NPASS Compound

Structure

NPC473966 OpenBabel07101719242D 28 31 0 0 1 0 0 0 0 0999 V2000 1.0249 2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6559 2.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 8 2 0 0 0 0 6 10 2 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 21 2 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 11 27 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 28 1 0 0 0 0 19 26 1 0 0 0 0 19 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.13
Volume:	374.753
LogP:	0.969
LogD:	0.973
LogS:	-2.103
# Rotatable Bonds:	1
TPSA:	137.43
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	4.633
Fsp3:	0.5
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:	-5.268
MDCK Permeability:	0.00025644301786087453
Pgp-inhibitor:	0.001
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.214
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.407
Plasma Protein Binding (PPB):	78.54535675048828%
Volume Distribution (VD):	0.978
Pgp-substrate:	40.640865325927734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.722
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.641
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	0.953
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.401
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.26
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.029
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.642

Download Data

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

Natural Product: NPC473966

Natural Product ID:	NPC473966
*Common Name:**	Sigmoidin G
IUPAC Name:	2-(2,3,4,7,8-pentahydroxy-5,5-dimethyl-2,3,4,4a-tetrahydrochromen-6-yl)-2,3-dihydrochromen-4-one
Synonyms:	Sigmoidin G
Standard InCHIKey:	OYKVSVOHAHXIEQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H22O8/c1-20(2)12(11-7-9(21)8-5-3-4-6-10(8)27-11)14(22)16(24)18-13(20)15(23)17(25)19(26)28-18/h3-6,11,13,15,17,19,22-26H,7H2,1-2H3
SMILES:	CC1(C2C(C(C(OC2=C(C(=C1C3CC(=O)C4=CC=CC=C4O3)O)O)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456655
PubChem CID:	44589234
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8526	Erythrina abyssinica	Species	Fabaceae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	60000.0	nM	PMID[468496]

☑ 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 NPC473966 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	350
0.1-0.2	1247
0.2-0.3	2670
0.3-0.4	6064
0.4-0.5	10627
0.5-0.6	6546
0.6-0.7	6186
0.7-0.8	8312
0.8-0.85	628
0.85-0.9	66
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8968	High Similarity	NPC271479
0.8903	High Similarity	NPC308265
0.8861	High Similarity	NPC475979
0.8816	High Similarity	NPC213723
0.879	High Similarity	NPC303913
0.8782	High Similarity	NPC73511
0.8774	High Similarity	NPC170475
0.8774	High Similarity	NPC206378
0.8774	High Similarity	NPC45165
0.8758	High Similarity	NPC190217
0.875	High Similarity	NPC63470
0.8742	High Similarity	NPC294722
0.8734	High Similarity	NPC146837
0.8734	High Similarity	NPC278329
0.8726	High Similarity	NPC472320
0.8718	High Similarity	NPC197896
0.8718	High Similarity	NPC177742
0.8718	High Similarity	NPC156457
0.8718	High Similarity	NPC258035
0.8718	High Similarity	NPC313163
0.8718	High Similarity	NPC161749
0.871	High Similarity	NPC169248
0.871	High Similarity	NPC26195
0.871	High Similarity	NPC72649
0.871	High Similarity	NPC99233
0.871	High Similarity	NPC39351
0.871	High Similarity	NPC97052
0.8693	High Similarity	NPC131874
0.8693	High Similarity	NPC477240
0.8693	High Similarity	NPC106025
0.8693	High Similarity	NPC214454
0.8684	High Similarity	NPC22137
0.8662	High Similarity	NPC43761
0.8649	High Similarity	NPC79908
0.8645	High Similarity	NPC470331
0.8645	High Similarity	NPC106625
0.8636	High Similarity	NPC134819
0.8627	High Similarity	NPC104172
0.8627	High Similarity	NPC88886
0.8625	High Similarity	NPC178281
0.8618	High Similarity	NPC218685
0.8618	High Similarity	NPC472339
0.8616	High Similarity	NPC101116
0.8616	High Similarity	NPC44947
0.8616	High Similarity	NPC259834
0.8616	High Similarity	NPC212099
0.8609	High Similarity	NPC474044
0.8608	High Similarity	NPC246469
0.8608	High Similarity	NPC271270
0.8608	High Similarity	NPC200708
0.8608	High Similarity	NPC142860
0.8608	High Similarity	NPC153342
0.8608	High Similarity	NPC473623
0.8608	High Similarity	NPC97285
0.8608	High Similarity	NPC328093
0.8599	High Similarity	NPC65003
0.8599	High Similarity	NPC44931
0.8599	High Similarity	NPC129827
0.8599	High Similarity	NPC473512
0.8599	High Similarity	NPC23817
0.8599	High Similarity	NPC43638
0.8591	High Similarity	NPC31081
0.8591	High Similarity	NPC245219
0.859	High Similarity	NPC27408
0.859	High Similarity	NPC470603
0.859	High Similarity	NPC470605
0.859	High Similarity	NPC470604
0.859	High Similarity	NPC95090
0.8581	High Similarity	NPC121001
0.8581	High Similarity	NPC259182
0.8581	High Similarity	NPC88484
0.8581	High Similarity	NPC259767
0.858	High Similarity	NPC246274
0.8571	High Similarity	NPC191154
0.8562	High Similarity	NPC124155
0.8562	High Similarity	NPC257566
0.8562	High Similarity	NPC199335
0.8562	High Similarity	NPC127415
0.8553	High Similarity	NPC47923
0.8544	High Similarity	NPC22062
0.8544	High Similarity	NPC473634
0.8544	High Similarity	NPC138811
0.8535	High Similarity	NPC127406
0.8535	High Similarity	NPC473657
0.8535	High Similarity	NPC295613
0.8526	High Similarity	NPC210003
0.8526	High Similarity	NPC279281
0.8526	High Similarity	NPC83283
0.8526	High Similarity	NPC78021
0.8526	High Similarity	NPC29763
0.8526	High Similarity	NPC39360
0.8526	High Similarity	NPC185103
0.8526	High Similarity	NPC92153
0.8526	High Similarity	NPC87304
0.8526	High Similarity	NPC230439
0.8526	High Similarity	NPC299761
0.8526	High Similarity	NPC211158
0.8526	High Similarity	NPC268950
0.8526	High Similarity	NPC143851
0.8526	High Similarity	NPC108706
0.8516	High Similarity	NPC23253
0.8509	High Similarity	NPC99216
0.85	High Similarity	NPC472876
0.85	High Similarity	NPC190450
0.85	High Similarity	NPC61594
0.85	High Similarity	NPC56735
0.85	High Similarity	NPC131745
0.85	High Similarity	NPC216752
0.8497	Intermediate Similarity	NPC83975
0.8497	Intermediate Similarity	NPC23084
0.8497	Intermediate Similarity	NPC302989
0.8491	Intermediate Similarity	NPC187379
0.8485	Intermediate Similarity	NPC307754
0.8485	Intermediate Similarity	NPC223735
0.8481	Intermediate Similarity	NPC476026
0.8481	Intermediate Similarity	NPC474401
0.8481	Intermediate Similarity	NPC6985
0.8481	Intermediate Similarity	NPC474398
0.8481	Intermediate Similarity	NPC182634
0.8481	Intermediate Similarity	NPC474441
0.8481	Intermediate Similarity	NPC108831
0.8481	Intermediate Similarity	NPC60966
0.8481	Intermediate Similarity	NPC470606
0.8477	Intermediate Similarity	NPC471028
0.8476	Intermediate Similarity	NPC315619
0.8466	Intermediate Similarity	NPC229687
0.8462	Intermediate Similarity	NPC34965
0.8462	Intermediate Similarity	NPC183536
0.8462	Intermediate Similarity	NPC215811
0.8457	Intermediate Similarity	NPC5778
0.8457	Intermediate Similarity	NPC70441
0.8457	Intermediate Similarity	NPC236934
0.8447	Intermediate Similarity	NPC473644
0.8447	Intermediate Similarity	NPC66087
0.8447	Intermediate Similarity	NPC29830
0.8447	Intermediate Similarity	NPC147596
0.8447	Intermediate Similarity	NPC183672
0.8447	Intermediate Similarity	NPC278419
0.8447	Intermediate Similarity	NPC179198
0.8442	Intermediate Similarity	NPC191634
0.8438	Intermediate Similarity	NPC116458
0.8438	Intermediate Similarity	NPC173582
0.8438	Intermediate Similarity	NPC181465
0.8438	Intermediate Similarity	NPC139320
0.8438	Intermediate Similarity	NPC473438
0.8438	Intermediate Similarity	NPC101636
0.8438	Intermediate Similarity	NPC215710
0.8438	Intermediate Similarity	NPC246943
0.8438	Intermediate Similarity	NPC276377
0.8438	Intermediate Similarity	NPC476215
0.8438	Intermediate Similarity	NPC265885
0.8438	Intermediate Similarity	NPC249281
0.8438	Intermediate Similarity	NPC163242
0.8438	Intermediate Similarity	NPC253788
0.8428	Intermediate Similarity	NPC320283
0.8428	Intermediate Similarity	NPC57072
0.8428	Intermediate Similarity	NPC111929
0.8428	Intermediate Similarity	NPC472459
0.8428	Intermediate Similarity	NPC41121
0.8428	Intermediate Similarity	NPC231475
0.8428	Intermediate Similarity	NPC470607
0.8424	Intermediate Similarity	NPC203751
0.8418	Intermediate Similarity	NPC307938
0.8418	Intermediate Similarity	NPC17521
0.8418	Intermediate Similarity	NPC261866
0.8418	Intermediate Similarity	NPC203500
0.8418	Intermediate Similarity	NPC323593
0.8418	Intermediate Similarity	NPC149368
0.8418	Intermediate Similarity	NPC265480
0.8415	Intermediate Similarity	NPC231194
0.8415	Intermediate Similarity	NPC44558
0.8415	Intermediate Similarity	NPC51326
0.8408	Intermediate Similarity	NPC299435
0.8408	Intermediate Similarity	NPC260604
0.8408	Intermediate Similarity	NPC472128
0.8408	Intermediate Similarity	NPC472127
0.8405	Intermediate Similarity	NPC298847
0.8405	Intermediate Similarity	NPC229729
0.8405	Intermediate Similarity	NPC45400
0.84	Intermediate Similarity	NPC80098
0.8395	Intermediate Similarity	NPC472131
0.8395	Intermediate Similarity	NPC472130
0.8387	Intermediate Similarity	NPC307052
0.8387	Intermediate Similarity	NPC139966
0.8385	Intermediate Similarity	NPC127782
0.8385	Intermediate Similarity	NPC240306
0.8385	Intermediate Similarity	NPC298171
0.8385	Intermediate Similarity	NPC475382
0.8385	Intermediate Similarity	NPC300537
0.8378	Intermediate Similarity	NPC294470
0.8377	Intermediate Similarity	NPC140722
0.8377	Intermediate Similarity	NPC4958
0.8377	Intermediate Similarity	NPC92054
0.8375	Intermediate Similarity	NPC136761
0.8375	Intermediate Similarity	NPC470405
0.8375	Intermediate Similarity	NPC471079
0.8375	Intermediate Similarity	NPC304741
0.8366	Intermediate Similarity	NPC291153
0.8365	Intermediate Similarity	NPC77672
0.8365	Intermediate Similarity	NPC122809

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 NPC473966 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	794
0.2-0.3	1556
0.3-0.4	2476
0.4-0.5	2167
0.5-0.6	1173
0.6-0.7	515
0.7-0.8	164
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8718	High Similarity	NPD4381	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD8312	Approved
0.8323	Intermediate Similarity	NPD8313	Approved
0.8303	Intermediate Similarity	NPD7074	Phase 3
0.8242	Intermediate Similarity	NPD7054	Approved
0.8217	Intermediate Similarity	NPD4380	Phase 2
0.8193	Intermediate Similarity	NPD7472	Approved
0.8144	Intermediate Similarity	NPD6797	Phase 2
0.8141	Intermediate Similarity	NPD5403	Approved
0.8105	Intermediate Similarity	NPD4628	Phase 3
0.8095	Intermediate Similarity	NPD6559	Discontinued
0.8095	Intermediate Similarity	NPD7251	Discontinued
0.8072	Intermediate Similarity	NPD3818	Discontinued
0.8047	Intermediate Similarity	NPD7808	Phase 3
0.8025	Intermediate Similarity	NPD7075	Discontinued
0.8013	Intermediate Similarity	NPD5401	Approved
0.8012	Intermediate Similarity	NPD5402	Approved
0.7952	Intermediate Similarity	NPD6166	Phase 2
0.7952	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD8455	Phase 2
0.7945	Intermediate Similarity	NPD2798	Approved
0.7901	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6801	Discontinued
0.7888	Intermediate Similarity	NPD1934	Approved
0.7875	Intermediate Similarity	NPD6599	Discontinued
0.7857	Intermediate Similarity	NPD1549	Phase 2
0.784	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7411	Suspended
0.7792	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7819	Suspended
0.7727	Intermediate Similarity	NPD2796	Approved
0.7724	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1091	Approved
0.7722	Intermediate Similarity	NPD6799	Approved
0.7711	Intermediate Similarity	NPD5494	Approved
0.7702	Intermediate Similarity	NPD7458	Discontinued
0.7684	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2799	Discontinued
0.7643	Intermediate Similarity	NPD3750	Approved
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.76	Intermediate Similarity	NPD6832	Phase 2
0.7593	Intermediate Similarity	NPD3226	Approved
0.7582	Intermediate Similarity	NPD1933	Approved
0.758	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3817	Phase 2
0.7564	Intermediate Similarity	NPD2346	Discontinued
0.7562	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6959	Discontinued
0.7557	Intermediate Similarity	NPD8434	Phase 2
0.7551	Intermediate Similarity	NPD9717	Approved
0.7548	Intermediate Similarity	NPD1510	Phase 2
0.7544	Intermediate Similarity	NPD3751	Discontinued
0.753	Intermediate Similarity	NPD7768	Phase 2
0.7529	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD447	Suspended
0.7468	Intermediate Similarity	NPD2800	Approved
0.7436	Intermediate Similarity	NPD7033	Discontinued
0.7436	Intermediate Similarity	NPD3748	Approved
0.7425	Intermediate Similarity	NPD3882	Suspended
0.7414	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1240	Approved
0.74	Intermediate Similarity	NPD1203	Approved
0.74	Intermediate Similarity	NPD2797	Approved
0.7399	Intermediate Similarity	NPD5844	Phase 1
0.7391	Intermediate Similarity	NPD6776	Approved
0.7391	Intermediate Similarity	NPD6777	Approved
0.7391	Intermediate Similarity	NPD6780	Approved
0.7391	Intermediate Similarity	NPD6781	Approved
0.7391	Intermediate Similarity	NPD6778	Approved
0.7391	Intermediate Similarity	NPD6782	Approved
0.7391	Intermediate Similarity	NPD1511	Approved
0.7391	Intermediate Similarity	NPD6779	Approved
0.7389	Intermediate Similarity	NPD2935	Discontinued
0.7386	Intermediate Similarity	NPD3268	Approved
0.7374	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7685	Pre-registration
0.7355	Intermediate Similarity	NPD6355	Discontinued
0.7351	Intermediate Similarity	NPD5647	Approved
0.7349	Intermediate Similarity	NPD6844	Discontinued
0.7346	Intermediate Similarity	NPD4661	Approved
0.7346	Intermediate Similarity	NPD4662	Approved
0.7342	Intermediate Similarity	NPD6002	Phase 3
0.7342	Intermediate Similarity	NPD6005	Phase 3
0.7342	Intermediate Similarity	NPD7266	Discontinued
0.7342	Intermediate Similarity	NPD6004	Phase 3
0.7342	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1653	Approved
0.7312	Intermediate Similarity	NPD6823	Phase 2
0.731	Intermediate Similarity	NPD3787	Discontinued
0.7308	Intermediate Similarity	NPD1607	Approved
0.7308	Intermediate Similarity	NPD6651	Approved
0.7301	Intermediate Similarity	NPD1512	Approved
0.7301	Intermediate Similarity	NPD6273	Approved
0.7296	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6100	Approved
0.7278	Intermediate Similarity	NPD3749	Approved
0.7278	Intermediate Similarity	NPD6099	Approved
0.7273	Intermediate Similarity	NPD7697	Approved
0.7273	Intermediate Similarity	NPD7435	Discontinued
0.7273	Intermediate Similarity	NPD7698	Approved
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD7696	Phase 3
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7261	Intermediate Similarity	NPD7097	Phase 1
0.7251	Intermediate Similarity	NPD8127	Discontinued
0.7249	Intermediate Similarity	NPD7584	Approved
0.7244	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7228	Approved
0.7237	Intermediate Similarity	NPD1019	Discontinued
0.7233	Intermediate Similarity	NPD2344	Approved
0.7233	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8651	Approved
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7211	Intermediate Similarity	NPD7701	Phase 2
0.7205	Intermediate Similarity	NPD7003	Approved
0.7202	Intermediate Similarity	NPD1465	Phase 2
0.7188	Intermediate Similarity	NPD2424	Discontinued
0.7184	Intermediate Similarity	NPD7473	Discontinued
0.7161	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD411	Approved
0.7151	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7135	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5124	Phase 1
0.7123	Intermediate Similarity	NPD7157	Approved
0.712	Intermediate Similarity	NPD6535	Approved
0.712	Intermediate Similarity	NPD6534	Approved
0.7118	Intermediate Similarity	NPD4965	Approved
0.7118	Intermediate Similarity	NPD4967	Phase 2
0.7118	Intermediate Similarity	NPD4966	Approved
0.7115	Intermediate Similarity	NPD6233	Phase 2
0.7111	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6232	Discontinued
0.7103	Intermediate Similarity	NPD1241	Discontinued
0.7101	Intermediate Similarity	NPD5760	Phase 2
0.7101	Intermediate Similarity	NPD5761	Phase 2
0.7098	Intermediate Similarity	NPD7801	Approved
0.7098	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7783	Phase 2
0.7097	Intermediate Similarity	NPD7699	Phase 2
0.7097	Intermediate Similarity	NPD7700	Phase 2
0.7089	Intermediate Similarity	NPD6653	Approved
0.7086	Intermediate Similarity	NPD1608	Approved
0.7083	Intermediate Similarity	NPD8151	Discontinued
0.7075	Intermediate Similarity	NPD9493	Approved
0.7073	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6213	Phase 3
0.7065	Intermediate Similarity	NPD6212	Phase 3
0.7059	Intermediate Similarity	NPD3267	Approved
0.7059	Intermediate Similarity	NPD3266	Approved
0.7055	Intermediate Similarity	NPD2309	Approved
0.7053	Intermediate Similarity	NPD8320	Phase 1
0.7053	Intermediate Similarity	NPD8319	Approved
0.7051	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD920	Approved
0.7048	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7874	Approved
0.7047	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7799	Discontinued
0.7037	Intermediate Similarity	NPD1652	Phase 2
0.7035	Intermediate Similarity	NPD6234	Discontinued
0.703	Intermediate Similarity	NPD2534	Approved
0.703	Intermediate Similarity	NPD2532	Approved
0.703	Intermediate Similarity	NPD2533	Approved
0.7029	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1778	Approved
0.6993	Remote Similarity	NPD3225	Approved
0.6983	Remote Similarity	NPD7240	Approved
0.6974	Remote Similarity	NPD3972	Approved
0.6971	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2861	Phase 2
0.6965	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2651	Approved
0.6964	Remote Similarity	NPD2649	Approved
0.6962	Remote Similarity	NPD1613	Approved
0.6962	Remote Similarity	NPD4307	Phase 2
0.6962	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3496	Discontinued
0.6952	Remote Similarity	NPD8090	Clinical (unspecified phase)

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