NPASS Compound

Structure

NPC301949 OpenBabel07101718312D 25 29 0 0 0 0 0 0 0 0999 V2000 3.1631 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -2.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1631 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 -0.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 -1.2313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8084 2.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 1.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 0.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 1.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8084 -0.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8084 0.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4065 0.7687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 2.2687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 -1.2313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 1.2029 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 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 11 1 0 0 0 0 4 11 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 22 2 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.08
Volume:	331.917
LogP:	3.702
LogD:	2.945
LogS:	-4.317
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	3.376
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.909
MDCK Permeability:	1.9939732737839222e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.106

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	97.93753814697266%
Volume Distribution (VD):	0.586
Pgp-substrate:	1.194244146347046%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.2
CYP2C19-inhibitor:	0.901
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.884
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.832
CYP2D6-substrate:	0.405
CYP3A4-inhibitor:	0.715
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	6.956
Half-life (T1/2):	0.777

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.942
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.908
Carcinogencity:	0.943
Eye Corrosion:	0.003
Eye Irritation:	0.893
Respiratory Toxicity:	0.841

Download Data

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

Natural Product: NPC301949

Natural Product ID:	NPC301949
*Common Name:**	Palmarumycin Cp17
IUPAC Name:	n.a.
Synonyms:	Palmarumycin CP17
Standard InCHIKey:	CDNGGUFYOISKCW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H14O5/c21-12-7-8-14(23)19-18(12)13(22)9-10-20(19)24-15-5-1-3-11-4-2-6-16(25-20)17(11)15/h1-8,21,23H,9-10H2
SMILES:	Oc1ccc(c2c1C1(CCC2=O)Oc2cccc3c2c(O1)ccc3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457641
PubChem CID:	25147577
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO32660	edenia sp.	Species	Pleosporaceae	Eukaryota	n.a.	Panamanian	n.a.	PMID[19007286]
NPO33512	berkleasmium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[25237727]

☑ 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	12
MIC	6
Others	1

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	3
Organism	10
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	174000.0	nM	PMID[559749]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[559750]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[559750]
NPT4651	Cell Line	Ramos	Homo sapiens	IC50	=	33100.0	nM	PMID[559751]
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	>	100000.0	nM	PMID[559751]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	1340.0	nM	PMID[559749]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	10000.0	nM	PMID[559749]
NPT27	Others	Unspecified		Ratio IC50	=	130.0	n.a.	PMID[559749]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10000.0	nM	PMID[559749]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[559750]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[559750]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[559750]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[559750]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[559750]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[559750]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[559750]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[559750]

☑ 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 NPC301949 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	414
0.1-0.2	1847
0.2-0.3	4704
0.3-0.4	12392
0.4-0.5	5444
0.5-0.6	4557
0.6-0.7	6582
0.7-0.8	6507
0.8-0.85	225
0.85-0.9	19
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC306816
0.9645	High Similarity	NPC47152
0.9507	High Similarity	NPC473951
0.9195	High Similarity	NPC57141
0.9145	High Similarity	NPC73148
0.8896	High Similarity	NPC472157
0.8844	High Similarity	NPC97662
0.8767	High Similarity	NPC197461
0.8767	High Similarity	NPC133585
0.8759	High Similarity	NPC473499
0.8652	High Similarity	NPC141549
0.8582	High Similarity	NPC278787
0.8582	High Similarity	NPC7569
0.8581	High Similarity	NPC257404
0.8562	High Similarity	NPC18457
0.8533	High Similarity	NPC211565
0.8526	High Similarity	NPC183402
0.8509	High Similarity	NPC472160
0.8491	Intermediate Similarity	NPC11608
0.8491	Intermediate Similarity	NPC297404
0.8447	Intermediate Similarity	NPC137460
0.8446	Intermediate Similarity	NPC145673
0.8442	Intermediate Similarity	NPC281272
0.8431	Intermediate Similarity	NPC227122
0.8411	Intermediate Similarity	NPC60389
0.8411	Intermediate Similarity	NPC11800
0.8411	Intermediate Similarity	NPC206579
0.8408	Intermediate Similarity	NPC193749
0.8405	Intermediate Similarity	NPC85368
0.8403	Intermediate Similarity	NPC138940
0.8387	Intermediate Similarity	NPC95842
0.8387	Intermediate Similarity	NPC280530
0.8387	Intermediate Similarity	NPC178964
0.8385	Intermediate Similarity	NPC103633
0.8354	Intermediate Similarity	NPC184326
0.8354	Intermediate Similarity	NPC472158
0.8354	Intermediate Similarity	NPC292863
0.8344	Intermediate Similarity	NPC177742
0.8333	Intermediate Similarity	NPC254351
0.8333	Intermediate Similarity	NPC159855
0.8333	Intermediate Similarity	NPC55662
0.8333	Intermediate Similarity	NPC166054
0.8333	Intermediate Similarity	NPC169479
0.8323	Intermediate Similarity	NPC474843
0.8303	Intermediate Similarity	NPC102053
0.8302	Intermediate Similarity	NPC137232
0.8302	Intermediate Similarity	NPC18380
0.8301	Intermediate Similarity	NPC106328
0.8301	Intermediate Similarity	NPC35150
0.8291	Intermediate Similarity	NPC195167
0.8282	Intermediate Similarity	NPC472159
0.828	Intermediate Similarity	NPC469507
0.8269	Intermediate Similarity	NPC92153
0.8269	Intermediate Similarity	NPC279281
0.8269	Intermediate Similarity	NPC230439
0.8269	Intermediate Similarity	NPC299761
0.8269	Intermediate Similarity	NPC135522
0.8267	Intermediate Similarity	NPC69755
0.8258	Intermediate Similarity	NPC39819
0.8247	Intermediate Similarity	NPC70764
0.8235	Intermediate Similarity	NPC71055
0.8228	Intermediate Similarity	NPC67197
0.8212	Intermediate Similarity	NPC310340
0.821	Intermediate Similarity	NPC272560
0.821	Intermediate Similarity	NPC30027
0.8204	Intermediate Similarity	NPC299149
0.8204	Intermediate Similarity	NPC114257
0.8204	Intermediate Similarity	NPC277710
0.8204	Intermediate Similarity	NPC58538
0.8204	Intermediate Similarity	NPC153578
0.82	Intermediate Similarity	NPC275734
0.82	Intermediate Similarity	NPC124365
0.8199	Intermediate Similarity	NPC290160
0.8194	Intermediate Similarity	NPC325983
0.8194	Intermediate Similarity	NPC295036
0.8194	Intermediate Similarity	NPC470107
0.8194	Intermediate Similarity	NPC120105
0.8194	Intermediate Similarity	NPC101957
0.8182	Intermediate Similarity	NPC186397
0.8182	Intermediate Similarity	NPC59491
0.8182	Intermediate Similarity	NPC24748
0.8182	Intermediate Similarity	NPC203751
0.8182	Intermediate Similarity	NPC37135
0.8182	Intermediate Similarity	NPC5537
0.8176	Intermediate Similarity	NPC55443
0.8176	Intermediate Similarity	NPC474290
0.8176	Intermediate Similarity	NPC18699
0.8176	Intermediate Similarity	NPC177650
0.8176	Intermediate Similarity	NPC186113
0.817	Intermediate Similarity	NPC300540
0.8165	Intermediate Similarity	NPC137100
0.8156	Intermediate Similarity	NPC193805
0.8153	Intermediate Similarity	NPC89474
0.8153	Intermediate Similarity	NPC477691
0.8153	Intermediate Similarity	NPC185103
0.8148	Intermediate Similarity	NPC259757
0.8141	Intermediate Similarity	NPC138299
0.8141	Intermediate Similarity	NPC222713
0.8141	Intermediate Similarity	NPC115324
0.8141	Intermediate Similarity	NPC111112
0.8141	Intermediate Similarity	NPC23668
0.8141	Intermediate Similarity	NPC202157
0.8141	Intermediate Similarity	NPC67322
0.8141	Intermediate Similarity	NPC193976
0.8138	Intermediate Similarity	NPC137264
0.8137	Intermediate Similarity	NPC278329
0.8137	Intermediate Similarity	NPC61594
0.8137	Intermediate Similarity	NPC212099
0.8137	Intermediate Similarity	NPC216752
0.8137	Intermediate Similarity	NPC146837
0.8137	Intermediate Similarity	NPC101116
0.8137	Intermediate Similarity	NPC56735
0.8129	Intermediate Similarity	NPC223988
0.8129	Intermediate Similarity	NPC266499
0.8125	Intermediate Similarity	NPC186325
0.8125	Intermediate Similarity	NPC139036
0.8125	Intermediate Similarity	NPC312993
0.8121	Intermediate Similarity	NPC472151
0.8117	Intermediate Similarity	NPC12305
0.8117	Intermediate Similarity	NPC46941
0.8113	Intermediate Similarity	NPC477833
0.8113	Intermediate Similarity	NPC185526
0.8112	Intermediate Similarity	NPC298884
0.811	Intermediate Similarity	NPC246274
0.811	Intermediate Similarity	NPC222455
0.8107	Intermediate Similarity	NPC476203
0.8105	Intermediate Similarity	NPC32470
0.8105	Intermediate Similarity	NPC131766
0.8101	Intermediate Similarity	NPC258474
0.8101	Intermediate Similarity	NPC66441
0.8101	Intermediate Similarity	NPC3898
0.8101	Intermediate Similarity	NPC182555
0.8101	Intermediate Similarity	NPC134171
0.8101	Intermediate Similarity	NPC99199
0.8101	Intermediate Similarity	NPC300668
0.8101	Intermediate Similarity	NPC201227
0.8089	Intermediate Similarity	NPC142308
0.8089	Intermediate Similarity	NPC473967
0.8089	Intermediate Similarity	NPC477690
0.8089	Intermediate Similarity	NPC207624
0.8086	Intermediate Similarity	NPC147596
0.8086	Intermediate Similarity	NPC127415
0.8084	Intermediate Similarity	NPC101991
0.8084	Intermediate Similarity	NPC289876
0.8082	Intermediate Similarity	NPC118253
0.8079	Intermediate Similarity	NPC149780
0.8077	Intermediate Similarity	NPC471984
0.8077	Intermediate Similarity	NPC93619
0.8075	Intermediate Similarity	NPC273467
0.8075	Intermediate Similarity	NPC189552
0.8075	Intermediate Similarity	NPC132737
0.8075	Intermediate Similarity	NPC34089
0.8075	Intermediate Similarity	NPC196179
0.8075	Intermediate Similarity	NPC472261
0.8069	Intermediate Similarity	NPC39753
0.8069	Intermediate Similarity	NPC115998
0.8065	Intermediate Similarity	NPC276930
0.8063	Intermediate Similarity	NPC190487
0.8063	Intermediate Similarity	NPC154304
0.8063	Intermediate Similarity	NPC472156
0.8059	Intermediate Similarity	NPC224557
0.8059	Intermediate Similarity	NPC292706
0.8059	Intermediate Similarity	NPC231254
0.8054	Intermediate Similarity	NPC477534
0.8052	Intermediate Similarity	NPC308799
0.8052	Intermediate Similarity	NPC267509
0.805	Intermediate Similarity	NPC198489
0.805	Intermediate Similarity	NPC61112
0.805	Intermediate Similarity	NPC309648
0.805	Intermediate Similarity	NPC13879
0.805	Intermediate Similarity	NPC142339
0.805	Intermediate Similarity	NPC274730
0.805	Intermediate Similarity	NPC32867
0.805	Intermediate Similarity	NPC69531
0.8041	Intermediate Similarity	NPC281513
0.8041	Intermediate Similarity	NPC22222
0.8039	Intermediate Similarity	NPC113770
0.8038	Intermediate Similarity	NPC260604
0.8038	Intermediate Similarity	NPC303485
0.8038	Intermediate Similarity	NPC290830
0.8038	Intermediate Similarity	NPC235333
0.8038	Intermediate Similarity	NPC72425
0.8038	Intermediate Similarity	NPC71061
0.8038	Intermediate Similarity	NPC194593
0.8038	Intermediate Similarity	NPC299435
0.8038	Intermediate Similarity	NPC329844
0.8037	Intermediate Similarity	NPC280923
0.8037	Intermediate Similarity	NPC178281
0.8037	Intermediate Similarity	NPC474591
0.8027	Intermediate Similarity	NPC128216
0.8027	Intermediate Similarity	NPC477536
0.8026	Intermediate Similarity	NPC105648
0.8026	Intermediate Similarity	NPC329493
0.8025	Intermediate Similarity	NPC106372
0.8025	Intermediate Similarity	NPC477239
0.8025	Intermediate Similarity	NPC473961
0.8025	Intermediate Similarity	NPC3448
0.8025	Intermediate Similarity	NPC469575
0.8025	Intermediate Similarity	NPC15374
0.8025	Intermediate Similarity	NPC58668

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 NPC301949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	993
0.2-0.3	1536
0.3-0.4	2732
0.4-0.5	1852
0.5-0.6	1143
0.6-0.7	365
0.7-0.8	137
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8243	Intermediate Similarity	NPD2346	Discontinued
0.8113	Intermediate Similarity	NPD3749	Approved
0.8075	Intermediate Similarity	NPD6959	Discontinued
0.7976	Intermediate Similarity	NPD8313	Approved
0.7976	Intermediate Similarity	NPD8312	Approved
0.7972	Intermediate Similarity	NPD1203	Approved
0.7961	Intermediate Similarity	NPD3750	Approved
0.7945	Intermediate Similarity	NPD2313	Discontinued
0.7939	Intermediate Similarity	NPD3751	Discontinued
0.7933	Intermediate Similarity	NPD2935	Discontinued
0.7914	Intermediate Similarity	NPD3787	Discontinued
0.7898	Intermediate Similarity	NPD3226	Approved
0.7898	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2801	Approved
0.7806	Intermediate Similarity	NPD1511	Approved
0.7793	Intermediate Similarity	NPD2798	Approved
0.7778	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5402	Approved
0.7763	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2344	Approved
0.7763	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7768	Phase 2
0.7712	Intermediate Similarity	NPD1549	Phase 2
0.7711	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1512	Approved
0.7706	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7819	Suspended
0.7679	Intermediate Similarity	NPD7054	Approved
0.7667	Intermediate Similarity	NPD1933	Approved
0.7667	Intermediate Similarity	NPD447	Suspended
0.7657	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1934	Approved
0.7639	Intermediate Similarity	NPD9717	Approved
0.7633	Intermediate Similarity	NPD7074	Phase 3
0.7633	Intermediate Similarity	NPD7472	Approved
0.7632	Intermediate Similarity	NPD3748	Approved
0.7632	Intermediate Similarity	NPD2799	Discontinued
0.7613	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6166	Phase 2
0.7603	Intermediate Similarity	NPD1470	Approved
0.7597	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6232	Discontinued
0.7588	Intermediate Similarity	NPD6797	Phase 2
0.7582	Intermediate Similarity	NPD1551	Phase 2
0.7582	Intermediate Similarity	NPD5404	Approved
0.7582	Intermediate Similarity	NPD5405	Approved
0.7582	Intermediate Similarity	NPD5406	Approved
0.7582	Intermediate Similarity	NPD5408	Approved
0.758	Intermediate Similarity	NPD7390	Discontinued
0.7578	Intermediate Similarity	NPD7411	Suspended
0.7574	Intermediate Similarity	NPD5844	Phase 1
0.7569	Intermediate Similarity	NPD1201	Approved
0.7569	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2309	Approved
0.756	Intermediate Similarity	NPD7473	Discontinued
0.755	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7251	Discontinued
0.7544	Intermediate Similarity	NPD6559	Discontinued
0.7531	Intermediate Similarity	NPD6844	Discontinued
0.7516	Intermediate Similarity	NPD1510	Phase 2
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7483	Intermediate Similarity	NPD2797	Approved
0.7471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD411	Approved
0.7467	Intermediate Similarity	NPD3268	Approved
0.745	Intermediate Similarity	NPD6832	Phase 2
0.7421	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4380	Phase 2
0.7403	Intermediate Similarity	NPD4308	Phase 3
0.7394	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1240	Approved
0.7365	Intermediate Similarity	NPD5494	Approved
0.7363	Intermediate Similarity	NPD6777	Approved
0.7363	Intermediate Similarity	NPD6780	Approved
0.7363	Intermediate Similarity	NPD6776	Approved
0.7363	Intermediate Similarity	NPD6778	Approved
0.7363	Intermediate Similarity	NPD6781	Approved
0.7363	Intermediate Similarity	NPD6782	Approved
0.7363	Intermediate Similarity	NPD6779	Approved
0.7351	Intermediate Similarity	NPD3764	Approved
0.7329	Intermediate Similarity	NPD5403	Approved
0.7312	Intermediate Similarity	NPD5401	Approved
0.7308	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7871	Phase 2
0.7297	Intermediate Similarity	NPD3225	Approved
0.7297	Intermediate Similarity	NPD7870	Phase 2
0.729	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3882	Suspended
0.7283	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6823	Phase 2
0.7279	Intermediate Similarity	NPD1481	Phase 2
0.7273	Intermediate Similarity	NPD1607	Approved
0.7273	Intermediate Similarity	NPD8455	Phase 2
0.7249	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7783	Phase 2
0.7248	Intermediate Similarity	NPD3267	Approved
0.7248	Intermediate Similarity	NPD3266	Approved
0.7246	Intermediate Similarity	NPD7075	Discontinued
0.7244	Intermediate Similarity	NPD2796	Approved
0.7244	Intermediate Similarity	NPD6099	Approved
0.7244	Intermediate Similarity	NPD6100	Approved
0.7243	Intermediate Similarity	NPD7698	Approved
0.7243	Intermediate Similarity	NPD7696	Phase 3
0.7243	Intermediate Similarity	NPD7435	Discontinued
0.7243	Intermediate Similarity	NPD7697	Approved
0.7239	Intermediate Similarity	NPD7458	Discontinued
0.7229	Intermediate Similarity	NPD3817	Phase 2
0.7215	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2800	Approved
0.7211	Intermediate Similarity	NPD1535	Discovery
0.7205	Intermediate Similarity	NPD2532	Approved
0.7205	Intermediate Similarity	NPD2533	Approved
0.7205	Intermediate Similarity	NPD2534	Approved
0.7171	Intermediate Similarity	NPD4625	Phase 3
0.717	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6273	Approved
0.7153	Intermediate Similarity	NPD9493	Approved
0.7151	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD6799	Approved
0.7127	Intermediate Similarity	NPD6212	Phase 3
0.7127	Intermediate Similarity	NPD6213	Phase 3
0.7127	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4908	Phase 1
0.7095	Intermediate Similarity	NPD1611	Approved
0.709	Intermediate Similarity	NPD7701	Phase 2
0.7089	Intermediate Similarity	NPD1471	Phase 3
0.7088	Intermediate Similarity	NPD6535	Approved
0.7088	Intermediate Similarity	NPD6534	Approved
0.7086	Intermediate Similarity	NPD1019	Discontinued
0.7083	Intermediate Similarity	NPD6671	Approved
0.7078	Intermediate Similarity	NPD6233	Phase 2
0.7053	Intermediate Similarity	NPD8151	Discontinued
0.7047	Intermediate Similarity	NPD1608	Approved
0.7032	Intermediate Similarity	NPD943	Approved
0.7027	Intermediate Similarity	NPD3496	Discontinued
0.7024	Intermediate Similarity	NPD4288	Approved
0.7024	Intermediate Similarity	NPD2296	Approved
0.702	Intermediate Similarity	NPD1164	Approved
0.7016	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7874	Approved
0.7013	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7177	Discontinued
0.6994	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6599	Discontinued
0.6979	Remote Similarity	NPD7801	Approved
0.6973	Remote Similarity	NPD7700	Phase 2
0.6973	Remote Similarity	NPD7699	Phase 2
0.6962	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1283	Approved
0.6944	Remote Similarity	NPD8150	Discontinued
0.6933	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2861	Phase 2
0.6919	Remote Similarity	NPD7199	Phase 2
0.6914	Remote Similarity	NPD7228	Approved
0.6909	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD920	Approved
0.6905	Remote Similarity	NPD6801	Discontinued
0.6905	Remote Similarity	NPD37	Approved
0.6903	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6798	Discontinued
0.6901	Remote Similarity	NPD6234	Discontinued
0.6899	Remote Similarity	NPD7097	Phase 1
0.6894	Remote Similarity	NPD1243	Approved
0.689	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4966	Approved
0.6882	Remote Similarity	NPD4967	Phase 2
0.6882	Remote Similarity	NPD4965	Approved
0.6879	Remote Similarity	NPD7229	Phase 3
0.6871	Remote Similarity	NPD7440	Discontinued
0.6871	Remote Similarity	NPD3300	Phase 2
0.6867	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1610	Phase 2
0.6849	Remote Similarity	NPD709	Approved
0.6846	Remote Similarity	NPD17	Approved
0.6842	Remote Similarity	NPD1876	Approved
0.6839	Remote Similarity	NPD3926	Phase 2
0.6839	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD74	Approved
0.6831	Remote Similarity	NPD9266	Approved
0.6821	Remote Similarity	NPD1247	Approved
0.6818	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4060	Phase 1
0.6809	Remote Similarity	NPD968	Approved
0.6807	Remote Similarity	NPD7427	Discontinued
0.6796	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6585	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