NPASS Compound

Structure

NPC216496 OpenBabel07101718282D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 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 3.4641 0.0000 0.0000 C 0 0 0 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 -1.7321 0.0000 0.0000 C 0 0 1 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 -1.7321 1.0000 0.0000 C 0 0 2 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 10 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 1 1 1 0 0 0 9 17 1 0 0 0 0 9 31 1 0 0 0 0 10 24 2 0 0 0 0 10 32 1 0 0 0 0 11 20 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 16 2 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 33 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 28 1 6 0 0 0 18 21 1 0 0 0 0 18 29 2 0 0 0 0 19 22 1 0 0 0 0 19 30 1 1 0 0 0 20 21 2 0 0 0 0 20 33 1 0 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 32 1 1 0 0 0 23 31 1 0 0 0 0 23 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.12
Volume:	445.103
LogP:	2.264
LogD:	1.69
LogS:	-4.549
# Rotatable Bonds:	5
TPSA:	176.12
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.345
Synthetic Accessibility Score:	3.987
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.907
MDCK Permeability:	2.10005346161779e-05
Pgp-inhibitor:	0.103
Pgp-substrate:	0.962
Human Intestinal Absorption (HIA):	0.107
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	90.0933837890625%
Volume Distribution (VD):	0.967
Pgp-substrate:	12.082136154174805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.53
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.258
CYP2C9-substrate:	0.759
CYP2D6-inhibitor:	0.66
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.6
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	2.617
Half-life (T1/2):	0.892

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.675
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.718
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.392
Carcinogencity:	0.105
Eye Corrosion:	0.003
Eye Irritation:	0.186
Respiratory Toxicity:	0.064

Download Data

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

Natural Product: NPC216496

Natural Product ID:	NPC216496
*Common Name:**	Kaempferol-3-O-(2-O-Acetyl-Alpha-L-Rhamnopyranoside)
IUPAC Name:	[(2S,3R,4R,5R,6S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl] acetate
Synonyms:
Standard InCHIKey:	QGPZJURATJCKHO-KNRSITRYSA-N
Standard InCHI:	InChI=1S/C23H22O11/c1-9-17(28)19(30)22(32-10(2)24)23(31-9)34-21-18(29)16-14(27)7-13(26)8-15(16)33-20(21)11-3-5-12(25)6-4-11/h3-9,17,19,22-23,25-28,30H,1-2H3/t9-,17-,19+,22+,23-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O)O)OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469431
PubChem CID:	14861225
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*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
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1080/10575639708043725]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270556]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	59000.0	nM	PMID[462928]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	100000.0	nM	PMID[462928]

☑ 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 NPC216496 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	383
0.1-0.2	1618
0.2-0.3	3850
0.3-0.4	8736
0.4-0.5	9421
0.5-0.6	4761
0.6-0.7	5614
0.7-0.8	5014
0.8-0.85	2175
0.85-0.9	606
0.9-0.95	432
0.95-1	87

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC48093
1.0	High Similarity	NPC224530
1.0	High Similarity	NPC259957
1.0	High Similarity	NPC85707
1.0	High Similarity	NPC129217
1.0	High Similarity	NPC159579
0.9935	High Similarity	NPC27942
0.987	High Similarity	NPC121703
0.9869	High Similarity	NPC282169
0.9868	High Similarity	NPC41121
0.9868	High Similarity	NPC320283
0.9868	High Similarity	NPC104677
0.9868	High Similarity	NPC472459
0.9868	High Similarity	NPC111929
0.9806	High Similarity	NPC72016
0.9803	High Similarity	NPC135391
0.9803	High Similarity	NPC182634
0.9803	High Similarity	NPC77672
0.9803	High Similarity	NPC78263
0.9803	High Similarity	NPC133671
0.9803	High Similarity	NPC54802
0.9803	High Similarity	NPC197304
0.9803	High Similarity	NPC108831
0.9744	High Similarity	NPC64425
0.974	High Similarity	NPC249281
0.974	High Similarity	NPC473438
0.974	High Similarity	NPC163242
0.974	High Similarity	NPC276377
0.974	High Similarity	NPC173582
0.974	High Similarity	NPC253788
0.974	High Similarity	NPC265885
0.974	High Similarity	NPC116458
0.974	High Similarity	NPC476215
0.974	High Similarity	NPC246943
0.974	High Similarity	NPC215710
0.974	High Similarity	NPC139320
0.974	High Similarity	NPC181465
0.9737	High Similarity	NPC323593
0.9737	High Similarity	NPC203500
0.9737	High Similarity	NPC307938
0.9679	High Similarity	NPC139060
0.9679	High Similarity	NPC205824
0.9679	High Similarity	NPC19240
0.9679	High Similarity	NPC129264
0.9679	High Similarity	NPC85751
0.9677	High Similarity	NPC150164
0.9677	High Similarity	NPC240306
0.9675	High Similarity	NPC471079
0.9675	High Similarity	NPC304741
0.9675	High Similarity	NPC153342
0.9675	High Similarity	NPC470405
0.9675	High Similarity	NPC187379
0.9671	High Similarity	NPC27408
0.9671	High Similarity	NPC95090
0.9615	High Similarity	NPC66087
0.9615	High Similarity	NPC80068
0.9615	High Similarity	NPC278419
0.9615	High Similarity	NPC179198
0.9613	High Similarity	NPC297987
0.9613	High Similarity	NPC135846
0.9613	High Similarity	NPC101636
0.9613	High Similarity	NPC470125
0.9613	High Similarity	NPC64305
0.9613	High Similarity	NPC170052
0.9608	High Similarity	NPC127406
0.9605	High Similarity	NPC83283
0.9605	High Similarity	NPC210003
0.9605	High Similarity	NPC143851
0.9605	High Similarity	NPC39360
0.9605	High Similarity	NPC29763
0.956	High Similarity	NPC209550
0.956	High Similarity	NPC116864
0.956	High Similarity	NPC277532
0.956	High Similarity	NPC244776
0.956	High Similarity	NPC175429
0.956	High Similarity	NPC138990
0.9551	High Similarity	NPC298171
0.9551	High Similarity	NPC131745
0.9548	High Similarity	NPC136761
0.9545	High Similarity	NPC44931
0.9545	High Similarity	NPC65003
0.9545	High Similarity	NPC473512
0.9545	High Similarity	NPC60966
0.9545	High Similarity	NPC129827
0.9545	High Similarity	NPC288084
0.9545	High Similarity	NPC6985
0.9545	High Similarity	NPC43638
0.95	High Similarity	NPC175107
0.95	High Similarity	NPC11847
0.95	High Similarity	NPC217822
0.95	High Similarity	NPC101399
0.95	High Similarity	NPC474522
0.95	High Similarity	NPC190003
0.95	High Similarity	NPC221288
0.95	High Similarity	NPC153755
0.9494	High Similarity	NPC256188
0.9494	High Similarity	NPC221342
0.9494	High Similarity	NPC142142
0.9494	High Similarity	NPC203145
0.9494	High Similarity	NPC11432
0.9494	High Similarity	NPC32641
0.9494	High Similarity	NPC476470
0.9494	High Similarity	NPC477613
0.9494	High Similarity	NPC186816
0.9494	High Similarity	NPC189564
0.9494	High Similarity	NPC12013
0.949	High Similarity	NPC183672
0.9487	High Similarity	NPC195685
0.9487	High Similarity	NPC477629
0.9487	High Similarity	NPC270675
0.9487	High Similarity	NPC477628
0.9487	High Similarity	NPC210961
0.9487	High Similarity	NPC472994
0.9484	High Similarity	NPC73511
0.9484	High Similarity	NPC473634
0.9484	High Similarity	NPC138811
0.9484	High Similarity	NPC43761
0.9484	High Similarity	NPC22062
0.9481	High Similarity	NPC206378
0.9477	High Similarity	NPC106625
0.9441	High Similarity	NPC4390
0.9437	High Similarity	NPC470712
0.9437	High Similarity	NPC96605
0.9437	High Similarity	NPC235260
0.9437	High Similarity	NPC20505
0.9437	High Similarity	NPC164704
0.9437	High Similarity	NPC218161
0.9437	High Similarity	NPC469344
0.9437	High Similarity	NPC280642
0.9437	High Similarity	NPC155763
0.9437	High Similarity	NPC188815
0.9434	High Similarity	NPC173637
0.9434	High Similarity	NPC127546
0.9434	High Similarity	NPC52550
0.9434	High Similarity	NPC317489
0.9434	High Similarity	NPC84362
0.9434	High Similarity	NPC223424
0.943	High Similarity	NPC289667
0.943	High Similarity	NPC287889
0.943	High Similarity	NPC135358
0.943	High Similarity	NPC76831
0.943	High Similarity	NPC292929
0.9427	High Similarity	NPC259834
0.9423	High Similarity	NPC473623
0.9419	High Similarity	NPC122809
0.9419	High Similarity	NPC156457
0.9419	High Similarity	NPC161749
0.9419	High Similarity	NPC197896
0.9419	High Similarity	NPC313163
0.9419	High Similarity	NPC258035
0.9416	High Similarity	NPC169248
0.9416	High Similarity	NPC99233
0.9416	High Similarity	NPC97052
0.9416	High Similarity	NPC26195
0.9416	High Similarity	NPC39351
0.9416	High Similarity	NPC72649
0.9412	High Similarity	NPC88484
0.9412	High Similarity	NPC259182
0.9412	High Similarity	NPC259767
0.9412	High Similarity	NPC121001
0.9408	High Similarity	NPC191154
0.9383	High Similarity	NPC264735
0.9379	High Similarity	NPC470716
0.9379	High Similarity	NPC470714
0.9379	High Similarity	NPC470715
0.9375	High Similarity	NPC138927
0.9375	High Similarity	NPC225434
0.9375	High Similarity	NPC219904
0.9375	High Similarity	NPC120099
0.9375	High Similarity	NPC223747
0.9375	High Similarity	NPC203050
0.9375	High Similarity	NPC5319
0.9371	High Similarity	NPC308404
0.9371	High Similarity	NPC276222
0.9371	High Similarity	NPC262222
0.9371	High Similarity	NPC179950
0.9371	High Similarity	NPC145038
0.9371	High Similarity	NPC88789
0.9371	High Similarity	NPC68592
0.9371	High Similarity	NPC113968
0.9371	High Similarity	NPC118284
0.9371	High Similarity	NPC277174
0.9371	High Similarity	NPC73855
0.9371	High Similarity	NPC274618
0.9371	High Similarity	NPC253662
0.9371	High Similarity	NPC56077
0.9371	High Similarity	NPC328940
0.9371	High Similarity	NPC281131
0.9371	High Similarity	NPC135599
0.9371	High Similarity	NPC298666
0.9363	High Similarity	NPC303913
0.9355	High Similarity	NPC261866
0.9355	High Similarity	NPC295613
0.9355	High Similarity	NPC473657
0.9355	High Similarity	NPC45165
0.9355	High Similarity	NPC170475
0.9346	High Similarity	NPC134819
0.9325	High Similarity	NPC471669
0.9325	High Similarity	NPC472385
0.9325	High Similarity	NPC198324

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 NPC216496 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	905
0.2-0.3	1828
0.3-0.4	2644
0.4-0.5	1960
0.5-0.6	974
0.6-0.7	321
0.7-0.8	129
0.8-0.85	26
0.85-0.9	14
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9419	High Similarity	NPD4381	Clinical (unspecified phase)
0.9375	High Similarity	NPD7804	Clinical (unspecified phase)
0.9264	High Similarity	NPD4338	Clinical (unspecified phase)
0.9259	High Similarity	NPD6797	Phase 2
0.9202	High Similarity	NPD7251	Discontinued
0.9146	High Similarity	NPD7808	Phase 3
0.9051	High Similarity	NPD7075	Discontinued
0.9038	High Similarity	NPD6801	Discontinued
0.9018	High Similarity	NPD7054	Approved
0.8963	High Similarity	NPD7472	Approved
0.8961	High Similarity	NPD5403	Approved
0.8889	High Similarity	NPD6799	Approved
0.8861	High Similarity	NPD7096	Clinical (unspecified phase)
0.8848	High Similarity	NPD7074	Phase 3
0.8831	High Similarity	NPD5401	Approved
0.8805	High Similarity	NPD3817	Phase 2
0.879	High Similarity	NPD4380	Phase 2
0.8727	High Similarity	NPD3818	Discontinued
0.8688	High Similarity	NPD5402	Approved
0.8606	High Similarity	NPD6168	Clinical (unspecified phase)
0.8606	High Similarity	NPD6167	Clinical (unspecified phase)
0.8606	High Similarity	NPD6166	Phase 2
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.8553	High Similarity	NPD6599	Discontinued
0.8521	High Similarity	NPD6559	Discontinued
0.85	High Similarity	NPD7411	Suspended
0.8497	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD1934	Approved
0.8442	Intermediate Similarity	NPD1549	Phase 2
0.8395	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD1512	Approved
0.8295	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD3882	Suspended
0.8293	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD2801	Approved
0.8239	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2796	Approved
0.8176	Intermediate Similarity	NPD1511	Approved
0.8171	Intermediate Similarity	NPD7819	Suspended
0.814	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8101	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD3750	Approved
0.7974	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD3751	Discontinued
0.7941	Intermediate Similarity	NPD3787	Discontinued
0.7898	Intermediate Similarity	NPD8312	Approved
0.7898	Intermediate Similarity	NPD8313	Approved
0.7885	Intermediate Similarity	NPD1607	Approved
0.7882	Intermediate Similarity	NPD6959	Discontinued
0.7875	Intermediate Similarity	NPD4628	Phase 3
0.7866	Intermediate Similarity	NPD1653	Approved
0.7862	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7768	Phase 2
0.7849	Intermediate Similarity	NPD7435	Discontinued
0.7848	Intermediate Similarity	NPD1551	Phase 2
0.7844	Intermediate Similarity	NPD8455	Phase 2
0.7819	Intermediate Similarity	NPD7584	Approved
0.7816	Intermediate Similarity	NPD5844	Phase 1
0.7812	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3749	Approved
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6798	Discontinued
0.7733	Intermediate Similarity	NPD6232	Discontinued
0.7719	Intermediate Similarity	NPD5494	Approved
0.7707	Intermediate Similarity	NPD1933	Approved
0.7701	Intermediate Similarity	NPD7473	Discontinued
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6233	Phase 2
0.7688	Intermediate Similarity	NPD6776	Approved
0.7688	Intermediate Similarity	NPD6779	Approved
0.7688	Intermediate Similarity	NPD6781	Approved
0.7688	Intermediate Similarity	NPD6782	Approved
0.7688	Intermediate Similarity	NPD6778	Approved
0.7688	Intermediate Similarity	NPD6777	Approved
0.7688	Intermediate Similarity	NPD6780	Approved
0.7684	Intermediate Similarity	NPD7685	Pre-registration
0.7674	Intermediate Similarity	NPD7199	Phase 2
0.7673	Intermediate Similarity	NPD7033	Discontinued
0.7673	Intermediate Similarity	NPD3748	Approved
0.7661	Intermediate Similarity	NPD919	Approved
0.7633	Intermediate Similarity	NPD1465	Phase 2
0.7613	Intermediate Similarity	NPD6832	Phase 2
0.7604	Intermediate Similarity	NPD7874	Approved
0.7604	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1652	Phase 2
0.7592	Intermediate Similarity	NPD7585	Approved
0.759	Intermediate Similarity	NPD920	Approved
0.7557	Intermediate Similarity	NPD7228	Approved
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7539	Intermediate Similarity	NPD7583	Approved
0.7532	Intermediate Similarity	NPD1203	Approved
0.7528	Intermediate Similarity	NPD5953	Discontinued
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7485	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD5124	Phase 1
0.7484	Intermediate Similarity	NPD6355	Discontinued
0.7484	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7697	Approved
0.7474	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7698	Approved
0.7474	Intermediate Similarity	NPD7783	Phase 2
0.7474	Intermediate Similarity	NPD7696	Phase 3
0.7471	Intermediate Similarity	NPD37	Approved
0.747	Intermediate Similarity	NPD2534	Approved
0.747	Intermediate Similarity	NPD2532	Approved
0.747	Intermediate Similarity	NPD2533	Approved
0.747	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7266	Discontinued
0.7457	Intermediate Similarity	NPD6234	Discontinued
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4966	Approved
0.7442	Intermediate Similarity	NPD4967	Phase 2
0.7442	Intermediate Similarity	NPD4965	Approved
0.7435	Intermediate Similarity	NPD8319	Approved
0.7435	Intermediate Similarity	NPD8320	Phase 1
0.7435	Intermediate Similarity	NPD7871	Phase 2
0.7435	Intermediate Similarity	NPD7870	Phase 2
0.7419	Intermediate Similarity	NPD6534	Approved
0.7419	Intermediate Similarity	NPD6535	Approved
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7701	Phase 2
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7405	Intermediate Similarity	NPD3268	Approved
0.7391	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD422	Phase 1
0.7378	Intermediate Similarity	NPD2800	Approved
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7371	Intermediate Similarity	NPD1247	Approved
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4062	Phase 3
0.7355	Intermediate Similarity	NPD3225	Approved
0.7348	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2799	Discontinued
0.7338	Intermediate Similarity	NPD9717	Approved
0.7329	Intermediate Similarity	NPD6651	Approved
0.7326	Intermediate Similarity	NPD4363	Phase 3
0.7326	Intermediate Similarity	NPD4360	Phase 2
0.7312	Intermediate Similarity	NPD1613	Approved
0.7312	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2797	Approved
0.7302	Intermediate Similarity	NPD7700	Phase 2
0.7302	Intermediate Similarity	NPD7699	Phase 2
0.7296	Intermediate Similarity	NPD7801	Approved
0.7294	Intermediate Similarity	NPD3226	Approved
0.7289	Intermediate Similarity	NPD3887	Approved
0.7289	Intermediate Similarity	NPD2354	Approved
0.7288	Intermediate Similarity	NPD3926	Phase 2
0.7283	Intermediate Similarity	NPD8150	Discontinued
0.7278	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD230	Phase 1
0.7267	Intermediate Similarity	NPD4340	Discontinued
0.7261	Intermediate Similarity	NPD2798	Approved
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7237	Intermediate Similarity	NPD1548	Phase 1
0.7228	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7240	Approved
0.7188	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7097	Phase 1
0.716	Intermediate Similarity	NPD447	Suspended
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2346	Discontinued
0.7152	Intermediate Similarity	NPD2344	Approved
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD9545	Approved
0.7118	Intermediate Similarity	NPD5049	Phase 3
0.7099	Intermediate Similarity	NPD943	Approved
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7093	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6100	Approved
0.7091	Intermediate Similarity	NPD6099	Approved
0.7089	Intermediate Similarity	NPD3266	Approved
0.7089	Intermediate Similarity	NPD3267	Approved
0.7086	Intermediate Similarity	NPD4288	Approved
0.7069	Intermediate Similarity	NPD6844	Discontinued
0.7063	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1610	Phase 2
0.7048	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2353	Approved
0.7044	Intermediate Similarity	NPD1019	Discontinued
0.7039	Intermediate Similarity	NPD5710	Approved
0.7039	Intermediate Similarity	NPD5711	Approved
0.7019	Intermediate Similarity	NPD3027	Phase 3
0.7015	Intermediate Similarity	NPD7930	Approved
0.7011	Intermediate Similarity	NPD5889	Approved
0.7011	Intermediate Similarity	NPD5890	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