NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.16
Volume:	271.304
LogP:	0.976
LogD:	1.196
LogS:	-2.706
# Rotatable Bonds:	0
TPSA:	44.89
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.698
Synthetic Accessibility Score:	5.005
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.326
MDCK Permeability:	8.445210369245615e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.876
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.635
Plasma Protein Binding (PPB):	38.12815856933594%
Volume Distribution (VD):	1.437
Pgp-substrate:	43.08342742919922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.875
CYP2C19-inhibitor:	0.394
CYP2C19-substrate:	0.258
CYP2C9-inhibitor:	0.12
CYP2C9-substrate:	0.368
CYP2D6-inhibitor:	0.275
CYP2D6-substrate:	0.836
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.571

ADMET: Excretion

Clearance (CL):	5.129
Half-life (T1/2):	0.718

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.649
Drug-inuced Liver Injury (DILI):	0.065
AMES Toxicity:	0.205
Rat Oral Acute Toxicity:	0.904
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.328
Carcinogencity:	0.055
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC232340

Natural Product ID:	NPC232340
*Common Name:**	Huperzine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YYWGABLTRMRUIT-HWWQOWPSSA-N
Standard InCHI:	InChI=1S/C16H20N2O/c1-10-7-11-8-14-13(4-5-15(19)18-14)16(9-10)12(11)3-2-6-17-16/h4-5,7,11-12,17H,2-3,6,8-9H2,1H3,(H,18,19)/t11-,12+,16+/m0/s1
SMILES:	CC1=C[C@H]2Cc3c([C@@]4(C1)[C@@H]2CCCN4)ccc(n3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL245079
PubChem CID:	5462442
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
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141864]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14928	Huperzia serrata	Species	Lycopodiaceae	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
ED50	1
IC50	5
Ki	2
Others	6

Activity Type	# Activity
Individual Protein	8
Organism	5
Others	1
SELECTIVITY GROUP	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	30.0	nM	PMID[499302]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	EC50	=	19.0	nM	PMID[499302]
NPT2749	Individual Protein	Acetylcholinesterase	Rattus norvegicus	IC50	=	19300.0	nM	PMID[499303]
NPT2748	Individual Protein	Butyrylcholinesterase	Rattus norvegicus	IC50	=	227000.0	nM	PMID[499303]
NPT2749	Individual Protein	Acetylcholinesterase	Rattus norvegicus	IC50	=	19300.0	nM	PMID[499304]
NPT2748	Individual Protein	Butyrylcholinesterase	Rattus norvegicus	IC50	=	228000.0	nM	PMID[499304]
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	Ki	=	334.0	nM	PMID[499305]
NPT914	Individual Protein	Acetylcholinesterase	Bos taurus	Ki	=	794.0	nM	PMID[499301]
NPT1403	Organism	Felis catus	Felis catus	ED50	=	0.08	umol.kg-1	PMID[499302]
NPT1403	Organism	Felis catus	Felis catus	Max rev	=	156.0	%	PMID[499302]
NPT1403	Organism	Felis catus	Felis catus	MAP	=	-17.0	delta %	PMID[499302]
NPT1403	Organism	Felis catus	Felis catus	HR	=	-8.0	delta %	PMID[499302]
NPT1403	Organism	Felis catus	Felis catus	Vagus	=	102.0	delta %	PMID[499302]
NPT26049	SELECTIVITY GROUP	Acetylcholinesterase and butyrylcholinesterase (AChE and BChE)	Rattus norvegicus	Selectivity index	=	11.8	n.a.	PMID[499303]
NPT2	Others	Unspecified		Ratio IC50	=	12.0	n.a.	PMID[499304]

☑ 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 NPC232340 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	478
0.1-0.2	2960
0.2-0.3	12335
0.3-0.4	14173
0.4-0.5	7423
0.5-0.6	3519
0.6-0.7	1653
0.7-0.8	137
0.8-0.85	3
0.85-0.9	3
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC259545
0.9371	High Similarity	NPC32028
0.9308	High Similarity	NPC315214
0.9308	High Similarity	NPC47298
0.9264	High Similarity	NPC471294
0.925	High Similarity	NPC159319
0.9222	High Similarity	NPC133306
0.9024	High Similarity	NPC126481
0.8857	High Similarity	NPC45850
0.8523	High Similarity	NPC183805
0.8155	Intermediate Similarity	NPC84508
0.7872	Intermediate Similarity	NPC249040
0.7805	Intermediate Similarity	NPC60553
0.7759	Intermediate Similarity	NPC471178
0.7701	Intermediate Similarity	NPC97367
0.7701	Intermediate Similarity	NPC473057
0.768	Intermediate Similarity	NPC477111
0.7668	Intermediate Similarity	NPC477113
0.7667	Intermediate Similarity	NPC72980
0.7644	Intermediate Similarity	NPC124542
0.7644	Intermediate Similarity	NPC59779
0.7644	Intermediate Similarity	NPC471177
0.7641	Intermediate Similarity	NPC476116
0.7622	Intermediate Similarity	NPC246700
0.7622	Intermediate Similarity	NPC128751
0.7619	Intermediate Similarity	NPC161292
0.7592	Intermediate Similarity	NPC329793
0.759	Intermediate Similarity	NPC475910
0.7588	Intermediate Similarity	NPC183407
0.7581	Intermediate Similarity	NPC469497
0.7581	Intermediate Similarity	NPC106833
0.7569	Intermediate Similarity	NPC88363
0.7554	Intermediate Similarity	NPC94943
0.7541	Intermediate Similarity	NPC19679
0.7514	Intermediate Similarity	NPC171171
0.75	Intermediate Similarity	NPC204717
0.75	Intermediate Similarity	NPC477110
0.75	Intermediate Similarity	NPC190007
0.7472	Intermediate Similarity	NPC317430
0.7459	Intermediate Similarity	NPC314002
0.7451	Intermediate Similarity	NPC162748
0.7446	Intermediate Similarity	NPC220765
0.7446	Intermediate Similarity	NPC212535
0.7444	Intermediate Similarity	NPC472123
0.7442	Intermediate Similarity	NPC153769
0.7436	Intermediate Similarity	NPC475070
0.7425	Intermediate Similarity	NPC245657
0.7416	Intermediate Similarity	NPC98187
0.7409	Intermediate Similarity	NPC329747
0.7407	Intermediate Similarity	NPC99666
0.7394	Intermediate Similarity	NPC95783
0.738	Intermediate Similarity	NPC46580
0.7368	Intermediate Similarity	NPC329541
0.7365	Intermediate Similarity	NPC280853
0.7348	Intermediate Similarity	NPC474409
0.7344	Intermediate Similarity	NPC153042
0.7327	Intermediate Similarity	NPC469928
0.7327	Intermediate Similarity	NPC330009
0.7321	Intermediate Similarity	NPC285016
0.7318	Intermediate Similarity	NPC108469
0.7316	Intermediate Similarity	NPC324149
0.7314	Intermediate Similarity	NPC141353
0.7313	Intermediate Similarity	NPC478074
0.7308	Intermediate Similarity	NPC6215
0.7308	Intermediate Similarity	NPC329688
0.7308	Intermediate Similarity	NPC189812
0.7305	Intermediate Similarity	NPC471596
0.7302	Intermediate Similarity	NPC3715
0.7293	Intermediate Similarity	NPC158129
0.7291	Intermediate Similarity	NPC304926
0.7291	Intermediate Similarity	NPC476041
0.7287	Intermediate Similarity	NPC206186
0.7282	Intermediate Similarity	NPC280272
0.7268	Intermediate Similarity	NPC203754
0.7268	Intermediate Similarity	NPC150048
0.7258	Intermediate Similarity	NPC472109
0.7258	Intermediate Similarity	NPC472110
0.7254	Intermediate Similarity	NPC77555
0.7249	Intermediate Similarity	NPC32771
0.7243	Intermediate Similarity	NPC478032
0.7236	Intermediate Similarity	NPC470931
0.7228	Intermediate Similarity	NPC184964
0.7225	Intermediate Similarity	NPC114335
0.7225	Intermediate Similarity	NPC141915
0.7225	Intermediate Similarity	NPC280964
0.7208	Intermediate Similarity	NPC476098
0.7206	Intermediate Similarity	NPC469727
0.7202	Intermediate Similarity	NPC471594
0.7193	Intermediate Similarity	NPC471598
0.7182	Intermediate Similarity	NPC44161
0.7181	Intermediate Similarity	NPC476319
0.7175	Intermediate Similarity	NPC193740
0.7166	Intermediate Similarity	NPC472108
0.7166	Intermediate Similarity	NPC139291
0.7165	Intermediate Similarity	NPC243834
0.7165	Intermediate Similarity	NPC474188
0.7165	Intermediate Similarity	NPC70956
0.7164	Intermediate Similarity	NPC475422
0.7151	Intermediate Similarity	NPC16667
0.715	Intermediate Similarity	NPC18348
0.715	Intermediate Similarity	NPC87755
0.7143	Intermediate Similarity	NPC280548
0.7143	Intermediate Similarity	NPC470126
0.7143	Intermediate Similarity	NPC471080
0.7143	Intermediate Similarity	NPC469592
0.7136	Intermediate Similarity	NPC213530
0.7136	Intermediate Similarity	NPC474145
0.7136	Intermediate Similarity	NPC475841
0.7136	Intermediate Similarity	NPC193267
0.7136	Intermediate Similarity	NPC472111
0.7135	Intermediate Similarity	NPC283152
0.7135	Intermediate Similarity	NPC326575
0.7135	Intermediate Similarity	NPC96890
0.7129	Intermediate Similarity	NPC208284
0.7128	Intermediate Similarity	NPC472294
0.7123	Intermediate Similarity	NPC476451
0.7121	Intermediate Similarity	NPC223427
0.7119	Intermediate Similarity	NPC285469
0.7113	Intermediate Similarity	NPC242209
0.7109	Intermediate Similarity	NPC253580
0.7108	Intermediate Similarity	NPC237740
0.7098	Intermediate Similarity	NPC289786
0.7095	Intermediate Similarity	NPC131718
0.7094	Intermediate Similarity	NPC294620
0.7092	Intermediate Similarity	NPC476167
0.7088	Intermediate Similarity	NPC154293
0.7081	Intermediate Similarity	NPC134586
0.7081	Intermediate Similarity	NPC288943
0.7079	Intermediate Similarity	NPC5145
0.7079	Intermediate Similarity	NPC471304
0.7079	Intermediate Similarity	NPC167635
0.7077	Intermediate Similarity	NPC156704
0.7077	Intermediate Similarity	NPC232130
0.7074	Intermediate Similarity	NPC176127
0.7071	Intermediate Similarity	NPC475112
0.7071	Intermediate Similarity	NPC291535
0.7071	Intermediate Similarity	NPC475085
0.7065	Intermediate Similarity	NPC34508
0.7065	Intermediate Similarity	NPC313791
0.7062	Intermediate Similarity	NPC195314
0.7062	Intermediate Similarity	NPC276517
0.7053	Intermediate Similarity	NPC314573
0.7049	Intermediate Similarity	NPC473764
0.7049	Intermediate Similarity	NPC314940
0.7043	Intermediate Similarity	NPC211997
0.7043	Intermediate Similarity	NPC151939
0.7041	Intermediate Similarity	NPC306376
0.7041	Intermediate Similarity	NPC192315
0.7041	Intermediate Similarity	NPC265576
0.7037	Intermediate Similarity	NPC320394
0.7037	Intermediate Similarity	NPC84478
0.7033	Intermediate Similarity	NPC474561
0.7033	Intermediate Similarity	NPC49954
0.7029	Intermediate Similarity	NPC288445
0.7027	Intermediate Similarity	NPC303225
0.7026	Intermediate Similarity	NPC472193
0.702	Intermediate Similarity	NPC267423
0.7017	Intermediate Similarity	NPC476118
0.7015	Intermediate Similarity	NPC193777
0.7015	Intermediate Similarity	NPC270918
0.7012	Intermediate Similarity	NPC278451
0.7011	Intermediate Similarity	NPC476688
0.7011	Intermediate Similarity	NPC105758
0.7011	Intermediate Similarity	NPC476686
0.7011	Intermediate Similarity	NPC201634
0.701	Intermediate Similarity	NPC307963
0.7006	Intermediate Similarity	NPC26872
0.7005	Intermediate Similarity	NPC469594
0.7005	Intermediate Similarity	NPC41679
0.7005	Intermediate Similarity	NPC67659
0.7	Intermediate Similarity	NPC47059
0.7	Intermediate Similarity	NPC285558
0.7	Intermediate Similarity	NPC165349
0.7	Intermediate Similarity	NPC329708
0.7	Intermediate Similarity	NPC118832
0.7	Intermediate Similarity	NPC264166
0.7	Intermediate Similarity	NPC274291
0.699	Remote Similarity	NPC473814
0.699	Remote Similarity	NPC78767
0.6989	Remote Similarity	NPC472122
0.6989	Remote Similarity	NPC24594
0.6983	Remote Similarity	NPC26850
0.6976	Remote Similarity	NPC477610
0.6971	Remote Similarity	NPC21605
0.697	Remote Similarity	NPC11017
0.6966	Remote Similarity	NPC207726
0.6961	Remote Similarity	NPC177404
0.6947	Remote Similarity	NPC62069
0.6946	Remote Similarity	NPC469589
0.6944	Remote Similarity	NPC67056
0.6943	Remote Similarity	NPC469501
0.6943	Remote Similarity	NPC76748
0.6943	Remote Similarity	NPC469470
0.6941	Remote Similarity	NPC81175
0.694	Remote Similarity	NPC160105
0.6939	Remote Similarity	NPC251090
0.6939	Remote Similarity	NPC473053
0.6936	Remote Similarity	NPC470404
0.6936	Remote Similarity	NPC470403
0.6936	Remote Similarity	NPC470394

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 NPC232340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	565
0.2-0.3	885
0.3-0.4	1190
0.4-0.5	2748
0.5-0.6	2658
0.6-0.7	777
0.7-0.8	65
0.8-0.85	2
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9308	High Similarity	NPD1684	Approved
0.9308	High Similarity	NPD1685	Approved
0.8667	High Similarity	NPD5497	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1326	Approved
0.7829	Intermediate Similarity	NPD1325	Approved
0.7759	Intermediate Similarity	NPD926	Approved
0.7759	Intermediate Similarity	NPD925	Approved
0.7725	Intermediate Similarity	NPD2177	Approved
0.7725	Intermediate Similarity	NPD2176	Approved
0.7725	Intermediate Similarity	NPD2175	Phase 3
0.7654	Intermediate Similarity	NPD2380	Approved
0.7654	Intermediate Similarity	NPD2381	Approved
0.7654	Intermediate Similarity	NPD2382	Approved
0.7647	Intermediate Similarity	NPD6158	Phase 2
0.7647	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2916	Discontinued
0.7568	Intermediate Similarity	NPD2383	Phase 1
0.7565	Intermediate Similarity	NPD4044	Discontinued
0.7563	Intermediate Similarity	NPD5936	Approved
0.7563	Intermediate Similarity	NPD5939	Approved
0.7552	Intermediate Similarity	NPD4511	Phase 1
0.7544	Intermediate Similarity	NPD2882	Phase 1
0.7514	Intermediate Similarity	NPD424	Approved
0.7514	Intermediate Similarity	NPD6159	Phase 2
0.7514	Intermediate Similarity	NPD425	Approved
0.746	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5255	Approved
0.7421	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5065	Approved
0.7401	Intermediate Similarity	NPD861	Approved
0.7401	Intermediate Similarity	NPD863	Approved
0.7401	Intermediate Similarity	NPD862	Approved
0.7391	Intermediate Similarity	NPD4204	Approved
0.7391	Intermediate Similarity	NPD4203	Approved
0.7389	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5100	Phase 3
0.736	Intermediate Similarity	NPD6290	Phase 2
0.736	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7948	Phase 1
0.734	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7726	Phase 1
0.7316	Intermediate Similarity	NPD3404	Approved
0.73	Intermediate Similarity	NPD4502	Phase 2
0.7297	Intermediate Similarity	NPD7867	Phase 1
0.7268	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3814	Phase 1
0.7236	Intermediate Similarity	NPD6376	Discontinued
0.7222	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6492	Phase 2
0.7193	Intermediate Similarity	NPD3813	Approved
0.7182	Intermediate Similarity	NPD2781	Approved
0.7181	Intermediate Similarity	NPD6227	Discontinued
0.7178	Intermediate Similarity	NPD3330	Phase 1
0.7168	Intermediate Similarity	NPD4703	Approved
0.7168	Intermediate Similarity	NPD4702	Approved
0.7167	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD2782	Approved
0.7167	Intermediate Similarity	NPD2780	Approved
0.715	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7474	Suspended
0.7136	Intermediate Similarity	NPD5530	Phase 1
0.7135	Intermediate Similarity	NPD3525	Discontinued
0.7112	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD8395	Approved
0.7092	Intermediate Similarity	NPD8396	Approved
0.709	Intermediate Similarity	NPD2762	Phase 2
0.7079	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3928	Approved
0.7071	Intermediate Similarity	NPD3931	Approved
0.7065	Intermediate Similarity	NPD7418	Discontinued
0.7062	Intermediate Similarity	NPD4999	Phase 3
0.7062	Intermediate Similarity	NPD4998	Phase 3
0.7059	Intermediate Similarity	NPD3243	Approved
0.7053	Intermediate Similarity	NPD5256	Discontinued
0.7047	Intermediate Similarity	NPD6569	Phase 2
0.7043	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4886	Phase 2
0.7031	Intermediate Similarity	NPD6281	Approved
0.7017	Intermediate Similarity	NPD5138	Approved
0.7017	Intermediate Similarity	NPD5140	Approved
0.7015	Intermediate Similarity	NPD7222	Phase 2
0.7011	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD1038	Approved
0.701	Intermediate Similarity	NPD5428	Discontinued
0.7005	Intermediate Similarity	NPD3920	Phase 2
0.7005	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4036	Approved
0.7	Intermediate Similarity	NPD4037	Approved
0.7	Intermediate Similarity	NPD4122	Approved
0.7	Intermediate Similarity	NPD3082	Discontinued
0.7	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4039	Approved
0.7	Intermediate Similarity	NPD4035	Approved
0.7	Intermediate Similarity	NPD4033	Approved
0.7	Intermediate Similarity	NPD32	Approved
0.7	Intermediate Similarity	NPD31	Approved
0.7	Intermediate Similarity	NPD4795	Phase 2
0.7	Intermediate Similarity	NPD4034	Approved
0.7	Intermediate Similarity	NPD4038	Approved
0.6995	Remote Similarity	NPD5913	Phase 3
0.6995	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7112	Discontinued
0.699	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4462	Approved
0.6989	Remote Similarity	NPD4463	Approved
0.698	Remote Similarity	NPD7671	Approved
0.698	Remote Similarity	NPD7672	Approved
0.6979	Remote Similarity	NPD4021	Phase 2
0.6977	Remote Similarity	NPD1592	Phase 3
0.6977	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6220	Phase 3
0.6954	Remote Similarity	NPD2727	Phase 2
0.6952	Remote Similarity	NPD7221	Approved
0.6952	Remote Similarity	NPD3233	Phase 2
0.6952	Remote Similarity	NPD7219	Approved
0.6952	Remote Similarity	NPD3234	Phase 3
0.695	Remote Similarity	NPD6991	Approved
0.6936	Remote Similarity	NPD3717	Discontinued
0.6931	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6026	Approved
0.6923	Remote Similarity	NPD802	Phase 2
0.6923	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7469	Discontinued
0.6906	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6975	Discontinued
0.69	Remote Similarity	NPD6132	Phase 1
0.69	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5596	Phase 2
0.6893	Remote Similarity	NPD2615	Phase 3
0.6893	Remote Similarity	NPD2616	Phase 3
0.6891	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4401	Phase 2
0.6887	Remote Similarity	NPD4403	Phase 3
0.6884	Remote Similarity	NPD484	Approved
0.6884	Remote Similarity	NPD1740	Approved
0.6884	Remote Similarity	NPD1739	Approved
0.6882	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4375	Approved
0.6872	Remote Similarity	NPD3924	Approved
0.6872	Remote Similarity	NPD3923	Approved
0.6872	Remote Similarity	NPD3921	Approved
0.6872	Remote Similarity	NPD3922	Approved
0.6865	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4071	Approved
0.6862	Remote Similarity	NPD4072	Approved
0.6859	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD8063	Discontinued
0.6854	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3477	Phase 2
0.685	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD9690	Approved
0.6842	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8431	Approved
0.6825	Remote Similarity	NPD3417	Phase 1
0.6825	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD4889	Approved
0.6821	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1649	Discontinued
0.6818	Remote Similarity	NPD2952	Discontinued
0.6814	Remote Similarity	NPD5658	Approved
0.6813	Remote Similarity	NPD9705	Discontinued
0.6813	Remote Similarity	NPD112	Approved
0.6811	Remote Similarity	NPD5862	Discovery
0.6811	Remote Similarity	NPD2844	Phase 3
0.6811	Remote Similarity	NPD5021	Discontinued
0.6802	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4600	Approved
0.68	Remote Similarity	NPD4601	Approved
0.68	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3003	Approved
0.6796	Remote Similarity	NPD2582	Approved
0.6796	Remote Similarity	NPD2581	Approved
0.6794	Remote Similarity	NPD7423	Phase 2
0.6794	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5020	Approved
0.678	Remote Similarity	NPD4437	Phase 3
0.6772	Remote Similarity	NPD1032	Phase 2
0.6771	Remote Similarity	NPD4484	Phase 1
0.6768	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7453	Approved
0.6765	Remote Similarity	NPD7452	Approved
0.6757	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4551	Phase 2
0.6751	Remote Similarity	NPD6361	Phase 2
0.6749	Remote Similarity	NPD5901	Discontinued

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