NPASS Compound

Structure

NPC107636 OpenBabel07101719402D 24 25 0 0 0 0 0 0 0 0999 V2000 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 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 -5.1962 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 -4.3301 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 -4.3301 3.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 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 -5.1962 -0.0000 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 -4.3301 4.5000 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 -6.0622 1.5000 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 -6.0622 0.5000 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 -5.1962 -1.0000 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 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 11 1 0 0 0 0 4 8 2 0 0 0 0 4 13 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 24 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.15
Volume:	544.202
LogP:	6.45
LogD:	2.689
LogS:	-4.882
# Rotatable Bonds:	5
TPSA:	195.98
# H-Bond Aceptor:	10
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.128
Synthetic Accessibility Score:	3.114
Fsp3:	0.133
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.369
MDCK Permeability:	5.986796622892143e-06
Pgp-inhibitor:	0.139
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.747
20% Bioavailability (F20%):	0.736
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	103.71978759765625%
Volume Distribution (VD):	0.057
Pgp-substrate:	1.0550603866577148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.757
CYP1A2-substrate:	0.39
CYP2C19-inhibitor:	0.133
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.576
CYP2C9-substrate:	0.185
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	10.228
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.028
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.521
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.933
Carcinogencity:	0.119
Eye Corrosion:	0.003
Eye Irritation:	0.967
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC107636

Natural Product ID:	NPC107636
*Common Name:**	Jaboticabin
IUPAC Name:	[3,5-dihydroxy-2-(2-methoxy-2-oxoethyl)phenyl] 3,4-dihydroxybenzoate
Synonyms:	jaboticabin
Standard InCHIKey:	LFLJQGHNYLKTBB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O8/c1-23-15(21)7-10-12(19)5-9(17)6-14(10)24-16(22)8-2-3-11(18)13(20)4-8/h2-6,17-20H,7H2,1H3
SMILES:	COC(=O)Cc1c(cc(cc1O)O)OC(=O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495849
PubChem CID:	16083179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO32785	myrciaria cauliflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933884]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	65000.0	nM	PMID[488986]
NPT35	Others	n.a.		IC50	=	51400.0	nM	PMID[488986]
NPT2	Others	Unspecified		Inhibition	=	81.3	%	PMID[488986]
NPT2	Others	Unspecified		Activity	=	47.3	%	PMID[488986]

☑ 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 NPC107636 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	362
0.1-0.2	1665
0.2-0.3	4597
0.3-0.4	10114
0.4-0.5	7494
0.5-0.6	3374
0.6-0.7	5065
0.7-0.8	6553
0.8-0.85	2718
0.85-0.9	693
0.9-0.95	60
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC262282
0.9388	High Similarity	NPC75695
0.9371	High Similarity	NPC134975
0.9267	High Similarity	NPC318432
0.9267	High Similarity	NPC54928
0.9252	High Similarity	NPC473091
0.9211	High Similarity	NPC53889
0.9211	High Similarity	NPC24164
0.9205	High Similarity	NPC114179
0.9205	High Similarity	NPC68324
0.9205	High Similarity	NPC156818
0.9205	High Similarity	NPC38779
0.9205	High Similarity	NPC289322
0.9205	High Similarity	NPC160512
0.9195	High Similarity	NPC289968
0.9167	High Similarity	NPC312256
0.9161	High Similarity	NPC326065
0.9145	High Similarity	NPC267627
0.9145	High Similarity	NPC87317
0.9145	High Similarity	NPC40702
0.9145	High Similarity	NPC37502
0.9139	High Similarity	NPC300845
0.9139	High Similarity	NPC291948
0.9139	High Similarity	NPC88803
0.9139	High Similarity	NPC104983
0.9139	High Similarity	NPC250436
0.9116	High Similarity	NPC108406
0.9116	High Similarity	NPC472969
0.9116	High Similarity	NPC139839
0.911	High Similarity	NPC287275
0.9097	High Similarity	NPC142614
0.9097	High Similarity	NPC110419
0.9079	High Similarity	NPC247713
0.9067	High Similarity	NPC60972
0.9067	High Similarity	NPC39732
0.906	High Similarity	NPC184136
0.9048	High Similarity	NPC165389
0.9041	High Similarity	NPC105213
0.9041	High Similarity	NPC207732
0.9034	High Similarity	NPC284556
0.9034	High Similarity	NPC301178
0.9021	High Similarity	NPC207516
0.9007	High Similarity	NPC475895
0.9	High Similarity	NPC260895
0.9	High Similarity	NPC31363
0.8993	High Similarity	NPC52005
0.8993	High Similarity	NPC87125
0.8993	High Similarity	NPC137062
0.8993	High Similarity	NPC270465
0.8993	High Similarity	NPC287101
0.8993	High Similarity	NPC223579
0.8993	High Similarity	NPC183950
0.8986	High Similarity	NPC95864
0.898	High Similarity	NPC70136
0.8973	High Similarity	NPC287722
0.8973	High Similarity	NPC471417
0.8968	High Similarity	NPC471745
0.8968	High Similarity	NPC476371
0.8968	High Similarity	NPC476372
0.8961	High Similarity	NPC130955
0.8961	High Similarity	NPC239966
0.8961	High Similarity	NPC200594
0.8961	High Similarity	NPC471744
0.8961	High Similarity	NPC203020
0.8951	High Similarity	NPC25305
0.8951	High Similarity	NPC112068
0.8951	High Similarity	NPC125417
0.8951	High Similarity	NPC110899
0.8951	High Similarity	NPC95679
0.8947	High Similarity	NPC146165
0.8947	High Similarity	NPC4455
0.8947	High Similarity	NPC20830
0.8947	High Similarity	NPC2476
0.8947	High Similarity	NPC138360
0.8947	High Similarity	NPC280339
0.8947	High Similarity	NPC50715
0.8947	High Similarity	NPC128863
0.8947	High Similarity	NPC183597
0.8947	High Similarity	NPC214138
0.8947	High Similarity	NPC256612
0.8947	High Similarity	NPC163780
0.8947	High Similarity	NPC196439
0.8947	High Similarity	NPC201136
0.8947	High Similarity	NPC208197
0.8947	High Similarity	NPC2928
0.8947	High Similarity	NPC227325
0.8947	High Similarity	NPC167815
0.8947	High Similarity	NPC92659
0.894	High Similarity	NPC162313
0.894	High Similarity	NPC239128
0.894	High Similarity	NPC25270
0.894	High Similarity	NPC57030
0.894	High Similarity	NPC120163
0.894	High Similarity	NPC187498
0.894	High Similarity	NPC198826
0.894	High Similarity	NPC257648
0.894	High Similarity	NPC83508
0.894	High Similarity	NPC199773
0.894	High Similarity	NPC142540
0.894	High Similarity	NPC100887
0.894	High Similarity	NPC222830
0.894	High Similarity	NPC55205
0.894	High Similarity	NPC275836
0.894	High Similarity	NPC293183
0.894	High Similarity	NPC188203
0.894	High Similarity	NPC71334
0.894	High Similarity	NPC301323
0.894	High Similarity	NPC212678
0.894	High Similarity	NPC477231
0.894	High Similarity	NPC275722
0.894	High Similarity	NPC474656
0.894	High Similarity	NPC256283
0.894	High Similarity	NPC131624
0.894	High Similarity	NPC156222
0.894	High Similarity	NPC241498
0.8933	High Similarity	NPC188871
0.8933	High Similarity	NPC62042
0.8933	High Similarity	NPC286342
0.8933	High Similarity	NPC149127
0.8933	High Similarity	NPC29231
0.8926	High Similarity	NPC119059
0.8926	High Similarity	NPC98809
0.8926	High Similarity	NPC120464
0.8926	High Similarity	NPC476394
0.8926	High Similarity	NPC118726
0.8926	High Similarity	NPC12367
0.8924	High Similarity	NPC280493
0.8912	High Similarity	NPC142165
0.8912	High Similarity	NPC279121
0.8903	High Similarity	NPC112418
0.8896	High Similarity	NPC238381
0.8896	High Similarity	NPC83763
0.8896	High Similarity	NPC289811
0.8896	High Similarity	NPC160780
0.8896	High Similarity	NPC168616
0.8889	High Similarity	NPC247017
0.8889	High Similarity	NPC98661
0.8889	High Similarity	NPC472916
0.8889	High Similarity	NPC265511
0.8882	High Similarity	NPC255350
0.8882	High Similarity	NPC22519
0.8882	High Similarity	NPC69394
0.8882	High Similarity	NPC183878
0.8882	High Similarity	NPC145379
0.8882	High Similarity	NPC274327
0.8882	High Similarity	NPC231018
0.8882	High Similarity	NPC167091
0.8882	High Similarity	NPC88645
0.8882	High Similarity	NPC178134
0.8882	High Similarity	NPC250822
0.8882	High Similarity	NPC276409
0.8882	High Similarity	NPC206238
0.8882	High Similarity	NPC47781
0.8882	High Similarity	NPC271779
0.8882	High Similarity	NPC75279
0.8882	High Similarity	NPC176775
0.8882	High Similarity	NPC160951
0.8882	High Similarity	NPC292214
0.8881	High Similarity	NPC223616
0.8881	High Similarity	NPC156892
0.8874	High Similarity	NPC54394
0.8874	High Similarity	NPC28274
0.8874	High Similarity	NPC50403
0.8874	High Similarity	NPC200740
0.8874	High Similarity	NPC133953
0.8874	High Similarity	NPC125062
0.8874	High Similarity	NPC252933
0.8867	High Similarity	NPC92722
0.8867	High Similarity	NPC48479
0.8867	High Similarity	NPC105512
0.8867	High Similarity	NPC102003
0.8867	High Similarity	NPC177298
0.8867	High Similarity	NPC183959
0.8867	High Similarity	NPC1612
0.8861	High Similarity	NPC473818
0.8861	High Similarity	NPC116745
0.8859	High Similarity	NPC74881
0.8859	High Similarity	NPC12200
0.8859	High Similarity	NPC130230
0.8859	High Similarity	NPC239312
0.8859	High Similarity	NPC51443
0.8859	High Similarity	NPC168803
0.8859	High Similarity	NPC275772
0.8854	High Similarity	NPC88243
0.8851	High Similarity	NPC131766
0.8851	High Similarity	NPC157133
0.8844	High Similarity	NPC473090
0.8844	High Similarity	NPC254659
0.8844	High Similarity	NPC175013
0.8839	High Similarity	NPC24627
0.8839	High Similarity	NPC155101
0.8839	High Similarity	NPC476373
0.8839	High Similarity	NPC292415
0.8831	High Similarity	NPC163524
0.8831	High Similarity	NPC210084
0.8831	High Similarity	NPC99597
0.8831	High Similarity	NPC176665
0.8831	High Similarity	NPC189179
0.8831	High Similarity	NPC472860
0.8831	High Similarity	NPC305663

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 NPC107636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	951
0.2-0.3	1818
0.3-0.4	2578
0.4-0.5	1736
0.5-0.6	1076
0.6-0.7	471
0.7-0.8	150
0.8-0.85	37
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9139	High Similarity	NPD4868	Clinical (unspecified phase)
0.8912	High Similarity	NPD1511	Approved
0.8882	High Similarity	NPD2801	Approved
0.8882	High Similarity	NPD1465	Phase 2
0.8816	High Similarity	NPD1934	Approved
0.8803	High Similarity	NPD230	Phase 1
0.8792	High Similarity	NPD1512	Approved
0.8766	High Similarity	NPD3882	Suspended
0.8758	High Similarity	NPD2393	Clinical (unspecified phase)
0.8701	High Similarity	NPD3817	Phase 2
0.8509	High Similarity	NPD3818	Discontinued
0.8466	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD6799	Approved
0.8385	Intermediate Similarity	NPD6166	Phase 2
0.8385	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6232	Discontinued
0.8364	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7075	Discontinued
0.8344	Intermediate Similarity	NPD7054	Approved
0.8344	Intermediate Similarity	NPD5844	Phase 1
0.8333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3750	Approved
0.8322	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7472	Approved
0.8293	Intermediate Similarity	NPD7074	Phase 3
0.8288	Intermediate Similarity	NPD447	Suspended
0.828	Intermediate Similarity	NPD7819	Suspended
0.8242	Intermediate Similarity	NPD6797	Phase 2
0.8235	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7473	Discontinued
0.8219	Intermediate Similarity	NPD943	Approved
0.8219	Intermediate Similarity	NPD1240	Approved
0.82	Intermediate Similarity	NPD1549	Phase 2
0.8193	Intermediate Similarity	NPD7251	Discontinued
0.8188	Intermediate Similarity	NPD1551	Phase 2
0.8165	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD9269	Phase 2
0.8153	Intermediate Similarity	NPD7411	Suspended
0.8133	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1510	Phase 2
0.8113	Intermediate Similarity	NPD5402	Approved
0.8108	Intermediate Similarity	NPD1607	Approved
0.8101	Intermediate Similarity	NPD6801	Discontinued
0.8092	Intermediate Similarity	NPD4628	Phase 3
0.8089	Intermediate Similarity	NPD4380	Phase 2
0.8089	Intermediate Similarity	NPD6599	Discontinued
0.8069	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD2935	Discontinued
0.8039	Intermediate Similarity	NPD6190	Approved
0.8036	Intermediate Similarity	NPD7808	Phase 3
0.8026	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3748	Approved
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1203	Approved
0.7973	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1613	Approved
0.7963	Intermediate Similarity	NPD919	Approved
0.7962	Intermediate Similarity	NPD1653	Approved
0.7958	Intermediate Similarity	NPD422	Phase 1
0.7947	Intermediate Similarity	NPD2796	Approved
0.7914	Intermediate Similarity	NPD5494	Approved
0.7911	Intermediate Similarity	NPD3226	Approved
0.7898	Intermediate Similarity	NPD5403	Approved
0.7898	Intermediate Similarity	NPD920	Approved
0.7885	Intermediate Similarity	NPD5401	Approved
0.7885	Intermediate Similarity	NPD2532	Approved
0.7885	Intermediate Similarity	NPD2534	Approved
0.7885	Intermediate Similarity	NPD2533	Approved
0.7877	Intermediate Similarity	NPD9494	Approved
0.7872	Intermediate Similarity	NPD9268	Approved
0.7866	Intermediate Similarity	NPD7199	Phase 2
0.7857	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6234	Discontinued
0.784	Intermediate Similarity	NPD7768	Phase 2
0.7831	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6832	Phase 2
0.7821	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1243	Approved
0.7778	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9717	Approved
0.7778	Intermediate Similarity	NPD1608	Approved
0.7771	Intermediate Similarity	NPD3926	Phase 2
0.7771	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3027	Phase 3
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7763	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD4308	Phase 3
0.7742	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5953	Discontinued
0.7692	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1933	Approved
0.7677	Intermediate Similarity	NPD2800	Approved
0.7676	Intermediate Similarity	NPD9545	Approved
0.7671	Intermediate Similarity	NPD3225	Approved
0.7665	Intermediate Similarity	NPD5242	Approved
0.7661	Intermediate Similarity	NPD7685	Pre-registration
0.7654	Intermediate Similarity	NPD37	Approved
0.7651	Intermediate Similarity	NPD6959	Discontinued
0.7651	Intermediate Similarity	NPD1247	Approved
0.7647	Intermediate Similarity	NPD2799	Discontinued
0.7643	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4965	Approved
0.7622	Intermediate Similarity	NPD4967	Phase 2
0.7622	Intermediate Similarity	NPD4966	Approved
0.7619	Intermediate Similarity	NPD2797	Approved
0.7603	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD411	Approved
0.76	Intermediate Similarity	NPD2313	Discontinued
0.76	Intermediate Similarity	NPD3268	Approved
0.7593	Intermediate Similarity	NPD6386	Approved
0.7593	Intermediate Similarity	NPD6385	Approved
0.7588	Intermediate Similarity	NPD7286	Phase 2
0.7586	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD17	Approved
0.7561	Intermediate Similarity	NPD5353	Approved
0.7557	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2346	Discontinued
0.7548	Intermediate Similarity	NPD2344	Approved
0.7529	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD4307	Phase 2
0.7484	Intermediate Similarity	NPD6099	Approved
0.7484	Intermediate Similarity	NPD6100	Approved
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD3764	Approved
0.7455	Intermediate Similarity	NPD4288	Approved
0.7438	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7266	Discontinued
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7415	Intermediate Similarity	NPD1481	Phase 2
0.7396	Intermediate Similarity	NPD7229	Phase 3
0.7383	Intermediate Similarity	NPD3267	Approved
0.7383	Intermediate Similarity	NPD3266	Approved
0.7378	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6798	Discontinued
0.7365	Intermediate Similarity	NPD6971	Discontinued
0.7358	Intermediate Similarity	NPD2354	Approved
0.7358	Intermediate Similarity	NPD2309	Approved
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7347	Intermediate Similarity	NPD1535	Discovery
0.7347	Intermediate Similarity	NPD1610	Phase 2
0.7342	Intermediate Similarity	NPD1652	Phase 2
0.7338	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD1019	Discontinued
0.7325	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6233	Phase 2
0.7308	Intermediate Similarity	NPD7033	Discontinued
0.7308	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5710	Approved
0.7294	Intermediate Similarity	NPD5711	Approved
0.7292	Intermediate Similarity	NPD9493	Approved
0.729	Intermediate Similarity	NPD6651	Approved
0.7285	Intermediate Similarity	NPD3018	Phase 2
0.7284	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7267	Intermediate Similarity	NPD4357	Discontinued
0.7257	Intermediate Similarity	NPD7039	Approved
0.7257	Intermediate Similarity	NPD7038	Approved
0.7256	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3455	Phase 2
0.7255	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8434	Phase 2
0.7237	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8127	Discontinued
0.7226	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5124	Phase 1
0.7211	Intermediate Similarity	NPD1778	Approved
0.7193	Intermediate Similarity	NPD3787	Discontinued
0.7192	Intermediate Similarity	NPD1894	Discontinued
0.7189	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6273	Approved
0.7175	Intermediate Similarity	NPD8313	Approved
0.7175	Intermediate Similarity	NPD8312	Approved
0.7162	Intermediate Similarity	NPD3496	Discontinued
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7133	Intermediate Similarity	NPD2982	Phase 2
0.7133	Intermediate Similarity	NPD2983	Phase 2
0.7123	Intermediate Similarity	NPD5536	Phase 2
0.712	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7549	Discontinued
0.7107	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2353	Approved
0.7099	Intermediate Similarity	NPD7440	Discontinued
0.7097	Intermediate Similarity	NPD4062	Phase 3
0.7086	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD1241	Discontinued
0.7083	Intermediate Similarity	NPD8455	Phase 2
0.7081	Intermediate Similarity	NPD7003	Approved
0.7081	Intermediate Similarity	NPD8166	Discontinued
0.7081	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4110	Phase 3

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