NPASS Compound

Structure

NPC312482 OpenBabel07101718242D 27 29 0 0 1 0 0 0 0 0999 V2000 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 -1.0000 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 4.3301 -1.5000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 2.5981 0.5000 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 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 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 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 4.3301 -2.5000 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 3 26 1 0 0 0 0 4 8 1 0 0 0 0 4 9 2 0 0 0 0 5 7 1 0 0 0 0 5 18 1 0 0 0 0 6 19 2 0 0 0 0 6 27 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 8 20 2 0 0 0 0 9 14 1 0 0 0 0 9 26 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 18 1 1 0 0 0 17 27 1 0 0 0 0 18 2 1 6 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.1
Volume:	354.872
LogP:	2.527
LogD:	1.291
LogS:	-2.88
# Rotatable Bonds:	3
TPSA:	153.75
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	3.921
Fsp3:	0.333
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:	-5.637
MDCK Permeability:	5.027025963499909e-06
Pgp-inhibitor:	0.094
Pgp-substrate:	0.153
Human Intestinal Absorption (HIA):	0.363
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	93.50750732421875%
Volume Distribution (VD):	1.008
Pgp-substrate:	11.24266242980957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.4
CYP1A2-substrate:	0.772
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.158
CYP2C9-substrate:	0.355
CYP2D6-inhibitor:	0.091
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.129
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	4.025
Half-life (T1/2):	0.675

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.553
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.7
Carcinogencity:	0.026
Eye Corrosion:	0.005
Eye Irritation:	0.457
Respiratory Toxicity:	0.191

Download Data

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

Natural Product: NPC312482

Natural Product ID:	NPC312482
*Common Name:**	3-Acetoxybostrycin
IUPAC Name:	[(1S,2R,3S)-1,3,9,10-tetrahydroxy-6-methoxy-3-methyl-5,8-dioxo-2,4-dihydro-1H-anthracen-2-yl] acetate
Synonyms:	3-Acetoxybostrycin
Standard InCHIKey:	DVJQEKCWICUQJN-KSZLIROESA-N
Standard InCHI:	InChI=1S/C18H18O9/c1-6(19)27-17-16(24)10-7(5-18(17,2)25)13(21)12-11(15(10)23)8(20)4-9(26-3)14(12)22/h4,16-17,21,23-25H,5H2,1-3H3/t16-,17+,18-/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@H](c2c(C[C@]1(C)O)c(c1c(C(=O)C=C(C1=O)OC)c2O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047318
PubChem CID:	59052028
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

Activity Type	# Activity
Cell Line	1
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2720.0	nM	PMID[538483]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	200000.0	nM	PMID[538483]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3120.0	nM	PMID[538483]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	200000.0	nM	PMID[538483]
NPT5776	Organism	Streptomyces albus	Streptomyces albus	MIC	>	200000.0	nM	PMID[538483]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	200000.0	nM	PMID[538483]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	=	3120.0	nM	PMID[538483]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	200000.0	nM	PMID[538483]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	>	200000.0	nM	PMID[538483]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	>	200000.0	nM	PMID[538483]

☑ 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 NPC312482 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	352
0.1-0.2	1431
0.2-0.3	3284
0.3-0.4	7583
0.4-0.5	10722
0.5-0.6	6409
0.6-0.7	6989
0.7-0.8	5615
0.8-0.85	280
0.85-0.9	26
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9658	High Similarity	NPC470479
0.9658	High Similarity	NPC112816
0.9315	High Similarity	NPC143898
0.9128	High Similarity	NPC136878
0.8993	High Similarity	NPC29932
0.8947	High Similarity	NPC44378
0.8947	High Similarity	NPC280753
0.8882	High Similarity	NPC473095
0.8882	High Similarity	NPC473096
0.8831	High Similarity	NPC205918
0.882	High Similarity	NPC473094
0.8773	High Similarity	NPC473113
0.8758	High Similarity	NPC94781
0.8726	High Similarity	NPC478027
0.8718	High Similarity	NPC474824
0.8718	High Similarity	NPC470408
0.8718	High Similarity	NPC182921
0.8718	High Similarity	NPC218870
0.8718	High Similarity	NPC471695
0.8701	High Similarity	NPC120171
0.8671	High Similarity	NPC472889
0.8662	High Similarity	NPC314257
0.8625	High Similarity	NPC117985
0.8608	High Similarity	NPC474861
0.8598	High Similarity	NPC470580
0.858	High Similarity	NPC472049
0.858	High Similarity	NPC329647
0.858	High Similarity	NPC470735
0.8562	High Similarity	NPC88864
0.8562	High Similarity	NPC474630
0.8554	High Similarity	NPC19056
0.8554	High Similarity	NPC470583
0.8553	High Similarity	NPC469885
0.8545	High Similarity	NPC270027
0.8544	High Similarity	NPC478221
0.8543	High Similarity	NPC283292
0.8497	Intermediate Similarity	NPC475813
0.8481	Intermediate Similarity	NPC478231
0.8481	Intermediate Similarity	NPC137301
0.8476	Intermediate Similarity	NPC107009
0.8462	Intermediate Similarity	NPC208069
0.8462	Intermediate Similarity	NPC474310
0.8452	Intermediate Similarity	NPC470582
0.8452	Intermediate Similarity	NPC266513
0.8452	Intermediate Similarity	NPC470581
0.8452	Intermediate Similarity	NPC115447
0.8447	Intermediate Similarity	NPC472055
0.8447	Intermediate Similarity	NPC284495
0.8438	Intermediate Similarity	NPC246466
0.8428	Intermediate Similarity	NPC69043
0.8428	Intermediate Similarity	NPC170189
0.8428	Intermediate Similarity	NPC478230
0.8428	Intermediate Similarity	NPC317585
0.8428	Intermediate Similarity	NPC208173
0.8428	Intermediate Similarity	NPC472890
0.8428	Intermediate Similarity	NPC471456
0.8418	Intermediate Similarity	NPC478224
0.8418	Intermediate Similarity	NPC115249
0.8415	Intermediate Similarity	NPC20237
0.8402	Intermediate Similarity	NPC283980
0.8402	Intermediate Similarity	NPC187441
0.8387	Intermediate Similarity	NPC285122
0.8387	Intermediate Similarity	NPC63918
0.8385	Intermediate Similarity	NPC470339
0.8382	Intermediate Similarity	NPC314672
0.8378	Intermediate Similarity	NPC193169
0.8377	Intermediate Similarity	NPC103910
0.8375	Intermediate Similarity	NPC472050
0.8364	Intermediate Similarity	NPC283041
0.8354	Intermediate Similarity	NPC478026
0.8343	Intermediate Similarity	NPC83331
0.8343	Intermediate Similarity	NPC477682
0.8343	Intermediate Similarity	NPC477683
0.8323	Intermediate Similarity	NPC183441
0.8323	Intermediate Similarity	NPC294501
0.8323	Intermediate Similarity	NPC478225
0.8323	Intermediate Similarity	NPC302258
0.8323	Intermediate Similarity	NPC474309
0.8313	Intermediate Similarity	NPC3449
0.8313	Intermediate Similarity	NPC328321
0.8304	Intermediate Similarity	NPC475656
0.8304	Intermediate Similarity	NPC182693
0.8304	Intermediate Similarity	NPC475148
0.8302	Intermediate Similarity	NPC184284
0.8302	Intermediate Similarity	NPC76041
0.8301	Intermediate Similarity	NPC257003
0.8293	Intermediate Similarity	NPC249181
0.8291	Intermediate Similarity	NPC472891
0.8291	Intermediate Similarity	NPC315520
0.8282	Intermediate Similarity	NPC317544
0.8282	Intermediate Similarity	NPC316457
0.828	Intermediate Similarity	NPC470359
0.8274	Intermediate Similarity	NPC476311
0.8269	Intermediate Similarity	NPC120536
0.8263	Intermediate Similarity	NPC478021
0.8263	Intermediate Similarity	NPC313717
0.8263	Intermediate Similarity	NPC315306
0.8258	Intermediate Similarity	NPC471906
0.8258	Intermediate Similarity	NPC244691
0.825	Intermediate Similarity	NPC155686
0.825	Intermediate Similarity	NPC472211
0.8247	Intermediate Similarity	NPC474300
0.8242	Intermediate Similarity	NPC478022
0.8242	Intermediate Similarity	NPC21016
0.8242	Intermediate Similarity	NPC478020
0.8242	Intermediate Similarity	NPC146584
0.8242	Intermediate Similarity	NPC191930
0.8239	Intermediate Similarity	NPC91809
0.8239	Intermediate Similarity	NPC314020
0.8225	Intermediate Similarity	NPC162248
0.8225	Intermediate Similarity	NPC294149
0.8224	Intermediate Similarity	NPC173980
0.8214	Intermediate Similarity	NPC472620
0.8214	Intermediate Similarity	NPC158226
0.8212	Intermediate Similarity	NPC315275
0.821	Intermediate Similarity	NPC208651
0.821	Intermediate Similarity	NPC478226
0.821	Intermediate Similarity	NPC206641
0.8205	Intermediate Similarity	NPC170055
0.8205	Intermediate Similarity	NPC475923
0.8204	Intermediate Similarity	NPC49487
0.8204	Intermediate Similarity	NPC99613
0.8199	Intermediate Similarity	NPC326910
0.8199	Intermediate Similarity	NPC68727
0.8194	Intermediate Similarity	NPC476473
0.8187	Intermediate Similarity	NPC180388
0.8187	Intermediate Similarity	NPC478220
0.8187	Intermediate Similarity	NPC473607
0.8187	Intermediate Similarity	NPC470340
0.8182	Intermediate Similarity	NPC208120
0.8182	Intermediate Similarity	NPC173587
0.8182	Intermediate Similarity	NPC29055
0.8176	Intermediate Similarity	NPC164762
0.8176	Intermediate Similarity	NPC56204
0.8176	Intermediate Similarity	NPC176246
0.8171	Intermediate Similarity	NPC87431
0.8171	Intermediate Similarity	NPC318081
0.8171	Intermediate Similarity	NPC269117
0.817	Intermediate Similarity	NPC29771
0.817	Intermediate Similarity	NPC306835
0.817	Intermediate Similarity	NPC114620
0.817	Intermediate Similarity	NPC476477
0.817	Intermediate Similarity	NPC299405
0.817	Intermediate Similarity	NPC103337
0.817	Intermediate Similarity	NPC216312
0.817	Intermediate Similarity	NPC471602
0.817	Intermediate Similarity	NPC256463
0.817	Intermediate Similarity	NPC111422
0.8166	Intermediate Similarity	NPC472054
0.8166	Intermediate Similarity	NPC154986
0.8161	Intermediate Similarity	NPC174486
0.816	Intermediate Similarity	NPC477410
0.8151	Intermediate Similarity	NPC472047
0.8141	Intermediate Similarity	NPC218866
0.8141	Intermediate Similarity	NPC84568
0.8141	Intermediate Similarity	NPC48130
0.8141	Intermediate Similarity	NPC300684
0.814	Intermediate Similarity	NPC315221
0.8137	Intermediate Similarity	NPC205172
0.8137	Intermediate Similarity	NPC192189
0.8137	Intermediate Similarity	NPC474621
0.8137	Intermediate Similarity	NPC474622
0.8137	Intermediate Similarity	NPC209393
0.8133	Intermediate Similarity	NPC472057
0.8133	Intermediate Similarity	NPC472051
0.8129	Intermediate Similarity	NPC476210
0.8129	Intermediate Similarity	NPC476199
0.8129	Intermediate Similarity	NPC470334
0.8129	Intermediate Similarity	NPC135524
0.8125	Intermediate Similarity	NPC132990
0.8125	Intermediate Similarity	NPC46882
0.8118	Intermediate Similarity	NPC245975
0.8118	Intermediate Similarity	NPC68381
0.8118	Intermediate Similarity	NPC86809
0.8118	Intermediate Similarity	NPC232412
0.8118	Intermediate Similarity	NPC98667
0.8117	Intermediate Similarity	NPC327916
0.8117	Intermediate Similarity	NPC241349
0.8117	Intermediate Similarity	NPC220496
0.8117	Intermediate Similarity	NPC147542
0.8117	Intermediate Similarity	NPC32749
0.8117	Intermediate Similarity	NPC42262
0.8117	Intermediate Similarity	NPC37992
0.8113	Intermediate Similarity	NPC84142
0.811	Intermediate Similarity	NPC155302
0.811	Intermediate Similarity	NPC161947
0.811	Intermediate Similarity	NPC470358
0.8103	Intermediate Similarity	NPC197972
0.8101	Intermediate Similarity	NPC166583
0.8101	Intermediate Similarity	NPC476821
0.8101	Intermediate Similarity	NPC8817
0.8101	Intermediate Similarity	NPC53362
0.8098	Intermediate Similarity	NPC29552
0.8098	Intermediate Similarity	NPC263483
0.8095	Intermediate Similarity	NPC165979
0.8095	Intermediate Similarity	NPC213416
0.8095	Intermediate Similarity	NPC175477
0.8095	Intermediate Similarity	NPC163130
0.8095	Intermediate Similarity	NPC472619
0.8095	Intermediate Similarity	NPC191653

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 NPC312482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	1010
0.2-0.3	2077
0.3-0.4	2760
0.4-0.5	1789
0.5-0.6	820
0.6-0.7	290
0.7-0.8	92
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8372	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD8150	Discontinued
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7912	Intermediate Similarity	NPD7435	Discontinued
0.7904	Intermediate Similarity	NPD6232	Discontinued
0.7879	Intermediate Similarity	NPD7075	Discontinued
0.787	Intermediate Similarity	NPD7473	Discontinued
0.7865	Intermediate Similarity	NPD6534	Approved
0.7865	Intermediate Similarity	NPD6535	Approved
0.7853	Intermediate Similarity	NPD6801	Discontinued
0.7758	Intermediate Similarity	NPD5402	Approved
0.7747	Intermediate Similarity	NPD6778	Approved
0.7747	Intermediate Similarity	NPD6780	Approved
0.7747	Intermediate Similarity	NPD6782	Approved
0.7747	Intermediate Similarity	NPD6776	Approved
0.7747	Intermediate Similarity	NPD6781	Approved
0.7747	Intermediate Similarity	NPD6777	Approved
0.7747	Intermediate Similarity	NPD6779	Approved
0.7742	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7699	Phase 2
0.7735	Intermediate Similarity	NPD7700	Phase 2
0.7697	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5844	Phase 1
0.7673	Intermediate Similarity	NPD6190	Approved
0.766	Intermediate Similarity	NPD7874	Approved
0.766	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8434	Phase 2
0.7622	Intermediate Similarity	NPD4380	Phase 2
0.76	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7819	Suspended
0.7581	Intermediate Similarity	NPD8320	Phase 1
0.7581	Intermediate Similarity	NPD8319	Approved
0.7561	Intermediate Similarity	NPD3226	Approved
0.7545	Intermediate Similarity	NPD3817	Phase 2
0.7529	Intermediate Similarity	NPD6959	Discontinued
0.7527	Intermediate Similarity	NPD7696	Phase 3
0.7527	Intermediate Similarity	NPD7697	Approved
0.7527	Intermediate Similarity	NPD7698	Approved
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7485	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7390	Discontinued
0.7468	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD5404	Approved
0.7468	Intermediate Similarity	NPD5408	Approved
0.746	Intermediate Similarity	NPD7701	Phase 2
0.7423	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6166	Phase 2
0.7396	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3882	Suspended
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.7381	Intermediate Similarity	NPD2801	Approved
0.7371	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6799	Approved
0.736	Intermediate Similarity	NPD8313	Approved
0.736	Intermediate Similarity	NPD8312	Approved
0.7358	Intermediate Similarity	NPD2935	Discontinued
0.7345	Intermediate Similarity	NPD6559	Discontinued
0.7344	Intermediate Similarity	NPD7801	Approved
0.7333	Intermediate Similarity	NPD5403	Approved
0.7322	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6213	Phase 3
0.7322	Intermediate Similarity	NPD6212	Phase 3
0.7321	Intermediate Similarity	NPD1934	Approved
0.7317	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD3818	Discontinued
0.7312	Intermediate Similarity	NPD2346	Discontinued
0.7301	Intermediate Similarity	NPD3300	Phase 2
0.7296	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6797	Phase 2
0.7288	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5494	Approved
0.7263	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1470	Approved
0.7251	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7251	Discontinued
0.724	Intermediate Similarity	NPD8151	Discontinued
0.7222	Intermediate Similarity	NPD2800	Approved
0.7212	Intermediate Similarity	NPD5401	Approved
0.7209	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7808	Phase 3
0.7196	Intermediate Similarity	NPD6823	Phase 2
0.7184	Intermediate Similarity	NPD3787	Discontinued
0.7178	Intermediate Similarity	NPD4628	Phase 3
0.7176	Intermediate Similarity	NPD1465	Phase 2
0.716	Intermediate Similarity	NPD7411	Suspended
0.7152	Intermediate Similarity	NPD943	Approved
0.7151	Intermediate Similarity	NPD8368	Discontinued
0.7135	Intermediate Similarity	NPD7074	Phase 3
0.7134	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD230	Phase 1
0.7079	Intermediate Similarity	NPD7054	Approved
0.7066	Intermediate Similarity	NPD1512	Approved
0.7063	Intermediate Similarity	NPD6651	Approved
0.7039	Intermediate Similarity	NPD7472	Approved
0.7035	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8407	Phase 2
0.7018	Intermediate Similarity	NPD37	Approved
0.7017	Intermediate Similarity	NPD4955	Approved
0.7017	Intermediate Similarity	NPD4954	Approved
0.7017	Intermediate Similarity	NPD5034	Approved
0.7017	Intermediate Similarity	NPD36	Approved
0.7017	Intermediate Similarity	NPD5026	Approved
0.7017	Intermediate Similarity	NPD5028	Approved
0.7011	Intermediate Similarity	NPD6234	Discontinued
0.7006	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4966	Approved
0.6994	Remote Similarity	NPD4965	Approved
0.6994	Remote Similarity	NPD4967	Phase 2
0.6993	Remote Similarity	NPD1201	Approved
0.699	Remote Similarity	NPD7783	Phase 2
0.699	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1510	Phase 2
0.697	Remote Similarity	NPD3750	Approved
0.697	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5030	Phase 2
0.6957	Remote Similarity	NPD1607	Approved
0.6957	Remote Similarity	NPD5038	Approved
0.6957	Remote Similarity	NPD5037	Approved
0.6954	Remote Similarity	NPD3749	Approved
0.6951	Remote Similarity	NPD1549	Phase 2
0.6946	Remote Similarity	NPD1511	Approved
0.6941	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1247	Approved
0.6927	Remote Similarity	NPD7799	Discontinued
0.6918	Remote Similarity	NPD7985	Registered
0.6914	Remote Similarity	NPD919	Approved
0.6909	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5036	Approved
0.6897	Remote Similarity	NPD7768	Phase 2
0.689	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7236	Approved
0.6885	Remote Similarity	NPD5035	Approved
0.6882	Remote Similarity	NPD8435	Approved
0.6882	Remote Similarity	NPD7239	Suspended
0.6882	Remote Similarity	NPD8361	Approved
0.6882	Remote Similarity	NPD8360	Approved
0.6867	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7228	Approved
0.6832	Remote Similarity	NPD1240	Approved
0.6829	Remote Similarity	NPD2796	Approved
0.6829	Remote Similarity	NPD1551	Phase 2
0.6821	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3764	Approved
0.6813	Remote Similarity	NPD2313	Discontinued
0.6813	Remote Similarity	NPD5953	Discontinued
0.6771	Remote Similarity	NPD8285	Discontinued
0.6768	Remote Similarity	NPD2799	Discontinued
0.6766	Remote Similarity	NPD8166	Discontinued
0.6765	Remote Similarity	NPD8366	Approved
0.676	Remote Similarity	NPD3926	Phase 2
0.676	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD8485	Approved
0.6744	Remote Similarity	NPD7458	Discontinued
0.6731	Remote Similarity	NPD9269	Phase 2
0.6728	Remote Similarity	NPD4060	Phase 1
0.6728	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6100	Approved
0.6727	Remote Similarity	NPD6099	Approved
0.6725	Remote Similarity	NPD920	Approved
0.6709	Remote Similarity	NPD1164	Approved
0.6706	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7286	Phase 2
0.6687	Remote Similarity	NPD447	Suspended
0.6685	Remote Similarity	NPD5027	Approved
0.6685	Remote Similarity	NPD5029	Approved
0.6685	Remote Similarity	NPD5031	Approved
0.6685	Remote Similarity	NPD7685	Pre-registration
0.6683	Remote Similarity	NPD8059	Phase 3
0.6683	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8404	Phase 2
0.6649	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7199	Phase 2
0.6635	Remote Similarity	NPD8491	Approved
0.6628	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD6765	Approved
0.6595	Remote Similarity	NPD6764	Approved
0.6587	Remote Similarity	NPD1471	Phase 3
0.6587	Remote Similarity	NPD7266	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