NPASS Compound

Structure

NPC265454 OpenBabel07101718182D 24 25 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 -1.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 1 13 2 0 0 0 0 2 7 2 0 0 0 0 2 13 1 0 0 0 0 3 8 1 0 0 0 0 3 13 1 0 0 0 0 4 9 1 0 0 0 0 4 14 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 22 1 1 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.15
Volume:	345.563
LogP:	1.782
LogD:	2.026
LogS:	-2.046
# Rotatable Bonds:	8
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	2.697
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.932
MDCK Permeability:	1.3508648407878354e-05
Pgp-inhibitor:	0.092
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.128
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	90.07396697998047%
Volume Distribution (VD):	0.842
Pgp-substrate:	12.664860725402832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.432
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.715
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.722
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.817
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.303
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	19.591
Half-life (T1/2):	0.946

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.539
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.93
Carcinogencity:	0.198
Eye Corrosion:	0.009
Eye Irritation:	0.914
Respiratory Toxicity:	0.306

Download Data

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

Natural Product: NPC265454

Natural Product ID:	NPC265454
*Common Name:**	(5S)-7-(3,4-Dihydroxyphenyl)-5-Hydroxy-1-(4-Hydroxyphenyl)Heptan-3-One
IUPAC Name:	(5S)-7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxyphenyl)heptan-3-one
Synonyms:
Standard InCHIKey:	OAGXTVOZBKKJKA-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C19H22O5/c20-15-6-1-13(2-7-15)3-8-16(21)12-17(22)9-4-14-5-10-18(23)19(24)11-14/h1-2,5-7,10-11,17,20,22-24H,3-4,8-9,12H2/t17-/m0/s1
SMILES:	c1cc(ccc1CCC(=O)C[C@H](CCc1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1824571
PubChem CID:	38351522
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO32876	alnus hirsuta f. sibirica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23465614]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	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
Others	3

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	82840.0	nM	PMID[541377]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	57.6	%	PMID[541378]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	70.5	%	PMID[541378]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	77.3	%	PMID[541378]

☑ 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 NPC265454 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	275
0.1-0.2	1229
0.2-0.3	3394
0.3-0.4	10729
0.4-0.5	8781
0.5-0.6	5726
0.6-0.7	9767
0.7-0.8	2584
0.8-0.85	133
0.85-0.9	64
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC34634
0.9739	High Similarity	NPC86900
0.9737	High Similarity	NPC98305
0.9196	High Similarity	NPC177576
0.913	High Similarity	NPC61062
0.913	High Similarity	NPC277394
0.913	High Similarity	NPC299252
0.9107	High Similarity	NPC226401
0.9107	High Similarity	NPC252544
0.9107	High Similarity	NPC174096
0.9107	High Similarity	NPC120982
0.9107	High Similarity	NPC321252
0.9107	High Similarity	NPC147634
0.9107	High Similarity	NPC79793
0.9106	High Similarity	NPC311419
0.9106	High Similarity	NPC215941
0.9106	High Similarity	NPC137427
0.9106	High Similarity	NPC123196
0.9106	High Similarity	NPC319282
0.9106	High Similarity	NPC244246
0.9106	High Similarity	NPC275724
0.9106	High Similarity	NPC65935
0.9027	High Similarity	NPC179002
0.9027	High Similarity	NPC257430
0.9027	High Similarity	NPC187583
0.9018	High Similarity	NPC62258
0.9018	High Similarity	NPC55617
0.8957	High Similarity	NPC285350
0.8862	High Similarity	NPC20287
0.8862	High Similarity	NPC20404
0.8862	High Similarity	NPC12022
0.8862	High Similarity	NPC293641
0.8833	High Similarity	NPC472271
0.8793	High Similarity	NPC120280
0.879	High Similarity	NPC278308
0.8761	High Similarity	NPC317305
0.875	High Similarity	NPC180171
0.875	High Similarity	NPC103398
0.875	High Similarity	NPC158325
0.8739	High Similarity	NPC109371
0.8739	High Similarity	NPC182240
0.8739	High Similarity	NPC470215
0.8739	High Similarity	NPC470214
0.8729	High Similarity	NPC145023
0.8729	High Similarity	NPC175799
0.8729	High Similarity	NPC610
0.8729	High Similarity	NPC200988
0.8718	High Similarity	NPC23402
0.8699	High Similarity	NPC257589
0.8699	High Similarity	NPC53305
0.8696	High Similarity	NPC297657
0.8655	High Similarity	NPC86198
0.8655	High Similarity	NPC63126
0.8629	High Similarity	NPC127937
0.8629	High Similarity	NPC92207
0.8621	High Similarity	NPC51698
0.8618	High Similarity	NPC231767
0.8618	High Similarity	NPC85565
0.8609	High Similarity	NPC222084
0.8595	High Similarity	NPC236520
0.8595	High Similarity	NPC294361
0.8584	High Similarity	NPC188677
0.8583	High Similarity	NPC70084
0.8571	High Similarity	NPC8931
0.8571	High Similarity	NPC120693
0.8571	High Similarity	NPC261573
0.8571	High Similarity	NPC471511
0.8548	High Similarity	NPC127975
0.8547	High Similarity	NPC148969
0.8537	High Similarity	NPC244876
0.8522	High Similarity	NPC254833
0.8522	High Similarity	NPC228343
0.8504	High Similarity	NPC195292
0.8504	High Similarity	NPC244441
0.85	High Similarity	NPC249435
0.8492	Intermediate Similarity	NPC226661
0.8485	Intermediate Similarity	NPC474784
0.848	Intermediate Similarity	NPC303680
0.848	Intermediate Similarity	NPC90128
0.848	Intermediate Similarity	NPC84076
0.8468	Intermediate Similarity	NPC288945
0.845	Intermediate Similarity	NPC471749
0.8438	Intermediate Similarity	NPC476407
0.8425	Intermediate Similarity	NPC304622
0.8421	Intermediate Similarity	NPC70843
0.8413	Intermediate Similarity	NPC123722
0.8413	Intermediate Similarity	NPC5018
0.8413	Intermediate Similarity	NPC123228
0.8413	Intermediate Similarity	NPC151167
0.8413	Intermediate Similarity	NPC276466
0.84	Intermediate Similarity	NPC3221
0.8393	Intermediate Similarity	NPC110764
0.839	Intermediate Similarity	NPC471485
0.8387	Intermediate Similarity	NPC163083
0.8385	Intermediate Similarity	NPC106406
0.8374	Intermediate Similarity	NPC322332
0.8374	Intermediate Similarity	NPC201777
0.8362	Intermediate Similarity	NPC88141
0.8361	Intermediate Similarity	NPC473136
0.8359	Intermediate Similarity	NPC142985
0.8333	Intermediate Similarity	NPC279676
0.8333	Intermediate Similarity	NPC179777
0.8333	Intermediate Similarity	NPC308976
0.8333	Intermediate Similarity	NPC67349
0.8333	Intermediate Similarity	NPC239291
0.8304	Intermediate Similarity	NPC294741
0.8304	Intermediate Similarity	NPC223393
0.8295	Intermediate Similarity	NPC198388
0.8295	Intermediate Similarity	NPC469480
0.8293	Intermediate Similarity	NPC470848
0.8293	Intermediate Similarity	NPC470849
0.8293	Intermediate Similarity	NPC207613
0.8281	Intermediate Similarity	NPC241354
0.8279	Intermediate Similarity	NPC141791
0.8279	Intermediate Similarity	NPC263386
0.8271	Intermediate Similarity	NPC175552
0.8261	Intermediate Similarity	NPC95178
0.8261	Intermediate Similarity	NPC29989
0.8261	Intermediate Similarity	NPC69332
0.825	Intermediate Similarity	NPC4665
0.8246	Intermediate Similarity	NPC12278
0.8231	Intermediate Similarity	NPC5419
0.8231	Intermediate Similarity	NPC25581
0.8231	Intermediate Similarity	NPC18074
0.8231	Intermediate Similarity	NPC61
0.823	Intermediate Similarity	NPC91461
0.823	Intermediate Similarity	NPC7686
0.823	Intermediate Similarity	NPC40258
0.8226	Intermediate Similarity	NPC470212
0.8226	Intermediate Similarity	NPC54872
0.8226	Intermediate Similarity	NPC31936
0.8226	Intermediate Similarity	NPC324571
0.8226	Intermediate Similarity	NPC312675
0.8226	Intermediate Similarity	NPC184651
0.8226	Intermediate Similarity	NPC262156
0.8226	Intermediate Similarity	NPC473853
0.8226	Intermediate Similarity	NPC113865
0.8226	Intermediate Similarity	NPC343720
0.8217	Intermediate Similarity	NPC233056
0.8214	Intermediate Similarity	NPC131587
0.8214	Intermediate Similarity	NPC51333
0.8214	Intermediate Similarity	NPC78119
0.8214	Intermediate Similarity	NPC132078
0.8214	Intermediate Similarity	NPC216468
0.8209	Intermediate Similarity	NPC156709
0.8209	Intermediate Similarity	NPC179505
0.8205	Intermediate Similarity	NPC326187
0.8203	Intermediate Similarity	NPC158673
0.8197	Intermediate Similarity	NPC104514
0.8195	Intermediate Similarity	NPC170742
0.8182	Intermediate Similarity	NPC113295
0.8182	Intermediate Similarity	NPC123988
0.8175	Intermediate Similarity	NPC15127
0.8175	Intermediate Similarity	NPC471927
0.8168	Intermediate Similarity	NPC327410
0.8168	Intermediate Similarity	NPC168799
0.8168	Intermediate Similarity	NPC155209
0.8162	Intermediate Similarity	NPC30846
0.8162	Intermediate Similarity	NPC471971
0.8162	Intermediate Similarity	NPC285550
0.8162	Intermediate Similarity	NPC471972
0.8162	Intermediate Similarity	NPC469855
0.8158	Intermediate Similarity	NPC196479
0.8154	Intermediate Similarity	NPC318799
0.8151	Intermediate Similarity	NPC286222
0.8142	Intermediate Similarity	NPC213730
0.8136	Intermediate Similarity	NPC44732
0.8134	Intermediate Similarity	NPC206207
0.813	Intermediate Similarity	NPC299406
0.8125	Intermediate Similarity	NPC109955
0.8125	Intermediate Similarity	NPC107672
0.8125	Intermediate Similarity	NPC156539
0.812	Intermediate Similarity	NPC324929
0.812	Intermediate Similarity	NPC65005
0.812	Intermediate Similarity	NPC194764
0.812	Intermediate Similarity	NPC264112
0.8115	Intermediate Similarity	NPC325295
0.8115	Intermediate Similarity	NPC150919
0.8115	Intermediate Similarity	NPC76308
0.811	Intermediate Similarity	NPC280767
0.8106	Intermediate Similarity	NPC471913
0.8106	Intermediate Similarity	NPC4982
0.8106	Intermediate Similarity	NPC300776
0.8106	Intermediate Similarity	NPC68779
0.8106	Intermediate Similarity	NPC5310
0.8106	Intermediate Similarity	NPC176814
0.8103	Intermediate Similarity	NPC477814
0.8102	Intermediate Similarity	NPC46161
0.8102	Intermediate Similarity	NPC239608
0.8102	Intermediate Similarity	NPC183824
0.8095	Intermediate Similarity	NPC471693
0.8095	Intermediate Similarity	NPC198014
0.8095	Intermediate Similarity	NPC473451
0.8095	Intermediate Similarity	NPC257976
0.8095	Intermediate Similarity	NPC242372
0.8095	Intermediate Similarity	NPC164778
0.8095	Intermediate Similarity	NPC4181
0.8092	Intermediate Similarity	NPC135801
0.8087	Intermediate Similarity	NPC52087
0.8087	Intermediate Similarity	NPC323810

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 NPC265454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	875
0.2-0.3	1411
0.3-0.4	2752
0.4-0.5	2051
0.5-0.6	1203
0.6-0.7	528
0.7-0.8	83
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8522	High Similarity	NPD3022	Approved
0.8522	High Similarity	NPD3021	Approved
0.8092	Intermediate Similarity	NPD943	Approved
0.7953	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD2859	Approved
0.7788	Intermediate Similarity	NPD2860	Approved
0.7778	Intermediate Similarity	NPD2932	Approved
0.7778	Intermediate Similarity	NPD3019	Approved
0.7739	Intermediate Similarity	NPD3020	Approved
0.7727	Intermediate Similarity	NPD3027	Phase 3
0.7699	Intermediate Similarity	NPD2933	Approved
0.7699	Intermediate Similarity	NPD2934	Approved
0.7698	Intermediate Similarity	NPD8166	Discontinued
0.7687	Intermediate Similarity	NPD826	Approved
0.7687	Intermediate Similarity	NPD825	Approved
0.7664	Intermediate Similarity	NPD9570	Approved
0.7643	Intermediate Similarity	NPD6190	Approved
0.7634	Intermediate Similarity	NPD257	Approved
0.7634	Intermediate Similarity	NPD258	Approved
0.7551	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1201	Approved
0.7483	Intermediate Similarity	NPD1934	Approved
0.7483	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD228	Approved
0.7444	Intermediate Similarity	NPD9569	Approved
0.7426	Intermediate Similarity	NPD3062	Approved
0.7426	Intermediate Similarity	NPD3059	Approved
0.7426	Intermediate Similarity	NPD3061	Approved
0.7424	Intermediate Similarity	NPD1470	Approved
0.7402	Intermediate Similarity	NPD5536	Phase 2
0.7385	Intermediate Similarity	NPD3092	Approved
0.7372	Intermediate Similarity	NPD555	Phase 2
0.7364	Intermediate Similarity	NPD9381	Approved
0.7364	Intermediate Similarity	NPD9384	Approved
0.736	Intermediate Similarity	NPD5283	Phase 1
0.7357	Intermediate Similarity	NPD7266	Discontinued
0.7353	Intermediate Similarity	NPD259	Phase 1
0.7353	Intermediate Similarity	NPD6663	Approved
0.7344	Intermediate Similarity	NPD3091	Approved
0.7338	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1237	Approved
0.7323	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5314	Approved
0.7313	Intermediate Similarity	NPD5736	Approved
0.7313	Intermediate Similarity	NPD9494	Approved
0.7308	Intermediate Similarity	NPD3023	Approved
0.7308	Intermediate Similarity	NPD3026	Approved
0.7302	Intermediate Similarity	NPD2629	Approved
0.7299	Intermediate Similarity	NPD1613	Approved
0.7299	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3094	Phase 2
0.7292	Intermediate Similarity	NPD1511	Approved
0.7287	Intermediate Similarity	NPD1651	Approved
0.7287	Intermediate Similarity	NPD3024	Approved
0.7287	Intermediate Similarity	NPD3025	Approved
0.7286	Intermediate Similarity	NPD2935	Discontinued
0.728	Intermediate Similarity	NPD9379	Approved
0.728	Intermediate Similarity	NPD9377	Approved
0.7279	Intermediate Similarity	NPD6798	Discontinued
0.7279	Intermediate Similarity	NPD3455	Phase 2
0.7246	Intermediate Similarity	NPD6355	Discontinued
0.7246	Intermediate Similarity	NPD275	Approved
0.7246	Intermediate Similarity	NPD274	Approved
0.7241	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1242	Phase 1
0.7226	Intermediate Similarity	NPD6166	Phase 2
0.7226	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3882	Suspended
0.7218	Intermediate Similarity	NPD5310	Approved
0.7218	Intermediate Similarity	NPD5311	Approved
0.7206	Intermediate Similarity	NPD9537	Phase 1
0.7206	Intermediate Similarity	NPD9536	Phase 1
0.7203	Intermediate Similarity	NPD4110	Phase 3
0.7203	Intermediate Similarity	NPD9495	Approved
0.7203	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3400	Discontinued
0.72	Intermediate Similarity	NPD2801	Approved
0.7197	Intermediate Similarity	NPD9269	Phase 2
0.7192	Intermediate Similarity	NPD1512	Approved
0.7179	Intermediate Similarity	NPD844	Approved
0.7174	Intermediate Similarity	NPD3620	Phase 2
0.7174	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3055	Approved
0.7164	Intermediate Similarity	NPD1164	Approved
0.7164	Intermediate Similarity	NPD3053	Approved
0.7143	Intermediate Similarity	NPD9622	Approved
0.7134	Intermediate Similarity	NPD3818	Discontinued
0.7122	Intermediate Similarity	NPD230	Phase 1
0.712	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4380	Phase 2
0.7101	Intermediate Similarity	NPD4062	Phase 3
0.7101	Intermediate Similarity	NPD6233	Phase 2
0.7099	Intermediate Similarity	NPD3095	Discontinued
0.7092	Intermediate Similarity	NPD1510	Phase 2
0.709	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD4628	Phase 3
0.7077	Intermediate Similarity	NPD1894	Discontinued
0.7055	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5137	Approved
0.705	Intermediate Similarity	NPD4060	Phase 1
0.7045	Intermediate Similarity	NPD3847	Discontinued
0.7044	Intermediate Similarity	NPD7074	Phase 3
0.7042	Intermediate Similarity	NPD5406	Approved
0.7042	Intermediate Similarity	NPD5404	Approved
0.7042	Intermediate Similarity	NPD5405	Approved
0.7042	Intermediate Similarity	NPD5408	Approved
0.7029	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1755	Approved
0.7007	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1535	Discovery
0.6992	Remote Similarity	NPD5048	Discontinued
0.6986	Remote Similarity	NPD3300	Phase 2
0.6985	Remote Similarity	NPD9621	Approved
0.6985	Remote Similarity	NPD9620	Approved
0.6985	Remote Similarity	NPD9619	Approved
0.6985	Remote Similarity	NPD5647	Approved
0.6981	Remote Similarity	NPD7054	Approved
0.6977	Remote Similarity	NPD256	Approved
0.6977	Remote Similarity	NPD255	Approved
0.6975	Remote Similarity	NPD288	Approved
0.6972	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2684	Approved
0.6957	Remote Similarity	NPD7095	Approved
0.6953	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.695	Remote Similarity	NPD817	Approved
0.695	Remote Similarity	NPD823	Approved
0.6944	Remote Similarity	NPD1549	Phase 2
0.6942	Remote Similarity	NPD3028	Approved
0.6942	Remote Similarity	NPD289	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1481	Phase 2
0.694	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7472	Approved
0.6934	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1240	Approved
0.6918	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD37	Approved
0.6906	Remote Similarity	NPD601	Approved
0.6906	Remote Similarity	NPD598	Approved
0.6906	Remote Similarity	NPD597	Approved
0.6906	Remote Similarity	NPD3764	Approved
0.6903	Remote Similarity	NPD111	Approved
0.6903	Remote Similarity	NPD6234	Discontinued
0.6894	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1357	Approved
0.6894	Remote Similarity	NPD9268	Approved
0.6894	Remote Similarity	NPD6797	Phase 2
0.6889	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD940	Approved
0.6885	Remote Similarity	NPD846	Approved
0.688	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.688	Remote Similarity	NPD2342	Discontinued
0.6875	Remote Similarity	NPD7843	Approved
0.6875	Remote Similarity	NPD7635	Approved
0.6866	Remote Similarity	NPD1281	Approved
0.6866	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2798	Approved
0.6857	Remote Similarity	NPD1136	Approved
0.6857	Remote Similarity	NPD1130	Approved
0.6857	Remote Similarity	NPD1132	Approved
0.6853	Remote Similarity	NPD2799	Discontinued
0.6853	Remote Similarity	NPD7033	Discontinued
0.6853	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7251	Discontinued
0.6846	Remote Similarity	NPD7157	Approved
0.6839	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1607	Approved
0.6828	Remote Similarity	NPD4534	Discontinued
0.6828	Remote Similarity	NPD5958	Discontinued
0.6825	Remote Similarity	NPD74	Approved
0.6825	Remote Similarity	NPD9266	Approved
0.6824	Remote Similarity	NPD7390	Discontinued
0.6822	Remote Similarity	NPD1241	Discontinued
0.6822	Remote Similarity	NPD2228	Approved
0.6822	Remote Similarity	NPD2234	Approved
0.6822	Remote Similarity	NPD2229	Approved
0.6818	Remote Similarity	NPD9545	Approved
0.6818	Remote Similarity	NPD3817	Phase 2
0.6815	Remote Similarity	NPD1608	Approved
0.6815	Remote Similarity	NPD3972	Approved
0.6812	Remote Similarity	NPD2861	Phase 2
0.681	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2979	Phase 3
0.6806	Remote Similarity	NPD2438	Suspended
0.6794	Remote Similarity	NPD9568	Approved
0.6794	Remote Similarity	NPD9493	Approved
0.6786	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3060	Approved
0.6779	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4966	Approved
0.6774	Remote Similarity	NPD4967	Phase 2
0.6774	Remote Similarity	NPD4965	Approved
0.6772	Remote Similarity	NPD1792	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data