NPASS Compound

Structure

NPC52161 OpenBabel07101718282D 26 30 0 0 1 0 0 0 0 0999 V2000 3.4343 -0.7693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3639 0.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5531 0.5961 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8220 -0.1365 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.9135 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 -4.4152 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 -1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1877 1.5269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8108 0.0125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 10 1 0 0 0 0 4 12 2 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 19 2 0 0 0 0 10 17 1 0 0 0 0 10 18 2 0 0 0 0 11 7 1 1 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 20 2 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 24 2 0 0 0 0 15 21 1 0 0 0 0 15 25 1 1 0 0 0 16 20 1 0 0 0 0 16 26 1 6 0 0 0 17 21 2 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	4.435
LogD:	3.852
LogS:	-3.774
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	4.811
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.384
MDCK Permeability:	1.0426256267237477e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.097
30% Bioavailability (F30%):	0.308

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.666
Plasma Protein Binding (PPB):	93.51171875%
Volume Distribution (VD):	0.597
Pgp-substrate:	4.884577751159668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.813
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.198
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.289
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	3.577
Half-life (T1/2):	0.089

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.433
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.358
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.47
Carcinogencity:	0.233
Eye Corrosion:	0.023
Eye Irritation:	0.027
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC52161

Natural Product ID:	NPC52161
*Common Name:**	Hypoxylonol B
IUPAC Name:	n.a.
Synonyms:	Hypoxylonol B
Standard InCHIKey:	VNVXZDRVVHCQPB-RLCCDNCMSA-N
Standard InCHI:	InChI=1S/C21H18O5/c1-26-16-8-15(25)21-17-10-3-2-4-12(22)18(10)14(24)7-11(17)9-5-6-13(23)20(16)19(9)21/h2-6,11,15-16,22-23,25H,7-8H2,1H3/t11-,15+,16+/m1/s1
SMILES:	CO[C@H]1C[C@@H](C2=C3c4cccc(c4C(=O)C[C@@H]3c3ccc(c1c23)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1950967
PubChem CID:	57333864
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO30840	Hypoxylon truncatum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253861]
NPO30840	Hypoxylon truncatum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21082806]
NPO30840	Hypoxylon truncatum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148396]

☑ 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
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	24000.0	nM	PMID[449512]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24000.0	nM	PMID[449512]

☑ 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 NPC52161 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	337
0.1-0.2	1322
0.2-0.3	2587
0.3-0.4	6709
0.4-0.5	12014
0.5-0.6	4181
0.6-0.7	6658
0.7-0.8	7140
0.8-0.85	1523
0.85-0.9	217
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC162751
0.9929	High Similarity	NPC106524
0.9929	High Similarity	NPC290695
0.9571	High Similarity	NPC106519
0.9571	High Similarity	NPC91019
0.9189	High Similarity	NPC477276
0.8784	High Similarity	NPC34482
0.875	High Similarity	NPC478220
0.8725	High Similarity	NPC470570
0.8716	High Similarity	NPC193703
0.8716	High Similarity	NPC21599
0.8716	High Similarity	NPC48762
0.8684	High Similarity	NPC470569
0.8675	High Similarity	NPC329933
0.8618	High Similarity	NPC205766
0.8618	High Similarity	NPC255641
0.8618	High Similarity	NPC470568
0.8618	High Similarity	NPC290954
0.8599	High Similarity	NPC18380
0.859	High Similarity	NPC324736
0.859	High Similarity	NPC195167
0.859	High Similarity	NPC186113
0.8581	High Similarity	NPC474961
0.8581	High Similarity	NPC135524
0.8581	High Similarity	NPC85310
0.8571	High Similarity	NPC182921
0.8571	High Similarity	NPC168471
0.8571	High Similarity	NPC218870
0.8571	High Similarity	NPC474824
0.8571	High Similarity	NPC478218
0.8571	High Similarity	NPC470408
0.8562	High Similarity	NPC476553
0.8562	High Similarity	NPC476552
0.8562	High Similarity	NPC476551
0.8553	High Similarity	NPC477221
0.8544	High Similarity	NPC478229
0.8543	High Similarity	NPC34802
0.8535	High Similarity	NPC284495
0.8535	High Similarity	NPC184326
0.8535	High Similarity	NPC292863
0.8533	High Similarity	NPC478019
0.8533	High Similarity	NPC170055
0.8523	High Similarity	NPC471731
0.8523	High Similarity	NPC313047
0.8523	High Similarity	NPC474203
0.8523	High Similarity	NPC3732
0.8523	High Similarity	NPC451542
0.8523	High Similarity	NPC295712
0.8516	High Similarity	NPC226656
0.8516	High Similarity	NPC66508
0.8514	High Similarity	NPC305845
0.8514	High Similarity	NPC204045
0.8514	High Similarity	NPC477275
0.8506	High Similarity	NPC113608
0.8506	High Similarity	NPC470338
0.8506	High Similarity	NPC474533
0.8506	High Similarity	NPC474534
0.8506	High Similarity	NPC268992
0.8506	High Similarity	NPC470337
0.8506	High Similarity	NPC51824
0.8506	High Similarity	NPC87708
0.8506	High Similarity	NPC43345
0.8497	Intermediate Similarity	NPC477914
0.8497	Intermediate Similarity	NPC147735
0.8491	Intermediate Similarity	NPC290160
0.8481	Intermediate Similarity	NPC478222
0.8481	Intermediate Similarity	NPC137232
0.8477	Intermediate Similarity	NPC147250
0.8472	Intermediate Similarity	NPC314048
0.8471	Intermediate Similarity	NPC472617
0.8467	Intermediate Similarity	NPC300684
0.8467	Intermediate Similarity	NPC48130
0.8467	Intermediate Similarity	NPC42540
0.8467	Intermediate Similarity	NPC218866
0.8467	Intermediate Similarity	NPC477913
0.8467	Intermediate Similarity	NPC84568
0.8467	Intermediate Similarity	NPC151607
0.8462	Intermediate Similarity	NPC72669
0.8462	Intermediate Similarity	NPC474861
0.8462	Intermediate Similarity	NPC474517
0.8456	Intermediate Similarity	NPC469520
0.8456	Intermediate Similarity	NPC40118
0.8456	Intermediate Similarity	NPC232021
0.8456	Intermediate Similarity	NPC471733
0.8456	Intermediate Similarity	NPC126534
0.8452	Intermediate Similarity	NPC135522
0.8452	Intermediate Similarity	NPC329844
0.8446	Intermediate Similarity	NPC169452
0.8446	Intermediate Similarity	NPC181560
0.8442	Intermediate Similarity	NPC474417
0.8442	Intermediate Similarity	NPC72958
0.8442	Intermediate Similarity	NPC478148
0.8442	Intermediate Similarity	NPC149526
0.8442	Intermediate Similarity	NPC232645
0.8431	Intermediate Similarity	NPC478219
0.8428	Intermediate Similarity	NPC473961
0.8425	Intermediate Similarity	NPC191976
0.8421	Intermediate Similarity	NPC475348
0.8421	Intermediate Similarity	NPC289042
0.8421	Intermediate Similarity	NPC290194
0.8421	Intermediate Similarity	NPC119767
0.8421	Intermediate Similarity	NPC190648
0.8421	Intermediate Similarity	NPC126767
0.8421	Intermediate Similarity	NPC261271
0.8421	Intermediate Similarity	NPC56433
0.8421	Intermediate Similarity	NPC118027
0.8421	Intermediate Similarity	NPC312929
0.8421	Intermediate Similarity	NPC245584
0.8418	Intermediate Similarity	NPC472618
0.8414	Intermediate Similarity	NPC472262
0.8414	Intermediate Similarity	NPC161964
0.8414	Intermediate Similarity	NPC287604
0.84	Intermediate Similarity	NPC159721
0.84	Intermediate Similarity	NPC174905
0.84	Intermediate Similarity	NPC84266
0.84	Intermediate Similarity	NPC293545
0.84	Intermediate Similarity	NPC297600
0.8397	Intermediate Similarity	NPC66029
0.8397	Intermediate Similarity	NPC68727
0.8389	Intermediate Similarity	NPC472603
0.8389	Intermediate Similarity	NPC472604
0.8389	Intermediate Similarity	NPC265178
0.8389	Intermediate Similarity	NPC472605
0.8387	Intermediate Similarity	NPC180944
0.8387	Intermediate Similarity	NPC40356
0.8387	Intermediate Similarity	NPC470340
0.8387	Intermediate Similarity	NPC154683
0.8378	Intermediate Similarity	NPC138099
0.8378	Intermediate Similarity	NPC1268
0.8378	Intermediate Similarity	NPC242994
0.8375	Intermediate Similarity	NPC476505
0.8367	Intermediate Similarity	NPC261292
0.8367	Intermediate Similarity	NPC301915
0.8366	Intermediate Similarity	NPC35150
0.8366	Intermediate Similarity	NPC221352
0.8366	Intermediate Similarity	NPC152233
0.8366	Intermediate Similarity	NPC106328
0.8365	Intermediate Similarity	NPC301256
0.8365	Intermediate Similarity	NPC312273
0.8356	Intermediate Similarity	NPC283088
0.8355	Intermediate Similarity	NPC472134
0.8355	Intermediate Similarity	NPC225173
0.8355	Intermediate Similarity	NPC143685
0.8355	Intermediate Similarity	NPC285122
0.8355	Intermediate Similarity	NPC300540
0.8355	Intermediate Similarity	NPC163846
0.8354	Intermediate Similarity	NPC470333
0.8345	Intermediate Similarity	NPC267205
0.8344	Intermediate Similarity	NPC475705
0.8344	Intermediate Similarity	NPC244691
0.8344	Intermediate Similarity	NPC471906
0.8344	Intermediate Similarity	NPC10764
0.8344	Intermediate Similarity	NPC117836
0.8344	Intermediate Similarity	NPC51887
0.8344	Intermediate Similarity	NPC19896
0.8344	Intermediate Similarity	NPC478223
0.8344	Intermediate Similarity	NPC476178
0.8333	Intermediate Similarity	NPC208806
0.8333	Intermediate Similarity	NPC474622
0.8333	Intermediate Similarity	NPC470102
0.8333	Intermediate Similarity	NPC26238
0.8333	Intermediate Similarity	NPC470087
0.8333	Intermediate Similarity	NPC49108
0.8333	Intermediate Similarity	NPC182255
0.8333	Intermediate Similarity	NPC321980
0.8333	Intermediate Similarity	NPC474621
0.8333	Intermediate Similarity	NPC94076
0.8333	Intermediate Similarity	NPC137649
0.8333	Intermediate Similarity	NPC210942
0.8333	Intermediate Similarity	NPC193555
0.8333	Intermediate Similarity	NPC169990
0.8323	Intermediate Similarity	NPC478022
0.8323	Intermediate Similarity	NPC469664
0.8323	Intermediate Similarity	NPC258249
0.8323	Intermediate Similarity	NPC478020
0.8323	Intermediate Similarity	NPC178484
0.8322	Intermediate Similarity	NPC472601
0.8322	Intermediate Similarity	NPC99731
0.8322	Intermediate Similarity	NPC155205
0.8322	Intermediate Similarity	NPC470211
0.8322	Intermediate Similarity	NPC472366
0.8322	Intermediate Similarity	NPC472600
0.8313	Intermediate Similarity	NPC15374
0.8313	Intermediate Similarity	NPC473012
0.8313	Intermediate Similarity	NPC315772
0.8312	Intermediate Similarity	NPC473016
0.8312	Intermediate Similarity	NPC97028
0.8312	Intermediate Similarity	NPC158338
0.8312	Intermediate Similarity	NPC97029
0.8312	Intermediate Similarity	NPC100985
0.8312	Intermediate Similarity	NPC65589
0.8312	Intermediate Similarity	NPC288036
0.8311	Intermediate Similarity	NPC20210
0.8311	Intermediate Similarity	NPC478200
0.8311	Intermediate Similarity	NPC212693
0.8311	Intermediate Similarity	NPC33144
0.8311	Intermediate Similarity	NPC191835
0.8311	Intermediate Similarity	NPC94248
0.8302	Intermediate Similarity	NPC470810
0.8301	Intermediate Similarity	NPC125801

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 NPC52161 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	873
0.2-0.3	1360
0.3-0.4	2489
0.4-0.5	2253
0.5-0.6	1161
0.6-0.7	548
0.7-0.8	153
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.825	Intermediate Similarity	NPD6959	Discontinued
0.8243	Intermediate Similarity	NPD5404	Approved
0.8243	Intermediate Similarity	NPD5406	Approved
0.8243	Intermediate Similarity	NPD5405	Approved
0.8243	Intermediate Similarity	NPD5408	Approved
0.8224	Intermediate Similarity	NPD7390	Discontinued
0.8176	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1201	Approved
0.8042	Intermediate Similarity	NPD1470	Approved
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.7987	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7473	Discontinued
0.7935	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1510	Phase 2
0.7888	Intermediate Similarity	NPD7768	Phase 2
0.7881	Intermediate Similarity	NPD2935	Discontinued
0.7866	Intermediate Similarity	NPD6232	Discontinued
0.7829	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2533	Approved
0.7821	Intermediate Similarity	NPD2534	Approved
0.7821	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2532	Approved
0.78	Intermediate Similarity	NPD1607	Approved
0.7785	Intermediate Similarity	NPD1240	Approved
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6273	Approved
0.775	Intermediate Similarity	NPD7411	Suspended
0.7736	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1934	Approved
0.7677	Intermediate Similarity	NPD3750	Approved
0.7677	Intermediate Similarity	NPD7003	Approved
0.7665	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6166	Phase 2
0.7665	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3764	Approved
0.7647	Intermediate Similarity	NPD2796	Approved
0.7636	Intermediate Similarity	NPD5494	Approved
0.7633	Intermediate Similarity	NPD5844	Phase 1
0.7625	Intermediate Similarity	NPD3226	Approved
0.7622	Intermediate Similarity	NPD3019	Approved
0.7622	Intermediate Similarity	NPD7075	Discontinued
0.7616	Intermediate Similarity	NPD8312	Approved
0.7616	Intermediate Similarity	NPD8313	Approved
0.7614	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6559	Discontinued
0.7586	Intermediate Similarity	NPD8150	Discontinued
0.7546	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3749	Approved
0.7515	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2932	Approved
0.7485	Intermediate Similarity	NPD37	Approved
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7455	Intermediate Similarity	NPD3882	Suspended
0.7439	Intermediate Similarity	NPD2801	Approved
0.7434	Intermediate Similarity	NPD943	Approved
0.743	Intermediate Similarity	NPD6535	Approved
0.743	Intermediate Similarity	NPD6534	Approved
0.7427	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1511	Approved
0.7417	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7458	Discontinued
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7074	Phase 3
0.7383	Intermediate Similarity	NPD2798	Approved
0.7368	Intermediate Similarity	NPD3818	Discontinued
0.7368	Intermediate Similarity	NPD6663	Approved
0.7365	Intermediate Similarity	NPD1876	Approved
0.7356	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3748	Approved
0.7349	Intermediate Similarity	NPD4967	Phase 2
0.7349	Intermediate Similarity	NPD4965	Approved
0.7349	Intermediate Similarity	NPD4966	Approved
0.7342	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD8166	Discontinued
0.7338	Intermediate Similarity	NPD6651	Approved
0.7333	Intermediate Similarity	NPD5736	Approved
0.7329	Intermediate Similarity	NPD1512	Approved
0.7326	Intermediate Similarity	NPD7054	Approved
0.7322	Intermediate Similarity	NPD6782	Approved
0.7322	Intermediate Similarity	NPD6777	Approved
0.7322	Intermediate Similarity	NPD6780	Approved
0.7322	Intermediate Similarity	NPD6781	Approved
0.7322	Intermediate Similarity	NPD6779	Approved
0.7322	Intermediate Similarity	NPD6778	Approved
0.7322	Intermediate Similarity	NPD6776	Approved
0.7315	Intermediate Similarity	NPD1164	Approved
0.7308	Intermediate Similarity	NPD7700	Phase 2
0.7308	Intermediate Similarity	NPD1551	Phase 2
0.7308	Intermediate Similarity	NPD7699	Phase 2
0.7289	Intermediate Similarity	NPD5402	Approved
0.7285	Intermediate Similarity	NPD4908	Phase 1
0.7284	Intermediate Similarity	NPD5403	Approved
0.7283	Intermediate Similarity	NPD7472	Approved
0.7278	Intermediate Similarity	NPD2800	Approved
0.7262	Intermediate Similarity	NPD6234	Discontinued
0.7258	Intermediate Similarity	NPD8320	Phase 1
0.7258	Intermediate Similarity	NPD8319	Approved
0.7256	Intermediate Similarity	NPD6599	Discontinued
0.725	Intermediate Similarity	NPD3300	Phase 2
0.7248	Intermediate Similarity	NPD1283	Approved
0.7246	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6823	Phase 2
0.7241	Intermediate Similarity	NPD6797	Phase 2
0.7241	Intermediate Similarity	NPD3091	Approved
0.7235	Intermediate Similarity	NPD5710	Approved
0.7235	Intermediate Similarity	NPD5711	Approved
0.7233	Intermediate Similarity	NPD4628	Phase 3
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD5761	Phase 2
0.7222	Intermediate Similarity	NPD9493	Approved
0.7222	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3026	Approved
0.7211	Intermediate Similarity	NPD3023	Approved
0.7205	Intermediate Similarity	NPD6799	Approved
0.7204	Intermediate Similarity	NPD7697	Approved
0.7204	Intermediate Similarity	NPD7435	Discontinued
0.7204	Intermediate Similarity	NPD7698	Approved
0.7204	Intermediate Similarity	NPD7696	Phase 3
0.72	Intermediate Similarity	NPD3094	Phase 2
0.72	Intermediate Similarity	NPD7251	Discontinued
0.7197	Intermediate Similarity	NPD6100	Approved
0.7197	Intermediate Similarity	NPD6099	Approved
0.7192	Intermediate Similarity	NPD3025	Approved
0.7192	Intermediate Similarity	NPD1651	Approved
0.7192	Intermediate Similarity	NPD3024	Approved
0.7186	Intermediate Similarity	NPD3817	Phase 2
0.7186	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6212	Phase 3
0.7182	Intermediate Similarity	NPD6213	Phase 3
0.7182	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7176	Intermediate Similarity	NPD8127	Discontinued
0.7168	Intermediate Similarity	NPD7228	Approved
0.7166	Intermediate Similarity	NPD7871	Phase 2
0.7166	Intermediate Similarity	NPD7870	Phase 2
0.7162	Intermediate Similarity	NPD3092	Approved
0.716	Intermediate Similarity	NPD5401	Approved
0.7159	Intermediate Similarity	NPD7808	Phase 3
0.7152	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD7236	Approved
0.7134	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4625	Phase 3
0.7124	Intermediate Similarity	NPD7008	Discontinued
0.7105	Intermediate Similarity	NPD2861	Phase 2
0.7078	Intermediate Similarity	NPD2313	Discontinued
0.7069	Intermediate Similarity	NPD7177	Discontinued
0.7067	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7701	Phase 2
0.7049	Intermediate Similarity	NPD4360	Phase 2
0.7049	Intermediate Similarity	NPD4363	Phase 3
0.7047	Intermediate Similarity	NPD1281	Approved
0.7047	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3787	Discontinued
0.7035	Intermediate Similarity	NPD7229	Phase 3
0.7031	Intermediate Similarity	NPD7801	Approved
0.7027	Intermediate Similarity	NPD3095	Discontinued
0.7027	Intermediate Similarity	NPD4626	Approved
0.7025	Intermediate Similarity	NPD7033	Discontinued
0.7016	Intermediate Similarity	NPD8151	Discontinued
0.7013	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7741	Discontinued
0.7007	Intermediate Similarity	NPD9545	Approved
0.7006	Intermediate Similarity	NPD4097	Suspended
0.6994	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4140	Approved
0.6987	Remote Similarity	NPD4060	Phase 1
0.6987	Remote Similarity	NPD2979	Phase 3
0.6981	Remote Similarity	NPD2438	Suspended
0.6979	Remote Similarity	NPD7874	Approved
0.6979	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6190	Approved
0.6975	Remote Similarity	NPD2309	Approved
0.6974	Remote Similarity	NPD2797	Approved
0.6974	Remote Similarity	NPD1203	Approved
0.6971	Remote Similarity	NPD3751	Discontinued
0.697	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.697	Remote Similarity	NPD920	Approved
0.6968	Remote Similarity	NPD3268	Approved
0.6968	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1243	Approved
0.6957	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5953	Discontinued
0.6948	Remote Similarity	NPD6832	Phase 2
0.6947	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5124	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