NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.17
Volume:	257.684
LogP:	4.241
LogD:	3.759
LogS:	-4.109
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.759
Synthetic Accessibility Score:	2.717
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:	-4.389
MDCK Permeability:	1.5936240743030794e-05
Pgp-inhibitor:	0.713
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.728
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	94.49137878417969%
Volume Distribution (VD):	2.913
Pgp-substrate:	7.7602362632751465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.838
CYP1A2-substrate:	0.626
CYP2C19-inhibitor:	0.832
CYP2C19-substrate:	0.886
CYP2C9-inhibitor:	0.449
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.37
CYP2D6-substrate:	0.392
CYP3A4-inhibitor:	0.259
CYP3A4-substrate:	0.556

ADMET: Excretion

Clearance (CL):	13.028
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.311
Carcinogencity:	0.091
Eye Corrosion:	0.032
Eye Irritation:	0.953
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC474354

Natural Product ID:	NPC474354
*Common Name:**	Gossonorol
IUPAC Name:	6-methyl-2-(4-methylphenyl)hept-5-en-2-ol
Synonyms:	Gossonorol
Standard InCHIKey:	WQIRCLDVWQIBLO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H22O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-10,16H,5,11H2,1-4H3
SMILES:	CC1=CC=C(C=C1)C(C)(CCC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465590
PubChem CID:	185199
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[468313]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[468313]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[468313]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[468313]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[468313]

☑ 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 NPC474354 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	209
0.1-0.2	1552
0.2-0.3	3899
0.3-0.4	13638
0.4-0.5	13031
0.5-0.6	7837
0.6-0.7	2015
0.7-0.8	443
0.8-0.85	58
0.85-0.9	8
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC474211
0.9873	High Similarity	NPC168855
0.9518	High Similarity	NPC1793
0.9494	High Similarity	NPC133050
0.9157	High Similarity	NPC93843
0.8916	High Similarity	NPC304538
0.8889	High Similarity	NPC328178
0.8851	High Similarity	NPC79917
0.8734	High Similarity	NPC189371
0.8706	High Similarity	NPC243166
0.8675	High Similarity	NPC99394
0.8675	High Similarity	NPC329319
0.8675	High Similarity	NPC103326
0.8675	High Similarity	NPC87299
0.8571	High Similarity	NPC172984
0.8554	High Similarity	NPC117180
0.8495	Intermediate Similarity	NPC72729
0.8478	Intermediate Similarity	NPC6597
0.8478	Intermediate Similarity	NPC79241
0.8471	Intermediate Similarity	NPC95429
0.8387	Intermediate Similarity	NPC33675
0.8387	Intermediate Similarity	NPC299762
0.837	Intermediate Similarity	NPC312132
0.837	Intermediate Similarity	NPC259512
0.8352	Intermediate Similarity	NPC27323
0.8352	Intermediate Similarity	NPC316301
0.8352	Intermediate Similarity	NPC152415
0.8333	Intermediate Similarity	NPC304541
0.8333	Intermediate Similarity	NPC128645
0.8316	Intermediate Similarity	NPC19856
0.8315	Intermediate Similarity	NPC123273
0.8315	Intermediate Similarity	NPC242240
0.8315	Intermediate Similarity	NPC318325
0.8293	Intermediate Similarity	NPC66655
0.8242	Intermediate Similarity	NPC55903
0.8242	Intermediate Similarity	NPC94139
0.8242	Intermediate Similarity	NPC3358
0.8242	Intermediate Similarity	NPC210497
0.8242	Intermediate Similarity	NPC162314
0.8242	Intermediate Similarity	NPC306884
0.8242	Intermediate Similarity	NPC147284
0.8229	Intermediate Similarity	NPC315794
0.8222	Intermediate Similarity	NPC192
0.8211	Intermediate Similarity	NPC252105
0.8211	Intermediate Similarity	NPC154905
0.8211	Intermediate Similarity	NPC60373
0.8202	Intermediate Similarity	NPC27974
0.8202	Intermediate Similarity	NPC113460
0.8202	Intermediate Similarity	NPC25493
0.8193	Intermediate Similarity	NPC224544
0.8152	Intermediate Similarity	NPC289769
0.8144	Intermediate Similarity	NPC471133
0.8132	Intermediate Similarity	NPC314690
0.8132	Intermediate Similarity	NPC231150
0.8132	Intermediate Similarity	NPC306074
0.8132	Intermediate Similarity	NPC155908
0.8118	Intermediate Similarity	NPC242628
0.8111	Intermediate Similarity	NPC280347
0.8111	Intermediate Similarity	NPC258219
0.8111	Intermediate Similarity	NPC177420
0.8105	Intermediate Similarity	NPC469481
0.8105	Intermediate Similarity	NPC289117
0.809	Intermediate Similarity	NPC307235
0.809	Intermediate Similarity	NPC407
0.809	Intermediate Similarity	NPC23167
0.8085	Intermediate Similarity	NPC77492
0.8085	Intermediate Similarity	NPC225464
0.8065	Intermediate Similarity	NPC222146
0.8061	Intermediate Similarity	NPC53740
0.8061	Intermediate Similarity	NPC310456
0.8041	Intermediate Similarity	NPC475225
0.8023	Intermediate Similarity	NPC106313
0.8022	Intermediate Similarity	NPC55561
0.8	Intermediate Similarity	NPC122005
0.8	Intermediate Similarity	NPC252821
0.8	Intermediate Similarity	NPC199567
0.8	Intermediate Similarity	NPC92730
0.798	Intermediate Similarity	NPC472980
0.798	Intermediate Similarity	NPC66834
0.798	Intermediate Similarity	NPC27252
0.798	Intermediate Similarity	NPC472979
0.7978	Intermediate Similarity	NPC155393
0.7978	Intermediate Similarity	NPC197783
0.7959	Intermediate Similarity	NPC47284
0.7959	Intermediate Similarity	NPC243601
0.7957	Intermediate Similarity	NPC76938
0.7957	Intermediate Similarity	NPC245187
0.7938	Intermediate Similarity	NPC235762
0.7938	Intermediate Similarity	NPC471228
0.7927	Intermediate Similarity	NPC108218
0.7917	Intermediate Similarity	NPC225506
0.7917	Intermediate Similarity	NPC174911
0.79	Intermediate Similarity	NPC306295
0.7895	Intermediate Similarity	NPC474073
0.7889	Intermediate Similarity	NPC184169
0.7872	Intermediate Similarity	NPC144682
0.7872	Intermediate Similarity	NPC26244
0.7872	Intermediate Similarity	NPC8392
0.7872	Intermediate Similarity	NPC32714
0.7865	Intermediate Similarity	NPC150837
0.7865	Intermediate Similarity	NPC248817
0.7865	Intermediate Similarity	NPC286904
0.7865	Intermediate Similarity	NPC175313
0.7857	Intermediate Similarity	NPC472222
0.7857	Intermediate Similarity	NPC472221
0.7857	Intermediate Similarity	NPC238696
0.7849	Intermediate Similarity	NPC271440
0.7835	Intermediate Similarity	NPC25458
0.7835	Intermediate Similarity	NPC80800
0.7835	Intermediate Similarity	NPC477685
0.7835	Intermediate Similarity	NPC304873
0.7816	Intermediate Similarity	NPC475199
0.7816	Intermediate Similarity	NPC283012
0.7812	Intermediate Similarity	NPC217621
0.7802	Intermediate Similarity	NPC19680
0.7789	Intermediate Similarity	NPC82664
0.7789	Intermediate Similarity	NPC473388
0.7789	Intermediate Similarity	NPC216520
0.7789	Intermediate Similarity	NPC132271
0.7789	Intermediate Similarity	NPC292730
0.7778	Intermediate Similarity	NPC211237
0.7778	Intermediate Similarity	NPC198747
0.7778	Intermediate Similarity	NPC117115
0.7766	Intermediate Similarity	NPC151715
0.7755	Intermediate Similarity	NPC108497
0.7753	Intermediate Similarity	NPC124436
0.7753	Intermediate Similarity	NPC265146
0.7753	Intermediate Similarity	NPC99482
0.7745	Intermediate Similarity	NPC474057
0.7745	Intermediate Similarity	NPC133308
0.7745	Intermediate Similarity	NPC475002
0.7745	Intermediate Similarity	NPC95126
0.7742	Intermediate Similarity	NPC204210
0.7742	Intermediate Similarity	NPC45040
0.7742	Intermediate Similarity	NPC270547
0.7732	Intermediate Similarity	NPC211885
0.7732	Intermediate Similarity	NPC48730
0.7732	Intermediate Similarity	NPC248396
0.7732	Intermediate Similarity	NPC129373
0.7727	Intermediate Similarity	NPC477770
0.7723	Intermediate Similarity	NPC64642
0.7723	Intermediate Similarity	NPC472982
0.7723	Intermediate Similarity	NPC64586
0.7723	Intermediate Similarity	NPC149455
0.7717	Intermediate Similarity	NPC70940
0.7717	Intermediate Similarity	NPC98772
0.7717	Intermediate Similarity	NPC70436
0.7717	Intermediate Similarity	NPC274455
0.7717	Intermediate Similarity	NPC86670
0.7708	Intermediate Similarity	NPC152097
0.7708	Intermediate Similarity	NPC475078
0.77	Intermediate Similarity	NPC21594
0.7684	Intermediate Similarity	NPC274678
0.7684	Intermediate Similarity	NPC21959
0.7683	Intermediate Similarity	NPC208302
0.7677	Intermediate Similarity	NPC218879
0.7677	Intermediate Similarity	NPC244513
0.7677	Intermediate Similarity	NPC272029
0.7677	Intermediate Similarity	NPC227458
0.767	Intermediate Similarity	NPC111108
0.766	Intermediate Similarity	NPC325292
0.766	Intermediate Similarity	NPC138117
0.7653	Intermediate Similarity	NPC51015
0.7647	Intermediate Similarity	NPC58865
0.7634	Intermediate Similarity	NPC300017
0.7629	Intermediate Similarity	NPC260775
0.7629	Intermediate Similarity	NPC128723
0.7624	Intermediate Similarity	NPC158253
0.7624	Intermediate Similarity	NPC232523
0.7624	Intermediate Similarity	NPC249811
0.7624	Intermediate Similarity	NPC151477
0.7624	Intermediate Similarity	NPC204901
0.7604	Intermediate Similarity	NPC202986
0.7604	Intermediate Similarity	NPC253423
0.76	Intermediate Similarity	NPC37802
0.76	Intermediate Similarity	NPC105899
0.76	Intermediate Similarity	NPC138942
0.7596	Intermediate Similarity	NPC228452
0.7586	Intermediate Similarity	NPC164449
0.7586	Intermediate Similarity	NPC184030
0.7579	Intermediate Similarity	NPC128062
0.7576	Intermediate Similarity	NPC94351
0.7576	Intermediate Similarity	NPC24404
0.7576	Intermediate Similarity	NPC313030
0.7576	Intermediate Similarity	NPC168829
0.7576	Intermediate Similarity	NPC242342
0.7576	Intermediate Similarity	NPC53051
0.7576	Intermediate Similarity	NPC168303
0.7576	Intermediate Similarity	NPC106396
0.7576	Intermediate Similarity	NPC146798
0.7576	Intermediate Similarity	NPC302219
0.7576	Intermediate Similarity	NPC85479
0.7576	Intermediate Similarity	NPC249828
0.7576	Intermediate Similarity	NPC269212
0.7576	Intermediate Similarity	NPC71002
0.7576	Intermediate Similarity	NPC222522
0.7551	Intermediate Similarity	NPC294741
0.7551	Intermediate Similarity	NPC70677
0.7551	Intermediate Similarity	NPC10588
0.7551	Intermediate Similarity	NPC12931

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 NPC474354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	1042
0.2-0.3	1298
0.3-0.4	3065
0.4-0.5	2053
0.5-0.6	1076
0.6-0.7	324
0.7-0.8	59
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
0.8462	Intermediate Similarity	NPD844	Approved
0.837	Intermediate Similarity	NPD288	Approved
0.8352	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD1616	Discontinued
0.8293	Intermediate Similarity	NPD9294	Approved
0.8242	Intermediate Similarity	NPD845	Approved
0.8125	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3020	Approved
0.7889	Intermediate Similarity	NPD1101	Approved
0.7872	Intermediate Similarity	NPD1809	Phase 2
0.7872	Intermediate Similarity	NPD2859	Approved
0.7872	Intermediate Similarity	NPD2860	Approved
0.7835	Intermediate Similarity	NPD4818	Approved
0.7835	Intermediate Similarity	NPD4817	Approved
0.7766	Intermediate Similarity	NPD2934	Approved
0.7766	Intermediate Similarity	NPD2933	Approved
0.7753	Intermediate Similarity	NPD111	Approved
0.7732	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD1086	Approved
0.7717	Intermediate Similarity	NPD1090	Approved
0.7717	Intermediate Similarity	NPD1089	Approved
0.7609	Intermediate Similarity	NPD800	Approved
0.7579	Intermediate Similarity	NPD1693	Approved
0.7576	Intermediate Similarity	NPD4656	Approved
0.7576	Intermediate Similarity	NPD4658	Approved
0.7576	Intermediate Similarity	NPD4229	Approved
0.7576	Intermediate Similarity	NPD3680	Approved
0.7576	Intermediate Similarity	NPD3682	Approved
0.7576	Intermediate Similarity	NPD3681	Approved
0.7576	Intermediate Similarity	NPD3683	Approved
0.7576	Intermediate Similarity	NPD4231	Approved
0.7553	Intermediate Similarity	NPD1088	Approved
0.7525	Intermediate Similarity	NPD1445	Approved
0.7525	Intermediate Similarity	NPD1444	Approved
0.7476	Intermediate Similarity	NPD4750	Phase 3
0.7475	Intermediate Similarity	NPD846	Approved
0.7475	Intermediate Similarity	NPD940	Approved
0.7474	Intermediate Similarity	NPD1409	Phase 3
0.7451	Intermediate Similarity	NPD2342	Discontinued
0.7429	Intermediate Similarity	NPD7635	Approved
0.7391	Intermediate Similarity	NPD1087	Approved
0.7379	Intermediate Similarity	NPD4717	Approved
0.7379	Intermediate Similarity	NPD4720	Approved
0.7379	Intermediate Similarity	NPD4718	Approved
0.7368	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD9611	Approved
0.7347	Intermediate Similarity	NPD9609	Approved
0.7347	Intermediate Similarity	NPD9612	Approved
0.7308	Intermediate Similarity	NPD1792	Phase 2
0.7308	Intermediate Similarity	NPD3021	Approved
0.7308	Intermediate Similarity	NPD3022	Approved
0.73	Intermediate Similarity	NPD854	Approved
0.73	Intermediate Similarity	NPD855	Approved
0.7273	Intermediate Similarity	NPD2066	Phase 3
0.7263	Intermediate Similarity	NPD1239	Approved
0.7238	Intermediate Similarity	NPD4253	Approved
0.7238	Intermediate Similarity	NPD4254	Approved
0.7222	Intermediate Similarity	NPD4198	Discontinued
0.7196	Intermediate Similarity	NPD2234	Approved
0.7196	Intermediate Similarity	NPD2228	Approved
0.7196	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2229	Approved
0.7172	Intermediate Similarity	NPD9495	Approved
0.717	Intermediate Similarity	NPD2499	Approved
0.717	Intermediate Similarity	NPD2500	Approved
0.7157	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9491	Approved
0.713	Intermediate Similarity	NPD5951	Approved
0.7113	Intermediate Similarity	NPD3718	Approved
0.7113	Intermediate Similarity	NPD3719	Approved
0.7111	Intermediate Similarity	NPD9250	Approved
0.7111	Intermediate Similarity	NPD226	Approved
0.7083	Intermediate Similarity	NPD530	Approved
0.7071	Intermediate Similarity	NPD1565	Approved
0.7071	Intermediate Similarity	NPD1566	Phase 3
0.7071	Intermediate Similarity	NPD1564	Approved
0.7054	Intermediate Similarity	NPD7725	Approved
0.7041	Intermediate Similarity	NPD4814	Discontinued
0.7027	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD752	Approved
0.7	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.699	Remote Similarity	NPD310	Approved
0.699	Remote Similarity	NPD9608	Approved
0.699	Remote Similarity	NPD1237	Approved
0.699	Remote Similarity	NPD314	Approved
0.699	Remote Similarity	NPD10	Approved
0.699	Remote Similarity	NPD315	Approved
0.699	Remote Similarity	NPD9610	Approved
0.699	Remote Similarity	NPD311	Approved
0.699	Remote Similarity	NPD309	Approved
0.6989	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD9258	Approved
0.6979	Remote Similarity	NPD9256	Approved
0.6972	Remote Similarity	NPD1793	Approved
0.6972	Remote Similarity	NPD1791	Approved
0.6964	Remote Similarity	NPD1710	Approved
0.6957	Remote Similarity	NPD3971	Phase 1
0.6952	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD531	Approved
0.6939	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD720	Approved
0.6939	Remote Similarity	NPD719	Approved
0.6909	Remote Similarity	NPD6671	Approved
0.6903	Remote Similarity	NPD4059	Approved
0.6897	Remote Similarity	NPD9087	Approved
0.6893	Remote Similarity	NPD1415	Approved
0.6893	Remote Similarity	NPD9500	Approved
0.6887	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5346	Phase 2
0.6875	Remote Similarity	NPD7741	Discontinued
0.6875	Remote Similarity	NPD5347	Phase 2
0.6875	Remote Similarity	NPD3091	Approved
0.6869	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3028	Approved
0.6863	Remote Similarity	NPD2550	Approved
0.6863	Remote Similarity	NPD2558	Approved
0.6863	Remote Similarity	NPD2549	Approved
0.6863	Remote Similarity	NPD1242	Phase 1
0.6863	Remote Similarity	NPD2552	Approved
0.6863	Remote Similarity	NPD2555	Approved
0.6863	Remote Similarity	NPD2553	Approved
0.6852	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4793	Discontinued
0.6842	Remote Similarity	NPD9538	Approved
0.6837	Remote Similarity	NPD9251	Approved
0.6827	Remote Similarity	NPD3046	Approved
0.6827	Remote Similarity	NPD3048	Approved
0.6827	Remote Similarity	NPD3047	Approved
0.6818	Remote Similarity	NPD9716	Approved
0.6818	Remote Similarity	NPD2629	Approved
0.68	Remote Similarity	NPD1989	Approved
0.6796	Remote Similarity	NPD4189	Approved
0.6796	Remote Similarity	NPD4719	Phase 2
0.6796	Remote Similarity	NPD4188	Approved
0.6778	Remote Similarity	NPD227	Approved
0.6778	Remote Similarity	NPD225	Approved
0.6768	Remote Similarity	NPD1563	Approved
0.6765	Remote Similarity	NPD9712	Approved
0.6759	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD2932	Approved
0.6754	Remote Similarity	NPD3019	Approved
0.6754	Remote Similarity	NPD4626	Approved
0.6754	Remote Similarity	NPD1751	Approved
0.6754	Remote Similarity	NPD5126	Approved
0.6754	Remote Similarity	NPD5125	Phase 3
0.6731	Remote Similarity	NPD1930	Approved
0.6731	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6647	Phase 2
0.6731	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1929	Approved
0.6729	Remote Similarity	NPD2684	Approved
0.6727	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD9490	Approved
0.67	Remote Similarity	NPD3772	Phase 3
0.67	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6049	Phase 2
0.6697	Remote Similarity	NPD228	Approved
0.6696	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4749	Approved
0.6667	Remote Similarity	NPD4105	Approved
0.6667	Remote Similarity	NPD5240	Approved
0.6667	Remote Similarity	NPD9711	Approved
0.6667	Remote Similarity	NPD5909	Discontinued
0.6667	Remote Similarity	NPD5239	Approved
0.6667	Remote Similarity	NPD5236	Approved
0.6667	Remote Similarity	NPD475	Phase 2
0.6667	Remote Similarity	NPD9273	Approved
0.6667	Remote Similarity	NPD5237	Approved
0.6667	Remote Similarity	NPD4093	Discontinued
0.6667	Remote Similarity	NPD497	Approved
0.6667	Remote Similarity	NPD9710	Approved
0.6667	Remote Similarity	NPD4102	Approved
0.6667	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5235	Approved
0.6638	Remote Similarity	NPD3092	Approved
0.6638	Remote Similarity	NPD804	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD9532	Phase 3
0.6636	Remote Similarity	NPD6406	Approved
0.6635	Remote Similarity	NPD1932	Approved
0.6635	Remote Similarity	NPD4119	Approved
0.6627	Remote Similarity	NPD675	Discontinued
0.6609	Remote Similarity	NPD2667	Approved
0.6609	Remote Similarity	NPD5306	Approved
0.6609	Remote Similarity	NPD2286	Discontinued
0.6609	Remote Similarity	NPD5305	Approved
0.6609	Remote Similarity	NPD2668	Approved
0.6609	Remote Similarity	NPD4589	Approved
0.6609	Remote Similarity	NPD3095	Discontinued
0.6607	Remote Similarity	NPD7157	Approved
0.6606	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2201	Approved
0.6593	Remote Similarity	NPD9088	Approved
0.6581	Remote Similarity	NPD2230	Approved
0.6581	Remote Similarity	NPD2232	Approved
0.6581	Remote Similarity	NPD2233	Approved
0.6579	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5303	Approved
0.6579	Remote Similarity	NPD5304	Approved
0.6577	Remote Similarity	NPD495	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