NPASS Compound

Structure

CID53158 OpenBabel06191715392D 21 23 0 0 1 0 0 0 0 0999 V2000 1.8370 -3.7992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9297 0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9149 -1.3371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9002 -1.0288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2560 -3.1923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6923 -2.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5068 -2.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2758 -0.7773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2371 -2.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0342 -0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9337 -1.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6978 -2.1115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4769 -1.5461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2910 -1.1979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3232 -0.9463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9999 -0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2946 -0.9705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6105 -2.4767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5997 0.7852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9526 -1.7236 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 1 9 2 0 0 0 0 2 10 2 0 0 0 0 3 11 1 0 0 0 0 4 6 1 0 0 0 0 4 10 1 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 11 18 2 0 0 0 0 12 6 1 1 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 1 0 0 0 14 10 1 1 0 0 0 14 15 1 0 0 0 0 15 21 1 6 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.15
Volume:	301.534
LogP:	1.615
LogD:	2.332
LogS:	-3.578
# Rotatable Bonds:	2
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	4.765
Fsp3:	0.647
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:	-4.824
MDCK Permeability:	1.2578378118632827e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	63.66545486450195%
Volume Distribution (VD):	0.678
Pgp-substrate:	39.5018424987793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.342
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.681
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.281
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.766
CYP3A4-inhibitor:	0.204
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	4.991
Half-life (T1/2):	0.636

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.654
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.119
Skin Sensitization:	0.044
Carcinogencity:	0.113
Eye Corrosion:	0.006
Eye Irritation:	0.087
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC53158

Natural Product ID:	NPC53158
*Common Name:**	Lappalone
IUPAC Name:	(3R,3aR,6aR,9aR,9bR)-3-hydroxy-6,9-dimethylidene-3-(2-oxopropyl)-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
Synonyms:	Lappalone
Standard InCHIKey:	JPMPVNCPOBTSBR-CEEVZKBLSA-N
Standard InCHI:	InChI=1S/C17H22O4/c1-9-5-7-13-15(14-10(2)4-6-12(9)14)21-16(19)17(13,20)8-11(3)18/h12-15,20H,1-2,4-8H2,3H3/t12-,13+,14-,15-,17+/m0/s1
SMILES:	CC(=O)C[C@]1(O)C(=O)O[C@H]2[C@H]1CCC(=C)[C@H]1[C@@H]2C(=C)CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518009
PubChem CID:	10979139
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[18409040]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[18579374]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25068579]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[8541643]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25825	Saussurea lappa	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
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT377	Cell Line	OVCAR-3	Homo sapiens	CD50	>	100.0	ug ml-1	PMID[567352]
NPT165	Cell Line	HeLa	Homo sapiens	CD50	>	100.0	ug ml-1	PMID[567352]
NPT65	Cell Line	HepG2	Homo sapiens	CD50	>	100.0	ug ml-1	PMID[567352]

☑ 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 NPC53158 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	250
0.1-0.2	1990
0.2-0.3	7685
0.3-0.4	15410
0.4-0.5	8828
0.5-0.6	6394
0.6-0.7	1838
0.7-0.8	281
0.8-0.85	18
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC475788
0.8571	High Similarity	NPC51507
0.8478	Intermediate Similarity	NPC475900
0.8387	Intermediate Similarity	NPC476009
0.8352	Intermediate Similarity	NPC469627
0.8298	Intermediate Similarity	NPC474313
0.8242	Intermediate Similarity	NPC65359
0.8132	Intermediate Similarity	NPC12872
0.8132	Intermediate Similarity	NPC168679
0.8111	Intermediate Similarity	NPC201658
0.8111	Intermediate Similarity	NPC190753
0.8085	Intermediate Similarity	NPC163228
0.8065	Intermediate Similarity	NPC473234
0.8065	Intermediate Similarity	NPC473263
0.8065	Intermediate Similarity	NPC60386
0.8065	Intermediate Similarity	NPC308656
0.8065	Intermediate Similarity	NPC473273
0.8061	Intermediate Similarity	NPC475873
0.8041	Intermediate Similarity	NPC474742
0.8	Intermediate Similarity	NPC475491
0.8	Intermediate Similarity	NPC238593
0.8	Intermediate Similarity	NPC236692
0.8	Intermediate Similarity	NPC309757
0.8	Intermediate Similarity	NPC469626
0.7959	Intermediate Similarity	NPC474747
0.7917	Intermediate Similarity	NPC471150
0.7912	Intermediate Similarity	NPC118601
0.7879	Intermediate Similarity	NPC475945
0.7879	Intermediate Similarity	NPC475871
0.7872	Intermediate Similarity	NPC153590
0.7857	Intermediate Similarity	NPC110443
0.7857	Intermediate Similarity	NPC185141
0.7857	Intermediate Similarity	NPC133907
0.7857	Intermediate Similarity	NPC46998
0.7857	Intermediate Similarity	NPC128733
0.7826	Intermediate Similarity	NPC178875
0.7812	Intermediate Similarity	NPC142529
0.7812	Intermediate Similarity	NPC91771
0.7812	Intermediate Similarity	NPC76862
0.7812	Intermediate Similarity	NPC39859
0.7812	Intermediate Similarity	NPC158416
0.7812	Intermediate Similarity	NPC470883
0.7805	Intermediate Similarity	NPC5714
0.78	Intermediate Similarity	NPC474741
0.7789	Intermediate Similarity	NPC473331
0.7766	Intermediate Similarity	NPC184063
0.7755	Intermediate Similarity	NPC186861
0.7745	Intermediate Similarity	NPC117604
0.7742	Intermediate Similarity	NPC173926
0.7742	Intermediate Similarity	NPC474951
0.7732	Intermediate Similarity	NPC213947
0.7732	Intermediate Similarity	NPC170143
0.7732	Intermediate Similarity	NPC108475
0.7732	Intermediate Similarity	NPC311904
0.7727	Intermediate Similarity	NPC258965
0.7727	Intermediate Similarity	NPC156658
0.7723	Intermediate Similarity	NPC44004
0.7684	Intermediate Similarity	NPC200237
0.7684	Intermediate Similarity	NPC469692
0.7684	Intermediate Similarity	NPC469645
0.7667	Intermediate Similarity	NPC54468
0.7667	Intermediate Similarity	NPC111409
0.7667	Intermediate Similarity	NPC128246
0.7667	Intermediate Similarity	NPC245665
0.766	Intermediate Similarity	NPC19087
0.7604	Intermediate Similarity	NPC121825
0.7604	Intermediate Similarity	NPC190294
0.7586	Intermediate Similarity	NPC208223
0.7579	Intermediate Similarity	NPC191339
0.7579	Intermediate Similarity	NPC286341
0.7576	Intermediate Similarity	NPC471381
0.757	Intermediate Similarity	NPC54739
0.7558	Intermediate Similarity	NPC179922
0.7553	Intermediate Similarity	NPC38392
0.7528	Intermediate Similarity	NPC293418
0.7528	Intermediate Similarity	NPC290508
0.7528	Intermediate Similarity	NPC73052
0.7528	Intermediate Similarity	NPC6823
0.7527	Intermediate Similarity	NPC186148
0.7527	Intermediate Similarity	NPC179659
0.7526	Intermediate Similarity	NPC476053
0.7526	Intermediate Similarity	NPC472873
0.75	Intermediate Similarity	NPC304624
0.75	Intermediate Similarity	NPC171759
0.75	Intermediate Similarity	NPC474053
0.75	Intermediate Similarity	NPC47880
0.75	Intermediate Similarity	NPC67296
0.7476	Intermediate Similarity	NPC26617
0.7451	Intermediate Similarity	NPC203659
0.7451	Intermediate Similarity	NPC100487
0.7449	Intermediate Similarity	NPC474297
0.7449	Intermediate Similarity	NPC31645
0.7447	Intermediate Similarity	NPC177629
0.7447	Intermediate Similarity	NPC217983
0.7447	Intermediate Similarity	NPC58219
0.7447	Intermediate Similarity	NPC79549
0.7447	Intermediate Similarity	NPC207114
0.7444	Intermediate Similarity	NPC126248
0.7426	Intermediate Similarity	NPC225353
0.7426	Intermediate Similarity	NPC149371
0.7423	Intermediate Similarity	NPC469632
0.7419	Intermediate Similarity	NPC304558
0.7416	Intermediate Similarity	NPC19841
0.7412	Intermediate Similarity	NPC470243
0.7404	Intermediate Similarity	NPC255082
0.7396	Intermediate Similarity	NPC111114
0.7396	Intermediate Similarity	NPC261607
0.7396	Intermediate Similarity	NPC300312
0.7391	Intermediate Similarity	NPC156485
0.7391	Intermediate Similarity	NPC165287
0.7379	Intermediate Similarity	NPC474101
0.7379	Intermediate Similarity	NPC54737
0.7379	Intermediate Similarity	NPC190867
0.7374	Intermediate Similarity	NPC169205
0.7374	Intermediate Similarity	NPC261372
0.7374	Intermediate Similarity	NPC58267
0.7374	Intermediate Similarity	NPC323421
0.7374	Intermediate Similarity	NPC263674
0.7374	Intermediate Similarity	NPC236580
0.7374	Intermediate Similarity	NPC304445
0.7374	Intermediate Similarity	NPC328562
0.7368	Intermediate Similarity	NPC52198
0.7368	Intermediate Similarity	NPC92974
0.7368	Intermediate Similarity	NPC117405
0.7368	Intermediate Similarity	NPC215556
0.7356	Intermediate Similarity	NPC471491
0.7353	Intermediate Similarity	NPC110989
0.7353	Intermediate Similarity	NPC473148
0.7347	Intermediate Similarity	NPC322188
0.7347	Intermediate Similarity	NPC472469
0.7347	Intermediate Similarity	NPC275960
0.7347	Intermediate Similarity	NPC193645
0.7347	Intermediate Similarity	NPC48803
0.7347	Intermediate Similarity	NPC90121
0.734	Intermediate Similarity	NPC197333
0.7339	Intermediate Similarity	NPC471146
0.7339	Intermediate Similarity	NPC471145
0.7333	Intermediate Similarity	NPC103634
0.7327	Intermediate Similarity	NPC472753
0.7327	Intermediate Similarity	NPC477950
0.7327	Intermediate Similarity	NPC201718
0.732	Intermediate Similarity	NPC135776
0.7312	Intermediate Similarity	NPC284534
0.7312	Intermediate Similarity	NPC204105
0.7312	Intermediate Similarity	NPC475206
0.7312	Intermediate Similarity	NPC329749
0.7312	Intermediate Similarity	NPC300082
0.7303	Intermediate Similarity	NPC11796
0.7303	Intermediate Similarity	NPC218817
0.73	Intermediate Similarity	NPC45125
0.73	Intermediate Similarity	NPC141191
0.7292	Intermediate Similarity	NPC216284
0.7292	Intermediate Similarity	NPC297474
0.7292	Intermediate Similarity	NPC54065
0.7292	Intermediate Similarity	NPC246173
0.7282	Intermediate Similarity	NPC13385
0.7282	Intermediate Similarity	NPC469629
0.7273	Intermediate Similarity	NPC185553
0.7263	Intermediate Similarity	NPC254572
0.7263	Intermediate Similarity	NPC471047
0.7263	Intermediate Similarity	NPC476708
0.7263	Intermediate Similarity	NPC472008
0.7263	Intermediate Similarity	NPC250687
0.7263	Intermediate Similarity	NPC229407
0.7263	Intermediate Similarity	NPC469628
0.7263	Intermediate Similarity	NPC475906
0.7263	Intermediate Similarity	NPC469653
0.7263	Intermediate Similarity	NPC48824
0.7263	Intermediate Similarity	NPC469631
0.7255	Intermediate Similarity	NPC472754
0.7255	Intermediate Similarity	NPC80144
0.7253	Intermediate Similarity	NPC255580
0.7253	Intermediate Similarity	NPC39411
0.7245	Intermediate Similarity	NPC167219
0.7245	Intermediate Similarity	NPC289004
0.7241	Intermediate Similarity	NPC143979
0.7241	Intermediate Similarity	NPC320537
0.7241	Intermediate Similarity	NPC215030
0.7238	Intermediate Similarity	NPC68248
0.7234	Intermediate Similarity	NPC476015
0.7234	Intermediate Similarity	NPC475019
0.7234	Intermediate Similarity	NPC104961
0.7234	Intermediate Similarity	NPC474949
0.7234	Intermediate Similarity	NPC470242
0.7234	Intermediate Similarity	NPC187661
0.7234	Intermediate Similarity	NPC70555
0.7234	Intermediate Similarity	NPC474762
0.7234	Intermediate Similarity	NPC70422
0.7216	Intermediate Similarity	NPC184463
0.7216	Intermediate Similarity	NPC155215
0.7216	Intermediate Similarity	NPC293001
0.7216	Intermediate Similarity	NPC208886
0.7216	Intermediate Similarity	NPC12172
0.7216	Intermediate Similarity	NPC123177
0.7216	Intermediate Similarity	NPC35959
0.7216	Intermediate Similarity	NPC57304
0.7216	Intermediate Similarity	NPC29821
0.7216	Intermediate Similarity	NPC329952
0.7216	Intermediate Similarity	NPC475925
0.7216	Intermediate Similarity	NPC70595

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 NPC53158 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	2815
0.2-0.3	3798
0.3-0.4	1472
0.4-0.5	500
0.5-0.6	221
0.6-0.7	49
0.7-0.8	2
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
0.7476	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5369	Approved
0.7234	Intermediate Similarity	NPD5786	Approved
0.6989	Remote Similarity	NPD6435	Approved
0.69	Remote Similarity	NPD5282	Discontinued
0.6809	Remote Similarity	NPD4269	Approved
0.6809	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD5368	Approved
0.67	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD6371	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6632	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5363	Approved
0.6596	Remote Similarity	NPD4252	Approved
0.6562	Remote Similarity	NPD5362	Discontinued
0.6545	Remote Similarity	NPD6373	Approved
0.6545	Remote Similarity	NPD6372	Approved
0.6535	Remote Similarity	NPD6411	Approved
0.6505	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD1695	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6455	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7320	Approved
0.6436	Remote Similarity	NPD5785	Approved
0.6429	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.6422	Remote Similarity	NPD6675	Approved
0.6422	Remote Similarity	NPD6402	Approved
0.6422	Remote Similarity	NPD5739	Approved
0.6422	Remote Similarity	NPD7128	Approved
0.641	Remote Similarity	NPD6319	Approved
0.6392	Remote Similarity	NPD7154	Phase 3
0.6381	Remote Similarity	NPD6083	Phase 2
0.6381	Remote Similarity	NPD6084	Phase 2
0.6373	Remote Similarity	NPD8034	Phase 2
0.6373	Remote Similarity	NPD8035	Phase 2
0.6372	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6333	Remote Similarity	NPD7492	Approved
0.633	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4225	Approved
0.6306	Remote Similarity	NPD6899	Approved
0.6306	Remote Similarity	NPD6881	Approved
0.6293	Remote Similarity	NPD7115	Discovery
0.6281	Remote Similarity	NPD6616	Approved
0.6271	Remote Similarity	NPD6054	Approved
0.6271	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4819	Approved
0.625	Remote Similarity	NPD6013	Approved
0.623	Remote Similarity	NPD7078	Approved
0.623	Remote Similarity	NPD8293	Discontinued
0.6218	Remote Similarity	NPD6015	Approved
0.6218	Remote Similarity	NPD6016	Approved
0.6211	Remote Similarity	NPD4802	Phase 2
0.6211	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4238	Approved
0.6204	Remote Similarity	NPD1700	Approved
0.62	Remote Similarity	NPD4249	Approved
0.6195	Remote Similarity	NPD6883	Approved
0.6195	Remote Similarity	NPD7290	Approved
0.6195	Remote Similarity	NPD7102	Approved
0.6179	Remote Similarity	NPD7736	Approved
0.6174	Remote Similarity	NPD4632	Approved
0.6167	Remote Similarity	NPD5988	Approved
0.6167	Remote Similarity	NPD6370	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.614	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6617	Approved
0.614	Remote Similarity	NPD6869	Approved
0.6139	Remote Similarity	NPD4250	Approved
0.6139	Remote Similarity	NPD4251	Approved
0.6132	Remote Similarity	NPD4697	Phase 3
0.6126	Remote Similarity	NPD6008	Approved
0.6117	Remote Similarity	NPD6698	Approved
0.6117	Remote Similarity	NPD46	Approved
0.61	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD6053	Discontinued
0.6078	Remote Similarity	NPD6672	Approved
0.6078	Remote Similarity	NPD5737	Approved
0.6075	Remote Similarity	NPD4755	Approved
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.6053	Remote Similarity	NPD4634	Approved
0.6042	Remote Similarity	NPD4268	Approved
0.6042	Remote Similarity	NPD4271	Approved
0.602	Remote Similarity	NPD4790	Discontinued
0.6019	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7839	Suspended
0.5963	Remote Similarity	NPD4700	Approved
0.5963	Remote Similarity	NPD5286	Approved
0.5963	Remote Similarity	NPD4696	Approved
0.5963	Remote Similarity	NPD5285	Approved
0.596	Remote Similarity	NPD3667	Approved
0.5955	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8516	Approved
0.595	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8515	Approved
0.595	Remote Similarity	NPD8517	Approved
0.595	Remote Similarity	NPD8513	Phase 3
0.5941	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD229	Approved
0.5932	Remote Similarity	NPD6274	Approved
0.593	Remote Similarity	NPD3198	Approved
0.5922	Remote Similarity	NPD6903	Approved
0.5905	Remote Similarity	NPD7637	Suspended
0.5888	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4629	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5882	Remote Similarity	NPD6409	Approved
0.5882	Remote Similarity	NPD5279	Phase 3
0.5882	Remote Similarity	NPD6009	Approved
0.5882	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7334	Approved
0.5882	Remote Similarity	NPD7521	Approved
0.5882	Remote Similarity	NPD5330	Approved
0.5882	Remote Similarity	NPD7146	Approved
0.5882	Remote Similarity	NPD6098	Approved
0.5882	Remote Similarity	NPD6684	Approved
0.5865	Remote Similarity	NPD6904	Approved
0.5865	Remote Similarity	NPD5370	Suspended
0.5865	Remote Similarity	NPD6673	Approved
0.5865	Remote Similarity	NPD6080	Approved
0.5862	Remote Similarity	NPD2204	Approved
0.5856	Remote Similarity	NPD5226	Approved
0.5856	Remote Similarity	NPD5211	Phase 2
0.5856	Remote Similarity	NPD4633	Approved
0.5856	Remote Similarity	NPD5224	Approved
0.5856	Remote Similarity	NPD5225	Approved
0.5854	Remote Similarity	NPD8328	Phase 3
0.5843	Remote Similarity	NPD7909	Approved
0.5843	Remote Similarity	NPD3197	Phase 1
0.5842	Remote Similarity	NPD4786	Approved
0.5833	Remote Similarity	NPD5222	Approved
0.5833	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5221	Approved
0.582	Remote Similarity	NPD8266	Approved
0.582	Remote Similarity	NPD8269	Approved
0.582	Remote Similarity	NPD5983	Phase 2
0.582	Remote Similarity	NPD8268	Approved
0.582	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.582	Remote Similarity	NPD6921	Approved
0.582	Remote Similarity	NPD8267	Approved
0.581	Remote Similarity	NPD5207	Approved
0.581	Remote Similarity	NPD5692	Phase 3
0.5804	Remote Similarity	NPD5175	Approved
0.5804	Remote Similarity	NPD5174	Approved
0.5794	Remote Similarity	NPD6033	Approved
0.5789	Remote Similarity	NPD6412	Phase 2
0.5785	Remote Similarity	NPD7100	Approved
0.5785	Remote Similarity	NPD7101	Approved
0.578	Remote Similarity	NPD7902	Approved
0.578	Remote Similarity	NPD5173	Approved
0.5778	Remote Similarity	NPD7341	Phase 2
0.5772	Remote Similarity	NPD8080	Discontinued
0.5769	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5223	Approved
0.5755	Remote Similarity	NPD5693	Phase 1
0.5755	Remote Similarity	NPD5694	Approved
0.5755	Remote Similarity	NPD6050	Approved
0.5755	Remote Similarity	NPD5281	Approved
0.5755	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5284	Approved
0.5752	Remote Similarity	NPD5141	Approved
0.575	Remote Similarity	NPD6317	Approved
0.5748	Remote Similarity	NPD7319	Approved
0.5743	Remote Similarity	NPD4788	Approved
0.5729	Remote Similarity	NPD3702	Approved
0.5728	Remote Similarity	NPD3618	Phase 1
0.5728	Remote Similarity	NPD6422	Discontinued
0.5728	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD5328	Approved
0.5714	Remote Similarity	NPD7331	Phase 2
0.5714	Remote Similarity	NPD3728	Approved
0.5714	Remote Similarity	NPD3730	Approved
0.5702	Remote Similarity	NPD6335	Approved
0.5702	Remote Similarity	NPD6314	Approved
0.5702	Remote Similarity	NPD4767	Approved
0.5702	Remote Similarity	NPD4768	Approved
0.5702	Remote Similarity	NPD6313	Approved
0.5691	Remote Similarity	NPD6909	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