NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.12
Volume:	228.883
LogP:	1.054
LogD:	0.879
LogS:	-1.992
# Rotatable Bonds:	4
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	4.249
Fsp3:	0.75
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:	-4.645
MDCK Permeability:	3.459086292423308e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.239
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	24.89004898071289%
Volume Distribution (VD):	1.624
Pgp-substrate:	66.17898559570312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.386
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.715
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.214
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.063
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	5.653
Half-life (T1/2):	0.862

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.457
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.277
Rat Oral Acute Toxicity:	0.452
Maximum Recommended Daily Dose:	0.726
Skin Sensitization:	0.823
Carcinogencity:	0.183
Eye Corrosion:	0.006
Eye Irritation:	0.109
Respiratory Toxicity:	0.236

Download Data

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

Natural Product: NPC474278

Natural Product ID:	NPC474278
*Common Name:**	(3Ar,7Ar)-6-Hydroxy-2,3,3A,6,7,7A-Hexahydrobenzofuran-3A-Yl Butyrate
IUPAC Name:	[(3aR,7aR)-6-hydroxy-3,6,7,7a-tetrahydro-2H-1-benzofuran-3a-yl] butanoate
Synonyms:
Standard InCHIKey:	BLGCXVWHHHCHBY-YWTFCRFGSA-N
Standard InCHI:	InChI=1S/C12H18O4/c1-2-3-11(14)16-12-5-4-9(13)8-10(12)15-7-6-12/h4-5,9-10,13H,2-3,6-8H2,1H3/t9?,10-,12+/m1/s1
SMILES:	CCCC(=O)O[C@]12CCO[C@@H]2CC(C=C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464643
PubChem CID:	44567098
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO33459	cornus controversa	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3236014]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[473477]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.8	ug.mL-1	PMID[473477]

☑ 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 NPC474278 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	137
0.1-0.2	1065
0.2-0.3	5012
0.3-0.4	14724
0.4-0.5	11432
0.5-0.6	6890
0.6-0.7	2928
0.7-0.8	495
0.8-0.85	10
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC475210
0.9577	High Similarity	NPC474280
0.9342	High Similarity	NPC474252
0.8194	Intermediate Similarity	NPC473722
0.8193	Intermediate Similarity	NPC478112
0.8049	Intermediate Similarity	NPC44261
0.8025	Intermediate Similarity	NPC52861
0.8025	Intermediate Similarity	NPC24417
0.8	Intermediate Similarity	NPC473981
0.8	Intermediate Similarity	NPC473980
0.7927	Intermediate Similarity	NPC229825
0.7875	Intermediate Similarity	NPC267231
0.7875	Intermediate Similarity	NPC475699
0.7848	Intermediate Similarity	NPC68819
0.7831	Intermediate Similarity	NPC473390
0.7831	Intermediate Similarity	NPC169575
0.7831	Intermediate Similarity	NPC40746
0.7831	Intermediate Similarity	NPC131669
0.7831	Intermediate Similarity	NPC474809
0.7831	Intermediate Similarity	NPC52923
0.7778	Intermediate Similarity	NPC167881
0.7778	Intermediate Similarity	NPC471537
0.7778	Intermediate Similarity	NPC98557
0.7765	Intermediate Similarity	NPC469910
0.7765	Intermediate Similarity	NPC278283
0.775	Intermediate Similarity	NPC7563
0.775	Intermediate Similarity	NPC116177
0.775	Intermediate Similarity	NPC320630
0.7738	Intermediate Similarity	NPC114979
0.7738	Intermediate Similarity	NPC158756
0.7738	Intermediate Similarity	NPC191476
0.7738	Intermediate Similarity	NPC141193
0.7738	Intermediate Similarity	NPC96259
0.7738	Intermediate Similarity	NPC32676
0.7738	Intermediate Similarity	NPC476804
0.7733	Intermediate Similarity	NPC25298
0.7711	Intermediate Similarity	NPC89555
0.7711	Intermediate Similarity	NPC475690
0.7662	Intermediate Similarity	NPC4299
0.7654	Intermediate Similarity	NPC196653
0.7654	Intermediate Similarity	NPC108816
0.7654	Intermediate Similarity	NPC93763
0.7654	Intermediate Similarity	NPC127526
0.7654	Intermediate Similarity	NPC471465
0.7647	Intermediate Similarity	NPC255307
0.7647	Intermediate Similarity	NPC165162
0.7647	Intermediate Similarity	NPC470755
0.7647	Intermediate Similarity	NPC21469
0.764	Intermediate Similarity	NPC475912
0.7625	Intermediate Similarity	NPC190400
0.7625	Intermediate Similarity	NPC49392
0.7619	Intermediate Similarity	NPC116543
0.7619	Intermediate Similarity	NPC59097
0.7614	Intermediate Similarity	NPC475855
0.7614	Intermediate Similarity	NPC474232
0.7595	Intermediate Similarity	NPC114727
0.7595	Intermediate Similarity	NPC476590
0.759	Intermediate Similarity	NPC474894
0.759	Intermediate Similarity	NPC112868
0.759	Intermediate Similarity	NPC475944
0.7586	Intermediate Similarity	NPC473715
0.7586	Intermediate Similarity	NPC136879
0.7586	Intermediate Similarity	NPC476803
0.7564	Intermediate Similarity	NPC477087
0.7564	Intermediate Similarity	NPC477086
0.7561	Intermediate Similarity	NPC291260
0.7561	Intermediate Similarity	NPC321728
0.7558	Intermediate Similarity	NPC475461
0.7558	Intermediate Similarity	NPC305475
0.7558	Intermediate Similarity	NPC311163
0.7556	Intermediate Similarity	NPC57405
0.7556	Intermediate Similarity	NPC303942
0.7534	Intermediate Similarity	NPC55376
0.7532	Intermediate Similarity	NPC101622
0.7532	Intermediate Similarity	NPC130618
0.7531	Intermediate Similarity	NPC475711
0.7531	Intermediate Similarity	NPC40049
0.7529	Intermediate Similarity	NPC78673
0.7529	Intermediate Similarity	NPC186155
0.7529	Intermediate Similarity	NPC243618
0.7529	Intermediate Similarity	NPC70424
0.7529	Intermediate Similarity	NPC160517
0.7529	Intermediate Similarity	NPC295799
0.7528	Intermediate Similarity	NPC473321
0.75	Intermediate Similarity	NPC218927
0.75	Intermediate Similarity	NPC206001
0.75	Intermediate Similarity	NPC473948
0.75	Intermediate Similarity	NPC133450
0.75	Intermediate Similarity	NPC478110
0.7473	Intermediate Similarity	NPC36954
0.7473	Intermediate Similarity	NPC270013
0.7473	Intermediate Similarity	NPC14961
0.7468	Intermediate Similarity	NPC470435
0.7468	Intermediate Similarity	NPC477085
0.7467	Intermediate Similarity	NPC96414
0.7467	Intermediate Similarity	NPC19769
0.7444	Intermediate Similarity	NPC162205
0.7444	Intermediate Similarity	NPC295204
0.7444	Intermediate Similarity	NPC273579
0.7444	Intermediate Similarity	NPC288240
0.7442	Intermediate Similarity	NPC471156
0.7442	Intermediate Similarity	NPC11804
0.7442	Intermediate Similarity	NPC471494
0.7439	Intermediate Similarity	NPC248775
0.7439	Intermediate Similarity	NPC39547
0.7439	Intermediate Similarity	NPC323249
0.7439	Intermediate Similarity	NPC474816
0.7439	Intermediate Similarity	NPC209135
0.7439	Intermediate Similarity	NPC326753
0.7439	Intermediate Similarity	NPC27949
0.7439	Intermediate Similarity	NPC260814
0.7436	Intermediate Similarity	NPC129630
0.7436	Intermediate Similarity	NPC473361
0.7436	Intermediate Similarity	NPC329904
0.7419	Intermediate Similarity	NPC203627
0.7416	Intermediate Similarity	NPC473448
0.7416	Intermediate Similarity	NPC144133
0.7416	Intermediate Similarity	NPC179394
0.7416	Intermediate Similarity	NPC177668
0.7416	Intermediate Similarity	NPC476004
0.7416	Intermediate Similarity	NPC473619
0.7416	Intermediate Similarity	NPC474761
0.7412	Intermediate Similarity	NPC250315
0.7412	Intermediate Similarity	NPC161045
0.7412	Intermediate Similarity	NPC170286
0.7407	Intermediate Similarity	NPC474197
0.7396	Intermediate Similarity	NPC220964
0.7396	Intermediate Similarity	NPC475676
0.7391	Intermediate Similarity	NPC476315
0.7391	Intermediate Similarity	NPC279621
0.7386	Intermediate Similarity	NPC309656
0.7386	Intermediate Similarity	NPC476805
0.7386	Intermediate Similarity	NPC477302
0.7386	Intermediate Similarity	NPC475819
0.7386	Intermediate Similarity	NPC287089
0.7381	Intermediate Similarity	NPC325031
0.7381	Intermediate Similarity	NPC316844
0.7381	Intermediate Similarity	NPC470241
0.7368	Intermediate Similarity	NPC276299
0.7368	Intermediate Similarity	NPC201356
0.7363	Intermediate Similarity	NPC474035
0.7363	Intermediate Similarity	NPC81386
0.7356	Intermediate Similarity	NPC116575
0.7356	Intermediate Similarity	NPC61527
0.7349	Intermediate Similarity	NPC470148
0.7349	Intermediate Similarity	NPC89128
0.7349	Intermediate Similarity	NPC99651
0.7349	Intermediate Similarity	NPC139712
0.7349	Intermediate Similarity	NPC86971
0.7349	Intermediate Similarity	NPC470149
0.7349	Intermediate Similarity	NPC226226
0.7349	Intermediate Similarity	NPC55304
0.7349	Intermediate Similarity	NPC180725
0.7342	Intermediate Similarity	NPC474590
0.7333	Intermediate Similarity	NPC475221
0.7333	Intermediate Similarity	NPC184463
0.7333	Intermediate Similarity	NPC30515
0.7333	Intermediate Similarity	NPC208839
0.7326	Intermediate Similarity	NPC31086
0.7326	Intermediate Similarity	NPC475035
0.7326	Intermediate Similarity	NPC474865
0.7317	Intermediate Similarity	NPC474026
0.7317	Intermediate Similarity	NPC476439
0.7317	Intermediate Similarity	NPC97516
0.7317	Intermediate Similarity	NPC476028
0.7317	Intermediate Similarity	NPC171204
0.7317	Intermediate Similarity	NPC141789
0.7317	Intermediate Similarity	NPC262747
0.7317	Intermediate Similarity	NPC84360
0.7317	Intermediate Similarity	NPC315394
0.7312	Intermediate Similarity	NPC205143
0.7308	Intermediate Similarity	NPC475982
0.7308	Intermediate Similarity	NPC475004
0.7308	Intermediate Similarity	NPC470436
0.7303	Intermediate Similarity	NPC474032
0.7303	Intermediate Similarity	NPC473564
0.7297	Intermediate Similarity	NPC113293
0.7294	Intermediate Similarity	NPC475046
0.7294	Intermediate Similarity	NPC474959
0.7294	Intermediate Similarity	NPC310450
0.7294	Intermediate Similarity	NPC11383
0.7292	Intermediate Similarity	NPC4620
0.7284	Intermediate Similarity	NPC473582
0.7284	Intermediate Similarity	NPC60718
0.7284	Intermediate Similarity	NPC329852
0.7283	Intermediate Similarity	NPC471142
0.7283	Intermediate Similarity	NPC477922
0.7283	Intermediate Similarity	NPC304886
0.7273	Intermediate Similarity	NPC160138
0.7273	Intermediate Similarity	NPC478097
0.7273	Intermediate Similarity	NPC478100
0.7273	Intermediate Similarity	NPC473357
0.7273	Intermediate Similarity	NPC45409
0.7273	Intermediate Similarity	NPC179659
0.7273	Intermediate Similarity	NPC193029
0.7273	Intermediate Similarity	NPC471055
0.7273	Intermediate Similarity	NPC471056
0.7273	Intermediate Similarity	NPC316629
0.7262	Intermediate Similarity	NPC133226
0.7262	Intermediate Similarity	NPC470147

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 NPC474278 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	122
0.1-0.2	1497
0.2-0.3	3915
0.3-0.4	2549
0.4-0.5	717
0.5-0.6	287
0.6-0.7	54
0.7-0.8	9
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
0.7683	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4822	Approved
0.747	Intermediate Similarity	NPD4819	Approved
0.747	Intermediate Similarity	NPD4820	Approved
0.747	Intermediate Similarity	NPD4821	Approved
0.7439	Intermediate Similarity	NPD4271	Approved
0.7439	Intermediate Similarity	NPD4268	Approved
0.7356	Intermediate Similarity	NPD4249	Approved
0.7273	Intermediate Similarity	NPD4251	Approved
0.7273	Intermediate Similarity	NPD4250	Approved
0.7222	Intermediate Similarity	NPD46	Approved
0.7222	Intermediate Similarity	NPD6698	Approved
0.7209	Intermediate Similarity	NPD7154	Phase 3
0.7053	Intermediate Similarity	NPD4225	Approved
0.7053	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7838	Discovery
0.6957	Remote Similarity	NPD7983	Approved
0.6932	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5362	Discontinued
0.6796	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5344	Discontinued
0.6711	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4269	Approved
0.6705	Remote Similarity	NPD6435	Approved
0.6705	Remote Similarity	NPD4270	Approved
0.6702	Remote Similarity	NPD5779	Approved
0.6702	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5785	Approved
0.6629	Remote Similarity	NPD5332	Approved
0.6629	Remote Similarity	NPD5331	Approved
0.6628	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD368	Approved
0.6596	Remote Similarity	NPD7637	Suspended
0.6593	Remote Similarity	NPD5786	Approved
0.6591	Remote Similarity	NPD5369	Approved
0.6591	Remote Similarity	NPD4790	Discontinued
0.6582	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5363	Approved
0.6477	Remote Similarity	NPD5368	Approved
0.6471	Remote Similarity	NPD8039	Approved
0.6465	Remote Similarity	NPD6648	Approved
0.6447	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD8517	Approved
0.6396	Remote Similarity	NPD8513	Phase 3
0.6396	Remote Similarity	NPD8515	Approved
0.6396	Remote Similarity	NPD8516	Approved
0.6383	Remote Similarity	NPD6101	Approved
0.6383	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5370	Suspended
0.6381	Remote Similarity	NPD6371	Approved
0.633	Remote Similarity	NPD7115	Discovery
0.6327	Remote Similarity	NPD7839	Suspended
0.6304	Remote Similarity	NPD1694	Approved
0.6267	Remote Similarity	NPD342	Phase 1
0.625	Remote Similarity	NPD3197	Phase 1
0.625	Remote Similarity	NPD6411	Approved
0.6234	Remote Similarity	NPD6109	Phase 1
0.6211	Remote Similarity	NPD1695	Approved
0.619	Remote Similarity	NPD6686	Approved
0.6154	Remote Similarity	NPD5209	Approved
0.6139	Remote Similarity	NPD7640	Approved
0.6139	Remote Similarity	NPD7639	Approved
0.6136	Remote Similarity	NPD4756	Discovery
0.6121	Remote Similarity	NPD8074	Phase 3
0.6111	Remote Similarity	NPD6053	Discontinued
0.6087	Remote Similarity	NPD6110	Phase 1
0.6075	Remote Similarity	NPD6421	Discontinued
0.6049	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4732	Discontinued
0.604	Remote Similarity	NPD7638	Approved
0.6026	Remote Similarity	NPD69	Approved
0.6026	Remote Similarity	NPD9119	Approved
0.6022	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.602	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD7524	Approved
0.5981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5282	Discontinued
0.5946	Remote Similarity	NPD6927	Phase 3
0.5914	Remote Similarity	NPD6695	Phase 3
0.5897	Remote Similarity	NPD9118	Approved
0.5893	Remote Similarity	NPD7505	Discontinued
0.5876	Remote Similarity	NPD6051	Approved
0.5872	Remote Similarity	NPD2204	Approved
0.5818	Remote Similarity	NPD8297	Approved
0.581	Remote Similarity	NPD6647	Phase 2
0.581	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5697	Approved
0.5789	Remote Similarity	NPD1696	Phase 3
0.5789	Remote Similarity	NPD3172	Approved
0.5784	Remote Similarity	NPD6083	Phase 2
0.5784	Remote Similarity	NPD6084	Phase 2
0.578	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD8273	Phase 1
0.5761	Remote Similarity	NPD7514	Phase 3
0.5761	Remote Similarity	NPD7332	Phase 2
0.5743	Remote Similarity	NPD5695	Phase 3
0.5741	Remote Similarity	NPD6899	Approved
0.5741	Remote Similarity	NPD6881	Approved
0.573	Remote Similarity	NPD8264	Approved
0.5729	Remote Similarity	NPD6422	Discontinued
0.5727	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD7331	Phase 2
0.5714	Remote Similarity	NPD3195	Phase 2
0.5714	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4266	Approved
0.5714	Remote Similarity	NPD3194	Approved
0.5701	Remote Similarity	NPD6402	Approved
0.5701	Remote Similarity	NPD5739	Approved
0.5701	Remote Similarity	NPD7128	Approved
0.5701	Remote Similarity	NPD6675	Approved
0.57	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.569	Remote Similarity	NPD7503	Approved
0.569	Remote Similarity	NPD8444	Approved
0.5688	Remote Similarity	NPD6014	Approved
0.5688	Remote Similarity	NPD6013	Approved
0.5688	Remote Similarity	NPD6012	Approved
0.5686	Remote Similarity	NPD4228	Discovery
0.5684	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD3173	Approved
0.5676	Remote Similarity	NPD969	Suspended
0.567	Remote Similarity	NPD7750	Discontinued
0.5648	Remote Similarity	NPD5701	Approved
0.5638	Remote Similarity	NPD3667	Approved
0.5636	Remote Similarity	NPD7102	Approved
0.5636	Remote Similarity	NPD6883	Approved
0.5636	Remote Similarity	NPD7290	Approved
0.5636	Remote Similarity	NPD2067	Discontinued
0.563	Remote Similarity	NPD8451	Approved
0.561	Remote Similarity	NPD4194	Approved
0.561	Remote Similarity	NPD4191	Approved
0.561	Remote Similarity	NPD4193	Approved
0.561	Remote Similarity	NPD4192	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