NPASS Compound

Structure

NPC306835 OpenBabel07101719142D 26 27 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 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 -3.4641 -3.0000 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 -2.5981 2.5000 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 -1.5000 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 -2.5981 -0.5000 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 -3.4641 -2.0000 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 1.7321 -0.0000 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 -1.7321 0.0000 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 0.8660 -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 -0.0000 -0.0000 0.0000 C 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 1.7321 1.0000 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 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 4 1 0 0 0 0 2 11 1 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 5 17 1 0 0 0 0 6 9 1 0 0 0 0 6 11 2 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 23 2 0 0 0 0 16 9 1 1 0 0 0 16 26 1 0 0 0 0 17 24 2 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.14
Volume:	369.013
LogP:	5.215
LogD:	3.239
LogS:	-3.224
# Rotatable Bonds:	6
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	3.29
Fsp3:	0.25
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:	-5.074
MDCK Permeability:	2.5179147996823303e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.596
Human Intestinal Absorption (HIA):	0.124
20% Bioavailability (F20%):	0.96
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	99.14154815673828%
Volume Distribution (VD):	0.419
Pgp-substrate:	2.4906747341156006%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.653
CYP2C19-inhibitor:	0.556
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.839
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.78
CYP2D6-substrate:	0.664
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	4.719
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.656
AMES Toxicity:	0.717
Rat Oral Acute Toxicity:	0.357
Maximum Recommended Daily Dose:	0.429
Skin Sensitization:	0.951
Carcinogencity:	0.37
Eye Corrosion:	0.633
Eye Irritation:	0.931
Respiratory Toxicity:	0.311

Download Data

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

Natural Product: NPC306835

Natural Product ID:	NPC306835
*Common Name:**	[(1R)-1-(5,8-Dihydroxy-1,4-Dioxonaphthalen-2-Yl)-4-Methylpent-3-Enyl] Butanoate
IUPAC Name:	[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] butanoate
Synonyms:
Standard InCHIKey:	FMXUZLUFNDEQPM-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C20H22O6/c1-4-5-17(24)26-16(9-6-11(2)3)12-10-15(23)18-13(21)7-8-14(22)19(18)20(12)25/h6-8,10,16,21-22H,4-5,9H2,1-3H3/t16-/m1/s1
SMILES:	CCCC(=O)O[C@H](CC=C(C)C)C1=CC(=O)c2c(ccc(c2C1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL8806
PubChem CID:	10089766
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1007/s11418-007-0221-0]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17157006]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19217780]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3373224]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	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	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	IC50	=	144000.0	nM	PMID[496044]
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	IC50	=	77600.0	nM	PMID[496045]
NPT2584	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 2	Homo sapiens	IC50	=	49600.0	nM	PMID[496045]

☑ 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 NPC306835 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	300
0.1-0.2	1242
0.2-0.3	2942
0.3-0.4	6832
0.4-0.5	11407
0.5-0.6	4856
0.6-0.7	8411
0.7-0.8	6162
0.8-0.85	449
0.85-0.9	64
0.9-0.95	10
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471602
1.0	High Similarity	NPC299405
1.0	High Similarity	NPC216312
1.0	High Similarity	NPC29771
1.0	High Similarity	NPC256463
1.0	High Similarity	NPC476477
1.0	High Similarity	NPC111422
0.9925	High Similarity	NPC37992
0.9925	High Similarity	NPC241349
0.9925	High Similarity	NPC42262
0.9925	High Similarity	NPC220496
0.9925	High Similarity	NPC32749
0.9925	High Similarity	NPC147542
0.9925	High Similarity	NPC327916
0.9851	High Similarity	NPC257003
0.9851	High Similarity	NPC471444
0.9778	High Similarity	NPC474300
0.9706	High Similarity	NPC476473
0.9635	High Similarity	NPC274085
0.9635	High Similarity	NPC89664
0.9556	High Similarity	NPC295339
0.9481	High Similarity	NPC61590
0.9353	High Similarity	NPC103910
0.9323	High Similarity	NPC110609
0.9323	High Similarity	NPC242358
0.9323	High Similarity	NPC246693
0.9281	High Similarity	NPC21873
0.9015	High Similarity	NPC306765
0.8978	High Similarity	NPC281513
0.8978	High Similarity	NPC22222
0.8944	High Similarity	NPC477409
0.8841	High Similarity	NPC27407
0.8714	High Similarity	NPC305060
0.8705	High Similarity	NPC142027
0.8699	High Similarity	NPC94781
0.869	High Similarity	NPC147250
0.8686	High Similarity	NPC7012
0.8662	High Similarity	NPC315578
0.8647	High Similarity	NPC477153
0.8639	High Similarity	NPC120171
0.8639	High Similarity	NPC280753
0.8639	High Similarity	NPC44378
0.863	High Similarity	NPC119767
0.8623	High Similarity	NPC477406
0.8621	High Similarity	NPC474630
0.8621	High Similarity	NPC474309
0.8621	High Similarity	NPC475923
0.8609	High Similarity	NPC29552
0.8601	High Similarity	NPC124365
0.8593	High Similarity	NPC3224
0.8593	High Similarity	NPC231774
0.8593	High Similarity	NPC1991
0.8592	High Similarity	NPC26924
0.8592	High Similarity	NPC103337
0.8592	High Similarity	NPC114620
0.8592	High Similarity	NPC477408
0.8561	High Similarity	NPC43627
0.8552	High Similarity	NPC42540
0.8552	High Similarity	NPC151607
0.8551	High Similarity	NPC205992
0.8551	High Similarity	NPC470831
0.8551	High Similarity	NPC214702
0.854	High Similarity	NPC278928
0.8533	High Similarity	NPC182921
0.8533	High Similarity	NPC218870
0.8533	High Similarity	NPC474824
0.8533	High Similarity	NPC470408
0.8529	High Similarity	NPC471530
0.8521	High Similarity	NPC191835
0.8521	High Similarity	NPC221104
0.8521	High Similarity	NPC33144
0.8521	High Similarity	NPC197666
0.8521	High Similarity	NPC126739
0.8521	High Similarity	NPC478200
0.8516	High Similarity	NPC474301
0.8511	High Similarity	NPC291454
0.8511	High Similarity	NPC272268
0.8511	High Similarity	NPC141934
0.85	High Similarity	NPC474097
0.8489	Intermediate Similarity	NPC309430
0.8485	Intermediate Similarity	NPC206778
0.8485	Intermediate Similarity	NPC285829
0.8483	Intermediate Similarity	NPC471731
0.8483	Intermediate Similarity	NPC478202
0.8483	Intermediate Similarity	NPC159721
0.8478	Intermediate Similarity	NPC475741
0.8477	Intermediate Similarity	NPC66029
0.8472	Intermediate Similarity	NPC130485
0.8472	Intermediate Similarity	NPC478217
0.8472	Intermediate Similarity	NPC472035
0.8472	Intermediate Similarity	NPC470842
0.8472	Intermediate Similarity	NPC478201
0.8472	Intermediate Similarity	NPC313123
0.8472	Intermediate Similarity	NPC472603
0.8472	Intermediate Similarity	NPC283292
0.8472	Intermediate Similarity	NPC149533
0.8467	Intermediate Similarity	NPC281272
0.8467	Intermediate Similarity	NPC165257
0.8467	Intermediate Similarity	NPC237225
0.8462	Intermediate Similarity	NPC1268
0.8456	Intermediate Similarity	NPC227741
0.8456	Intermediate Similarity	NPC295202
0.8456	Intermediate Similarity	NPC96915
0.8456	Intermediate Similarity	NPC315520
0.8456	Intermediate Similarity	NPC136342
0.8456	Intermediate Similarity	NPC49647
0.8451	Intermediate Similarity	NPC70380
0.8451	Intermediate Similarity	NPC71256
0.8451	Intermediate Similarity	NPC245923
0.8446	Intermediate Similarity	NPC470479
0.8444	Intermediate Similarity	NPC310540
0.8444	Intermediate Similarity	NPC234890
0.8444	Intermediate Similarity	NPC74507
0.844	Intermediate Similarity	NPC161632
0.8435	Intermediate Similarity	NPC300540
0.8433	Intermediate Similarity	NPC307174
0.8425	Intermediate Similarity	NPC210966
0.8425	Intermediate Similarity	NPC126882
0.8425	Intermediate Similarity	NPC478203
0.8421	Intermediate Similarity	NPC474861
0.8421	Intermediate Similarity	NPC472050
0.8421	Intermediate Similarity	NPC478027
0.8414	Intermediate Similarity	NPC329493
0.8414	Intermediate Similarity	NPC471733
0.8411	Intermediate Similarity	NPC477691
0.8411	Intermediate Similarity	NPC474621
0.8411	Intermediate Similarity	NPC474622
0.8409	Intermediate Similarity	NPC232178
0.8403	Intermediate Similarity	NPC472601
0.8403	Intermediate Similarity	NPC156872
0.8403	Intermediate Similarity	NPC472600
0.84	Intermediate Similarity	NPC39819
0.8394	Intermediate Similarity	NPC45537
0.8392	Intermediate Similarity	NPC212693
0.8392	Intermediate Similarity	NPC472602
0.8392	Intermediate Similarity	NPC9121
0.8392	Intermediate Similarity	NPC177307
0.8392	Intermediate Similarity	NPC94248
0.8392	Intermediate Similarity	NPC173980
0.8382	Intermediate Similarity	NPC103540
0.8382	Intermediate Similarity	NPC287473
0.8382	Intermediate Similarity	NPC240744
0.8382	Intermediate Similarity	NPC167055
0.8382	Intermediate Similarity	NPC131799
0.838	Intermediate Similarity	NPC474813
0.8369	Intermediate Similarity	NPC288089
0.8367	Intermediate Similarity	NPC257558
0.8367	Intermediate Similarity	NPC83272
0.8366	Intermediate Similarity	NPC67197
0.8357	Intermediate Similarity	NPC88864
0.8357	Intermediate Similarity	NPC58685
0.8357	Intermediate Similarity	NPC70622
0.8357	Intermediate Similarity	NPC477407
0.8356	Intermediate Similarity	NPC469885
0.8356	Intermediate Similarity	NPC472006
0.8345	Intermediate Similarity	NPC53649
0.8345	Intermediate Similarity	NPC472604
0.8345	Intermediate Similarity	NPC187843
0.8345	Intermediate Similarity	NPC472605
0.8345	Intermediate Similarity	NPC31539
0.8345	Intermediate Similarity	NPC198305
0.8345	Intermediate Similarity	NPC158634
0.8345	Intermediate Similarity	NPC163169
0.8345	Intermediate Similarity	NPC123
0.8344	Intermediate Similarity	NPC477690
0.8344	Intermediate Similarity	NPC474533
0.8344	Intermediate Similarity	NPC180388
0.8344	Intermediate Similarity	NPC474534
0.8344	Intermediate Similarity	NPC115249
0.8333	Intermediate Similarity	NPC56204
0.8333	Intermediate Similarity	NPC282923
0.8333	Intermediate Similarity	NPC205766
0.8333	Intermediate Similarity	NPC31132
0.8322	Intermediate Similarity	NPC119542
0.8322	Intermediate Similarity	NPC301915
0.8322	Intermediate Similarity	NPC172329
0.8322	Intermediate Similarity	NPC474771
0.8322	Intermediate Similarity	NPC149372
0.8322	Intermediate Similarity	NPC261292
0.8322	Intermediate Similarity	NPC178467
0.8322	Intermediate Similarity	NPC2569
0.8322	Intermediate Similarity	NPC474849
0.8322	Intermediate Similarity	NPC65837
0.8322	Intermediate Similarity	NPC228012
0.8321	Intermediate Similarity	NPC51037
0.8311	Intermediate Similarity	NPC470570
0.8311	Intermediate Similarity	NPC120536
0.8311	Intermediate Similarity	NPC107625
0.8311	Intermediate Similarity	NPC472033
0.831	Intermediate Similarity	NPC283088
0.8309	Intermediate Similarity	NPC68756
0.8309	Intermediate Similarity	NPC152525
0.8299	Intermediate Similarity	NPC29932
0.8298	Intermediate Similarity	NPC115458
0.8298	Intermediate Similarity	NPC254603
0.8298	Intermediate Similarity	NPC193169
0.8298	Intermediate Similarity	NPC171968
0.8298	Intermediate Similarity	NPC472591
0.8296	Intermediate Similarity	NPC46634
0.8289	Intermediate Similarity	NPC137301

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 NPC306835 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	842
0.2-0.3	1534
0.3-0.4	2489
0.4-0.5	2172
0.5-0.6	1200
0.6-0.7	518
0.7-0.8	128
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8382	Intermediate Similarity	NPD1470	Approved
0.8267	Intermediate Similarity	NPD3226	Approved
0.8194	Intermediate Similarity	NPD2935	Discontinued
0.8182	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD2346	Discontinued
0.8088	Intermediate Similarity	NPD1201	Approved
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD2532	Approved
0.7852	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD3764	Approved
0.7823	Intermediate Similarity	NPD5408	Approved
0.7823	Intermediate Similarity	NPD5404	Approved
0.7823	Intermediate Similarity	NPD5405	Approved
0.7823	Intermediate Similarity	NPD5406	Approved
0.7821	Intermediate Similarity	NPD7819	Suspended
0.7778	Intermediate Similarity	NPD9493	Approved
0.7755	Intermediate Similarity	NPD2799	Discontinued
0.7755	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD8150	Discontinued
0.7708	Intermediate Similarity	NPD2313	Discontinued
0.7702	Intermediate Similarity	NPD6232	Discontinued
0.7669	Intermediate Similarity	NPD7473	Discontinued
0.7664	Intermediate Similarity	NPD9545	Approved
0.7661	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5402	Approved
0.7616	Intermediate Similarity	NPD3750	Approved
0.7586	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1551	Phase 2
0.756	Intermediate Similarity	NPD8313	Approved
0.756	Intermediate Similarity	NPD8312	Approved
0.755	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD8166	Discontinued
0.7484	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5844	Phase 1
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.7452	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2182	Approved
0.7432	Intermediate Similarity	NPD230	Phase 1
0.7432	Intermediate Similarity	NPD447	Suspended
0.7431	Intermediate Similarity	NPD2798	Approved
0.7423	Intermediate Similarity	NPD6959	Discontinued
0.7419	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4380	Phase 2
0.74	Intermediate Similarity	NPD1510	Phase 2
0.7394	Intermediate Similarity	NPD9717	Approved
0.7391	Intermediate Similarity	NPD7768	Phase 2
0.7383	Intermediate Similarity	NPD1607	Approved
0.7378	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD5711	Approved
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2801	Approved
0.7368	Intermediate Similarity	NPD1549	Phase 2
0.7365	Intermediate Similarity	NPD1240	Approved
0.7361	Intermediate Similarity	NPD1164	Approved
0.7361	Intermediate Similarity	NPD1203	Approved
0.7358	Intermediate Similarity	NPD7411	Suspended
0.7355	Intermediate Similarity	NPD7390	Discontinued
0.7347	Intermediate Similarity	NPD411	Approved
0.7333	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6832	Phase 2
0.7315	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD9266	Approved
0.7313	Intermediate Similarity	NPD74	Approved
0.7312	Intermediate Similarity	NPD1934	Approved
0.7305	Intermediate Similarity	NPD4626	Approved
0.7303	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2344	Approved
0.7297	Intermediate Similarity	NPD6663	Approved
0.7296	Intermediate Similarity	NPD6599	Discontinued
0.7285	Intermediate Similarity	NPD3748	Approved
0.7285	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7273	Intermediate Similarity	NPD6535	Approved
0.7261	Intermediate Similarity	NPD6273	Approved
0.726	Intermediate Similarity	NPD5736	Approved
0.7256	Intermediate Similarity	NPD5494	Approved
0.7254	Intermediate Similarity	NPD3496	Discontinued
0.7248	Intermediate Similarity	NPD943	Approved
0.7244	Intermediate Similarity	NPD6799	Approved
0.7239	Intermediate Similarity	NPD9263	Approved
0.7239	Intermediate Similarity	NPD3749	Approved
0.7239	Intermediate Similarity	NPD9267	Approved
0.7239	Intermediate Similarity	NPD9264	Approved
0.7238	Intermediate Similarity	NPD7435	Discontinued
0.7237	Intermediate Similarity	NPD2796	Approved
0.7235	Intermediate Similarity	NPD6559	Discontinued
0.7234	Intermediate Similarity	NPD5691	Approved
0.7226	Intermediate Similarity	NPD6190	Approved
0.7225	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6212	Phase 3
0.7216	Intermediate Similarity	NPD6213	Phase 3
0.7215	Intermediate Similarity	NPD5403	Approved
0.7208	Intermediate Similarity	NPD2800	Approved
0.7205	Intermediate Similarity	NPD6844	Discontinued
0.7205	Intermediate Similarity	NPD6801	Discontinued
0.7203	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2932	Approved
0.7178	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3882	Suspended
0.7172	Intermediate Similarity	NPD1283	Approved
0.7167	Intermediate Similarity	NPD6779	Approved
0.7167	Intermediate Similarity	NPD6777	Approved
0.7167	Intermediate Similarity	NPD6780	Approved
0.7167	Intermediate Similarity	NPD6782	Approved
0.7167	Intermediate Similarity	NPD6776	Approved
0.7167	Intermediate Similarity	NPD6778	Approved
0.7167	Intermediate Similarity	NPD6781	Approved
0.7162	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1608	Approved
0.7151	Intermediate Similarity	NPD7699	Phase 2
0.7151	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD164	Approved
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2979	Phase 3
0.7117	Intermediate Similarity	NPD3817	Phase 2
0.7115	Intermediate Similarity	NPD2309	Approved
0.7107	Intermediate Similarity	NPD920	Approved
0.7101	Intermediate Similarity	NPD7177	Discontinued
0.7101	Intermediate Similarity	NPD3818	Discontinued
0.7093	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5401	Approved
0.7089	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6002	Phase 3
0.7078	Intermediate Similarity	NPD6005	Phase 3
0.7078	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1471	Phase 3
0.7078	Intermediate Similarity	NPD6004	Phase 3
0.7076	Intermediate Similarity	NPD5953	Discontinued
0.7075	Intermediate Similarity	NPD1019	Discontinued
0.7067	Intermediate Similarity	NPD520	Approved
0.7063	Intermediate Similarity	NPD3019	Approved
0.7063	Intermediate Similarity	NPD1778	Approved
0.7059	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4308	Phase 3
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7049	Intermediate Similarity	NPD7698	Approved
0.7049	Intermediate Similarity	NPD7697	Approved
0.7049	Intermediate Similarity	NPD7696	Phase 3
0.7047	Intermediate Similarity	NPD7008	Discontinued
0.7025	Intermediate Similarity	NPD1511	Approved
0.702	Intermediate Similarity	NPD4060	Phase 1
0.7019	Intermediate Similarity	NPD7458	Discontinued
0.7011	Intermediate Similarity	NPD7870	Phase 2
0.7011	Intermediate Similarity	NPD7871	Phase 2
0.7011	Intermediate Similarity	NPD8319	Approved
0.7011	Intermediate Similarity	NPD8320	Phase 1
0.7007	Intermediate Similarity	NPD2797	Approved
0.7005	Intermediate Similarity	NPD7874	Approved
0.7005	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD9281	Approved
0.7	Intermediate Similarity	NPD3268	Approved
0.7	Intermediate Similarity	NPD5951	Approved
0.6995	Remote Similarity	NPD6823	Phase 2
0.6994	Remote Similarity	NPD37	Approved
0.6993	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6234	Discontinued
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6166	Phase 2
0.6982	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7635	Approved
0.6971	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4967	Phase 2
0.697	Remote Similarity	NPD4965	Approved
0.697	Remote Similarity	NPD4966	Approved
0.6968	Remote Similarity	NPD5762	Approved
0.6968	Remote Similarity	NPD5763	Approved
0.6966	Remote Similarity	NPD1281	Approved
0.6966	Remote Similarity	NPD1611	Approved
0.6962	Remote Similarity	NPD7236	Approved
0.6959	Remote Similarity	NPD7286	Phase 2
0.6948	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD17	Approved
0.694	Remote Similarity	NPD9261	Approved
0.6939	Remote Similarity	NPD6696	Suspended
0.6939	Remote Similarity	NPD1876	Approved
0.6937	Remote Similarity	NPD1512	Approved
0.6928	Remote Similarity	NPD6651	Approved
0.6919	Remote Similarity	NPD7074	Phase 3
0.6913	Remote Similarity	NPD2861	Phase 2

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