NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.13
Volume:	249.361
LogP:	4.124
LogD:	3.504
LogS:	-4.109
# Rotatable Bonds:	0
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.742
Synthetic Accessibility Score:	3.732
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.802
MDCK Permeability:	1.3439073882182129e-05
Pgp-inhibitor:	0.072
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.35
Plasma Protein Binding (PPB):	94.8245849609375%
Volume Distribution (VD):	2.104
Pgp-substrate:	7.185661792755127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.294
CYP2C19-substrate:	0.716
CYP2C9-inhibitor:	0.284
CYP2C9-substrate:	0.762
CYP2D6-inhibitor:	0.227
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.271
CYP3A4-substrate:	0.49

ADMET: Excretion

Clearance (CL):	12.296
Half-life (T1/2):	0.278

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.455
Carcinogencity:	0.906
Eye Corrosion:	0.348
Eye Irritation:	0.905
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC158871

Natural Product ID:	NPC158871
*Common Name:**	1Alpha-Hydroxy-9-Deoxycacalol
IUPAC Name:	(5S,8S)-3,4,5-trimethyl-5,6,7,8-tetrahydrobenzo[f][1]benzofuran-8-ol
Synonyms:
Standard InCHIKey:	ZRWPAGVTPFFNTL-UFBFGSQYSA-N
Standard InCHI:	InChI=1S/C15H18O2/c1-8-4-5-12(16)11-6-13-15(9(2)7-17-13)10(3)14(8)11/h6-8,12,16H,4-5H2,1-3H3/t8-,12-/m0/s1
SMILES:	C[C@H]1CC[C@@H](c2cc3c(c(C)co3)c(C)c12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400521
PubChem CID:	23627125
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
NPO1183	Ligularia macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17672504]
NPO1183	Ligularia macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18044832]
NPO1183	Ligularia macrophylla	Species	Asteraceae	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
EC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	=	13.8	ug.mL-1	PMID[452829]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	15.2	ug.mL-1	PMID[452829]

☑ 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 NPC158871 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	357
0.1-0.2	1611
0.2-0.3	3455
0.3-0.4	9868
0.4-0.5	9210
0.5-0.6	3974
0.6-0.7	8899
0.7-0.8	5188
0.8-0.85	116
0.85-0.9	13
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9348	High Similarity	NPC233707
0.9197	High Similarity	NPC209858
0.9197	High Similarity	NPC324117
0.9116	High Similarity	NPC44606
0.8844	High Similarity	NPC95526
0.8816	High Similarity	NPC472299
0.8725	High Similarity	NPC13282
0.8699	High Similarity	NPC290038
0.8652	High Similarity	NPC265793
0.8571	High Similarity	NPC279596
0.8562	High Similarity	NPC329493
0.8543	High Similarity	NPC115869
0.8531	High Similarity	NPC278832
0.8531	High Similarity	NPC64157
0.8521	High Similarity	NPC274876
0.8472	Intermediate Similarity	NPC130976
0.8462	Intermediate Similarity	NPC269117
0.8452	Intermediate Similarity	NPC226287
0.8446	Intermediate Similarity	NPC471305
0.8442	Intermediate Similarity	NPC180924
0.8431	Intermediate Similarity	NPC179170
0.8431	Intermediate Similarity	NPC42458
0.8431	Intermediate Similarity	NPC290927
0.8431	Intermediate Similarity	NPC158261
0.8418	Intermediate Similarity	NPC136641
0.8417	Intermediate Similarity	NPC329707
0.8411	Intermediate Similarity	NPC472298
0.84	Intermediate Similarity	NPC150215
0.8387	Intermediate Similarity	NPC246647
0.8387	Intermediate Similarity	NPC299094
0.8387	Intermediate Similarity	NPC212967
0.8387	Intermediate Similarity	NPC164110
0.8387	Intermediate Similarity	NPC123153
0.8387	Intermediate Similarity	NPC10051
0.8387	Intermediate Similarity	NPC96342
0.8365	Intermediate Similarity	NPC255787
0.8345	Intermediate Similarity	NPC474737
0.8323	Intermediate Similarity	NPC221992
0.8322	Intermediate Similarity	NPC59459
0.8313	Intermediate Similarity	NPC472660
0.8311	Intermediate Similarity	NPC64568
0.8301	Intermediate Similarity	NPC145830
0.8298	Intermediate Similarity	NPC939
0.8288	Intermediate Similarity	NPC62735
0.8288	Intermediate Similarity	NPC202260
0.8286	Intermediate Similarity	NPC470841
0.8278	Intermediate Similarity	NPC478163
0.8261	Intermediate Similarity	NPC178382
0.8258	Intermediate Similarity	NPC148938
0.8258	Intermediate Similarity	NPC180901
0.8258	Intermediate Similarity	NPC300757
0.8252	Intermediate Similarity	NPC183103
0.8252	Intermediate Similarity	NPC312560
0.825	Intermediate Similarity	NPC191012
0.8247	Intermediate Similarity	NPC10429
0.8247	Intermediate Similarity	NPC131121
0.8247	Intermediate Similarity	NPC87708
0.8239	Intermediate Similarity	NPC245395
0.8239	Intermediate Similarity	NPC100849
0.8239	Intermediate Similarity	NPC308156
0.8239	Intermediate Similarity	NPC61788
0.8239	Intermediate Similarity	NPC470725
0.8235	Intermediate Similarity	NPC202595
0.8231	Intermediate Similarity	NPC112757
0.8228	Intermediate Similarity	NPC24761
0.8227	Intermediate Similarity	NPC59502
0.8217	Intermediate Similarity	NPC476350
0.8217	Intermediate Similarity	NPC476349
0.8217	Intermediate Similarity	NPC186113
0.82	Intermediate Similarity	NPC471451
0.82	Intermediate Similarity	NPC469642
0.8194	Intermediate Similarity	NPC84721
0.8194	Intermediate Similarity	NPC474000
0.8194	Intermediate Similarity	NPC135522
0.8194	Intermediate Similarity	NPC235333
0.8194	Intermediate Similarity	NPC263817
0.8187	Intermediate Similarity	NPC41689
0.8182	Intermediate Similarity	NPC149085
0.8182	Intermediate Similarity	NPC232645
0.8182	Intermediate Similarity	NPC72958
0.8182	Intermediate Similarity	NPC106372
0.8182	Intermediate Similarity	NPC58668
0.8182	Intermediate Similarity	NPC75377
0.8165	Intermediate Similarity	NPC470810
0.8158	Intermediate Similarity	NPC252208
0.8158	Intermediate Similarity	NPC61284
0.8158	Intermediate Similarity	NPC113428
0.8158	Intermediate Similarity	NPC478018
0.8158	Intermediate Similarity	NPC71055
0.8153	Intermediate Similarity	NPC294300
0.8153	Intermediate Similarity	NPC476404
0.8153	Intermediate Similarity	NPC44199
0.8153	Intermediate Similarity	NPC317900
0.8151	Intermediate Similarity	NPC471670
0.8151	Intermediate Similarity	NPC163029
0.8146	Intermediate Similarity	NPC97904
0.8143	Intermediate Similarity	NPC470858
0.8141	Intermediate Similarity	NPC478161
0.8141	Intermediate Similarity	NPC297531
0.8141	Intermediate Similarity	NPC213936
0.8141	Intermediate Similarity	NPC478159
0.8137	Intermediate Similarity	NPC291742
0.8133	Intermediate Similarity	NPC117674
0.8133	Intermediate Similarity	NPC3732
0.8129	Intermediate Similarity	NPC253872
0.8129	Intermediate Similarity	NPC207624
0.8129	Intermediate Similarity	NPC60211
0.8121	Intermediate Similarity	NPC263337
0.8117	Intermediate Similarity	NPC119929
0.8113	Intermediate Similarity	NPC472783
0.8113	Intermediate Similarity	NPC472780
0.8108	Intermediate Similarity	NPC470407
0.8101	Intermediate Similarity	NPC218818
0.8101	Intermediate Similarity	NPC477692
0.8101	Intermediate Similarity	NPC4950
0.8099	Intermediate Similarity	NPC50583
0.8095	Intermediate Similarity	NPC472376
0.8092	Intermediate Similarity	NPC281398
0.8092	Intermediate Similarity	NPC308799
0.8092	Intermediate Similarity	NPC39361
0.8089	Intermediate Similarity	NPC160015
0.8089	Intermediate Similarity	NPC247677
0.8079	Intermediate Similarity	NPC27798
0.8079	Intermediate Similarity	NPC469385
0.8079	Intermediate Similarity	NPC93241
0.8077	Intermediate Similarity	NPC88958
0.8077	Intermediate Similarity	NPC303950
0.8077	Intermediate Similarity	NPC475770
0.8077	Intermediate Similarity	NPC183874
0.8071	Intermediate Similarity	NPC68756
0.8071	Intermediate Similarity	NPC152525
0.8071	Intermediate Similarity	NPC111088
0.8069	Intermediate Similarity	NPC314048
0.8065	Intermediate Similarity	NPC149526
0.8065	Intermediate Similarity	NPC115324
0.8065	Intermediate Similarity	NPC474417
0.8065	Intermediate Similarity	NPC23668
0.8065	Intermediate Similarity	NPC170169
0.8065	Intermediate Similarity	NPC193976
0.8063	Intermediate Similarity	NPC473961
0.8056	Intermediate Similarity	NPC473982
0.8056	Intermediate Similarity	NPC239134
0.8056	Intermediate Similarity	NPC164295
0.8056	Intermediate Similarity	NPC41847
0.8054	Intermediate Similarity	NPC477537
0.8054	Intermediate Similarity	NPC473499
0.8054	Intermediate Similarity	NPC477535
0.8052	Intermediate Similarity	NPC158338
0.8052	Intermediate Similarity	NPC100985
0.8052	Intermediate Similarity	NPC288036
0.8052	Intermediate Similarity	NPC97029
0.8052	Intermediate Similarity	NPC97028
0.8052	Intermediate Similarity	NPC178202
0.8052	Intermediate Similarity	NPC65589
0.805	Intermediate Similarity	NPC472782
0.805	Intermediate Similarity	NPC472781
0.805	Intermediate Similarity	NPC47623
0.8041	Intermediate Similarity	NPC98395
0.8039	Intermediate Similarity	NPC93666
0.8039	Intermediate Similarity	NPC123202
0.8039	Intermediate Similarity	NPC7943
0.8039	Intermediate Similarity	NPC22005
0.8039	Intermediate Similarity	NPC17101
0.8039	Intermediate Similarity	NPC66991
0.8039	Intermediate Similarity	NPC77903
0.8038	Intermediate Similarity	NPC260902
0.8038	Intermediate Similarity	NPC217602
0.8038	Intermediate Similarity	NPC269495
0.8038	Intermediate Similarity	NPC158542
0.8038	Intermediate Similarity	NPC296957
0.8038	Intermediate Similarity	NPC104380
0.8038	Intermediate Similarity	NPC268360
0.8038	Intermediate Similarity	NPC473282
0.8027	Intermediate Similarity	NPC307401
0.8026	Intermediate Similarity	NPC478019
0.8026	Intermediate Similarity	NPC478166
0.8025	Intermediate Similarity	NPC53640
0.8025	Intermediate Similarity	NPC198490
0.8014	Intermediate Similarity	NPC476947
0.8013	Intermediate Similarity	NPC263676
0.8013	Intermediate Similarity	NPC273483
0.8013	Intermediate Similarity	NPC24232
0.8013	Intermediate Similarity	NPC142308
0.8013	Intermediate Similarity	NPC154683
0.8013	Intermediate Similarity	NPC5871
0.8013	Intermediate Similarity	NPC40356
0.8013	Intermediate Similarity	NPC84266
0.8012	Intermediate Similarity	NPC295914
0.8012	Intermediate Similarity	NPC472661
0.8	Intermediate Similarity	NPC218838
0.8	Intermediate Similarity	NPC78335
0.8	Intermediate Similarity	NPC30655
0.8	Intermediate Similarity	NPC118853
0.8	Intermediate Similarity	NPC230713
0.8	Intermediate Similarity	NPC45124
0.8	Intermediate Similarity	NPC141252
0.8	Intermediate Similarity	NPC74854
0.8	Intermediate Similarity	NPC167576
0.8	Intermediate Similarity	NPC11799
0.8	Intermediate Similarity	NPC165612

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 NPC158871 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	1008
0.2-0.3	1430
0.3-0.4	2581
0.4-0.5	1991
0.5-0.6	1148
0.6-0.7	531
0.7-0.8	118
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8542	High Similarity	NPD2343	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1283	Approved
0.8052	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD2346	Discontinued
0.8041	Intermediate Similarity	NPD2344	Approved
0.8029	Intermediate Similarity	NPD1651	Approved
0.7974	Intermediate Similarity	NPD6273	Approved
0.7911	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2799	Discontinued
0.7892	Intermediate Similarity	NPD6559	Discontinued
0.7881	Intermediate Similarity	NPD7003	Approved
0.7857	Intermediate Similarity	NPD1281	Approved
0.7829	Intermediate Similarity	NPD2309	Approved
0.7778	Intermediate Similarity	NPD6959	Discontinued
0.7755	Intermediate Similarity	NPD2979	Phase 3
0.7707	Intermediate Similarity	NPD3226	Approved
0.7682	Intermediate Similarity	NPD1471	Phase 3
0.7677	Intermediate Similarity	NPD2533	Approved
0.7677	Intermediate Similarity	NPD2534	Approved
0.7677	Intermediate Similarity	NPD2532	Approved
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.7616	Intermediate Similarity	NPD2935	Discontinued
0.7605	Intermediate Similarity	NPD5844	Phase 1
0.7589	Intermediate Similarity	NPD4626	Approved
0.7582	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD920	Approved
0.7569	Intermediate Similarity	NPD1876	Approved
0.7564	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5691	Approved
0.7517	Intermediate Similarity	NPD4060	Phase 1
0.7516	Intermediate Similarity	NPD7819	Suspended
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4477	Approved
0.75	Intermediate Similarity	NPD4476	Approved
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD2438	Suspended
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6355	Discontinued
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3972	Approved
0.7407	Intermediate Similarity	NPD5760	Phase 2
0.7407	Intermediate Similarity	NPD5761	Phase 2
0.74	Intermediate Similarity	NPD4140	Approved
0.7397	Intermediate Similarity	NPD2797	Approved
0.7394	Intermediate Similarity	NPD5494	Approved
0.7386	Intermediate Similarity	NPD2531	Phase 2
0.7383	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7473	Discontinued
0.7375	Intermediate Similarity	NPD7458	Discontinued
0.7362	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1611	Approved
0.7356	Intermediate Similarity	NPD8434	Phase 2
0.7355	Intermediate Similarity	NPD1243	Approved
0.7349	Intermediate Similarity	NPD1247	Approved
0.7347	Intermediate Similarity	NPD2798	Approved
0.7346	Intermediate Similarity	NPD37	Approved
0.7338	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1241	Discontinued
0.7333	Intermediate Similarity	NPD8032	Phase 2
0.7317	Intermediate Similarity	NPD4965	Approved
0.7317	Intermediate Similarity	NPD4966	Approved
0.7317	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD1608	Approved
0.7308	Intermediate Similarity	NPD3750	Approved
0.7305	Intermediate Similarity	NPD6232	Discontinued
0.7303	Intermediate Similarity	NPD1607	Approved
0.7297	Intermediate Similarity	NPD2861	Phase 2
0.729	Intermediate Similarity	NPD1549	Phase 2
0.729	Intermediate Similarity	NPD2424	Discontinued
0.729	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8312	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7273	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD2796	Approved
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD6099	Approved
0.7267	Intermediate Similarity	NPD3268	Approved
0.7267	Intermediate Similarity	NPD2649	Approved
0.7267	Intermediate Similarity	NPD2651	Approved
0.726	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2296	Approved
0.7244	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2800	Approved
0.7241	Intermediate Similarity	NPD1201	Approved
0.7239	Intermediate Similarity	NPD6280	Approved
0.7239	Intermediate Similarity	NPD6279	Approved
0.7239	Intermediate Similarity	NPD1934	Approved
0.7235	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD919	Approved
0.7226	Intermediate Similarity	NPD6004	Phase 3
0.7226	Intermediate Similarity	NPD6002	Phase 3
0.7226	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6005	Phase 3
0.7226	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4380	Phase 2
0.7212	Intermediate Similarity	NPD3882	Suspended
0.7211	Intermediate Similarity	NPD6696	Suspended
0.7208	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4308	Phase 3
0.7202	Intermediate Similarity	NPD7229	Phase 3
0.72	Intermediate Similarity	NPD4625	Phase 3
0.7181	Intermediate Similarity	NPD9494	Approved
0.7171	Intermediate Similarity	NPD1240	Approved
0.7162	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7135	Intermediate Similarity	NPD7177	Discontinued
0.7135	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD6844	Discontinued
0.7126	Intermediate Similarity	NPD6234	Discontinued
0.7124	Intermediate Similarity	NPD5735	Approved
0.7118	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5763	Approved
0.7115	Intermediate Similarity	NPD5762	Approved
0.7108	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7768	Phase 2
0.7108	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2932	Approved
0.7103	Intermediate Similarity	NPD1778	Approved
0.7103	Intermediate Similarity	NPD3019	Approved
0.7103	Intermediate Similarity	NPD17	Approved
0.7101	Intermediate Similarity	NPD5710	Approved
0.7101	Intermediate Similarity	NPD5711	Approved
0.7097	Intermediate Similarity	NPD3748	Approved
0.7097	Intermediate Similarity	NPD1510	Phase 2
0.7092	Intermediate Similarity	NPD1398	Phase 1
0.7091	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2801	Approved
0.7089	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4110	Phase 3
0.7083	Intermediate Similarity	NPD710	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7411	Suspended
0.7069	Intermediate Similarity	NPD6764	Approved
0.7069	Intermediate Similarity	NPD6765	Approved
0.7066	Intermediate Similarity	NPD7075	Discontinued
0.7063	Intermediate Similarity	NPD7390	Discontinued
0.7063	Intermediate Similarity	NPD1511	Approved
0.7063	Intermediate Similarity	NPD7340	Approved
0.7047	Intermediate Similarity	NPD1203	Approved
0.7041	Intermediate Similarity	NPD8127	Discontinued
0.7039	Intermediate Similarity	NPD7985	Registered
0.7039	Intermediate Similarity	NPD411	Approved
0.7037	Intermediate Similarity	NPD7427	Discontinued
0.7034	Intermediate Similarity	NPD5585	Approved
0.703	Intermediate Similarity	NPD6801	Discontinued
0.702	Intermediate Similarity	NPD6832	Phase 2
0.7019	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6166	Phase 2
0.7018	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD447	Suspended
0.7012	Intermediate Similarity	NPD6599	Discontinued
0.7	Intermediate Similarity	NPD6808	Phase 2
0.6993	Remote Similarity	NPD6663	Approved
0.6988	Remote Similarity	NPD1465	Phase 2
0.6975	Remote Similarity	NPD1512	Approved
0.6974	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6353	Approved
0.6968	Remote Similarity	NPD2157	Approved
0.6968	Remote Similarity	NPD4097	Suspended
0.6966	Remote Similarity	NPD1894	Discontinued
0.6964	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3926	Phase 2
0.6959	Remote Similarity	NPD1481	Phase 2
0.6959	Remote Similarity	NPD9717	Approved
0.6954	Remote Similarity	NPD5736	Approved
0.6948	Remote Similarity	NPD4307	Phase 2
0.6948	Remote Similarity	NPD3620	Phase 2
0.6948	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5402	Approved
0.6944	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5404	Approved
0.6943	Remote Similarity	NPD5405	Approved
0.6943	Remote Similarity	NPD5406	Approved
0.6943	Remote Similarity	NPD5408	Approved
0.6939	Remote Similarity	NPD3496	Discontinued
0.6936	Remote Similarity	NPD7228	Approved
0.6933	Remote Similarity	NPD3869	Phase 3
0.6933	Remote Similarity	NPD3873	Phase 3
0.6933	Remote Similarity	NPD3267	Approved
0.6933	Remote Similarity	NPD3266	Approved
0.6932	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6674	Discontinued
0.6914	Remote Similarity	NPD4662	Approved
0.6914	Remote Similarity	NPD4661	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