NPASS Compound

Structure

NPC14994 OpenBabel07101719252D 30 35 0 0 1 0 0 0 0 0999 V2000 -2.5370 -1.8762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7767 2.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3586 -4.9198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5853 -2.1834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9856 -0.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3922 -1.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1725 -0.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9856 -1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5461 -0.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9463 0.3232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8884 1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5692 -2.2783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7618 1.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2003 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7659 -1.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1725 -1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8734 0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7319 -0.0259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8855 -2.1033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 -1.0258 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3197 -3.5339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 -0.9999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8435 -1.5128 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9705 -1.2946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6284 -2.4341 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -2.6202 1.4610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4804 -4.1337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2392 -3.9269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 -0.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 13 1 0 0 0 0 3 29 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 10 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 27 2 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 1 0 0 0 18 20 1 0 0 0 0 18 30 1 1 0 0 0 19 24 1 0 0 0 0 19 25 1 0 0 0 0 20 23 1 1 0 0 0 20 30 1 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 22 23 1 6 0 0 0 22 24 1 0 0 0 0 22 26 1 0 0 0 0 23 4 1 1 0 0 0 24 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.2
Volume:	413.657
LogP:	2.032
LogD:	2.018
LogS:	-3.875
# Rotatable Bonds:	5
TPSA:	71.5
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.566
Synthetic Accessibility Score:	5.489
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.263
MDCK Permeability:	2.059558391920291e-05
Pgp-inhibitor:	0.085
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.865
Plasma Protein Binding (PPB):	41.02602767944336%
Volume Distribution (VD):	1.455
Pgp-substrate:	65.29669189453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.389
CYP2C19-inhibitor:	0.236
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.178
CYP2C9-substrate:	0.107
CYP2D6-inhibitor:	0.36
CYP2D6-substrate:	0.845
CYP3A4-inhibitor:	0.731
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	7.065
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.291
Human Hepatotoxicity (H-HT):	0.814
Drug-inuced Liver Injury (DILI):	0.304
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.466
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.158
Carcinogencity:	0.439
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC14994

Natural Product ID:	NPC14994
*Common Name:**	Melodinine S
IUPAC Name:	n.a.
Synonyms:	Melodinine S
Standard InCHIKey:	XWFITHBMHMJLJH-VAUGZCKVSA-N
Standard InCHI:	InChI=1S/C24H28N2O4/c1-4-23-12-14(21(28)29-3)19-24(15-7-5-6-8-16(15)25-19)9-10-26(22(23)24)17(11-13(2)27)18-20(23)30-18/h5-8,17-18,20,22,25H,4,9-12H2,1-3H3/t17-,18+,20+,22+,23-,24+/m1/s1
SMILES:	COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@@](C1)(CC)[C@H]1O[C@H]1[C@H](N2CC4)CC(=O)C)cccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011509
PubChem CID:	57333163
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002755] Aspidospermatan-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
NPO33137	melodinus suaveolens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22260257]
NPO33137	melodinus suaveolens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24274642]

☑ 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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4800.0	nM	PMID[484880]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	11200.0	nM	PMID[484880]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	15200.0	nM	PMID[484880]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7000.0	nM	PMID[484880]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	13500.0	nM	PMID[484880]

☑ 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 NPC14994 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	266
0.1-0.2	1131
0.2-0.3	3569
0.3-0.4	13683
0.4-0.5	18417
0.5-0.6	4701
0.6-0.7	744
0.7-0.8	155
0.8-0.85	14
0.85-0.9	12
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC159963
0.9477	High Similarity	NPC25401
0.9226	High Similarity	NPC264482
0.9226	High Similarity	NPC203202
0.9172	High Similarity	NPC186669
0.9017	High Similarity	NPC97584
0.9006	High Similarity	NPC6974
0.8895	High Similarity	NPC218594
0.8895	High Similarity	NPC99043
0.8735	High Similarity	NPC61013
0.8706	High Similarity	NPC224970
0.8706	High Similarity	NPC223595
0.8706	High Similarity	NPC167724
0.869	High Similarity	NPC293458
0.8631	High Similarity	NPC248117
0.8571	High Similarity	NPC193410
0.8512	High Similarity	NPC123241
0.84	Intermediate Similarity	NPC329338
0.84	Intermediate Similarity	NPC469726
0.8316	Intermediate Similarity	NPC77777
0.8173	Intermediate Similarity	NPC195636
0.814	Intermediate Similarity	NPC36495
0.8063	Intermediate Similarity	NPC1464
0.805	Intermediate Similarity	NPC476069
0.8046	Intermediate Similarity	NPC99632
0.8046	Intermediate Similarity	NPC282339
0.8031	Intermediate Similarity	NPC246140
0.8031	Intermediate Similarity	NPC195787
0.7979	Intermediate Similarity	NPC87714
0.7946	Intermediate Similarity	NPC181928
0.7892	Intermediate Similarity	NPC19175
0.7861	Intermediate Similarity	NPC473298
0.7809	Intermediate Similarity	NPC214960
0.7809	Intermediate Similarity	NPC279527
0.78	Intermediate Similarity	NPC189661
0.7789	Intermediate Similarity	NPC34717
0.7784	Intermediate Similarity	NPC225319
0.7766	Intermediate Similarity	NPC5630
0.776	Intermediate Similarity	NPC218733
0.776	Intermediate Similarity	NPC132874
0.776	Intermediate Similarity	NPC265642
0.776	Intermediate Similarity	NPC138615
0.7751	Intermediate Similarity	NPC139373
0.774	Intermediate Similarity	NPC223242
0.7725	Intermediate Similarity	NPC22476
0.7725	Intermediate Similarity	NPC203628
0.7708	Intermediate Similarity	NPC90967
0.767	Intermediate Similarity	NPC113946
0.7637	Intermediate Similarity	NPC214626
0.7637	Intermediate Similarity	NPC210415
0.7637	Intermediate Similarity	NPC21752
0.7637	Intermediate Similarity	NPC181138
0.7637	Intermediate Similarity	NPC276993
0.7637	Intermediate Similarity	NPC139085
0.7637	Intermediate Similarity	NPC293255
0.7637	Intermediate Similarity	NPC251212
0.7637	Intermediate Similarity	NPC298851
0.7584	Intermediate Similarity	NPC309531
0.7584	Intermediate Similarity	NPC472102
0.7584	Intermediate Similarity	NPC474058
0.7573	Intermediate Similarity	NPC128476
0.757	Intermediate Similarity	NPC301501
0.7565	Intermediate Similarity	NPC303214
0.7559	Intermediate Similarity	NPC291173
0.7553	Intermediate Similarity	NPC52262
0.7551	Intermediate Similarity	NPC471512
0.7551	Intermediate Similarity	NPC232600
0.7541	Intermediate Similarity	NPC285622
0.7523	Intermediate Similarity	NPC131977
0.7514	Intermediate Similarity	NPC260075
0.7487	Intermediate Similarity	NPC105055
0.7487	Intermediate Similarity	NPC22689
0.7465	Intermediate Similarity	NPC469451
0.7454	Intermediate Similarity	NPC469450
0.7446	Intermediate Similarity	NPC96901
0.7444	Intermediate Similarity	NPC472101
0.7444	Intermediate Similarity	NPC472120
0.7437	Intermediate Similarity	NPC475147
0.7397	Intermediate Similarity	NPC329932
0.7385	Intermediate Similarity	NPC469722
0.7385	Intermediate Similarity	NPC469452
0.7376	Intermediate Similarity	NPC475133
0.7363	Intermediate Similarity	NPC52059
0.7363	Intermediate Similarity	NPC470069
0.7363	Intermediate Similarity	NPC472106
0.736	Intermediate Similarity	NPC161827
0.7351	Intermediate Similarity	NPC476425
0.7348	Intermediate Similarity	NPC472117
0.7337	Intermediate Similarity	NPC472118
0.7333	Intermediate Similarity	NPC221687
0.7317	Intermediate Similarity	NPC472291
0.731	Intermediate Similarity	NPC100863
0.7303	Intermediate Similarity	NPC478076
0.7287	Intermediate Similarity	NPC321211
0.7286	Intermediate Similarity	NPC469732
0.7277	Intermediate Similarity	NPC322621
0.7258	Intermediate Similarity	NPC177261
0.7255	Intermediate Similarity	NPC269449
0.7253	Intermediate Similarity	NPC286871
0.7248	Intermediate Similarity	NPC151171
0.7238	Intermediate Similarity	NPC63210
0.7238	Intermediate Similarity	NPC97380
0.7238	Intermediate Similarity	NPC243673
0.7238	Intermediate Similarity	NPC148468
0.7238	Intermediate Similarity	NPC310403
0.7238	Intermediate Similarity	NPC263709
0.7217	Intermediate Similarity	NPC231924
0.7191	Intermediate Similarity	NPC314223
0.7191	Intermediate Similarity	NPC243756
0.7188	Intermediate Similarity	NPC472209
0.7188	Intermediate Similarity	NPC49184
0.7184	Intermediate Similarity	NPC119722
0.7163	Intermediate Similarity	NPC234772
0.7159	Intermediate Similarity	NPC264589
0.7158	Intermediate Similarity	NPC472121
0.7158	Intermediate Similarity	NPC176983
0.7156	Intermediate Similarity	NPC154922
0.7143	Intermediate Similarity	NPC476326
0.7135	Intermediate Similarity	NPC473329
0.7135	Intermediate Similarity	NPC472115
0.7135	Intermediate Similarity	NPC472114
0.7121	Intermediate Similarity	NPC473375
0.7121	Intermediate Similarity	NPC97100
0.712	Intermediate Similarity	NPC475962
0.712	Intermediate Similarity	NPC313757
0.7105	Intermediate Similarity	NPC475094
0.7104	Intermediate Similarity	NPC201424
0.7095	Intermediate Similarity	NPC475763
0.709	Intermediate Similarity	NPC476441
0.7088	Intermediate Similarity	NPC153694
0.7088	Intermediate Similarity	NPC211525
0.7085	Intermediate Similarity	NPC162440
0.707	Intermediate Similarity	NPC473458
0.7065	Intermediate Similarity	NPC475489
0.7056	Intermediate Similarity	NPC115588
0.7033	Intermediate Similarity	NPC36836
0.7033	Intermediate Similarity	NPC29285
0.7033	Intermediate Similarity	NPC63370
0.7019	Intermediate Similarity	NPC127996
0.701	Intermediate Similarity	NPC259626
0.701	Intermediate Similarity	NPC329833
0.7005	Intermediate Similarity	NPC477397
0.6996	Remote Similarity	NPC113455
0.6995	Remote Similarity	NPC477159
0.6991	Remote Similarity	NPC471513
0.699	Remote Similarity	NPC285192
0.698	Remote Similarity	NPC138830
0.698	Remote Similarity	NPC214428
0.698	Remote Similarity	NPC294909
0.698	Remote Similarity	NPC199851
0.698	Remote Similarity	NPC254240
0.698	Remote Similarity	NPC312870
0.698	Remote Similarity	NPC128265
0.6977	Remote Similarity	NPC477394
0.6976	Remote Similarity	NPC277350
0.6974	Remote Similarity	NPC473615
0.6967	Remote Similarity	NPC471197
0.6967	Remote Similarity	NPC126556
0.6961	Remote Similarity	NPC122106
0.6959	Remote Similarity	NPC2933
0.695	Remote Similarity	NPC245916
0.6943	Remote Similarity	NPC476428
0.6942	Remote Similarity	NPC478075
0.694	Remote Similarity	NPC469536
0.6939	Remote Similarity	NPC229484
0.6934	Remote Similarity	NPC471198
0.6911	Remote Similarity	NPC129624
0.6907	Remote Similarity	NPC256288
0.6904	Remote Similarity	NPC284706
0.6904	Remote Similarity	NPC316405
0.6904	Remote Similarity	NPC292675
0.6903	Remote Similarity	NPC120239
0.6901	Remote Similarity	NPC288110
0.6897	Remote Similarity	NPC67904
0.6891	Remote Similarity	NPC11149
0.6887	Remote Similarity	NPC473837
0.6882	Remote Similarity	NPC85651
0.6878	Remote Similarity	NPC160113
0.6878	Remote Similarity	NPC476220
0.6854	Remote Similarity	NPC190945
0.6853	Remote Similarity	NPC21425
0.6837	Remote Similarity	NPC469460
0.6829	Remote Similarity	NPC162730
0.682	Remote Similarity	NPC122886
0.6818	Remote Similarity	NPC130251
0.6816	Remote Similarity	NPC198205
0.6816	Remote Similarity	NPC21483
0.6816	Remote Similarity	NPC243626
0.6813	Remote Similarity	NPC154602
0.6812	Remote Similarity	NPC477161
0.6798	Remote Similarity	NPC112752
0.6798	Remote Similarity	NPC311054
0.6791	Remote Similarity	NPC469741
0.6789	Remote Similarity	NPC476436
0.6789	Remote Similarity	NPC469915
0.6774	Remote Similarity	NPC471122
0.6772	Remote Similarity	NPC278887
0.6771	Remote Similarity	NPC13367
0.677	Remote Similarity	NPC477395
0.6766	Remote Similarity	NPC470485

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 NPC14994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	481
0.2-0.3	701
0.3-0.4	1494
0.4-0.5	3791
0.5-0.6	2241
0.6-0.7	270
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
0.7268	Intermediate Similarity	NPD7035	Approved
0.7268	Intermediate Similarity	NPD7036	Phase 3
0.7172	Intermediate Similarity	NPD3828	Approved
0.7119	Intermediate Similarity	NPD1801	Approved
0.7119	Intermediate Similarity	NPD1802	Approved
0.7105	Intermediate Similarity	NPD2869	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6571	Approved
0.7033	Intermediate Similarity	NPD6570	Approved
0.698	Remote Similarity	NPD4500	Approved
0.698	Remote Similarity	NPD4501	Approved
0.698	Remote Similarity	NPD6805	Discontinued
0.6966	Remote Similarity	NPD4041	Approved
0.6961	Remote Similarity	NPD3399	Approved
0.6957	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7940	Phase 3
0.6854	Remote Similarity	NPD2435	Approved
0.6851	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7244	Discontinued
0.6821	Remote Similarity	NPD5182	Approved
0.6821	Remote Similarity	NPD5185	Approved
0.6821	Remote Similarity	NPD5184	Approved
0.6796	Remote Similarity	NPD7205	Discontinued
0.6796	Remote Similarity	NPD7528	Approved
0.6789	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD3422	Phase 3
0.6771	Remote Similarity	NPD3423	Phase 2
0.6769	Remote Similarity	NPD3471	Approved
0.6769	Remote Similarity	NPD3470	Approved
0.6761	Remote Similarity	NPD1109	Approved
0.6761	Remote Similarity	NPD1110	Approved
0.6761	Remote Similarity	NPD3170	Approved
0.6755	Remote Similarity	NPD8008	Approved
0.6755	Remote Similarity	NPD8007	Approved
0.6754	Remote Similarity	NPD2432	Approved
0.6754	Remote Similarity	NPD2431	Approved
0.6753	Remote Similarity	NPD7775	Approved
0.6746	Remote Similarity	NPD4082	Approved
0.6744	Remote Similarity	NPD6770	Approved
0.6737	Remote Similarity	NPD2037	Approved
0.6735	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8281	Discontinued
0.673	Remote Similarity	NPD4493	Discontinued
0.6729	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5997	Discontinued
0.6718	Remote Similarity	NPD4330	Approved
0.6718	Remote Similarity	NPD4329	Approved
0.6703	Remote Similarity	NPD5942	Approved
0.6703	Remote Similarity	NPD5941	Approved
0.6699	Remote Similarity	NPD4596	Phase 1
0.6698	Remote Similarity	NPD4494	Approved
0.6698	Remote Similarity	NPD4492	Approved
0.6683	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7881	Approved
0.6667	Remote Similarity	NPD7487	Discontinued
0.6667	Remote Similarity	NPD5504	Discontinued
0.6649	Remote Similarity	NPD2455	Approved
0.6649	Remote Similarity	NPD2454	Approved
0.663	Remote Similarity	NPD7606	Phase 3
0.6617	Remote Similarity	NPD4499	Approved
0.6615	Remote Similarity	NPD3792	Approved
0.661	Remote Similarity	NPD2670	Approved
0.6598	Remote Similarity	NPD5466	Approved
0.6595	Remote Similarity	NPD2948	Discontinued
0.6593	Remote Similarity	NPD4607	Approved
0.6589	Remote Similarity	NPD4455	Discontinued
0.6588	Remote Similarity	NPD4022	Approved
0.6588	Remote Similarity	NPD2509	Approved
0.6588	Remote Similarity	NPD2510	Approved
0.6588	Remote Similarity	NPD3472	Approved
0.6564	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2404	Discontinued
0.6561	Remote Similarity	NPD7600	Phase 2
0.6561	Remote Similarity	NPD2506	Approved
0.6559	Remote Similarity	NPD4121	Phase 3
0.6559	Remote Similarity	NPD4120	Approved
0.6557	Remote Similarity	NPD7478	Approved
0.6557	Remote Similarity	NPD3352	Approved
0.6556	Remote Similarity	NPD2923	Approved
0.6545	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3888	Discontinued
0.6538	Remote Similarity	NPD6238	Discontinued
0.6538	Remote Similarity	NPD6017	Discontinued
0.6538	Remote Similarity	NPD6185	Discontinued
0.6532	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5183	Approved
0.6528	Remote Similarity	NPD5186	Approved
0.6526	Remote Similarity	NPD3893	Discontinued
0.6526	Remote Similarity	NPD3372	Discontinued
0.6524	Remote Similarity	NPD5742	Approved
0.6524	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5743	Approved
0.6524	Remote Similarity	NPD5741	Approved
0.6513	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3782	Discontinued
0.6495	Remote Similarity	NPD1945	Phase 1
0.6495	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1663	Discontinued
0.6486	Remote Similarity	NPD4513	Discontinued
0.6486	Remote Similarity	NPD7186	Phase 3
0.6484	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD4506	Discontinued
0.6477	Remote Similarity	NPD3468	Approved
0.6467	Remote Similarity	NPD6758	Approved
0.6462	Remote Similarity	NPD3377	Discontinued
0.646	Remote Similarity	NPD6625	Approved
0.6455	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.645	Remote Similarity	NPD3436	Approved
0.6445	Remote Similarity	NPD3947	Discontinued
0.6444	Remote Similarity	NPD7688	Phase 1
0.6432	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2567	Approved
0.6425	Remote Similarity	NPD2569	Approved
0.6425	Remote Similarity	NPD5318	Discontinued
0.6422	Remote Similarity	NPD5042	Phase 1
0.6422	Remote Similarity	NPD6659	Phase 2
0.6421	Remote Similarity	NPD2427	Approved
0.6421	Remote Similarity	NPD7599	Phase 2
0.6406	Remote Similarity	NPD3790	Phase 2
0.6404	Remote Similarity	NPD3006	Discontinued
0.6402	Remote Similarity	NPD7105	Phase 1
0.64	Remote Similarity	NPD6199	Discontinued
0.6398	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD2790	Discontinued
0.6382	Remote Similarity	NPD6879	Phase 2
0.6382	Remote Similarity	NPD6878	Phase 2
0.6372	Remote Similarity	NPD5860	Discontinued
0.6364	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD2906	Approved
0.6355	Remote Similarity	NPD2907	Approved
0.6355	Remote Similarity	NPD4859	Phase 1
0.635	Remote Similarity	NPD3435	Discontinued
0.6341	Remote Similarity	NPD4370	Phase 3
0.6341	Remote Similarity	NPD3884	Discontinued
0.6339	Remote Similarity	NPD5024	Approved
0.6335	Remote Similarity	NPD3437	Discontinued
0.6333	Remote Similarity	NPD4600	Approved
0.6333	Remote Similarity	NPD4601	Approved
0.6329	Remote Similarity	NPD4602	Approved
0.6321	Remote Similarity	NPD6176	Phase 1
0.6319	Remote Similarity	NPD3625	Discontinued
0.6318	Remote Similarity	NPD7962	Phase 2
0.6308	Remote Similarity	NPD2680	Approved
0.6308	Remote Similarity	NPD6518	Discontinued
0.6308	Remote Similarity	NPD2681	Approved
0.6304	Remote Similarity	NPD5918	Discontinued
0.6301	Remote Similarity	NPD3389	Approved
0.6301	Remote Similarity	NPD3393	Approved
0.6301	Remote Similarity	NPD3394	Approved
0.6296	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD7854	Phase 2
0.6293	Remote Similarity	NPD5928	Phase 1
0.6293	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD1527	Phase 2
0.6292	Remote Similarity	NPD2574	Discontinued
0.6292	Remote Similarity	NPD2566	Approved
0.6292	Remote Similarity	NPD3089	Approved
0.6292	Remote Similarity	NPD2570	Approved
0.6292	Remote Similarity	NPD3088	Approved
0.6292	Remote Similarity	NPD2573	Approved
0.6292	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD2571	Approved
0.6292	Remote Similarity	NPD4746	Phase 3
0.6292	Remote Similarity	NPD3087	Approved
0.6292	Remote Similarity	NPD3615	Approved
0.6292	Remote Similarity	NPD3614	Approved
0.6292	Remote Similarity	NPD3090	Approved
0.6292	Remote Similarity	NPD3616	Approved
0.6292	Remote Similarity	NPD4745	Approved
0.6289	Remote Similarity	NPD5430	Discontinued
0.6287	Remote Similarity	NPD4412	Phase 2
0.6286	Remote Similarity	NPD5993	Phase 1
0.6281	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8399	Phase 1
0.6279	Remote Similarity	NPD8423	Phase 2
0.6277	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6891	Phase 2
0.6274	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD8326	Phase 3
0.6273	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD8325	Phase 3
0.627	Remote Similarity	NPD7295	Approved
0.627	Remote Similarity	NPD6622	Phase 1
0.6268	Remote Similarity	NPD5003	Discontinued
0.6263	Remote Similarity	NPD1092	Approved
0.6263	Remote Similarity	NPD1093	Approved
0.6261	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4888	Discontinued
0.6256	Remote Similarity	NPD6557	Phase 2
0.6256	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD6519	Phase 2
0.625	Remote Similarity	NPD7560	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