NPASS Compound

Structure

NPC184063 OpenBabel07101718282D 26 28 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 2.2410 1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1363 6.2618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5485 5.4527 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 2.4385 4.3537 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 1.2946 0.9705 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 -2.9002 1.0288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5068 2.5457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5249 3.9470 0.0000 C 0 0 0 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 0.4769 1.5461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3232 0.9463 0.0000 C 0 0 2 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 2.5430 5.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 0.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7159 4.5347 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 3.4565 5.7550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 2.9524 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 2 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 19 1 0 0 0 0 12 7 1 1 0 0 0 12 16 1 0 0 0 0 13 21 1 1 0 0 0 14 17 1 0 0 0 0 14 25 1 6 0 0 0 15 22 2 0 0 0 0 15 25 1 0 0 0 0 16 10 1 1 0 0 0 16 18 1 0 0 0 0 17 11 1 1 0 0 0 17 18 1 0 0 0 0 18 26 1 6 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	368.366
LogP:	0.86
LogD:	1.697
LogS:	-2.585
# Rotatable Bonds:	4
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	4.885
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.861
MDCK Permeability:	0.00014845126133877784
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.42
20% Bioavailability (F20%):	0.289
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	63.34210205078125%
Volume Distribution (VD):	0.473
Pgp-substrate:	44.541316986083984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.22
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.117
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	9.541
Half-life (T1/2):	0.676

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.955
Drug-inuced Liver Injury (DILI):	0.664
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.774
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.116
Carcinogencity:	0.122
Eye Corrosion:	0.044
Eye Irritation:	0.026
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: NPC184063

Natural Product ID:	NPC184063
*Common Name:**	8-O-(3-Hydroxy-3-Methylbutyryl)Desacylcynaropicrin
IUPAC Name:	[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 3-hydroxy-3-methylbutanoate
Synonyms:
Standard InCHIKey:	FSKLYZXJGAAEQB-MGLAFYJRSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-9-6-14(25-15(22)8-20(4,5)24)17-11(3)19(23)26-18(17)16-10(2)13(21)7-12(9)16/h12-14,16-18,21,24H,1-3,6-8H2,4-5H3/t12-,13-,14-,16-,17+,18+/m0/s1
SMILES:	O=C(CC(O)(C)C)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)C(=C)[C@H](C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457308
PubChem CID:	24862586
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
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[18314958]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2291	Saussurea pulchella	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	uM	PMID[510952]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	12.42	uM	PMID[510952]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	6.48	uM	PMID[510952]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	14.23	uM	PMID[510952]

☑ 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 NPC184063 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	247
0.1-0.2	1746
0.2-0.3	6090
0.3-0.4	13981
0.4-0.5	10467
0.5-0.6	6749
0.6-0.7	2737
0.7-0.8	520
0.8-0.85	75
0.85-0.9	44
0.9-0.95	36
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC19087
0.9765	High Similarity	NPC38392
0.9647	High Similarity	NPC217983
0.9647	High Similarity	NPC207114
0.9444	High Similarity	NPC474313
0.9412	High Similarity	NPC187661
0.931	High Similarity	NPC215556
0.9205	High Similarity	NPC297474
0.9205	High Similarity	NPC216284
0.9205	High Similarity	NPC54065
0.9195	High Similarity	NPC79549
0.9186	High Similarity	NPC304558
0.9176	High Similarity	NPC224386
0.9176	High Similarity	NPC194859
0.9121	High Similarity	NPC142529
0.9121	High Similarity	NPC91771
0.9101	High Similarity	NPC293001
0.9101	High Similarity	NPC63193
0.9101	High Similarity	NPC133888
0.9101	High Similarity	NPC57304
0.9101	High Similarity	NPC171360
0.9101	High Similarity	NPC35959
0.9101	High Similarity	NPC475925
0.9101	High Similarity	NPC29821
0.9091	High Similarity	NPC155935
0.9059	High Similarity	NPC128246
0.9022	High Similarity	NPC311904
0.9011	High Similarity	NPC476053
0.9011	High Similarity	NPC472873
0.9	High Similarity	NPC473234
0.9	High Similarity	NPC60386
0.9	High Similarity	NPC258216
0.9	High Similarity	NPC473273
0.9	High Similarity	NPC475788
0.9	High Similarity	NPC473263
0.9	High Similarity	NPC308656
0.8989	High Similarity	NPC35809
0.8941	High Similarity	NPC246076
0.8901	High Similarity	NPC473331
0.8901	High Similarity	NPC198853
0.8889	High Similarity	NPC155215
0.8864	High Similarity	NPC118601
0.8851	High Similarity	NPC284534
0.8851	High Similarity	NPC300082
0.8851	High Similarity	NPC204105
0.8824	High Similarity	NPC126248
0.8817	High Similarity	NPC471150
0.8804	High Similarity	NPC213698
0.8804	High Similarity	NPC170120
0.8804	High Similarity	NPC163228
0.8791	High Similarity	NPC153590
0.8791	High Similarity	NPC200237
0.8764	High Similarity	NPC178875
0.875	High Similarity	NPC56593
0.8737	High Similarity	NPC171759
0.871	High Similarity	NPC24956
0.871	High Similarity	NPC18019
0.8696	High Similarity	NPC470010
0.8696	High Similarity	NPC127019
0.8696	High Similarity	NPC262133
0.8696	High Similarity	NPC323008
0.8696	High Similarity	NPC470013
0.8681	High Similarity	NPC133698
0.8681	High Similarity	NPC191339
0.8681	High Similarity	NPC286341
0.8681	High Similarity	NPC131209
0.8667	High Similarity	NPC168679
0.8667	High Similarity	NPC12872
0.8667	High Similarity	NPC472872
0.8652	High Similarity	NPC201658
0.8652	High Similarity	NPC24728
0.8621	High Similarity	NPC111409
0.8621	High Similarity	NPC245665
0.8617	High Similarity	NPC108475
0.8617	High Similarity	NPC170143
0.8617	High Similarity	NPC161493
0.8617	High Similarity	NPC213947
0.8602	High Similarity	NPC304886
0.8602	High Similarity	NPC52044
0.8602	High Similarity	NPC67584
0.8571	High Similarity	NPC44004
0.8556	High Similarity	NPC471149
0.8542	High Similarity	NPC150923
0.8539	High Similarity	NPC64153
0.8539	High Similarity	NPC470242
0.8539	High Similarity	NPC236692
0.8539	High Similarity	NPC309757
0.8511	High Similarity	NPC476009
0.8511	High Similarity	NPC213078
0.8495	Intermediate Similarity	NPC477131
0.8462	Intermediate Similarity	NPC283409
0.8438	Intermediate Similarity	NPC186861
0.8438	Intermediate Similarity	NPC471381
0.8421	Intermediate Similarity	NPC181151
0.8404	Intermediate Similarity	NPC475900
0.8352	Intermediate Similarity	NPC91248
0.8333	Intermediate Similarity	NPC49833
0.8333	Intermediate Similarity	NPC249171
0.8333	Intermediate Similarity	NPC221615
0.8333	Intermediate Similarity	NPC162071
0.8333	Intermediate Similarity	NPC45125
0.8333	Intermediate Similarity	NPC67493
0.8333	Intermediate Similarity	NPC238593
0.8316	Intermediate Similarity	NPC126156
0.8276	Intermediate Similarity	NPC156658
0.8276	Intermediate Similarity	NPC258965
0.8265	Intermediate Similarity	NPC80144
0.8265	Intermediate Similarity	NPC86077
0.8242	Intermediate Similarity	NPC190753
0.8242	Intermediate Similarity	NPC186148
0.8242	Intermediate Similarity	NPC270270
0.8229	Intermediate Similarity	NPC236580
0.8229	Intermediate Similarity	NPC304445
0.8222	Intermediate Similarity	NPC235792
0.82	Intermediate Similarity	NPC54737
0.8191	Intermediate Similarity	NPC472874
0.8191	Intermediate Similarity	NPC135776
0.8182	Intermediate Similarity	NPC473148
0.8172	Intermediate Similarity	NPC206614
0.8172	Intermediate Similarity	NPC474323
0.8172	Intermediate Similarity	NPC37607
0.8172	Intermediate Similarity	NPC301969
0.8163	Intermediate Similarity	NPC67296
0.8161	Intermediate Similarity	NPC19841
0.8152	Intermediate Similarity	NPC177629
0.8152	Intermediate Similarity	NPC224652
0.8152	Intermediate Similarity	NPC58219
0.8125	Intermediate Similarity	NPC230800
0.8125	Intermediate Similarity	NPC474297
0.8119	Intermediate Similarity	NPC26617
0.8111	Intermediate Similarity	NPC156485
0.81	Intermediate Similarity	NPC100487
0.8081	Intermediate Similarity	NPC474747
0.8068	Intermediate Similarity	NPC6823
0.8068	Intermediate Similarity	NPC51507
0.8065	Intermediate Similarity	NPC4986
0.8065	Intermediate Similarity	NPC92974
0.8061	Intermediate Similarity	NPC70865
0.8041	Intermediate Similarity	NPC477949
0.8041	Intermediate Similarity	NPC169205
0.8039	Intermediate Similarity	NPC68248
0.8021	Intermediate Similarity	NPC167893
0.8021	Intermediate Similarity	NPC469873
0.802	Intermediate Similarity	NPC166115
0.802	Intermediate Similarity	NPC243998
0.8	Intermediate Similarity	NPC54468
0.8	Intermediate Similarity	NPC143979
0.8	Intermediate Similarity	NPC475945
0.8	Intermediate Similarity	NPC125674
0.8	Intermediate Similarity	NPC475838
0.8	Intermediate Similarity	NPC228451
0.8	Intermediate Similarity	NPC320537
0.8	Intermediate Similarity	NPC475912
0.8	Intermediate Similarity	NPC475871
0.7979	Intermediate Similarity	NPC246173
0.7979	Intermediate Similarity	NPC475855
0.7961	Intermediate Similarity	NPC139838
0.7961	Intermediate Similarity	NPC59489
0.7959	Intermediate Similarity	NPC141191
0.7957	Intermediate Similarity	NPC202672
0.7938	Intermediate Similarity	NPC470883
0.7938	Intermediate Similarity	NPC185553
0.7938	Intermediate Similarity	NPC76862
0.7938	Intermediate Similarity	NPC158416
0.7938	Intermediate Similarity	NPC39859
0.7935	Intermediate Similarity	NPC475019
0.7935	Intermediate Similarity	NPC474949
0.7921	Intermediate Similarity	NPC203659
0.7917	Intermediate Similarity	NPC167219
0.7917	Intermediate Similarity	NPC474338
0.7917	Intermediate Similarity	NPC474247
0.7912	Intermediate Similarity	NPC474780
0.79	Intermediate Similarity	NPC225353
0.7895	Intermediate Similarity	NPC12172
0.7895	Intermediate Similarity	NPC208886
0.7895	Intermediate Similarity	NPC184463
0.7879	Intermediate Similarity	NPC288876
0.7872	Intermediate Similarity	NPC295312
0.7872	Intermediate Similarity	NPC32922
0.7857	Intermediate Similarity	NPC471462
0.7849	Intermediate Similarity	NPC160138
0.7843	Intermediate Similarity	NPC223450
0.7835	Intermediate Similarity	NPC224689
0.7835	Intermediate Similarity	NPC48803
0.7835	Intermediate Similarity	NPC36954
0.7835	Intermediate Similarity	NPC193645
0.7835	Intermediate Similarity	NPC90121
0.7835	Intermediate Similarity	NPC14961
0.7835	Intermediate Similarity	NPC275960
0.7835	Intermediate Similarity	NPC270013
0.783	Intermediate Similarity	NPC273242
0.7826	Intermediate Similarity	NPC329749
0.7826	Intermediate Similarity	NPC255307
0.7826	Intermediate Similarity	NPC165162
0.7822	Intermediate Similarity	NPC124881
0.7822	Intermediate Similarity	NPC110989
0.7812	Intermediate Similarity	NPC81419
0.7812	Intermediate Similarity	NPC179746
0.7812	Intermediate Similarity	NPC212486
0.7802	Intermediate Similarity	NPC128429

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 NPC184063 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	2471
0.2-0.3	3857
0.3-0.4	1734
0.4-0.5	476
0.5-0.6	252
0.6-0.7	41
0.7-0.8	11
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
0.8119	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1695	Approved
0.7835	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6371	Approved
0.7423	Intermediate Similarity	NPD5785	Approved
0.7368	Intermediate Similarity	NPD4249	Approved
0.7292	Intermediate Similarity	NPD4251	Approved
0.7292	Intermediate Similarity	NPD4250	Approved
0.7263	Intermediate Similarity	NPD5363	Approved
0.7204	Intermediate Similarity	NPD5369	Approved
0.7128	Intermediate Similarity	NPD4269	Approved
0.7128	Intermediate Similarity	NPD4270	Approved
0.7091	Intermediate Similarity	NPD6053	Discontinued
0.7053	Intermediate Similarity	NPD5362	Discontinued
0.703	Intermediate Similarity	NPD5282	Discontinued
0.701	Intermediate Similarity	NPD5786	Approved
0.6915	Remote Similarity	NPD4820	Approved
0.6915	Remote Similarity	NPD4252	Approved
0.6915	Remote Similarity	NPD4822	Approved
0.6915	Remote Similarity	NPD4819	Approved
0.6915	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4821	Approved
0.6907	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6698	Approved
0.69	Remote Similarity	NPD46	Approved
0.6875	Remote Similarity	NPD7154	Phase 3
0.6832	Remote Similarity	NPD7983	Approved
0.6771	Remote Similarity	NPD6435	Approved
0.6765	Remote Similarity	NPD5779	Approved
0.6765	Remote Similarity	NPD5778	Approved
0.6762	Remote Similarity	NPD4225	Approved
0.6702	Remote Similarity	NPD4268	Approved
0.6702	Remote Similarity	NPD4271	Approved
0.6698	Remote Similarity	NPD7640	Approved
0.6698	Remote Similarity	NPD7639	Approved
0.6604	Remote Similarity	NPD7638	Approved
0.6569	Remote Similarity	NPD7838	Discovery
0.6562	Remote Similarity	NPD5368	Approved
0.6552	Remote Similarity	NPD7115	Discovery
0.6549	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5331	Approved
0.6531	Remote Similarity	NPD5332	Approved
0.6505	Remote Similarity	NPD7637	Suspended
0.6495	Remote Similarity	NPD4790	Discontinued
0.6449	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6686	Approved
0.6396	Remote Similarity	NPD6008	Approved
0.6354	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4802	Phase 2
0.6354	Remote Similarity	NPD4238	Approved
0.6333	Remote Similarity	NPD8517	Approved
0.6333	Remote Similarity	NPD8515	Approved
0.6333	Remote Similarity	NPD8516	Approved
0.6333	Remote Similarity	NPD8513	Phase 3
0.633	Remote Similarity	NPD5344	Discontinued
0.6311	Remote Similarity	NPD7492	Approved
0.6311	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8133	Approved
0.6286	Remote Similarity	NPD6399	Phase 3
0.6283	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7632	Discontinued
0.6262	Remote Similarity	NPD7839	Suspended
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD6319	Approved
0.624	Remote Similarity	NPD7319	Approved
0.621	Remote Similarity	NPD7078	Approved
0.6204	Remote Similarity	NPD6083	Phase 2
0.6204	Remote Similarity	NPD6084	Phase 2
0.6198	Remote Similarity	NPD6015	Approved
0.6198	Remote Similarity	NPD6016	Approved
0.6195	Remote Similarity	NPD5697	Approved
0.619	Remote Similarity	NPD8035	Phase 2
0.619	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD8034	Phase 2
0.6168	Remote Similarity	NPD5695	Phase 3
0.616	Remote Similarity	NPD7736	Approved
0.6148	Remote Similarity	NPD5988	Approved
0.6148	Remote Similarity	NPD6370	Approved
0.6147	Remote Similarity	NPD5696	Approved
0.614	Remote Similarity	NPD7320	Approved
0.614	Remote Similarity	NPD6881	Approved
0.614	Remote Similarity	NPD6899	Approved
0.6139	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7507	Approved
0.6121	Remote Similarity	NPD6649	Approved
0.6121	Remote Similarity	NPD6650	Approved
0.6116	Remote Similarity	NPD6059	Approved
0.6106	Remote Similarity	NPD7128	Approved
0.6106	Remote Similarity	NPD6675	Approved
0.6106	Remote Similarity	NPD5739	Approved
0.6106	Remote Similarity	NPD6402	Approved
0.61	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD3198	Approved
0.6091	Remote Similarity	NPD6648	Approved
0.6087	Remote Similarity	NPD6373	Approved
0.6087	Remote Similarity	NPD6012	Approved
0.6087	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6014	Approved
0.6087	Remote Similarity	NPD6372	Approved
0.6087	Remote Similarity	NPD6013	Approved
0.608	Remote Similarity	NPD8293	Discontinued
0.608	Remote Similarity	NPD8074	Phase 3
0.6078	Remote Similarity	NPD1694	Approved
0.6066	Remote Similarity	NPD8267	Approved
0.6066	Remote Similarity	NPD8266	Approved
0.6066	Remote Similarity	NPD8269	Approved
0.6066	Remote Similarity	NPD8268	Approved
0.6053	Remote Similarity	NPD6412	Phase 2
0.6053	Remote Similarity	NPD5701	Approved
0.604	Remote Similarity	NPD6695	Phase 3
0.604	Remote Similarity	NPD4788	Approved
0.6034	Remote Similarity	NPD7102	Approved
0.6034	Remote Similarity	NPD6883	Approved
0.6034	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7290	Approved
0.6018	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD5370	Suspended
0.5983	Remote Similarity	NPD8130	Phase 1
0.5983	Remote Similarity	NPD6617	Approved
0.5983	Remote Similarity	NPD6869	Approved
0.5983	Remote Similarity	NPD6847	Approved
0.5982	Remote Similarity	NPD5211	Phase 2
0.5941	Remote Similarity	NPD5209	Approved
0.5932	Remote Similarity	NPD8297	Approved
0.5932	Remote Similarity	NPD6882	Approved
0.5922	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6903	Approved
0.5897	Remote Similarity	NPD4634	Approved
0.5893	Remote Similarity	NPD1700	Approved
0.5888	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5693	Phase 1
0.5888	Remote Similarity	NPD5281	Approved
0.5888	Remote Similarity	NPD5284	Approved
0.5877	Remote Similarity	NPD5141	Approved
0.5872	Remote Similarity	NPD4629	Approved
0.5872	Remote Similarity	NPD5210	Approved
0.5872	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6009	Approved
0.5865	Remote Similarity	NPD7334	Approved
0.5865	Remote Similarity	NPD7146	Approved
0.5865	Remote Similarity	NPD7521	Approved
0.5865	Remote Similarity	NPD5330	Approved
0.5865	Remote Similarity	NPD6684	Approved
0.5865	Remote Similarity	NPD6409	Approved
0.5849	Remote Similarity	NPD4753	Phase 2
0.5825	Remote Similarity	NPD3665	Phase 1
0.5825	Remote Similarity	NPD3133	Approved
0.5825	Remote Similarity	NPD3666	Approved
0.582	Remote Similarity	NPD7328	Approved
0.582	Remote Similarity	NPD7327	Approved
0.5814	Remote Similarity	NPD5956	Approved
0.5814	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7750	Discontinued
0.581	Remote Similarity	NPD7524	Approved
0.5806	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5983	Phase 2
0.5806	Remote Similarity	NPD8033	Approved
0.5804	Remote Similarity	NPD5285	Approved
0.5804	Remote Similarity	NPD5286	Approved
0.5804	Remote Similarity	NPD4696	Approved
0.5794	Remote Similarity	NPD5207	Approved
0.5789	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6274	Approved
0.5784	Remote Similarity	NPD3667	Approved
0.5776	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6685	Approved
0.5772	Remote Similarity	NPD7516	Approved
0.5766	Remote Similarity	NPD4755	Approved
0.5761	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD229	Approved
0.5743	Remote Similarity	NPD6931	Approved
0.5743	Remote Similarity	NPD6930	Phase 2
0.5726	Remote Similarity	NPD8294	Approved
0.5726	Remote Similarity	NPD8377	Approved
0.5725	Remote Similarity	NPD6845	Suspended
0.5714	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3618	Phase 1
0.5714	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7642	Approved
0.5714	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD2204	Approved
0.5702	Remote Similarity	NPD4633	Approved
0.5702	Remote Similarity	NPD5224	Approved
0.5702	Remote Similarity	NPD5225	Approved
0.5702	Remote Similarity	NPD5226	Approved
0.5688	Remote Similarity	NPD4202	Approved
0.568	Remote Similarity	NPD8296	Approved
0.568	Remote Similarity	NPD7503	Approved
0.568	Remote Similarity	NPD8380	Approved
0.568	Remote Similarity	NPD8335	Approved
0.568	Remote Similarity	NPD8379	Approved
0.568	Remote Similarity	NPD6921	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