NPASS Compound

Structure

NPC30027 OpenBabel07101719132D 35 39 0 0 0 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8993 5.2857 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 0.4654 3.1857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2867 4.2889 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 -1.7321 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 0 0 0 0 0 0 0 0 0 0 0.4078 3.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1715 2.7515 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9236 3.8546 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 3.0860 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -1.5605 2.7515 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2340 4.5177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 -2.3424 3.3750 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 -1.8246 4.2885 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 34 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 25 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 14 29 1 0 0 0 0 15 17 2 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 16 34 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 19 22 2 0 0 0 0 20 21 1 0 0 0 0 20 24 1 0 0 0 0 21 25 2 0 0 0 0 22 23 1 0 0 0 0 22 26 1 0 0 0 0 23 31 2 0 0 0 0 24 32 2 0 0 0 0 25 35 1 0 0 0 0 26 33 2 0 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.1
Volume:	460.308
LogP:	4.998
LogD:	2.581
LogS:	-6.206
# Rotatable Bonds:	3
TPSA:	157.66
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	3.435
Fsp3:	0.077
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.99
MDCK Permeability:	4.619095761881908e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.637
20% Bioavailability (F20%):	0.189
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	90.05526733398438%
Volume Distribution (VD):	0.621
Pgp-substrate:	14.144720077514648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.884
CYP1A2-substrate:	0.401
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.665
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	5.514
Half-life (T1/2):	0.602

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.564
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.313
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.835
Carcinogencity:	0.047
Eye Corrosion:	0.004
Eye Irritation:	0.923
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC30027

Natural Product ID:	NPC30027
*Common Name:**	Aspergiolide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JZRWJIYIEFXUOK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H18O9/c1-9-4-11(27)7-15(30)17(9)23(31)22-19-13-6-12(28)8-16(34-3)18(13)24(32)20-14(29)5-10(2)25(21(19)20)35-26(22)33/h4-8,27-30H,1-3H3
SMILES:	COc1cc(O)cc2c1C(=O)c1c(O)cc(c3c1c2c(c(=O)o3)C(=O)c1c(C)cc(cc1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL575190
PubChem CID:	25157273
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO11579	Aspergillus glaucus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18986198]
NPO11579	Aspergillus glaucus	Species	Aspergillaceae	Eukaryota	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	510.0	nM	PMID[530074]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	240.0	nM	PMID[530074]

☑ 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 NPC30027 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	425
0.1-0.2	2035
0.2-0.3	4490
0.3-0.4	10218
0.4-0.5	8099
0.5-0.6	4210
0.6-0.7	5343
0.7-0.8	5042
0.8-0.85	2290
0.85-0.9	507
0.9-0.95	34
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC146211
0.9441	High Similarity	NPC76647
0.9308	High Similarity	NPC186325
0.925	High Similarity	NPC189552
0.925	High Similarity	NPC273467
0.9245	High Similarity	NPC177650
0.9187	High Similarity	NPC143050
0.9187	High Similarity	NPC312993
0.9172	High Similarity	NPC175978
0.9152	High Similarity	NPC477836
0.9146	High Similarity	NPC49487
0.9146	High Similarity	NPC99613
0.9108	High Similarity	NPC133856
0.9103	High Similarity	NPC291049
0.9103	High Similarity	NPC233267
0.908	High Similarity	NPC469664
0.9062	High Similarity	NPC263483
0.9051	High Similarity	NPC273483
0.9048	High Similarity	NPC207467
0.9038	High Similarity	NPC105415
0.9036	High Similarity	NPC158226
0.9024	High Similarity	NPC29160
0.9024	High Similarity	NPC477835
0.9018	High Similarity	NPC474350
0.9006	High Similarity	NPC55443
0.9006	High Similarity	NPC18699
0.8994	High Similarity	NPC280530
0.8994	High Similarity	NPC329844
0.8994	High Similarity	NPC95842
0.8994	High Similarity	NPC178964
0.8981	High Similarity	NPC100985
0.8981	High Similarity	NPC97029
0.8981	High Similarity	NPC65589
0.8981	High Similarity	NPC158338
0.8981	High Similarity	NPC97028
0.8981	High Similarity	NPC288036
0.8976	High Similarity	NPC109827
0.8976	High Similarity	NPC124470
0.8974	High Similarity	NPC12305
0.897	High Similarity	NPC234331
0.8957	High Similarity	NPC15374
0.8951	High Similarity	NPC470342
0.8951	High Similarity	NPC472060
0.8951	High Similarity	NPC472052
0.8941	High Similarity	NPC265795
0.8938	High Similarity	NPC254351
0.8938	High Similarity	NPC55662
0.8938	High Similarity	NPC89625
0.8938	High Similarity	NPC66508
0.8938	High Similarity	NPC226656
0.8938	High Similarity	NPC149618
0.8938	High Similarity	NPC66029
0.8938	High Similarity	NPC166054
0.8931	High Similarity	NPC217447
0.8931	High Similarity	NPC154683
0.8931	High Similarity	NPC40356
0.8924	High Similarity	NPC294646
0.8924	High Similarity	NPC307780
0.8924	High Similarity	NPC474660
0.8924	High Similarity	NPC309979
0.8924	High Similarity	NPC473466
0.8924	High Similarity	NPC227122
0.8917	High Similarity	NPC7025
0.8917	High Similarity	NPC256672
0.8917	High Similarity	NPC27221
0.8916	High Similarity	NPC165979
0.8916	High Similarity	NPC163130
0.8896	High Similarity	NPC18380
0.8896	High Similarity	NPC66288
0.8889	High Similarity	NPC324736
0.8882	High Similarity	NPC473785
0.8876	High Similarity	NPC216307
0.8875	High Similarity	NPC214632
0.8875	High Similarity	NPC194593
0.8875	High Similarity	NPC135522
0.8875	High Similarity	NPC290830
0.8875	High Similarity	NPC303485
0.8875	High Similarity	NPC71061
0.8875	High Similarity	NPC72425
0.8875	High Similarity	NPC477691
0.8868	High Similarity	NPC149526
0.8868	High Similarity	NPC478148
0.8868	High Similarity	NPC474417
0.8854	High Similarity	NPC123202
0.8854	High Similarity	NPC7943
0.8854	High Similarity	NPC22005
0.8846	High Similarity	NPC134621
0.8841	High Similarity	NPC108767
0.8834	High Similarity	NPC184326
0.8834	High Similarity	NPC292863
0.8834	High Similarity	NPC476506
0.8827	High Similarity	NPC44199
0.882	High Similarity	NPC52611
0.882	High Similarity	NPC159707
0.882	High Similarity	NPC158027
0.882	High Similarity	NPC100049
0.882	High Similarity	NPC14606
0.882	High Similarity	NPC215203
0.882	High Similarity	NPC248739
0.882	High Similarity	NPC186227
0.882	High Similarity	NPC205026
0.882	High Similarity	NPC121649
0.882	High Similarity	NPC265624
0.882	High Similarity	NPC150908
0.8817	High Similarity	NPC199533
0.8817	High Similarity	NPC470454
0.8812	High Similarity	NPC477690
0.8805	High Similarity	NPC60413
0.8805	High Similarity	NPC202595
0.8805	High Similarity	NPC295036
0.8805	High Similarity	NPC158866
0.8797	High Similarity	NPC2569
0.8797	High Similarity	NPC37139
0.8797	High Similarity	NPC172329
0.8795	High Similarity	NPC251336
0.8795	High Similarity	NPC20216
0.879	High Similarity	NPC225173
0.879	High Similarity	NPC237208
0.879	High Similarity	NPC473927
0.879	High Similarity	NPC163846
0.8788	High Similarity	NPC156082
0.8788	High Similarity	NPC270837
0.8788	High Similarity	NPC207690
0.8782	High Similarity	NPC66404
0.8782	High Similarity	NPC95123
0.878	High Similarity	NPC472261
0.878	High Similarity	NPC137232
0.8773	High Similarity	NPC195167
0.8773	High Similarity	NPC186113
0.8773	High Similarity	NPC51760
0.8772	High Similarity	NPC84494
0.8772	High Similarity	NPC245059
0.8765	High Similarity	NPC180924
0.8765	High Similarity	NPC32867
0.8758	High Similarity	NPC210942
0.8758	High Similarity	NPC169990
0.875	High Similarity	NPC313304
0.875	High Similarity	NPC20543
0.875	High Similarity	NPC246716
0.875	High Similarity	NPC298778
0.875	High Similarity	NPC67322
0.875	High Similarity	NPC17219
0.875	High Similarity	NPC222713
0.875	High Similarity	NPC111112
0.875	High Similarity	NPC72958
0.875	High Similarity	NPC232645
0.875	High Similarity	NPC138299
0.875	High Similarity	NPC239440
0.8743	High Similarity	NPC295436
0.8742	High Similarity	NPC288840
0.8742	High Similarity	NPC10027
0.8742	High Similarity	NPC291746
0.8742	High Similarity	NPC266499
0.8742	High Similarity	NPC6923
0.8742	High Similarity	NPC65775
0.8735	High Similarity	NPC259757
0.8735	High Similarity	NPC112981
0.8734	High Similarity	NPC245584
0.8734	High Similarity	NPC289042
0.8734	High Similarity	NPC118027
0.8734	High Similarity	NPC190648
0.8734	High Similarity	NPC56433
0.8734	High Similarity	NPC34802
0.8734	High Similarity	NPC126767
0.8734	High Similarity	NPC125801
0.8734	High Similarity	NPC312929
0.8727	High Similarity	NPC229632
0.8727	High Similarity	NPC294965
0.8726	High Similarity	NPC29577
0.8721	High Similarity	NPC470453
0.8721	High Similarity	NPC164047
0.8721	High Similarity	NPC470452
0.8721	High Similarity	NPC470448
0.872	High Similarity	NPC243701
0.872	High Similarity	NPC119224
0.872	High Similarity	NPC470810
0.8712	High Similarity	NPC96342
0.8712	High Similarity	NPC217677
0.8712	High Similarity	NPC212967
0.8712	High Similarity	NPC164110
0.8712	High Similarity	NPC246647
0.8712	High Similarity	NPC165977
0.8706	High Similarity	NPC289147
0.8706	High Similarity	NPC68381
0.8706	High Similarity	NPC139350
0.8704	High Similarity	NPC66441
0.8704	High Similarity	NPC182555
0.8696	High Similarity	NPC87708
0.8696	High Similarity	NPC271681
0.8696	High Similarity	NPC174086
0.8696	High Similarity	NPC474843
0.8696	High Similarity	NPC281272
0.869	High Similarity	NPC26568
0.8688	High Similarity	NPC150928
0.8688	High Similarity	NPC37348
0.8688	High Similarity	NPC101957
0.8688	High Similarity	NPC325983
0.8688	High Similarity	NPC470107
0.8688	High Similarity	NPC205766
0.8688	High Similarity	NPC120105

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 NPC30027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	1051
0.2-0.3	1836
0.3-0.4	2683
0.4-0.5	1868
0.5-0.6	869
0.6-0.7	261
0.7-0.8	140
0.8-0.85	36
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9012	High Similarity	NPD6959	Discontinued
0.8727	High Similarity	NPD6232	Discontinued
0.8683	High Similarity	NPD7473	Discontinued
0.8642	High Similarity	NPD7819	Suspended
0.858	High Similarity	NPD5844	Phase 1
0.8519	High Similarity	NPD7411	Suspended
0.8512	High Similarity	NPD7852	Clinical (unspecified phase)
0.8509	High Similarity	NPD3226	Approved
0.8491	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD2532	Approved
0.8491	Intermediate Similarity	NPD2533	Approved
0.8491	Intermediate Similarity	NPD2534	Approved
0.8428	Intermediate Similarity	NPD7390	Discontinued
0.8373	Intermediate Similarity	NPD3749	Approved
0.8364	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7768	Phase 2
0.8303	Intermediate Similarity	NPD2801	Approved
0.8239	Intermediate Similarity	NPD3750	Approved
0.8212	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7075	Discontinued
0.8121	Intermediate Similarity	NPD4380	Phase 2
0.8101	Intermediate Similarity	NPD2935	Discontinued
0.8081	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD6166	Phase 2
0.8081	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD2346	Discontinued
0.8038	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD5402	Approved
0.8036	Intermediate Similarity	NPD3817	Phase 2
0.8024	Intermediate Similarity	NPD6801	Discontinued
0.8023	Intermediate Similarity	NPD8313	Approved
0.8023	Intermediate Similarity	NPD8312	Approved
0.7976	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD1465	Phase 2
0.7975	Intermediate Similarity	NPD1511	Approved
0.7966	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD5494	Approved
0.795	Intermediate Similarity	NPD2800	Approved
0.795	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD3748	Approved
0.7925	Intermediate Similarity	NPD1510	Phase 2
0.7917	Intermediate Similarity	NPD1934	Approved
0.7911	Intermediate Similarity	NPD1607	Approved
0.791	Intermediate Similarity	NPD6559	Discontinued
0.7904	Intermediate Similarity	NPD6599	Discontinued
0.7888	Intermediate Similarity	NPD1549	Phase 2
0.7879	Intermediate Similarity	NPD1512	Approved
0.7875	Intermediate Similarity	NPD2796	Approved
0.7875	Intermediate Similarity	NPD5406	Approved
0.7875	Intermediate Similarity	NPD5404	Approved
0.7875	Intermediate Similarity	NPD5408	Approved
0.7875	Intermediate Similarity	NPD5405	Approved
0.7861	Intermediate Similarity	NPD5710	Approved
0.7861	Intermediate Similarity	NPD5711	Approved
0.7841	Intermediate Similarity	NPD7054	Approved
0.784	Intermediate Similarity	NPD1243	Approved
0.7831	Intermediate Similarity	NPD920	Approved
0.7797	Intermediate Similarity	NPD7074	Phase 3
0.7797	Intermediate Similarity	NPD7472	Approved
0.7791	Intermediate Similarity	NPD7003	Approved
0.7785	Intermediate Similarity	NPD1240	Approved
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD7435	Discontinued
0.7772	Intermediate Similarity	NPD7783	Phase 2
0.7772	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1551	Phase 2
0.776	Intermediate Similarity	NPD8151	Discontinued
0.7758	Intermediate Similarity	NPD6799	Approved
0.7753	Intermediate Similarity	NPD6797	Phase 2
0.7738	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD6779	Approved
0.7713	Intermediate Similarity	NPD6776	Approved
0.7713	Intermediate Similarity	NPD6780	Approved
0.7713	Intermediate Similarity	NPD6781	Approved
0.7713	Intermediate Similarity	NPD6782	Approved
0.7713	Intermediate Similarity	NPD6777	Approved
0.7713	Intermediate Similarity	NPD6778	Approved
0.7711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7251	Discontinued
0.7702	Intermediate Similarity	NPD2799	Discontinued
0.7683	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3882	Suspended
0.7667	Intermediate Similarity	NPD7808	Phase 3
0.7658	Intermediate Similarity	NPD2313	Discontinued
0.7657	Intermediate Similarity	NPD7229	Phase 3
0.7654	Intermediate Similarity	NPD6100	Approved
0.7654	Intermediate Similarity	NPD5953	Discontinued
0.7654	Intermediate Similarity	NPD6099	Approved
0.7644	Intermediate Similarity	NPD7870	Phase 2
0.7644	Intermediate Similarity	NPD7871	Phase 2
0.7619	Intermediate Similarity	NPD5403	Approved
0.7605	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8150	Discontinued
0.7592	Intermediate Similarity	NPD7698	Approved
0.7592	Intermediate Similarity	NPD7696	Phase 3
0.7592	Intermediate Similarity	NPD7697	Approved
0.759	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7177	Discontinued
0.7578	Intermediate Similarity	NPD6651	Approved
0.7547	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7286	Phase 2
0.7538	Intermediate Similarity	NPD7874	Approved
0.7538	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD5401	Approved
0.7486	Intermediate Similarity	NPD919	Approved
0.7486	Intermediate Similarity	NPD6234	Discontinued
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.747	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4628	Phase 3
0.7458	Intermediate Similarity	NPD3787	Discontinued
0.7456	Intermediate Similarity	NPD6273	Approved
0.7448	Intermediate Similarity	NPD6823	Phase 2
0.7447	Intermediate Similarity	NPD6534	Approved
0.7447	Intermediate Similarity	NPD6535	Approved
0.7438	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3268	Approved
0.7438	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7701	Phase 2
0.7419	Intermediate Similarity	NPD4287	Approved
0.7416	Intermediate Similarity	NPD3926	Phase 2
0.7412	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD1247	Approved
0.7401	Intermediate Similarity	NPD7199	Phase 2
0.7389	Intermediate Similarity	NPD3751	Discontinued
0.7389	Intermediate Similarity	NPD7228	Approved
0.7378	Intermediate Similarity	NPD4308	Phase 3
0.7377	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4625	Phase 3
0.7368	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2797	Approved
0.7342	Intermediate Similarity	NPD1203	Approved
0.733	Intermediate Similarity	NPD7699	Phase 2
0.733	Intermediate Similarity	NPD7700	Phase 2
0.7329	Intermediate Similarity	NPD3764	Approved
0.7323	Intermediate Similarity	NPD7801	Approved
0.7321	Intermediate Similarity	NPD2309	Approved
0.7318	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4288	Approved
0.7312	Intermediate Similarity	NPD6832	Phase 2
0.7312	Intermediate Similarity	NPD4908	Phase 1
0.7292	Intermediate Similarity	NPD8285	Discontinued
0.7258	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8455	Phase 2
0.7255	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1470	Approved
0.7222	Intermediate Similarity	NPD411	Approved
0.7219	Intermediate Similarity	NPD8434	Phase 2
0.7211	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6212	Phase 3
0.7211	Intermediate Similarity	NPD6213	Phase 3
0.7198	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD422	Phase 1
0.7197	Intermediate Similarity	NPD1201	Approved
0.7195	Intermediate Similarity	NPD447	Suspended
0.7195	Intermediate Similarity	NPD5124	Phase 1
0.7195	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD230	Phase 1
0.7194	Intermediate Similarity	NPD8319	Approved
0.7194	Intermediate Similarity	NPD8320	Phase 1
0.7173	Intermediate Similarity	NPD4363	Phase 3
0.7173	Intermediate Similarity	NPD4360	Phase 2
0.717	Intermediate Similarity	NPD3225	Approved
0.717	Intermediate Similarity	NPD1283	Approved
0.7169	Intermediate Similarity	NPD7033	Discontinued
0.7165	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD943	Approved
0.7134	Intermediate Similarity	NPD4307	Phase 2
0.7125	Intermediate Similarity	NPD3266	Approved
0.7125	Intermediate Similarity	NPD3267	Approved
0.7089	Intermediate Similarity	NPD1611	Approved
0.7083	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1471	Phase 3
0.7081	Intermediate Similarity	NPD2798	Approved
0.7071	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4626	Approved
0.7048	Intermediate Similarity	NPD7654	Discontinued
0.7043	Intermediate Similarity	NPD7240	Approved
0.703	Intermediate Similarity	NPD4060	Phase 1
0.703	Intermediate Similarity	NPD2979	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data