NPASS Compound

Structure

CID314672 OpenBabel06191716122D 47 51 0 0 1 0 0 0 0 0999 V2000 -0.8494 -4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9456 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 3.4327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4937 -2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4937 -3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7950 -5.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 -6.8654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5481 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3975 -2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 -3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9456 -2.4519 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5481 -2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3975 -3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 -2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5481 -4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7950 -2.9423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7950 -3.9231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9456 -4.4135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6987 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 1.4712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5481 -5.3942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0962 -3.9231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8494 0.4904 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6987 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5481 0.4904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 1.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -1.4712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3975 -5.8846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 0.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6443 -2.4519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6443 -4.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9456 -5.3942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 -5.8846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -0.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0962 -2.9423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2469 -4.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 3 40 1 0 0 0 0 4 41 1 0 0 0 0 5 42 1 0 0 0 0 6 43 1 0 0 0 0 7 44 1 0 0 0 0 8 45 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 20 2 0 0 0 0 13 2 1 6 0 0 0 13 23 1 0 0 0 0 13 46 1 0 0 0 0 14 19 1 0 0 0 0 15 21 2 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 47 1 0 0 0 0 17 27 1 0 0 0 0 17 40 1 0 0 0 0 18 32 1 0 0 0 0 18 33 2 0 0 0 0 19 22 2 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 21 28 1 0 0 0 0 22 34 1 0 0 0 0 23 24 1 0 0 0 0 23 41 1 1 0 0 0 24 25 1 0 0 0 0 24 42 1 6 0 0 0 25 30 1 0 0 0 0 25 43 1 6 0 0 0 26 31 1 0 0 0 0 26 35 2 0 0 0 0 27 31 1 6 0 0 0 27 36 1 0 0 0 0 28 32 1 0 0 0 0 28 37 2 0 0 0 0 29 38 2 0 0 0 0 29 44 1 0 0 0 0 30 46 1 0 0 0 0 30 47 1 1 0 0 0 31 32 1 6 0 0 0 31 39 1 0 0 0 0 32 45 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	660.21
Volume:	624.735
LogP:	2.512
LogD:	2.165
LogS:	-3.965
# Rotatable Bonds:	9
TPSA:	199.65
# H-Bond Aceptor:	15
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	5.325
Fsp3:	0.531
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.508
MDCK Permeability:	2.9658480343641713e-05
Pgp-inhibitor:	0.917
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	78.8824234008789%
Volume Distribution (VD):	0.702
Pgp-substrate:	14.0549898147583%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.2
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	7.097
Half-life (T1/2):	0.088

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.393
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.725
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.499

Download Data

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

Natural Product: NPC314672

Natural Product ID:	NPC314672
*Common Name:**	Elloramycin
IUPAC Name:	methyl (6aR,7S,10aR)-6a,7,12-trihydroxy-8,10a-dimethoxy-1-methyl-6,10,11-trioxo-3-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy-7H-tetracene-2-carboxylate
Synonyms:	Elloramycin
Standard InCHIKey:	OYEXGNNKRQPUBW-FJYHMNRNSA-N
Standard InCHI:	InChI=1S/C32H36O15/c1-12-19-14(10-16(20(12)29(38)44-7)47-30-25(43-6)24(42-5)23(41-4)13(2)46-30)9-15-21(22(19)34)28(37)32(45-8)18(33)11-17(40-3)27(36)31(32,39)26(15)35/h9-11,13,23-25,27,30,34,36,39H,1-8H3/t13-,23-,24+,25+,27+,30-,31+,32+/m0/s1
SMILES:	CC1C(C(C(C(O1)OC2=CC3=CC4=C(C(=C3C(=C2C(=O)OC)C)O)C(=O)C5(C(=O)C=C(C(C5(C4=O)O)O)OC)OC)OC)OC)OC
Synthetic Gene Cluster:	BGC0000219;
ChEMBL Identifier:	CHEMBL1957887
PubChem CID:	10009567
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000022] Naphthacenes [CHEMONTID:0000155] Tetracenequinones

*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
NPO12176	Streptomyces olivaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11376004]
NPO12176	Streptomyces olivaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1367428]
NPO12176	Streptomyces olivaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[Article]
NPO12176	Streptomyces olivaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	25.0	mm	PMID[508258]

☑ 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 NPC314672 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	420
0.1-0.2	1655
0.2-0.3	3464
0.3-0.4	7500
0.4-0.5	9667
0.5-0.6	5875
0.6-0.7	5627
0.7-0.8	6541
0.8-0.85	1585
0.85-0.9	336
0.9-0.95	26
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC131405
0.9274	High Similarity	NPC48474
0.9205	High Similarity	NPC475161
0.9205	High Similarity	NPC208069
0.9205	High Similarity	NPC477860
0.9195	High Similarity	NPC68381
0.9162	High Similarity	NPC205721
0.9153	High Similarity	NPC313452
0.9143	High Similarity	NPC46958
0.9121	High Similarity	NPC470198
0.9121	High Similarity	NPC282474
0.9121	High Similarity	NPC470197
0.9121	High Similarity	NPC470200
0.9121	High Similarity	NPC470194
0.9121	High Similarity	NPC470195
0.9121	High Similarity	NPC316274
0.9121	High Similarity	NPC470196
0.9121	High Similarity	NPC470193
0.9096	High Similarity	NPC315221
0.9091	High Similarity	NPC477682
0.9091	High Similarity	NPC477683
0.9086	High Similarity	NPC186800
0.9086	High Similarity	NPC470667
0.908	High Similarity	NPC271385
0.908	High Similarity	NPC5029
0.908	High Similarity	NPC111536
0.908	High Similarity	NPC30432
0.908	High Similarity	NPC76128
0.908	High Similarity	NPC473113
0.905	High Similarity	NPC87583
0.904	High Similarity	NPC299149
0.904	High Similarity	NPC245059
0.904	High Similarity	NPC114257
0.904	High Similarity	NPC153578
0.904	High Similarity	NPC84494
0.904	High Similarity	NPC277710
0.9034	High Similarity	NPC475246
0.9034	High Similarity	NPC475233
0.9023	High Similarity	NPC298778
0.9011	High Similarity	NPC470199
0.9011	High Similarity	NPC314459
0.9	High Similarity	NPC105591
0.8989	High Similarity	NPC164047
0.8989	High Similarity	NPC470452
0.8989	High Similarity	NPC470453
0.8989	High Similarity	NPC470448
0.8977	High Similarity	NPC63105
0.8977	High Similarity	NPC3718
0.8977	High Similarity	NPC199533
0.8977	High Similarity	NPC470583
0.8977	High Similarity	NPC470454
0.8977	High Similarity	NPC19056
0.8971	High Similarity	NPC183441
0.8966	High Similarity	NPC473096
0.8966	High Similarity	NPC473095
0.8944	High Similarity	NPC241847
0.8939	High Similarity	NPC473631
0.8939	High Similarity	NPC293227
0.8939	High Similarity	NPC475662
0.8939	High Similarity	NPC473717
0.8933	High Similarity	NPC212290
0.8933	High Similarity	NPC58538
0.8927	High Similarity	NPC102053
0.8927	High Similarity	NPC289876
0.892	High Similarity	NPC472054
0.892	High Similarity	NPC213052
0.892	High Similarity	NPC98776
0.892	High Similarity	NPC203751
0.892	High Similarity	NPC199357
0.892	High Similarity	NPC85368
0.8914	High Similarity	NPC470580
0.8913	High Similarity	NPC314687
0.8908	High Similarity	NPC473094
0.8902	High Similarity	NPC178281
0.8876	High Similarity	NPC470581
0.8876	High Similarity	NPC47191
0.8876	High Similarity	NPC470582
0.8876	High Similarity	NPC115447
0.8876	High Similarity	NPC266513
0.887	High Similarity	NPC146803
0.887	High Similarity	NPC474345
0.8864	High Similarity	NPC294501
0.8864	High Similarity	NPC270027
0.8859	High Similarity	NPC314020
0.8857	High Similarity	NPC222455
0.8857	High Similarity	NPC259905
0.8852	High Similarity	NPC264302
0.8851	High Similarity	NPC178851
0.884	High Similarity	NPC229817
0.884	High Similarity	NPC221140
0.884	High Similarity	NPC475352
0.884	High Similarity	NPC475220
0.884	High Similarity	NPC473686
0.8827	High Similarity	NPC187441
0.8827	High Similarity	NPC283980
0.882	High Similarity	NPC469345
0.882	High Similarity	NPC176246
0.8814	High Similarity	NPC470335
0.8814	High Similarity	NPC470336
0.8814	High Similarity	NPC470438
0.8814	High Similarity	NPC154986
0.8807	High Similarity	NPC478021
0.88	High Similarity	NPC63470
0.8793	High Similarity	NPC329647
0.8793	High Similarity	NPC478022
0.8793	High Similarity	NPC470735
0.8793	High Similarity	NPC478020
0.8791	High Similarity	NPC174486
0.8786	High Similarity	NPC212099
0.8786	High Similarity	NPC101116
0.8786	High Similarity	NPC278329
0.8786	High Similarity	NPC146837
0.8785	High Similarity	NPC224557
0.8785	High Similarity	NPC106700
0.8785	High Similarity	NPC292706
0.8778	High Similarity	NPC197357
0.8778	High Similarity	NPC85316
0.8771	High Similarity	NPC470334
0.8771	High Similarity	NPC83331
0.8764	High Similarity	NPC98667
0.8764	High Similarity	NPC232412
0.8764	High Similarity	NPC86809
0.8763	High Similarity	NPC3474
0.8757	High Similarity	NPC315619
0.875	High Similarity	NPC246274
0.875	High Similarity	NPC191653
0.875	High Similarity	NPC473202
0.8736	High Similarity	NPC197972
0.8729	High Similarity	NPC475656
0.8729	High Similarity	NPC475148
0.8708	High Similarity	NPC65118
0.8708	High Similarity	NPC229051
0.8708	High Similarity	NPC131862
0.8701	High Similarity	NPC76047
0.8696	High Similarity	NPC201814
0.8693	High Similarity	NPC249977
0.8689	High Similarity	NPC282636
0.8689	High Similarity	NPC65489
0.8689	High Similarity	NPC294863
0.8686	High Similarity	NPC99216
0.8686	High Similarity	NPC7752
0.8686	High Similarity	NPC478026
0.8686	High Similarity	NPC280923
0.8681	High Similarity	NPC75574
0.8681	High Similarity	NPC231254
0.8681	High Similarity	NPC470416
0.8678	High Similarity	NPC216752
0.8667	High Similarity	NPC258044
0.8667	High Similarity	NPC196127
0.8667	High Similarity	NPC267680
0.8667	High Similarity	NPC35167
0.8667	High Similarity	NPC293626
0.8667	High Similarity	NPC477895
0.8667	High Similarity	NPC217387
0.8667	High Similarity	NPC267549
0.8659	High Similarity	NPC223735
0.8659	High Similarity	NPC307754
0.8659	High Similarity	NPC294149
0.8649	High Similarity	NPC321046
0.8649	High Similarity	NPC478034
0.8644	High Similarity	NPC5319
0.8636	High Similarity	NPC472150
0.8634	High Similarity	NPC111490
0.8634	High Similarity	NPC261623
0.8629	High Similarity	NPC17432
0.8629	High Similarity	NPC475183
0.8626	High Similarity	NPC162394
0.8626	High Similarity	NPC156785
0.8626	High Similarity	NPC241781
0.8626	High Similarity	NPC478001
0.8626	High Similarity	NPC36138
0.8619	High Similarity	NPC72783
0.8611	High Similarity	NPC198893
0.8611	High Similarity	NPC144097
0.8611	High Similarity	NPC232818
0.8611	High Similarity	NPC76112
0.8611	High Similarity	NPC472384
0.8611	High Similarity	NPC314489
0.8611	High Similarity	NPC67629
0.8611	High Similarity	NPC79736
0.8611	High Similarity	NPC472382
0.8611	High Similarity	NPC61904
0.8611	High Similarity	NPC66820
0.8611	High Similarity	NPC170018
0.8611	High Similarity	NPC92403
0.8611	High Similarity	NPC472380
0.8603	High Similarity	NPC476311
0.8603	High Similarity	NPC469393
0.8596	High Similarity	NPC280385
0.8596	High Similarity	NPC469344
0.8596	High Similarity	NPC313304
0.8596	High Similarity	NPC251144
0.8596	High Similarity	NPC52598
0.8596	High Similarity	NPC241387
0.8595	High Similarity	NPC93065
0.8595	High Similarity	NPC469652
0.8595	High Similarity	NPC472724
0.8595	High Similarity	NPC472721
0.8595	High Similarity	NPC31208
0.8595	High Similarity	NPC160543

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 NPC314672 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	970
0.2-0.3	1924
0.3-0.4	2562
0.4-0.5	1907
0.5-0.6	916
0.6-0.7	332
0.7-0.8	122
0.8-0.85	47
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9322	High Similarity	NPD7879	Clinical (unspecified phase)
0.8723	High Similarity	NPD7435	Discontinued
0.8644	High Similarity	NPD7804	Clinical (unspecified phase)
0.8611	High Similarity	NPD8313	Approved
0.8611	High Similarity	NPD8312	Approved
0.8549	High Similarity	NPD7874	Approved
0.8549	High Similarity	NPD7875	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD3751	Discontinued
0.8478	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6777	Approved
0.8466	Intermediate Similarity	NPD6780	Approved
0.8466	Intermediate Similarity	NPD6778	Approved
0.8466	Intermediate Similarity	NPD6782	Approved
0.8466	Intermediate Similarity	NPD6776	Approved
0.8466	Intermediate Similarity	NPD6779	Approved
0.8466	Intermediate Similarity	NPD6781	Approved
0.8453	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8453	Intermediate Similarity	NPD7808	Phase 3
0.8429	Intermediate Similarity	NPD7697	Approved
0.8429	Intermediate Similarity	NPD7696	Phase 3
0.8429	Intermediate Similarity	NPD7698	Approved
0.8402	Intermediate Similarity	NPD8151	Discontinued
0.8398	Intermediate Similarity	NPD7251	Discontinued
0.8385	Intermediate Similarity	NPD7871	Phase 2
0.8385	Intermediate Similarity	NPD7870	Phase 2
0.837	Intermediate Similarity	NPD8150	Discontinued
0.8351	Intermediate Similarity	NPD7701	Phase 2
0.8343	Intermediate Similarity	NPD6797	Phase 2
0.8343	Intermediate Similarity	NPD7075	Discontinued
0.8297	Intermediate Similarity	NPD6559	Discontinued
0.829	Intermediate Similarity	NPD8320	Phase 1
0.829	Intermediate Similarity	NPD8319	Approved
0.8287	Intermediate Similarity	NPD7074	Phase 3
0.8263	Intermediate Similarity	NPD7699	Phase 2
0.8263	Intermediate Similarity	NPD7700	Phase 2
0.8239	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD5844	Phase 1
0.8232	Intermediate Similarity	NPD7054	Approved
0.8223	Intermediate Similarity	NPD7801	Approved
0.8223	Intermediate Similarity	NPD7783	Phase 2
0.8223	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD7473	Discontinued
0.8202	Intermediate Similarity	NPD6959	Discontinued
0.8201	Intermediate Similarity	NPD6534	Approved
0.8201	Intermediate Similarity	NPD6535	Approved
0.8187	Intermediate Similarity	NPD7472	Approved
0.8171	Intermediate Similarity	NPD7819	Suspended
0.8171	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD3787	Discontinued
0.8156	Intermediate Similarity	NPD6232	Discontinued
0.8128	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD3818	Discontinued
0.8066	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD6166	Phase 2
0.8066	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD6823	Phase 2
0.7979	Intermediate Similarity	NPD8434	Phase 2
0.7978	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD5402	Approved
0.7898	Intermediate Similarity	NPD4380	Phase 2
0.788	Intermediate Similarity	NPD7228	Approved
0.7869	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD8455	Phase 2
0.7865	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD3226	Approved
0.7821	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3817	Phase 2
0.7797	Intermediate Similarity	NPD6599	Discontinued
0.7753	Intermediate Similarity	NPD7411	Suspended
0.7709	Intermediate Similarity	NPD1934	Approved
0.768	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7768	Phase 2
0.768	Intermediate Similarity	NPD6212	Phase 3
0.768	Intermediate Similarity	NPD6213	Phase 3
0.768	Intermediate Similarity	NPD3882	Suspended
0.7667	Intermediate Similarity	NPD1465	Phase 2
0.7657	Intermediate Similarity	NPD6799	Approved
0.765	Intermediate Similarity	NPD5494	Approved
0.764	Intermediate Similarity	NPD7458	Discontinued
0.7637	Intermediate Similarity	NPD3749	Approved
0.7627	Intermediate Similarity	NPD5403	Approved
0.7619	Intermediate Similarity	NPD7685	Pre-registration
0.7614	Intermediate Similarity	NPD2534	Approved
0.7614	Intermediate Similarity	NPD2532	Approved
0.7614	Intermediate Similarity	NPD2533	Approved
0.7614	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD37	Approved
0.7596	Intermediate Similarity	NPD6234	Discontinued
0.7582	Intermediate Similarity	NPD4965	Approved
0.7582	Intermediate Similarity	NPD4967	Phase 2
0.7582	Intermediate Similarity	NPD4966	Approved
0.7569	Intermediate Similarity	NPD2801	Approved
0.7542	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7240	Approved
0.7514	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2346	Discontinued
0.7512	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD8059	Phase 3
0.7486	Intermediate Similarity	NPD4628	Phase 3
0.7475	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6190	Approved
0.7419	Intermediate Similarity	NPD7199	Phase 2
0.74	Intermediate Similarity	NPD8285	Discontinued
0.7386	Intermediate Similarity	NPD3750	Approved
0.7374	Intermediate Similarity	NPD1512	Approved
0.7371	Intermediate Similarity	NPD1549	Phase 2
0.736	Intermediate Similarity	NPD7390	Discontinued
0.7356	Intermediate Similarity	NPD2935	Discontinued
0.733	Intermediate Similarity	NPD6674	Discontinued
0.733	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7930	Approved
0.7318	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7584	Approved
0.7316	Intermediate Similarity	NPD7799	Discontinued
0.7314	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD919	Approved
0.7299	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1511	Approved
0.7249	Intermediate Similarity	NPD3926	Phase 2
0.7238	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1247	Approved
0.7219	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD1653	Approved
0.7196	Intermediate Similarity	NPD5710	Approved
0.7196	Intermediate Similarity	NPD5711	Approved
0.7196	Intermediate Similarity	NPD8366	Approved
0.7191	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD8404	Phase 2
0.7165	Intermediate Similarity	NPD8368	Discontinued
0.7159	Intermediate Similarity	NPD5404	Approved
0.7159	Intermediate Similarity	NPD2796	Approved
0.7159	Intermediate Similarity	NPD5405	Approved
0.7159	Intermediate Similarity	NPD5408	Approved
0.7159	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2800	Approved
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7266	Discontinued
0.7116	Intermediate Similarity	NPD7907	Approved
0.7115	Intermediate Similarity	NPD7585	Approved
0.7113	Intermediate Similarity	NPD5953	Discontinued
0.7102	Intermediate Similarity	NPD3748	Approved
0.7102	Intermediate Similarity	NPD2799	Discontinued
0.7102	Intermediate Similarity	NPD1510	Phase 2
0.7101	Intermediate Similarity	NPD7999	Approved
0.7095	Intermediate Similarity	NPD7003	Approved
0.7091	Intermediate Similarity	NPD8067	Phase 3
0.7087	Intermediate Similarity	NPD7680	Approved
0.7086	Intermediate Similarity	NPD1607	Approved
0.7085	Intermediate Similarity	NPD8360	Approved
0.7085	Intermediate Similarity	NPD8361	Approved
0.7085	Intermediate Similarity	NPD8435	Approved
0.7072	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4060	Phase 1
0.7067	Intermediate Similarity	NPD7583	Approved
0.7064	Intermediate Similarity	NPD8491	Approved
0.7062	Intermediate Similarity	NPD6100	Approved
0.7062	Intermediate Similarity	NPD1551	Phase 2
0.7062	Intermediate Similarity	NPD6099	Approved
0.7056	Intermediate Similarity	NPD8407	Phase 2
0.7053	Intermediate Similarity	NPD8127	Discontinued
0.7049	Intermediate Similarity	NPD920	Approved
0.7047	Intermediate Similarity	NPD7177	Discontinued
0.7045	Intermediate Similarity	NPD7097	Phase 1
0.7024	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2344	Approved
0.7016	Intermediate Similarity	NPD7229	Phase 3
0.701	Intermediate Similarity	NPD7286	Phase 2
0.701	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6273	Approved
0.6971	Remote Similarity	NPD1240	Approved
0.6954	Remote Similarity	NPD6798	Discontinued
0.6954	Remote Similarity	NPD2313	Discontinued
0.6944	Remote Similarity	NPD1243	Approved
0.694	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1933	Approved
0.6932	Remote Similarity	NPD6355	Discontinued
0.6927	Remote Similarity	NPD1471	Phase 3
0.6914	Remote Similarity	NPD6233	Phase 2
0.6906	Remote Similarity	NPD8166	Discontinued
0.6893	Remote Similarity	NPD6651	Approved
0.6878	Remote Similarity	NPD8485	Approved
0.6868	Remote Similarity	NPD2309	Approved
0.6866	Remote Similarity	NPD4665	Approved
0.6866	Remote Similarity	NPD4111	Phase 1
0.6857	Remote Similarity	NPD7985	Registered
0.6857	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7784	Clinical (unspecified phase)

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