NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	2.858
LogD:	2.561
LogS:	-3.937
# Rotatable Bonds:	0
TPSA:	46.67
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	4.413
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.749
MDCK Permeability:	2.4538081561331637e-05
Pgp-inhibitor:	0.955
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.289
Plasma Protein Binding (PPB):	81.56062316894531%
Volume Distribution (VD):	0.864
Pgp-substrate:	21.86664390563965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.585
CYP2C19-inhibitor:	0.416
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.187
CYP2C9-substrate:	0.557
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.536
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	6.924
Half-life (T1/2):	0.719

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.369
Drug-inuced Liver Injury (DILI):	0.216
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.474
Maximum Recommended Daily Dose:	0.684
Skin Sensitization:	0.941
Carcinogencity:	0.768
Eye Corrosion:	0.199
Eye Irritation:	0.6
Respiratory Toxicity:	0.535

Download Data

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

Natural Product: NPC227814

Natural Product ID:	NPC227814
*Common Name:**	(2R,3S,5R)-2,3-Epoxy-6,9-Humuladien-5-Ol-8-One
IUPAC Name:	(1R,4E,7E,9R,11R)-9-hydroxy-3,3,7,11-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one
Synonyms:
Standard InCHIKey:	RTKZIRJGSBHFAV-VLROITNISA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-10-7-11(16)8-15(4)13(18-15)9-14(2,3)6-5-12(10)17/h5-7,11,13,16H,8-9H2,1-4H3/b6-5+,10-7+/t11-,13+,15+/m0/s1
SMILES:	C/C/1=C[C@@H](C[C@]2(C)[C@@H](CC(C)(C)/C=C/C1=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503727
PubChem CID:	11218910
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols

*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
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1080/10575639708043725]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270556]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	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
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	62500.0	nM	PMID[512141]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	100000.0	nM	PMID[512141]

☑ 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 NPC227814 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	185
0.1-0.2	1326
0.2-0.3	6323
0.3-0.4	16808
0.4-0.5	9730
0.5-0.6	6281
0.6-0.7	1904
0.7-0.8	129
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC144995
0.8382	Intermediate Similarity	NPC228574
0.8382	Intermediate Similarity	NPC294304
0.8289	Intermediate Similarity	NPC476007
0.8077	Intermediate Similarity	NPC136033
0.8026	Intermediate Similarity	NPC474885
0.8	Intermediate Similarity	NPC145963
0.7838	Intermediate Similarity	NPC239373
0.7838	Intermediate Similarity	NPC329989
0.7805	Intermediate Similarity	NPC78673
0.7805	Intermediate Similarity	NPC186155
0.7805	Intermediate Similarity	NPC160517
0.7733	Intermediate Similarity	NPC286154
0.7711	Intermediate Similarity	NPC11804
0.7703	Intermediate Similarity	NPC117804
0.7683	Intermediate Similarity	NPC161045
0.7654	Intermediate Similarity	NPC112868
0.7632	Intermediate Similarity	NPC474884
0.7619	Intermediate Similarity	NPC61527
0.7595	Intermediate Similarity	NPC149550
0.7595	Intermediate Similarity	NPC85105
0.7586	Intermediate Similarity	NPC475441
0.7568	Intermediate Similarity	NPC106613
0.7568	Intermediate Similarity	NPC259299
0.7536	Intermediate Similarity	NPC71755
0.7532	Intermediate Similarity	NPC186042
0.7532	Intermediate Similarity	NPC329763
0.75	Intermediate Similarity	NPC475994
0.75	Intermediate Similarity	NPC231739
0.747	Intermediate Similarity	NPC474809
0.7468	Intermediate Similarity	NPC271070
0.7467	Intermediate Similarity	NPC305698
0.7442	Intermediate Similarity	NPC60765
0.7436	Intermediate Similarity	NPC190859
0.7403	Intermediate Similarity	NPC95863
0.7397	Intermediate Similarity	NPC300593
0.7386	Intermediate Similarity	NPC476705
0.7375	Intermediate Similarity	NPC203403
0.7375	Intermediate Similarity	NPC86917
0.7368	Intermediate Similarity	NPC10758
0.7368	Intermediate Similarity	NPC304690
0.7368	Intermediate Similarity	NPC250928
0.7368	Intermediate Similarity	NPC74722
0.7361	Intermediate Similarity	NPC260573
0.7356	Intermediate Similarity	NPC83423
0.7349	Intermediate Similarity	NPC279186
0.7342	Intermediate Similarity	NPC474011
0.7326	Intermediate Similarity	NPC471738
0.7308	Intermediate Similarity	NPC323437
0.7308	Intermediate Similarity	NPC29542
0.7308	Intermediate Similarity	NPC201562
0.7308	Intermediate Similarity	NPC275098
0.7294	Intermediate Similarity	NPC476426
0.7294	Intermediate Similarity	NPC261380
0.7284	Intermediate Similarity	NPC326753
0.7273	Intermediate Similarity	NPC469660
0.7273	Intermediate Similarity	NPC129630
0.7262	Intermediate Similarity	NPC44261
0.725	Intermediate Similarity	NPC469646
0.725	Intermediate Similarity	NPC477202
0.725	Intermediate Similarity	NPC170148
0.7237	Intermediate Similarity	NPC276290
0.7229	Intermediate Similarity	NPC475944
0.7229	Intermediate Similarity	NPC6663
0.7215	Intermediate Similarity	NPC474545
0.7215	Intermediate Similarity	NPC167049
0.7215	Intermediate Similarity	NPC215050
0.7215	Intermediate Similarity	NPC469691
0.7206	Intermediate Similarity	NPC165755
0.7195	Intermediate Similarity	NPC19900
0.7195	Intermediate Similarity	NPC308038
0.7195	Intermediate Similarity	NPC471537
0.7176	Intermediate Similarity	NPC141193
0.7176	Intermediate Similarity	NPC472326
0.7176	Intermediate Similarity	NPC96259
0.7162	Intermediate Similarity	NPC475221
0.716	Intermediate Similarity	NPC477203
0.716	Intermediate Similarity	NPC262747
0.716	Intermediate Similarity	NPC84360
0.716	Intermediate Similarity	NPC315394
0.716	Intermediate Similarity	NPC476703
0.7158	Intermediate Similarity	NPC473624
0.7143	Intermediate Similarity	NPC214694
0.7143	Intermediate Similarity	NPC477448
0.7143	Intermediate Similarity	NPC477449
0.7143	Intermediate Similarity	NPC259858
0.7143	Intermediate Similarity	NPC158411
0.7143	Intermediate Similarity	NPC85772
0.7143	Intermediate Similarity	NPC93590
0.7143	Intermediate Similarity	NPC38796
0.7126	Intermediate Similarity	NPC72513
0.7125	Intermediate Similarity	NPC469669
0.7125	Intermediate Similarity	NPC329852
0.7125	Intermediate Similarity	NPC475771
0.7125	Intermediate Similarity	NPC469678
0.7123	Intermediate Similarity	NPC475251
0.7111	Intermediate Similarity	NPC125674
0.7111	Intermediate Similarity	NPC475838
0.7111	Intermediate Similarity	NPC228451
0.7108	Intermediate Similarity	NPC470946
0.7108	Intermediate Similarity	NPC470945
0.7108	Intermediate Similarity	NPC470947
0.7108	Intermediate Similarity	NPC471514
0.7105	Intermediate Similarity	NPC269985
0.7105	Intermediate Similarity	NPC96962
0.7093	Intermediate Similarity	NPC471267
0.7093	Intermediate Similarity	NPC28887
0.7093	Intermediate Similarity	NPC96621
0.7093	Intermediate Similarity	NPC165162
0.7083	Intermediate Similarity	NPC475931
0.7083	Intermediate Similarity	NPC122239
0.7079	Intermediate Similarity	NPC3952
0.7079	Intermediate Similarity	NPC473448
0.7079	Intermediate Similarity	NPC469368
0.7073	Intermediate Similarity	NPC209135
0.7073	Intermediate Similarity	NPC474816
0.7073	Intermediate Similarity	NPC192006
0.7073	Intermediate Similarity	NPC279532
0.7073	Intermediate Similarity	NPC62336
0.7067	Intermediate Similarity	NPC474304
0.7067	Intermediate Similarity	NPC474329
0.7067	Intermediate Similarity	NPC308844
0.7059	Intermediate Similarity	NPC472377
0.7059	Intermediate Similarity	NPC477784
0.7059	Intermediate Similarity	NPC477786
0.7059	Intermediate Similarity	NPC311070
0.7059	Intermediate Similarity	NPC477785
0.7059	Intermediate Similarity	NPC79945
0.7051	Intermediate Similarity	NPC4299
0.7045	Intermediate Similarity	NPC476707
0.7045	Intermediate Similarity	NPC476706
0.7037	Intermediate Similarity	NPC263582
0.7037	Intermediate Similarity	NPC250621
0.7037	Intermediate Similarity	NPC268111
0.7037	Intermediate Similarity	NPC469880
0.7033	Intermediate Similarity	NPC474247
0.7033	Intermediate Similarity	NPC167219
0.7027	Intermediate Similarity	NPC217940
0.7027	Intermediate Similarity	NPC473759
0.7027	Intermediate Similarity	NPC474155
0.7024	Intermediate Similarity	NPC470298
0.7024	Intermediate Similarity	NPC325031
0.7024	Intermediate Similarity	NPC474894
0.7024	Intermediate Similarity	NPC315731
0.7024	Intermediate Similarity	NPC470241
0.7013	Intermediate Similarity	NPC471238
0.7013	Intermediate Similarity	NPC45264
0.7013	Intermediate Similarity	NPC167527
0.7011	Intermediate Similarity	NPC475461
0.7011	Intermediate Similarity	NPC281316
0.7011	Intermediate Similarity	NPC122502
0.7011	Intermediate Similarity	NPC194417
0.7011	Intermediate Similarity	NPC472974
0.7011	Intermediate Similarity	NPC305475
0.7	Intermediate Similarity	NPC471525
0.7	Intermediate Similarity	NPC227135
0.7	Intermediate Similarity	NPC158061
0.7	Intermediate Similarity	NPC473675
0.7	Intermediate Similarity	NPC317899
0.7	Intermediate Similarity	NPC160540
0.6989	Remote Similarity	NPC205143
0.6989	Remote Similarity	NPC471916
0.6988	Remote Similarity	NPC325869
0.6988	Remote Similarity	NPC55304
0.6988	Remote Similarity	NPC226226
0.6988	Remote Similarity	NPC139712
0.6988	Remote Similarity	NPC281138
0.6988	Remote Similarity	NPC291260
0.6986	Remote Similarity	NPC99487
0.6986	Remote Similarity	NPC258788
0.6986	Remote Similarity	NPC240506
0.6977	Remote Similarity	NPC474865
0.6977	Remote Similarity	NPC114979
0.6977	Remote Similarity	NPC191476
0.6977	Remote Similarity	NPC7927
0.6977	Remote Similarity	NPC476412
0.6977	Remote Similarity	NPC471301
0.6977	Remote Similarity	NPC31086
0.6977	Remote Similarity	NPC306951
0.6977	Remote Similarity	NPC230527
0.6977	Remote Similarity	NPC40687
0.6974	Remote Similarity	NPC137163
0.6974	Remote Similarity	NPC267027
0.6966	Remote Similarity	NPC170775
0.6966	Remote Similarity	NPC257485
0.6962	Remote Similarity	NPC67076
0.6962	Remote Similarity	NPC471272
0.6962	Remote Similarity	NPC319163
0.6951	Remote Similarity	NPC471061
0.6951	Remote Similarity	NPC474278
0.6951	Remote Similarity	NPC211279
0.6951	Remote Similarity	NPC74995
0.6951	Remote Similarity	NPC233071
0.6951	Remote Similarity	NPC476439
0.6947	Remote Similarity	NPC207885
0.6944	Remote Similarity	NPC181872
0.6944	Remote Similarity	NPC226848
0.6941	Remote Similarity	NPC474291
0.6941	Remote Similarity	NPC471298
0.6933	Remote Similarity	NPC110241

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 NPC227814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1907
0.2-0.3	4170
0.3-0.4	2160
0.4-0.5	466
0.5-0.6	245
0.6-0.7	28
0.7-0.8	3
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
0.7297	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7838	Discovery
0.6897	Remote Similarity	NPD1696	Phase 3
0.6892	Remote Similarity	NPD368	Approved
0.6774	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4820	Approved
0.6706	Remote Similarity	NPD4821	Approved
0.6706	Remote Similarity	NPD4822	Approved
0.6706	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4819	Approved
0.6703	Remote Similarity	NPD5785	Approved
0.6703	Remote Similarity	NPD6698	Approved
0.6703	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7154	Phase 3
0.6598	Remote Similarity	NPD5344	Discontinued
0.6591	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5209	Approved
0.6538	Remote Similarity	NPD7331	Phase 2
0.6517	Remote Similarity	NPD5363	Approved
0.6489	Remote Similarity	NPD5282	Discontinued
0.6471	Remote Similarity	NPD4271	Approved
0.6471	Remote Similarity	NPD4268	Approved
0.6463	Remote Similarity	NPD4732	Discontinued
0.6408	Remote Similarity	NPD6371	Approved
0.6404	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4225	Approved
0.6392	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD6435	Approved
0.6333	Remote Similarity	NPD1694	Approved
0.6327	Remote Similarity	NPD6648	Approved
0.6322	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7332	Phase 2
0.6322	Remote Similarity	NPD7514	Phase 3
0.631	Remote Similarity	NPD8264	Approved
0.6301	Remote Similarity	NPD342	Phase 1
0.6292	Remote Similarity	NPD5362	Discontinued
0.6292	Remote Similarity	NPD6695	Phase 3
0.6279	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7637	Suspended
0.6277	Remote Similarity	NPD7983	Approved
0.6264	Remote Similarity	NPD4249	Approved
0.6264	Remote Similarity	NPD4519	Discontinued
0.6264	Remote Similarity	NPD4623	Approved
0.625	Remote Similarity	NPD6902	Approved
0.6238	Remote Similarity	NPD5141	Approved
0.6234	Remote Similarity	NPD4193	Approved
0.6234	Remote Similarity	NPD4192	Approved
0.6234	Remote Similarity	NPD4191	Approved
0.6234	Remote Similarity	NPD4194	Approved
0.6222	Remote Similarity	NPD3666	Approved
0.6222	Remote Similarity	NPD3665	Phase 1
0.6222	Remote Similarity	NPD3133	Approved
0.6216	Remote Similarity	NPD4219	Approved
0.6207	Remote Similarity	NPD4195	Approved
0.6204	Remote Similarity	NPD7115	Discovery
0.6196	Remote Similarity	NPD4251	Approved
0.6196	Remote Similarity	NPD4250	Approved
0.618	Remote Similarity	NPD4270	Approved
0.618	Remote Similarity	NPD4269	Approved
0.6162	Remote Similarity	NPD5286	Approved
0.6162	Remote Similarity	NPD4696	Approved
0.6162	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6931	Approved
0.6136	Remote Similarity	NPD6930	Phase 2
0.6136	Remote Similarity	NPD5368	Approved
0.6118	Remote Similarity	NPD8039	Approved
0.6117	Remote Similarity	NPD5697	Approved
0.6111	Remote Similarity	NPD5332	Approved
0.6111	Remote Similarity	NPD5331	Approved
0.6105	Remote Similarity	NPD6079	Approved
0.6104	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7145	Approved
0.6087	Remote Similarity	NPD5786	Approved
0.6087	Remote Similarity	NPD5279	Phase 3
0.6087	Remote Similarity	NPD3618	Phase 1
0.6082	Remote Similarity	NPD5210	Approved
0.6082	Remote Similarity	NPD4629	Approved
0.6067	Remote Similarity	NPD4790	Discontinued
0.6067	Remote Similarity	NPD5369	Approved
0.6064	Remote Similarity	NPD1695	Approved
0.6064	Remote Similarity	NPD4753	Phase 2
0.6058	Remote Similarity	NPD6899	Approved
0.6058	Remote Similarity	NPD6881	Approved
0.6042	Remote Similarity	NPD5779	Approved
0.6042	Remote Similarity	NPD5778	Approved
0.6042	Remote Similarity	NPD4202	Approved
0.604	Remote Similarity	NPD5224	Approved
0.604	Remote Similarity	NPD5226	Approved
0.604	Remote Similarity	NPD5225	Approved
0.604	Remote Similarity	NPD4633	Approved
0.6023	Remote Similarity	NPD6929	Approved
0.6022	Remote Similarity	NPD7750	Discontinued
0.6022	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD7341	Phase 2
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD6926	Approved
0.6	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD6924	Approved
0.6	Remote Similarity	NPD6012	Approved
0.598	Remote Similarity	NPD5174	Approved
0.598	Remote Similarity	NPD5175	Approved
0.5977	Remote Similarity	NPD5776	Phase 2
0.5977	Remote Similarity	NPD6925	Approved
0.5977	Remote Similarity	NPD4756	Discovery
0.5977	Remote Similarity	NPD6932	Approved
0.596	Remote Similarity	NPD4755	Approved
0.596	Remote Similarity	NPD6083	Phase 2
0.596	Remote Similarity	NPD6084	Phase 2
0.5955	Remote Similarity	NPD4695	Discontinued
0.5955	Remote Similarity	NPD4252	Approved
0.5943	Remote Similarity	NPD7102	Approved
0.5943	Remote Similarity	NPD7290	Approved
0.5943	Remote Similarity	NPD6883	Approved
0.5941	Remote Similarity	NPD5223	Approved
0.5938	Remote Similarity	NPD6411	Approved
0.5934	Remote Similarity	NPD6110	Phase 1
0.5918	Remote Similarity	NPD5695	Phase 3
0.5914	Remote Similarity	NPD5690	Phase 2
0.5905	Remote Similarity	NPD6686	Approved
0.5905	Remote Similarity	NPD6011	Approved
0.59	Remote Similarity	NPD7638	Approved
0.5895	Remote Similarity	NPD5328	Approved
0.5889	Remote Similarity	NPD6898	Phase 1
0.5888	Remote Similarity	NPD8130	Phase 1
0.5888	Remote Similarity	NPD6847	Approved
0.5888	Remote Similarity	NPD6617	Approved
0.5888	Remote Similarity	NPD6649	Approved
0.5888	Remote Similarity	NPD6869	Approved
0.5888	Remote Similarity	NPD6650	Approved
0.5875	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4786	Approved
0.5865	Remote Similarity	NPD7128	Approved
0.5865	Remote Similarity	NPD6402	Approved
0.5865	Remote Similarity	NPD6675	Approved
0.5865	Remote Similarity	NPD5739	Approved
0.5862	Remote Similarity	NPD6933	Approved
0.5859	Remote Similarity	NPD5221	Approved
0.5859	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5222	Approved
0.5859	Remote Similarity	NPD7839	Suspended
0.5844	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD7645	Phase 2
0.5842	Remote Similarity	NPD4700	Approved
0.5833	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD7144	Approved
0.5833	Remote Similarity	NPD6882	Approved
0.5833	Remote Similarity	NPD7143	Approved
0.5825	Remote Similarity	NPD6647	Phase 2
0.5824	Remote Similarity	NPD4221	Approved
0.5824	Remote Similarity	NPD4223	Phase 3
0.5816	Remote Similarity	NPD7748	Approved
0.581	Remote Similarity	NPD5701	Approved
0.5806	Remote Similarity	NPD6893	Approved
0.58	Remote Similarity	NPD5173	Approved
0.58	Remote Similarity	NPD7902	Approved
0.5778	Remote Similarity	NPD7509	Discontinued
0.5778	Remote Similarity	NPD7525	Registered
0.5773	Remote Similarity	NPD7087	Discontinued
0.5773	Remote Similarity	NPD7515	Phase 2
0.5765	Remote Similarity	NPD7150	Approved
0.5765	Remote Similarity	NPD7151	Approved
0.5765	Remote Similarity	NPD7152	Approved
0.5755	Remote Similarity	NPD4729	Approved
0.5755	Remote Similarity	NPD4730	Approved
0.5755	Remote Similarity	NPD7320	Approved
0.575	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5330	Approved
0.5745	Remote Similarity	NPD7521	Approved
0.5745	Remote Similarity	NPD6409	Approved
0.5745	Remote Similarity	NPD7146	Approved
0.5745	Remote Similarity	NPD7334	Approved
0.5745	Remote Similarity	NPD6684	Approved
0.5743	Remote Similarity	NPD5696	Approved
0.5732	Remote Similarity	NPD3704	Approved
0.5732	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5370	Suspended
0.5729	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6101	Approved
0.5714	Remote Similarity	NPD6922	Approved
0.5714	Remote Similarity	NPD4265	Approved
0.5714	Remote Similarity	NPD6923	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5701	Remote Similarity	NPD6372	Approved
0.5701	Remote Similarity	NPD6373	Approved
0.5701	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD4197	Approved
0.5684	Remote Similarity	NPD3573	Approved
0.5684	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD819	Approved
0.5682	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD818	Approved
0.5679	Remote Similarity	NPD3197	Phase 1

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