NPASS Compound

Structure

CID51404 OpenBabel06191715382D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.2321 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 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 -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 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 -2.5981 2.5000 0.0000 C 0 0 2 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 -2.5981 -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 0 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 20 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 21 1 0 0 0 0 9 14 1 0 0 0 0 10 13 2 0 0 0 0 11 16 1 0 0 0 0 11 17 1 1 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	89.05
Volume:	86.385
LogP:	0.034
LogD:	0.185
LogS:	0.803
# Rotatable Bonds:	2
TPSA:	52.32
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.495
Synthetic Accessibility Score:	2.171
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.457
MDCK Permeability:	0.0008158102282322943
Pgp-inhibitor:	0.0
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999
Plasma Protein Binding (PPB):	9.61272144317627%
Volume Distribution (VD):	0.902
Pgp-substrate:	83.87862396240234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.551
CYP1A2-substrate:	0.509
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.634
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.144
CYP2D6-inhibitor:	0.111
CYP2D6-substrate:	0.384
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	8.787
Half-life (T1/2):	0.446

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.222
AMES Toxicity:	0.905
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.216
Carcinogencity:	0.933
Eye Corrosion:	0.035
Eye Irritation:	0.664
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC51404

Natural Product ID:	NPC51404
*Common Name:**	Heraclenol
IUPAC Name:	9-[(2R)-2,3-dihydroxy-3-methylbutoxy]furo[3,2-g]chromen-7-one
Synonyms:	Heraclenol
Standard InCHIKey:	FOINLJRVEBYARJ-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C16H16O6/c1-16(2,19)11(17)8-21-15-13-10(5-6-20-13)7-9-3-4-12(18)22-14(9)15/h3-7,11,17,19H,8H2,1-2H3/t11-/m1/s1
SMILES:	O=c1ccc2c(o1)c(OC[C@H](C(O)(C)C)O)c1c(c2)cco1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173444
PubChem CID:	73253
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens

*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
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	DOI[10.5012/bkcs.2003.24.11.1699]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[12510838]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15646793]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21657081]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27444348]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31464439]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24758	Angelica dahurica	Species	Apiaceae	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
EC50	1
ED50	1
IC50	1
Others	2
Potency	4

Activity Type	# Activity
Individual Protein	5
NON-MOLECULAR	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	1412.5	nM	PMID[452531]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	23934.1	nM	PMID[452531]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	11.6	nM	PMID[452531]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	100.0	ug ml-1	PMID[452529]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	380.0	nM	PMID[452530]
NPT27	Others	Unspecified		TI	=	870.0	n.a.	PMID[452530]
NPT2	Others	Unspecified		Potency	=	461.1	nM	PMID[452531]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	>	500000.0	nM	PMID[452532]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Inhibition	=	17.2	%	PMID[452532]

☑ 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 NPC51404 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	378
0.1-0.2	1733
0.2-0.3	4383
0.3-0.4	9755
0.4-0.5	8607
0.5-0.6	4127
0.6-0.7	5870
0.7-0.8	5184
0.8-0.85	2221
0.85-0.9	389
0.9-0.95	41
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9693	High Similarity	NPC224165
0.9634	High Similarity	NPC107244
0.9573	High Similarity	NPC53917
0.956	High Similarity	NPC216092
0.9503	High Similarity	NPC173149
0.9503	High Similarity	NPC179015
0.9497	High Similarity	NPC243509
0.9434	High Similarity	NPC33320
0.9325	High Similarity	NPC210460
0.9325	High Similarity	NPC67450
0.9325	High Similarity	NPC193881
0.9325	High Similarity	NPC155264
0.9321	High Similarity	NPC15819
0.9317	High Similarity	NPC14822
0.9277	High Similarity	NPC233956
0.9273	High Similarity	NPC144288
0.9255	High Similarity	NPC49009
0.9255	High Similarity	NPC239270
0.9255	High Similarity	NPC303210
0.9255	High Similarity	NPC95472
0.9202	High Similarity	NPC179464
0.9157	High Similarity	NPC281835
0.9141	High Similarity	NPC234536
0.9141	High Similarity	NPC78612
0.9136	High Similarity	NPC169
0.9012	High Similarity	NPC269495
0.8951	High Similarity	NPC19860
0.8944	High Similarity	NPC131725
0.8938	High Similarity	NPC98028
0.8908	High Similarity	NPC73703
0.8896	High Similarity	NPC78071
0.8855	High Similarity	NPC472582
0.8848	High Similarity	NPC264293
0.8841	High Similarity	NPC187792
0.8837	High Similarity	NPC104682
0.8795	High Similarity	NPC272722
0.8788	High Similarity	NPC328102
0.8773	High Similarity	NPC295608
0.8773	High Similarity	NPC250769
0.8773	High Similarity	NPC278010
0.8758	High Similarity	NPC191104
0.875	High Similarity	NPC323137
0.8743	High Similarity	NPC472625
0.8743	High Similarity	NPC124038
0.8735	High Similarity	NPC349525
0.8721	High Similarity	NPC325176
0.8712	High Similarity	NPC189130
0.8712	High Similarity	NPC475895
0.8706	High Similarity	NPC131866
0.8698	High Similarity	NPC150131
0.8698	High Similarity	NPC186392
0.8698	High Similarity	NPC247973
0.8698	High Similarity	NPC241820
0.8696	High Similarity	NPC88445
0.869	High Similarity	NPC329215
0.869	High Similarity	NPC36320
0.869	High Similarity	NPC204088
0.869	High Similarity	NPC259007
0.8683	High Similarity	NPC471745
0.8683	High Similarity	NPC472635
0.8675	High Similarity	NPC287328
0.8675	High Similarity	NPC472624
0.8675	High Similarity	NPC475784
0.8675	High Similarity	NPC282009
0.8659	High Similarity	NPC279218
0.8659	High Similarity	NPC471746
0.8659	High Similarity	NPC234255
0.8659	High Similarity	NPC108937
0.8655	High Similarity	NPC121333
0.865	High Similarity	NPC60211
0.865	High Similarity	NPC285623
0.865	High Similarity	NPC304954
0.8647	High Similarity	NPC152477
0.8647	High Similarity	NPC165456
0.8639	High Similarity	NPC119589
0.8634	High Similarity	NPC266743
0.8631	High Similarity	NPC65846
0.8623	High Similarity	NPC474038
0.8623	High Similarity	NPC112418
0.8623	High Similarity	NPC74854
0.8623	High Similarity	NPC103201
0.8623	High Similarity	NPC473106
0.8623	High Similarity	NPC471499
0.8623	High Similarity	NPC30655
0.8623	High Similarity	NPC94155
0.8623	High Similarity	NPC45124
0.8614	High Similarity	NPC22192
0.8614	High Similarity	NPC74178
0.8614	High Similarity	NPC250076
0.8614	High Similarity	NPC184755
0.8606	High Similarity	NPC321372
0.8606	High Similarity	NPC129053
0.8606	High Similarity	NPC474609
0.8606	High Similarity	NPC469936
0.8606	High Similarity	NPC109967
0.8606	High Similarity	NPC78554
0.8606	High Similarity	NPC475797
0.8606	High Similarity	NPC472455
0.8606	High Similarity	NPC474738
0.8605	High Similarity	NPC310794
0.8605	High Similarity	NPC62640
0.8605	High Similarity	NPC72455
0.8589	High Similarity	NPC472535
0.8589	High Similarity	NPC474170
0.8589	High Similarity	NPC474388
0.8589	High Similarity	NPC474744
0.8589	High Similarity	NPC472423
0.8589	High Similarity	NPC474772
0.8588	High Similarity	NPC158761
0.858	High Similarity	NPC470457
0.858	High Similarity	NPC45449
0.858	High Similarity	NPC300053
0.858	High Similarity	NPC38914
0.858	High Similarity	NPC108433
0.8571	High Similarity	NPC474034
0.8571	High Similarity	NPC302741
0.8571	High Similarity	NPC219861
0.8571	High Similarity	NPC81679
0.8571	High Similarity	NPC125991
0.8571	High Similarity	NPC117463
0.8571	High Similarity	NPC474033
0.8571	High Similarity	NPC74539
0.8571	High Similarity	NPC193998
0.8571	High Similarity	NPC304443
0.8563	High Similarity	NPC471744
0.8563	High Similarity	NPC119209
0.8563	High Similarity	NPC304839
0.8563	High Similarity	NPC192686
0.8563	High Similarity	NPC220582
0.8563	High Similarity	NPC292415
0.8563	High Similarity	NPC118256
0.8563	High Similarity	NPC470326
0.8554	High Similarity	NPC284820
0.8554	High Similarity	NPC270044
0.8554	High Similarity	NPC474055
0.8554	High Similarity	NPC52530
0.8554	High Similarity	NPC471515
0.8554	High Similarity	NPC108456
0.8554	High Similarity	NPC27337
0.8554	High Similarity	NPC471479
0.8554	High Similarity	NPC52889
0.8554	High Similarity	NPC67876
0.8554	High Similarity	NPC473272
0.8554	High Similarity	NPC472598
0.8554	High Similarity	NPC291508
0.8553	High Similarity	NPC166858
0.8553	High Similarity	NPC51146
0.8547	High Similarity	NPC472584
0.8547	High Similarity	NPC157522
0.8545	High Similarity	NPC472280
0.8545	High Similarity	NPC133392
0.8538	High Similarity	NPC242395
0.8538	High Similarity	NPC288813
0.8537	High Similarity	NPC256141
0.8537	High Similarity	NPC199773
0.8537	High Similarity	NPC237994
0.8537	High Similarity	NPC476238
0.8537	High Similarity	NPC327269
0.8537	High Similarity	NPC40033
0.8537	High Similarity	NPC31627
0.8529	High Similarity	NPC207575
0.8529	High Similarity	NPC471213
0.8529	High Similarity	NPC472895
0.8529	High Similarity	NPC13481
0.8529	High Similarity	NPC173292
0.8528	High Similarity	NPC177839
0.8528	High Similarity	NPC155882
0.8528	High Similarity	NPC472421
0.8528	High Similarity	NPC470908
0.8528	High Similarity	NPC189270
0.8528	High Similarity	NPC5840
0.8521	High Similarity	NPC470459
0.8521	High Similarity	NPC59295
0.8521	High Similarity	NPC263092
0.8521	High Similarity	NPC1706
0.8521	High Similarity	NPC472581
0.8521	High Similarity	NPC1755
0.8521	High Similarity	NPC234004
0.8521	High Similarity	NPC39305
0.8519	High Similarity	NPC261548
0.8512	High Similarity	NPC187354
0.8512	High Similarity	NPC26326
0.8512	High Similarity	NPC474239
0.8512	High Similarity	NPC472632
0.8512	High Similarity	NPC289771
0.8512	High Similarity	NPC34376
0.8512	High Similarity	NPC472634
0.8506	High Similarity	NPC156635
0.8506	High Similarity	NPC8127
0.8506	High Similarity	NPC49667
0.8506	High Similarity	NPC164384
0.8503	High Similarity	NPC113055
0.8503	High Similarity	NPC204879
0.8503	High Similarity	NPC473990
0.8503	High Similarity	NPC195832
0.8497	Intermediate Similarity	NPC261471
0.8497	Intermediate Similarity	NPC277510
0.8497	Intermediate Similarity	NPC65885
0.8494	Intermediate Similarity	NPC282307
0.8494	Intermediate Similarity	NPC278778

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 NPC51404 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	956
0.2-0.3	1961
0.3-0.4	2637
0.4-0.5	1834
0.5-0.6	940
0.6-0.7	334
0.7-0.8	93
0.8-0.85	36
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9434	High Similarity	NPD919	Approved
0.8848	High Similarity	NPD1247	Approved
0.8773	High Similarity	NPD3817	Phase 2
0.872	High Similarity	NPD3882	Suspended
0.8712	High Similarity	NPD7096	Clinical (unspecified phase)
0.865	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD920	Approved
0.8554	High Similarity	NPD7075	Discontinued
0.8553	High Similarity	NPD643	Clinical (unspecified phase)
0.85	High Similarity	NPD6799	Approved
0.8447	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD6559	Discontinued
0.8373	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD3818	Discontinued
0.8365	Intermediate Similarity	NPD1243	Approved
0.8313	Intermediate Similarity	NPD1934	Approved
0.8303	Intermediate Similarity	NPD6599	Discontinued
0.8256	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6166	Phase 2
0.8239	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5494	Approved
0.8218	Intermediate Similarity	NPD5844	Phase 1
0.8198	Intermediate Similarity	NPD3926	Phase 2
0.8155	Intermediate Similarity	NPD2801	Approved
0.8155	Intermediate Similarity	NPD7819	Suspended
0.8136	Intermediate Similarity	NPD7808	Phase 3
0.8125	Intermediate Similarity	NPD6797	Phase 2
0.8121	Intermediate Similarity	NPD5403	Approved
0.811	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5401	Approved
0.8107	Intermediate Similarity	NPD5402	Approved
0.8084	Intermediate Similarity	NPD4380	Phase 2
0.8079	Intermediate Similarity	NPD7251	Discontinued
0.8061	Intermediate Similarity	NPD1512	Approved
0.8011	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7054	Approved
0.7966	Intermediate Similarity	NPD7472	Approved
0.7966	Intermediate Similarity	NPD7074	Phase 3
0.7953	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD2796	Approved
0.7939	Intermediate Similarity	NPD1511	Approved
0.7931	Intermediate Similarity	NPD6232	Discontinued
0.7929	Intermediate Similarity	NPD7411	Suspended
0.7907	Intermediate Similarity	NPD3749	Approved
0.7907	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7473	Discontinued
0.7857	Intermediate Similarity	NPD8434	Phase 2
0.7821	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1549	Phase 2
0.7683	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD2533	Approved
0.7679	Intermediate Similarity	NPD2534	Approved
0.7679	Intermediate Similarity	NPD2532	Approved
0.767	Intermediate Similarity	NPD7199	Phase 2
0.7669	Intermediate Similarity	NPD1510	Phase 2
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.7644	Intermediate Similarity	NPD7768	Phase 2
0.764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1465	Phase 2
0.7622	Intermediate Similarity	NPD1551	Phase 2
0.7593	Intermediate Similarity	NPD447	Suspended
0.759	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2163	Approved
0.7531	Intermediate Similarity	NPD1240	Approved
0.7526	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6959	Discontinued
0.747	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD3751	Discontinued
0.7455	Intermediate Similarity	NPD2799	Discontinued
0.744	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3750	Approved
0.7439	Intermediate Similarity	NPD1607	Approved
0.743	Intermediate Similarity	NPD3787	Discontinued
0.7419	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6190	Approved
0.7394	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2800	Approved
0.7378	Intermediate Similarity	NPD6355	Discontinued
0.7378	Intermediate Similarity	NPD230	Phase 1
0.7371	Intermediate Similarity	NPD37	Approved
0.7365	Intermediate Similarity	NPD2344	Approved
0.7349	Intermediate Similarity	NPD7033	Discontinued
0.7349	Intermediate Similarity	NPD3748	Approved
0.7345	Intermediate Similarity	NPD4965	Approved
0.7345	Intermediate Similarity	NPD4967	Phase 2
0.7345	Intermediate Similarity	NPD4966	Approved
0.7341	Intermediate Similarity	NPD1653	Approved
0.7337	Intermediate Similarity	NPD5953	Discontinued
0.7317	Intermediate Similarity	NPD943	Approved
0.7301	Intermediate Similarity	NPD6798	Discontinued
0.7301	Intermediate Similarity	NPD2313	Discontinued
0.7299	Intermediate Similarity	NPD3226	Approved
0.7284	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6234	Discontinued
0.7263	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7286	Phase 2
0.7225	Intermediate Similarity	NPD5049	Phase 3
0.7204	Intermediate Similarity	NPD6765	Approved
0.7204	Intermediate Similarity	NPD6764	Approved
0.7193	Intermediate Similarity	NPD2309	Approved
0.7193	Intermediate Similarity	NPD2354	Approved
0.7193	Intermediate Similarity	NPD3887	Approved
0.7169	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2346	Discontinued
0.716	Intermediate Similarity	NPD1471	Phase 3
0.7158	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD5710	Approved
0.7135	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3027	Phase 3
0.7125	Intermediate Similarity	NPD9717	Approved
0.7121	Intermediate Similarity	NPD7435	Discontinued
0.7117	Intermediate Similarity	NPD9494	Approved
0.7112	Intermediate Similarity	NPD7685	Pre-registration
0.7108	Intermediate Similarity	NPD1613	Approved
0.7108	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4060	Phase 1
0.7105	Intermediate Similarity	NPD8150	Discontinued
0.7104	Intermediate Similarity	NPD5242	Approved
0.7102	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1203	Approved
0.7095	Intermediate Similarity	NPD5353	Approved
0.7088	Intermediate Similarity	NPD8127	Discontinued
0.7081	Intermediate Similarity	NPD7228	Approved
0.7076	Intermediate Similarity	NPD1652	Phase 2
0.7071	Intermediate Similarity	NPD3057	Approved
0.7065	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4107	Approved
0.7056	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6785	Approved
0.7053	Intermediate Similarity	NPD6784	Approved
0.7049	Intermediate Similarity	NPD6808	Phase 2
0.7048	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD4308	Phase 3
0.7041	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5760	Phase 2
0.7039	Intermediate Similarity	NPD5761	Phase 2
0.7037	Intermediate Similarity	NPD8312	Approved
0.7037	Intermediate Similarity	NPD8313	Approved
0.7031	Intermediate Similarity	NPD4287	Approved
0.7029	Intermediate Similarity	NPD6273	Approved
0.7024	Intermediate Similarity	NPD6651	Approved
0.702	Intermediate Similarity	NPD4482	Phase 3
0.7018	Intermediate Similarity	NPD2424	Discontinued
0.6988	Remote Similarity	NPD411	Approved
0.6988	Remote Similarity	NPD3268	Approved
0.6986	Remote Similarity	NPD7907	Approved
0.6985	Remote Similarity	NPD3533	Approved
0.6985	Remote Similarity	NPD2972	Approved
0.6971	Remote Similarity	NPD4111	Phase 1
0.6971	Remote Similarity	NPD4665	Approved
0.6971	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3146	Approved
0.697	Remote Similarity	NPD6780	Approved
0.697	Remote Similarity	NPD6779	Approved
0.697	Remote Similarity	NPD6778	Approved
0.697	Remote Similarity	NPD6781	Approved
0.697	Remote Similarity	NPD6776	Approved
0.697	Remote Similarity	NPD6782	Approved
0.697	Remote Similarity	NPD6777	Approved
0.6959	Remote Similarity	NPD5763	Approved
0.6959	Remote Similarity	NPD5762	Approved
0.6959	Remote Similarity	NPD2353	Approved
0.6959	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD422	Phase 1
0.6946	Remote Similarity	NPD4062	Phase 3
0.6946	Remote Similarity	NPD8151	Discontinued
0.6944	Remote Similarity	NPD8455	Phase 2
0.6936	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4110	Phase 3
0.6931	Remote Similarity	NPD7240	Approved
0.6931	Remote Similarity	NPD7584	Approved
0.6928	Remote Similarity	NPD7095	Approved
0.6927	Remote Similarity	NPD6386	Approved
0.6927	Remote Similarity	NPD6385	Approved
0.6919	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD1729	Discontinued
0.6914	Remote Similarity	NPD1608	Approved
0.6912	Remote Similarity	NPD7874	Approved
0.6912	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7458	Discontinued

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