NPASS Compound

Structure

CID317709 OpenBabel06191716142D 28 34 0 0 1 0 0 0 0 0999 V2000 -1.7600 2.3270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9469 2.1297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1092 2.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0158 0.8191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3206 -0.4311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5370 1.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0430 2.2287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6590 0.2002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9635 0.2897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6937 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0880 1.4381 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0747 0.7496 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7175 -0.0983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5984 1.8772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9104 -0.0752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0317 1.4790 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7041 0.5904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8970 0.6135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2939 0.9463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6510 0.2255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0450 0.7905 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0666 -0.3238 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6162 2.0285 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3974 2.1258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2788 1.7265 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 3.5695 -0.2753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5479 0.8391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 25 1 0 0 0 0 3 10 2 0 0 0 0 4 16 1 0 0 0 0 5 13 2 0 0 0 0 5 15 1 0 0 0 0 7 10 1 0 0 0 0 7 23 1 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 9 28 1 0 0 0 0 10 11 1 0 0 0 0 11 4 1 1 0 0 0 11 12 1 0 0 0 0 12 8 1 1 0 0 0 12 14 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 6 1 6 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 15 27 1 0 0 0 0 16 21 1 6 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 6 1 6 0 0 0 23 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.15
Volume:	364.639
LogP:	1.002
LogD:	1.327
LogS:	-2.063
# Rotatable Bonds:	1
TPSA:	72.34
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	7.04
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.144
MDCK Permeability:	2.8106776881031692e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.848
Human Intestinal Absorption (HIA):	0.409
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.903
Plasma Protein Binding (PPB):	88.2427978515625%
Volume Distribution (VD):	2.16
Pgp-substrate:	5.869739532470703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.442
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.64
CYP2C9-inhibitor:	0.104
CYP2C9-substrate:	0.669
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.385
CYP3A4-inhibitor:	0.842
CYP3A4-substrate:	0.831

ADMET: Excretion

Clearance (CL):	8.06
Half-life (T1/2):	0.658

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.524
Drug-inuced Liver Injury (DILI):	0.47
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.809
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.643
Carcinogencity:	0.925
Eye Corrosion:	0.031
Eye Irritation:	0.488
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC317709

Natural Product ID:	NPC317709
*Common Name:**	DQZDTIUNCHBKJR-NBSCQXKLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DQZDTIUNCHBKJR-NBSCQXKLSA-N
Standard InCHI:	InChI=1S/C21H22N2O5/c1-3-10-7-23(24)14-6-21-16(23)4-11(10)12(14)8-26-20(21)22-13-5-15-18(28-9-27-15)19(25-2)17(13)21/h3,5,11-12,14,16H,4,6-9H2,1-2H3/b10-3-/t11-,12-,14-,16-,21-,23?/m0/s1
SMILES:	CC=C1C[N+]2(C3CC1C4C2CC35C6=C(C7=C(C=C6N=C5OC4)OCO7)OC)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782231
PubChem CID:	54585002
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO4208	Gardneria ovata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21425787]
NPO4208	Gardneria ovata	Species	Loganiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21425787]
NPO4208	Gardneria ovata	Species	Loganiaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[559986]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[559986]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[559986]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[559986]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[559986]

☑ 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 NPC317709 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	545
0.1-0.2	2060
0.2-0.3	7632
0.3-0.4	10942
0.4-0.5	12234
0.5-0.6	7768
0.6-0.7	1417
0.7-0.8	92
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329329
0.9319	High Similarity	NPC168250
0.89	High Similarity	NPC108826
0.8743	High Similarity	NPC272706
0.8115	Intermediate Similarity	NPC98197
0.8	Intermediate Similarity	NPC217294
0.7708	Intermediate Similarity	NPC75958
0.7592	Intermediate Similarity	NPC180306
0.7588	Intermediate Similarity	NPC9867
0.7577	Intermediate Similarity	NPC65403
0.7537	Intermediate Similarity	NPC471113
0.7475	Intermediate Similarity	NPC244554
0.7449	Intermediate Similarity	NPC228040
0.7411	Intermediate Similarity	NPC187678
0.7337	Intermediate Similarity	NPC15919
0.731	Intermediate Similarity	NPC10871
0.7277	Intermediate Similarity	NPC470821
0.7259	Intermediate Similarity	NPC311991
0.7245	Intermediate Similarity	NPC57812
0.7245	Intermediate Similarity	NPC474324
0.7228	Intermediate Similarity	NPC73492
0.7228	Intermediate Similarity	NPC299990
0.7208	Intermediate Similarity	NPC475845
0.7198	Intermediate Similarity	NPC29472
0.7184	Intermediate Similarity	NPC63152
0.7176	Intermediate Similarity	NPC82541
0.7172	Intermediate Similarity	NPC474708
0.7157	Intermediate Similarity	NPC100566
0.7157	Intermediate Similarity	NPC298186
0.7157	Intermediate Similarity	NPC301189
0.715	Intermediate Similarity	NPC302001
0.7149	Intermediate Similarity	NPC318525
0.7149	Intermediate Similarity	NPC10653
0.7136	Intermediate Similarity	NPC57272
0.7136	Intermediate Similarity	NPC477640
0.7136	Intermediate Similarity	NPC19520
0.7136	Intermediate Similarity	NPC225597
0.7136	Intermediate Similarity	NPC149090
0.7136	Intermediate Similarity	NPC470739
0.7135	Intermediate Similarity	NPC78733
0.7128	Intermediate Similarity	NPC70172
0.7122	Intermediate Similarity	NPC477186
0.7121	Intermediate Similarity	NPC158148
0.7121	Intermediate Similarity	NPC82533
0.7121	Intermediate Similarity	NPC266176
0.7121	Intermediate Similarity	NPC290759
0.7109	Intermediate Similarity	NPC127178
0.7098	Intermediate Similarity	NPC146288
0.7092	Intermediate Similarity	NPC320104
0.709	Intermediate Similarity	NPC37144
0.709	Intermediate Similarity	NPC59907
0.7087	Intermediate Similarity	NPC312531
0.7085	Intermediate Similarity	NPC474475
0.7085	Intermediate Similarity	NPC250960
0.7085	Intermediate Similarity	NPC71539
0.7071	Intermediate Similarity	NPC181653
0.7071	Intermediate Similarity	NPC190332
0.7065	Intermediate Similarity	NPC304675
0.7064	Intermediate Similarity	NPC159815
0.7056	Intermediate Similarity	NPC247972
0.7053	Intermediate Similarity	NPC281581
0.7047	Intermediate Similarity	NPC138487
0.7047	Intermediate Similarity	NPC216459
0.7047	Intermediate Similarity	NPC41178
0.7042	Intermediate Similarity	NPC474077
0.7041	Intermediate Similarity	NPC24954
0.7035	Intermediate Similarity	NPC58766
0.7035	Intermediate Similarity	NPC475686
0.7031	Intermediate Similarity	NPC148898
0.703	Intermediate Similarity	NPC474470
0.703	Intermediate Similarity	NPC237044
0.7022	Intermediate Similarity	NPC231924
0.702	Intermediate Similarity	NPC476002
0.7019	Intermediate Similarity	NPC473716
0.7019	Intermediate Similarity	NPC475597
0.7015	Intermediate Similarity	NPC2314
0.701	Intermediate Similarity	NPC31311
0.701	Intermediate Similarity	NPC234392
0.7005	Intermediate Similarity	NPC218614
0.7005	Intermediate Similarity	NPC473008
0.6995	Remote Similarity	NPC148693
0.6995	Remote Similarity	NPC118633
0.6995	Remote Similarity	NPC294790
0.6995	Remote Similarity	NPC474325
0.6991	Remote Similarity	NPC266994
0.699	Remote Similarity	NPC4304
0.6986	Remote Similarity	NPC24260
0.6986	Remote Similarity	NPC203972
0.698	Remote Similarity	NPC49353
0.6977	Remote Similarity	NPC14339
0.6977	Remote Similarity	NPC470484
0.6976	Remote Similarity	NPC233718
0.6971	Remote Similarity	NPC28510
0.6961	Remote Similarity	NPC470879
0.6961	Remote Similarity	NPC474745
0.6961	Remote Similarity	NPC258695
0.6943	Remote Similarity	NPC210148
0.6943	Remote Similarity	NPC233029
0.6942	Remote Similarity	NPC475981
0.6942	Remote Similarity	NPC474746
0.6937	Remote Similarity	NPC195636
0.693	Remote Similarity	NPC74216
0.6927	Remote Similarity	NPC179704
0.6927	Remote Similarity	NPC474506
0.6927	Remote Similarity	NPC32413
0.6923	Remote Similarity	NPC296742
0.6923	Remote Similarity	NPC174629
0.6919	Remote Similarity	NPC162653
0.6906	Remote Similarity	NPC87560
0.6906	Remote Similarity	NPC195120
0.6904	Remote Similarity	NPC215829
0.6904	Remote Similarity	NPC97072
0.69	Remote Similarity	NPC247389
0.69	Remote Similarity	NPC252960
0.69	Remote Similarity	NPC210918
0.6893	Remote Similarity	NPC473007
0.6889	Remote Similarity	NPC128476
0.6884	Remote Similarity	NPC167546
0.6884	Remote Similarity	NPC24465
0.6884	Remote Similarity	NPC302527
0.6884	Remote Similarity	NPC16805
0.6881	Remote Similarity	NPC276890
0.6881	Remote Similarity	NPC76682
0.6881	Remote Similarity	NPC63646
0.6881	Remote Similarity	NPC317145
0.6881	Remote Similarity	NPC198498
0.6881	Remote Similarity	NPC227060
0.6881	Remote Similarity	NPC10908
0.6881	Remote Similarity	NPC317439
0.6881	Remote Similarity	NPC115284
0.6875	Remote Similarity	NPC474661
0.6875	Remote Similarity	NPC224293
0.6875	Remote Similarity	NPC475919
0.6872	Remote Similarity	NPC93593
0.6866	Remote Similarity	NPC182257
0.6866	Remote Similarity	NPC204908
0.6866	Remote Similarity	NPC83198
0.6863	Remote Similarity	NPC283999
0.6863	Remote Similarity	NPC293093
0.6857	Remote Similarity	NPC204970
0.6857	Remote Similarity	NPC473004
0.6853	Remote Similarity	NPC477080
0.6852	Remote Similarity	NPC159101
0.685	Remote Similarity	NPC13916
0.685	Remote Similarity	NPC476432
0.685	Remote Similarity	NPC264850
0.685	Remote Similarity	NPC24264
0.685	Remote Similarity	NPC219341
0.6847	Remote Similarity	NPC232386
0.6847	Remote Similarity	NPC152680
0.6847	Remote Similarity	NPC110374
0.6847	Remote Similarity	NPC190783
0.6847	Remote Similarity	NPC289743
0.6847	Remote Similarity	NPC41376
0.6847	Remote Similarity	NPC251580
0.6847	Remote Similarity	NPC129518
0.6847	Remote Similarity	NPC12424
0.6844	Remote Similarity	NPC118154
0.6844	Remote Similarity	NPC476069
0.6844	Remote Similarity	NPC157983
0.6842	Remote Similarity	NPC112676
0.684	Remote Similarity	NPC476429
0.6833	Remote Similarity	NPC10732
0.6829	Remote Similarity	NPC23219
0.6827	Remote Similarity	NPC180253
0.6827	Remote Similarity	NPC249996
0.6827	Remote Similarity	NPC69213
0.6827	Remote Similarity	NPC219170
0.6823	Remote Similarity	NPC475959
0.682	Remote Similarity	NPC475147
0.6812	Remote Similarity	NPC276060
0.6812	Remote Similarity	NPC249405
0.6808	Remote Similarity	NPC472191
0.6802	Remote Similarity	NPC235628
0.68	Remote Similarity	NPC225774
0.68	Remote Similarity	NPC276944
0.68	Remote Similarity	NPC238530
0.68	Remote Similarity	NPC232514
0.68	Remote Similarity	NPC231198
0.6794	Remote Similarity	NPC214116
0.6794	Remote Similarity	NPC57036
0.6794	Remote Similarity	NPC230098
0.6792	Remote Similarity	NPC230313
0.6791	Remote Similarity	NPC475654
0.678	Remote Similarity	NPC112575
0.678	Remote Similarity	NPC1291
0.678	Remote Similarity	NPC115343
0.678	Remote Similarity	NPC287588
0.6773	Remote Similarity	NPC475133
0.6773	Remote Similarity	NPC477160
0.6763	Remote Similarity	NPC195538
0.6751	Remote Similarity	NPC180756
0.6751	Remote Similarity	NPC323443
0.6748	Remote Similarity	NPC190461
0.6748	Remote Similarity	NPC477560
0.6743	Remote Similarity	NPC156728
0.6743	Remote Similarity	NPC244606
0.6742	Remote Similarity	NPC269449
0.674	Remote Similarity	NPC46259
0.6737	Remote Similarity	NPC476258

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 NPC317709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	677
0.2-0.3	989
0.3-0.4	2559
0.4-0.5	2961
0.5-0.6	1423
0.6-0.7	276
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7171	Intermediate Similarity	NPD2845	Phase 2
0.7171	Intermediate Similarity	NPD2843	Phase 2
0.7067	Intermediate Similarity	NPD7125	Discontinued
0.7031	Intermediate Similarity	NPD6625	Approved
0.7	Intermediate Similarity	NPD5582	Discontinued
0.6931	Remote Similarity	NPD8156	Discontinued
0.6881	Remote Similarity	NPD8252	Approved
0.6881	Remote Similarity	NPD8251	Approved
0.6881	Remote Similarity	NPD8099	Discontinued
0.6866	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6877	Discontinued
0.6766	Remote Similarity	NPD6071	Discontinued
0.6749	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5005	Approved
0.6728	Remote Similarity	NPD5006	Approved
0.6726	Remote Similarity	NPD5519	Discontinued
0.67	Remote Similarity	NPD4481	Phase 3
0.6684	Remote Similarity	NPD4584	Approved
0.6683	Remote Similarity	NPD6788	Approved
0.6682	Remote Similarity	NPD3816	Phase 1
0.6682	Remote Similarity	NPD3815	Phase 1
0.6667	Remote Similarity	NPD6723	Discontinued
0.6652	Remote Similarity	NPD5658	Approved
0.6651	Remote Similarity	NPD8054	Approved
0.6651	Remote Similarity	NPD8053	Approved
0.6637	Remote Similarity	NPD4206	Approved
0.6634	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3983	Phase 3
0.6633	Remote Similarity	NPD2563	Approved
0.6633	Remote Similarity	NPD2560	Approved
0.662	Remote Similarity	NPD3634	Approved
0.662	Remote Similarity	NPD3633	Approved
0.662	Remote Similarity	NPD4740	Approved
0.6617	Remote Similarity	NPD4796	Discontinued
0.66	Remote Similarity	NPD19	Approved
0.66	Remote Similarity	NPD1742	Approved
0.66	Remote Similarity	NPD1743	Approved
0.6599	Remote Similarity	NPD7956	Approved
0.6599	Remote Similarity	NPD5617	Suspended
0.6599	Remote Similarity	NPD3296	Phase 1
0.6599	Remote Similarity	NPD7955	Approved
0.6575	Remote Similarity	NPD3515	Approved
0.6575	Remote Similarity	NPD3516	Approved
0.6574	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2969	Approved
0.6569	Remote Similarity	NPD2970	Approved
0.6567	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3349	Phase 2
0.6552	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD4420	Approved
0.6526	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7311	Approved
0.6524	Remote Similarity	NPD7313	Approved
0.6524	Remote Similarity	NPD7312	Approved
0.6524	Remote Similarity	NPD7310	Approved
0.652	Remote Similarity	NPD3051	Approved
0.6513	Remote Similarity	NPD1424	Approved
0.6513	Remote Similarity	NPD4846	Phase 2
0.6512	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5773	Approved
0.65	Remote Similarity	NPD5772	Approved
0.6495	Remote Similarity	NPD7124	Phase 2
0.6493	Remote Similarity	NPD7309	Approved
0.6482	Remote Similarity	NPD4772	Phase 2
0.6482	Remote Similarity	NPD4773	Phase 2
0.6476	Remote Similarity	NPD7559	Phase 2
0.6471	Remote Similarity	NPD6107	Approved
0.6468	Remote Similarity	NPD7803	Approved
0.6459	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2489	Approved
0.6456	Remote Similarity	NPD27	Approved
0.6443	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD2215	Approved
0.6408	Remote Similarity	NPD2216	Approved
0.6407	Remote Similarity	NPD5930	Phase 3
0.6404	Remote Similarity	NPD5604	Discontinued
0.6404	Remote Similarity	NPD4055	Discovery
0.6402	Remote Similarity	NPD7906	Approved
0.6402	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3591	Approved
0.64	Remote Similarity	NPD3592	Approved
0.6389	Remote Similarity	NPD7296	Approved
0.6388	Remote Similarity	NPD7827	Phase 1
0.6382	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD3383	Approved
0.6368	Remote Similarity	NPD7298	Approved
0.6368	Remote Similarity	NPD3382	Approved
0.6368	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4578	Approved
0.6368	Remote Similarity	NPD4577	Approved
0.6368	Remote Similarity	NPD3384	Approved
0.6364	Remote Similarity	NPD3639	Approved
0.6364	Remote Similarity	NPD3763	Approved
0.6364	Remote Similarity	NPD5600	Discontinued
0.6364	Remote Similarity	NPD3641	Approved
0.6364	Remote Similarity	NPD3640	Phase 3
0.6359	Remote Similarity	NPD3631	Phase 3
0.6355	Remote Similarity	NPD4663	Approved
0.6351	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.635	Remote Similarity	NPD4678	Approved
0.635	Remote Similarity	NPD4675	Approved
0.6347	Remote Similarity	NPD4605	Approved
0.6347	Remote Similarity	NPD4604	Approved
0.6345	Remote Similarity	NPD4885	Approved
0.6343	Remote Similarity	NPD5641	Discontinued
0.634	Remote Similarity	NPD7224	Discontinued
0.634	Remote Similarity	NPD7223	Discontinued
0.6336	Remote Similarity	NPD3437	Discontinued
0.6335	Remote Similarity	NPD6111	Discontinued
0.6332	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD3398	Discontinued
0.6318	Remote Similarity	NPD1440	Discontinued
0.6316	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7263	Phase 2
0.631	Remote Similarity	NPD7708	Approved
0.6305	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4005	Discontinued
0.6293	Remote Similarity	NPD2899	Discontinued
0.629	Remote Similarity	NPD8095	Phase 1
0.629	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5312	Approved
0.6286	Remote Similarity	NPD5313	Approved
0.6281	Remote Similarity	NPD6031	Approved
0.6281	Remote Similarity	NPD2122	Discontinued
0.6281	Remote Similarity	NPD6030	Approved
0.628	Remote Similarity	NPD4166	Phase 2
0.6273	Remote Similarity	NPD7034	Discontinued
0.6266	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6037	Discontinued
0.6262	Remote Similarity	NPD5677	Discontinued
0.6262	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD3912	Discontinued
0.625	Remote Similarity	NPD4210	Discontinued
0.625	Remote Similarity	NPD2200	Suspended
0.625	Remote Similarity	NPD6841	Approved
0.625	Remote Similarity	NPD6494	Phase 2
0.625	Remote Similarity	NPD6843	Phase 3
0.625	Remote Similarity	NPD6842	Approved
0.6237	Remote Similarity	NPD1375	Discontinued
0.6234	Remote Similarity	NPD5561	Approved
0.6234	Remote Similarity	NPD5562	Approved
0.6232	Remote Similarity	NPD3511	Discontinued
0.6228	Remote Similarity	NPD5914	Approved
0.6228	Remote Similarity	NPD5645	Phase 3
0.6225	Remote Similarity	NPD6063	Approved
0.6219	Remote Similarity	NPD5811	Approved
0.6216	Remote Similarity	NPD6874	Approved
0.6216	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD2971	Approved
0.6215	Remote Similarity	NPD7281	Phase 3
0.6215	Remote Similarity	NPD2968	Approved
0.6215	Remote Similarity	NPD7280	Phase 3
0.621	Remote Similarity	NPD5150	Phase 2
0.6205	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4875	Phase 3
0.6204	Remote Similarity	NPD3120	Approved
0.6204	Remote Similarity	NPD3119	Phase 1
0.6204	Remote Similarity	NPD4876	Phase 3
0.6201	Remote Similarity	NPD683	Approved
0.619	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD4083	Discontinued
0.6167	Remote Similarity	NPD6296	Discontinued
0.6166	Remote Similarity	NPD8461	Discontinued
0.6158	Remote Similarity	NPD5089	Approved
0.6158	Remote Similarity	NPD5090	Approved
0.615	Remote Similarity	NPD2167	Clinical (unspecified phase)
0.615	Remote Similarity	NPD2168	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD2898	Approved
0.614	Remote Similarity	NPD4859	Phase 1
0.6139	Remote Similarity	NPD6357	Discontinued
0.6137	Remote Similarity	NPD5545	Phase 2
0.6136	Remote Similarity	NPD5984	Phase 2
0.6129	Remote Similarity	NPD4951	Discontinued
0.6126	Remote Similarity	NPD2974	Approved
0.6126	Remote Similarity	NPD2973	Approved
0.6126	Remote Similarity	NPD2975	Approved
0.6121	Remote Similarity	NPD5903	Approved
0.6121	Remote Similarity	NPD5902	Approved
0.6116	Remote Similarity	NPD4580	Approved
0.6114	Remote Similarity	NPD4917	Discontinued
0.6109	Remote Similarity	NPD4418	Discontinued
0.6109	Remote Similarity	NPD4771	Phase 2
0.6109	Remote Similarity	NPD6493	Phase 3
0.6106	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD2161	Phase 2
0.6103	Remote Similarity	NPD7479	Phase 2

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