NPASS Compound

Structure

NPC74413 OpenBabel07101719142D 30 34 0 0 0 0 0 0 0 0999 V2000 1.9052 3.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 2.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0540 -0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2653 1.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6180 1.9021 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 3.6666 2.1759 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 -0.2738 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0292 2.4373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9271 2.8532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 30 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 17 2 0 0 0 0 10 18 2 0 0 0 0 11 15 2 0 0 0 0 11 25 1 0 0 0 0 12 16 2 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 21 1 0 0 0 0 20 24 2 0 0 0 0 21 23 1 0 0 0 0 21 27 2 0 0 0 0 22 24 1 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.13
Volume:	406.395
LogP:	4.557
LogD:	3.384
LogS:	-4.719
# Rotatable Bonds:	2
TPSA:	83.64
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	3.186
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.094
MDCK Permeability:	1.0562819625192787e-05
Pgp-inhibitor:	0.531
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	93.75591278076172%
Volume Distribution (VD):	0.434
Pgp-substrate:	8.153116226196289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.406
CYP2C19-substrate:	0.314
CYP2C9-inhibitor:	0.577
CYP2C9-substrate:	0.839
CYP2D6-inhibitor:	0.43
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	0.725
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.369
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.748
Rat Oral Acute Toxicity:	0.81
Maximum Recommended Daily Dose:	0.689
Skin Sensitization:	0.907
Carcinogencity:	0.955
Eye Corrosion:	0.003
Eye Irritation:	0.398
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC74413

Natural Product ID:	NPC74413
*Common Name:**	Asterriquinone D
IUPAC Name:	2,5-bis(1H-indol-3-yl)-3,6-dimethoxycyclohexa-2,5-diene-1,4-dione
Synonyms:	Asterriquinone D
Standard InCHIKey:	IVPGMNQTDHNSBX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H18N2O4/c1-29-23-19(15-11-25-17-9-5-3-7-13(15)17)22(28)24(30-2)20(21(23)27)16-12-26-18-10-6-4-8-14(16)18/h3-12,25-26H,1-2H3
SMILES:	COC1=C(c2c[nH]c3ccccc23)C(=O)C(=C(c2c[nH]c3ccccc23)C1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512621
PubChem CID:	23247888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	from the rhizosphere of Opuntia versicolor of the Sonoran Desert	n.a.	PMID[14695798]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124769]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271552]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22360613]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24534845]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25671343]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2921224]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30207465]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32163285]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32897070]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984154]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2595	Aspergillus terreus	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	19900.0	nM	PMID[468452]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	17700.0	nM	PMID[468452]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	15800.0	nM	PMID[468452]

☑ 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 NPC74413 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	359
0.1-0.2	2458
0.2-0.3	12618
0.3-0.4	18727
0.4-0.5	4185
0.5-0.6	1714
0.6-0.7	1916
0.7-0.8	686
0.8-0.85	26
0.85-0.9	3
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9832	High Similarity	NPC260900
0.9553	High Similarity	NPC227582
0.9396	High Similarity	NPC252338
0.9062	High Similarity	NPC474412
0.8571	High Similarity	NPC67288
0.8474	Intermediate Similarity	NPC131887
0.8473	Intermediate Similarity	NPC476818
0.8441	Intermediate Similarity	NPC321708
0.8407	Intermediate Similarity	NPC55772
0.8351	Intermediate Similarity	NPC476460
0.8263	Intermediate Similarity	NPC304203
0.8259	Intermediate Similarity	NPC36405
0.8205	Intermediate Similarity	NPC476073
0.8182	Intermediate Similarity	NPC308931
0.8182	Intermediate Similarity	NPC99939
0.8152	Intermediate Similarity	NPC284775
0.8152	Intermediate Similarity	NPC59269
0.8138	Intermediate Similarity	NPC235684
0.8112	Intermediate Similarity	NPC193761
0.8105	Intermediate Similarity	NPC154339
0.8098	Intermediate Similarity	NPC276657
0.8081	Intermediate Similarity	NPC472064
0.8073	Intermediate Similarity	NPC267343
0.806	Intermediate Similarity	NPC82370
0.8054	Intermediate Similarity	NPC145885
0.8054	Intermediate Similarity	NPC111275
0.8054	Intermediate Similarity	NPC84827
0.8054	Intermediate Similarity	NPC14113
0.803	Intermediate Similarity	NPC478157
0.8022	Intermediate Similarity	NPC78020
0.8021	Intermediate Similarity	NPC47190
0.8	Intermediate Similarity	NPC264285
0.8	Intermediate Similarity	NPC267885
0.8	Intermediate Similarity	NPC258062
0.799	Intermediate Similarity	NPC11445
0.798	Intermediate Similarity	NPC317701
0.7979	Intermediate Similarity	NPC326422
0.796	Intermediate Similarity	NPC478158
0.795	Intermediate Similarity	NPC225821
0.7947	Intermediate Similarity	NPC315555
0.7946	Intermediate Similarity	NPC149155
0.7946	Intermediate Similarity	NPC110500
0.7946	Intermediate Similarity	NPC203468
0.7938	Intermediate Similarity	NPC195239
0.7938	Intermediate Similarity	NPC157828
0.7933	Intermediate Similarity	NPC16352
0.7929	Intermediate Similarity	NPC472062
0.7929	Intermediate Similarity	NPC472069
0.7929	Intermediate Similarity	NPC472063
0.7923	Intermediate Similarity	NPC63751
0.7917	Intermediate Similarity	NPC472112
0.7914	Intermediate Similarity	NPC283219
0.7914	Intermediate Similarity	NPC248041
0.7914	Intermediate Similarity	NPC126709
0.7914	Intermediate Similarity	NPC213468
0.79	Intermediate Similarity	NPC472065
0.7895	Intermediate Similarity	NPC229893
0.7868	Intermediate Similarity	NPC284338
0.7857	Intermediate Similarity	NPC311276
0.7853	Intermediate Similarity	NPC53947
0.7853	Intermediate Similarity	NPC62749
0.7843	Intermediate Similarity	NPC87856
0.7842	Intermediate Similarity	NPC477003
0.7839	Intermediate Similarity	NPC476874
0.7835	Intermediate Similarity	NPC472113
0.7822	Intermediate Similarity	NPC127677
0.7816	Intermediate Similarity	NPC203614
0.7816	Intermediate Similarity	NPC132211
0.7812	Intermediate Similarity	NPC17059
0.7801	Intermediate Similarity	NPC15102
0.78	Intermediate Similarity	NPC98715
0.7795	Intermediate Similarity	NPC88315
0.779	Intermediate Similarity	NPC92796
0.779	Intermediate Similarity	NPC135141
0.7788	Intermediate Similarity	NPC101350
0.7784	Intermediate Similarity	NPC288838
0.7783	Intermediate Similarity	NPC472070
0.7783	Intermediate Similarity	NPC162860
0.7783	Intermediate Similarity	NPC271862
0.7778	Intermediate Similarity	NPC472285
0.7772	Intermediate Similarity	NPC49954
0.7772	Intermediate Similarity	NPC474561
0.7772	Intermediate Similarity	NPC160105
0.7772	Intermediate Similarity	NPC54420
0.7772	Intermediate Similarity	NPC213629
0.7772	Intermediate Similarity	NPC46225
0.7767	Intermediate Similarity	NPC70155
0.7766	Intermediate Similarity	NPC106824
0.7757	Intermediate Similarity	NPC267853
0.7756	Intermediate Similarity	NPC207020
0.7742	Intermediate Similarity	NPC15801
0.7742	Intermediate Similarity	NPC235685
0.7721	Intermediate Similarity	NPC244897
0.7718	Intermediate Similarity	NPC234078
0.7718	Intermediate Similarity	NPC221100
0.7714	Intermediate Similarity	NPC2395
0.7705	Intermediate Similarity	NPC282231
0.7704	Intermediate Similarity	NPC247735
0.7704	Intermediate Similarity	NPC472210
0.7704	Intermediate Similarity	NPC269886
0.7704	Intermediate Similarity	NPC472295
0.7704	Intermediate Similarity	NPC81802
0.77	Intermediate Similarity	NPC300183
0.7696	Intermediate Similarity	NPC469358
0.7692	Intermediate Similarity	NPC138370
0.7689	Intermediate Similarity	NPC235885
0.7688	Intermediate Similarity	NPC81535
0.7684	Intermediate Similarity	NPC469896
0.768	Intermediate Similarity	NPC63199
0.768	Intermediate Similarity	NPC196251
0.768	Intermediate Similarity	NPC111602
0.768	Intermediate Similarity	NPC102338
0.7677	Intermediate Similarity	NPC167710
0.7672	Intermediate Similarity	NPC151939
0.767	Intermediate Similarity	NPC151976
0.767	Intermediate Similarity	NPC75634
0.7668	Intermediate Similarity	NPC118084
0.7667	Intermediate Similarity	NPC73952
0.7667	Intermediate Similarity	NPC25008
0.7667	Intermediate Similarity	NPC259644
0.7667	Intermediate Similarity	NPC469765
0.7667	Intermediate Similarity	NPC469760
0.7667	Intermediate Similarity	NPC469786
0.7667	Intermediate Similarity	NPC469763
0.7653	Intermediate Similarity	NPC472292
0.765	Intermediate Similarity	NPC316411
0.765	Intermediate Similarity	NPC279918
0.7644	Intermediate Similarity	NPC71037
0.7644	Intermediate Similarity	NPC204491
0.7644	Intermediate Similarity	NPC191415
0.7642	Intermediate Similarity	NPC147446
0.7641	Intermediate Similarity	NPC329858
0.7638	Intermediate Similarity	NPC149708
0.7638	Intermediate Similarity	NPC171317
0.7637	Intermediate Similarity	NPC216643
0.7637	Intermediate Similarity	NPC469762
0.7633	Intermediate Similarity	NPC267965
0.7626	Intermediate Similarity	NPC472293
0.7624	Intermediate Similarity	NPC70922
0.7624	Intermediate Similarity	NPC212376
0.7624	Intermediate Similarity	NPC80597
0.7624	Intermediate Similarity	NPC75540
0.7624	Intermediate Similarity	NPC211572
0.7622	Intermediate Similarity	NPC42372
0.7617	Intermediate Similarity	NPC192712
0.7617	Intermediate Similarity	NPC280290
0.7606	Intermediate Similarity	NPC314603
0.76	Intermediate Similarity	NPC220797
0.76	Intermediate Similarity	NPC474318
0.76	Intermediate Similarity	NPC268744
0.76	Intermediate Similarity	NPC153123
0.76	Intermediate Similarity	NPC475914
0.76	Intermediate Similarity	NPC201266
0.7593	Intermediate Similarity	NPC315062
0.7586	Intermediate Similarity	NPC473376
0.7585	Intermediate Similarity	NPC110182
0.7585	Intermediate Similarity	NPC118940
0.7582	Intermediate Similarity	NPC469785
0.7581	Intermediate Similarity	NPC54988
0.7578	Intermediate Similarity	NPC178858
0.7577	Intermediate Similarity	NPC94752
0.757	Intermediate Similarity	NPC267926
0.7568	Intermediate Similarity	NPC21174
0.7568	Intermediate Similarity	NPC194640
0.7568	Intermediate Similarity	NPC271797
0.7566	Intermediate Similarity	NPC293216
0.7565	Intermediate Similarity	NPC228835
0.7565	Intermediate Similarity	NPC258480
0.7562	Intermediate Similarity	NPC269203
0.7562	Intermediate Similarity	NPC166209
0.7562	Intermediate Similarity	NPC77241
0.7562	Intermediate Similarity	NPC213308
0.7562	Intermediate Similarity	NPC13456
0.7558	Intermediate Similarity	NPC207686
0.7551	Intermediate Similarity	NPC324091
0.7551	Intermediate Similarity	NPC83111
0.7551	Intermediate Similarity	NPC314333
0.755	Intermediate Similarity	NPC470499
0.7548	Intermediate Similarity	NPC54744
0.754	Intermediate Similarity	NPC201700
0.7535	Intermediate Similarity	NPC57690
0.7525	Intermediate Similarity	NPC475506
0.7523	Intermediate Similarity	NPC141428
0.7513	Intermediate Similarity	NPC470205
0.7512	Intermediate Similarity	NPC293917
0.7512	Intermediate Similarity	NPC290529
0.7512	Intermediate Similarity	NPC472297
0.7512	Intermediate Similarity	NPC472296
0.75	Intermediate Similarity	NPC6865
0.75	Intermediate Similarity	NPC477042
0.75	Intermediate Similarity	NPC230869
0.75	Intermediate Similarity	NPC219087
0.75	Intermediate Similarity	NPC153980
0.75	Intermediate Similarity	NPC477043
0.75	Intermediate Similarity	NPC91179
0.7488	Intermediate Similarity	NPC477714
0.7488	Intermediate Similarity	NPC472762
0.7488	Intermediate Similarity	NPC155143
0.7488	Intermediate Similarity	NPC281049
0.7487	Intermediate Similarity	NPC248454

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 NPC74413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	611
0.2-0.3	735
0.3-0.4	1825
0.4-0.5	2673
0.5-0.6	2085
0.6-0.7	864
0.7-0.8	132
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
0.8308	Intermediate Similarity	NPD5426	Phase 3
0.8162	Intermediate Similarity	NPD6595	Phase 3
0.8032	Intermediate Similarity	NPD2091	Phase 2
0.8032	Intermediate Similarity	NPD2096	Phase 2
0.8	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD2095	Phase 2
0.7979	Intermediate Similarity	NPD2094	Phase 2
0.7979	Intermediate Similarity	NPD2092	Phase 2
0.7959	Intermediate Similarity	NPD6999	Discontinued
0.7959	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD482	Approved
0.794	Intermediate Similarity	NPD5901	Discontinued
0.7937	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD6242	Discontinued
0.79	Intermediate Similarity	NPD7001	Phase 3
0.79	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7470	Discontinued
0.7876	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD2509	Approved
0.7822	Intermediate Similarity	NPD2510	Approved
0.7789	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD750	Phase 2
0.7688	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6987	Phase 1
0.7672	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7666	Phase 3
0.7647	Intermediate Similarity	NPD7665	Phase 2
0.7629	Intermediate Similarity	NPD8431	Approved
0.7585	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4499	Approved
0.7549	Intermediate Similarity	NPD2008	Discontinued
0.7549	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD7957	Phase 1
0.7537	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5818	Discontinued
0.7512	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3947	Discontinued
0.75	Intermediate Similarity	NPD2411	Approved
0.75	Intermediate Similarity	NPD7948	Phase 1
0.75	Intermediate Similarity	NPD4852	Phase 2
0.7488	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD8073	Approved
0.7488	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7944	Discontinued
0.7476	Intermediate Similarity	NPD3389	Approved
0.7476	Intermediate Similarity	NPD3394	Approved
0.7476	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD3393	Approved
0.7475	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD5065	Approved
0.7454	Intermediate Similarity	NPD6165	Phase 2
0.7454	Intermediate Similarity	NPD6164	Phase 2
0.7451	Intermediate Similarity	NPD8072	Approved
0.745	Intermediate Similarity	NPD4848	Phase 1
0.7411	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2144	Approved
0.7389	Intermediate Similarity	NPD4501	Approved
0.7389	Intermediate Similarity	NPD484	Approved
0.7389	Intermediate Similarity	NPD4500	Approved
0.7378	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7791	Approved
0.7364	Intermediate Similarity	NPD7952	Approved
0.7364	Intermediate Similarity	NPD7953	Approved
0.7364	Intermediate Similarity	NPD7950	Approved
0.7364	Intermediate Similarity	NPD7951	Approved
0.7364	Intermediate Similarity	NPD7790	Approved
0.7364	Intermediate Similarity	NPD7789	Approved
0.7363	Intermediate Similarity	NPD2172	Phase 1
0.735	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD1038	Approved
0.7345	Intermediate Similarity	NPD786	Approved
0.7343	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7780	Approved
0.7339	Intermediate Similarity	NPD7781	Approved
0.7333	Intermediate Similarity	NPD3320	Approved
0.7333	Intermediate Similarity	NPD3319	Phase 1
0.7333	Intermediate Similarity	NPD3318	Approved
0.7331	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5473	Discontinued
0.7313	Intermediate Similarity	NPD7618	Phase 3
0.7313	Intermediate Similarity	NPD7619	Phase 3
0.7304	Intermediate Similarity	NPD4601	Approved
0.7304	Intermediate Similarity	NPD4600	Approved
0.7296	Intermediate Similarity	NPD7564	Discontinued
0.7294	Intermediate Similarity	NPD7731	Approved
0.7294	Intermediate Similarity	NPD7730	Approved
0.7289	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5088	Discontinued
0.7282	Intermediate Similarity	NPD6176	Phase 1
0.7282	Intermediate Similarity	NPD3038	Discontinued
0.7281	Intermediate Similarity	NPD7271	Approved
0.7277	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD6995	Phase 1
0.7268	Intermediate Similarity	NPD4076	Approved
0.7268	Intermediate Similarity	NPD4079	Approved
0.7263	Intermediate Similarity	NPD1722	Approved
0.7263	Intermediate Similarity	NPD2844	Phase 3
0.7263	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4075	Phase 2
0.7251	Intermediate Similarity	NPD8093	Discontinued
0.7249	Intermediate Similarity	NPD5482	Discontinued
0.7248	Intermediate Similarity	NPD7603	Discontinued
0.7241	Intermediate Similarity	NPD6664	Approved
0.7233	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD7824	Approved
0.7227	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6531	Approved
0.7222	Intermediate Similarity	NPD6217	Discontinued
0.7222	Intermediate Similarity	NPD6530	Approved
0.722	Intermediate Similarity	NPD6479	Discontinued
0.7217	Intermediate Similarity	NPD8094	Discontinued
0.7216	Intermediate Similarity	NPD3506	Approved
0.7216	Intermediate Similarity	NPD3505	Approved
0.7213	Intermediate Similarity	NPD3100	Discontinued
0.7204	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD2837	Discontinued
0.7189	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4429	Discontinued
0.7157	Intermediate Similarity	NPD2880	Discontinued
0.7157	Intermediate Similarity	NPD5003	Discontinued
0.715	Intermediate Similarity	NPD2881	Approved
0.715	Intermediate Similarity	NPD2879	Approved
0.7143	Intermediate Similarity	NPD2479	Phase 3
0.7143	Intermediate Similarity	NPD2481	Approved
0.7136	Intermediate Similarity	NPD4845	Discontinued
0.7136	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6178	Phase 3
0.712	Intermediate Similarity	NPD2642	Approved
0.712	Intermediate Similarity	NPD2639	Approved
0.7117	Intermediate Similarity	NPD7688	Phase 1
0.7116	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3178	Discontinued
0.7105	Intermediate Similarity	NPD3323	Discontinued
0.71	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3905	Phase 3
0.7094	Intermediate Similarity	NPD802	Phase 2
0.7087	Intermediate Similarity	NPD3825	Phase 3
0.7083	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8282	Approved
0.7081	Intermediate Similarity	NPD4462	Approved
0.7081	Intermediate Similarity	NPD3835	Phase 3
0.7081	Intermediate Similarity	NPD4463	Approved
0.7081	Intermediate Similarity	NPD8283	Approved
0.7081	Intermediate Similarity	NPD56	Approved
0.7081	Intermediate Similarity	NPD8272	Phase 2
0.7081	Intermediate Similarity	NPD3833	Phase 3
0.7075	Intermediate Similarity	NPD4051	Discontinued
0.7062	Intermediate Similarity	NPD2443	Approved
0.7062	Intermediate Similarity	NPD2442	Approved
0.7056	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1325	Approved
0.7047	Intermediate Similarity	NPD1326	Approved
0.7044	Intermediate Similarity	NPD4922	Phase 2
0.7042	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5475	Discontinued
0.7041	Intermediate Similarity	NPD7865	Approved
0.7027	Intermediate Similarity	NPD5559	Phase 2
0.7023	Intermediate Similarity	NPD7970	Approved
0.7023	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5017	Discontinued
0.7015	Intermediate Similarity	NPD4948	Discontinued
0.7014	Intermediate Similarity	NPD8322	Phase 2
0.701	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD4952	Phase 3
0.6995	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2336	Approved
0.6991	Remote Similarity	NPD3006	Discontinued
0.6991	Remote Similarity	NPD5612	Discontinued
0.6985	Remote Similarity	NPD5106	Approved
0.6985	Remote Similarity	NPD5105	Approved
0.6983	Remote Similarity	NPD4558	Phase 2
0.6981	Remote Similarity	NPD6459	Phase 2
0.698	Remote Similarity	NPD1534	Approved
0.698	Remote Similarity	NPD7234	Approved
0.698	Remote Similarity	NPD7233	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