NPASS Compound

Structure

CID193881 OpenBabel06191715582D 27 29 0 0 0 0 0 0 0 0999 V2000 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 -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 -2.5981 2.5000 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 -2.5981 1.5000 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 -6.0622 4.5000 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 -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 0.8660 -0.5000 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 -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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 15 2 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 26 1 0 0 0 0 13 25 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 20 2 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 20 22 1 0 0 0 0 20 25 1 0 0 0 0 21 22 2 0 0 0 0 21 27 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.16
Volume:	386.258
LogP:	5.531
LogD:	4.36
LogS:	-5.519
# Rotatable Bonds:	7
TPSA:	61.81
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	2.984
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.728
MDCK Permeability:	1.8382548660156317e-05
Pgp-inhibitor:	0.224
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	85.14448547363281%
Volume Distribution (VD):	0.606
Pgp-substrate:	15.683843612670898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.427
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.919
CYP2C9-substrate:	0.797
CYP2D6-inhibitor:	0.728
CYP2D6-substrate:	0.679
CYP3A4-inhibitor:	0.655
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	12.157
Half-life (T1/2):	0.173

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.875
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.102
Skin Sensitization:	0.358
Carcinogencity:	0.247
Eye Corrosion:	0.003
Eye Irritation:	0.097
Respiratory Toxicity:	0.712

Download Data

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

Natural Product: NPC193881

Natural Product ID:	NPC193881
*Common Name:**	8-Geranyloxy-5-Methoxypsoralen
IUPAC Name:	9-[(2E)-3,7-dimethylocta-2,6-dienoxy]-4-methoxyfuro[3,2-g]chromen-7-one
Synonyms:
Standard InCHIKey:	CTPXXQMJFXTTQZ-XNTDXEJSSA-N
Standard InCHI:	InChI=1S/C22H24O5/c1-14(2)6-5-7-15(3)10-12-26-22-20-17(11-13-25-20)19(24-4)16-8-9-18(23)27-21(16)22/h6,8-11,13H,5,7,12H2,1-4H3/b15-10+
SMILES:	COc1c2ccoc2c(c2c1ccc(=O)o2)OC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934197
PubChem CID:	6442182
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 [CHEMONTID:0002832] 5-methoxypsoralens

*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]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
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]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2392	Hansenia weberbaueriana	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]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	11100.0	nM	PMID[555584]

☑ 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 NPC193881 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	473
0.1-0.2	2008
0.2-0.3	5196
0.3-0.4	11134
0.4-0.5	6727
0.5-0.6	4273
0.6-0.7	5890
0.7-0.8	5099
0.8-0.85	1522
0.85-0.9	314
0.9-0.95	44
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC67450
1.0	High Similarity	NPC210460
1.0	High Similarity	NPC155264
0.9872	High Similarity	NPC179464
0.9808	High Similarity	NPC234536
0.9808	High Similarity	NPC78612
0.9744	High Similarity	NPC216092
0.9688	High Similarity	NPC144288
0.9679	High Similarity	NPC243509
0.9615	High Similarity	NPC33320
0.9571	High Similarity	NPC107244
0.9509	High Similarity	NPC224165
0.9509	High Similarity	NPC53917
0.9494	High Similarity	NPC264293
0.9448	High Similarity	NPC233956
0.9437	High Similarity	NPC173149
0.9437	High Similarity	NPC179015
0.9325	High Similarity	NPC51404
0.9325	High Similarity	NPC281835
0.9255	High Similarity	NPC65846
0.9212	High Similarity	NPC72455
0.9167	High Similarity	NPC191104
0.9114	High Similarity	NPC186507
0.9108	High Similarity	NPC98028
0.9103	High Similarity	NPC88445
0.9057	High Similarity	NPC276059
0.9057	High Similarity	NPC241774
0.9057	High Similarity	NPC34725
0.9057	High Similarity	NPC122623
0.9018	High Similarity	NPC15819
0.9006	High Similarity	NPC250076
0.9	High Similarity	NPC257277
0.8982	High Similarity	NPC62640
0.8974	High Similarity	NPC304443
0.8974	High Similarity	NPC74539
0.8944	High Similarity	NPC19097
0.8938	High Similarity	NPC278010
0.8938	High Similarity	NPC250769
0.8938	High Similarity	NPC295608
0.8922	High Similarity	NPC475964
0.8896	High Similarity	NPC14822
0.8875	High Similarity	NPC131725
0.8868	High Similarity	NPC474170
0.8868	High Similarity	NPC472535
0.8868	High Similarity	NPC474388
0.8862	High Similarity	NPC190351
0.8861	High Similarity	NPC69752
0.8854	High Similarity	NPC117463
0.8848	High Similarity	NPC187923
0.8848	High Similarity	NPC36320
0.8846	High Similarity	NPC246903
0.8844	High Similarity	NPC73703
0.8834	High Similarity	NPC95472
0.8834	High Similarity	NPC239270
0.8834	High Similarity	NPC169
0.8834	High Similarity	NPC303210
0.8834	High Similarity	NPC49009
0.8827	High Similarity	NPC269495
0.882	High Similarity	NPC471746
0.882	High Similarity	NPC233776
0.8805	High Similarity	NPC177839
0.8805	High Similarity	NPC201547
0.8805	High Similarity	NPC259058
0.8802	High Similarity	NPC41853
0.8797	High Similarity	NPC266743
0.8795	High Similarity	NPC472895
0.8788	High Similarity	NPC132054
0.8773	High Similarity	NPC257914
0.8773	High Similarity	NPC238405
0.8773	High Similarity	NPC104459
0.8758	High Similarity	NPC128961
0.8758	High Similarity	NPC472408
0.8758	High Similarity	NPC41719
0.8757	High Similarity	NPC65885
0.875	High Similarity	NPC198615
0.875	High Similarity	NPC474663
0.8743	High Similarity	NPC167479
0.8743	High Similarity	NPC247973
0.8742	High Similarity	NPC181250
0.8735	High Similarity	NPC280893
0.8735	High Similarity	NPC45449
0.8734	High Similarity	NPC299923
0.8734	High Similarity	NPC205522
0.8727	High Similarity	NPC18284
0.8727	High Similarity	NPC273021
0.8727	High Similarity	NPC302741
0.8727	High Similarity	NPC272722
0.8726	High Similarity	NPC208584
0.872	High Similarity	NPC298093
0.8718	High Similarity	NPC51146
0.8718	High Similarity	NPC166858
0.8718	High Similarity	NPC313036
0.8706	High Similarity	NPC66804
0.8704	High Similarity	NPC284353
0.8704	High Similarity	NPC478238
0.8696	High Similarity	NPC38361
0.8696	High Similarity	NPC166201
0.8696	High Similarity	NPC130015
0.8688	High Similarity	NPC29056
0.8683	High Similarity	NPC298071
0.8683	High Similarity	NPC323137
0.8679	High Similarity	NPC63256
0.8679	High Similarity	NPC10304
0.8675	High Similarity	NPC1755
0.8675	High Similarity	NPC263092
0.8675	High Similarity	NPC1706
0.8675	High Similarity	NPC39305
0.8675	High Similarity	NPC59295
0.8671	High Similarity	NPC216314
0.8671	High Similarity	NPC110639
0.8671	High Similarity	NPC106461
0.8671	High Similarity	NPC215932
0.8671	High Similarity	NPC120924
0.8671	High Similarity	NPC310259
0.8671	High Similarity	NPC40818
0.8671	High Similarity	NPC190572
0.8671	High Similarity	NPC195919
0.8671	High Similarity	NPC14958
0.8659	High Similarity	NPC15764
0.8659	High Similarity	NPC195832
0.8655	High Similarity	NPC8127
0.8655	High Similarity	NPC49667
0.8654	High Similarity	NPC27220
0.865	High Similarity	NPC45131
0.865	High Similarity	NPC180340
0.865	High Similarity	NPC248299
0.8647	High Similarity	NPC261471
0.8647	High Similarity	NPC310794
0.8642	High Similarity	NPC279930
0.8642	High Similarity	NPC478213
0.8639	High Similarity	NPC476641
0.8639	High Similarity	NPC131866
0.8634	High Similarity	NPC473732
0.8631	High Similarity	NPC241820
0.8625	High Similarity	NPC238366
0.8625	High Similarity	NPC474648
0.8623	High Similarity	NPC475369
0.8623	High Similarity	NPC279768
0.8616	High Similarity	NPC85233
0.8614	High Similarity	NPC81679
0.8614	High Similarity	NPC312056
0.8614	High Similarity	NPC108767
0.8614	High Similarity	NPC84515
0.8614	High Similarity	NPC193998
0.8614	High Similarity	NPC238995
0.8608	High Similarity	NPC136278
0.8608	High Similarity	NPC471590
0.8606	High Similarity	NPC131557
0.8606	High Similarity	NPC477164
0.8606	High Similarity	NPC139876
0.8606	High Similarity	NPC246478
0.8605	High Similarity	NPC297807
0.8605	High Similarity	NPC98546
0.8598	High Similarity	NPC270044
0.8598	High Similarity	NPC258644
0.8598	High Similarity	NPC310206
0.8598	High Similarity	NPC476981
0.8596	High Similarity	NPC287243
0.8589	High Similarity	NPC189960
0.8589	High Similarity	NPC32557
0.8588	High Similarity	NPC157522
0.858	High Similarity	NPC475116
0.858	High Similarity	NPC148497
0.858	High Similarity	NPC292460
0.858	High Similarity	NPC134677
0.858	High Similarity	NPC40033
0.858	High Similarity	NPC60211
0.858	High Similarity	NPC211309
0.858	High Similarity	NPC68882
0.858	High Similarity	NPC152477
0.858	High Similarity	NPC153008
0.858	High Similarity	NPC280493
0.8571	High Similarity	NPC148423
0.8571	High Similarity	NPC189270
0.8571	High Similarity	NPC5840
0.8571	High Similarity	NPC155882
0.8571	High Similarity	NPC135303
0.8571	High Similarity	NPC277480
0.8563	High Similarity	NPC470459
0.8562	High Similarity	NPC476342
0.8562	High Similarity	NPC183236
0.8554	High Similarity	NPC165549
0.8554	High Similarity	NPC296540
0.8554	High Similarity	NPC309335
0.8554	High Similarity	NPC34376
0.8554	High Similarity	NPC188486
0.8553	High Similarity	NPC231013
0.8553	High Similarity	NPC302408
0.8553	High Similarity	NPC283002
0.8547	High Similarity	NPC164384
0.8545	High Similarity	NPC196879
0.8545	High Similarity	NPC113055
0.8545	High Similarity	NPC16935
0.8544	High Similarity	NPC182842
0.8544	High Similarity	NPC23955
0.8544	High Similarity	NPC113089
0.8538	High Similarity	NPC181523
0.8538	High Similarity	NPC216842
0.8538	High Similarity	NPC82217
0.8538	High Similarity	NPC476640

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 NPC193881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	1030
0.2-0.3	1999
0.3-0.4	2732
0.4-0.5	1712
0.5-0.6	858
0.6-0.7	287
0.7-0.8	102
0.8-0.85	16
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9615	High Similarity	NPD919	Approved
0.9494	High Similarity	NPD1247	Approved
0.8974	High Similarity	NPD920	Approved
0.8846	High Similarity	NPD642	Clinical (unspecified phase)
0.872	High Similarity	NPD5494	Approved
0.8718	High Similarity	NPD643	Clinical (unspecified phase)
0.8704	High Similarity	NPD3817	Phase 2
0.8537	High Similarity	NPD3882	Suspended
0.8526	High Similarity	NPD1243	Approved
0.8452	Intermediate Similarity	NPD3926	Phase 2
0.8313	Intermediate Similarity	NPD6799	Approved
0.8303	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD2801	Approved
0.8242	Intermediate Similarity	NPD6801	Discontinued
0.8171	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7075	Discontinued
0.815	Intermediate Similarity	NPD5844	Phase 1
0.8144	Intermediate Similarity	NPD5402	Approved
0.8121	Intermediate Similarity	NPD6599	Discontinued
0.8092	Intermediate Similarity	NPD3818	Discontinued
0.8084	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD1934	Approved
0.8011	Intermediate Similarity	NPD6559	Discontinued
0.7987	Intermediate Similarity	NPD2796	Approved
0.7976	Intermediate Similarity	NPD7819	Suspended
0.7965	Intermediate Similarity	NPD6232	Discontinued
0.7939	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7473	Discontinued
0.7879	Intermediate Similarity	NPD1512	Approved
0.7874	Intermediate Similarity	NPD6166	Phase 2
0.7874	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7808	Phase 3
0.7758	Intermediate Similarity	NPD1511	Approved
0.7753	Intermediate Similarity	NPD6797	Phase 2
0.7751	Intermediate Similarity	NPD7411	Suspended
0.7733	Intermediate Similarity	NPD3749	Approved
0.7725	Intermediate Similarity	NPD5403	Approved
0.7711	Intermediate Similarity	NPD2534	Approved
0.7711	Intermediate Similarity	NPD2533	Approved
0.7711	Intermediate Similarity	NPD2532	Approved
0.7711	Intermediate Similarity	NPD5401	Approved
0.7709	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD4380	Phase 2
0.7654	Intermediate Similarity	NPD2935	Discontinued
0.764	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7054	Approved
0.7625	Intermediate Similarity	NPD447	Suspended
0.7598	Intermediate Similarity	NPD7472	Approved
0.7598	Intermediate Similarity	NPD7074	Phase 3
0.7596	Intermediate Similarity	NPD8434	Phase 2
0.7558	Intermediate Similarity	NPD1465	Phase 2
0.7556	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1510	Phase 2
0.7485	Intermediate Similarity	NPD3748	Approved
0.7472	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7768	Phase 2
0.7455	Intermediate Similarity	NPD1549	Phase 2
0.7455	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1551	Phase 2
0.7421	Intermediate Similarity	NPD6832	Phase 2
0.7419	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5242	Approved
0.741	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2800	Approved
0.7407	Intermediate Similarity	NPD1933	Approved
0.7407	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1471	Phase 3
0.7394	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2799	Discontinued
0.7374	Intermediate Similarity	NPD2403	Approved
0.7346	Intermediate Similarity	NPD1240	Approved
0.734	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2313	Discontinued
0.7326	Intermediate Similarity	NPD3226	Approved
0.7314	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5353	Approved
0.7303	Intermediate Similarity	NPD7199	Phase 2
0.7303	Intermediate Similarity	NPD6959	Discontinued
0.7301	Intermediate Similarity	NPD230	Phase 1
0.7289	Intermediate Similarity	NPD2344	Approved
0.7268	Intermediate Similarity	NPD5953	Discontinued
0.7262	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3750	Approved
0.7258	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1607	Approved
0.7253	Intermediate Similarity	NPD7286	Phase 2
0.7241	Intermediate Similarity	NPD6385	Approved
0.7241	Intermediate Similarity	NPD6386	Approved
0.7235	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD37	Approved
0.7198	Intermediate Similarity	NPD3751	Discontinued
0.7198	Intermediate Similarity	NPD2163	Approved
0.7186	Intermediate Similarity	NPD2346	Discontinued
0.7182	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4967	Phase 2
0.7175	Intermediate Similarity	NPD4966	Approved
0.7175	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD1653	Approved
0.7167	Intermediate Similarity	NPD3787	Discontinued
0.7167	Intermediate Similarity	NPD6808	Phase 2
0.7167	Intermediate Similarity	NPD5711	Approved
0.7167	Intermediate Similarity	NPD5710	Approved
0.7167	Intermediate Similarity	NPD7229	Phase 3
0.716	Intermediate Similarity	NPD4628	Phase 3
0.7134	Intermediate Similarity	NPD943	Approved
0.7118	Intermediate Similarity	NPD2309	Approved
0.7118	Intermediate Similarity	NPD6190	Approved
0.7118	Intermediate Similarity	NPD3887	Approved
0.7098	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6234	Discontinued
0.7093	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3146	Approved
0.7081	Intermediate Similarity	NPD1019	Discontinued
0.7077	Intermediate Similarity	NPD4107	Approved
0.7052	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4482	Phase 3
0.7012	Intermediate Similarity	NPD1296	Phase 2
0.7006	Intermediate Similarity	NPD6279	Approved
0.7006	Intermediate Similarity	NPD6280	Approved
0.7005	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2654	Approved
0.699	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6355	Discontinued
0.6982	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2353	Approved
0.697	Remote Similarity	NPD6233	Phase 2
0.697	Remote Similarity	NPD7435	Discontinued
0.6964	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD9717	Approved
0.6933	Remote Similarity	NPD9494	Approved
0.6928	Remote Similarity	NPD4307	Phase 2
0.6914	Remote Similarity	NPD3266	Approved
0.6914	Remote Similarity	NPD3267	Approved
0.6914	Remote Similarity	NPD1203	Approved
0.6909	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6798	Discontinued
0.6875	Remote Similarity	NPD4287	Approved
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7033	Discontinued
0.6862	Remote Similarity	NPD6764	Approved
0.6862	Remote Similarity	NPD6765	Approved
0.686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8150	Discontinued
0.6857	Remote Similarity	NPD5049	Phase 3
0.6855	Remote Similarity	NPD17	Approved
0.6854	Remote Similarity	NPD5890	Approved
0.6854	Remote Similarity	NPD5889	Approved
0.6845	Remote Similarity	NPD6651	Approved
0.6842	Remote Similarity	NPD7907	Approved
0.6834	Remote Similarity	NPD5005	Approved
0.6834	Remote Similarity	NPD5006	Approved
0.6831	Remote Similarity	NPD8127	Discontinued
0.6828	Remote Similarity	NPD7228	Approved
0.6826	Remote Similarity	NPD4060	Phase 1
0.6825	Remote Similarity	NPD7549	Discontinued
0.6821	Remote Similarity	NPD2354	Approved
0.6818	Remote Similarity	NPD6782	Approved
0.6818	Remote Similarity	NPD6780	Approved
0.6818	Remote Similarity	NPD6777	Approved
0.6818	Remote Similarity	NPD6776	Approved
0.6818	Remote Similarity	NPD6779	Approved
0.6818	Remote Similarity	NPD6781	Approved
0.6818	Remote Similarity	NPD6778	Approved
0.6807	Remote Similarity	NPD411	Approved
0.6807	Remote Similarity	NPD3268	Approved
0.68	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8313	Approved
0.6789	Remote Similarity	NPD8312	Approved
0.6786	Remote Similarity	NPD5124	Phase 1
0.6786	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5761	Phase 2
0.6778	Remote Similarity	NPD5760	Phase 2
0.6772	Remote Similarity	NPD5536	Phase 2
0.6772	Remote Similarity	NPD7685	Pre-registration
0.677	Remote Similarity	NPD422	Phase 1
0.6768	Remote Similarity	NPD8285	Discontinued
0.6768	Remote Similarity	NPD2798	Approved
0.6765	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4308	Phase 3
0.6765	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7874	Approved
0.676	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1729	Discontinued
0.6747	Remote Similarity	NPD3027	Phase 3
0.6746	Remote Similarity	NPD4111	Phase 1
0.6746	Remote Similarity	NPD4665	Approved
0.6742	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6742	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