NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	258.152
LogP:	2.792
LogD:	2.85
LogS:	-3.318
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	4.91
Fsp3:	0.533
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:	-4.484
MDCK Permeability:	2.6860869184019975e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.183

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.878
Plasma Protein Binding (PPB):	63.4504280090332%
Volume Distribution (VD):	0.946
Pgp-substrate:	38.27914047241211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.177
CYP1A2-substrate:	0.747
CYP2C19-inhibitor:	0.294
CYP2C19-substrate:	0.699
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.945
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	12.93
Half-life (T1/2):	0.071

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.285
Carcinogencity:	0.95
Eye Corrosion:	0.108
Eye Irritation:	0.065
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC147921

Natural Product ID:	NPC147921
*Common Name:**	Hydroxylindestenolide
IUPAC Name:	(4aS,8aS,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-3,4a,6,9-tetrahydrobenzo[f][1]benzofuran-2-one
Synonyms:	Hydroxylindestenolide
Standard InCHIKey:	BCKDXTZTXHTKQP-BDHHQKMPSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-9-5-4-6-14(3)8-15(17)12(7-11(9)14)10(2)13(16)18-15/h4,6-7,10-11,17H,1,5,8H2,2-3H3/t10?,11-,14+,15-/m0/s1
SMILES:	C=C1CC=C[C@]2(C)C[C@]3(C(=C[C@@H]12)C(C)C(=O)O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079724
PubChem CID:	46883415
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[26110443]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30415	Lindera aggregate	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17612	Xanthium sibiricum	Species	Asteraceae	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
EC50	1
IC50	3
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	42400.0	nM	PMID[465007]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	37.7	%	PMID[465008]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3900.0	nM	PMID[465008]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	>	35000.0	nM	PMID[465008]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	35000.0	nM	PMID[465008]

☑ 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 NPC147921 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	161
0.1-0.2	1007
0.2-0.3	4712
0.3-0.4	14140
0.4-0.5	10885
0.5-0.6	7471
0.6-0.7	3821
0.7-0.8	494
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8132	Intermediate Similarity	NPC166346
0.809	Intermediate Similarity	NPC477128
0.8068	Intermediate Similarity	NPC250981
0.8022	Intermediate Similarity	NPC233345
0.8022	Intermediate Similarity	NPC186363
0.8	Intermediate Similarity	NPC195424
0.7978	Intermediate Similarity	NPC171722
0.7955	Intermediate Similarity	NPC52628
0.7917	Intermediate Similarity	NPC469657
0.7917	Intermediate Similarity	NPC244456
0.7912	Intermediate Similarity	NPC281942
0.7912	Intermediate Similarity	NPC232426
0.7889	Intermediate Similarity	NPC277771
0.7865	Intermediate Similarity	NPC6979
0.7826	Intermediate Similarity	NPC141831
0.7816	Intermediate Similarity	NPC186276
0.7802	Intermediate Similarity	NPC168131
0.7778	Intermediate Similarity	NPC231599
0.7778	Intermediate Similarity	NPC312561
0.7766	Intermediate Similarity	NPC183012
0.7753	Intermediate Similarity	NPC177932
0.7727	Intermediate Similarity	NPC22611
0.7727	Intermediate Similarity	NPC470948
0.7717	Intermediate Similarity	NPC15059
0.7717	Intermediate Similarity	NPC469372
0.7701	Intermediate Similarity	NPC52861
0.7692	Intermediate Similarity	NPC215831
0.7692	Intermediate Similarity	NPC24816
0.7692	Intermediate Similarity	NPC136879
0.7674	Intermediate Similarity	NPC89128
0.766	Intermediate Similarity	NPC475572
0.766	Intermediate Similarity	NPC250075
0.766	Intermediate Similarity	NPC477130
0.766	Intermediate Similarity	NPC477129
0.7653	Intermediate Similarity	NPC235369
0.764	Intermediate Similarity	NPC295799
0.7634	Intermediate Similarity	NPC289479
0.7634	Intermediate Similarity	NPC65513
0.7614	Intermediate Similarity	NPC89555
0.7609	Intermediate Similarity	NPC73995
0.7609	Intermediate Similarity	NPC173042
0.7609	Intermediate Similarity	NPC218927
0.7609	Intermediate Similarity	NPC206001
0.7604	Intermediate Similarity	NPC70145
0.7604	Intermediate Similarity	NPC476253
0.7604	Intermediate Similarity	NPC76266
0.7604	Intermediate Similarity	NPC91695
0.7582	Intermediate Similarity	NPC475678
0.7558	Intermediate Similarity	NPC179028
0.7558	Intermediate Similarity	NPC267231
0.7558	Intermediate Similarity	NPC169095
0.7553	Intermediate Similarity	NPC472303
0.7551	Intermediate Similarity	NPC63249
0.7529	Intermediate Similarity	NPC41017
0.7527	Intermediate Similarity	NPC469368
0.7526	Intermediate Similarity	NPC216478
0.7526	Intermediate Similarity	NPC23364
0.75	Intermediate Similarity	NPC258532
0.75	Intermediate Similarity	NPC477302
0.7475	Intermediate Similarity	NPC134077
0.7475	Intermediate Similarity	NPC58329
0.7473	Intermediate Similarity	NPC82979
0.7473	Intermediate Similarity	NPC85698
0.7473	Intermediate Similarity	NPC474062
0.7473	Intermediate Similarity	NPC239685
0.7473	Intermediate Similarity	NPC473226
0.7473	Intermediate Similarity	NPC329692
0.7449	Intermediate Similarity	NPC472644
0.7447	Intermediate Similarity	NPC252433
0.7447	Intermediate Similarity	NPC49420
0.7447	Intermediate Similarity	NPC179517
0.7447	Intermediate Similarity	NPC165904
0.7444	Intermediate Similarity	NPC472326
0.7444	Intermediate Similarity	NPC141193
0.7444	Intermediate Similarity	NPC476804
0.7444	Intermediate Similarity	NPC96259
0.7444	Intermediate Similarity	NPC114979
0.7444	Intermediate Similarity	NPC191476
0.7442	Intermediate Similarity	NPC187568
0.7442	Intermediate Similarity	NPC320630
0.7442	Intermediate Similarity	NPC41780
0.7442	Intermediate Similarity	NPC116177
0.7442	Intermediate Similarity	NPC7563
0.7439	Intermediate Similarity	NPC199557
0.7426	Intermediate Similarity	NPC477125
0.7426	Intermediate Similarity	NPC252296
0.7423	Intermediate Similarity	NPC208094
0.7419	Intermediate Similarity	NPC5509
0.7416	Intermediate Similarity	NPC178676
0.7416	Intermediate Similarity	NPC474252
0.7412	Intermediate Similarity	NPC476795
0.7396	Intermediate Similarity	NPC295347
0.7391	Intermediate Similarity	NPC181103
0.7391	Intermediate Similarity	NPC128644
0.7391	Intermediate Similarity	NPC305029
0.7386	Intermediate Similarity	NPC10636
0.7374	Intermediate Similarity	NPC472643
0.7368	Intermediate Similarity	NPC471571
0.7368	Intermediate Similarity	NPC242069
0.7368	Intermediate Similarity	NPC115021
0.7363	Intermediate Similarity	NPC329738
0.7363	Intermediate Similarity	NPC269638
0.7363	Intermediate Similarity	NPC255307
0.7363	Intermediate Similarity	NPC165162
0.7356	Intermediate Similarity	NPC471465
0.7356	Intermediate Similarity	NPC196653
0.7356	Intermediate Similarity	NPC35574
0.7356	Intermediate Similarity	NPC93763
0.7356	Intermediate Similarity	NPC108816
0.7353	Intermediate Similarity	NPC301666
0.7353	Intermediate Similarity	NPC184512
0.7347	Intermediate Similarity	NPC124703
0.7347	Intermediate Similarity	NPC316598
0.7347	Intermediate Similarity	NPC234617
0.734	Intermediate Similarity	NPC152467
0.734	Intermediate Similarity	NPC220454
0.734	Intermediate Similarity	NPC212679
0.734	Intermediate Similarity	NPC477782
0.734	Intermediate Similarity	NPC469595
0.734	Intermediate Similarity	NPC472307
0.734	Intermediate Similarity	NPC214844
0.734	Intermediate Similarity	NPC76286
0.734	Intermediate Similarity	NPC158488
0.7333	Intermediate Similarity	NPC310470
0.7333	Intermediate Similarity	NPC250315
0.7333	Intermediate Similarity	NPC193198
0.7333	Intermediate Similarity	NPC49019
0.7327	Intermediate Similarity	NPC296950
0.7327	Intermediate Similarity	NPC146731
0.7326	Intermediate Similarity	NPC40353
0.7326	Intermediate Similarity	NPC69143
0.732	Intermediate Similarity	NPC112654
0.732	Intermediate Similarity	NPC311166
0.7312	Intermediate Similarity	NPC226863
0.7308	Intermediate Similarity	NPC235014
0.7308	Intermediate Similarity	NPC5103
0.7303	Intermediate Similarity	NPC229584
0.7303	Intermediate Similarity	NPC14203
0.7303	Intermediate Similarity	NPC470241
0.7303	Intermediate Similarity	NPC325031
0.7303	Intermediate Similarity	NPC209318
0.7303	Intermediate Similarity	NPC24417
0.7303	Intermediate Similarity	NPC223330
0.7303	Intermediate Similarity	NPC38642
0.73	Intermediate Similarity	NPC238397
0.73	Intermediate Similarity	NPC31058
0.73	Intermediate Similarity	NPC471363
0.73	Intermediate Similarity	NPC469606
0.73	Intermediate Similarity	NPC273005
0.7294	Intermediate Similarity	NPC241854
0.7294	Intermediate Similarity	NPC476046
0.7294	Intermediate Similarity	NPC301065
0.7294	Intermediate Similarity	NPC213223
0.7294	Intermediate Similarity	NPC251970
0.7292	Intermediate Similarity	NPC474554
0.7292	Intermediate Similarity	NPC53685
0.7292	Intermediate Similarity	NPC474555
0.7292	Intermediate Similarity	NPC167219
0.7292	Intermediate Similarity	NPC471720
0.7283	Intermediate Similarity	NPC475461
0.7283	Intermediate Similarity	NPC305475
0.7283	Intermediate Similarity	NPC198314
0.7283	Intermediate Similarity	NPC9231
0.7273	Intermediate Similarity	NPC470244
0.7273	Intermediate Similarity	NPC477720
0.7273	Intermediate Similarity	NPC98557
0.7273	Intermediate Similarity	NPC167881
0.7273	Intermediate Similarity	NPC17550
0.7273	Intermediate Similarity	NPC475210
0.7273	Intermediate Similarity	NPC469617
0.7273	Intermediate Similarity	NPC470239
0.7263	Intermediate Similarity	NPC477783
0.7263	Intermediate Similarity	NPC303697
0.7263	Intermediate Similarity	NPC324157
0.7262	Intermediate Similarity	NPC160817
0.7262	Intermediate Similarity	NPC129665
0.7255	Intermediate Similarity	NPC469607
0.7255	Intermediate Similarity	NPC472645
0.7253	Intermediate Similarity	NPC159635
0.7245	Intermediate Similarity	NPC53844
0.7245	Intermediate Similarity	NPC474343
0.7245	Intermediate Similarity	NPC98112
0.7245	Intermediate Similarity	NPC257726
0.7245	Intermediate Similarity	NPC204054
0.7245	Intermediate Similarity	NPC254496
0.7241	Intermediate Similarity	NPC122264
0.7241	Intermediate Similarity	NPC137547
0.7241	Intermediate Similarity	NPC107668
0.7241	Intermediate Similarity	NPC97377
0.7238	Intermediate Similarity	NPC304180
0.7238	Intermediate Similarity	NPC179798
0.7234	Intermediate Similarity	NPC50488
0.7234	Intermediate Similarity	NPC118011
0.7234	Intermediate Similarity	NPC284561
0.7234	Intermediate Similarity	NPC174765
0.7234	Intermediate Similarity	NPC251528
0.7234	Intermediate Similarity	NPC474396
0.7234	Intermediate Similarity	NPC36668
0.7228	Intermediate Similarity	NPC36688
0.7228	Intermediate Similarity	NPC475889

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 NPC147921 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1425
0.2-0.3	3803
0.3-0.4	2527
0.4-0.5	778
0.5-0.6	354
0.6-0.7	102
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
0.7753	Intermediate Similarity	NPD1694	Approved
0.7041	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8039	Approved
0.701	Intermediate Similarity	NPD6399	Phase 3
0.6979	Remote Similarity	NPD5785	Approved
0.6907	Remote Similarity	NPD5284	Approved
0.6907	Remote Similarity	NPD5281	Approved
0.6848	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5779	Approved
0.6837	Remote Similarity	NPD5778	Approved
0.6832	Remote Similarity	NPD4225	Approved
0.6804	Remote Similarity	NPD5207	Approved
0.6778	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7154	Phase 3
0.6774	Remote Similarity	NPD5362	Discontinued
0.6737	Remote Similarity	NPD4623	Approved
0.6737	Remote Similarity	NPD4519	Discontinued
0.6735	Remote Similarity	NPD6411	Approved
0.6702	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.663	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7115	Discovery
0.6606	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7639	Approved
0.6602	Remote Similarity	NPD7640	Approved
0.6569	Remote Similarity	NPD7902	Approved
0.6566	Remote Similarity	NPD5693	Phase 1
0.6562	Remote Similarity	NPD5786	Approved
0.6535	Remote Similarity	NPD5695	Phase 3
0.6531	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6101	Approved
0.6505	Remote Similarity	NPD7638	Approved
0.6505	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3573	Approved
0.6489	Remote Similarity	NPD3667	Approved
0.6481	Remote Similarity	NPD6686	Approved
0.6465	Remote Similarity	NPD6698	Approved
0.6465	Remote Similarity	NPD46	Approved
0.6458	Remote Similarity	NPD5363	Approved
0.6458	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4822	Approved
0.6452	Remote Similarity	NPD4820	Approved
0.6452	Remote Similarity	NPD4821	Approved
0.6452	Remote Similarity	NPD4252	Approved
0.6452	Remote Similarity	NPD4819	Approved
0.6436	Remote Similarity	NPD7748	Approved
0.6436	Remote Similarity	NPD6001	Approved
0.6413	Remote Similarity	NPD4268	Approved
0.6413	Remote Similarity	NPD4271	Approved
0.64	Remote Similarity	NPD7637	Suspended
0.64	Remote Similarity	NPD5694	Approved
0.6392	Remote Similarity	NPD7146	Approved
0.6392	Remote Similarity	NPD5690	Phase 2
0.6392	Remote Similarity	NPD4249	Approved
0.6392	Remote Similarity	NPD7521	Approved
0.6392	Remote Similarity	NPD7334	Approved
0.6392	Remote Similarity	NPD6684	Approved
0.6392	Remote Similarity	NPD5330	Approved
0.6392	Remote Similarity	NPD3618	Phase 1
0.6392	Remote Similarity	NPD6409	Approved
0.6392	Remote Similarity	NPD6098	Approved
0.6387	Remote Similarity	NPD8074	Phase 3
0.6383	Remote Similarity	NPD5369	Approved
0.6373	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1695	Approved
0.6364	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4786	Approved
0.6346	Remote Similarity	NPD5696	Approved
0.6327	Remote Similarity	NPD4251	Approved
0.6327	Remote Similarity	NPD4250	Approved
0.6316	Remote Similarity	NPD4221	Approved
0.6316	Remote Similarity	NPD6435	Approved
0.6316	Remote Similarity	NPD4223	Phase 3
0.6311	Remote Similarity	NPD7839	Suspended
0.63	Remote Similarity	NPD5692	Phase 3
0.6289	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6404	Discontinued
0.6277	Remote Similarity	NPD4695	Discontinued
0.6275	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5282	Discontinued
0.6275	Remote Similarity	NPD7900	Approved
0.6263	Remote Similarity	NPD6672	Approved
0.6263	Remote Similarity	NPD6903	Approved
0.6263	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5208	Approved
0.6263	Remote Similarity	NPD5737	Approved
0.6263	Remote Similarity	NPD4518	Approved
0.625	Remote Similarity	NPD5332	Approved
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD5331	Approved
0.625	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD6084	Phase 2
0.6239	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD7983	Approved
0.6238	Remote Similarity	NPD7515	Phase 2
0.6238	Remote Similarity	NPD8035	Phase 2
0.6238	Remote Similarity	NPD6050	Approved
0.6238	Remote Similarity	NPD8034	Phase 2
0.6224	Remote Similarity	NPD4694	Approved
0.6224	Remote Similarity	NPD5280	Approved
0.6224	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6371	Approved
0.6211	Remote Similarity	NPD4790	Discontinued
0.62	Remote Similarity	NPD6673	Approved
0.62	Remote Similarity	NPD6904	Approved
0.62	Remote Similarity	NPD6080	Approved
0.619	Remote Similarity	NPD368	Approved
0.6186	Remote Similarity	NPD3133	Approved
0.6186	Remote Similarity	NPD3666	Approved
0.6186	Remote Similarity	NPD4197	Approved
0.6186	Remote Similarity	NPD3665	Phase 1
0.6182	Remote Similarity	NPD6011	Approved
0.6182	Remote Similarity	NPD6899	Approved
0.6182	Remote Similarity	NPD6881	Approved
0.6161	Remote Similarity	NPD6650	Approved
0.6161	Remote Similarity	NPD6649	Approved
0.6147	Remote Similarity	NPD6402	Approved
0.6147	Remote Similarity	NPD5739	Approved
0.6147	Remote Similarity	NPD7128	Approved
0.6147	Remote Similarity	NPD6675	Approved
0.6147	Remote Similarity	NPD6008	Approved
0.6146	Remote Similarity	NPD5209	Approved
0.6129	Remote Similarity	NPD4756	Discovery
0.6126	Remote Similarity	NPD6373	Approved
0.6126	Remote Similarity	NPD6014	Approved
0.6126	Remote Similarity	NPD6372	Approved
0.6126	Remote Similarity	NPD6013	Approved
0.6126	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6012	Approved
0.6122	Remote Similarity	NPD5329	Approved
0.6106	Remote Similarity	NPD6053	Discontinued
0.6105	Remote Similarity	NPD5368	Approved
0.6092	Remote Similarity	NPD7331	Phase 2
0.6091	Remote Similarity	NPD5701	Approved
0.6091	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8264	Approved
0.6078	Remote Similarity	NPD6079	Approved
0.6071	Remote Similarity	NPD7102	Approved
0.6071	Remote Similarity	NPD7290	Approved
0.6071	Remote Similarity	NPD6883	Approved
0.6064	Remote Similarity	NPD3617	Approved
0.6061	Remote Similarity	NPD4689	Approved
0.6061	Remote Similarity	NPD5279	Phase 3
0.6061	Remote Similarity	NPD4690	Approved
0.6061	Remote Similarity	NPD5205	Approved
0.6061	Remote Similarity	NPD4688	Approved
0.6061	Remote Similarity	NPD4693	Phase 3
0.6061	Remote Similarity	NPD4138	Approved
0.6048	Remote Similarity	NPD7260	Phase 2
0.6047	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD857	Phase 3
0.6042	Remote Similarity	NPD4139	Approved
0.6042	Remote Similarity	NPD4692	Approved
0.604	Remote Similarity	NPD6051	Approved
0.604	Remote Similarity	NPD5328	Approved
0.6036	Remote Similarity	NPD7320	Approved
0.602	Remote Similarity	NPD3668	Phase 3
0.6019	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD5211	Phase 2
0.6019	Remote Similarity	NPD7632	Discontinued
0.6018	Remote Similarity	NPD6617	Approved
0.6018	Remote Similarity	NPD6847	Approved
0.6018	Remote Similarity	NPD8130	Phase 1
0.6018	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD3172	Approved
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD4191	Approved
0.5982	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4687	Approved
0.5965	Remote Similarity	NPD8297	Approved
0.596	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.596	Remote Similarity	NPD1696	Phase 3
0.5946	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6412	Phase 2
0.5926	Remote Similarity	NPD3196	Approved
0.5926	Remote Similarity	NPD4266	Approved
0.5926	Remote Similarity	NPD3194	Approved
0.5926	Remote Similarity	NPD3195	Phase 2
0.5922	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5909	Discontinued
0.5909	Remote Similarity	NPD5141	Approved
0.5905	Remote Similarity	NPD4629	Approved
0.5905	Remote Similarity	NPD5210	Approved
0.5905	Remote Similarity	NPD5654	Approved
0.5902	Remote Similarity	NPD7507	Approved
0.59	Remote Similarity	NPD6422	Discontinued
0.5897	Remote Similarity	NPD6009	Approved
0.5889	Remote Similarity	NPD4137	Phase 3
0.5882	Remote Similarity	NPD5370	Suspended
0.5882	Remote Similarity	NPD4753	Phase 2
0.5877	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD1088	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