NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	254.634
LogP:	3.374
LogD:	3.563
LogS:	-4.762
# Rotatable Bonds:	0
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.652
Synthetic Accessibility Score:	6.143
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.531
MDCK Permeability:	1.3332212802197319e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.528
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.186
30% Bioavailability (F30%):	0.346

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.847
Plasma Protein Binding (PPB):	63.26675796508789%
Volume Distribution (VD):	2.109
Pgp-substrate:	21.943824768066406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.236
CYP1A2-substrate:	0.481
CYP2C19-inhibitor:	0.138
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.321
CYP3A4-substrate:	0.469

ADMET: Excretion

Clearance (CL):	15.128
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.809
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.778
Maximum Recommended Daily Dose:	0.516
Skin Sensitization:	0.241
Carcinogencity:	0.967
Eye Corrosion:	0.067
Eye Irritation:	0.549
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC152017

Natural Product ID:	NPC152017
*Common Name:**	Isocurcumenol
IUPAC Name:	n.a.
Synonyms:	Isocurcumenol
Standard InCHIKey:	DEBDFZGNZTYPMF-JURCDPSOSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h11-12,16H,3,5-8H2,1-2,4H3/t11-,12-,14-,15-/m0/s1
SMILES:	CC(=C1C[C@]23O[C@@]1(O)CC(=C)[C@@H]3CC[C@@H]2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2367911
PubChem CID:	12310886
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002874] Guaianes

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO17780	Curcuma heyneana	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23387824]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23738470]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[25275213]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO33283	zedoariae rhizoma	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9871681]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17780	Curcuma heyneana	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	5

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	<	65.0	%	PMID[540305]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9800.0	nM	PMID[540306]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	77.3	%	PMID[540304]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	80.2	%	PMID[540304]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	14.2	%	PMID[540304]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	36.5	%	PMID[540304]

☑ 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 NPC152017 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	147
0.1-0.2	1518
0.2-0.3	6326
0.3-0.4	17299
0.4-0.5	9363
0.5-0.6	6789
0.6-0.7	1193
0.7-0.8	50
0.8-0.85	3
0.85-0.9	3
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9306	High Similarity	NPC265921
0.9306	High Similarity	NPC215215
0.9306	High Similarity	NPC85831
0.8933	High Similarity	NPC470944
0.8333	Intermediate Similarity	NPC204270
0.8272	Intermediate Similarity	NPC116613
0.8228	Intermediate Similarity	NPC186072
0.8125	Intermediate Similarity	NPC15978
0.7791	Intermediate Similarity	NPC299527
0.7738	Intermediate Similarity	NPC287015
0.7738	Intermediate Similarity	NPC146850
0.7639	Intermediate Similarity	NPC63111
0.7619	Intermediate Similarity	NPC290052
0.7568	Intermediate Similarity	NPC261782
0.7568	Intermediate Similarity	NPC469326
0.7568	Intermediate Similarity	NPC205618
0.7558	Intermediate Similarity	NPC474832
0.75	Intermediate Similarity	NPC471184
0.7407	Intermediate Similarity	NPC476439
0.7403	Intermediate Similarity	NPC144647
0.7386	Intermediate Similarity	NPC205548
0.7349	Intermediate Similarity	NPC76054
0.7326	Intermediate Similarity	NPC119001
0.7326	Intermediate Similarity	NPC470658
0.7317	Intermediate Similarity	NPC4436
0.7294	Intermediate Similarity	NPC471340
0.7273	Intermediate Similarity	NPC475991
0.7262	Intermediate Similarity	NPC59994
0.7262	Intermediate Similarity	NPC78677
0.7229	Intermediate Similarity	NPC476701
0.7209	Intermediate Similarity	NPC474693
0.7195	Intermediate Similarity	NPC103987
0.7195	Intermediate Similarity	NPC53581
0.7179	Intermediate Similarity	NPC474900
0.7159	Intermediate Similarity	NPC191283
0.7143	Intermediate Similarity	NPC59442
0.7126	Intermediate Similarity	NPC471185
0.7126	Intermediate Similarity	NPC473659
0.7126	Intermediate Similarity	NPC475860
0.7126	Intermediate Similarity	NPC474694
0.7123	Intermediate Similarity	NPC52431
0.7123	Intermediate Similarity	NPC310228
0.7111	Intermediate Similarity	NPC37607
0.7111	Intermediate Similarity	NPC301969
0.7089	Intermediate Similarity	NPC471781
0.7073	Intermediate Similarity	NPC476317
0.7059	Intermediate Similarity	NPC471661
0.7051	Intermediate Similarity	NPC224532
0.7045	Intermediate Similarity	NPC67493
0.7045	Intermediate Similarity	NPC311163
0.7024	Intermediate Similarity	NPC17550
0.7011	Intermediate Similarity	NPC154893
0.7011	Intermediate Similarity	NPC37005
0.7011	Intermediate Similarity	NPC16887
0.7011	Intermediate Similarity	NPC53011
0.7	Intermediate Similarity	NPC104129
0.7	Intermediate Similarity	NPC249408
0.6989	Remote Similarity	NPC67584
0.6989	Remote Similarity	NPC52044
0.6989	Remote Similarity	NPC170120
0.6988	Remote Similarity	NPC471454
0.6979	Remote Similarity	NPC176406
0.6962	Remote Similarity	NPC304690
0.6962	Remote Similarity	NPC74722
0.6957	Remote Similarity	NPC272293
0.6957	Remote Similarity	NPC242419
0.6957	Remote Similarity	NPC32862
0.6957	Remote Similarity	NPC235126
0.6957	Remote Similarity	NPC40821
0.6947	Remote Similarity	NPC221615
0.6941	Remote Similarity	NPC190008
0.6923	Remote Similarity	NPC470817
0.6923	Remote Similarity	NPC136813
0.6915	Remote Similarity	NPC213078
0.6915	Remote Similarity	NPC98165
0.6905	Remote Similarity	NPC477089
0.6905	Remote Similarity	NPC63445
0.6905	Remote Similarity	NPC222210
0.6897	Remote Similarity	NPC477667
0.6897	Remote Similarity	NPC472473
0.6892	Remote Similarity	NPC469321
0.6889	Remote Similarity	NPC242448
0.6882	Remote Similarity	NPC472467
0.6882	Remote Similarity	NPC470013
0.6882	Remote Similarity	NPC470010
0.6882	Remote Similarity	NPC127019
0.6882	Remote Similarity	NPC323008
0.6882	Remote Similarity	NPC262133
0.6875	Remote Similarity	NPC254845
0.6867	Remote Similarity	NPC126969
0.6854	Remote Similarity	NPC477668
0.6849	Remote Similarity	NPC278550
0.6842	Remote Similarity	NPC161493
0.6842	Remote Similarity	NPC474480
0.6842	Remote Similarity	NPC476893
0.6829	Remote Similarity	NPC309178
0.6818	Remote Similarity	NPC156485
0.6813	Remote Similarity	NPC470819
0.6809	Remote Similarity	NPC213698
0.6809	Remote Similarity	NPC476894
0.6795	Remote Similarity	NPC230107
0.679	Remote Similarity	NPC471660
0.6786	Remote Similarity	NPC476703
0.6782	Remote Similarity	NPC472465
0.6774	Remote Similarity	NPC470187
0.6771	Remote Similarity	NPC476895
0.6747	Remote Similarity	NPC60818
0.6747	Remote Similarity	NPC113639
0.6747	Remote Similarity	NPC23231
0.6744	Remote Similarity	NPC80622
0.6744	Remote Similarity	NPC10636
0.6744	Remote Similarity	NPC206062
0.6742	Remote Similarity	NPC300082
0.6742	Remote Similarity	NPC147921
0.6742	Remote Similarity	NPC204105
0.6742	Remote Similarity	NPC284534
0.6742	Remote Similarity	NPC471494
0.6739	Remote Similarity	NPC197107
0.6739	Remote Similarity	NPC472466
0.6735	Remote Similarity	NPC300399
0.6735	Remote Similarity	NPC471889
0.6735	Remote Similarity	NPC471482
0.6711	Remote Similarity	NPC210346
0.6711	Remote Similarity	NPC15152
0.6709	Remote Similarity	NPC477791
0.6707	Remote Similarity	NPC14352
0.6707	Remote Similarity	NPC234527
0.6703	Remote Similarity	NPC471952
0.6703	Remote Similarity	NPC91248
0.6703	Remote Similarity	NPC79549
0.6702	Remote Similarity	NPC477131
0.6702	Remote Similarity	NPC474338
0.6702	Remote Similarity	NPC144202
0.6702	Remote Similarity	NPC198853
0.6667	Remote Similarity	NPC170148
0.6667	Remote Similarity	NPC256720
0.6667	Remote Similarity	NPC471888
0.6667	Remote Similarity	NPC249034
0.6667	Remote Similarity	NPC128133
0.6667	Remote Similarity	NPC471887
0.6667	Remote Similarity	NPC471450
0.6667	Remote Similarity	NPC246621
0.6667	Remote Similarity	NPC472471
0.6667	Remote Similarity	NPC472379
0.6667	Remote Similarity	NPC133698
0.6667	Remote Similarity	NPC236228
0.6667	Remote Similarity	NPC94127
0.6667	Remote Similarity	NPC131209
0.6667	Remote Similarity	NPC129630
0.6667	Remote Similarity	NPC471886
0.6667	Remote Similarity	NPC177818
0.6667	Remote Similarity	NPC5698
0.6667	Remote Similarity	NPC310643
0.6667	Remote Similarity	NPC470041
0.6667	Remote Similarity	NPC471885
0.6667	Remote Similarity	NPC472468
0.6667	Remote Similarity	NPC26307
0.6633	Remote Similarity	NPC150923
0.6633	Remote Similarity	NPC476896
0.6633	Remote Similarity	NPC474022
0.6632	Remote Similarity	NPC220221
0.6632	Remote Similarity	NPC469873
0.663	Remote Similarity	NPC215556
0.6628	Remote Similarity	NPC55304
0.6628	Remote Similarity	NPC86971
0.6628	Remote Similarity	NPC226226
0.6627	Remote Similarity	NPC471659
0.6627	Remote Similarity	NPC190859
0.6625	Remote Similarity	NPC470040
0.6625	Remote Similarity	NPC305698
0.6625	Remote Similarity	NPC167527
0.6623	Remote Similarity	NPC473508
0.66	Remote Similarity	NPC472819
0.6598	Remote Similarity	NPC64742
0.6598	Remote Similarity	NPC244411
0.6598	Remote Similarity	NPC470541
0.6598	Remote Similarity	NPC309493
0.6596	Remote Similarity	NPC135776
0.6596	Remote Similarity	NPC258216
0.6596	Remote Similarity	NPC27531
0.6593	Remote Similarity	NPC471657
0.6593	Remote Similarity	NPC45957
0.6591	Remote Similarity	NPC109938
0.6591	Remote Similarity	NPC122945
0.6588	Remote Similarity	NPC474826
0.6588	Remote Similarity	NPC477426
0.6588	Remote Similarity	NPC84360
0.6588	Remote Similarity	NPC477425
0.6588	Remote Similarity	NPC477427
0.6585	Remote Similarity	NPC469343
0.6582	Remote Similarity	NPC469328
0.6582	Remote Similarity	NPC311736
0.6582	Remote Similarity	NPC267027
0.6582	Remote Similarity	NPC162309
0.6579	Remote Similarity	NPC323153
0.6579	Remote Similarity	NPC135648
0.6579	Remote Similarity	NPC252809
0.6579	Remote Similarity	NPC66020
0.6566	Remote Similarity	NPC37207
0.6559	Remote Similarity	NPC295668

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 NPC152017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	1937
0.2-0.3	4306
0.3-0.4	2069
0.4-0.5	440
0.5-0.6	230
0.6-0.7	33
0.7-0.8	0
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
0.6818	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6695	Phase 3
0.6556	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6931	Approved
0.6552	Remote Similarity	NPD6930	Phase 2
0.6484	Remote Similarity	NPD4249	Approved
0.6437	Remote Similarity	NPD6929	Approved
0.6413	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4250	Approved
0.6413	Remote Similarity	NPD7750	Discontinued
0.6413	Remote Similarity	NPD4251	Approved
0.6413	Remote Similarity	NPD7524	Approved
0.6364	Remote Similarity	NPD7514	Phase 3
0.6333	Remote Similarity	NPD5362	Discontinued
0.6282	Remote Similarity	NPD368	Approved
0.6277	Remote Similarity	NPD1695	Approved
0.6235	Remote Similarity	NPD4784	Approved
0.6235	Remote Similarity	NPD6924	Approved
0.6235	Remote Similarity	NPD4785	Approved
0.6235	Remote Similarity	NPD6926	Approved
0.6207	Remote Similarity	NPD5776	Phase 2
0.6207	Remote Similarity	NPD6925	Approved
0.6196	Remote Similarity	NPD6893	Approved
0.619	Remote Similarity	NPD4243	Approved
0.618	Remote Similarity	NPD4822	Approved
0.618	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4819	Approved
0.618	Remote Similarity	NPD4820	Approved
0.618	Remote Similarity	NPD4821	Approved
0.618	Remote Similarity	NPD7332	Phase 2
0.6154	Remote Similarity	NPD5332	Approved
0.6154	Remote Similarity	NPD5331	Approved
0.6154	Remote Similarity	NPD1145	Discontinued
0.6146	Remote Similarity	NPD7087	Discontinued
0.6136	Remote Similarity	NPD7145	Approved
0.6111	Remote Similarity	NPD6902	Approved
0.6111	Remote Similarity	NPD4790	Discontinued
0.61	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD6933	Approved
0.6036	Remote Similarity	NPD7327	Approved
0.6036	Remote Similarity	NPD7328	Approved
0.6023	Remote Similarity	NPD6932	Approved
0.6019	Remote Similarity	NPD6053	Discontinued
0.6018	Remote Similarity	NPD8033	Approved
0.6	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7516	Approved
0.5979	Remote Similarity	NPD7637	Suspended
0.5977	Remote Similarity	NPD5275	Approved
0.5977	Remote Similarity	NPD4190	Phase 3
0.5955	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4271	Approved
0.5955	Remote Similarity	NPD4268	Approved
0.5938	Remote Similarity	NPD6051	Approved
0.5934	Remote Similarity	NPD6898	Phase 1
0.5929	Remote Similarity	NPD8377	Approved
0.5929	Remote Similarity	NPD8294	Approved
0.5926	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD342	Phase 1
0.5909	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD4195	Approved
0.5889	Remote Similarity	NPD6683	Phase 2
0.5882	Remote Similarity	NPD7640	Approved
0.5882	Remote Similarity	NPD7639	Approved
0.5877	Remote Similarity	NPD8296	Approved
0.5877	Remote Similarity	NPD8335	Approved
0.5877	Remote Similarity	NPD8380	Approved
0.5877	Remote Similarity	NPD8378	Approved
0.5877	Remote Similarity	NPD8379	Approved
0.5876	Remote Similarity	NPD6698	Approved
0.5876	Remote Similarity	NPD46	Approved
0.5859	Remote Similarity	NPD5282	Discontinued
0.5825	Remote Similarity	NPD5344	Discontinued
0.5824	Remote Similarity	NPD7509	Discontinued
0.5824	Remote Similarity	NPD7525	Registered
0.5795	Remote Similarity	NPD7339	Approved
0.5795	Remote Similarity	NPD6942	Approved
0.5784	Remote Similarity	NPD7638	Approved
0.5765	Remote Similarity	NPD6922	Approved
0.5765	Remote Similarity	NPD6923	Approved
0.5745	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD7503	Approved
0.5728	Remote Similarity	NPD6648	Approved
0.5714	Remote Similarity	NPD5785	Approved
0.5714	Remote Similarity	NPD3168	Discontinued
0.5714	Remote Similarity	NPD7838	Discovery
0.5699	Remote Similarity	NPD4270	Approved
0.5699	Remote Similarity	NPD4223	Phase 3
0.5699	Remote Similarity	NPD4269	Approved
0.5699	Remote Similarity	NPD4221	Approved
0.5698	Remote Similarity	NPD7144	Approved
0.5698	Remote Similarity	NPD7143	Approved
0.5688	Remote Similarity	NPD6371	Approved
0.5678	Remote Similarity	NPD7507	Approved
0.5663	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD5693	Phase 1
0.5652	Remote Similarity	NPD4748	Discontinued
0.5652	Remote Similarity	NPD6928	Phase 2
0.5648	Remote Similarity	NPD6686	Approved
0.5644	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD7154	Phase 3
0.5632	Remote Similarity	NPD7150	Approved
0.5632	Remote Similarity	NPD7152	Approved
0.5632	Remote Similarity	NPD7151	Approved
0.5631	Remote Similarity	NPD4225	Approved
0.5625	Remote Similarity	NPD5786	Approved
0.5604	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6399	Phase 3
0.56	Remote Similarity	NPD5778	Approved
0.56	Remote Similarity	NPD5779	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