NPASS Compound

Structure

NPC133306 OpenBabel07101718192D 21 24 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2596 -1.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8965 -1.6241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5651 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5075 -2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8388 -2.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.1444 -2.7272 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6651 -2.9561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 20 1 0 0 0 0 7 10 2 0 0 0 0 8 11 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 11 7 1 1 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 1 0 0 0 14 19 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 6 0 0 0 17 9 1 1 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.13
Volume:	303.811
LogP:	2.627
LogD:	2.704
LogS:	-2.955
# Rotatable Bonds:	0
TPSA:	36.1
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	5.368
Fsp3:	0.588
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.972
MDCK Permeability:	1.1609222383412998e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.592
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.766
Plasma Protein Binding (PPB):	71.22940063476562%
Volume Distribution (VD):	2.052
Pgp-substrate:	21.48353385925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.494
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.386
CYP2C9-substrate:	0.441
CYP2D6-inhibitor:	0.159
CYP2D6-substrate:	0.802
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.895

ADMET: Excretion

Clearance (CL):	5.775
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.235
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.141
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.455
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.127
Carcinogencity:	0.274
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC133306

Natural Product ID:	NPC133306
*Common Name:**	RRGNVROICAKYCS-LPOXYFBYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RRGNVROICAKYCS-LPOXYFBYSA-N
Standard InCHI:	InChI=1S/C17H21ClN2O/c1-10-7-11-8-14-12(3-4-15(21)19-14)17(9-10)16(11)13(18)5-6-20(17)2/h3-4,7,11,13,16H,5-6,8-9H2,1-2H3,(H,19,21)/t11-,13+,16-,17-/m0/s1
SMILES:	CC1=C[C@H]2Cc3c(ccc(n3)O)[C@@]3(C1)[C@@H]2[C@@H](CCN3C)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409140
PubChem CID:	72192858
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO32769	lycopodiastrum casuarinoides	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23941108]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	20900.0	nM	PMID[558808]

☑ 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 NPC133306 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	514
0.1-0.2	3299
0.2-0.3	12521
0.3-0.4	14454
0.4-0.5	7169
0.5-0.6	3566
0.6-0.7	1112
0.7-0.8	44
0.8-0.85	5
0.85-0.9	10
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9222	High Similarity	NPC232340
0.9212	High Similarity	NPC471294
0.8982	High Similarity	NPC259545
0.8848	High Similarity	NPC32028
0.8788	High Similarity	NPC47298
0.8788	High Similarity	NPC315214
0.8735	High Similarity	NPC159319
0.8529	High Similarity	NPC126481
0.8483	Intermediate Similarity	NPC183805
0.8197	Intermediate Similarity	NPC45850
0.8118	Intermediate Similarity	NPC84508
0.7727	Intermediate Similarity	NPC471178
0.7665	Intermediate Similarity	NPC60553
0.7614	Intermediate Similarity	NPC59779
0.7614	Intermediate Similarity	NPC124542
0.7614	Intermediate Similarity	NPC471177
0.7571	Intermediate Similarity	NPC473057
0.7571	Intermediate Similarity	NPC97367
0.7485	Intermediate Similarity	NPC161292
0.7474	Intermediate Similarity	NPC249040
0.7389	Intermediate Similarity	NPC98187
0.7314	Intermediate Similarity	NPC153769
0.7294	Intermediate Similarity	NPC245657
0.7268	Intermediate Similarity	NPC158129
0.7254	Intermediate Similarity	NPC329541
0.7243	Intermediate Similarity	NPC203754
0.7243	Intermediate Similarity	NPC150048
0.7235	Intermediate Similarity	NPC280853
0.7214	Intermediate Similarity	NPC475910
0.7214	Intermediate Similarity	NPC477111
0.7214	Intermediate Similarity	NPC470931
0.7208	Intermediate Similarity	NPC329793
0.7198	Intermediate Similarity	NPC108469
0.7193	Intermediate Similarity	NPC285016
0.7188	Intermediate Similarity	NPC3715
0.7178	Intermediate Similarity	NPC476116
0.7176	Intermediate Similarity	NPC471596
0.7173	Intermediate Similarity	NPC206186
0.7166	Intermediate Similarity	NPC72980
0.7143	Intermediate Similarity	NPC19679
0.7136	Intermediate Similarity	NPC183407
0.7135	Intermediate Similarity	NPC128751
0.7135	Intermediate Similarity	NPC246700
0.7128	Intermediate Similarity	NPC478032
0.7114	Intermediate Similarity	NPC474145
0.7114	Intermediate Similarity	NPC472111
0.7114	Intermediate Similarity	NPC475841
0.7114	Intermediate Similarity	NPC477113
0.7113	Intermediate Similarity	NPC114335
0.7113	Intermediate Similarity	NPC280964
0.7113	Intermediate Similarity	NPC141915
0.7112	Intermediate Similarity	NPC326575
0.7098	Intermediate Similarity	NPC469497
0.7098	Intermediate Similarity	NPC106833
0.7076	Intermediate Similarity	NPC471594
0.7074	Intermediate Similarity	NPC88363
0.7069	Intermediate Similarity	NPC471598
0.7068	Intermediate Similarity	NPC94943
0.7065	Intermediate Similarity	NPC44161
0.7065	Intermediate Similarity	NPC317430
0.7065	Intermediate Similarity	NPC475070
0.7059	Intermediate Similarity	NPC134586
0.7056	Intermediate Similarity	NPC474188
0.7043	Intermediate Similarity	NPC472123
0.7035	Intermediate Similarity	NPC329747
0.7031	Intermediate Similarity	NPC171171
0.7021	Intermediate Similarity	NPC283152
0.7021	Intermediate Similarity	NPC211997
0.7016	Intermediate Similarity	NPC190007
0.7014	Intermediate Similarity	NPC162748
0.7005	Intermediate Similarity	NPC237740
0.699	Remote Similarity	NPC289786
0.698	Remote Similarity	NPC274291
0.698	Remote Similarity	NPC329708
0.698	Remote Similarity	NPC165349
0.698	Remote Similarity	NPC118832
0.698	Remote Similarity	NPC47059
0.698	Remote Similarity	NPC264166
0.6971	Remote Similarity	NPC469928
0.6971	Remote Similarity	NPC330009
0.6971	Remote Similarity	NPC477110
0.6968	Remote Similarity	NPC472122
0.6968	Remote Similarity	NPC24594
0.6968	Remote Similarity	NPC288943
0.6963	Remote Similarity	NPC212535
0.6963	Remote Similarity	NPC6215
0.6957	Remote Similarity	NPC478074
0.695	Remote Similarity	NPC11017
0.6943	Remote Similarity	NPC314573
0.6938	Remote Similarity	NPC476041
0.6938	Remote Similarity	NPC304926
0.6935	Remote Similarity	NPC473764
0.6935	Remote Similarity	NPC314940
0.6927	Remote Similarity	NPC320394
0.6927	Remote Similarity	NPC469589
0.6927	Remote Similarity	NPC204717
0.6923	Remote Similarity	NPC95783
0.6919	Remote Similarity	NPC472193
0.6916	Remote Similarity	NPC214980
0.6915	Remote Similarity	NPC329688
0.6915	Remote Similarity	NPC189812
0.6915	Remote Similarity	NPC303225
0.6912	Remote Similarity	NPC53344
0.6908	Remote Similarity	NPC112206
0.6908	Remote Similarity	NPC202605
0.69	Remote Similarity	NPC476175
0.6898	Remote Similarity	NPC105758
0.6898	Remote Similarity	NPC476686
0.6898	Remote Similarity	NPC476688
0.6895	Remote Similarity	NPC67659
0.6891	Remote Similarity	NPC314002
0.6889	Remote Similarity	NPC26872
0.6886	Remote Similarity	NPC278451
0.6885	Remote Similarity	NPC255229
0.6885	Remote Similarity	NPC81229
0.6884	Remote Similarity	NPC153042
0.6878	Remote Similarity	NPC288785
0.6875	Remote Similarity	NPC220765
0.6868	Remote Similarity	NPC129721
0.6868	Remote Similarity	NPC26850
0.6866	Remote Similarity	NPC476451
0.6862	Remote Similarity	NPC474409
0.6859	Remote Similarity	NPC187827
0.6859	Remote Similarity	NPC472105
0.6854	Remote Similarity	NPC280272
0.6853	Remote Similarity	NPC99666
0.6848	Remote Similarity	NPC177404
0.6839	Remote Similarity	NPC62069
0.6837	Remote Similarity	NPC103687
0.6837	Remote Similarity	NPC132631
0.6834	Remote Similarity	NPC473053
0.6823	Remote Similarity	NPC192270
0.6821	Remote Similarity	NPC254762
0.6821	Remote Similarity	NPC46580
0.6821	Remote Similarity	NPC66083
0.6818	Remote Similarity	NPC470404
0.6818	Remote Similarity	NPC470403
0.6818	Remote Similarity	NPC470394
0.6816	Remote Similarity	NPC476582
0.6816	Remote Similarity	NPC4071
0.6816	Remote Similarity	NPC476578
0.6813	Remote Similarity	NPC141353
0.6812	Remote Similarity	NPC475422
0.6806	Remote Similarity	NPC470126
0.6806	Remote Similarity	NPC133261
0.6798	Remote Similarity	NPC211813
0.6798	Remote Similarity	NPC328318
0.6798	Remote Similarity	NPC328596
0.6796	Remote Similarity	NPC87755
0.6794	Remote Similarity	NPC469592
0.6794	Remote Similarity	NPC471080
0.6793	Remote Similarity	NPC25899
0.6791	Remote Similarity	NPC278874
0.6791	Remote Similarity	NPC473449
0.6788	Remote Similarity	NPC472110
0.6788	Remote Similarity	NPC472108
0.6788	Remote Similarity	NPC472109
0.6788	Remote Similarity	NPC139291
0.6786	Remote Similarity	NPC472289
0.6786	Remote Similarity	NPC32771
0.6776	Remote Similarity	NPC122463
0.6774	Remote Similarity	NPC253580
0.6772	Remote Similarity	NPC208060
0.6771	Remote Similarity	NPC15840
0.6769	Remote Similarity	NPC194040
0.6768	Remote Similarity	NPC195268
0.6768	Remote Similarity	NPC133140
0.6768	Remote Similarity	NPC324149
0.6765	Remote Similarity	NPC469440
0.6765	Remote Similarity	NPC53144
0.6759	Remote Similarity	NPC2497
0.6754	Remote Similarity	NPC293472
0.6742	Remote Similarity	NPC470395
0.6733	Remote Similarity	NPC287437
0.6733	Remote Similarity	NPC476167
0.6732	Remote Similarity	NPC36229
0.6732	Remote Similarity	NPC476581
0.6732	Remote Similarity	NPC164374
0.6732	Remote Similarity	NPC137929
0.6732	Remote Similarity	NPC16452
0.6731	Remote Similarity	NPC471304
0.6724	Remote Similarity	NPC471312
0.6722	Remote Similarity	NPC288445
0.6718	Remote Similarity	NPC42591
0.6718	Remote Similarity	NPC476319
0.6717	Remote Similarity	NPC469390
0.6716	Remote Similarity	NPC77555
0.6716	Remote Similarity	NPC70956
0.6716	Remote Similarity	NPC232130
0.6716	Remote Similarity	NPC243834
0.6716	Remote Similarity	NPC470678
0.6716	Remote Similarity	NPC224928
0.6715	Remote Similarity	NPC18348
0.6714	Remote Similarity	NPC193267
0.6714	Remote Similarity	NPC213530
0.6699	Remote Similarity	NPC317373
0.6699	Remote Similarity	NPC208284
0.6698	Remote Similarity	NPC469727
0.6684	Remote Similarity	NPC61350
0.6683	Remote Similarity	NPC200836

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 NPC133306 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	619
0.2-0.3	889
0.3-0.4	1244
0.4-0.5	3067
0.5-0.6	2463
0.6-0.7	567
0.7-0.8	29
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8788	High Similarity	NPD1685	Approved
0.8788	High Similarity	NPD1684	Approved
0.8324	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD925	Approved
0.7627	Intermediate Similarity	NPD926	Approved
0.754	Intermediate Similarity	NPD2383	Phase 1
0.7538	Intermediate Similarity	NPD4044	Discontinued
0.7514	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2882	Phase 1
0.7514	Intermediate Similarity	NPD6158	Phase 2
0.7401	Intermediate Similarity	NPD5255	Approved
0.7391	Intermediate Similarity	NPD6159	Phase 2
0.7366	Intermediate Similarity	NPD4204	Approved
0.7366	Intermediate Similarity	NPD4203	Approved
0.7363	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD2727	Phase 2
0.725	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD5100	Phase 3
0.7243	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2916	Discontinued
0.7213	Intermediate Similarity	NPD1325	Approved
0.7213	Intermediate Similarity	NPD1326	Approved
0.7158	Intermediate Similarity	NPD6227	Discontinued
0.7157	Intermediate Similarity	NPD2177	Approved
0.7157	Intermediate Similarity	NPD2175	Phase 3
0.7157	Intermediate Similarity	NPD2176	Approved
0.7136	Intermediate Similarity	NPD3928	Approved
0.7136	Intermediate Similarity	NPD3931	Approved
0.7114	Intermediate Similarity	NPD5530	Phase 1
0.7105	Intermediate Similarity	NPD4484	Phase 1
0.7104	Intermediate Similarity	NPD425	Approved
0.7104	Intermediate Similarity	NPD424	Approved
0.7085	Intermediate Similarity	NPD4511	Phase 1
0.7071	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3813	Approved
0.7065	Intermediate Similarity	NPD2781	Approved
0.7059	Intermediate Similarity	NPD2381	Approved
0.7059	Intermediate Similarity	NPD2380	Approved
0.7059	Intermediate Similarity	NPD2382	Approved
0.7049	Intermediate Similarity	NPD2780	Approved
0.7049	Intermediate Similarity	NPD2782	Approved
0.7027	Intermediate Similarity	NPD7474	Suspended
0.7026	Intermediate Similarity	NPD6569	Phase 2
0.7024	Intermediate Similarity	NPD5936	Approved
0.7024	Intermediate Similarity	NPD5939	Approved
0.7014	Intermediate Similarity	NPD7219	Approved
0.7014	Intermediate Similarity	NPD7221	Approved
0.7011	Intermediate Similarity	NPD3525	Discontinued
0.701	Intermediate Similarity	NPD6281	Approved
0.7	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7222	Phase 2
0.699	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4038	Approved
0.698	Remote Similarity	NPD31	Approved
0.698	Remote Similarity	NPD4039	Approved
0.698	Remote Similarity	NPD4035	Approved
0.698	Remote Similarity	NPD4122	Approved
0.698	Remote Similarity	NPD4033	Approved
0.698	Remote Similarity	NPD4036	Approved
0.698	Remote Similarity	NPD4034	Approved
0.698	Remote Similarity	NPD32	Approved
0.698	Remote Similarity	NPD4037	Approved
0.6971	Remote Similarity	NPD7112	Discontinued
0.6971	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7671	Approved
0.6961	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7672	Approved
0.6957	Remote Similarity	NPD3243	Approved
0.6954	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7418	Discontinued
0.6952	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4702	Approved
0.6949	Remote Similarity	NPD4703	Approved
0.6946	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6991	Approved
0.6915	Remote Similarity	NPD6492	Phase 2
0.6915	Remote Similarity	NPD5065	Approved
0.6905	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3975	Discontinued
0.6895	Remote Similarity	NPD3920	Phase 2
0.6893	Remote Similarity	NPD7469	Discontinued
0.6887	Remote Similarity	NPD7726	Phase 1
0.6882	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6975	Discontinued
0.6878	Remote Similarity	NPD6376	Discontinued
0.6875	Remote Similarity	NPD2615	Phase 3
0.6875	Remote Similarity	NPD2616	Phase 3
0.6872	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.685	Remote Similarity	NPD712	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD1213	Phase 3
0.6834	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD3477	Phase 2
0.6832	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6290	Phase 2
0.6827	Remote Similarity	NPD3330	Phase 1
0.6813	Remote Similarity	NPD6026	Approved
0.6811	Remote Similarity	NPD862	Approved
0.6811	Remote Similarity	NPD863	Approved
0.6811	Remote Similarity	NPD861	Approved
0.68	Remote Similarity	NPD7948	Phase 1
0.68	Remote Similarity	NPD1229	Phase 2
0.6791	Remote Similarity	NPD5862	Discovery
0.6784	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4502	Phase 2
0.6776	Remote Similarity	NPD2581	Approved
0.6776	Remote Similarity	NPD2582	Approved
0.6774	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2076	Approved
0.6772	Remote Similarity	NPD2077	Approved
0.6769	Remote Similarity	NPD4375	Approved
0.6768	Remote Similarity	NPD3924	Approved
0.6768	Remote Similarity	NPD3404	Approved
0.6768	Remote Similarity	NPD4909	Approved
0.6768	Remote Similarity	NPD3923	Approved
0.6768	Remote Similarity	NPD3921	Approved
0.6768	Remote Similarity	NPD3922	Approved
0.6765	Remote Similarity	NPD4886	Phase 2
0.6761	Remote Similarity	NPD5020	Approved
0.6754	Remote Similarity	NPD1032	Phase 2
0.6753	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD8063	Discontinued
0.6748	Remote Similarity	NPD7453	Approved
0.6748	Remote Similarity	NPD7452	Approved
0.674	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD9690	Approved
0.6736	Remote Similarity	NPD7867	Phase 1
0.6734	Remote Similarity	NPD4551	Phase 2
0.6733	Remote Similarity	NPD3814	Phase 1
0.6723	Remote Similarity	NPD3717	Discontinued
0.6719	Remote Similarity	NPD3417	Phase 1
0.6718	Remote Similarity	NPD4889	Approved
0.6718	Remote Similarity	NPD2762	Phase 2
0.6718	Remote Similarity	NPD3082	Discontinued
0.6705	Remote Similarity	NPD1649	Discontinued
0.6703	Remote Similarity	NPD112	Approved
0.6703	Remote Similarity	NPD9705	Discontinued
0.67	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD852	Discontinued
0.6684	Remote Similarity	NPD6452	Discontinued
0.6684	Remote Similarity	NPD3315	Phase 3
0.6683	Remote Similarity	NPD9689	Approved
0.6667	Remote Similarity	NPD5316	Approved
0.6667	Remote Similarity	NPD6307	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4529	Approved
0.665	Remote Similarity	NPD8396	Approved
0.665	Remote Similarity	NPD4528	Approved
0.665	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6361	Phase 2
0.665	Remote Similarity	NPD8021	Approved
0.665	Remote Similarity	NPD8020	Approved
0.665	Remote Similarity	NPD8395	Approved
0.665	Remote Similarity	NPD4526	Approved
0.6648	Remote Similarity	NPD2075	Approved
0.6648	Remote Similarity	NPD2073	Approved
0.6648	Remote Similarity	NPD2074	Approved
0.6648	Remote Similarity	NPD2072	Approved
0.6647	Remote Similarity	NPD3944	Approved
0.6647	Remote Similarity	NPD3942	Approved
0.6636	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4699	Discontinued
0.6633	Remote Similarity	NPD5913	Phase 3
0.6633	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD5140	Approved
0.6631	Remote Similarity	NPD444	Approved
0.6631	Remote Similarity	NPD5138	Approved
0.662	Remote Similarity	NPD1856	Discontinued
0.6617	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6590	Discontinued
0.6616	Remote Similarity	NPD408	Approved
0.6611	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4897	Phase 2
0.6597	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD6497	Approved
0.6591	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD2118	Approved
0.6588	Remote Similarity	NPD2119	Approved
0.6588	Remote Similarity	NPD9284	Approved
0.6587	Remote Similarity	NPD1197	Approved
0.6578	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD6285	Phase 2
0.6576	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5507	Approved
0.6574	Remote Similarity	NPD5506	Approved
0.657	Remote Similarity	NPD4795	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