NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	1.932
LogD:	1.658
LogS:	-3.194
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	4.476
Fsp3:	0.667
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:	-4.62
MDCK Permeability:	1.4785809071327094e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.199
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.159
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.868
Plasma Protein Binding (PPB):	72.35298156738281%
Volume Distribution (VD):	1.198
Pgp-substrate:	22.55270767211914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.373
CYP2C19-inhibitor:	0.134
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	5.905
Half-life (T1/2):	0.365

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.521
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.6
Skin Sensitization:	0.871
Carcinogencity:	0.976
Eye Corrosion:	0.316
Eye Irritation:	0.473
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC30675

Natural Product ID:	NPC30675
*Common Name:**	Procurcumadiol
IUPAC Name:	(3S,3aR,8aS)-3,3a-dihydroxy-3,8-dimethyl-5-propan-2-ylidene-1,2,4,8a-tetrahydroazulen-6-one
Synonyms:
Standard InCHIKey:	MBUWIGIPGMJVMN-AEGPPILISA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9(2)11-8-15(18)12(5-6-14(15,4)17)10(3)7-13(11)16/h7,12,17-18H,5-6,8H2,1-4H3/t12-,14-,15+/m0/s1
SMILES:	CC1=CC(=O)C(=C(C)C)C[C@]2([C@H]1CC[C@]2(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386512
PubChem CID:	14633012
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002874] Guaianes

*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
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24124	Curcuma longa	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	11700.0	nM	PMID[536139]

☑ 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 NPC30675 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	183
0.1-0.2	1467
0.2-0.3	7779
0.3-0.4	16956
0.4-0.5	8929
0.5-0.6	5715
0.6-0.7	1584
0.7-0.8	63
0.8-0.85	17
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9054	High Similarity	NPC300940
0.8667	High Similarity	NPC469737
0.8519	High Similarity	NPC133844
0.8375	Intermediate Similarity	NPC66677
0.8375	Intermediate Similarity	NPC471890
0.8375	Intermediate Similarity	NPC84185
0.8333	Intermediate Similarity	NPC77501
0.8272	Intermediate Similarity	NPC164218
0.8228	Intermediate Similarity	NPC142759
0.8228	Intermediate Similarity	NPC115719
0.8228	Intermediate Similarity	NPC473437
0.8228	Intermediate Similarity	NPC25908
0.8228	Intermediate Similarity	NPC141346
0.8228	Intermediate Similarity	NPC124289
0.8101	Intermediate Similarity	NPC251435
0.7831	Intermediate Similarity	NPC476625
0.7692	Intermediate Similarity	NPC298919
0.7683	Intermediate Similarity	NPC276769
0.7674	Intermediate Similarity	NPC90446
0.7654	Intermediate Similarity	NPC89374
0.7632	Intermediate Similarity	NPC469326
0.7632	Intermediate Similarity	NPC205618
0.7632	Intermediate Similarity	NPC261782
0.7595	Intermediate Similarity	NPC471781
0.7586	Intermediate Similarity	NPC476628
0.7561	Intermediate Similarity	NPC215481
0.7529	Intermediate Similarity	NPC171665
0.75	Intermediate Similarity	NPC41886
0.75	Intermediate Similarity	NPC261125
0.75	Intermediate Similarity	NPC181195
0.75	Intermediate Similarity	NPC70369
0.7432	Intermediate Similarity	NPC469321
0.7412	Intermediate Similarity	NPC470945
0.7412	Intermediate Similarity	NPC470947
0.7412	Intermediate Similarity	NPC470946
0.7381	Intermediate Similarity	NPC19443
0.7375	Intermediate Similarity	NPC280256
0.7363	Intermediate Similarity	NPC37607
0.7363	Intermediate Similarity	NPC301969
0.7349	Intermediate Similarity	NPC469646
0.7317	Intermediate Similarity	NPC7382
0.7308	Intermediate Similarity	NPC197089
0.7262	Intermediate Similarity	NPC472014
0.7253	Intermediate Similarity	NPC41217
0.725	Intermediate Similarity	NPC144647
0.725	Intermediate Similarity	NPC469914
0.7241	Intermediate Similarity	NPC193347
0.7237	Intermediate Similarity	NPC63111
0.7216	Intermediate Similarity	NPC471401
0.7216	Intermediate Similarity	NPC150923
0.7204	Intermediate Similarity	NPC125180
0.7191	Intermediate Similarity	NPC36350
0.7188	Intermediate Similarity	NPC470541
0.7174	Intermediate Similarity	NPC2946
0.7143	Intermediate Similarity	NPC472677
0.7143	Intermediate Similarity	NPC58532
0.7143	Intermediate Similarity	NPC126969
0.7111	Intermediate Similarity	NPC67493
0.71	Intermediate Similarity	NPC149047
0.7097	Intermediate Similarity	NPC144629
0.7083	Intermediate Similarity	NPC477267
0.7083	Intermediate Similarity	NPC472689
0.7083	Intermediate Similarity	NPC472690
0.7083	Intermediate Similarity	NPC477268
0.7079	Intermediate Similarity	NPC7927
0.7079	Intermediate Similarity	NPC230527
0.7079	Intermediate Similarity	NPC144258
0.7079	Intermediate Similarity	NPC472957
0.7079	Intermediate Similarity	NPC472958
0.7073	Intermediate Similarity	NPC29328
0.7073	Intermediate Similarity	NPC144627
0.7065	Intermediate Similarity	NPC232747
0.7065	Intermediate Similarity	NPC97032
0.7053	Intermediate Similarity	NPC52044
0.7053	Intermediate Similarity	NPC261341
0.7053	Intermediate Similarity	NPC67584
0.7045	Intermediate Similarity	NPC256750
0.7045	Intermediate Similarity	NPC20262
0.703	Intermediate Similarity	NPC220229
0.703	Intermediate Similarity	NPC475060
0.7024	Intermediate Similarity	NPC474011
0.7011	Intermediate Similarity	NPC258965
0.7011	Intermediate Similarity	NPC156658
0.7	Intermediate Similarity	NPC60120
0.7	Intermediate Similarity	NPC476626
0.7	Intermediate Similarity	NPC204833
0.7	Intermediate Similarity	NPC209502
0.7	Intermediate Similarity	NPC142649
0.6989	Remote Similarity	NPC477711
0.6979	Remote Similarity	NPC8803
0.6979	Remote Similarity	NPC213078
0.6977	Remote Similarity	NPC222210
0.6977	Remote Similarity	NPC63445
0.6977	Remote Similarity	NPC476627
0.6974	Remote Similarity	NPC143834
0.6966	Remote Similarity	NPC62214
0.6962	Remote Similarity	NPC474329
0.6962	Remote Similarity	NPC474304
0.6962	Remote Similarity	NPC61473
0.6961	Remote Similarity	NPC117604
0.6961	Remote Similarity	NPC217201
0.6957	Remote Similarity	NPC471941
0.6957	Remote Similarity	NPC477710
0.6957	Remote Similarity	NPC320665
0.6957	Remote Similarity	NPC91248
0.6957	Remote Similarity	NPC476708
0.6941	Remote Similarity	NPC226242
0.6939	Remote Similarity	NPC474720
0.6939	Remote Similarity	NPC280963
0.6933	Remote Similarity	NPC278550
0.6932	Remote Similarity	NPC136150
0.6931	Remote Similarity	NPC214264
0.6931	Remote Similarity	NPC150531
0.6931	Remote Similarity	NPC202167
0.6931	Remote Similarity	NPC260268
0.6931	Remote Similarity	NPC54737
0.6931	Remote Similarity	NPC48733
0.6931	Remote Similarity	NPC85829
0.6931	Remote Similarity	NPC319077
0.6931	Remote Similarity	NPC49958
0.6931	Remote Similarity	NPC296945
0.6931	Remote Similarity	NPC171137
0.6931	Remote Similarity	NPC302607
0.6931	Remote Similarity	NPC152695
0.6931	Remote Similarity	NPC476027
0.6931	Remote Similarity	NPC97202
0.6931	Remote Similarity	NPC50692
0.6931	Remote Similarity	NPC190867
0.6923	Remote Similarity	NPC6247
0.6923	Remote Similarity	NPC232156
0.6914	Remote Similarity	NPC476614
0.6907	Remote Similarity	NPC161493
0.6907	Remote Similarity	NPC87090
0.6905	Remote Similarity	NPC206875
0.69	Remote Similarity	NPC124881
0.69	Remote Similarity	NPC191892
0.6897	Remote Similarity	NPC164308
0.6897	Remote Similarity	NPC472013
0.6897	Remote Similarity	NPC476624
0.6893	Remote Similarity	NPC11710
0.6893	Remote Similarity	NPC471400
0.6889	Remote Similarity	NPC475796
0.6889	Remote Similarity	NPC165287
0.6889	Remote Similarity	NPC472480
0.6889	Remote Similarity	NPC156485
0.6882	Remote Similarity	NPC186688
0.6882	Remote Similarity	NPC477943
0.6882	Remote Similarity	NPC170775
0.6875	Remote Similarity	NPC472824
0.6869	Remote Similarity	NPC206079
0.6869	Remote Similarity	NPC237190
0.6867	Remote Similarity	NPC288667
0.6867	Remote Similarity	NPC106309
0.6863	Remote Similarity	NPC83744
0.6863	Remote Similarity	NPC43285
0.6863	Remote Similarity	NPC477916
0.6863	Remote Similarity	NPC58370
0.686	Remote Similarity	NPC15975
0.686	Remote Similarity	NPC195785
0.686	Remote Similarity	NPC103987
0.686	Remote Similarity	NPC53581
0.6848	Remote Similarity	NPC237540
0.6842	Remote Similarity	NPC135776
0.6837	Remote Similarity	NPC244411
0.6837	Remote Similarity	NPC109556
0.6837	Remote Similarity	NPC221615
0.6837	Remote Similarity	NPC477355
0.6832	Remote Similarity	NPC100487
0.6829	Remote Similarity	NPC250928
0.6829	Remote Similarity	NPC10758
0.6824	Remote Similarity	NPC201263
0.6824	Remote Similarity	NPC472256
0.6824	Remote Similarity	NPC114236
0.6818	Remote Similarity	NPC472948
0.6818	Remote Similarity	NPC233352
0.6818	Remote Similarity	NPC824
0.6818	Remote Similarity	NPC138492
0.6818	Remote Similarity	NPC47747
0.6813	Remote Similarity	NPC287015
0.6813	Remote Similarity	NPC204105
0.6813	Remote Similarity	NPC469948
0.6813	Remote Similarity	NPC146850
0.6813	Remote Similarity	NPC132629
0.6813	Remote Similarity	NPC15838
0.6813	Remote Similarity	NPC300082
0.6813	Remote Similarity	NPC284534
0.6804	Remote Similarity	NPC49371
0.68	Remote Similarity	NPC477915
0.68	Remote Similarity	NPC473424
0.6796	Remote Similarity	NPC329417
0.6796	Remote Similarity	NPC65941
0.6782	Remote Similarity	NPC474056
0.6778	Remote Similarity	NPC470165
0.6778	Remote Similarity	NPC476082
0.6778	Remote Similarity	NPC65350
0.6778	Remote Similarity	NPC278648
0.6774	Remote Similarity	NPC476706
0.6774	Remote Similarity	NPC476704
0.6774	Remote Similarity	NPC476707
0.6774	Remote Similarity	NPC178875

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 NPC30675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	2298
0.2-0.3	4326
0.3-0.4	1660
0.4-0.5	375
0.5-0.6	234
0.6-0.7	75
0.7-0.8	2
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
0.7308	Intermediate Similarity	NPD7331	Phase 2
0.7241	Intermediate Similarity	NPD4223	Phase 3
0.7241	Intermediate Similarity	NPD4221	Approved
0.7079	Intermediate Similarity	NPD4197	Approved
0.7045	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5329	Approved
0.6962	Remote Similarity	NPD7341	Phase 2
0.6957	Remote Similarity	NPD4518	Approved
0.6932	Remote Similarity	NPD5369	Approved
0.6923	Remote Similarity	NPD4694	Approved
0.6923	Remote Similarity	NPD4690	Approved
0.6923	Remote Similarity	NPD4689	Approved
0.6923	Remote Similarity	NPD5280	Approved
0.6923	Remote Similarity	NPD4688	Approved
0.6923	Remote Similarity	NPD5690	Phase 2
0.6923	Remote Similarity	NPD5205	Approved
0.6923	Remote Similarity	NPD4138	Approved
0.6923	Remote Similarity	NPD4693	Phase 3
0.6818	Remote Similarity	NPD5368	Approved
0.6813	Remote Similarity	NPD5363	Approved
0.6739	Remote Similarity	NPD5786	Approved
0.6737	Remote Similarity	NPD5284	Approved
0.6737	Remote Similarity	NPD5281	Approved
0.6703	Remote Similarity	NPD3665	Phase 1
0.6703	Remote Similarity	NPD3133	Approved
0.6703	Remote Similarity	NPD3666	Approved
0.6702	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6632	Remote Similarity	NPD4096	Approved
0.6593	Remote Similarity	NPD5362	Discontinued
0.6566	Remote Similarity	NPD4755	Approved
0.6559	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4629	Approved
0.6531	Remote Similarity	NPD5210	Approved
0.6526	Remote Similarity	NPD5328	Approved
0.6517	Remote Similarity	NPD4195	Approved
0.6509	Remote Similarity	NPD6371	Approved
0.6495	Remote Similarity	NPD4202	Approved
0.6458	Remote Similarity	NPD5785	Approved
0.6444	Remote Similarity	NPD4252	Approved
0.6436	Remote Similarity	NPD4696	Approved
0.6436	Remote Similarity	NPD5285	Approved
0.6436	Remote Similarity	NPD5286	Approved
0.6436	Remote Similarity	NPD4700	Approved
0.6392	Remote Similarity	NPD6079	Approved
0.6383	Remote Similarity	NPD5279	Phase 3
0.6383	Remote Similarity	NPD3618	Phase 1
0.6381	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4139	Approved
0.6374	Remote Similarity	NPD4692	Approved
0.6373	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6354	Remote Similarity	NPD1695	Approved
0.6344	Remote Similarity	NPD4786	Approved
0.6337	Remote Similarity	NPD5696	Approved
0.633	Remote Similarity	NPD4632	Approved
0.6327	Remote Similarity	NPD5133	Approved
0.6311	Remote Similarity	NPD5226	Approved
0.6311	Remote Similarity	NPD5225	Approved
0.6311	Remote Similarity	NPD5224	Approved
0.6311	Remote Similarity	NPD4633	Approved
0.6311	Remote Similarity	NPD5211	Phase 2
0.6304	Remote Similarity	NPD3667	Approved
0.63	Remote Similarity	NPD4697	Phase 3
0.6289	Remote Similarity	NPD5207	Approved
0.6286	Remote Similarity	NPD6008	Approved
0.6277	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4821	Approved
0.6264	Remote Similarity	NPD4819	Approved
0.6264	Remote Similarity	NPD4695	Discontinued
0.6264	Remote Similarity	NPD4822	Approved
0.6264	Remote Similarity	NPD4820	Approved
0.6263	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD4754	Approved
0.625	Remote Similarity	NPD5175	Approved
0.625	Remote Similarity	NPD5174	Approved
0.6239	Remote Similarity	NPD6053	Discontinued
0.6238	Remote Similarity	NPD6084	Phase 2
0.6238	Remote Similarity	NPD6083	Phase 2
0.6237	Remote Similarity	NPD4788	Approved
0.6237	Remote Similarity	NPD5331	Approved
0.6237	Remote Similarity	NPD5332	Approved
0.6222	Remote Similarity	NPD3617	Approved
0.6222	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.62	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4790	Discontinued
0.619	Remote Similarity	NPD5141	Approved
0.6186	Remote Similarity	NPD6080	Approved
0.6186	Remote Similarity	NPD6904	Approved
0.6186	Remote Similarity	NPD6673	Approved
0.6163	Remote Similarity	NPD4747	Approved
0.6154	Remote Similarity	NPD5091	Approved
0.614	Remote Similarity	NPD6319	Approved
0.6139	Remote Similarity	NPD5222	Approved
0.6139	Remote Similarity	NPD5221	Approved
0.6139	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6675	Approved
0.6132	Remote Similarity	NPD7128	Approved
0.6132	Remote Similarity	NPD5739	Approved
0.6132	Remote Similarity	NPD4768	Approved
0.6132	Remote Similarity	NPD6402	Approved
0.6132	Remote Similarity	NPD4767	Approved
0.6122	Remote Similarity	NPD5692	Phase 3
0.6111	Remote Similarity	NPD6372	Approved
0.6111	Remote Similarity	NPD6373	Approved
0.61	Remote Similarity	NPD6001	Approved
0.6098	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD5276	Approved
0.6078	Remote Similarity	NPD5173	Approved
0.6075	Remote Similarity	NPD5701	Approved
0.6075	Remote Similarity	NPD5697	Approved
0.6075	Remote Similarity	NPD6412	Phase 2
0.6061	Remote Similarity	NPD5694	Approved
0.6061	Remote Similarity	NPD6050	Approved
0.6061	Remote Similarity	NPD5693	Phase 1
0.6047	Remote Similarity	NPD4137	Phase 3
0.6044	Remote Similarity	NPD4271	Approved
0.6044	Remote Similarity	NPD4268	Approved
0.6042	Remote Similarity	NPD7334	Approved
0.6042	Remote Similarity	NPD6409	Approved
0.6042	Remote Similarity	NPD5330	Approved
0.6042	Remote Similarity	NPD7146	Approved
0.6042	Remote Similarity	NPD6098	Approved
0.6042	Remote Similarity	NPD6684	Approved
0.6042	Remote Similarity	NPD7521	Approved
0.6042	Remote Similarity	NPD4623	Approved
0.6042	Remote Similarity	NPD4519	Discontinued
0.604	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5128	Approved
0.6019	Remote Similarity	NPD7320	Approved
0.6019	Remote Similarity	NPD6011	Approved
0.6019	Remote Similarity	NPD6881	Approved
0.6019	Remote Similarity	NPD6899	Approved
0.6019	Remote Similarity	NPD4729	Approved
0.6019	Remote Similarity	NPD4730	Approved
0.6018	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6933	Approved
0.6	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5977	Remote Similarity	NPD4691	Approved
0.5963	Remote Similarity	NPD6012	Approved
0.5963	Remote Similarity	NPD6013	Approved
0.5963	Remote Similarity	NPD6014	Approved
0.596	Remote Similarity	NPD6698	Approved
0.596	Remote Similarity	NPD46	Approved
0.5955	Remote Similarity	NPD4785	Approved
0.5955	Remote Similarity	NPD5733	Approved
0.5955	Remote Similarity	NPD4687	Approved
0.5955	Remote Similarity	NPD4784	Approved
0.5948	Remote Similarity	NPD6016	Approved
0.5948	Remote Similarity	NPD6015	Approved
0.5946	Remote Similarity	NPD8297	Approved
0.5938	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6903	Approved
0.5918	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD4522	Approved
0.5909	Remote Similarity	NPD5135	Approved
0.5909	Remote Similarity	NPD5251	Approved
0.5909	Remote Similarity	NPD6883	Approved
0.5909	Remote Similarity	NPD4243	Approved
0.5909	Remote Similarity	NPD5247	Approved
0.5909	Remote Similarity	NPD7102	Approved
0.5909	Remote Similarity	NPD5248	Approved
0.5909	Remote Similarity	NPD5169	Approved
0.5909	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5249	Phase 3
0.5909	Remote Similarity	NPD5250	Approved
0.5909	Remote Similarity	NPD7290	Approved
0.59	Remote Similarity	NPD7983	Approved
0.5897	Remote Similarity	NPD6370	Approved
0.5897	Remote Similarity	NPD5988	Approved
0.5895	Remote Similarity	NPD7154	Phase 3
0.5895	Remote Similarity	NPD6110	Phase 1
0.5876	Remote Similarity	NPD4249	Approved
0.5856	Remote Similarity	NPD5127	Approved
0.5856	Remote Similarity	NPD6869	Approved
0.5856	Remote Similarity	NPD8130	Phase 1
0.5856	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6617	Approved
0.5856	Remote Similarity	NPD5217	Approved
0.5856	Remote Similarity	NPD5216	Approved
0.5856	Remote Similarity	NPD5215	Approved
0.5856	Remote Similarity	NPD6847	Approved
0.5833	Remote Similarity	NPD3668	Phase 3
0.5816	Remote Similarity	NPD4250	Approved
0.5816	Remote Similarity	NPD4251	Approved
0.5812	Remote Similarity	NPD5983	Phase 2
0.5804	Remote Similarity	NPD6882	Approved
0.5798	Remote Similarity	NPD7492	Approved
0.5778	Remote Similarity	NPD4058	Approved
0.5778	Remote Similarity	NPD6926	Approved
0.5778	Remote Similarity	NPD6924	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