NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	266.474
LogP:	2.617
LogD:	2.526
LogS:	-2.996
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.786
Synthetic Accessibility Score:	3.081
Fsp3:	0.467
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:	-4.252
MDCK Permeability:	1.535921182949096e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.801
Plasma Protein Binding (PPB):	88.2320556640625%
Volume Distribution (VD):	1.287
Pgp-substrate:	14.152034759521484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.149
CYP1A2-substrate:	0.45
CYP2C19-inhibitor:	0.481
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.168
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.376
CYP2D6-substrate:	0.649
CYP3A4-inhibitor:	0.224
CYP3A4-substrate:	0.483

ADMET: Excretion

Clearance (CL):	6.616
Half-life (T1/2):	0.518

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.13
Carcinogencity:	0.111
Eye Corrosion:	0.007
Eye Irritation:	0.956
Respiratory Toxicity:	0.001

Download Data

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

Natural Product: NPC474211

Natural Product ID:	NPC474211
*Common Name:**	Arbisabol-9-En-7,11-Diol
IUPAC Name:	(E)-2-methyl-6-(4-methylphenyl)hept-3-ene-2,6-diol
Synonyms:
Standard InCHIKey:	SPZUMECVMNZCHK-BJMVGYQFSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-12-6-8-13(9-7-12)15(4,17)11-5-10-14(2,3)16/h5-10,16-17H,11H2,1-4H3/b10-5+
SMILES:	Cc1ccc(cc1)C(C/C=C/C(O)(C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463531
PubChem CID:	11379323
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] 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
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974618]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27536968]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[574251]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[574251]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[574251]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[574251]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[574251]

☑ 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 NPC474211 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	184
0.1-0.2	1408
0.2-0.3	3698
0.3-0.4	12889
0.4-0.5	13371
0.5-0.6	8227
0.6-0.7	2327
0.7-0.8	515
0.8-0.85	64
0.85-0.9	8
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC474354
0.975	High Similarity	NPC168855
0.9639	High Similarity	NPC1793
0.9375	High Similarity	NPC133050
0.9048	High Similarity	NPC93843
0.9012	High Similarity	NPC328178
0.881	High Similarity	NPC304538
0.875	High Similarity	NPC79917
0.8625	High Similarity	NPC189371
0.8605	High Similarity	NPC243166
0.8602	High Similarity	NPC72729
0.8588	High Similarity	NPC95429
0.8571	High Similarity	NPC87299
0.8571	High Similarity	NPC99394
0.8571	High Similarity	NPC103326
0.8571	High Similarity	NPC329319
0.8471	Intermediate Similarity	NPC172984
0.8452	Intermediate Similarity	NPC117180
0.8421	Intermediate Similarity	NPC19856
0.8387	Intermediate Similarity	NPC6597
0.8387	Intermediate Similarity	NPC79241
0.8333	Intermediate Similarity	NPC315794
0.8316	Intermediate Similarity	NPC154905
0.8316	Intermediate Similarity	NPC60373
0.8298	Intermediate Similarity	NPC299762
0.8298	Intermediate Similarity	NPC33675
0.828	Intermediate Similarity	NPC312132
0.828	Intermediate Similarity	NPC259512
0.8261	Intermediate Similarity	NPC316301
0.8261	Intermediate Similarity	NPC152415
0.8261	Intermediate Similarity	NPC27323
0.8247	Intermediate Similarity	NPC471133
0.8242	Intermediate Similarity	NPC304541
0.8242	Intermediate Similarity	NPC128645
0.8235	Intermediate Similarity	NPC242628
0.8222	Intermediate Similarity	NPC242240
0.8222	Intermediate Similarity	NPC123273
0.8222	Intermediate Similarity	NPC318325
0.8211	Intermediate Similarity	NPC469481
0.8211	Intermediate Similarity	NPC289117
0.8193	Intermediate Similarity	NPC66655
0.8163	Intermediate Similarity	NPC53740
0.8163	Intermediate Similarity	NPC310456
0.8152	Intermediate Similarity	NPC306884
0.8152	Intermediate Similarity	NPC162314
0.8152	Intermediate Similarity	NPC55903
0.8152	Intermediate Similarity	NPC94139
0.8152	Intermediate Similarity	NPC147284
0.8152	Intermediate Similarity	NPC3358
0.8152	Intermediate Similarity	NPC210497
0.8144	Intermediate Similarity	NPC475225
0.814	Intermediate Similarity	NPC106313
0.8132	Intermediate Similarity	NPC192
0.8125	Intermediate Similarity	NPC252105
0.8111	Intermediate Similarity	NPC113460
0.8111	Intermediate Similarity	NPC25493
0.8111	Intermediate Similarity	NPC27974
0.8105	Intermediate Similarity	NPC92730
0.8095	Intermediate Similarity	NPC224544
0.8081	Intermediate Similarity	NPC27252
0.8081	Intermediate Similarity	NPC472980
0.8081	Intermediate Similarity	NPC472979
0.8081	Intermediate Similarity	NPC66834
0.8065	Intermediate Similarity	NPC289769
0.8061	Intermediate Similarity	NPC47284
0.8043	Intermediate Similarity	NPC306074
0.8043	Intermediate Similarity	NPC231150
0.8043	Intermediate Similarity	NPC314690
0.8043	Intermediate Similarity	NPC155908
0.8041	Intermediate Similarity	NPC471228
0.8041	Intermediate Similarity	NPC235762
0.8022	Intermediate Similarity	NPC258219
0.8022	Intermediate Similarity	NPC177420
0.8022	Intermediate Similarity	NPC280347
0.8021	Intermediate Similarity	NPC174911
0.8	Intermediate Similarity	NPC407
0.8	Intermediate Similarity	NPC225464
0.8	Intermediate Similarity	NPC474073
0.8	Intermediate Similarity	NPC77492
0.8	Intermediate Similarity	NPC306295
0.8	Intermediate Similarity	NPC23167
0.8	Intermediate Similarity	NPC307235
0.7979	Intermediate Similarity	NPC222146
0.7979	Intermediate Similarity	NPC26244
0.7959	Intermediate Similarity	NPC472221
0.7959	Intermediate Similarity	NPC472222
0.7938	Intermediate Similarity	NPC25458
0.7938	Intermediate Similarity	NPC80800
0.7938	Intermediate Similarity	NPC477685
0.7938	Intermediate Similarity	NPC304873
0.7935	Intermediate Similarity	NPC55561
0.7917	Intermediate Similarity	NPC252821
0.7917	Intermediate Similarity	NPC217621
0.7917	Intermediate Similarity	NPC122005
0.7912	Intermediate Similarity	NPC199567
0.7895	Intermediate Similarity	NPC132271
0.7895	Intermediate Similarity	NPC292730
0.7895	Intermediate Similarity	NPC82664
0.7895	Intermediate Similarity	NPC216520
0.7895	Intermediate Similarity	NPC473388
0.7889	Intermediate Similarity	NPC155393
0.7889	Intermediate Similarity	NPC197783
0.7879	Intermediate Similarity	NPC243601
0.7872	Intermediate Similarity	NPC245187
0.7872	Intermediate Similarity	NPC151715
0.7872	Intermediate Similarity	NPC76938
0.7865	Intermediate Similarity	NPC99482
0.7857	Intermediate Similarity	NPC108497
0.7849	Intermediate Similarity	NPC270547
0.7849	Intermediate Similarity	NPC45040
0.7843	Intermediate Similarity	NPC475002
0.7843	Intermediate Similarity	NPC133308
0.7843	Intermediate Similarity	NPC474057
0.7843	Intermediate Similarity	NPC95126
0.7841	Intermediate Similarity	NPC477770
0.7835	Intermediate Similarity	NPC48730
0.7835	Intermediate Similarity	NPC225506
0.7835	Intermediate Similarity	NPC129373
0.7835	Intermediate Similarity	NPC248396
0.7831	Intermediate Similarity	NPC108218
0.7826	Intermediate Similarity	NPC70940
0.7826	Intermediate Similarity	NPC274455
0.7826	Intermediate Similarity	NPC86670
0.7822	Intermediate Similarity	NPC149455
0.7822	Intermediate Similarity	NPC64642
0.7822	Intermediate Similarity	NPC472982
0.7812	Intermediate Similarity	NPC475078
0.7812	Intermediate Similarity	NPC152097
0.7802	Intermediate Similarity	NPC184169
0.7789	Intermediate Similarity	NPC274678
0.7789	Intermediate Similarity	NPC32714
0.7789	Intermediate Similarity	NPC8392
0.7789	Intermediate Similarity	NPC144682
0.7778	Intermediate Similarity	NPC238696
0.7778	Intermediate Similarity	NPC248817
0.7778	Intermediate Similarity	NPC286904
0.7778	Intermediate Similarity	NPC150837
0.7778	Intermediate Similarity	NPC175313
0.7778	Intermediate Similarity	NPC272029
0.7778	Intermediate Similarity	NPC227458
0.7778	Intermediate Similarity	NPC218879
0.7778	Intermediate Similarity	NPC244513
0.7767	Intermediate Similarity	NPC111108
0.7766	Intermediate Similarity	NPC138117
0.7766	Intermediate Similarity	NPC325292
0.7766	Intermediate Similarity	NPC271440
0.7742	Intermediate Similarity	NPC300017
0.7732	Intermediate Similarity	NPC260775
0.7732	Intermediate Similarity	NPC128723
0.7727	Intermediate Similarity	NPC475199
0.7727	Intermediate Similarity	NPC283012
0.7723	Intermediate Similarity	NPC158253
0.7723	Intermediate Similarity	NPC204901
0.7723	Intermediate Similarity	NPC249811
0.7723	Intermediate Similarity	NPC232523
0.7717	Intermediate Similarity	NPC19680
0.7708	Intermediate Similarity	NPC253423
0.77	Intermediate Similarity	NPC37802
0.77	Intermediate Similarity	NPC105899
0.77	Intermediate Similarity	NPC117115
0.77	Intermediate Similarity	NPC138942
0.7692	Intermediate Similarity	NPC211237
0.7692	Intermediate Similarity	NPC228452
0.7692	Intermediate Similarity	NPC198747
0.7684	Intermediate Similarity	NPC128062
0.7677	Intermediate Similarity	NPC242342
0.7677	Intermediate Similarity	NPC146798
0.7677	Intermediate Similarity	NPC71002
0.7677	Intermediate Similarity	NPC106396
0.7677	Intermediate Similarity	NPC222522
0.7677	Intermediate Similarity	NPC249828
0.7677	Intermediate Similarity	NPC94351
0.7677	Intermediate Similarity	NPC85479
0.7677	Intermediate Similarity	NPC168303
0.7677	Intermediate Similarity	NPC53051
0.7677	Intermediate Similarity	NPC24404
0.7677	Intermediate Similarity	NPC168829
0.7677	Intermediate Similarity	NPC302219
0.7677	Intermediate Similarity	NPC313030
0.7677	Intermediate Similarity	NPC269212
0.7667	Intermediate Similarity	NPC124436
0.7667	Intermediate Similarity	NPC265146
0.766	Intermediate Similarity	NPC204210
0.7653	Intermediate Similarity	NPC294741
0.7653	Intermediate Similarity	NPC211885
0.7653	Intermediate Similarity	NPC70677
0.7653	Intermediate Similarity	NPC130756
0.7653	Intermediate Similarity	NPC166761
0.7653	Intermediate Similarity	NPC12931
0.7653	Intermediate Similarity	NPC10588
0.7647	Intermediate Similarity	NPC64586
0.7647	Intermediate Similarity	NPC174981
0.7647	Intermediate Similarity	NPC11554
0.7634	Intermediate Similarity	NPC98772
0.7634	Intermediate Similarity	NPC70436
0.7624	Intermediate Similarity	NPC477814
0.7624	Intermediate Similarity	NPC99836
0.7624	Intermediate Similarity	NPC21594
0.7624	Intermediate Similarity	NPC201662
0.7624	Intermediate Similarity	NPC12640

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 NPC474211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1016
0.2-0.3	1279
0.3-0.4	2988
0.4-0.5	2136
0.5-0.6	1117
0.6-0.7	350
0.7-0.8	65
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.837	Intermediate Similarity	NPD844	Approved
0.828	Intermediate Similarity	NPD288	Approved
0.8261	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD1616	Discontinued
0.8193	Intermediate Similarity	NPD9294	Approved
0.8152	Intermediate Similarity	NPD845	Approved
0.8105	Intermediate Similarity	NPD3020	Approved
0.8041	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1101	Approved
0.7979	Intermediate Similarity	NPD2859	Approved
0.7979	Intermediate Similarity	NPD2860	Approved
0.7872	Intermediate Similarity	NPD2933	Approved
0.7872	Intermediate Similarity	NPD2934	Approved
0.7835	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1090	Approved
0.7826	Intermediate Similarity	NPD1089	Approved
0.7826	Intermediate Similarity	NPD1086	Approved
0.7789	Intermediate Similarity	NPD1809	Phase 2
0.7755	Intermediate Similarity	NPD4818	Approved
0.7755	Intermediate Similarity	NPD4817	Approved
0.7717	Intermediate Similarity	NPD800	Approved
0.7684	Intermediate Similarity	NPD1693	Approved
0.7667	Intermediate Similarity	NPD111	Approved
0.766	Intermediate Similarity	NPD1088	Approved
0.7579	Intermediate Similarity	NPD1409	Phase 3
0.7576	Intermediate Similarity	NPD940	Approved
0.7576	Intermediate Similarity	NPD846	Approved
0.7573	Intermediate Similarity	NPD4750	Phase 3
0.7524	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD4658	Approved
0.75	Intermediate Similarity	NPD1087	Approved
0.75	Intermediate Similarity	NPD4229	Approved
0.75	Intermediate Similarity	NPD3682	Approved
0.75	Intermediate Similarity	NPD3680	Approved
0.75	Intermediate Similarity	NPD3681	Approved
0.75	Intermediate Similarity	NPD3683	Approved
0.75	Intermediate Similarity	NPD4231	Approved
0.75	Intermediate Similarity	NPD4656	Approved
0.7474	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1445	Approved
0.7451	Intermediate Similarity	NPD1444	Approved
0.7404	Intermediate Similarity	NPD3022	Approved
0.7404	Intermediate Similarity	NPD3021	Approved
0.7379	Intermediate Similarity	NPD2342	Discontinued
0.7374	Intermediate Similarity	NPD2066	Phase 3
0.7368	Intermediate Similarity	NPD1239	Approved
0.7315	Intermediate Similarity	NPD4198	Discontinued
0.7308	Intermediate Similarity	NPD4720	Approved
0.7308	Intermediate Similarity	NPD4717	Approved
0.7308	Intermediate Similarity	NPD4718	Approved
0.729	Intermediate Similarity	NPD2229	Approved
0.729	Intermediate Similarity	NPD2234	Approved
0.729	Intermediate Similarity	NPD2228	Approved
0.729	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9612	Approved
0.7273	Intermediate Similarity	NPD9611	Approved
0.7273	Intermediate Similarity	NPD9609	Approved
0.7273	Intermediate Similarity	NPD9495	Approved
0.7253	Intermediate Similarity	NPD9491	Approved
0.7238	Intermediate Similarity	NPD1792	Phase 2
0.7228	Intermediate Similarity	NPD854	Approved
0.7228	Intermediate Similarity	NPD855	Approved
0.7222	Intermediate Similarity	NPD9250	Approved
0.7222	Intermediate Similarity	NPD226	Approved
0.7222	Intermediate Similarity	NPD5951	Approved
0.7216	Intermediate Similarity	NPD3718	Approved
0.7216	Intermediate Similarity	NPD3719	Approved
0.7188	Intermediate Similarity	NPD530	Approved
0.7172	Intermediate Similarity	NPD1565	Approved
0.7172	Intermediate Similarity	NPD1566	Phase 3
0.7172	Intermediate Similarity	NPD1564	Approved
0.717	Intermediate Similarity	NPD4253	Approved
0.717	Intermediate Similarity	NPD4254	Approved
0.7143	Intermediate Similarity	NPD7725	Approved
0.7143	Intermediate Similarity	NPD4814	Discontinued
0.7113	Intermediate Similarity	NPD752	Approved
0.7103	Intermediate Similarity	NPD2499	Approved
0.7103	Intermediate Similarity	NPD2500	Approved
0.7097	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1237	Approved
0.7083	Intermediate Similarity	NPD9256	Approved
0.7083	Intermediate Similarity	NPD9258	Approved
0.7065	Intermediate Similarity	NPD3971	Phase 1
0.7053	Intermediate Similarity	NPD531	Approved
0.7041	Intermediate Similarity	NPD719	Approved
0.7041	Intermediate Similarity	NPD720	Approved
0.7041	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6671	Approved
0.6991	Remote Similarity	NPD4059	Approved
0.6981	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5347	Phase 2
0.6979	Remote Similarity	NPD5346	Phase 2
0.697	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3091	Approved
0.6964	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7741	Discontinued
0.6961	Remote Similarity	NPD3028	Approved
0.6961	Remote Similarity	NPD1242	Phase 1
0.6947	Remote Similarity	NPD9538	Approved
0.6947	Remote Similarity	NPD4793	Discontinued
0.6944	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD9716	Approved
0.6923	Remote Similarity	NPD314	Approved
0.6923	Remote Similarity	NPD10	Approved
0.6923	Remote Similarity	NPD9608	Approved
0.6923	Remote Similarity	NPD9610	Approved
0.6923	Remote Similarity	NPD309	Approved
0.6923	Remote Similarity	NPD311	Approved
0.6923	Remote Similarity	NPD310	Approved
0.6923	Remote Similarity	NPD315	Approved
0.6909	Remote Similarity	NPD1793	Approved
0.6909	Remote Similarity	NPD2629	Approved
0.6909	Remote Similarity	NPD1791	Approved
0.6903	Remote Similarity	NPD1710	Approved
0.69	Remote Similarity	NPD1989	Approved
0.6889	Remote Similarity	NPD225	Approved
0.6889	Remote Similarity	NPD227	Approved
0.6887	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD1563	Approved
0.6863	Remote Similarity	NPD9712	Approved
0.6842	Remote Similarity	NPD4626	Approved
0.6842	Remote Similarity	NPD2932	Approved
0.6842	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5125	Phase 3
0.6842	Remote Similarity	NPD3019	Approved
0.6842	Remote Similarity	NPD5126	Approved
0.6827	Remote Similarity	NPD1929	Approved
0.6827	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD1930	Approved
0.6827	Remote Similarity	NPD1415	Approved
0.6827	Remote Similarity	NPD6647	Phase 2
0.6827	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD9500	Approved
0.6822	Remote Similarity	NPD2684	Approved
0.6818	Remote Similarity	NPD9087	Approved
0.6818	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD9490	Approved
0.68	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6049	Phase 2
0.6796	Remote Similarity	NPD2558	Approved
0.6796	Remote Similarity	NPD2550	Approved
0.6796	Remote Similarity	NPD2555	Approved
0.6796	Remote Similarity	NPD2549	Approved
0.6796	Remote Similarity	NPD2552	Approved
0.6796	Remote Similarity	NPD2553	Approved
0.6789	Remote Similarity	NPD228	Approved
0.6768	Remote Similarity	NPD9251	Approved
0.6765	Remote Similarity	NPD9273	Approved
0.6765	Remote Similarity	NPD9710	Approved
0.6765	Remote Similarity	NPD9711	Approved
0.6762	Remote Similarity	NPD3048	Approved
0.6762	Remote Similarity	NPD3046	Approved
0.6762	Remote Similarity	NPD3047	Approved
0.6762	Remote Similarity	NPD5909	Discontinued
0.6759	Remote Similarity	NPD5237	Approved
0.6759	Remote Similarity	NPD5239	Approved
0.6759	Remote Similarity	NPD5236	Approved
0.6759	Remote Similarity	NPD5235	Approved
0.6759	Remote Similarity	NPD5240	Approved
0.6757	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD475	Phase 2
0.6757	Remote Similarity	NPD497	Approved
0.6754	Remote Similarity	NPD4105	Approved
0.6754	Remote Similarity	NPD4102	Approved
0.6752	Remote Similarity	NPD4749	Approved
0.6731	Remote Similarity	NPD4719	Phase 2
0.6731	Remote Similarity	NPD4188	Approved
0.6731	Remote Similarity	NPD4189	Approved
0.6731	Remote Similarity	NPD1932	Approved
0.6729	Remote Similarity	NPD9532	Phase 3
0.6729	Remote Similarity	NPD6406	Approved
0.6724	Remote Similarity	NPD3092	Approved
0.6724	Remote Similarity	NPD804	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD9088	Approved
0.6697	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD2201	Approved
0.6697	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD2667	Approved
0.6696	Remote Similarity	NPD7157	Approved
0.6696	Remote Similarity	NPD2286	Discontinued
0.6696	Remote Similarity	NPD3095	Discontinued
0.6696	Remote Similarity	NPD5305	Approved
0.6696	Remote Similarity	NPD5306	Approved
0.6696	Remote Similarity	NPD2668	Approved
0.6696	Remote Similarity	NPD1751	Approved
0.6667	Remote Similarity	NPD498	Approved
0.6667	Remote Similarity	NPD496	Approved
0.6667	Remote Similarity	NPD2230	Approved
0.6667	Remote Similarity	NPD9257	Approved
0.6667	Remote Similarity	NPD1875	Phase 1
0.6667	Remote Similarity	NPD1398	Phase 1
0.6667	Remote Similarity	NPD2232	Approved
0.6667	Remote Similarity	NPD495	Approved
0.6667	Remote Similarity	NPD9259	Approved
0.6667	Remote Similarity	NPD2233	Approved
0.6638	Remote Similarity	NPD4135	Approved
0.6638	Remote Similarity	NPD4106	Approved
0.6638	Remote Similarity	NPD4136	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