NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	247.16
Volume:	268.915
LogP:	3.007
LogD:	2.595
LogS:	-2.846
# Rotatable Bonds:	2
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	4.466
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.639
MDCK Permeability:	1.2942483408551197e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.393
Plasma Protein Binding (PPB):	87.60636138916016%
Volume Distribution (VD):	0.89
Pgp-substrate:	13.803071022033691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.357
CYP1A2-substrate:	0.845
CYP2C19-inhibitor:	0.245
CYP2C19-substrate:	0.74
CYP2C9-inhibitor:	0.326
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.556
CYP3A4-inhibitor:	0.77
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	4.121
Half-life (T1/2):	0.552

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.81
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.815
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.652
Carcinogencity:	0.259
Eye Corrosion:	0.014
Eye Irritation:	0.512
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC473057

Natural Product ID:	NPC473057
*Common Name:**	SWIJWROLKBJDFO-YIVACMHISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SWIJWROLKBJDFO-YIVACMHISA-N
Standard InCHI:	InChI=1S/C15H21NO2/c1-4-11-8-9(2)7-10(3)13(11)14-12(17)5-6-16-15(14)18/h4-6,9-11,13H,1,7-8H2,2-3H3,(H2,16,17,18)/t9-,10+,11-,13?/m1/s1
SMILES:	CC1CC(C(C(C1)C=C)C2=C(C=CNC2=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608617
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0002224] Hydropyridines [CHEMONTID:0001160] Pyridinones

*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
NPO4374	Tolypocladium cylindrosporum	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26356746]

☑ 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	4

Activity Type	# Activity
Cell Line	4

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[511215]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[511215]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	40000.0	nM	PMID[511215]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	40000.0	nM	PMID[511215]

☑ 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 NPC473057 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	390
0.1-0.2	1932
0.2-0.3	12548
0.3-0.4	8239
0.4-0.5	13993
0.5-0.6	4118
0.6-0.7	1319
0.7-0.8	141
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9108	High Similarity	NPC108469
0.8605	High Similarity	NPC289786
0.8571	High Similarity	NPC471178
0.8447	Intermediate Similarity	NPC59779
0.8447	Intermediate Similarity	NPC124542
0.8447	Intermediate Similarity	NPC471177
0.8395	Intermediate Similarity	NPC97367
0.8192	Intermediate Similarity	NPC473053
0.8129	Intermediate Similarity	NPC245657
0.8065	Intermediate Similarity	NPC280853
0.8023	Intermediate Similarity	NPC56170
0.8013	Intermediate Similarity	NPC285016
0.8	Intermediate Similarity	NPC471596
0.7944	Intermediate Similarity	NPC224928
0.7919	Intermediate Similarity	NPC151489
0.7892	Intermediate Similarity	NPC315214
0.7892	Intermediate Similarity	NPC47298
0.7885	Intermediate Similarity	NPC471594
0.7882	Intermediate Similarity	NPC471294
0.7862	Intermediate Similarity	NPC471598
0.7857	Intermediate Similarity	NPC98187
0.7844	Intermediate Similarity	NPC159319
0.7844	Intermediate Similarity	NPC32028
0.7831	Intermediate Similarity	NPC25899
0.7815	Intermediate Similarity	NPC212125
0.7809	Intermediate Similarity	NPC3715
0.7778	Intermediate Similarity	NPC259545
0.7765	Intermediate Similarity	NPC473764
0.7765	Intermediate Similarity	NPC314940
0.7764	Intermediate Similarity	NPC161292
0.7714	Intermediate Similarity	NPC470474
0.7711	Intermediate Similarity	NPC132680
0.7711	Intermediate Similarity	NPC269919
0.7701	Intermediate Similarity	NPC232340
0.7679	Intermediate Similarity	NPC48192
0.7665	Intermediate Similarity	NPC84508
0.7661	Intermediate Similarity	NPC126481
0.7644	Intermediate Similarity	NPC283152
0.7637	Intermediate Similarity	NPC146724
0.7625	Intermediate Similarity	NPC60553
0.76	Intermediate Similarity	NPC164340
0.7598	Intermediate Similarity	NPC46580
0.759	Intermediate Similarity	NPC63562
0.7586	Intermediate Similarity	NPC288943
0.7584	Intermediate Similarity	NPC314002
0.7582	Intermediate Similarity	NPC471313
0.7582	Intermediate Similarity	NPC165370
0.7582	Intermediate Similarity	NPC306397
0.7582	Intermediate Similarity	NPC471311
0.7576	Intermediate Similarity	NPC153769
0.7574	Intermediate Similarity	NPC177404
0.7571	Intermediate Similarity	NPC133306
0.7562	Intermediate Similarity	NPC318935
0.7542	Intermediate Similarity	NPC171171
0.7532	Intermediate Similarity	NPC29702
0.7531	Intermediate Similarity	NPC471323
0.7529	Intermediate Similarity	NPC263439
0.7528	Intermediate Similarity	NPC204717
0.7528	Intermediate Similarity	NPC320394
0.7514	Intermediate Similarity	NPC252590
0.75	Intermediate Similarity	NPC174421
0.7487	Intermediate Similarity	NPC155792
0.7486	Intermediate Similarity	NPC329541
0.7472	Intermediate Similarity	NPC220765
0.7459	Intermediate Similarity	NPC44354
0.7443	Intermediate Similarity	NPC96890
0.7432	Intermediate Similarity	NPC99666
0.7432	Intermediate Similarity	NPC114335
0.7432	Intermediate Similarity	NPC280964
0.7432	Intermediate Similarity	NPC141915
0.743	Intermediate Similarity	NPC62069
0.7412	Intermediate Similarity	NPC63338
0.7412	Intermediate Similarity	NPC322976
0.7412	Intermediate Similarity	NPC324203
0.7389	Intermediate Similarity	NPC256893
0.7363	Intermediate Similarity	NPC183805
0.736	Intermediate Similarity	NPC271792
0.7353	Intermediate Similarity	NPC113812
0.7345	Intermediate Similarity	NPC184964
0.7337	Intermediate Similarity	NPC133140
0.7337	Intermediate Similarity	NPC195268
0.7337	Intermediate Similarity	NPC324149
0.7333	Intermediate Similarity	NPC220523
0.7326	Intermediate Similarity	NPC211187
0.7321	Intermediate Similarity	NPC26872
0.7316	Intermediate Similarity	NPC53144
0.7316	Intermediate Similarity	NPC200836
0.7312	Intermediate Similarity	NPC242209
0.7308	Intermediate Similarity	NPC66083
0.7299	Intermediate Similarity	NPC44161
0.7293	Intermediate Similarity	NPC42591
0.7288	Intermediate Similarity	NPC203754
0.7288	Intermediate Similarity	NPC150048
0.7287	Intermediate Similarity	NPC476167
0.7282	Intermediate Similarity	NPC202605
0.7282	Intermediate Similarity	NPC112206
0.7278	Intermediate Similarity	NPC324611
0.7273	Intermediate Similarity	NPC90229
0.7273	Intermediate Similarity	NPC473822
0.7268	Intermediate Similarity	NPC32771
0.7254	Intermediate Similarity	NPC477111
0.7234	Intermediate Similarity	NPC192315
0.7219	Intermediate Similarity	NPC91958
0.7215	Intermediate Similarity	NPC315320
0.7214	Intermediate Similarity	NPC122463
0.7209	Intermediate Similarity	NPC131718
0.7207	Intermediate Similarity	NPC72980
0.7204	Intermediate Similarity	NPC45850
0.7204	Intermediate Similarity	NPC106937
0.7198	Intermediate Similarity	NPC295158
0.7188	Intermediate Similarity	NPC329708
0.7188	Intermediate Similarity	NPC165349
0.7188	Intermediate Similarity	NPC118832
0.7188	Intermediate Similarity	NPC47059
0.7188	Intermediate Similarity	NPC475070
0.7188	Intermediate Similarity	NPC264166
0.7188	Intermediate Similarity	NPC274291
0.7184	Intermediate Similarity	NPC477975
0.7181	Intermediate Similarity	NPC156704
0.7181	Intermediate Similarity	NPC77555
0.7175	Intermediate Similarity	NPC313791
0.7174	Intermediate Similarity	NPC472289
0.7173	Intermediate Similarity	NPC211813
0.7167	Intermediate Similarity	NPC471997
0.7165	Intermediate Similarity	NPC18348
0.716	Intermediate Similarity	NPC471312
0.7159	Intermediate Similarity	NPC256828
0.7158	Intermediate Similarity	NPC61350
0.7152	Intermediate Similarity	NPC470404
0.7152	Intermediate Similarity	NPC470394
0.7152	Intermediate Similarity	NPC470403
0.7127	Intermediate Similarity	NPC219963
0.7127	Intermediate Similarity	NPC266551
0.7127	Intermediate Similarity	NPC161887
0.7126	Intermediate Similarity	NPC474217
0.7126	Intermediate Similarity	NPC102423
0.7119	Intermediate Similarity	NPC14651
0.7119	Intermediate Similarity	NPC121658
0.7114	Intermediate Similarity	NPC174049
0.7112	Intermediate Similarity	NPC307963
0.7112	Intermediate Similarity	NPC103230
0.7111	Intermediate Similarity	NPC42979
0.7105	Intermediate Similarity	NPC143603
0.7098	Intermediate Similarity	NPC16452
0.7098	Intermediate Similarity	NPC36229
0.7098	Intermediate Similarity	NPC470500
0.7098	Intermediate Similarity	NPC476581
0.7097	Intermediate Similarity	NPC290094
0.7097	Intermediate Similarity	NPC469390
0.7095	Intermediate Similarity	NPC224764
0.7093	Intermediate Similarity	NPC129721
0.7093	Intermediate Similarity	NPC26850
0.7092	Intermediate Similarity	NPC85273
0.7092	Intermediate Similarity	NPC5145
0.709	Intermediate Similarity	NPC267928
0.7083	Intermediate Similarity	NPC477974
0.7079	Intermediate Similarity	NPC253314
0.7079	Intermediate Similarity	NPC474409
0.7074	Intermediate Similarity	NPC326634
0.7072	Intermediate Similarity	NPC168486
0.7072	Intermediate Similarity	NPC222592
0.7069	Intermediate Similarity	NPC71079
0.7066	Intermediate Similarity	NPC470395
0.7062	Intermediate Similarity	NPC476518
0.7062	Intermediate Similarity	NPC477113
0.7062	Intermediate Similarity	NPC164664
0.7049	Intermediate Similarity	NPC207851
0.7045	Intermediate Similarity	NPC41717
0.7039	Intermediate Similarity	NPC297486
0.7039	Intermediate Similarity	NPC240136
0.7039	Intermediate Similarity	NPC471402
0.7037	Intermediate Similarity	NPC251090
0.7035	Intermediate Similarity	NPC237740
0.7027	Intermediate Similarity	NPC206186
0.7025	Intermediate Similarity	NPC278451
0.7019	Intermediate Similarity	NPC322488
0.7016	Intermediate Similarity	NPC4071
0.7016	Intermediate Similarity	NPC476582
0.7016	Intermediate Similarity	NPC476578
0.7011	Intermediate Similarity	NPC94943
0.701	Intermediate Similarity	NPC164374
0.701	Intermediate Similarity	NPC137929
0.701	Intermediate Similarity	NPC210256
0.7005	Intermediate Similarity	NPC11464
0.7005	Intermediate Similarity	NPC309845
0.6995	Remote Similarity	NPC212535
0.6994	Remote Similarity	NPC328029
0.6994	Remote Similarity	NPC138018
0.6982	Remote Similarity	NPC257142
0.698	Remote Similarity	NPC313804
0.698	Remote Similarity	NPC193267
0.698	Remote Similarity	NPC315804
0.698	Remote Similarity	NPC213530
0.6979	Remote Similarity	NPC315491
0.6979	Remote Similarity	NPC45459
0.6979	Remote Similarity	NPC249040
0.6979	Remote Similarity	NPC213308
0.6979	Remote Similarity	NPC477019
0.6978	Remote Similarity	NPC478032
0.6974	Remote Similarity	NPC476124

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 NPC473057 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	618
0.2-0.3	852
0.3-0.4	997
0.4-0.5	3262
0.5-0.6	2471
0.6-0.7	639
0.7-0.8	80
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8383	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD6361	Phase 2
0.8023	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD926	Approved
0.8012	Intermediate Similarity	NPD925	Approved
0.8012	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3813	Approved
0.7917	Intermediate Similarity	NPD2781	Approved
0.7904	Intermediate Similarity	NPD2782	Approved
0.7904	Intermediate Similarity	NPD2780	Approved
0.7892	Intermediate Similarity	NPD1684	Approved
0.7892	Intermediate Similarity	NPD1685	Approved
0.7841	Intermediate Similarity	NPD4375	Approved
0.7824	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD9284	Approved
0.7791	Intermediate Similarity	NPD5100	Phase 3
0.7771	Intermediate Similarity	NPD5255	Approved
0.7751	Intermediate Similarity	NPD424	Approved
0.7751	Intermediate Similarity	NPD425	Approved
0.7714	Intermediate Similarity	NPD3386	Phase 2
0.7711	Intermediate Similarity	NPD9382	Approved
0.7711	Intermediate Similarity	NPD9383	Approved
0.768	Intermediate Similarity	NPD4551	Phase 2
0.7673	Intermediate Similarity	NPD1649	Discontinued
0.7651	Intermediate Similarity	NPD6026	Approved
0.764	Intermediate Similarity	NPD8823	Approved
0.7607	Intermediate Similarity	NPD4703	Approved
0.7607	Intermediate Similarity	NPD4702	Approved
0.7594	Intermediate Similarity	NPD4044	Discontinued
0.7582	Intermediate Similarity	NPD9080	Approved
0.7571	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD9690	Approved
0.7515	Intermediate Similarity	NPD9705	Discontinued
0.7515	Intermediate Similarity	NPD112	Approved
0.75	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4889	Approved
0.7484	Intermediate Similarity	NPD9506	Approved
0.7459	Intermediate Similarity	NPD4021	Phase 2
0.7443	Intermediate Similarity	NPD6159	Phase 2
0.7439	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2896	Discontinued
0.7438	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6569	Phase 2
0.7423	Intermediate Similarity	NPD1352	Discontinued
0.7418	Intermediate Similarity	NPD1213	Phase 3
0.7412	Intermediate Similarity	NPD2511	Approved
0.7412	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2581	Approved
0.7396	Intermediate Similarity	NPD2582	Approved
0.7366	Intermediate Similarity	NPD1229	Phase 2
0.7365	Intermediate Similarity	NPD3262	Approved
0.7362	Intermediate Similarity	NPD3717	Discontinued
0.7354	Intermediate Similarity	NPD6975	Discontinued
0.7351	Intermediate Similarity	NPD3396	Approved
0.7351	Intermediate Similarity	NPD3395	Approved
0.7345	Intermediate Similarity	NPD1032	Phase 2
0.734	Intermediate Similarity	NPD6389	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3923	Approved
0.7337	Intermediate Similarity	NPD3924	Approved
0.7337	Intermediate Similarity	NPD3921	Approved
0.7337	Intermediate Similarity	NPD3922	Approved
0.7326	Intermediate Similarity	NPD5088	Discontinued
0.7297	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2952	Discontinued
0.7273	Intermediate Similarity	NPD7948	Phase 1
0.7262	Intermediate Similarity	NPD2882	Phase 1
0.7249	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6635	Approved
0.7216	Intermediate Similarity	NPD2123	Phase 3
0.7215	Intermediate Similarity	NPD9206	Approved
0.7215	Intermediate Similarity	NPD9207	Approved
0.7213	Intermediate Similarity	NPD2383	Phase 1
0.7212	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD802	Phase 2
0.7198	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7069	Discontinued
0.7193	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4122	Approved
0.7188	Intermediate Similarity	NPD32	Approved
0.7188	Intermediate Similarity	NPD31	Approved
0.7188	Intermediate Similarity	NPD4034	Approved
0.7188	Intermediate Similarity	NPD4039	Approved
0.7188	Intermediate Similarity	NPD4036	Approved
0.7188	Intermediate Similarity	NPD4033	Approved
0.7188	Intermediate Similarity	NPD4035	Approved
0.7188	Intermediate Similarity	NPD4038	Approved
0.7188	Intermediate Similarity	NPD4037	Approved
0.7167	Intermediate Similarity	NPD2600	Approved
0.7167	Intermediate Similarity	NPD2599	Approved
0.7167	Intermediate Similarity	NPD2601	Approved
0.7166	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3039	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5065	Approved
0.7134	Intermediate Similarity	NPD2118	Approved
0.7134	Intermediate Similarity	NPD2119	Approved
0.7127	Intermediate Similarity	NPD4203	Approved
0.7127	Intermediate Similarity	NPD4204	Approved
0.7126	Intermediate Similarity	NPD861	Approved
0.7126	Intermediate Similarity	NPD862	Approved
0.7126	Intermediate Similarity	NPD863	Approved
0.7117	Intermediate Similarity	NPD852	Discontinued
0.7113	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD9695	Approved
0.7112	Intermediate Similarity	NPD1038	Approved
0.7104	Intermediate Similarity	NPD6241	Phase 1
0.7097	Intermediate Similarity	NPD2334	Discontinued
0.7095	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7021	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3928	Approved
0.7083	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3931	Approved
0.7059	Intermediate Similarity	NPD4372	Phase 1
0.7059	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6158	Phase 2
0.7056	Intermediate Similarity	NPD4071	Approved
0.7056	Intermediate Similarity	NPD4072	Approved
0.7053	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3525	Discontinued
0.7043	Intermediate Similarity	NPD8063	Discontinued
0.7043	Intermediate Similarity	NPD6281	Approved
0.7041	Intermediate Similarity	NPD4437	Phase 3
0.7037	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3477	Phase 2
0.7024	Intermediate Similarity	NPD7469	Discontinued
0.7019	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2177	Approved
0.7016	Intermediate Similarity	NPD2175	Phase 3
0.7016	Intermediate Similarity	NPD2176	Approved
0.7011	Intermediate Similarity	NPD3082	Discontinued
0.7006	Intermediate Similarity	NPD5862	Discovery
0.7	Intermediate Similarity	NPD1622	Discontinued
0.6981	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6219	Discontinued
0.6979	Remote Similarity	NPD484	Approved
0.6975	Remote Similarity	NPD4029	Approved
0.6975	Remote Similarity	NPD4030	Approved
0.6975	Remote Similarity	NPD4028	Approved
0.6974	Remote Similarity	NPD6728	Phase 3
0.6968	Remote Similarity	NPD9689	Approved
0.6968	Remote Similarity	NPD3404	Approved
0.6964	Remote Similarity	NPD9074	Approved
0.6964	Remote Similarity	NPD9075	Approved
0.6952	Remote Similarity	NPD3321	Discontinued
0.6941	Remote Similarity	NPD3575	Approved
0.6941	Remote Similarity	NPD3576	Approved
0.694	Remote Similarity	NPD1570	Approved
0.6935	Remote Similarity	NPD3330	Phase 1
0.6935	Remote Similarity	NPD8021	Approved
0.6935	Remote Similarity	NPD8020	Approved
0.6935	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1034	Phase 3
0.6931	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4795	Phase 2
0.6915	Remote Similarity	NPD7112	Discontinued
0.6915	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7123	Suspended
0.6904	Remote Similarity	NPD2916	Discontinued
0.6895	Remote Similarity	NPD3017	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3475	Approved
0.6894	Remote Similarity	NPD3476	Approved
0.6891	Remote Similarity	NPD1740	Approved
0.6891	Remote Similarity	NPD1739	Approved
0.6889	Remote Similarity	NPD2076	Approved
0.6889	Remote Similarity	NPD2077	Approved
0.6885	Remote Similarity	NPD9510	Approved
0.6882	Remote Similarity	NPD4921	Phase 3
0.6882	Remote Similarity	NPD4919	Phase 3
0.6882	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2809	Approved
0.6875	Remote Similarity	NPD8026	Phase 1
0.6871	Remote Similarity	NPD3942	Approved
0.6871	Remote Similarity	NPD3944	Approved
0.685	Remote Similarity	NPD3815	Phase 1
0.685	Remote Similarity	NPD3816	Phase 1
0.6847	Remote Similarity	NPD2021	Discontinued
0.6839	Remote Similarity	NPD5999	Phase 2
0.6831	Remote Similarity	NPD3920	Phase 2
0.6825	Remote Similarity	NPD4699	Discontinued
0.6821	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4638	Approved
0.6816	Remote Similarity	NPD4640	Approved
0.6816	Remote Similarity	NPD4639	Approved
0.6816	Remote Similarity	NPD2615	Phase 3
0.6816	Remote Similarity	NPD2616	Phase 3
0.6814	Remote Similarity	NPD6500	Approved
0.6814	Remote Similarity	NPD6501	Approved
0.68	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5939	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