NPASS Compound

Structure

NPC470479 OpenBabel07101718192D 26 28 0 0 1 0 0 0 0 0999 V2000 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -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 0.0000 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 -4.3301 1.5000 0.0000 C 0 0 2 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 -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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 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 -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 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -0.3660 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 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 3 25 1 0 0 0 0 4 8 1 0 0 0 0 4 12 1 0 0 0 0 5 10 1 0 0 0 0 5 11 2 0 0 0 0 6 9 1 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 7 26 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 13 1 0 0 0 0 10 20 2 0 0 0 0 11 17 1 0 0 0 0 11 25 1 0 0 0 0 12 18 1 6 0 0 0 12 26 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 18 2 1 1 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.1
Volume:	346.081
LogP:	1.695
LogD:	1.192
LogS:	-2.949
# Rotatable Bonds:	3
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	4.246
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.645
MDCK Permeability:	8.640003215987235e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.151
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.076

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	92.5743637084961%
Volume Distribution (VD):	1.09
Pgp-substrate:	12.348483085632324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.834
CYP1A2-substrate:	0.668
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.666
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	2.908
Half-life (T1/2):	0.922

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.735
AMES Toxicity:	0.561
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.183
Skin Sensitization:	0.424
Carcinogencity:	0.539
Eye Corrosion:	0.046
Eye Irritation:	0.466
Respiratory Toxicity:	0.377

Download Data

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

Natural Product: NPC470479

Natural Product ID:	NPC470479
*Common Name:**	3-Acetoxy-4-Deoxybostrycin
IUPAC Name:	[(2R,3S)-3,9,10-trihydroxy-6-methoxy-3-methyl-5,8-dioxo-2,4-dihydro-1H-anthracen-2-yl] acetate
Synonyms:
Standard InCHIKey:	CYLITUIHHYZDPV-XIKOKIGWSA-N
Standard InCHI:	InChI=1S/C18H18O8/c1-7(19)26-12-4-8-9(6-18(12,2)24)16(22)14-13(15(8)21)10(20)5-11(25-3)17(14)23/h5,12,21-22,24H,4,6H2,1-3H3/t12-,18+/m1/s1
SMILES:	COC1=CC(=O)c2c(C1=O)c(O)c1c(c2O)C[C@H]([C@@](C1)(C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047317
PubChem CID:	59051897
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO33050	nigrospora sp.	Species	Trichosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22545792]

☑ 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
MIC	9
Others	1

Activity Type	# Activity
Cell Line	1
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5250.0	nM	PMID[501033]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	780.0	nM	PMID[501033]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	48.8	nM	PMID[501033]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	100000.0	nM	PMID[501033]
NPT5776	Organism	Streptomyces albus	Streptomyces albus	MIC	=	200000.0	nM	PMID[501033]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	200000.0	nM	PMID[501033]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	=	195.0	nM	PMID[501033]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	200000.0	nM	PMID[501033]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	=	97.5	nM	PMID[501033]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	=	780.0	nM	PMID[501033]
NPT314	Organism	Bacillus cereus	Bacillus cereus	Ratio	=	25.0	n.a.	PMID[501033]

☑ 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 NPC470479 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	337
0.1-0.2	1388
0.2-0.3	3190
0.3-0.4	7539
0.4-0.5	11103
0.5-0.6	6553
0.6-0.7	8365
0.7-0.8	4078
0.8-0.85	126
0.85-0.9	12
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9658	High Similarity	NPC312482
0.9507	High Similarity	NPC143898
0.9315	High Similarity	NPC112816
0.9172	High Similarity	NPC29932
0.8993	High Similarity	NPC280753
0.8993	High Similarity	NPC44378
0.8919	High Similarity	NPC136878
0.88	High Similarity	NPC94781
0.8742	High Similarity	NPC120171
0.8732	High Similarity	NPC88864
0.8671	High Similarity	NPC193169
0.8627	High Similarity	NPC205918
0.8618	High Similarity	NPC474310
0.86	High Similarity	NPC474309
0.8591	High Similarity	NPC469885
0.8581	High Similarity	NPC283292
0.858	High Similarity	NPC473113
0.8571	High Similarity	NPC473096
0.8571	High Similarity	NPC473095
0.8526	High Similarity	NPC478027
0.8523	High Similarity	NPC474300
0.8509	High Similarity	NPC473094
0.8477	Intermediate Similarity	NPC475923
0.8477	Intermediate Similarity	NPC474630
0.8467	Intermediate Similarity	NPC476473
0.8456	Intermediate Similarity	NPC257003
0.8446	Intermediate Similarity	NPC111422
0.8446	Intermediate Similarity	NPC306835
0.8446	Intermediate Similarity	NPC476477
0.8446	Intermediate Similarity	NPC299405
0.8446	Intermediate Similarity	NPC216312
0.8446	Intermediate Similarity	NPC29771
0.8446	Intermediate Similarity	NPC471602
0.8446	Intermediate Similarity	NPC256463
0.8421	Intermediate Similarity	NPC63918
0.8411	Intermediate Similarity	NPC475813
0.8411	Intermediate Similarity	NPC103910
0.8397	Intermediate Similarity	NPC471695
0.8397	Intermediate Similarity	NPC474824
0.8397	Intermediate Similarity	NPC470408
0.8397	Intermediate Similarity	NPC218870
0.8397	Intermediate Similarity	NPC182921
0.8389	Intermediate Similarity	NPC241349
0.8389	Intermediate Similarity	NPC37992
0.8389	Intermediate Similarity	NPC147542
0.8389	Intermediate Similarity	NPC32749
0.8389	Intermediate Similarity	NPC327916
0.8389	Intermediate Similarity	NPC220496
0.8389	Intermediate Similarity	NPC42262
0.8385	Intermediate Similarity	NPC329647
0.8385	Intermediate Similarity	NPC470735
0.8354	Intermediate Similarity	NPC472889
0.8354	Intermediate Similarity	NPC270027
0.8345	Intermediate Similarity	NPC309430
0.8344	Intermediate Similarity	NPC314257
0.8344	Intermediate Similarity	NPC471456
0.8344	Intermediate Similarity	NPC478221
0.8333	Intermediate Similarity	NPC471444
0.8333	Intermediate Similarity	NPC180388
0.8323	Intermediate Similarity	NPC315520
0.8323	Intermediate Similarity	NPC31132
0.8322	Intermediate Similarity	NPC114620
0.8322	Intermediate Similarity	NPC103337
0.8313	Intermediate Similarity	NPC117985
0.8313	Intermediate Similarity	NPC318081
0.8301	Intermediate Similarity	NPC285122
0.8293	Intermediate Similarity	NPC470580
0.8291	Intermediate Similarity	NPC474861
0.8289	Intermediate Similarity	NPC274085
0.8289	Intermediate Similarity	NPC89664
0.8288	Intermediate Similarity	NPC254603
0.828	Intermediate Similarity	NPC137301
0.828	Intermediate Similarity	NPC478231
0.8272	Intermediate Similarity	NPC472049
0.8253	Intermediate Similarity	NPC470583
0.8253	Intermediate Similarity	NPC19056
0.8247	Intermediate Similarity	NPC476821
0.8228	Intermediate Similarity	NPC472890
0.8228	Intermediate Similarity	NPC3449
0.8228	Intermediate Similarity	NPC317585
0.8224	Intermediate Similarity	NPC21873
0.8217	Intermediate Similarity	NPC115249
0.8207	Intermediate Similarity	NPC198305
0.82	Intermediate Similarity	NPC295339
0.8182	Intermediate Similarity	NPC120536
0.8176	Intermediate Similarity	NPC472050
0.8171	Intermediate Similarity	NPC107009
0.817	Intermediate Similarity	NPC477409
0.8166	Intermediate Similarity	NPC208069
0.8165	Intermediate Similarity	NPC474621
0.8165	Intermediate Similarity	NPC474622
0.816	Intermediate Similarity	NPC478026
0.816	Intermediate Similarity	NPC474301
0.8158	Intermediate Similarity	NPC308572
0.8155	Intermediate Similarity	NPC83331
0.8155	Intermediate Similarity	NPC477683
0.8155	Intermediate Similarity	NPC266513
0.8155	Intermediate Similarity	NPC477682
0.8155	Intermediate Similarity	NPC470581
0.8155	Intermediate Similarity	NPC470582
0.8155	Intermediate Similarity	NPC115447
0.8146	Intermediate Similarity	NPC315578
0.8138	Intermediate Similarity	NPC278928
0.8137	Intermediate Similarity	NPC284495
0.8137	Intermediate Similarity	NPC472055
0.8133	Intermediate Similarity	NPC61590
0.8133	Intermediate Similarity	NPC173980
0.8133	Intermediate Similarity	NPC183441
0.8129	Intermediate Similarity	NPC5568
0.8125	Intermediate Similarity	NPC302258
0.8125	Intermediate Similarity	NPC208651
0.8125	Intermediate Similarity	NPC246466
0.8125	Intermediate Similarity	NPC29552
0.8125	Intermediate Similarity	NPC206641
0.8125	Intermediate Similarity	NPC478225
0.8121	Intermediate Similarity	NPC474311
0.8121	Intermediate Similarity	NPC315275
0.8118	Intermediate Similarity	NPC475656
0.8118	Intermediate Similarity	NPC475148
0.8118	Intermediate Similarity	NPC182693
0.8117	Intermediate Similarity	NPC170055
0.8113	Intermediate Similarity	NPC170189
0.8113	Intermediate Similarity	NPC478230
0.8113	Intermediate Similarity	NPC208173
0.8113	Intermediate Similarity	NPC69043
0.811	Intermediate Similarity	NPC20237
0.8107	Intermediate Similarity	NPC283980
0.8107	Intermediate Similarity	NPC187441
0.8101	Intermediate Similarity	NPC478224
0.8101	Intermediate Similarity	NPC76041
0.8101	Intermediate Similarity	NPC184284
0.8098	Intermediate Similarity	NPC249181
0.8095	Intermediate Similarity	NPC110609
0.8095	Intermediate Similarity	NPC246693
0.8095	Intermediate Similarity	NPC242358
0.8092	Intermediate Similarity	NPC314672
0.8089	Intermediate Similarity	NPC472891
0.8079	Intermediate Similarity	NPC26924
0.8075	Intermediate Similarity	NPC470339
0.8067	Intermediate Similarity	NPC305060
0.8065	Intermediate Similarity	NPC147250
0.8063	Intermediate Similarity	NPC478223
0.8061	Intermediate Similarity	NPC283041
0.8061	Intermediate Similarity	NPC471295
0.8052	Intermediate Similarity	NPC48130
0.8052	Intermediate Similarity	NPC218866
0.8052	Intermediate Similarity	NPC79627
0.8052	Intermediate Similarity	NPC84568
0.8052	Intermediate Similarity	NPC300684
0.805	Intermediate Similarity	NPC209393
0.805	Intermediate Similarity	NPC205172
0.8049	Intermediate Similarity	NPC191930
0.8041	Intermediate Similarity	NPC171968
0.8036	Intermediate Similarity	NPC162248
0.8026	Intermediate Similarity	NPC3218
0.8025	Intermediate Similarity	NPC478219
0.8024	Intermediate Similarity	NPC294501
0.8024	Intermediate Similarity	NPC158226
0.8013	Intermediate Similarity	NPC119767
0.8012	Intermediate Similarity	NPC478226
0.8012	Intermediate Similarity	NPC175477
0.8012	Intermediate Similarity	NPC49487
0.8012	Intermediate Similarity	NPC67197
0.8012	Intermediate Similarity	NPC328321
0.8012	Intermediate Similarity	NPC99613
0.8	Intermediate Similarity	NPC192219
0.8	Intermediate Similarity	NPC174599
0.8	Intermediate Similarity	NPC326910
0.8	Intermediate Similarity	NPC82190
0.8	Intermediate Similarity	NPC66029
0.8	Intermediate Similarity	NPC478133
0.7988	Intermediate Similarity	NPC208120
0.7988	Intermediate Similarity	NPC176246
0.7988	Intermediate Similarity	NPC29055
0.7988	Intermediate Similarity	NPC173587
0.7988	Intermediate Similarity	NPC477689
0.7987	Intermediate Similarity	NPC474533
0.7987	Intermediate Similarity	NPC478220
0.7987	Intermediate Similarity	NPC474534
0.7987	Intermediate Similarity	NPC477690
0.7977	Intermediate Similarity	NPC174486
0.7976	Intermediate Similarity	NPC65118
0.7976	Intermediate Similarity	NPC476311
0.7976	Intermediate Similarity	NPC154986
0.7975	Intermediate Similarity	NPC269117
0.7975	Intermediate Similarity	NPC164762
0.7975	Intermediate Similarity	NPC317544
0.7975	Intermediate Similarity	NPC478134
0.7975	Intermediate Similarity	NPC316457
0.7964	Intermediate Similarity	NPC315306
0.7964	Intermediate Similarity	NPC478021
0.7964	Intermediate Similarity	NPC313717
0.7963	Intermediate Similarity	NPC314795
0.7962	Intermediate Similarity	NPC101043
0.7962	Intermediate Similarity	NPC470359
0.7962	Intermediate Similarity	NPC306799
0.7955	Intermediate Similarity	NPC314020
0.7953	Intermediate Similarity	NPC475996
0.795	Intermediate Similarity	NPC283480
0.795	Intermediate Similarity	NPC148323

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 NPC470479 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	985
0.2-0.3	1983
0.3-0.4	2729
0.4-0.5	1903
0.5-0.6	864
0.6-0.7	311
0.7-0.8	76
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8081	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD8150	Discontinued
0.7861	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD2533	Approved
0.7771	Intermediate Similarity	NPD2534	Approved
0.7771	Intermediate Similarity	NPD2532	Approved
0.7711	Intermediate Similarity	NPD6232	Discontinued
0.7683	Intermediate Similarity	NPD7075	Discontinued
0.7679	Intermediate Similarity	NPD7473	Discontinued
0.7658	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD7435	Discontinued
0.7584	Intermediate Similarity	NPD6535	Approved
0.7584	Intermediate Similarity	NPD6534	Approved
0.7561	Intermediate Similarity	NPD5402	Approved
0.7548	Intermediate Similarity	NPD2346	Discontinued
0.7546	Intermediate Similarity	NPD6801	Discontinued
0.7532	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.7484	Intermediate Similarity	NPD5404	Approved
0.7484	Intermediate Similarity	NPD5406	Approved
0.7484	Intermediate Similarity	NPD5408	Approved
0.7484	Intermediate Similarity	NPD5405	Approved
0.7473	Intermediate Similarity	NPD6778	Approved
0.7473	Intermediate Similarity	NPD6779	Approved
0.7473	Intermediate Similarity	NPD6781	Approved
0.7473	Intermediate Similarity	NPD6780	Approved
0.7473	Intermediate Similarity	NPD6782	Approved
0.7473	Intermediate Similarity	NPD6777	Approved
0.7473	Intermediate Similarity	NPD6776	Approved
0.7468	Intermediate Similarity	NPD6190	Approved
0.7459	Intermediate Similarity	NPD7699	Phase 2
0.7459	Intermediate Similarity	NPD7700	Phase 2
0.7443	Intermediate Similarity	NPD8434	Phase 2
0.7394	Intermediate Similarity	NPD7874	Approved
0.7394	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7819	Suspended
0.7384	Intermediate Similarity	NPD5844	Phase 1
0.7372	Intermediate Similarity	NPD2935	Discontinued
0.7371	Intermediate Similarity	NPD8313	Approved
0.7371	Intermediate Similarity	NPD8312	Approved
0.7349	Intermediate Similarity	NPD3817	Phase 2
0.7337	Intermediate Similarity	NPD6959	Discontinued
0.7317	Intermediate Similarity	NPD6599	Discontinued
0.7317	Intermediate Similarity	NPD4380	Phase 2
0.7314	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8320	Phase 1
0.7312	Intermediate Similarity	NPD8319	Approved
0.7289	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7390	Discontinued
0.7258	Intermediate Similarity	NPD7696	Phase 3
0.7258	Intermediate Similarity	NPD7698	Approved
0.7258	Intermediate Similarity	NPD7697	Approved
0.7255	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1201	Approved
0.7225	Intermediate Similarity	NPD3751	Discontinued
0.7219	Intermediate Similarity	NPD7870	Phase 2
0.7219	Intermediate Similarity	NPD7871	Phase 2
0.7202	Intermediate Similarity	NPD3882	Suspended
0.7202	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7701	Phase 2
0.7193	Intermediate Similarity	NPD5710	Approved
0.7193	Intermediate Similarity	NPD5711	Approved
0.7191	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4628	Phase 3
0.7186	Intermediate Similarity	NPD2801	Approved
0.716	Intermediate Similarity	NPD6799	Approved
0.7159	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6213	Phase 3
0.7143	Intermediate Similarity	NPD6212	Phase 3
0.7134	Intermediate Similarity	NPD5403	Approved
0.7126	Intermediate Similarity	NPD1934	Approved
0.7118	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6166	Phase 2
0.711	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7801	Approved
0.7076	Intermediate Similarity	NPD5494	Approved
0.7063	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2313	Discontinued
0.7032	Intermediate Similarity	NPD7985	Registered
0.7032	Intermediate Similarity	NPD3764	Approved
0.7029	Intermediate Similarity	NPD3818	Discontinued
0.7022	Intermediate Similarity	NPD5028	Approved
0.7022	Intermediate Similarity	NPD5026	Approved
0.7022	Intermediate Similarity	NPD4954	Approved
0.7022	Intermediate Similarity	NPD4955	Approved
0.7022	Intermediate Similarity	NPD5034	Approved
0.7022	Intermediate Similarity	NPD36	Approved
0.7021	Intermediate Similarity	NPD6823	Phase 2
0.702	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2800	Approved
0.7019	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5401	Approved
0.7006	Intermediate Similarity	NPD6797	Phase 2
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1465	Phase 2
0.6981	Remote Similarity	NPD2799	Discontinued
0.6979	Remote Similarity	NPD8151	Discontinued
0.6975	Remote Similarity	NPD8166	Discontinued
0.6966	Remote Similarity	NPD5030	Phase 2
0.6966	Remote Similarity	NPD8368	Discontinued
0.6966	Remote Similarity	NPD7251	Discontinued
0.6964	Remote Similarity	NPD7411	Suspended
0.6961	Remote Similarity	NPD5037	Approved
0.6961	Remote Similarity	NPD5038	Approved
0.6959	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4060	Phase 1
0.6943	Remote Similarity	NPD943	Approved
0.6927	Remote Similarity	NPD7808	Phase 3
0.6919	Remote Similarity	NPD6234	Discontinued
0.6909	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5036	Approved
0.6899	Remote Similarity	NPD230	Phase 1
0.6897	Remote Similarity	NPD3787	Discontinued
0.6872	Remote Similarity	NPD5029	Approved
0.6872	Remote Similarity	NPD5031	Approved
0.6872	Remote Similarity	NPD5027	Approved
0.6871	Remote Similarity	NPD3750	Approved
0.6871	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1512	Approved
0.6855	Remote Similarity	NPD6651	Approved
0.6854	Remote Similarity	NPD7074	Phase 3
0.6851	Remote Similarity	NPD8407	Phase 2
0.6845	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7458	Discontinued
0.6842	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7799	Discontinued
0.6824	Remote Similarity	NPD37	Approved
0.6821	Remote Similarity	NPD7783	Phase 2
0.6821	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4967	Phase 2
0.6802	Remote Similarity	NPD4966	Approved
0.6802	Remote Similarity	NPD7768	Phase 2
0.6802	Remote Similarity	NPD4965	Approved
0.6798	Remote Similarity	NPD7054	Approved
0.6788	Remote Similarity	NPD7236	Approved
0.6786	Remote Similarity	NPD7239	Suspended
0.677	Remote Similarity	NPD1510	Phase 2
0.6768	Remote Similarity	NPD7003	Approved
0.6768	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3749	Approved
0.676	Remote Similarity	NPD7472	Approved
0.6752	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1607	Approved
0.6748	Remote Similarity	NPD1549	Phase 2
0.6747	Remote Similarity	NPD1511	Approved
0.6743	Remote Similarity	NPD1247	Approved
0.6728	Remote Similarity	NPD1551	Phase 2
0.6724	Remote Similarity	NPD919	Approved
0.671	Remote Similarity	NPD1164	Approved
0.6709	Remote Similarity	NPD6798	Discontinued
0.6703	Remote Similarity	NPD8361	Approved
0.6703	Remote Similarity	NPD8435	Approved
0.6703	Remote Similarity	NPD5035	Approved
0.6703	Remote Similarity	NPD8360	Approved
0.6687	Remote Similarity	NPD6355	Discontinued
0.6687	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD447	Suspended
0.6687	Remote Similarity	NPD5762	Approved
0.6687	Remote Similarity	NPD1471	Phase 3
0.6687	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5763	Approved
0.6684	Remote Similarity	NPD8285	Discontinued
0.6667	Remote Similarity	NPD5049	Phase 3
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD7282	Approved
0.6648	Remote Similarity	NPD7228	Approved
0.6648	Remote Similarity	NPD7177	Discontinued
0.6645	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD5968	Phase 3
0.663	Remote Similarity	NPD5953	Discontinued
0.6626	Remote Similarity	NPD2438	Suspended
0.6626	Remote Similarity	NPD2796	Approved
0.6625	Remote Similarity	NPD1240	Approved
0.6625	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5736	Approved
0.6623	Remote Similarity	NPD9545	Approved
0.6613	Remote Similarity	NPD6836	Approved
0.6593	Remote Similarity	NPD6765	Approved
0.6593	Remote Similarity	NPD6764	Approved
0.6593	Remote Similarity	NPD7685	Pre-registration
0.6585	Remote Similarity	NPD2344	Approved
0.6585	Remote Similarity	NPD7266	Discontinued
0.6579	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8485	Approved

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