NPASS Compound

Structure

CID203972 OpenBabel06191715592D 28 32 0 0 1 0 0 0 0 0999 V2000 2.9033 0.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6006 1.6796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9393 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2660 -2.5820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1856 -2.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9341 -1.1765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8806 -1.1442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2650 -2.5371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7374 -1.9332 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6878 -0.9685 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2447 -1.5172 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2512 -0.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5868 -0.7642 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 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 2.0662 -2.5012 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 3.2306 -0.2185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5337 -2.4637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9362 0.9323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 22 1 0 0 0 0 8 24 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 9 1 6 0 0 0 14 4 1 6 0 0 0 14 18 1 0 0 0 0 15 27 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 1 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 20 1 6 0 0 0 22 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.2
Volume:	390.258
LogP:	2.444
LogD:	2.746
LogS:	-4.316
# Rotatable Bonds:	4
TPSA:	71.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.812
Synthetic Accessibility Score:	5.554
Fsp3:	0.636
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:	-4.903
MDCK Permeability:	1.8505450498196296e-05
Pgp-inhibitor:	0.056
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.357
30% Bioavailability (F30%):	0.692

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.808
Plasma Protein Binding (PPB):	59.12763214111328%
Volume Distribution (VD):	3.239
Pgp-substrate:	42.29166793823242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.148
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.506
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.217
CYP2C9-substrate:	0.134
CYP2D6-inhibitor:	0.334
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.736
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	9.094
Half-life (T1/2):	0.107

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.94
Drug-inuced Liver Injury (DILI):	0.727
AMES Toxicity:	0.402
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.098
Carcinogencity:	0.961
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC203972

Natural Product ID:	NPC203972
*Common Name:**	AVRFPRAAVSCSSZ-YPENQOSPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AVRFPRAAVSCSSZ-YPENQOSPSA-N
Standard InCHI:	InChI=1S/C22H28N2O4/c1-4-14-9-13-11-21(20(25)28-3)18(14)24(12-13)8-7-22(26)16-10-15(27-2)5-6-17(16)23-19(21)22/h5-6,10,13-14,18,26H,4,7-9,11-12H2,1-3H3/t13-,14+,18+,21+,22+/m1/s1
SMILES:	CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(CC[C@@]1(c4cc(ccc4N=C31)OC)O)C2)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3325766
PubChem CID:	22296670
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002748] Ibogan-type alkaloids

*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
NPO23773	Holacantha emoryi	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23978	Dorstenia zenkeri	Species	Moraceae	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
EC50	1
IC50	3
Others	1

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1885	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Mus musculus	IC50	=	126000.0	nM	PMID[504051]
NPT1885	Individual Protein	Transient receptor potential cation channel subfamily M member 8	Mus musculus	IC50	=	110000.0	nM	PMID[504051]
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	Activity	=	87.0	%	PMID[504051]
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	EC50	=	32000.0	nM	PMID[504051]
NPT472	Individual Protein	Vanilloid receptor	Homo sapiens	IC50	=	141000.0	nM	PMID[504051]

☑ 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 NPC203972 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	296
0.1-0.2	1298
0.2-0.3	4028
0.3-0.4	12242
0.4-0.5	13077
0.5-0.6	10144
0.6-0.7	1487
0.7-0.8	116
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9553	High Similarity	NPC474077
0.8721	High Similarity	NPC278887
0.8547	High Similarity	NPC475962
0.8478	Intermediate Similarity	NPC28510
0.8021	Intermediate Similarity	NPC21425
0.7735	Intermediate Similarity	NPC52059
0.7735	Intermediate Similarity	NPC470069
0.7709	Intermediate Similarity	NPC243673
0.7709	Intermediate Similarity	NPC148468
0.7709	Intermediate Similarity	NPC263709
0.7709	Intermediate Similarity	NPC310403
0.7709	Intermediate Similarity	NPC63210
0.7709	Intermediate Similarity	NPC97380
0.7696	Intermediate Similarity	NPC217294
0.767	Intermediate Similarity	NPC96321
0.7668	Intermediate Similarity	NPC204970
0.7654	Intermediate Similarity	NPC153694
0.7654	Intermediate Similarity	NPC211525
0.7594	Intermediate Similarity	NPC311906
0.757	Intermediate Similarity	NPC475720
0.757	Intermediate Similarity	NPC474192
0.7542	Intermediate Similarity	NPC161827
0.7527	Intermediate Similarity	NPC293255
0.7527	Intermediate Similarity	NPC210415
0.7527	Intermediate Similarity	NPC181138
0.7527	Intermediate Similarity	NPC21752
0.7527	Intermediate Similarity	NPC298851
0.7527	Intermediate Similarity	NPC276993
0.7526	Intermediate Similarity	NPC98197
0.7488	Intermediate Similarity	NPC469928
0.7487	Intermediate Similarity	NPC138830
0.7474	Intermediate Similarity	NPC174629
0.7427	Intermediate Similarity	NPC472098
0.7426	Intermediate Similarity	NPC14339
0.7404	Intermediate Similarity	NPC234772
0.7385	Intermediate Similarity	NPC5630
0.7366	Intermediate Similarity	NPC168250
0.7364	Intermediate Similarity	NPC475816
0.7358	Intermediate Similarity	NPC473007
0.733	Intermediate Similarity	NPC471304
0.733	Intermediate Similarity	NPC269449
0.7299	Intermediate Similarity	NPC288110
0.7296	Intermediate Similarity	NPC473008
0.7294	Intermediate Similarity	NPC473105
0.7268	Intermediate Similarity	NPC478075
0.726	Intermediate Similarity	NPC119722
0.7251	Intermediate Similarity	NPC473041
0.7177	Intermediate Similarity	NPC127996
0.7171	Intermediate Similarity	NPC475147
0.7164	Intermediate Similarity	NPC272706
0.7158	Intermediate Similarity	NPC473297
0.7143	Intermediate Similarity	NPC473458
0.7136	Intermediate Similarity	NPC246140
0.7136	Intermediate Similarity	NPC473004
0.7136	Intermediate Similarity	NPC195787
0.713	Intermediate Similarity	NPC478080
0.7121	Intermediate Similarity	NPC474059
0.7103	Intermediate Similarity	NPC10653
0.7103	Intermediate Similarity	NPC318525
0.7103	Intermediate Similarity	NPC472099
0.7095	Intermediate Similarity	NPC159815
0.7093	Intermediate Similarity	NPC17437
0.7085	Intermediate Similarity	NPC22476
0.7075	Intermediate Similarity	NPC330009
0.7074	Intermediate Similarity	NPC70172
0.7067	Intermediate Similarity	NPC473540
0.7065	Intermediate Similarity	NPC230313
0.7064	Intermediate Similarity	NPC478078
0.7062	Intermediate Similarity	NPC39822
0.7059	Intermediate Similarity	NPC67904
0.7059	Intermediate Similarity	NPC472121
0.7059	Intermediate Similarity	NPC315498
0.7059	Intermediate Similarity	NPC230942
0.7059	Intermediate Similarity	NPC329793
0.7056	Intermediate Similarity	NPC108826
0.7044	Intermediate Similarity	NPC138615
0.7044	Intermediate Similarity	NPC218733
0.7044	Intermediate Similarity	NPC265642
0.7044	Intermediate Similarity	NPC132874
0.7042	Intermediate Similarity	NPC126556
0.7037	Intermediate Similarity	NPC472114
0.7037	Intermediate Similarity	NPC71539
0.7037	Intermediate Similarity	NPC250960
0.7037	Intermediate Similarity	NPC472115
0.7033	Intermediate Similarity	NPC475133
0.7033	Intermediate Similarity	NPC477160
0.7022	Intermediate Similarity	NPC477066
0.7013	Intermediate Similarity	NPC329982
0.7005	Intermediate Similarity	NPC87714
0.7	Intermediate Similarity	NPC476651
0.7	Intermediate Similarity	NPC203628
0.6995	Remote Similarity	NPC470001
0.6995	Remote Similarity	NPC470002
0.6991	Remote Similarity	NPC478081
0.6991	Remote Similarity	NPC477067
0.6991	Remote Similarity	NPC478082
0.6991	Remote Similarity	NPC128476
0.699	Remote Similarity	NPC473005
0.6986	Remote Similarity	NPC329329
0.6986	Remote Similarity	NPC317709
0.6981	Remote Similarity	NPC478074
0.697	Remote Similarity	NPC291759
0.695	Remote Similarity	NPC473569
0.6942	Remote Similarity	NPC469732
0.6941	Remote Similarity	NPC266994
0.6939	Remote Similarity	NPC270301
0.6938	Remote Similarity	NPC53344
0.6934	Remote Similarity	NPC10732
0.6927	Remote Similarity	NPC85482
0.6923	Remote Similarity	NPC477397
0.6919	Remote Similarity	NPC469460
0.6919	Remote Similarity	NPC133591
0.6916	Remote Similarity	NPC148183
0.6916	Remote Similarity	NPC152768
0.6915	Remote Similarity	NPC93653
0.6911	Remote Similarity	NPC469462
0.6909	Remote Similarity	NPC471513
0.6908	Remote Similarity	NPC1464
0.6905	Remote Similarity	NPC205926
0.69	Remote Similarity	NPC477186
0.6898	Remote Similarity	NPC222046
0.6897	Remote Similarity	NPC198401
0.6895	Remote Similarity	NPC19175
0.6895	Remote Similarity	NPC231924
0.6893	Remote Similarity	NPC127178
0.689	Remote Similarity	NPC472111
0.6887	Remote Similarity	NPC82541
0.6884	Remote Similarity	NPC282092
0.6884	Remote Similarity	NPC38823
0.6884	Remote Similarity	NPC207033
0.6878	Remote Similarity	NPC74216
0.6878	Remote Similarity	NPC17677
0.6878	Remote Similarity	NPC100863
0.6875	Remote Similarity	NPC473460
0.6869	Remote Similarity	NPC189661
0.6868	Remote Similarity	NPC472100
0.6865	Remote Similarity	NPC219383
0.6864	Remote Similarity	NPC476436
0.6863	Remote Similarity	NPC303214
0.686	Remote Similarity	NPC471489
0.686	Remote Similarity	NPC232600
0.6856	Remote Similarity	NPC81939
0.6842	Remote Similarity	NPC268077
0.6826	Remote Similarity	NPC475666
0.6825	Remote Similarity	NPC475910
0.6821	Remote Similarity	NPC8467
0.682	Remote Similarity	NPC37957
0.6814	Remote Similarity	NPC243626
0.6806	Remote Similarity	NPC195636
0.6784	Remote Similarity	NPC301501
0.6771	Remote Similarity	NPC127362
0.6769	Remote Similarity	NPC13367
0.6755	Remote Similarity	NPC10730
0.6755	Remote Similarity	NPC477156
0.6755	Remote Similarity	NPC477157
0.6755	Remote Similarity	NPC10875
0.6751	Remote Similarity	NPC472331
0.6751	Remote Similarity	NPC321211
0.6751	Remote Similarity	NPC126515
0.6751	Remote Similarity	NPC274002
0.6746	Remote Similarity	NPC52801
0.6733	Remote Similarity	NPC230098
0.673	Remote Similarity	NPC474145
0.673	Remote Similarity	NPC475841
0.6715	Remote Similarity	NPC23080
0.6715	Remote Similarity	NPC193906
0.6715	Remote Similarity	NPC71124
0.6714	Remote Similarity	NPC207971
0.6714	Remote Similarity	NPC471561
0.6712	Remote Similarity	NPC476069
0.6711	Remote Similarity	NPC476429
0.6711	Remote Similarity	NPC139373
0.67	Remote Similarity	NPC245741
0.6698	Remote Similarity	NPC264176
0.6698	Remote Similarity	NPC193238
0.6696	Remote Similarity	NPC470821
0.6696	Remote Similarity	NPC223242
0.6683	Remote Similarity	NPC280714
0.6682	Remote Similarity	NPC118832
0.6682	Remote Similarity	NPC329708
0.6682	Remote Similarity	NPC165349
0.6682	Remote Similarity	NPC47059
0.6682	Remote Similarity	NPC264166
0.6682	Remote Similarity	NPC274291
0.6682	Remote Similarity	NPC470484
0.6681	Remote Similarity	NPC469450
0.6667	Remote Similarity	NPC329567
0.6667	Remote Similarity	NPC330683
0.6667	Remote Similarity	NPC472209
0.6667	Remote Similarity	NPC21638
0.6667	Remote Similarity	NPC473006
0.6667	Remote Similarity	NPC153923
0.6652	Remote Similarity	NPC476220
0.6652	Remote Similarity	NPC160113
0.6651	Remote Similarity	NPC477161
0.665	Remote Similarity	NPC476441
0.665	Remote Similarity	NPC162694
0.665	Remote Similarity	NPC474745
0.665	Remote Similarity	NPC168153
0.6649	Remote Similarity	NPC474058

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 NPC203972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	546
0.2-0.3	768
0.3-0.4	1585
0.4-0.5	2730
0.5-0.6	2737
0.6-0.7	595
0.7-0.8	10
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
0.7363	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5811	Approved
0.7178	Intermediate Similarity	NPD6874	Approved
0.7108	Intermediate Similarity	NPD3416	Discontinued
0.7093	Intermediate Similarity	NPD8358	Approved
0.709	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3983	Phase 3
0.7074	Intermediate Similarity	NPD4796	Discontinued
0.7065	Intermediate Similarity	NPD5617	Suspended
0.7059	Intermediate Similarity	NPD19	Approved
0.7059	Intermediate Similarity	NPD1743	Approved
0.7059	Intermediate Similarity	NPD1742	Approved
0.7031	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2672	Discontinued
0.7026	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3453	Discontinued
0.6985	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5600	Discontinued
0.6957	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7820	Phase 3
0.6911	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD2821	Approved
0.6902	Remote Similarity	NPD3641	Approved
0.6902	Remote Similarity	NPD3639	Approved
0.6902	Remote Similarity	NPD3640	Phase 3
0.689	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5312	Approved
0.6872	Remote Similarity	NPD5313	Approved
0.6863	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.685	Remote Similarity	NPD4951	Discontinued
0.6832	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4082	Approved
0.6818	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6276	Discontinued
0.6789	Remote Similarity	NPD3437	Discontinued
0.6784	Remote Similarity	NPD7546	Discontinued
0.6782	Remote Similarity	NPD5928	Phase 1
0.6778	Remote Similarity	NPD3656	Approved
0.6773	Remote Similarity	NPD7542	Phase 3
0.6761	Remote Similarity	NPD5860	Discontinued
0.6758	Remote Similarity	NPD7556	Discontinued
0.6755	Remote Similarity	NPD2789	Approved
0.6754	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD8016	Phase 3
0.6749	Remote Similarity	NPD5871	Discontinued
0.6737	Remote Similarity	NPD5599	Discontinued
0.6737	Remote Similarity	NPD5967	Approved
0.6736	Remote Similarity	NPD2681	Approved
0.6736	Remote Similarity	NPD2680	Approved
0.6736	Remote Similarity	NPD6457	Approved
0.6729	Remote Similarity	NPD683	Approved
0.6711	Remote Similarity	NPD7796	Approved
0.6711	Remote Similarity	NPD7797	Approved
0.6701	Remote Similarity	NPD5670	Approved
0.6701	Remote Similarity	NPD3965	Phase 1
0.6701	Remote Similarity	NPD5183	Approved
0.6701	Remote Similarity	NPD5186	Approved
0.67	Remote Similarity	NPD2845	Phase 2
0.67	Remote Similarity	NPD2843	Phase 2
0.6699	Remote Similarity	NPD5582	Discontinued
0.6699	Remote Similarity	NPD5512	Phase 3
0.6698	Remote Similarity	NPD4596	Phase 1
0.6697	Remote Similarity	NPD3912	Discontinued
0.6697	Remote Similarity	NPD3354	Phase 2
0.6685	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6737	Phase 2
0.6684	Remote Similarity	NPD6738	Phase 2
0.6684	Remote Similarity	NPD6037	Discontinued
0.6684	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4035	Approved
0.6682	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4122	Approved
0.6682	Remote Similarity	NPD4038	Approved
0.6682	Remote Similarity	NPD4034	Approved
0.6682	Remote Similarity	NPD4033	Approved
0.6682	Remote Similarity	NPD31	Approved
0.6682	Remote Similarity	NPD4037	Approved
0.6682	Remote Similarity	NPD32	Approved
0.6682	Remote Similarity	NPD4039	Approved
0.6682	Remote Similarity	NPD4036	Approved
0.6667	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2906	Approved
0.6667	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5557	Phase 1
0.6667	Remote Similarity	NPD2907	Approved
0.6667	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7479	Phase 2
0.6651	Remote Similarity	NPD6905	Phase 2
0.6651	Remote Similarity	NPD4493	Discontinued
0.665	Remote Similarity	NPD3909	Discontinued
0.665	Remote Similarity	NPD3398	Discontinued
0.665	Remote Similarity	NPD4418	Discontinued
0.6649	Remote Similarity	NPD6107	Approved
0.6633	Remote Similarity	NPD6184	Discontinued
0.6633	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6346	Approved
0.6622	Remote Similarity	NPD6199	Discontinued
0.662	Remote Similarity	NPD7453	Approved
0.662	Remote Similarity	NPD7452	Approved
0.662	Remote Similarity	NPD5429	Discontinued
0.6619	Remote Similarity	NPD6238	Discontinued
0.6617	Remote Similarity	NPD7280	Phase 3
0.6617	Remote Similarity	NPD7281	Phase 3
0.6616	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5488	Discontinued
0.6606	Remote Similarity	NPD7805	Phase 3
0.6604	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7565	Approved
0.6599	Remote Similarity	NPD3446	Phase 1
0.6598	Remote Similarity	NPD8363	Approved
0.6598	Remote Similarity	NPD8364	Approved
0.6597	Remote Similarity	NPD7599	Phase 2
0.6596	Remote Similarity	NPD8101	Phase 3
0.6596	Remote Similarity	NPD4003	Phase 3
0.6587	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6519	Phase 2
0.6567	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD2802	Phase 3
0.6561	Remote Similarity	NPD6357	Discontinued
0.656	Remote Similarity	NPD4897	Phase 2
0.656	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5071	Phase 2
0.6552	Remote Similarity	NPD3154	Approved
0.6552	Remote Similarity	NPD3153	Approved
0.655	Remote Similarity	NPD6297	Approved
0.655	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6894	Phase 1
0.6545	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7395	Discontinued
0.6544	Remote Similarity	NPD4492	Approved
0.6544	Remote Similarity	NPD4494	Approved
0.6544	Remote Similarity	NPD7069	Discontinued
0.6544	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7427	Discontinued
0.6542	Remote Similarity	NPD7222	Phase 2
0.6541	Remote Similarity	NPD3692	Discontinued
0.6535	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7315	Approved
0.6531	Remote Similarity	NPD7608	Discontinued
0.6531	Remote Similarity	NPD6747	Phase 1
0.6526	Remote Similarity	NPD6502	Phase 2
0.6522	Remote Similarity	NPD5610	Approved
0.6517	Remote Similarity	NPD3037	Phase 1
0.6517	Remote Similarity	NPD4203	Approved
0.6517	Remote Similarity	NPD4204	Approved
0.6516	Remote Similarity	NPD3258	Approved
0.6514	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3472	Approved
0.6512	Remote Similarity	NPD4022	Approved
0.6512	Remote Similarity	NPD4154	Approved
0.6504	Remote Similarity	NPD5014	Discontinued
0.65	Remote Similarity	NPD5190	Phase 2
0.65	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD5416	Discontinued
0.6498	Remote Similarity	NPD1945	Phase 1
0.6497	Remote Similarity	NPD4083	Discontinued
0.6495	Remote Similarity	NPD5530	Phase 1
0.6492	Remote Similarity	NPD2366	Approved
0.6489	Remote Similarity	NPD7186	Phase 3
0.6488	Remote Similarity	NPD2792	Approved
0.6488	Remote Similarity	NPD8025	Phase 2
0.6488	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7126	Discontinued
0.6477	Remote Similarity	NPD6063	Approved
0.6476	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD3963	Phase 1
0.6473	Remote Similarity	NPD4740	Approved
0.6471	Remote Similarity	NPD2114	Discontinued
0.6468	Remote Similarity	NPD2168	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD8100	Phase 3
0.6468	Remote Similarity	NPD7301	Phase 3
0.6468	Remote Similarity	NPD2167	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7560	Approved
0.6466	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6296	Discontinued
0.6465	Remote Similarity	NPD3952	Approved
0.6465	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD3951	Phase 3
0.6462	Remote Similarity	NPD2190	Approved
0.6456	Remote Similarity	NPD4499	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