	Remote Similarity	NPD5211	Phase 2
0.5957	Remote Similarity	NPD6399	Phase 3
0.5941	Remote Similarity	NPD6640	Phase 3
0.5918	Remote Similarity	NPD7640	Approved
0.5918	Remote Similarity	NPD7639	Approved
0.5914	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4096	Approved
0.5909	Remote Similarity	NPD4269	Approved
0.5909	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4270	Approved
0.5876	Remote Similarity	NPD4755	Approved
0.5876	Remote Similarity	NPD6083	Phase 2
0.5876	Remote Similarity	NPD6084	Phase 2
0.587	Remote Similarity	NPD4723	Approved
0.587	Remote Similarity	NPD4722	Approved
0.5862	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5344	Discontinued
0.5851	Remote Similarity	NPD5284	Approved
0.5851	Remote Similarity	NPD5281	Approved
0.5843	Remote Similarity	NPD6110	Phase 1
0.5843	Remote Similarity	NPD4788	Approved
0.5843	Remote Similarity	NPD7154	Phase 3
0.5842	Remote Similarity	NPD5141	Approved
0.5833	Remote Similarity	NPD7115	Discovery
0.5833	Remote Similarity	NPD8039	Approved
0.5824	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7638	Approved
0.5814	Remote Similarity	NPD3617	Approved
0.5806	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD1082	Approved
0.5773	Remote Similarity	NPD4697	Phase 3
0.5773	Remote Similarity	NPD5221	Approved
0.5773	Remote Similarity	NPD5222	Approved
0.5773	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5285	Approved
0.5758	Remote Similarity	NPD4700	Approved
0.5758	Remote Similarity	NPD5286	Approved
0.5758	Remote Similarity	NPD4696	Approved
0.5745	Remote Similarity	NPD5785	Approved
0.5745	Remote Similarity	NPD6698	Approved
0.5745	Remote Similarity	NPD46	Approved
0.5729	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD5363	Approved
0.5714	Remote Similarity	NPD5173	Approved
0.57	Remote Similarity	NPD5223	Approved
0.5696	Remote Similarity	NPD7341	Phase 2
0.5696	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD7983	Approved
0.5682	Remote Similarity	NPD4252	Approved
0.5673	Remote Similarity	NPD6686	Approved
0.5663	Remote Similarity	NPD5276	Approved
0.5657	Remote Similarity	NPD5290	Discontinued
0.5657	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD5696	Approved
0.5652	Remote Similarity	NPD7146	Approved
0.5652	Remote Similarity	NPD6409	Approved
0.5652	Remote Similarity	NPD6684	Approved
0.5652	Remote Similarity	NPD5786	Approved
0.5652	Remote Similarity	NPD5330	Approved
0.5652	Remote Similarity	NPD7521	Approved
0.5652	Remote Similarity	NPD7334	Approved
0.5644	Remote Similarity	NPD5225	Approved
0.5644	Remote Similarity	NPD5224	Approved
0.5644	Remote Similarity	NPD5226	Approved
0.5644	Remote Similarity	NPD4633	Approved
0.5625	Remote Similarity	NPD5133	Approved
0.5618	Remote Similarity	NPD5369	Approved
0.5612	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.561	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.561	Remote Similarity	NPD4137	Phase 3
0.56	Remote Similarity	NPD6404	Discontinued

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