NPASS Compound

Structure

NPC474313 OpenBabel07101719142D 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 3.0262 5.1627 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 3.2475 3.7659 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 2 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 -1.2910 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 1.5249 3.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4385 4.3537 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.1610 4.1726 0.0000 O 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 1.5997 -0.7852 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 2.0317 5.2672 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 8 2 0 0 0 0 2 9 2 0 0 0 0 3 10 2 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 7 19 1 0 0 0 0 7 20 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 17 1 0 0 0 0 11 6 1 1 0 0 0 11 14 1 0 0 0 0 12 21 1 6 0 0 0 13 15 1 0 0 0 0 13 25 1 6 0 0 0 14 9 1 1 0 0 0 14 16 1 0 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 16 26 1 6 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.15
Volume:	359.86
LogP:	0.237
LogD:	0.616
LogS:	-1.871
# Rotatable Bonds:	4
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	5.096
Fsp3:	0.579
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:	-5.57
MDCK Permeability:	0.00012379317195154727
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.74
20% Bioavailability (F20%):	0.856
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	64.8304443359375%
Volume Distribution (VD):	0.473
Pgp-substrate:	32.28271484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.186
CYP3A4-substrate:	0.25

ADMET: Excretion

Clearance (CL):	2.674
Half-life (T1/2):	0.431

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.675
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.113
Carcinogencity:	0.101
Eye Corrosion:	0.011
Eye Irritation:	0.036
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC474313

Natural Product ID:	NPC474313
*Common Name:**	3-Alpha-Dihydro-4(15)-Dehydrogrosshemin Alpha,Beta-Dihydroxyisoburyrate
IUPAC Name:	[(3aR,4S,6aR,8R,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] 2,3-dihydroxy-2-methylpropanoate
Synonyms:
Standard InCHIKey:	NPBDPFOGSVKPOK-MKQGLTGQSA-N
Standard InCHI:	InChI=1S/C19H24O7/c1-8-5-13(25-18(23)19(4,24)7-20)15-10(3)17(22)26-16(15)14-9(2)12(21)6-11(8)14/h11-16,20-21,24H,1-3,5-7H2,4H3/t11-,12+,13-,14-,15+,16+,19?/m0/s1
SMILES:	CC(CO)(C(=O)OC1CC(=C)C2CC(C(=C)C2C3C1C(=C)C(=O)O3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465053
PubChem CID:	44567547
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[514906]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	18.04	uM	PMID[514906]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	10.52	uM	PMID[514906]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	28.76	uM	PMID[514906]

☑ 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 NPC474313 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	278
0.1-0.2	1794
0.2-0.3	6074
0.3-0.4	13264
0.4-0.5	10849
0.5-0.6	6977
0.6-0.7	2745
0.7-0.8	565
0.8-0.85	99
0.85-0.9	45
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC475788
0.9444	High Similarity	NPC184063
0.9333	High Similarity	NPC19087
0.9222	High Similarity	NPC38392
0.9111	High Similarity	NPC207114
0.9111	High Similarity	NPC217983
0.9082	High Similarity	NPC44004
0.9043	High Similarity	NPC476009
0.8947	High Similarity	NPC311904
0.8947	High Similarity	NPC471150
0.8936	High Similarity	NPC472873
0.8936	High Similarity	NPC475900
0.8889	High Similarity	NPC187661
0.883	High Similarity	NPC473331
0.8804	High Similarity	NPC215556
0.8737	High Similarity	NPC163228
0.871	High Similarity	NPC297474
0.871	High Similarity	NPC54065
0.871	High Similarity	NPC216284
0.8696	High Similarity	NPC79549
0.8687	High Similarity	NPC473148
0.8681	High Similarity	NPC304558
0.8667	High Similarity	NPC224386
0.8667	High Similarity	NPC194859
0.8646	High Similarity	NPC142529
0.8646	High Similarity	NPC91771
0.8617	High Similarity	NPC57304
0.8617	High Similarity	NPC475925
0.8617	High Similarity	NPC35959
0.8617	High Similarity	NPC29821
0.8617	High Similarity	NPC171360
0.8617	High Similarity	NPC293001
0.8617	High Similarity	NPC133888
0.8617	High Similarity	NPC63193
0.8614	High Similarity	NPC26617
0.8602	High Similarity	NPC155935
0.8586	High Similarity	NPC474747
0.8571	High Similarity	NPC471381
0.8571	High Similarity	NPC186861
0.8557	High Similarity	NPC181151
0.8556	High Similarity	NPC128246
0.8542	High Similarity	NPC476053
0.8529	High Similarity	NPC68248
0.8526	High Similarity	NPC473273
0.8526	High Similarity	NPC60386
0.8526	High Similarity	NPC258216
0.8526	High Similarity	NPC308656
0.8526	High Similarity	NPC473263
0.8526	High Similarity	NPC473234
0.8511	High Similarity	NPC35809
0.85	High Similarity	NPC475871
0.85	High Similarity	NPC475945
0.8485	Intermediate Similarity	NPC150923
0.8469	Intermediate Similarity	NPC249171
0.8469	Intermediate Similarity	NPC49833
0.8469	Intermediate Similarity	NPC45125
0.8454	Intermediate Similarity	NPC76862
0.8454	Intermediate Similarity	NPC470883
0.8454	Intermediate Similarity	NPC39859
0.8454	Intermediate Similarity	NPC158416
0.8444	Intermediate Similarity	NPC246076
0.8438	Intermediate Similarity	NPC198853
0.8421	Intermediate Similarity	NPC155215
0.84	Intermediate Similarity	NPC80144
0.84	Intermediate Similarity	NPC86077
0.8387	Intermediate Similarity	NPC190753
0.8387	Intermediate Similarity	NPC118601
0.8387	Intermediate Similarity	NPC186148
0.837	Intermediate Similarity	NPC204105
0.837	Intermediate Similarity	NPC284534
0.837	Intermediate Similarity	NPC300082
0.8367	Intermediate Similarity	NPC236580
0.8367	Intermediate Similarity	NPC304445
0.8351	Intermediate Similarity	NPC170120
0.8351	Intermediate Similarity	NPC213698
0.8333	Intermediate Similarity	NPC153590
0.8333	Intermediate Similarity	NPC200237
0.8333	Intermediate Similarity	NPC54737
0.8333	Intermediate Similarity	NPC126248
0.8316	Intermediate Similarity	NPC206614
0.8316	Intermediate Similarity	NPC474323
0.83	Intermediate Similarity	NPC171759
0.83	Intermediate Similarity	NPC474742
0.83	Intermediate Similarity	NPC67296
0.8298	Intermediate Similarity	NPC53158
0.8298	Intermediate Similarity	NPC177629
0.8298	Intermediate Similarity	NPC58219
0.8298	Intermediate Similarity	NPC178875
0.828	Intermediate Similarity	NPC56593
0.8265	Intermediate Similarity	NPC18019
0.8265	Intermediate Similarity	NPC24956
0.8265	Intermediate Similarity	NPC474297
0.8247	Intermediate Similarity	NPC262133
0.8247	Intermediate Similarity	NPC470010
0.8247	Intermediate Similarity	NPC323008
0.8247	Intermediate Similarity	NPC127019
0.8247	Intermediate Similarity	NPC190294
0.8247	Intermediate Similarity	NPC470013
0.8235	Intermediate Similarity	NPC474741
0.8235	Intermediate Similarity	NPC100487
0.8229	Intermediate Similarity	NPC286341
0.8229	Intermediate Similarity	NPC191339
0.8229	Intermediate Similarity	NPC131209
0.8229	Intermediate Similarity	NPC133698
0.8211	Intermediate Similarity	NPC12872
0.8211	Intermediate Similarity	NPC92974
0.8211	Intermediate Similarity	NPC173926
0.8211	Intermediate Similarity	NPC472872
0.8211	Intermediate Similarity	NPC168679
0.82	Intermediate Similarity	NPC70865
0.8191	Intermediate Similarity	NPC201658
0.8191	Intermediate Similarity	NPC24728
0.8182	Intermediate Similarity	NPC161493
0.8182	Intermediate Similarity	NPC108475
0.8182	Intermediate Similarity	NPC170143
0.8182	Intermediate Similarity	NPC213947
0.8163	Intermediate Similarity	NPC67584
0.8163	Intermediate Similarity	NPC52044
0.8163	Intermediate Similarity	NPC304886
0.8155	Intermediate Similarity	NPC243998
0.8152	Intermediate Similarity	NPC111409
0.8152	Intermediate Similarity	NPC245665
0.8144	Intermediate Similarity	NPC472874
0.8144	Intermediate Similarity	NPC475912
0.8137	Intermediate Similarity	NPC475873
0.8105	Intermediate Similarity	NPC471149
0.8095	Intermediate Similarity	NPC139838
0.8095	Intermediate Similarity	NPC59489
0.8085	Intermediate Similarity	NPC474949
0.8085	Intermediate Similarity	NPC236692
0.8085	Intermediate Similarity	NPC470242
0.8085	Intermediate Similarity	NPC309757
0.8085	Intermediate Similarity	NPC64153
0.8085	Intermediate Similarity	NPC475019
0.8081	Intermediate Similarity	NPC213078
0.8065	Intermediate Similarity	NPC474780
0.8061	Intermediate Similarity	NPC477131
0.8058	Intermediate Similarity	NPC203659
0.8041	Intermediate Similarity	NPC184463
0.8041	Intermediate Similarity	NPC208886
0.8041	Intermediate Similarity	NPC12172
0.8039	Intermediate Similarity	NPC225353
0.8039	Intermediate Similarity	NPC471148
0.8021	Intermediate Similarity	NPC283409
0.8021	Intermediate Similarity	NPC474951
0.8	Intermediate Similarity	NPC117604
0.8	Intermediate Similarity	NPC323421
0.8	Intermediate Similarity	NPC255082
0.8	Intermediate Similarity	NPC328562
0.7981	Intermediate Similarity	NPC223450
0.798	Intermediate Similarity	NPC167893
0.798	Intermediate Similarity	NPC270013
0.798	Intermediate Similarity	NPC36954
0.798	Intermediate Similarity	NPC14961
0.7979	Intermediate Similarity	NPC329749
0.7961	Intermediate Similarity	NPC124881
0.7961	Intermediate Similarity	NPC110989
0.7959	Intermediate Similarity	NPC469645
0.7959	Intermediate Similarity	NPC212486
0.7959	Intermediate Similarity	NPC469692
0.7959	Intermediate Similarity	NPC81419
0.7959	Intermediate Similarity	NPC179746
0.7941	Intermediate Similarity	NPC185141
0.7941	Intermediate Similarity	NPC474339
0.7941	Intermediate Similarity	NPC47880
0.7941	Intermediate Similarity	NPC46998
0.7941	Intermediate Similarity	NPC128733
0.7941	Intermediate Similarity	NPC110443
0.7941	Intermediate Similarity	NPC133907
0.7941	Intermediate Similarity	NPC201718
0.7941	Intermediate Similarity	NPC164598
0.7938	Intermediate Similarity	NPC246173
0.7921	Intermediate Similarity	NPC187268
0.7921	Intermediate Similarity	NPC471144
0.7921	Intermediate Similarity	NPC221615
0.7917	Intermediate Similarity	NPC202672
0.7917	Intermediate Similarity	NPC91248
0.79	Intermediate Similarity	NPC31645
0.79	Intermediate Similarity	NPC126156
0.7895	Intermediate Similarity	NPC476015
0.7895	Intermediate Similarity	NPC162071
0.7895	Intermediate Similarity	NPC238593
0.7895	Intermediate Similarity	NPC474762
0.7895	Intermediate Similarity	NPC67493
0.789	Intermediate Similarity	NPC121816
0.7885	Intermediate Similarity	NPC220964
0.7885	Intermediate Similarity	NPC475676
0.7879	Intermediate Similarity	NPC474035
0.7879	Intermediate Similarity	NPC81386
0.7879	Intermediate Similarity	NPC121825
0.7872	Intermediate Similarity	NPC151176
0.7872	Intermediate Similarity	NPC3464
0.7872	Intermediate Similarity	NPC475963
0.7864	Intermediate Similarity	NPC149371
0.7857	Intermediate Similarity	NPC329952
0.7857	Intermediate Similarity	NPC30515
0.7857	Intermediate Similarity	NPC469627
0.7857	Intermediate Similarity	NPC475881
0.7857	Intermediate Similarity	NPC70251
0.785	Intermediate Similarity	NPC257240

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 NPC474313 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	2549
0.2-0.3	3783
0.3-0.4	1655
0.4-0.5	525
0.5-0.6	247
0.6-0.7	54
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8614	High Similarity	NPD7899	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD6371	Approved
0.7653	Intermediate Similarity	NPD1695	Approved
0.7451	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD46	Approved
0.7059	Intermediate Similarity	NPD6698	Approved
0.7059	Intermediate Similarity	NPD5785	Approved
0.7019	Intermediate Similarity	NPD5282	Discontinued
0.7	Intermediate Similarity	NPD4249	Approved
0.6991	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7983	Approved
0.6931	Remote Similarity	NPD4251	Approved
0.6931	Remote Similarity	NPD4250	Approved
0.6916	Remote Similarity	NPD4225	Approved
0.69	Remote Similarity	NPD5363	Approved
0.69	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5369	Approved
0.6783	Remote Similarity	NPD6053	Discontinued
0.6768	Remote Similarity	NPD4270	Approved
0.6768	Remote Similarity	NPD4269	Approved
0.6731	Remote Similarity	NPD7838	Discovery
0.6726	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5362	Discontinued
0.6695	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6585	Remote Similarity	NPD7492	Approved
0.6579	Remote Similarity	NPD6686	Approved
0.6569	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4820	Approved
0.6566	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4819	Approved
0.6566	Remote Similarity	NPD4821	Approved
0.6566	Remote Similarity	NPD4252	Approved
0.6566	Remote Similarity	NPD4822	Approved
0.6535	Remote Similarity	NPD7154	Phase 3
0.6532	Remote Similarity	NPD6616	Approved
0.6529	Remote Similarity	NPD6054	Approved
0.6486	Remote Similarity	NPD5344	Discontinued
0.648	Remote Similarity	NPD7078	Approved
0.6475	Remote Similarity	NPD6016	Approved
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD6015	Approved
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD8515	Approved
0.646	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5779	Approved
0.6449	Remote Similarity	NPD5778	Approved
0.6441	Remote Similarity	NPD4632	Approved
0.6441	Remote Similarity	NPD8133	Approved
0.6436	Remote Similarity	NPD6435	Approved
0.6429	Remote Similarity	NPD7736	Approved
0.6423	Remote Similarity	NPD5988	Approved
0.6423	Remote Similarity	NPD6370	Approved
0.6396	Remote Similarity	NPD7640	Approved
0.6396	Remote Similarity	NPD7639	Approved
0.6393	Remote Similarity	NPD6059	Approved
0.6378	Remote Similarity	NPD7319	Approved
0.6364	Remote Similarity	NPD4268	Approved
0.6364	Remote Similarity	NPD4271	Approved
0.6349	Remote Similarity	NPD8293	Discontinued
0.6306	Remote Similarity	NPD7638	Approved
0.627	Remote Similarity	NPD7507	Approved
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5368	Approved
0.622	Remote Similarity	NPD8074	Phase 3
0.6218	Remote Similarity	NPD8297	Approved
0.6216	Remote Similarity	NPD6083	Phase 2
0.6216	Remote Similarity	NPD6084	Phase 2
0.6214	Remote Similarity	NPD5332	Approved
0.6214	Remote Similarity	NPD5331	Approved
0.6207	Remote Similarity	NPD5697	Approved
0.6207	Remote Similarity	NPD6412	Phase 2
0.6204	Remote Similarity	NPD7637	Suspended
0.6195	Remote Similarity	NPD1700	Approved
0.6186	Remote Similarity	NPD4634	Approved
0.6182	Remote Similarity	NPD5695	Phase 3
0.6176	Remote Similarity	NPD4790	Discontinued
0.6165	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5696	Approved
0.6154	Remote Similarity	NPD6899	Approved
0.6154	Remote Similarity	NPD6881	Approved
0.6154	Remote Similarity	NPD7320	Approved
0.6148	Remote Similarity	NPD6009	Approved
0.6142	Remote Similarity	NPD8273	Phase 1
0.6134	Remote Similarity	NPD2204	Approved
0.6134	Remote Similarity	NPD6650	Approved
0.6134	Remote Similarity	NPD6649	Approved
0.6121	Remote Similarity	NPD5739	Approved
0.6121	Remote Similarity	NPD7128	Approved
0.6121	Remote Similarity	NPD6402	Approved
0.6121	Remote Similarity	NPD6008	Approved
0.6121	Remote Similarity	NPD6675	Approved
0.6106	Remote Similarity	NPD6648	Approved
0.6102	Remote Similarity	NPD6372	Approved
0.6102	Remote Similarity	NPD6012	Approved
0.6102	Remote Similarity	NPD6013	Approved
0.6102	Remote Similarity	NPD6014	Approved
0.6102	Remote Similarity	NPD6373	Approved
0.608	Remote Similarity	NPD8269	Approved
0.608	Remote Similarity	NPD8266	Approved
0.608	Remote Similarity	NPD5983	Phase 2
0.608	Remote Similarity	NPD8267	Approved
0.608	Remote Similarity	NPD8268	Approved
0.608	Remote Similarity	NPD6921	Approved
0.6077	Remote Similarity	NPD5956	Approved
0.6068	Remote Similarity	NPD5701	Approved
0.605	Remote Similarity	NPD7290	Approved
0.605	Remote Similarity	NPD6883	Approved
0.605	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7102	Approved
0.604	Remote Similarity	NPD4802	Phase 2
0.604	Remote Similarity	NPD4238	Approved
0.604	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6101	Approved
0.6019	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5985	Remote Similarity	NPD6845	Suspended
0.5984	Remote Similarity	NPD7604	Phase 2
0.5982	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7839	Suspended
0.5981	Remote Similarity	NPD7524	Approved
0.5968	Remote Similarity	NPD7328	Approved
0.5968	Remote Similarity	NPD7327	Approved
0.5952	Remote Similarity	NPD8033	Approved
0.595	Remote Similarity	NPD6882	Approved
0.5923	Remote Similarity	NPD6033	Approved
0.592	Remote Similarity	NPD7516	Approved
0.5909	Remote Similarity	NPD8035	Phase 2
0.5909	Remote Similarity	NPD5693	Phase 1
0.5909	Remote Similarity	NPD6411	Approved
0.5909	Remote Similarity	NPD8034	Phase 2
0.5909	Remote Similarity	NPD7260	Phase 2
0.5905	Remote Similarity	NPD6110	Phase 1
0.5897	Remote Similarity	NPD5141	Approved
0.5893	Remote Similarity	NPD5210	Approved
0.5893	Remote Similarity	NPD4629	Approved
0.5891	Remote Similarity	NPD6336	Discontinued
0.5887	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD8377	Approved
0.5873	Remote Similarity	NPD8294	Approved
0.5872	Remote Similarity	NPD4753	Phase 2
0.5859	Remote Similarity	NPD7642	Approved
0.5859	Remote Similarity	NPD8328	Phase 3
0.5849	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7503	Approved
0.5827	Remote Similarity	NPD8380	Approved
0.5827	Remote Similarity	NPD8296	Approved
0.5827	Remote Similarity	NPD8379	Approved
0.5827	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD8335	Approved
0.5827	Remote Similarity	NPD8378	Approved
0.5826	Remote Similarity	NPD5286	Approved
0.5826	Remote Similarity	NPD4696	Approved
0.5826	Remote Similarity	NPD5285	Approved
0.581	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6274	Approved
0.5798	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD1694	Approved
0.5794	Remote Similarity	NPD4522	Approved
0.5789	Remote Similarity	NPD4755	Approved
0.5781	Remote Similarity	NPD8080	Discontinued
0.5769	Remote Similarity	NPD8451	Approved
0.5761	Remote Similarity	NPD3198	Approved
0.5755	Remote Similarity	NPD6695	Phase 3
0.5755	Remote Similarity	NPD4788	Approved
0.5738	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD7829	Approved
0.5736	Remote Similarity	NPD7830	Approved
0.5727	Remote Similarity	NPD5370	Suspended
0.5726	Remote Similarity	NPD5226	Approved
0.5726	Remote Similarity	NPD5224	Approved
0.5726	Remote Similarity	NPD5225	Approved
0.5726	Remote Similarity	NPD4633	Approved
0.5725	Remote Similarity	NPD8448	Approved
0.5703	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD8299	Approved
0.5692	Remote Similarity	NPD8342	Approved
0.5692	Remote Similarity	NPD8341	Approved
0.5692	Remote Similarity	NPD8340	Approved
0.569	Remote Similarity	NPD4700	Approved
0.5678	Remote Similarity	NPD5174	Approved
0.5678	Remote Similarity	NPD5175	Approved
0.5669	Remote Similarity	NPD7100	Approved
0.5669	Remote Similarity	NPD7101	Approved
0.566	Remote Similarity	NPD5209	Approved
0.5648	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5223	Approved
0.5636	Remote Similarity	NPD5737	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