NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	1.636
LogD:	1.649
LogS:	-2.396
# Rotatable Bonds:	3
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.763
Synthetic Accessibility Score:	3.627
Fsp3:	0.6
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:	-4.732
MDCK Permeability:	9.03264299267903e-06
Pgp-inhibitor:	0.013
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.29
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.149
Plasma Protein Binding (PPB):	44.950782775878906%
Volume Distribution (VD):	0.908
Pgp-substrate:	67.0708999633789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.457
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.094
CYP3A4-substrate:	0.468

ADMET: Excretion

Clearance (CL):	4.61
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.462
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.217
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.072

Download Data

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

Natural Product: NPC289117

Natural Product ID:	NPC289117
*Common Name:**	11-Hydroxydehydrobotrydienol
IUPAC Name:	[(3S)-3,4-bis(hydroxymethyl)-1,1,3-trimethyl-2H-inden-5-yl]methanol
Synonyms:	11-Hydroxydehydrobotrydienol
Standard InCHIKey:	JUCMRFKOKIZVPS-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-14(2)8-15(3,9-18)13-11(7-17)10(6-16)4-5-12(13)14/h4-5,16-18H,6-9H2,1-3H3/t15-/m1/s1
SMILES:	OCc1ccc2c(c1CO)[C@@](C)(CO)CC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445801
PubChem CID:	10658336
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000027] Indanes

*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
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	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
Others	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	ID50	>	10.0	ug ml-1	PMID[451306]
NPT453	Cell Line	HT-1080	Homo sapiens	ID50	>	10.0	ug ml-1	PMID[451306]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	ID50	>	10.0	ug ml-1	PMID[451306]
NPT27	Others	Unspecified		ID50	>	10.0	ug ml-1	PMID[451306]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ID50	>	10.0	ug ml-1	PMID[451306]

☑ 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 NPC289117 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	202
0.1-0.2	1293
0.2-0.3	2686
0.3-0.4	10962
0.4-0.5	15435
0.5-0.6	9727
0.6-0.7	2049
0.7-0.8	308
0.8-0.85	26
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8936	High Similarity	NPC79917
0.89	High Similarity	NPC315794
0.8842	High Similarity	NPC314690
0.8812	High Similarity	NPC471133
0.8614	High Similarity	NPC19856
0.8526	High Similarity	NPC1793
0.8505	High Similarity	NPC169616
0.8454	Intermediate Similarity	NPC128645
0.844	Intermediate Similarity	NPC472862
0.8404	Intermediate Similarity	NPC93843
0.8381	Intermediate Similarity	NPC149455
0.8381	Intermediate Similarity	NPC64642
0.8381	Intermediate Similarity	NPC472982
0.8286	Intermediate Similarity	NPC472979
0.8286	Intermediate Similarity	NPC27252
0.8286	Intermediate Similarity	NPC472980
0.828	Intermediate Similarity	NPC172984
0.8269	Intermediate Similarity	NPC243601
0.8235	Intermediate Similarity	NPC469481
0.8235	Intermediate Similarity	NPC245927
0.8214	Intermediate Similarity	NPC238582
0.8211	Intermediate Similarity	NPC474211
0.8173	Intermediate Similarity	NPC56168
0.8144	Intermediate Similarity	NPC199567
0.8105	Intermediate Similarity	NPC474354
0.8021	Intermediate Similarity	NPC243166
0.802	Intermediate Similarity	NPC21959
0.8	Intermediate Similarity	NPC168855
0.8	Intermediate Similarity	NPC304538
0.7982	Intermediate Similarity	NPC471188
0.7982	Intermediate Similarity	NPC233923
0.7982	Intermediate Similarity	NPC146673
0.7982	Intermediate Similarity	NPC111108
0.798	Intermediate Similarity	NPC220596
0.7944	Intermediate Similarity	NPC112903
0.7857	Intermediate Similarity	NPC469719
0.7789	Intermediate Similarity	NPC87299
0.7789	Intermediate Similarity	NPC329319
0.7789	Intermediate Similarity	NPC103326
0.7789	Intermediate Similarity	NPC99394
0.7788	Intermediate Similarity	NPC247858
0.7788	Intermediate Similarity	NPC154511
0.7788	Intermediate Similarity	NPC474358
0.7788	Intermediate Similarity	NPC474387
0.7788	Intermediate Similarity	NPC137496
0.7788	Intermediate Similarity	NPC257540
0.7788	Intermediate Similarity	NPC469663
0.7788	Intermediate Similarity	NPC92
0.7748	Intermediate Similarity	NPC302371
0.7727	Intermediate Similarity	NPC133308
0.7727	Intermediate Similarity	NPC132720
0.7706	Intermediate Similarity	NPC306295
0.7706	Intermediate Similarity	NPC64586
0.7685	Intermediate Similarity	NPC185763
0.7685	Intermediate Similarity	NPC83409
0.7685	Intermediate Similarity	NPC310456
0.7684	Intermediate Similarity	NPC133050
0.7684	Intermediate Similarity	NPC117180
0.7672	Intermediate Similarity	NPC133302
0.7672	Intermediate Similarity	NPC68339
0.7664	Intermediate Similarity	NPC475225
0.7652	Intermediate Similarity	NPC164649
0.7652	Intermediate Similarity	NPC48342
0.7642	Intermediate Similarity	NPC154905
0.7642	Intermediate Similarity	NPC60373
0.7634	Intermediate Similarity	NPC66655
0.7632	Intermediate Similarity	NPC242764
0.7632	Intermediate Similarity	NPC212891
0.7632	Intermediate Similarity	NPC105141
0.7615	Intermediate Similarity	NPC249811
0.7607	Intermediate Similarity	NPC328504
0.7596	Intermediate Similarity	NPC324602
0.7593	Intermediate Similarity	NPC471186
0.7586	Intermediate Similarity	NPC469644
0.7573	Intermediate Similarity	NPC289769
0.757	Intermediate Similarity	NPC471228
0.757	Intermediate Similarity	NPC235762
0.7568	Intermediate Similarity	NPC475002
0.7568	Intermediate Similarity	NPC95126
0.7565	Intermediate Similarity	NPC477136
0.7565	Intermediate Similarity	NPC172219
0.7565	Intermediate Similarity	NPC304510
0.7553	Intermediate Similarity	NPC224544
0.7547	Intermediate Similarity	NPC174911
0.7547	Intermediate Similarity	NPC211885
0.7544	Intermediate Similarity	NPC192948
0.7544	Intermediate Similarity	NPC35797
0.7542	Intermediate Similarity	NPC77569
0.7542	Intermediate Similarity	NPC142198
0.7524	Intermediate Similarity	NPC474073
0.7523	Intermediate Similarity	NPC94751
0.7523	Intermediate Similarity	NPC142326
0.7521	Intermediate Similarity	NPC133389
0.7521	Intermediate Similarity	NPC234337
0.7521	Intermediate Similarity	NPC183339
0.75	Intermediate Similarity	NPC469609
0.75	Intermediate Similarity	NPC222146
0.75	Intermediate Similarity	NPC242628
0.75	Intermediate Similarity	NPC322753
0.75	Intermediate Similarity	NPC154030
0.75	Intermediate Similarity	NPC272029
0.75	Intermediate Similarity	NPC471671
0.7479	Intermediate Similarity	NPC273336
0.7479	Intermediate Similarity	NPC182333
0.7478	Intermediate Similarity	NPC308311
0.7478	Intermediate Similarity	NPC477137
0.7478	Intermediate Similarity	NPC38893
0.7478	Intermediate Similarity	NPC219112
0.7478	Intermediate Similarity	NPC308828
0.7456	Intermediate Similarity	NPC274839
0.7456	Intermediate Similarity	NPC268160
0.7455	Intermediate Similarity	NPC66834
0.7453	Intermediate Similarity	NPC128723
0.7453	Intermediate Similarity	NPC252821
0.7453	Intermediate Similarity	NPC299762
0.7453	Intermediate Similarity	NPC33675
0.7453	Intermediate Similarity	NPC122005
0.7434	Intermediate Similarity	NPC228425
0.7431	Intermediate Similarity	NPC47284
0.7423	Intermediate Similarity	NPC106313
0.7417	Intermediate Similarity	NPC77691
0.7407	Intermediate Similarity	NPC269212
0.7404	Intermediate Similarity	NPC152415
0.7404	Intermediate Similarity	NPC27323
0.7404	Intermediate Similarity	NPC316301
0.7396	Intermediate Similarity	NPC328178
0.7395	Intermediate Similarity	NPC18785
0.7395	Intermediate Similarity	NPC293831
0.7395	Intermediate Similarity	NPC369
0.7391	Intermediate Similarity	NPC147179
0.7391	Intermediate Similarity	NPC9274
0.7383	Intermediate Similarity	NPC225506
0.7364	Intermediate Similarity	NPC53740
0.735	Intermediate Similarity	NPC254233
0.7345	Intermediate Similarity	NPC469912
0.7339	Intermediate Similarity	NPC472222
0.7339	Intermediate Similarity	NPC82712
0.7339	Intermediate Similarity	NPC472221
0.7339	Intermediate Similarity	NPC238696
0.7333	Intermediate Similarity	NPC144682
0.7315	Intermediate Similarity	NPC252105
0.7312	Intermediate Similarity	NPC108218
0.7311	Intermediate Similarity	NPC472981
0.7308	Intermediate Similarity	NPC55903
0.7304	Intermediate Similarity	NPC221275
0.7304	Intermediate Similarity	NPC476357
0.729	Intermediate Similarity	NPC92730
0.7288	Intermediate Similarity	NPC472708
0.7288	Intermediate Similarity	NPC151197
0.7281	Intermediate Similarity	NPC250323
0.7273	Intermediate Similarity	NPC117115
0.7273	Intermediate Similarity	NPC471350
0.7265	Intermediate Similarity	NPC45794
0.7265	Intermediate Similarity	NPC320864
0.7264	Intermediate Similarity	NPC202986
0.7257	Intermediate Similarity	NPC474057
0.7236	Intermediate Similarity	NPC5486
0.7232	Intermediate Similarity	NPC262365
0.7227	Intermediate Similarity	NPC99734
0.7222	Intermediate Similarity	NPC72729
0.7217	Intermediate Similarity	NPC196673
0.7212	Intermediate Similarity	NPC155908
0.7212	Intermediate Similarity	NPC306074
0.7207	Intermediate Similarity	NPC21594
0.7207	Intermediate Similarity	NPC37914
0.72	Intermediate Similarity	NPC99482
0.7196	Intermediate Similarity	NPC77492
0.7196	Intermediate Similarity	NPC6597
0.7196	Intermediate Similarity	NPC79241
0.7196	Intermediate Similarity	NPC225464
0.7193	Intermediate Similarity	NPC176279
0.7193	Intermediate Similarity	NPC77772
0.7193	Intermediate Similarity	NPC260323
0.7193	Intermediate Similarity	NPC471189
0.7193	Intermediate Similarity	NPC266937
0.7193	Intermediate Similarity	NPC470770
0.7193	Intermediate Similarity	NPC66208
0.7193	Intermediate Similarity	NPC151537
0.719	Intermediate Similarity	NPC321402
0.719	Intermediate Similarity	NPC297057
0.7182	Intermediate Similarity	NPC327811
0.7182	Intermediate Similarity	NPC323810
0.7182	Intermediate Similarity	NPC254965
0.717	Intermediate Similarity	NPC313650
0.7168	Intermediate Similarity	NPC58865
0.7165	Intermediate Similarity	NPC85595
0.7156	Intermediate Similarity	NPC471578
0.7156	Intermediate Similarity	NPC101025
0.7155	Intermediate Similarity	NPC12656
0.7155	Intermediate Similarity	NPC471534
0.7155	Intermediate Similarity	NPC195922
0.7155	Intermediate Similarity	NPC93181
0.7154	Intermediate Similarity	NPC9180
0.7154	Intermediate Similarity	NPC100402
0.7143	Intermediate Similarity	NPC258366
0.7143	Intermediate Similarity	NPC21929
0.7143	Intermediate Similarity	NPC138117
0.7143	Intermediate Similarity	NPC320439
0.7143	Intermediate Similarity	NPC151477
0.7143	Intermediate Similarity	NPC31296

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 NPC289117 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	945
0.2-0.3	1494
0.3-0.4	2953
0.4-0.5	2243
0.5-0.6	1059
0.6-0.7	242
0.7-0.8	19
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8077	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7741	Discontinued
0.7652	Intermediate Similarity	NPD3091	Approved
0.7634	Intermediate Similarity	NPD9294	Approved
0.7542	Intermediate Similarity	NPD3092	Approved
0.7438	Intermediate Similarity	NPD3094	Phase 2
0.7404	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5125	Phase 3
0.7373	Intermediate Similarity	NPD3095	Discontinued
0.7373	Intermediate Similarity	NPD5126	Approved
0.7368	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1809	Phase 2
0.7308	Intermediate Similarity	NPD845	Approved
0.7304	Intermediate Similarity	NPD5951	Approved
0.7281	Intermediate Similarity	NPD7635	Approved
0.7227	Intermediate Similarity	NPD4059	Approved
0.7222	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD844	Approved
0.7103	Intermediate Similarity	NPD288	Approved
0.7083	Intermediate Similarity	NPD3019	Approved
0.7083	Intermediate Similarity	NPD2932	Approved
0.7059	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1088	Approved
0.7	Intermediate Similarity	NPD1710	Approved
0.6991	Remote Similarity	NPD2342	Discontinued
0.699	Remote Similarity	NPD1101	Approved
0.6972	Remote Similarity	NPD3020	Approved
0.6942	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD1693	Approved
0.6916	Remote Similarity	NPD6049	Phase 2
0.6916	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1616	Discontinued
0.6905	Remote Similarity	NPD5736	Approved
0.6897	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2629	Approved
0.6863	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1089	Approved
0.6857	Remote Similarity	NPD1090	Approved
0.6857	Remote Similarity	NPD1086	Approved
0.6852	Remote Similarity	NPD2860	Approved
0.6852	Remote Similarity	NPD2859	Approved
0.6842	Remote Similarity	NPD6406	Approved
0.6825	Remote Similarity	NPD4624	Approved
0.6822	Remote Similarity	NPD3719	Approved
0.6822	Remote Similarity	NPD3718	Approved
0.6807	Remote Similarity	NPD4198	Discontinued
0.6803	Remote Similarity	NPD7725	Approved
0.68	Remote Similarity	NPD9250	Approved
0.68	Remote Similarity	NPD6696	Suspended
0.6797	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5765	Approved
0.6783	Remote Similarity	NPD4718	Approved
0.6783	Remote Similarity	NPD4720	Approved
0.6783	Remote Similarity	NPD4717	Approved
0.678	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD800	Approved
0.6759	Remote Similarity	NPD2933	Approved
0.6759	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2934	Approved
0.6759	Remote Similarity	NPD4814	Discontinued
0.6754	Remote Similarity	NPD6685	Approved
0.675	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD9495	Approved
0.6727	Remote Similarity	NPD9611	Approved
0.6727	Remote Similarity	NPD9609	Approved
0.6727	Remote Similarity	NPD9612	Approved
0.6724	Remote Similarity	NPD4750	Phase 3
0.6718	Remote Similarity	NPD5735	Approved
0.6696	Remote Similarity	NPD855	Approved
0.6696	Remote Similarity	NPD940	Approved
0.6696	Remote Similarity	NPD846	Approved
0.6696	Remote Similarity	NPD854	Approved
0.6694	Remote Similarity	NPD5618	Discontinued
0.6693	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1409	Phase 3
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3620	Phase 2
0.6641	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4140	Approved
0.6637	Remote Similarity	NPD3683	Approved
0.6637	Remote Similarity	NPD3681	Approved
0.6613	Remote Similarity	NPD3026	Approved
0.6613	Remote Similarity	NPD3023	Approved
0.6587	Remote Similarity	NPD5327	Phase 3
0.6585	Remote Similarity	NPD3025	Approved
0.6585	Remote Similarity	NPD3024	Approved
0.6583	Remote Similarity	NPD497	Approved
0.6579	Remote Similarity	NPD1237	Approved
0.6574	Remote Similarity	NPD752	Approved
0.6571	Remote Similarity	NPD1087	Approved
0.6567	Remote Similarity	NPD7305	Phase 1
0.6567	Remote Similarity	NPD7742	Approved
0.6567	Remote Similarity	NPD7743	Approved
0.6562	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6085	Phase 2
0.6562	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4818	Approved
0.6549	Remote Similarity	NPD4817	Approved
0.6549	Remote Similarity	NPD4719	Phase 2
0.6541	Remote Similarity	NPD6353	Approved
0.6538	Remote Similarity	NPD111	Approved
0.6532	Remote Similarity	NPD1751	Approved
0.6529	Remote Similarity	NPD7157	Approved
0.6514	Remote Similarity	NPD720	Approved
0.6514	Remote Similarity	NPD719	Approved
0.6509	Remote Similarity	NPD531	Approved
0.6505	Remote Similarity	NPD3971	Phase 1
0.65	Remote Similarity	NPD498	Approved
0.65	Remote Similarity	NPD495	Approved
0.65	Remote Similarity	NPD496	Approved
0.6493	Remote Similarity	NPD5886	Approved
0.6493	Remote Similarity	NPD41	Approved
0.6491	Remote Similarity	NPD6647	Phase 2
0.6491	Remote Similarity	NPD3682	Approved
0.6491	Remote Similarity	NPD3680	Approved
0.6481	Remote Similarity	NPD1239	Approved
0.6475	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1445	Approved
0.6466	Remote Similarity	NPD1444	Approved
0.6466	Remote Similarity	NPD7431	Approved
0.6466	Remote Similarity	NPD7430	Approved
0.6452	Remote Similarity	NPD5691	Approved
0.6446	Remote Similarity	NPD4766	Approved
0.6441	Remote Similarity	NPD3021	Approved
0.6441	Remote Similarity	NPD1792	Phase 2
0.6441	Remote Similarity	NPD3022	Approved
0.6435	Remote Similarity	NPD315	Approved
0.6435	Remote Similarity	NPD314	Approved
0.6435	Remote Similarity	NPD311	Approved
0.6435	Remote Similarity	NPD3048	Approved
0.6435	Remote Similarity	NPD309	Approved
0.6435	Remote Similarity	NPD3047	Approved
0.6435	Remote Similarity	NPD3046	Approved
0.6435	Remote Similarity	NPD10	Approved
0.6435	Remote Similarity	NPD310	Approved
0.6429	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7610	Discontinued
0.6422	Remote Similarity	NPD9251	Approved
0.6418	Remote Similarity	NPD4097	Suspended
0.641	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2286	Discontinued
0.6396	Remote Similarity	NPD1989	Approved
0.6393	Remote Similarity	NPD4031	Approved
0.6393	Remote Similarity	NPD4032	Approved
0.6387	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD3638	Discontinued
0.6372	Remote Similarity	NPD2066	Phase 3
0.6371	Remote Similarity	NPD4479	Discontinued
0.6371	Remote Similarity	NPD7009	Phase 2
0.6364	Remote Similarity	NPD1398	Phase 1
0.6364	Remote Similarity	NPD6010	Discontinued
0.6364	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD2182	Approved
0.6356	Remote Similarity	NPD2684	Approved
0.635	Remote Similarity	NPD5762	Approved
0.635	Remote Similarity	NPD5763	Approved
0.6349	Remote Similarity	NPD3898	Approved
0.6349	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD3896	Approved
0.6349	Remote Similarity	NPD3897	Approved
0.6349	Remote Similarity	NPD3895	Approved
0.6348	Remote Similarity	NPD4656	Approved
0.6348	Remote Similarity	NPD4229	Approved
0.6348	Remote Similarity	NPD4658	Approved
0.6348	Remote Similarity	NPD4231	Approved
0.6346	Remote Similarity	NPD9491	Approved
0.6341	Remote Similarity	NPD3123	Discovery
0.6339	Remote Similarity	NPD1565	Approved
0.6339	Remote Similarity	NPD1564	Approved
0.6339	Remote Similarity	NPD1566	Phase 3
0.6333	Remote Similarity	NPD6912	Phase 3
0.633	Remote Similarity	NPD530	Approved
0.6328	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.632	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.632	Remote Similarity	NPD1651	Approved
0.6311	Remote Similarity	NPD1793	Approved
0.6311	Remote Similarity	NPD1791	Approved
0.6311	Remote Similarity	NPD9618	Approved
0.6311	Remote Similarity	NPD226	Approved
0.6311	Remote Similarity	NPD9614	Approved
0.6303	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD9249	Phase 1
0.6296	Remote Similarity	NPD2157	Approved
0.6293	Remote Similarity	NPD164	Approved
0.6288	Remote Similarity	NPD4625	Phase 3
0.6286	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD8131	Suspended
0.6281	Remote Similarity	NPD6858	Approved
0.6281	Remote Similarity	NPD7094	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