NPASS Compound

Structure

NPC61141 OpenBabel07101719252D 30 34 0 0 1 0 0 0 0 0999 V2000 0.0583 5.7469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4417 6.6129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4417 4.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7346 2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9417 4.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0148 2.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0148 0.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9877 -0.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4197 1.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 3.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1488 2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1488 1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7346 1.4417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4417 0.7346 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8808 2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8808 1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 4.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4417 3.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4417 0.7346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4417 4.8808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9417 4.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1564 0.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8244 -0.1893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0474 1.4417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9417 5.7469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9417 5.7469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9417 4.0148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8319 2.7507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8319 1.1327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 10 1 0 0 0 0 5 10 2 0 0 0 0 5 17 1 0 0 0 0 6 11 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 28 1 0 0 0 0 9 29 1 0 0 0 0 9 30 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 4 1 1 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 8 1 6 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 20 2 0 0 0 0 17 25 1 0 0 0 0 18 21 2 0 0 0 0 19 23 2 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 24 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.12
Volume:	395.516
LogP:	2.688
LogD:	2.693
LogS:	-4.218
# Rotatable Bonds:	3
TPSA:	99.75
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	3.527
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.94
MDCK Permeability:	1.5328045265050605e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.102
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	97.06133270263672%
Volume Distribution (VD):	0.505
Pgp-substrate:	3.542259693145752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.731
CYP2C9-inhibitor:	0.321
CYP2C9-substrate:	0.747
CYP2D6-inhibitor:	0.127
CYP2D6-substrate:	0.432
CYP3A4-inhibitor:	0.576
CYP3A4-substrate:	0.83

ADMET: Excretion

Clearance (CL):	9.427
Half-life (T1/2):	0.423

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.061
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.107
Carcinogencity:	0.329
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.783

Download Data

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

Natural Product: NPC61141

Natural Product ID:	NPC61141
*Common Name:**	KHXMONVQVIGKEN-KGLIPLIRSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Steganone
Standard InCHIKey:	KHXMONVQVIGKEN-KGLIPLIRSA-N
Standard InCHI:	InChI=1S/C22H20O8/c1-25-17-5-10-4-13-14(8-28-22(13)24)19(23)12-7-16-15(29-9-30-16)6-11(12)18(10)21(27-3)20(17)26-2/h5-7,13-14H,4,8-9H2,1-3H3/t13-,14+/m1/s1
SMILES:	COc1cc2C[C@H]3C(=O)OC[C@@H]3C(=O)c3c(c2c(c1OC)OC)cc1OCOc1c3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL436025
PubChem CID:	10982518
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

*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
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720541]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6208342]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[8133298]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22886	Steganotaenia araliacea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
ED50	13
Others	7

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	10
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	6.2	ug ml-1	PMID[493736]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[493737]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[493737]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[493737]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[493737]
NPT762	Cell Line	A-431	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[493737]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[493737]
NPT2049	Cell Line	HT	Homo sapiens	ED50	=	0.7	ug ml-1	PMID[493737]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.5	ug ml-1	PMID[493737]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[493737]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[493737]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[493737]
NPT2	Others	Unspecified		ED50	=	68.2	ug ml-1	PMID[493737]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.8	ug ml-1	PMID[493737]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	7.1	ug ml-1	PMID[493737]

☑ 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 NPC61141 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	421
0.1-0.2	1780
0.2-0.3	3703
0.3-0.4	8809
0.4-0.5	10070
0.5-0.6	3768
0.6-0.7	6644
0.7-0.8	6996
0.8-0.85	395
0.85-0.9	94
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9563	High Similarity	NPC178737
0.9548	High Similarity	NPC325122
0.9427	High Similarity	NPC239890
0.9427	High Similarity	NPC209411
0.9295	High Similarity	NPC477380
0.929	High Similarity	NPC348849
0.929	High Similarity	NPC178195
0.9286	High Similarity	NPC220577
0.9286	High Similarity	NPC104353
0.9236	High Similarity	NPC477885
0.9187	High Similarity	NPC475865
0.9182	High Similarity	NPC191352
0.9182	High Similarity	NPC258322
0.913	High Similarity	NPC477884
0.9119	High Similarity	NPC474770
0.9097	High Similarity	NPC303519
0.903	High Similarity	NPC474568
0.903	High Similarity	NPC477881
0.9018	High Similarity	NPC471180
0.9018	High Similarity	NPC42230
0.9012	High Similarity	NPC475953
0.9006	High Similarity	NPC76687
0.8987	High Similarity	NPC254163
0.8981	High Similarity	NPC308555
0.8981	High Similarity	NPC474514
0.8968	High Similarity	NPC85141
0.8944	High Similarity	NPC319749
0.8938	High Similarity	NPC474043
0.8931	High Similarity	NPC301897
0.8909	High Similarity	NPC477883
0.8902	High Similarity	NPC474948
0.8902	High Similarity	NPC79322
0.8896	High Similarity	NPC474647
0.8896	High Similarity	NPC87295
0.8889	High Similarity	NPC18211
0.8889	High Similarity	NPC475000
0.8889	High Similarity	NPC143092
0.8889	High Similarity	NPC280778
0.8869	High Similarity	NPC477882
0.8869	High Similarity	NPC477880
0.8855	High Similarity	NPC471181
0.8834	High Similarity	NPC469518
0.8834	High Similarity	NPC469475
0.8805	High Similarity	NPC57211
0.8805	High Similarity	NPC273578
0.879	High Similarity	NPC316989
0.879	High Similarity	NPC149505
0.8782	High Similarity	NPC327352
0.8782	High Similarity	NPC198129
0.8782	High Similarity	NPC477375
0.8782	High Similarity	NPC252281
0.8774	High Similarity	NPC224687
0.8774	High Similarity	NPC296575
0.8774	High Similarity	NPC193779
0.8774	High Similarity	NPC213482
0.8773	High Similarity	NPC469512
0.8758	High Similarity	NPC151423
0.8758	High Similarity	NPC40237
0.875	High Similarity	NPC234730
0.8743	High Similarity	NPC469506
0.8743	High Similarity	NPC475964
0.8742	High Similarity	NPC68882
0.8742	High Similarity	NPC52623
0.8727	High Similarity	NPC320471
0.8727	High Similarity	NPC118162
0.8727	High Similarity	NPC83049
0.8726	High Similarity	NPC477376
0.8726	High Similarity	NPC477374
0.8726	High Similarity	NPC322426
0.8718	High Similarity	NPC24257
0.8718	High Similarity	NPC153620
0.871	High Similarity	NPC474158
0.8704	High Similarity	NPC125713
0.8688	High Similarity	NPC198461
0.8688	High Similarity	NPC312763
0.8688	High Similarity	NPC478213
0.8679	High Similarity	NPC279061
0.8675	High Similarity	NPC311912
0.8654	High Similarity	NPC321696
0.8654	High Similarity	NPC321958
0.865	High Similarity	NPC78944
0.8645	High Similarity	NPC92693
0.8645	High Similarity	NPC218841
0.8645	High Similarity	NPC474036
0.8642	High Similarity	NPC474990
0.8642	High Similarity	NPC258644
0.8636	High Similarity	NPC176586
0.8636	High Similarity	NPC210354
0.8634	High Similarity	NPC478238
0.8625	High Similarity	NPC148497
0.8625	High Similarity	NPC475116
0.8625	High Similarity	NPC153008
0.8623	High Similarity	NPC88557
0.8616	High Similarity	NPC13985
0.8616	High Similarity	NPC210642
0.8614	High Similarity	NPC474042
0.8614	High Similarity	NPC174734
0.8608	High Similarity	NPC477698
0.8599	High Similarity	NPC104024
0.8599	High Similarity	NPC101755
0.8599	High Similarity	NPC80230
0.8599	High Similarity	NPC65574
0.8599	High Similarity	NPC304687
0.859	High Similarity	NPC27106
0.859	High Similarity	NPC318286
0.859	High Similarity	NPC327651
0.8581	High Similarity	NPC218510
0.8581	High Similarity	NPC474288
0.8581	High Similarity	NPC76415
0.858	High Similarity	NPC261484
0.858	High Similarity	NPC473900
0.858	High Similarity	NPC115123
0.858	High Similarity	NPC239113
0.858	High Similarity	NPC474983
0.8562	High Similarity	NPC473732
0.8554	High Similarity	NPC187923
0.8545	High Similarity	NPC478199
0.8544	High Similarity	NPC262804
0.8544	High Similarity	NPC40654
0.8537	High Similarity	NPC239818
0.8537	High Similarity	NPC218471
0.8528	High Similarity	NPC310206
0.8526	High Similarity	NPC326144
0.8526	High Similarity	NPC177644
0.8526	High Similarity	NPC191158
0.8512	High Similarity	NPC117911
0.8509	High Similarity	NPC16791
0.8509	High Similarity	NPC77237
0.8509	High Similarity	NPC217708
0.8509	High Similarity	NPC53669
0.8509	High Similarity	NPC308739
0.8509	High Similarity	NPC477377
0.8509	High Similarity	NPC24562
0.8509	High Similarity	NPC126405
0.8509	High Similarity	NPC297271
0.85	High Similarity	NPC474975
0.85	High Similarity	NPC164082
0.85	High Similarity	NPC234152
0.85	High Similarity	NPC62354
0.85	High Similarity	NPC32079
0.85	High Similarity	NPC477700
0.8491	Intermediate Similarity	NPC177476
0.8491	Intermediate Similarity	NPC262455
0.8485	Intermediate Similarity	NPC15212
0.848	Intermediate Similarity	NPC196771
0.8476	Intermediate Similarity	NPC113055
0.8471	Intermediate Similarity	NPC72455
0.8471	Intermediate Similarity	NPC470932
0.8471	Intermediate Similarity	NPC184702
0.8466	Intermediate Similarity	NPC155063
0.8462	Intermediate Similarity	NPC297985
0.8457	Intermediate Similarity	NPC244371
0.8457	Intermediate Similarity	NPC475360
0.8447	Intermediate Similarity	NPC272566
0.8447	Intermediate Similarity	NPC475229
0.8447	Intermediate Similarity	NPC56184
0.8447	Intermediate Similarity	NPC477378
0.8447	Intermediate Similarity	NPC477699
0.8443	Intermediate Similarity	NPC475738
0.8442	Intermediate Similarity	NPC470962
0.8439	Intermediate Similarity	NPC170203
0.8438	Intermediate Similarity	NPC474648
0.8438	Intermediate Similarity	NPC473989
0.8434	Intermediate Similarity	NPC108767
0.8434	Intermediate Similarity	NPC469575
0.8428	Intermediate Similarity	NPC470511
0.8428	Intermediate Similarity	NPC474999
0.8428	Intermediate Similarity	NPC304821
0.8424	Intermediate Similarity	NPC131557
0.8424	Intermediate Similarity	NPC139876
0.8424	Intermediate Similarity	NPC43971
0.8424	Intermediate Similarity	NPC19554
0.8424	Intermediate Similarity	NPC74749
0.8421	Intermediate Similarity	NPC290304
0.8421	Intermediate Similarity	NPC66804
0.8421	Intermediate Similarity	NPC236327
0.8418	Intermediate Similarity	NPC474446
0.8415	Intermediate Similarity	NPC207584
0.8415	Intermediate Similarity	NPC19600
0.8415	Intermediate Similarity	NPC163527
0.8415	Intermediate Similarity	NPC115281
0.8415	Intermediate Similarity	NPC167595
0.8415	Intermediate Similarity	NPC82733
0.8415	Intermediate Similarity	NPC181168
0.8415	Intermediate Similarity	NPC19947
0.8415	Intermediate Similarity	NPC76458
0.8412	Intermediate Similarity	NPC38438
0.8405	Intermediate Similarity	NPC117154
0.8405	Intermediate Similarity	NPC284353
0.8405	Intermediate Similarity	NPC79998
0.8405	Intermediate Similarity	NPC476065
0.8405	Intermediate Similarity	NPC238834
0.8402	Intermediate Similarity	NPC211309
0.8402	Intermediate Similarity	NPC41853
0.8395	Intermediate Similarity	NPC35544
0.8395	Intermediate Similarity	NPC292460
0.8395	Intermediate Similarity	NPC104728
0.8395	Intermediate Similarity	NPC477960
0.8395	Intermediate Similarity	NPC477961
0.8395	Intermediate Similarity	NPC477962

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 NPC61141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	961
0.2-0.3	1861
0.3-0.4	2716
0.4-0.5	1887
0.5-0.6	905
0.6-0.7	347
0.7-0.8	111
0.8-0.85	7
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8662	High Similarity	NPD6980	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD4967	Phase 2
0.8354	Intermediate Similarity	NPD4966	Approved
0.8354	Intermediate Similarity	NPD4965	Approved
0.8284	Intermediate Similarity	NPD7473	Discontinued
0.8263	Intermediate Similarity	NPD7199	Phase 2
0.8253	Intermediate Similarity	NPD6234	Discontinued
0.8235	Intermediate Similarity	NPD3818	Discontinued
0.8214	Intermediate Similarity	NPD6232	Discontinued
0.8204	Intermediate Similarity	NPD5494	Approved
0.8171	Intermediate Similarity	NPD37	Approved
0.8166	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD3926	Phase 2
0.8072	Intermediate Similarity	NPD3817	Phase 2
0.8036	Intermediate Similarity	NPD919	Approved
0.8024	Intermediate Similarity	NPD3882	Suspended
0.8012	Intermediate Similarity	NPD7819	Suspended
0.7919	Intermediate Similarity	NPD7228	Approved
0.7901	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7074	Phase 3
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1465	Phase 2
0.7797	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6799	Approved
0.7771	Intermediate Similarity	NPD7054	Approved
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.7744	Intermediate Similarity	NPD2533	Approved
0.7744	Intermediate Similarity	NPD2532	Approved
0.7744	Intermediate Similarity	NPD2534	Approved
0.774	Intermediate Similarity	NPD7240	Approved
0.7738	Intermediate Similarity	NPD1934	Approved
0.7733	Intermediate Similarity	NPD1247	Approved
0.7727	Intermediate Similarity	NPD7472	Approved
0.7725	Intermediate Similarity	NPD6599	Discontinued
0.7692	Intermediate Similarity	NPD2801	Approved
0.7688	Intermediate Similarity	NPD2796	Approved
0.7667	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1243	Approved
0.7651	Intermediate Similarity	NPD920	Approved
0.764	Intermediate Similarity	NPD6559	Discontinued
0.7625	Intermediate Similarity	NPD3748	Approved
0.7598	Intermediate Similarity	NPD7808	Phase 3
0.7588	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6797	Phase 2
0.7566	Intermediate Similarity	NPD5005	Approved
0.7566	Intermediate Similarity	NPD5006	Approved
0.7558	Intermediate Similarity	NPD7075	Discontinued
0.7558	Intermediate Similarity	NPD3749	Approved
0.7547	Intermediate Similarity	NPD1933	Approved
0.7543	Intermediate Similarity	NPD5242	Approved
0.7542	Intermediate Similarity	NPD7251	Discontinued
0.7541	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6801	Discontinued
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7411	Suspended
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4420	Approved
0.7442	Intermediate Similarity	NPD5353	Approved
0.7418	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4380	Phase 2
0.7407	Intermediate Similarity	NPD1510	Phase 2
0.7394	Intermediate Similarity	NPD3750	Approved
0.7389	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1240	Approved
0.7365	Intermediate Similarity	NPD1511	Approved
0.7348	Intermediate Similarity	NPD7685	Pre-registration
0.7341	Intermediate Similarity	NPD5402	Approved
0.7338	Intermediate Similarity	NPD3705	Approved
0.7337	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD8151	Discontinued
0.733	Intermediate Similarity	NPD6959	Discontinued
0.7329	Intermediate Similarity	NPD230	Phase 1
0.7318	Intermediate Similarity	NPD3751	Discontinued
0.7303	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1607	Approved
0.7278	Intermediate Similarity	NPD1512	Approved
0.7278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7267	Intermediate Similarity	NPD6385	Approved
0.7267	Intermediate Similarity	NPD6386	Approved
0.7251	Intermediate Similarity	NPD3226	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.725	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5403	Approved
0.7233	Intermediate Similarity	NPD6832	Phase 2
0.7219	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5401	Approved
0.7212	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7768	Phase 2
0.7195	Intermediate Similarity	NPD2799	Discontinued
0.7191	Intermediate Similarity	NPD5710	Approved
0.7191	Intermediate Similarity	NPD5711	Approved
0.7191	Intermediate Similarity	NPD7229	Phase 3
0.7191	Intermediate Similarity	NPD3787	Discontinued
0.7186	Intermediate Similarity	NPD4628	Phase 3
0.7174	Intermediate Similarity	NPD8313	Approved
0.7174	Intermediate Similarity	NPD8312	Approved
0.716	Intermediate Similarity	NPD943	Approved
0.7152	Intermediate Similarity	NPD2438	Suspended
0.7152	Intermediate Similarity	NPD2935	Discontinued
0.7135	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD447	Suspended
0.7108	Intermediate Similarity	NPD2344	Approved
0.7107	Intermediate Similarity	NPD2798	Approved
0.7104	Intermediate Similarity	NPD5953	Discontinued
0.7091	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1876	Approved
0.7077	Intermediate Similarity	NPD7435	Discontinued
0.7048	Intermediate Similarity	NPD1551	Phase 2
0.7033	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2654	Approved
0.7024	Intermediate Similarity	NPD2800	Approved
0.7022	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD2403	Approved
0.7012	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7028	Phase 2
0.701	Intermediate Similarity	NPD6781	Approved
0.701	Intermediate Similarity	NPD6780	Approved
0.701	Intermediate Similarity	NPD6779	Approved
0.701	Intermediate Similarity	NPD6782	Approved
0.701	Intermediate Similarity	NPD6777	Approved
0.701	Intermediate Similarity	NPD6776	Approved
0.701	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6778	Approved
0.7006	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.7006	Intermediate Similarity	NPD1471	Phase 3
0.7	Intermediate Similarity	NPD6808	Phase 2
0.6994	Remote Similarity	NPD1653	Approved
0.699	Remote Similarity	NPD7680	Approved
0.6987	Remote Similarity	NPD17	Approved
0.6951	Remote Similarity	NPD2979	Phase 3
0.6949	Remote Similarity	NPD5978	Approved
0.6949	Remote Similarity	NPD5977	Approved
0.6941	Remote Similarity	NPD2309	Approved
0.6933	Remote Similarity	NPD3764	Approved
0.6919	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7296	Approved
0.6904	Remote Similarity	NPD7698	Approved
0.6904	Remote Similarity	NPD7697	Approved
0.6904	Remote Similarity	NPD7696	Phase 3
0.6903	Remote Similarity	NPD5536	Phase 2
0.6899	Remote Similarity	NPD1281	Approved
0.6886	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7871	Phase 2
0.6869	Remote Similarity	NPD7870	Phase 2
0.6867	Remote Similarity	NPD6651	Approved
0.6866	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7874	Approved
0.686	Remote Similarity	NPD7390	Discontinued
0.6857	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3972	Approved
0.6855	Remote Similarity	NPD1608	Approved
0.6852	Remote Similarity	NPD3018	Phase 2
0.6851	Remote Similarity	NPD8127	Discontinued
0.6845	Remote Similarity	NPD6099	Approved
0.6845	Remote Similarity	NPD6100	Approved
0.6842	Remote Similarity	NPD6190	Approved
0.6836	Remote Similarity	NPD6280	Approved
0.6836	Remote Similarity	NPD6279	Approved
0.6832	Remote Similarity	NPD3266	Approved
0.6832	Remote Similarity	NPD3267	Approved
0.6816	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7930	Approved
0.6811	Remote Similarity	NPD7286	Phase 2
0.6807	Remote Similarity	NPD6355	Discontinued
0.6798	Remote Similarity	NPD8455	Phase 2
0.6789	Remote Similarity	NPD8150	Discontinued
0.6784	Remote Similarity	NPD8320	Phase 1
0.6784	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7003	Approved
0.6784	Remote Similarity	NPD4110	Phase 3
0.6784	Remote Similarity	NPD8319	Approved
0.6782	Remote Similarity	NPD6273	Approved
0.678	Remote Similarity	NPD6873	Phase 2
0.677	Remote Similarity	NPD1283	Approved
0.6768	Remote Similarity	NPD3027	Phase 3
0.6766	Remote Similarity	NPD7701	Phase 2
0.676	Remote Similarity	NPD4288	Approved
0.6755	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6535	Approved
0.6753	Remote Similarity	NPD6534	Approved
0.6753	Remote Similarity	NPD5283	Phase 1
0.675	Remote Similarity	NPD2981	Phase 2
0.6749	Remote Similarity	NPD7801	Approved
0.6749	Remote Similarity	NPD7783	Phase 2

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