NPASS Compound

Structure

CID33421 OpenBabel06191715362D 23 26 0 0 1 0 0 0 0 0999 V2000 0.6690 3.2220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5343 -0.4777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6923 3.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3964 2.5589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9243 2.3123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3444 2.3761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5693 -1.8126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3541 -1.3595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7847 -1.3595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9237 -0.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3546 1.3589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7088 0.9054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7086 -0.0008 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3542 -0.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1390 -0.0004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5695 0.9060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7846 -0.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1392 0.9058 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5696 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7849 1.3591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5505 2.2343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9241 1.3587 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 23 1 0 0 0 0 6 21 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 14 1 0 0 0 0 9 17 2 0 0 0 0 10 13 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 2 1 1 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 10 1 1 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 20 2 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 11 1 6 0 0 0 18 23 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.23
Volume:	346.358
LogP:	5.567
LogD:	4.418
LogS:	-5.693
# Rotatable Bonds:	2
TPSA:	19.03
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	3.986
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.958
MDCK Permeability:	1.3776569176116027e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.672
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.16

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.962
Plasma Protein Binding (PPB):	93.02977752685547%
Volume Distribution (VD):	2.228
Pgp-substrate:	6.978592872619629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.547
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.35
CYP2C19-substrate:	0.959
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.615
CYP2D6-inhibitor:	0.977
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.363
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	3.29
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.774
Human Hepatotoxicity (H-HT):	0.486
Drug-inuced Liver Injury (DILI):	0.28
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.956
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.885
Carcinogencity:	0.174
Eye Corrosion:	0.015
Eye Irritation:	0.051
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC33421

Natural Product ID:	NPC33421
*Common Name:**	9-Deacetoxyfumigaclavine C
IUPAC Name:	(6aR,9R,10aR)-7,9-dimethyl-5-(2-methylbut-3-en-2-yl)-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline
Synonyms:	9-Deacetoxyfumigaclavine C
Standard InCHIKey:	GXEMWNLJOIOIIM-DDUZABMNSA-N
Standard InCHI:	InChI=1S/C21H28N2/c1-6-21(3,4)20-16-11-18-15(10-13(2)12-23(18)5)14-8-7-9-17(22-20)19(14)16/h6-9,13,15,18,22H,1,10-12H2,2-5H3/t13-,15-,18-/m1/s1
SMILES:	C=CC(C)(C)c1c2C[C@@H]3[C@H](C[C@@H](C)CN3C)c3cccc(c23)[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561363
PubChem CID:	42640299
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002679] Ergoline and derivatives [CHEMONTID:0002747] Clavines and derivatives

*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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	3100.0	nM	PMID[521636]

☑ 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 NPC33421 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	913
0.1-0.2	6566
0.2-0.3	22050
0.3-0.4	6995
0.4-0.5	2762
0.5-0.6	1920
0.6-0.7	1020
0.7-0.8	388
0.8-0.85	60
0.85-0.9	17
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9324	High Similarity	NPC56765
0.9067	High Similarity	NPC41257
0.9067	High Similarity	NPC318065
0.9067	High Similarity	NPC206819
0.9041	High Similarity	NPC21605
0.9041	High Similarity	NPC477134
0.9021	High Similarity	NPC2949
0.9	High Similarity	NPC286427
0.8958	High Similarity	NPC63157
0.8958	High Similarity	NPC473868
0.8889	High Similarity	NPC59084
0.8819	High Similarity	NPC88097
0.8803	High Similarity	NPC198988
0.8766	High Similarity	NPC90723
0.8758	High Similarity	NPC215584
0.8758	High Similarity	NPC44773
0.8741	High Similarity	NPC325252
0.869	High Similarity	NPC312092
0.8642	High Similarity	NPC19679
0.8592	High Similarity	NPC475450
0.8544	High Similarity	NPC194411
0.8521	High Similarity	NPC22079
0.8521	High Similarity	NPC475428
0.8462	Intermediate Similarity	NPC179365
0.8452	Intermediate Similarity	NPC474880
0.8452	Intermediate Similarity	NPC475990
0.8452	Intermediate Similarity	NPC221786
0.8452	Intermediate Similarity	NPC6436
0.8451	Intermediate Similarity	NPC473587
0.8408	Intermediate Similarity	NPC162799
0.8403	Intermediate Similarity	NPC473930
0.8397	Intermediate Similarity	NPC229173
0.8385	Intermediate Similarity	NPC37423
0.8385	Intermediate Similarity	NPC275305
0.838	Intermediate Similarity	NPC473762
0.8369	Intermediate Similarity	NPC250361
0.8356	Intermediate Similarity	NPC218268
0.8344	Intermediate Similarity	NPC176199
0.8344	Intermediate Similarity	NPC215795
0.8323	Intermediate Similarity	NPC184476
0.8323	Intermediate Similarity	NPC51054
0.8311	Intermediate Similarity	NPC73767
0.8291	Intermediate Similarity	NPC472587
0.8282	Intermediate Similarity	NPC68354
0.8278	Intermediate Similarity	NPC470440
0.8278	Intermediate Similarity	NPC204141
0.8267	Intermediate Similarity	NPC20144
0.8258	Intermediate Similarity	NPC38736
0.8255	Intermediate Similarity	NPC115611
0.8255	Intermediate Similarity	NPC469784
0.8255	Intermediate Similarity	NPC469768
0.8255	Intermediate Similarity	NPC469783
0.8255	Intermediate Similarity	NPC469779
0.8255	Intermediate Similarity	NPC469780
0.8255	Intermediate Similarity	NPC469767
0.8255	Intermediate Similarity	NPC469761
0.8247	Intermediate Similarity	NPC470233
0.8235	Intermediate Similarity	NPC37548
0.8214	Intermediate Similarity	NPC41174
0.82	Intermediate Similarity	NPC469766
0.8199	Intermediate Similarity	NPC280548
0.8188	Intermediate Similarity	NPC110126
0.8188	Intermediate Similarity	NPC104483
0.8182	Intermediate Similarity	NPC53947
0.8176	Intermediate Similarity	NPC21174
0.8176	Intermediate Similarity	NPC84911
0.8176	Intermediate Similarity	NPC271797
0.816	Intermediate Similarity	NPC329688
0.816	Intermediate Similarity	NPC189812
0.8118	Intermediate Similarity	NPC95783
0.8117	Intermediate Similarity	NPC2272
0.8117	Intermediate Similarity	NPC124005
0.8117	Intermediate Similarity	NPC187951
0.8108	Intermediate Similarity	NPC96102
0.8108	Intermediate Similarity	NPC29886
0.8108	Intermediate Similarity	NPC261195
0.8092	Intermediate Similarity	NPC242556
0.8086	Intermediate Similarity	NPC474897
0.8077	Intermediate Similarity	NPC325903
0.8054	Intermediate Similarity	NPC314102
0.8054	Intermediate Similarity	NPC105127
0.8054	Intermediate Similarity	NPC251722
0.8052	Intermediate Similarity	NPC179787
0.8052	Intermediate Similarity	NPC201380
0.8025	Intermediate Similarity	NPC470507
0.8013	Intermediate Similarity	NPC284635
0.8	Intermediate Similarity	NPC16667
0.8	Intermediate Similarity	NPC169433
0.8	Intermediate Similarity	NPC321911
0.7987	Intermediate Similarity	NPC288838
0.7987	Intermediate Similarity	NPC63545
0.7975	Intermediate Similarity	NPC285469
0.7972	Intermediate Similarity	NPC122718
0.7935	Intermediate Similarity	NPC469811
0.7933	Intermediate Similarity	NPC125746
0.7925	Intermediate Similarity	NPC216643
0.7922	Intermediate Similarity	NPC314372
0.7914	Intermediate Similarity	NPC317430
0.7914	Intermediate Similarity	NPC201700
0.7914	Intermediate Similarity	NPC154293
0.7911	Intermediate Similarity	NPC476219
0.7908	Intermediate Similarity	NPC190296
0.7895	Intermediate Similarity	NPC279081
0.7892	Intermediate Similarity	NPC280852
0.7879	Intermediate Similarity	NPC472123
0.7871	Intermediate Similarity	NPC129042
0.7857	Intermediate Similarity	NPC81561
0.7848	Intermediate Similarity	NPC200743
0.7844	Intermediate Similarity	NPC151939
0.7838	Intermediate Similarity	NPC82295
0.7834	Intermediate Similarity	NPC105818
0.7834	Intermediate Similarity	NPC24678
0.7824	Intermediate Similarity	NPC472294
0.7818	Intermediate Similarity	NPC6982
0.7817	Intermediate Similarity	NPC215519
0.7803	Intermediate Similarity	NPC329858
0.7801	Intermediate Similarity	NPC162689
0.7801	Intermediate Similarity	NPC54102
0.7799	Intermediate Similarity	NPC207726
0.7799	Intermediate Similarity	NPC476297
0.7786	Intermediate Similarity	NPC148140
0.7778	Intermediate Similarity	NPC230002
0.7771	Intermediate Similarity	NPC161861
0.777	Intermediate Similarity	NPC282398
0.7764	Intermediate Similarity	NPC67056
0.7756	Intermediate Similarity	NPC143872
0.7751	Intermediate Similarity	NPC300688
0.7736	Intermediate Similarity	NPC259644
0.7736	Intermediate Similarity	NPC469760
0.7736	Intermediate Similarity	NPC200214
0.7736	Intermediate Similarity	NPC469765
0.7736	Intermediate Similarity	NPC469763
0.7736	Intermediate Similarity	NPC469786
0.7736	Intermediate Similarity	NPC25008
0.7736	Intermediate Similarity	NPC73952
0.773	Intermediate Similarity	NPC317105
0.7722	Intermediate Similarity	NPC40070
0.7716	Intermediate Similarity	NPC473320
0.7714	Intermediate Similarity	NPC314058
0.7714	Intermediate Similarity	NPC316359
0.7714	Intermediate Similarity	NPC315617
0.7714	Intermediate Similarity	NPC316018
0.7707	Intermediate Similarity	NPC471957
0.7702	Intermediate Similarity	NPC236711
0.7697	Intermediate Similarity	NPC150259
0.7692	Intermediate Similarity	NPC159856
0.7688	Intermediate Similarity	NPC211572
0.7688	Intermediate Similarity	NPC80597
0.7688	Intermediate Similarity	NPC471458
0.7688	Intermediate Similarity	NPC75540
0.7688	Intermediate Similarity	NPC212376
0.7688	Intermediate Similarity	NPC70922
0.7674	Intermediate Similarity	NPC476319
0.7669	Intermediate Similarity	NPC470203
0.7665	Intermediate Similarity	NPC97525
0.7665	Intermediate Similarity	NPC34508
0.7661	Intermediate Similarity	NPC470205
0.7654	Intermediate Similarity	NPC135141
0.7654	Intermediate Similarity	NPC92796
0.7636	Intermediate Similarity	NPC474561
0.7636	Intermediate Similarity	NPC49954
0.7624	Intermediate Similarity	NPC162730
0.7622	Intermediate Similarity	NPC271734
0.7622	Intermediate Similarity	NPC247987
0.761	Intermediate Similarity	NPC148592
0.7607	Intermediate Similarity	NPC470204
0.7607	Intermediate Similarity	NPC122141
0.7607	Intermediate Similarity	NPC81229
0.7607	Intermediate Similarity	NPC255229
0.7605	Intermediate Similarity	NPC201634
0.76	Intermediate Similarity	NPC314333
0.7593	Intermediate Similarity	NPC299594
0.759	Intermediate Similarity	NPC63751
0.7588	Intermediate Similarity	NPC213468
0.7578	Intermediate Similarity	NPC34844
0.7576	Intermediate Similarity	NPC470508
0.7574	Intermediate Similarity	NPC288785
0.7574	Intermediate Similarity	NPC474958
0.7562	Intermediate Similarity	NPC470823
0.7561	Intermediate Similarity	NPC194881
0.7558	Intermediate Similarity	NPC139291
0.7558	Intermediate Similarity	NPC472108
0.7542	Intermediate Similarity	NPC229332
0.7531	Intermediate Similarity	NPC469785
0.753	Intermediate Similarity	NPC160105
0.753	Intermediate Similarity	NPC109447
0.7527	Intermediate Similarity	NPC474116
0.7516	Intermediate Similarity	NPC141926
0.75	Intermediate Similarity	NPC82331
0.7485	Intermediate Similarity	NPC270009
0.7485	Intermediate Similarity	NPC469762
0.7485	Intermediate Similarity	NPC6093
0.7484	Intermediate Similarity	NPC470111
0.7483	Intermediate Similarity	NPC264580
0.7468	Intermediate Similarity	NPC469525
0.7459	Intermediate Similarity	NPC32200
0.7455	Intermediate Similarity	NPC282231
0.7453	Intermediate Similarity	NPC216713
0.7444	Intermediate Similarity	NPC232130
0.7442	Intermediate Similarity	NPC198339

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 NPC33421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	645
0.2-0.3	1124
0.3-0.4	1835
0.4-0.5	2462
0.5-0.6	1880
0.6-0.7	641
0.7-0.8	125
0.8-0.85	20
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD5744	Clinical (unspecified phase)
0.9231	High Similarity	NPD5254	Discontinued
0.9139	High Similarity	NPD3323	Discontinued
0.891	High Similarity	NPD4112	Clinical (unspecified phase)
0.8889	High Similarity	NPD3943	Clinical (unspecified phase)
0.8846	High Similarity	NPD3610	Approved
0.8846	High Similarity	NPD3609	Approved
0.8716	High Similarity	NPD1683	Approved
0.8639	High Similarity	NPD4637	Clinical (unspecified phase)
0.8625	High Similarity	NPD4181	Approved
0.8481	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD3385	Approved
0.8446	Intermediate Similarity	NPD1722	Approved
0.8355	Intermediate Similarity	NPD3100	Discontinued
0.8344	Intermediate Similarity	NPD5315	Discontinued
0.8333	Intermediate Similarity	NPD4075	Phase 2
0.8311	Intermediate Similarity	NPD786	Approved
0.8301	Intermediate Similarity	NPD2172	Phase 1
0.8299	Intermediate Similarity	NPD1262	Discovery
0.8282	Intermediate Similarity	NPD3506	Approved
0.8282	Intermediate Similarity	NPD3505	Approved
0.8272	Intermediate Similarity	NPD4128	Approved
0.8232	Intermediate Similarity	NPD4079	Approved
0.8232	Intermediate Similarity	NPD4076	Approved
0.8214	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2150	Discontinued
0.8194	Intermediate Similarity	NPD2837	Discontinued
0.8182	Intermediate Similarity	NPD4462	Approved
0.8182	Intermediate Similarity	NPD4463	Approved
0.8176	Intermediate Similarity	NPD6554	Approved
0.8176	Intermediate Similarity	NPD45	Approved
0.8117	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD3654	Approved
0.8041	Intermediate Similarity	NPD4880	Discontinued
0.8025	Intermediate Similarity	NPD2640	Approved
0.8025	Intermediate Similarity	NPD5021	Discontinued
0.8025	Intermediate Similarity	NPD2641	Approved
0.8	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1256	Approved
0.7987	Intermediate Similarity	NPD1255	Approved
0.7987	Intermediate Similarity	NPD1254	Approved
0.7987	Intermediate Similarity	NPD1253	Approved
0.7965	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4547	Phase 3
0.7895	Intermediate Similarity	NPD3961	Discontinued
0.7892	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2580	Discontinued
0.7857	Intermediate Similarity	NPD5473	Discontinued
0.7841	Intermediate Similarity	NPD6664	Approved
0.7838	Intermediate Similarity	NPD1251	Discontinued
0.7824	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD947	Approved
0.7805	Intermediate Similarity	NPD4639	Approved
0.7805	Intermediate Similarity	NPD4638	Approved
0.7805	Intermediate Similarity	NPD4640	Approved
0.7791	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3475	Approved
0.777	Intermediate Similarity	NPD3476	Approved
0.7758	Intermediate Similarity	NPD1326	Approved
0.7758	Intermediate Similarity	NPD1325	Approved
0.7751	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4028	Approved
0.7733	Intermediate Similarity	NPD4029	Approved
0.7733	Intermediate Similarity	NPD4030	Approved
0.7725	Intermediate Similarity	NPD5065	Approved
0.7716	Intermediate Similarity	NPD1403	Approved
0.7716	Intermediate Similarity	NPD1404	Approved
0.7711	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6828	Phase 2
0.7701	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2118	Approved
0.7687	Intermediate Similarity	NPD2119	Approved
0.7674	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD2642	Approved
0.7636	Intermediate Similarity	NPD2639	Approved
0.763	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3944	Approved
0.7616	Intermediate Similarity	NPD3942	Approved
0.76	Intermediate Similarity	NPD4499	Approved
0.759	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD975	Approved
0.7578	Intermediate Similarity	NPD977	Approved
0.7578	Intermediate Similarity	NPD976	Approved
0.7564	Intermediate Similarity	NPD4047	Discontinued
0.7558	Intermediate Similarity	NPD3320	Approved
0.7558	Intermediate Similarity	NPD3319	Phase 1
0.7558	Intermediate Similarity	NPD3318	Approved
0.7516	Intermediate Similarity	NPD4509	Discontinued
0.7486	Intermediate Similarity	NPD8431	Approved
0.7485	Intermediate Similarity	NPD4326	Phase 2
0.7485	Intermediate Similarity	NPD8386	Phase 2
0.7466	Intermediate Similarity	NPD5787	Discontinued
0.7457	Intermediate Similarity	NPD5106	Approved
0.7457	Intermediate Similarity	NPD5105	Approved
0.7452	Intermediate Similarity	NPD2006	Phase 2
0.745	Intermediate Similarity	NPD991	Phase 2
0.745	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5436	Phase 1
0.744	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2430	Phase 2
0.7427	Intermediate Similarity	NPD2144	Approved
0.7423	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3799	Suspended
0.741	Intermediate Similarity	NPD3583	Phase 2
0.7401	Intermediate Similarity	NPD6281	Approved
0.7399	Intermediate Similarity	NPD3038	Discontinued
0.7396	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5730	Phase 2
0.7384	Intermediate Similarity	NPD40	Phase 2
0.7362	Intermediate Similarity	NPD6285	Phase 2
0.7354	Intermediate Similarity	NPD7454	Approved
0.7354	Intermediate Similarity	NPD7455	Approved
0.7346	Intermediate Similarity	NPD2882	Phase 1
0.7342	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7619	Phase 3
0.7333	Intermediate Similarity	NPD7618	Phase 3
0.733	Intermediate Similarity	NPD6217	Discontinued
0.7329	Intermediate Similarity	NPD4811	Discontinued
0.7317	Intermediate Similarity	NPD3113	Approved
0.7317	Intermediate Similarity	NPD3114	Approved
0.7317	Intermediate Similarity	NPD3112	Approved
0.7317	Intermediate Similarity	NPD3115	Approved
0.7288	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3835	Phase 3
0.7284	Intermediate Similarity	NPD3833	Phase 3
0.7278	Intermediate Similarity	NPD5020	Approved
0.7273	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4702	Approved
0.7267	Intermediate Similarity	NPD4703	Approved
0.7262	Intermediate Similarity	NPD2915	Discontinued
0.7257	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2165	Phase 1
0.7246	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6595	Phase 3
0.7241	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6158	Phase 2
0.7239	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2038	Approved
0.7234	Intermediate Similarity	NPD2039	Approved
0.7228	Intermediate Similarity	NPD4601	Approved
0.7228	Intermediate Similarity	NPD4600	Approved
0.72	Intermediate Similarity	NPD1895	Discontinued
0.72	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4511	Phase 1
0.7176	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1592	Phase 3
0.7168	Intermediate Similarity	NPD5104	Approved
0.7167	Intermediate Similarity	NPD5913	Phase 3
0.7167	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD271	Approved
0.7162	Intermediate Similarity	NPD268	Approved
0.716	Intermediate Similarity	NPD509	Phase 3
0.7152	Intermediate Similarity	NPD2069	Approved
0.7152	Intermediate Similarity	NPD2071	Approved
0.7152	Intermediate Similarity	NPD2068	Approved
0.7152	Intermediate Similarity	NPD2070	Approved
0.7152	Intermediate Similarity	NPD2074	Approved
0.7152	Intermediate Similarity	NPD2075	Approved
0.7152	Intermediate Similarity	NPD2073	Approved
0.7152	Intermediate Similarity	NPD2072	Approved
0.7143	Intermediate Similarity	NPD5962	Phase 2
0.7126	Intermediate Similarity	NPD7111	Discontinued
0.7126	Intermediate Similarity	NPD4398	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2927	Phase 3
0.7104	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD1707	Approved
0.7102	Intermediate Similarity	NPD1708	Approved
0.7101	Intermediate Similarity	NPD5138	Approved
0.7101	Intermediate Similarity	NPD5140	Approved
0.7092	Intermediate Similarity	NPD4116	Approved
0.7091	Intermediate Similarity	NPD3339	Approved
0.7083	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1648	Phase 1
0.7066	Intermediate Similarity	NPD1647	Phase 1
0.7066	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1313	Approved
0.7056	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD680	Discontinued
0.7044	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9583	Approved
0.703	Intermediate Similarity	NPD4641	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