NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.07
Volume:	229.714
LogP:	1.192
LogD:	1.162
LogS:	-2.166
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.733
Synthetic Accessibility Score:	3.734
Fsp3:	0.308
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:	-4.984
MDCK Permeability:	2.3677677745581605e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.097
20% Bioavailability (F20%):	0.104
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	77.72269439697266%
Volume Distribution (VD):	1.76
Pgp-substrate:	17.82621955871582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.265
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.146
CYP2C19-substrate:	0.331
CYP2C9-inhibitor:	0.104
CYP2C9-substrate:	0.147
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.192
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	4.909
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.456
Drug-inuced Liver Injury (DILI):	0.123
AMES Toxicity:	0.202
Rat Oral Acute Toxicity:	0.497
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.606
Carcinogencity:	0.055
Eye Corrosion:	0.011
Eye Irritation:	0.131
Respiratory Toxicity:	0.528

Download Data

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

Natural Product: NPC277788

Natural Product ID:	NPC277788
*Common Name:**	Altholactone
IUPAC Name:	(2R,3R,3aS,7aS)-3-hydroxy-2-phenyl-2,3,3a,7a-tetrahydrofuro[3,2-b]pyran-5-one
Synonyms:	(+)-Altholactone; Altholactone
Standard InCHIKey:	ZKIRVBNLJKGIEM-WKSBVSIWSA-N
Standard InCHI:	InChI=1S/C13H12O4/c14-10-7-6-9-13(17-10)11(15)12(16-9)8-4-2-1-3-5-8/h1-7,9,11-13,15H/t9-,11+,12+,13+/m0/s1
SMILES:	c1ccc(cc1)[C@@H]1[C@H]([C@H]2[C@H](C=CC(=O)O2)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512401
PubChem CID:	442513
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001818] Furopyrans

*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
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791471]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614426]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322367]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917277]
NPO26455	Merwilla natalensis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8674	Goniothalamus arvensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13768	Swertia marginata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15053	Menispermum cocculus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14597	Prociphilus tessellatus	Species	Pemphigidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26455	Merwilla natalensis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7589	Baccharis spartioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5379	Cortinarius sanguineus	Species	Cortinariaceae	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	16
MIC	1
Others	6

Activity Type	# Activity
Cell Line	17
Organism	3
Others	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2.9	ug.mL-1	PMID[515187]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	35.0	%	PMID[515187]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	124000.0	nM	PMID[515188]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	19000.0	nM	PMID[515188]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	19.0	%	PMID[515188]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	33.0	%	PMID[515188]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	800.0	nM	PMID[515191]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	900.0	nM	PMID[515191]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4000.0	nM	PMID[515191]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3000.0	nM	PMID[515191]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5000.0	nM	PMID[515191]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	2000.0	nM	PMID[515191]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	43400.0	nM	PMID[515191]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	78000.0	nM	PMID[515186]
NPT27	Others	Unspecified		IC50	=	120000.0	nM	PMID[515188]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	6.25	ug.mL-1	PMID[515189]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	50.0	%	PMID[515190]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	40.0	%	PMID[515190]
NPT2	Others	Unspecified		IC50	=	6700.0	nM	PMID[515191]

☑ 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 NPC277788 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	219
0.1-0.2	866
0.2-0.3	2289
0.3-0.4	7192
0.4-0.5	12019
0.5-0.6	14447
0.6-0.7	5040
0.7-0.8	572
0.8-0.85	32
0.85-0.9	8
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9505	High Similarity	NPC472315
0.9505	High Similarity	NPC37115
0.9505	High Similarity	NPC472316
0.9505	High Similarity	NPC475203
0.9505	High Similarity	NPC474376
0.95	High Similarity	NPC280616
0.95	High Similarity	NPC242913
0.95	High Similarity	NPC171831
0.94	High Similarity	NPC234305
0.9314	High Similarity	NPC136962
0.9238	High Similarity	NPC185840
0.9151	High Similarity	NPC265002
0.9057	High Similarity	NPC234376
0.8932	High Similarity	NPC85977
0.8911	High Similarity	NPC98911
0.8911	High Similarity	NPC472318
0.8835	High Similarity	NPC82426
0.8835	High Similarity	NPC91820
0.8505	High Similarity	NPC475465
0.8505	High Similarity	NPC472314
0.84	Intermediate Similarity	NPC472319
0.8364	Intermediate Similarity	NPC158282
0.8318	Intermediate Similarity	NPC472919
0.8235	Intermediate Similarity	NPC476033
0.8214	Intermediate Similarity	NPC172525
0.8198	Intermediate Similarity	NPC474314
0.812	Intermediate Similarity	NPC229600
0.81	Intermediate Similarity	NPC304760
0.8083	Intermediate Similarity	NPC79608
0.8073	Intermediate Similarity	NPC477251
0.807	Intermediate Similarity	NPC473507
0.8058	Intermediate Similarity	NPC23453
0.8056	Intermediate Similarity	NPC148060
0.8053	Intermediate Similarity	NPC474363
0.8039	Intermediate Similarity	NPC119631
0.8037	Intermediate Similarity	NPC154905
0.8037	Intermediate Similarity	NPC60373
0.802	Intermediate Similarity	NPC173443
0.7965	Intermediate Similarity	NPC474176
0.7946	Intermediate Similarity	NPC43584
0.7917	Intermediate Similarity	NPC471466
0.7913	Intermediate Similarity	NPC149691
0.7913	Intermediate Similarity	NPC210531
0.7895	Intermediate Similarity	NPC87069
0.7876	Intermediate Similarity	NPC477250
0.7838	Intermediate Similarity	NPC20485
0.7818	Intermediate Similarity	NPC152384
0.7818	Intermediate Similarity	NPC37714
0.7807	Intermediate Similarity	NPC272524
0.7805	Intermediate Similarity	NPC472707
0.78	Intermediate Similarity	NPC58616
0.7798	Intermediate Similarity	NPC160382
0.7788	Intermediate Similarity	NPC264784
0.7778	Intermediate Similarity	NPC324835
0.7778	Intermediate Similarity	NPC308619
0.7778	Intermediate Similarity	NPC127491
0.7768	Intermediate Similarity	NPC184633
0.7768	Intermediate Similarity	NPC265407
0.7768	Intermediate Similarity	NPC83628
0.7768	Intermediate Similarity	NPC474364
0.7767	Intermediate Similarity	NPC213156
0.7767	Intermediate Similarity	NPC240108
0.7739	Intermediate Similarity	NPC308744
0.7739	Intermediate Similarity	NPC307651
0.7717	Intermediate Similarity	NPC136994
0.7717	Intermediate Similarity	NPC88255
0.7705	Intermediate Similarity	NPC246166
0.7692	Intermediate Similarity	NPC190298
0.7679	Intermediate Similarity	NPC156648
0.7672	Intermediate Similarity	NPC474685
0.7672	Intermediate Similarity	NPC217472
0.7661	Intermediate Similarity	NPC473993
0.7658	Intermediate Similarity	NPC269457
0.7656	Intermediate Similarity	NPC98179
0.7656	Intermediate Similarity	NPC253574
0.7647	Intermediate Similarity	NPC89377
0.7647	Intermediate Similarity	NPC286608
0.7647	Intermediate Similarity	NPC169050
0.7647	Intermediate Similarity	NPC96625
0.7632	Intermediate Similarity	NPC183700
0.7632	Intermediate Similarity	NPC476003
0.7632	Intermediate Similarity	NPC474157
0.7632	Intermediate Similarity	NPC323007
0.7627	Intermediate Similarity	NPC65791
0.7623	Intermediate Similarity	NPC138798
0.7615	Intermediate Similarity	NPC42211
0.7611	Intermediate Similarity	NPC206341
0.7611	Intermediate Similarity	NPC182549
0.7611	Intermediate Similarity	NPC114741
0.7611	Intermediate Similarity	NPC469636
0.7611	Intermediate Similarity	NPC281604
0.7603	Intermediate Similarity	NPC475328
0.7597	Intermediate Similarity	NPC33986
0.7593	Intermediate Similarity	NPC210529
0.7593	Intermediate Similarity	NPC154517
0.7593	Intermediate Similarity	NPC175852
0.7593	Intermediate Similarity	NPC160548
0.7581	Intermediate Similarity	NPC61181
0.7565	Intermediate Similarity	NPC470825
0.7563	Intermediate Similarity	NPC309434
0.7563	Intermediate Similarity	NPC275519
0.7559	Intermediate Similarity	NPC239358
0.7559	Intermediate Similarity	NPC233692
0.7544	Intermediate Similarity	NPC474148
0.7544	Intermediate Similarity	NPC276061
0.7541	Intermediate Similarity	NPC325301
0.7541	Intermediate Similarity	NPC327070
0.7523	Intermediate Similarity	NPC118343
0.7523	Intermediate Similarity	NPC80115
0.7521	Intermediate Similarity	NPC306740
0.7521	Intermediate Similarity	NPC469509
0.7521	Intermediate Similarity	NPC476872
0.7521	Intermediate Similarity	NPC470848
0.7521	Intermediate Similarity	NPC470849
0.752	Intermediate Similarity	NPC103533
0.7519	Intermediate Similarity	NPC200154
0.75	Intermediate Similarity	NPC276775
0.75	Intermediate Similarity	NPC92754
0.75	Intermediate Similarity	NPC472248
0.75	Intermediate Similarity	NPC127676
0.75	Intermediate Similarity	NPC470158
0.75	Intermediate Similarity	NPC325499
0.75	Intermediate Similarity	NPC249912
0.75	Intermediate Similarity	NPC128368
0.75	Intermediate Similarity	NPC85830
0.75	Intermediate Similarity	NPC141791
0.75	Intermediate Similarity	NPC475933
0.75	Intermediate Similarity	NPC263386
0.75	Intermediate Similarity	NPC220893
0.748	Intermediate Similarity	NPC224208
0.748	Intermediate Similarity	NPC474275
0.7478	Intermediate Similarity	NPC30563
0.7478	Intermediate Similarity	NPC63345
0.7478	Intermediate Similarity	NPC133308
0.7478	Intermediate Similarity	NPC260818
0.7477	Intermediate Similarity	NPC89886
0.7477	Intermediate Similarity	NPC474365
0.7477	Intermediate Similarity	NPC304638
0.7477	Intermediate Similarity	NPC5472
0.7477	Intermediate Similarity	NPC301943
0.746	Intermediate Similarity	NPC301857
0.7459	Intermediate Similarity	NPC11724
0.7458	Intermediate Similarity	NPC471616
0.7458	Intermediate Similarity	NPC233669
0.7455	Intermediate Similarity	NPC70624
0.7442	Intermediate Similarity	NPC38420
0.7442	Intermediate Similarity	NPC311492
0.7442	Intermediate Similarity	NPC136608
0.7442	Intermediate Similarity	NPC28836
0.744	Intermediate Similarity	NPC476972
0.744	Intermediate Similarity	NPC147192
0.744	Intermediate Similarity	NPC114096
0.744	Intermediate Similarity	NPC476971
0.744	Intermediate Similarity	NPC472706
0.7436	Intermediate Similarity	NPC120217
0.7436	Intermediate Similarity	NPC474641
0.7436	Intermediate Similarity	NPC95381
0.7436	Intermediate Similarity	NPC237366
0.7434	Intermediate Similarity	NPC51174
0.7431	Intermediate Similarity	NPC225060
0.7431	Intermediate Similarity	NPC78701
0.7431	Intermediate Similarity	NPC35448
0.7431	Intermediate Similarity	NPC135951
0.7424	Intermediate Similarity	NPC100913
0.7424	Intermediate Similarity	NPC275592
0.7422	Intermediate Similarity	NPC29734
0.7422	Intermediate Similarity	NPC233860
0.7422	Intermediate Similarity	NPC478255
0.7417	Intermediate Similarity	NPC203124
0.7414	Intermediate Similarity	NPC139946
0.7414	Intermediate Similarity	NPC321852
0.7411	Intermediate Similarity	NPC19136
0.7411	Intermediate Similarity	NPC114594
0.7405	Intermediate Similarity	NPC38099
0.7405	Intermediate Similarity	NPC224543
0.7405	Intermediate Similarity	NPC39549
0.7405	Intermediate Similarity	NPC78746
0.7405	Intermediate Similarity	NPC188380
0.7405	Intermediate Similarity	NPC26954
0.7402	Intermediate Similarity	NPC214246
0.74	Intermediate Similarity	NPC117180
0.74	Intermediate Similarity	NPC89950
0.7398	Intermediate Similarity	NPC132518
0.7398	Intermediate Similarity	NPC477151
0.7398	Intermediate Similarity	NPC223351
0.7398	Intermediate Similarity	NPC52097
0.7398	Intermediate Similarity	NPC472703
0.7395	Intermediate Similarity	NPC281277
0.7395	Intermediate Similarity	NPC470820
0.7391	Intermediate Similarity	NPC174099
0.7391	Intermediate Similarity	NPC79543
0.7387	Intermediate Similarity	NPC94343
0.7385	Intermediate Similarity	NPC204353
0.7385	Intermediate Similarity	NPC326600
0.7385	Intermediate Similarity	NPC62366
0.7385	Intermediate Similarity	NPC50896
0.7381	Intermediate Similarity	NPC173150
0.7381	Intermediate Similarity	NPC288416
0.7381	Intermediate Similarity	NPC45224
0.7381	Intermediate Similarity	NPC471881

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 NPC277788 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	655
0.2-0.3	1383
0.3-0.4	2855
0.4-0.5	2377
0.5-0.6	1332
0.6-0.7	350
0.7-0.8	23
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
0.8364	Intermediate Similarity	NPD969	Suspended
0.8	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD4198	Discontinued
0.7672	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1282	Approved
0.7632	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD9495	Approved
0.7583	Intermediate Similarity	NPD5126	Approved
0.7583	Intermediate Similarity	NPD5125	Phase 3
0.7523	Intermediate Similarity	NPD1238	Approved
0.7521	Intermediate Similarity	NPD2629	Approved
0.7477	Intermediate Similarity	NPD6647	Phase 2
0.7402	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2067	Discontinued
0.7368	Intermediate Similarity	NPD1358	Approved
0.7333	Intermediate Similarity	NPD689	Discontinued
0.7257	Intermediate Similarity	NPD1237	Approved
0.7217	Intermediate Similarity	NPD290	Approved
0.7165	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD2182	Approved
0.7105	Intermediate Similarity	NPD164	Approved
0.7099	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD9697	Approved
0.7018	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2684	Approved
0.7	Intermediate Similarity	NPD5454	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9294	Approved
0.6992	Remote Similarity	NPD7741	Discontinued
0.6983	Remote Similarity	NPD3134	Approved
0.6983	Remote Similarity	NPD6685	Approved
0.6957	Remote Similarity	NPD5909	Discontinued
0.6949	Remote Similarity	NPD9713	Approved
0.6944	Remote Similarity	NPD9256	Approved
0.6944	Remote Similarity	NPD9258	Approved
0.6929	Remote Similarity	NPD7876	Discontinued
0.6917	Remote Similarity	NPD7843	Approved
0.6917	Remote Similarity	NPD6355	Discontinued
0.6912	Remote Similarity	NPD7266	Discontinued
0.6909	Remote Similarity	NPD1202	Approved
0.6903	Remote Similarity	NPD7798	Approved
0.6897	Remote Similarity	NPD5048	Discontinued
0.6885	Remote Similarity	NPD7157	Approved
0.6884	Remote Similarity	NPD4628	Phase 3
0.687	Remote Similarity	NPD5765	Approved
0.6866	Remote Similarity	NPD6653	Approved
0.6864	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD9545	Approved
0.6829	Remote Similarity	NPD9493	Approved
0.6825	Remote Similarity	NPD3496	Discontinued
0.6822	Remote Similarity	NPD2159	Approved
0.6822	Remote Similarity	NPD2627	Approved
0.6822	Remote Similarity	NPD2625	Approved
0.6822	Remote Similarity	NPD2628	Approved
0.6822	Remote Similarity	NPD2626	Approved
0.6822	Remote Similarity	NPD2160	Approved
0.6818	Remote Similarity	NPD3764	Approved
0.6818	Remote Similarity	NPD6798	Discontinued
0.6814	Remote Similarity	NPD5926	Approved
0.6812	Remote Similarity	NPD1652	Phase 2
0.68	Remote Similarity	NPD9716	Approved
0.6788	Remote Similarity	NPD5762	Approved
0.6788	Remote Similarity	NPD5763	Approved
0.678	Remote Similarity	NPD9532	Phase 3
0.6772	Remote Similarity	NPD1091	Approved
0.6772	Remote Similarity	NPD6287	Discontinued
0.6772	Remote Similarity	NPD422	Phase 1
0.6769	Remote Similarity	NPD6085	Phase 2
0.6769	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6233	Phase 2
0.6767	Remote Similarity	NPD4404	Approved
0.6762	Remote Similarity	NPD9491	Approved
0.6757	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD2066	Phase 3
0.6746	Remote Similarity	NPD5305	Approved
0.6746	Remote Similarity	NPD5306	Approved
0.6742	Remote Similarity	NPD7008	Discontinued
0.6739	Remote Similarity	NPD2424	Discontinued
0.6731	Remote Similarity	NPD226	Approved
0.6729	Remote Similarity	NPD9257	Approved
0.6729	Remote Similarity	NPD9259	Approved
0.6724	Remote Similarity	NPD1929	Approved
0.6724	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1930	Approved
0.6721	Remote Similarity	NPD6010	Discontinued
0.672	Remote Similarity	NPD1894	Discontinued
0.6719	Remote Similarity	NPD1877	Discontinued
0.6718	Remote Similarity	NPD5204	Approved
0.6716	Remote Similarity	NPD4060	Phase 1
0.6696	Remote Similarity	NPD2558	Approved
0.6696	Remote Similarity	NPD2549	Approved
0.6696	Remote Similarity	NPD2552	Approved
0.6696	Remote Similarity	NPD2555	Approved
0.6696	Remote Similarity	NPD2553	Approved
0.6696	Remote Similarity	NPD2550	Approved
0.6694	Remote Similarity	NPD5292	Approved
0.6694	Remote Similarity	NPD5291	Approved
0.6694	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6912	Phase 3
0.6693	Remote Similarity	NPD4135	Approved
0.6693	Remote Similarity	NPD4106	Approved
0.6693	Remote Similarity	NPD4136	Approved
0.6692	Remote Similarity	NPD2313	Discontinued
0.6692	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD5239	Approved
0.6667	Remote Similarity	NPD5235	Approved
0.6667	Remote Similarity	NPD5236	Approved
0.6667	Remote Similarity	NPD5240	Approved
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5237	Approved
0.6667	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD4340	Discontinued
0.6667	Remote Similarity	NPD5124	Phase 1
0.6642	Remote Similarity	NPD7033	Discontinued
0.6642	Remote Similarity	NPD4062	Phase 3
0.6641	Remote Similarity	NPD4807	Approved
0.6641	Remote Similarity	NPD4806	Approved
0.6641	Remote Similarity	NPD5647	Approved
0.6641	Remote Similarity	NPD4480	Approved
0.6639	Remote Similarity	NPD5535	Approved
0.6638	Remote Similarity	NPD4189	Approved
0.6638	Remote Similarity	NPD4188	Approved
0.6618	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7095	Approved
0.6615	Remote Similarity	NPD3225	Approved
0.6614	Remote Similarity	NPD4626	Approved
0.6612	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD2201	Approved
0.6606	Remote Similarity	NPD531	Approved
0.6596	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6190	Approved
0.6593	Remote Similarity	NPD4140	Approved
0.6591	Remote Similarity	NPD3663	Approved
0.6591	Remote Similarity	NPD3662	Phase 3
0.6591	Remote Similarity	NPD3661	Approved
0.6591	Remote Similarity	NPD3664	Approved
0.6589	Remote Similarity	NPD9717	Approved
0.6585	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1241	Discontinued
0.6581	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1239	Approved
0.6573	Remote Similarity	NPD5401	Approved
0.6571	Remote Similarity	NPD9250	Approved
0.6569	Remote Similarity	NPD5886	Approved
0.6569	Remote Similarity	NPD2569	Approved
0.6569	Remote Similarity	NPD41	Approved
0.6569	Remote Similarity	NPD2567	Approved
0.6567	Remote Similarity	NPD3268	Approved
0.6565	Remote Similarity	NPD1203	Approved
0.6565	Remote Similarity	NPD987	Approved
0.6565	Remote Similarity	NPD6362	Approved
0.6562	Remote Similarity	NPD3847	Discontinued
0.6557	Remote Similarity	NPD228	Approved
0.6555	Remote Similarity	NPD968	Approved
0.6552	Remote Similarity	NPD1653	Approved
0.6549	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD1693	Approved
0.6547	Remote Similarity	NPD6004	Phase 3
0.6547	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6002	Phase 3
0.6547	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6005	Phase 3
0.6545	Remote Similarity	NPD800	Approved
0.6544	Remote Similarity	NPD230	Phase 1
0.6538	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1357	Approved
0.6535	Remote Similarity	NPD4105	Approved
0.6535	Remote Similarity	NPD4102	Approved
0.6532	Remote Similarity	NPD5951	Approved
0.6525	Remote Similarity	NPD3046	Approved
0.6525	Remote Similarity	NPD3048	Approved
0.6525	Remote Similarity	NPD3047	Approved
0.6522	Remote Similarity	NPD5588	Approved
0.6522	Remote Similarity	NPD4308	Phase 3
0.65	Remote Similarity	NPD5958	Discontinued
0.6496	Remote Similarity	NPD291	Approved
0.6496	Remote Similarity	NPD1932	Approved
0.6493	Remote Similarity	NPD3027	Phase 3
0.6491	Remote Similarity	NPD1989	Approved
0.6489	Remote Similarity	NPD5667	Approved
0.6486	Remote Similarity	NPD1089	Approved
0.6486	Remote Similarity	NPD1090	Approved
0.6486	Remote Similarity	NPD1086	Approved
0.6484	Remote Similarity	NPD6516	Phase 2
0.6484	Remote Similarity	NPD5723	Approved
0.6484	Remote Similarity	NPD5846	Approved
0.6484	Remote Similarity	NPD1778	Approved
0.6483	Remote Similarity	NPD5403	Approved
0.6475	Remote Similarity	NPD6032	Approved
0.6471	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6310	Approved
0.6471	Remote Similarity	NPD6309	Approved
0.6471	Remote Similarity	NPD1613	Approved
0.6471	Remote Similarity	NPD6311	Approved
0.6462	Remote Similarity	NPD1608	Approved
0.6458	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7097	Phase 1
0.6449	Remote Similarity	NPD3971	Phase 1
0.6444	Remote Similarity	NPD1048	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