NPASS Compound

Structure

NPC472838 OpenBabel07101719512D 25 28 0 0 0 0 0 0 0 0999 V2000 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6825 4.0814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 2.5981 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 1.5243 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -2.2395 2.2930 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1055 2.7930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7517 3.7160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 14 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 23 2 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.1
Volume:	346.343
LogP:	4.179
LogD:	3.483
LogS:	-5.424
# Rotatable Bonds:	3
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	2.557
Fsp3:	0.095
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.061
MDCK Permeability:	1.7210448277182877e-05
Pgp-inhibitor:	0.945
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.131
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.119
Plasma Protein Binding (PPB):	99.11583709716797%
Volume Distribution (VD):	0.421
Pgp-substrate:	1.028398036956787%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.752
CYP2D6-substrate:	0.731
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	3.953
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.437
Human Hepatotoxicity (H-HT):	0.802
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.903
Rat Oral Acute Toxicity:	0.355
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.922
Carcinogencity:	0.905
Eye Corrosion:	0.004
Eye Irritation:	0.553
Respiratory Toxicity:	0.862

Download Data

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

Natural Product: NPC472838

Natural Product ID:	NPC472838
*Common Name:**	5-Hydroxy-2,6-Dimethoxy-9-Phenylphenalen-1-One
IUPAC Name:	5-hydroxy-2,6-dimethoxy-9-phenylphenalen-1-one
Synonyms:
Standard InCHIKey:	PMDWWXHMCLGWNY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H16O4/c1-24-17-11-13-10-16(22)21(25-2)15-9-8-14(12-6-4-3-5-7-12)19(18(13)15)20(17)23/h3-11,22H,1-2H3
SMILES:	COC1=CC2=CC(=C(C3=C2C(=C(C=C3)C4=CC=CC=C4)C1=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3589050
PubChem CID:	73212250
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002044] Phenylnaphthalenes

*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
NPO32893	haemodorum spicatum	Species	Haemodoraceae	Eukaryota	n.a.	Australian	n.a.	PMID[26090896]

☑ 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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	1.0	mm	PMID[465821]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	1.0	mm	PMID[465821]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	1.0	mm	PMID[465821]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	IZ	=	1.0	mm	PMID[465821]

☑ 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 NPC472838 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	407
0.1-0.2	1830
0.2-0.3	4154
0.3-0.4	11333
0.4-0.5	6649
0.5-0.6	3812
0.6-0.7	7030
0.7-0.8	6693
0.8-0.85	700
0.85-0.9	71
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC306011
0.9793	High Similarity	NPC58310
0.9793	High Similarity	NPC295977
0.9597	High Similarity	NPC288353
0.9586	High Similarity	NPC58373
0.9514	High Similarity	NPC472836
0.9252	High Similarity	NPC39361
0.92	High Similarity	NPC144283
0.9195	High Similarity	NPC472837
0.9128	High Similarity	NPC472839
0.9116	High Similarity	NPC91694
0.9116	High Similarity	NPC300603
0.911	High Similarity	NPC192597
0.911	High Similarity	NPC176030
0.911	High Similarity	NPC169214
0.911	High Similarity	NPC229218
0.911	High Similarity	NPC141817
0.9091	High Similarity	NPC104876
0.9091	High Similarity	NPC245891
0.9085	High Similarity	NPC213401
0.9085	High Similarity	NPC279605
0.9028	High Similarity	NPC186647
0.9013	High Similarity	NPC164912
0.9007	High Similarity	NPC475718
0.8986	High Similarity	NPC309169
0.8986	High Similarity	NPC196941
0.8947	High Similarity	NPC302783
0.8947	High Similarity	NPC473201
0.8947	High Similarity	NPC118427
0.8933	High Similarity	NPC52692
0.8926	High Similarity	NPC73416
0.8926	High Similarity	NPC160777
0.8924	High Similarity	NPC26386
0.8903	High Similarity	NPC167098
0.8903	High Similarity	NPC296044
0.8897	High Similarity	NPC264022
0.8889	High Similarity	NPC137125
0.8889	High Similarity	NPC3744
0.8874	High Similarity	NPC474556
0.8859	High Similarity	NPC308006
0.8824	High Similarity	NPC78505
0.8824	High Similarity	NPC70320
0.8816	High Similarity	NPC261322
0.88	High Similarity	NPC225351
0.8792	High Similarity	NPC50954
0.878	High Similarity	NPC47191
0.8759	High Similarity	NPC22644
0.875	High Similarity	NPC472841
0.8725	High Similarity	NPC11314
0.8725	High Similarity	NPC201297
0.8701	High Similarity	NPC474414
0.8679	High Similarity	NPC149389
0.8679	High Similarity	NPC469472
0.8662	High Similarity	NPC178976
0.8662	High Similarity	NPC199463
0.8662	High Similarity	NPC37543
0.8658	High Similarity	NPC84273
0.8654	High Similarity	NPC478161
0.8654	High Similarity	NPC478159
0.8654	High Similarity	NPC268008
0.8649	High Similarity	NPC470407
0.863	High Similarity	NPC88065
0.863	High Similarity	NPC89504
0.863	High Similarity	NPC95485
0.8616	High Similarity	NPC318081
0.86	High Similarity	NPC69755
0.8599	High Similarity	NPC77807
0.8599	High Similarity	NPC14561
0.8599	High Similarity	NPC5379
0.8581	High Similarity	NPC75377
0.858	High Similarity	NPC469521
0.8571	High Similarity	NPC471670
0.8571	High Similarity	NPC80370
0.8553	High Similarity	NPC157133
0.8552	High Similarity	NPC239302
0.8552	High Similarity	NPC183103
0.8544	High Similarity	NPC143328
0.8542	High Similarity	NPC66905
0.8542	High Similarity	NPC172673
0.8526	High Similarity	NPC312338
0.8526	High Similarity	NPC149889
0.8523	High Similarity	NPC223336
0.8519	High Similarity	NPC263212
0.85	High Similarity	NPC131905
0.85	High Similarity	NPC311740
0.8493	Intermediate Similarity	NPC470406
0.8487	Intermediate Similarity	NPC275278
0.8481	Intermediate Similarity	NPC109765
0.8471	Intermediate Similarity	NPC107109
0.8471	Intermediate Similarity	NPC93552
0.8467	Intermediate Similarity	NPC78987
0.8467	Intermediate Similarity	NPC82336
0.8462	Intermediate Similarity	NPC230848
0.8462	Intermediate Similarity	NPC124842
0.8457	Intermediate Similarity	NPC303174
0.8456	Intermediate Similarity	NPC284409
0.8452	Intermediate Similarity	NPC237441
0.8452	Intermediate Similarity	NPC300983
0.8442	Intermediate Similarity	NPC77598
0.8442	Intermediate Similarity	NPC478163
0.8438	Intermediate Similarity	NPC84571
0.8428	Intermediate Similarity	NPC202495
0.8421	Intermediate Similarity	NPC224884
0.8421	Intermediate Similarity	NPC209085
0.8414	Intermediate Similarity	NPC27659
0.8411	Intermediate Similarity	NPC472410
0.8389	Intermediate Similarity	NPC290601
0.8383	Intermediate Similarity	NPC49667
0.8383	Intermediate Similarity	NPC8127
0.8378	Intermediate Similarity	NPC152209
0.8378	Intermediate Similarity	NPC153088
0.8375	Intermediate Similarity	NPC477410
0.8366	Intermediate Similarity	NPC105213
0.8366	Intermediate Similarity	NPC207732
0.8365	Intermediate Similarity	NPC478223
0.8354	Intermediate Similarity	NPC62051
0.8354	Intermediate Similarity	NPC127172
0.8354	Intermediate Similarity	NPC305710
0.8345	Intermediate Similarity	NPC304622
0.8344	Intermediate Similarity	NPC256406
0.8344	Intermediate Similarity	NPC115869
0.8344	Intermediate Similarity	NPC272566
0.8333	Intermediate Similarity	NPC5018
0.8333	Intermediate Similarity	NPC37220
0.8333	Intermediate Similarity	NPC123228
0.8333	Intermediate Similarity	NPC428300
0.8333	Intermediate Similarity	NPC276466
0.8333	Intermediate Similarity	NPC230811
0.8333	Intermediate Similarity	NPC475104
0.8333	Intermediate Similarity	NPC123722
0.8333	Intermediate Similarity	NPC151167
0.8323	Intermediate Similarity	NPC245975
0.8323	Intermediate Similarity	NPC141574
0.8323	Intermediate Similarity	NPC185617
0.8322	Intermediate Similarity	NPC324929
0.8314	Intermediate Similarity	NPC205721
0.8313	Intermediate Similarity	NPC473113
0.8313	Intermediate Similarity	NPC35598
0.8313	Intermediate Similarity	NPC4200
0.8313	Intermediate Similarity	NPC222689
0.8312	Intermediate Similarity	NPC478160
0.8312	Intermediate Similarity	NPC478019
0.8303	Intermediate Similarity	NPC188079
0.8302	Intermediate Similarity	NPC66508
0.8302	Intermediate Similarity	NPC80489
0.8302	Intermediate Similarity	NPC472835
0.8302	Intermediate Similarity	NPC234485
0.8302	Intermediate Similarity	NPC226656
0.8301	Intermediate Similarity	NPC53016
0.8301	Intermediate Similarity	NPC16353
0.8301	Intermediate Similarity	NPC46161
0.8301	Intermediate Similarity	NPC239608
0.8301	Intermediate Similarity	NPC46880
0.8299	Intermediate Similarity	NPC228843
0.8299	Intermediate Similarity	NPC312560
0.8293	Intermediate Similarity	NPC477517
0.8293	Intermediate Similarity	NPC43319
0.8291	Intermediate Similarity	NPC60211
0.8289	Intermediate Similarity	NPC110419
0.8282	Intermediate Similarity	NPC270837
0.828	Intermediate Similarity	NPC85131
0.828	Intermediate Similarity	NPC472279
0.8276	Intermediate Similarity	NPC96024
0.8272	Intermediate Similarity	NPC478134
0.8272	Intermediate Similarity	NPC472906
0.8264	Intermediate Similarity	NPC84076
0.8264	Intermediate Similarity	NPC90128
0.8264	Intermediate Similarity	NPC276014
0.8264	Intermediate Similarity	NPC179777
0.8264	Intermediate Similarity	NPC303680
0.8263	Intermediate Similarity	NPC476640
0.8263	Intermediate Similarity	NPC216842
0.8263	Intermediate Similarity	NPC82217
0.8263	Intermediate Similarity	NPC65885
0.8261	Intermediate Similarity	NPC228654
0.8258	Intermediate Similarity	NPC58752
0.8255	Intermediate Similarity	NPC258502
0.8243	Intermediate Similarity	NPC111845
0.8243	Intermediate Similarity	NPC138472
0.8242	Intermediate Similarity	NPC218226
0.8242	Intermediate Similarity	NPC186392
0.8242	Intermediate Similarity	NPC150131
0.8239	Intermediate Similarity	NPC474000
0.8239	Intermediate Similarity	NPC472905
0.8239	Intermediate Similarity	NPC475770
0.8235	Intermediate Similarity	NPC312256
0.8235	Intermediate Similarity	NPC86455
0.8235	Intermediate Similarity	NPC475996
0.8235	Intermediate Similarity	NPC137920
0.8235	Intermediate Similarity	NPC125134
0.8235	Intermediate Similarity	NPC248068
0.8231	Intermediate Similarity	NPC239134
0.8231	Intermediate Similarity	NPC164295
0.8228	Intermediate Similarity	NPC118332
0.8224	Intermediate Similarity	NPC28398
0.8221	Intermediate Similarity	NPC294965
0.8221	Intermediate Similarity	NPC476247
0.8217	Intermediate Similarity	NPC134293
0.8217	Intermediate Similarity	NPC329933
0.8217	Intermediate Similarity	NPC38545

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 NPC472838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	1032
0.2-0.3	1407
0.3-0.4	2641
0.4-0.5	1922
0.5-0.6	1108
0.6-0.7	507
0.7-0.8	139
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.8193	Intermediate Similarity	NPD5844	Phase 1
0.817	Intermediate Similarity	NPD7003	Approved
0.814	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD3882	Suspended
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7458	Discontinued
0.7931	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1934	Approved
0.7838	Intermediate Similarity	NPD9494	Approved
0.7805	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2801	Approved
0.7764	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6959	Discontinued
0.7708	Intermediate Similarity	NPD1651	Approved
0.7707	Intermediate Similarity	NPD8166	Discontinued
0.7697	Intermediate Similarity	NPD4060	Phase 1
0.7688	Intermediate Similarity	NPD1512	Approved
0.7683	Intermediate Similarity	NPD1465	Phase 2
0.7677	Intermediate Similarity	NPD2935	Discontinued
0.7673	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7075	Discontinued
0.7636	Intermediate Similarity	NPD3817	Phase 2
0.7635	Intermediate Similarity	NPD1283	Approved
0.7628	Intermediate Similarity	NPD2346	Discontinued
0.7625	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3972	Approved
0.7607	Intermediate Similarity	NPD4380	Phase 2
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7576	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6798	Discontinued
0.7564	Intermediate Similarity	NPD5404	Approved
0.7564	Intermediate Similarity	NPD5408	Approved
0.7564	Intermediate Similarity	NPD5406	Approved
0.7564	Intermediate Similarity	NPD5405	Approved
0.7562	Intermediate Similarity	NPD7390	Discontinued
0.7562	Intermediate Similarity	NPD1511	Approved
0.7546	Intermediate Similarity	NPD3226	Approved
0.7542	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2344	Approved
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1607	Approved
0.7484	Intermediate Similarity	NPD3750	Approved
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.747	Intermediate Similarity	NPD7819	Suspended
0.7456	Intermediate Similarity	NPD5494	Approved
0.7448	Intermediate Similarity	NPD5536	Phase 2
0.7432	Intermediate Similarity	NPD1281	Approved
0.7429	Intermediate Similarity	NPD7251	Discontinued
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4626	Approved
0.7414	Intermediate Similarity	NPD7074	Phase 3
0.741	Intermediate Similarity	NPD6801	Discontinued
0.7399	Intermediate Similarity	NPD3818	Discontinued
0.7399	Intermediate Similarity	NPD7177	Discontinued
0.7394	Intermediate Similarity	NPD7028	Phase 2
0.7389	Intermediate Similarity	NPD2799	Discontinued
0.7389	Intermediate Similarity	NPD1510	Phase 2
0.7386	Intermediate Similarity	NPD7808	Phase 3
0.7386	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6273	Approved
0.7356	Intermediate Similarity	NPD7054	Approved
0.7355	Intermediate Similarity	NPD3620	Phase 2
0.7355	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1240	Approved
0.7355	Intermediate Similarity	NPD943	Approved
0.7351	Intermediate Similarity	NPD1470	Approved
0.7349	Intermediate Similarity	NPD7411	Suspended
0.7346	Intermediate Similarity	NPD6799	Approved
0.7329	Intermediate Similarity	NPD2309	Approved
0.7329	Intermediate Similarity	NPD6190	Approved
0.7326	Intermediate Similarity	NPD3926	Phase 2
0.7318	Intermediate Similarity	NPD8150	Discontinued
0.7315	Intermediate Similarity	NPD1201	Approved
0.7314	Intermediate Similarity	NPD7472	Approved
0.7308	Intermediate Similarity	NPD6355	Discontinued
0.7303	Intermediate Similarity	NPD2798	Approved
0.7299	Intermediate Similarity	NPD3751	Discontinued
0.7296	Intermediate Similarity	NPD1471	Phase 3
0.7294	Intermediate Similarity	NPD6234	Discontinued
0.7294	Intermediate Similarity	NPD919	Approved
0.7285	Intermediate Similarity	NPD1876	Approved
0.7284	Intermediate Similarity	NPD3300	Phase 2
0.7283	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD7095	Approved
0.7257	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5049	Phase 3
0.7247	Intermediate Similarity	NPD8312	Approved
0.7247	Intermediate Similarity	NPD8313	Approved
0.7244	Intermediate Similarity	NPD2979	Phase 3
0.7235	Intermediate Similarity	NPD3749	Approved
0.7233	Intermediate Similarity	NPD2438	Suspended
0.7232	Intermediate Similarity	NPD6559	Discontinued
0.7226	Intermediate Similarity	NPD3764	Approved
0.7222	Intermediate Similarity	NPD2354	Approved
0.7219	Intermediate Similarity	NPD5978	Approved
0.7219	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5977	Approved
0.7209	Intermediate Similarity	NPD7199	Phase 2
0.7209	Intermediate Similarity	NPD1247	Approved
0.7202	Intermediate Similarity	NPD37	Approved
0.7198	Intermediate Similarity	NPD2490	Approved
0.7198	Intermediate Similarity	NPD2488	Approved
0.7195	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2532	Approved
0.7195	Intermediate Similarity	NPD2534	Approved
0.7195	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD6233	Phase 2
0.7172	Intermediate Similarity	NPD5283	Phase 1
0.717	Intermediate Similarity	NPD3748	Approved
0.7166	Intermediate Similarity	NPD6777	Approved
0.7166	Intermediate Similarity	NPD6776	Approved
0.7166	Intermediate Similarity	NPD6780	Approved
0.7166	Intermediate Similarity	NPD6782	Approved
0.7166	Intermediate Similarity	NPD6779	Approved
0.7166	Intermediate Similarity	NPD6778	Approved
0.7166	Intermediate Similarity	NPD6781	Approved
0.7153	Intermediate Similarity	NPD228	Approved
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7135	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2313	Discontinued
0.7114	Intermediate Similarity	NPD5691	Approved
0.711	Intermediate Similarity	NPD8127	Discontinued
0.7102	Intermediate Similarity	NPD7228	Approved
0.709	Intermediate Similarity	NPD2491	Approved
0.709	Intermediate Similarity	NPD3057	Approved
0.7089	Intermediate Similarity	NPD447	Suspended
0.7081	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4967	Phase 2
0.7076	Intermediate Similarity	NPD4966	Approved
0.7076	Intermediate Similarity	NPD4965	Approved
0.7069	Intermediate Similarity	NPD3787	Discontinued
0.7067	Intermediate Similarity	NPD3019	Approved
0.7067	Intermediate Similarity	NPD2932	Approved
0.7063	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7051	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3027	Phase 3
0.7051	Intermediate Similarity	NPD7008	Discontinued
0.7041	Intermediate Similarity	NPD6873	Phase 2
0.7039	Intermediate Similarity	NPD7685	Pre-registration
0.7019	Intermediate Similarity	NPD2796	Approved
0.7019	Intermediate Similarity	NPD6100	Approved
0.7019	Intermediate Similarity	NPD6099	Approved
0.7019	Intermediate Similarity	NPD2531	Phase 2
0.7018	Intermediate Similarity	NPD5402	Approved
0.7018	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7870	Phase 2
0.7016	Intermediate Similarity	NPD7871	Phase 2
0.7012	Intermediate Similarity	NPD3887	Approved
0.7006	Intermediate Similarity	NPD5403	Approved
0.7006	Intermediate Similarity	NPD3268	Approved
0.7	Intermediate Similarity	NPD3533	Approved
0.7	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3448	Approved
0.7	Intermediate Similarity	NPD2972	Approved
0.6994	Remote Similarity	NPD6674	Discontinued
0.6988	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1933	Approved
0.6981	Remote Similarity	NPD230	Phase 1
0.6975	Remote Similarity	NPD2353	Approved
0.6975	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7697	Approved
0.6963	Remote Similarity	NPD7696	Phase 3
0.6963	Remote Similarity	NPD7698	Approved
0.6959	Remote Similarity	NPD8151	Discontinued
0.6951	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4110	Phase 3
0.6947	Remote Similarity	NPD2494	Approved
0.6947	Remote Similarity	NPD2493	Approved
0.6943	Remote Similarity	NPD4625	Phase 3
0.694	Remote Similarity	NPD8434	Phase 2
0.6923	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3455	Phase 2
0.6923	Remote Similarity	NPD824	Approved
0.6923	Remote Similarity	NPD7874	Approved
0.6914	Remote Similarity	NPD4477	Approved
0.6914	Remote Similarity	NPD4476	Approved
0.6913	Remote Similarity	NPD405	Clinical (unspecified phase)

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