NPASS Compound

Structure

NPC91019 OpenBabel07101718322D 25 29 0 0 1 0 0 0 0 0999 V2000 -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 1.8220 -0.1365 0.0000 C 0 0 1 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 -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 2.8108 0.0125 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 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 9 1 0 0 0 0 3 11 2 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 18 2 0 0 0 0 9 16 1 0 0 0 0 9 17 2 0 0 0 0 10 6 1 1 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 21 1 0 0 0 0 12 19 2 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 23 2 0 0 0 0 14 19 1 0 0 0 0 14 24 1 6 0 0 0 15 20 1 0 0 0 0 15 25 1 1 0 0 0 16 20 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.1
Volume:	334.553
LogP:	3.397
LogD:	1.549
LogS:	-5.027
# Rotatable Bonds:	0
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	3.906
Fsp3:	0.3
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:	-5.565
MDCK Permeability:	1.2108166629332118e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.186
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	94.18981170654297%
Volume Distribution (VD):	1.156
Pgp-substrate:	3.4379494190216064%

ADMET: Metabolism

CYP1A2-inhibitor:	0.134
CYP1A2-substrate:	0.824
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.288
CYP2C9-inhibitor:	0.593
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.272
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.24
CYP3A4-substrate:	0.39

ADMET: Excretion

Clearance (CL):	3.817
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.184
Human Hepatotoxicity (H-HT):	0.267
Drug-inuced Liver Injury (DILI):	0.53
AMES Toxicity:	0.725
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.403
Carcinogencity:	0.072
Eye Corrosion:	0.003
Eye Irritation:	0.138
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC91019

Natural Product ID:	NPC91019
*Common Name:**	Hypoxylonol C
IUPAC Name:	n.a.
Synonyms:	Hypoxylonol C
Standard InCHIKey:	PBYZCDIEUANPBF-ONERCXAPSA-N
Standard InCHI:	InChI=1S/C20H16O5/c21-11-3-1-2-9-16-10(6-13(23)17(9)11)8-4-5-12(22)19-14(24)7-15(25)20(16)18(8)19/h1-5,10,14-15,21-22,24-25H,6-7H2/t10-,14+,15+/m1/s1
SMILES:	O[C@H]1C[C@H](O)c2c3C1=C1c4cccc(c4C(=O)C[C@@H]1c3ccc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1950968
PubChem CID:	57333865
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	=	21000.0	nM	PMID[520392]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16000.0	nM	PMID[520392]

☑ 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 NPC91019 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	340
0.1-0.2	1325
0.2-0.3	2719
0.3-0.4	7798
0.4-0.5	11635
0.5-0.6	4515
0.6-0.7	8133
0.7-0.8	5441
0.8-0.85	639
0.85-0.9	138
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC106519
0.9571	High Similarity	NPC162751
0.9571	High Similarity	NPC52161
0.9504	High Similarity	NPC290695
0.9504	High Similarity	NPC106524
0.8944	High Similarity	NPC85310
0.8912	High Similarity	NPC477276
0.8873	High Similarity	NPC477275
0.8811	High Similarity	NPC474961
0.8811	High Similarity	NPC469520
0.8811	High Similarity	NPC135524
0.8776	High Similarity	NPC477221
0.875	High Similarity	NPC313047
0.875	High Similarity	NPC451542
0.875	High Similarity	NPC295712
0.875	High Similarity	NPC474203
0.8741	High Similarity	NPC204045
0.8741	High Similarity	NPC305845
0.8705	High Similarity	NPC314048
0.8696	High Similarity	NPC474517
0.8696	High Similarity	NPC72669
0.8681	High Similarity	NPC137649
0.8671	High Similarity	NPC169452
0.8671	High Similarity	NPC181560
0.8662	High Similarity	NPC20210
0.8652	High Similarity	NPC191976
0.8643	High Similarity	NPC161964
0.8643	High Similarity	NPC287604
0.8643	High Similarity	NPC472262
0.8639	High Similarity	NPC290194
0.8621	High Similarity	NPC293545
0.8621	High Similarity	NPC174905
0.8601	High Similarity	NPC138099
0.8601	High Similarity	NPC190457
0.8601	High Similarity	NPC242994
0.8592	High Similarity	NPC62272
0.8582	High Similarity	NPC283088
0.8571	High Similarity	NPC267205
0.8571	High Similarity	NPC314437
0.8571	High Similarity	NPC143685
0.8562	High Similarity	NPC84568
0.8562	High Similarity	NPC10764
0.8562	High Similarity	NPC48130
0.8562	High Similarity	NPC300684
0.8562	High Similarity	NPC471906
0.8562	High Similarity	NPC244691
0.8562	High Similarity	NPC218866
0.8552	High Similarity	NPC193555
0.8551	High Similarity	NPC99731
0.8543	High Similarity	NPC474824
0.8543	High Similarity	NPC470408
0.8543	High Similarity	NPC182921
0.8543	High Similarity	NPC218870
0.8511	High Similarity	NPC474394
0.8511	High Similarity	NPC44437
0.8511	High Similarity	NPC166480
0.8511	High Similarity	NPC282780
0.8503	High Similarity	NPC170055
0.8503	High Similarity	NPC34482
0.85	High Similarity	NPC70622
0.85	High Similarity	NPC175738
0.8493	Intermediate Similarity	NPC296752
0.8489	Intermediate Similarity	NPC31799
0.8483	Intermediate Similarity	NPC246638
0.8483	Intermediate Similarity	NPC187843
0.8477	Intermediate Similarity	NPC478220
0.8462	Intermediate Similarity	NPC471905
0.8462	Intermediate Similarity	NPC53206
0.8462	Intermediate Similarity	NPC53414
0.8462	Intermediate Similarity	NPC305060
0.8456	Intermediate Similarity	NPC173978
0.8446	Intermediate Similarity	NPC472134
0.8446	Intermediate Similarity	NPC470570
0.844	Intermediate Similarity	NPC115458
0.844	Intermediate Similarity	NPC52407
0.844	Intermediate Similarity	NPC40524
0.844	Intermediate Similarity	NPC213485
0.844	Intermediate Similarity	NPC139074
0.8435	Intermediate Similarity	NPC227841
0.8435	Intermediate Similarity	NPC193703
0.8435	Intermediate Similarity	NPC48762
0.8435	Intermediate Similarity	NPC21599
0.8431	Intermediate Similarity	NPC474861
0.8429	Intermediate Similarity	NPC93015
0.8429	Intermediate Similarity	NPC475042
0.8425	Intermediate Similarity	NPC73061
0.8417	Intermediate Similarity	NPC92624
0.8414	Intermediate Similarity	NPC96421
0.8403	Intermediate Similarity	NPC13715
0.8394	Intermediate Similarity	NPC103540
0.8392	Intermediate Similarity	NPC254847
0.8392	Intermediate Similarity	NPC193358
0.8392	Intermediate Similarity	NPC118919
0.8389	Intermediate Similarity	NPC215593
0.8389	Intermediate Similarity	NPC472135
0.8378	Intermediate Similarity	NPC12402
0.8369	Intermediate Similarity	NPC58685
0.8357	Intermediate Similarity	NPC259942
0.8357	Intermediate Similarity	NPC136588
0.8357	Intermediate Similarity	NPC199253
0.8357	Intermediate Similarity	NPC147757
0.8345	Intermediate Similarity	NPC162939
0.8345	Intermediate Similarity	NPC282923
0.8345	Intermediate Similarity	NPC48248
0.8333	Intermediate Similarity	NPC474110
0.8333	Intermediate Similarity	NPC142846
0.8333	Intermediate Similarity	NPC44960
0.8333	Intermediate Similarity	NPC245923
0.8333	Intermediate Similarity	NPC53001
0.8323	Intermediate Similarity	NPC195167
0.8322	Intermediate Similarity	NPC61153
0.8322	Intermediate Similarity	NPC283590
0.8322	Intermediate Similarity	NPC147250
0.8322	Intermediate Similarity	NPC70859
0.8322	Intermediate Similarity	NPC85393
0.8322	Intermediate Similarity	NPC130899
0.8322	Intermediate Similarity	NPC110882
0.8322	Intermediate Similarity	NPC285122
0.8322	Intermediate Similarity	NPC271944
0.8321	Intermediate Similarity	NPC234890
0.8321	Intermediate Similarity	NPC74507
0.8301	Intermediate Similarity	NPC478218
0.8299	Intermediate Similarity	NPC477209
0.8299	Intermediate Similarity	NPC239136
0.8299	Intermediate Similarity	NPC257644
0.8299	Intermediate Similarity	NPC19631
0.8298	Intermediate Similarity	NPC85342
0.8298	Intermediate Similarity	NPC244699
0.8298	Intermediate Similarity	NPC41847
0.8289	Intermediate Similarity	NPC470569
0.8288	Intermediate Similarity	NPC225243
0.8278	Intermediate Similarity	NPC329933
0.8276	Intermediate Similarity	NPC87723
0.8269	Intermediate Similarity	NPC292863
0.8269	Intermediate Similarity	NPC184326
0.8267	Intermediate Similarity	NPC37709
0.8264	Intermediate Similarity	NPC474813
0.8264	Intermediate Similarity	NPC272268
0.8261	Intermediate Similarity	NPC87985
0.8255	Intermediate Similarity	NPC478019
0.8252	Intermediate Similarity	NPC12070
0.8248	Intermediate Similarity	NPC198014
0.8248	Intermediate Similarity	NPC375356
0.8243	Intermediate Similarity	NPC471682
0.8243	Intermediate Similarity	NPC478164
0.8239	Intermediate Similarity	NPC246693
0.8239	Intermediate Similarity	NPC110609
0.8239	Intermediate Similarity	NPC478190
0.8239	Intermediate Similarity	NPC242358
0.8235	Intermediate Similarity	NPC474534
0.8235	Intermediate Similarity	NPC196976
0.8235	Intermediate Similarity	NPC474533
0.8228	Intermediate Similarity	NPC290160
0.8224	Intermediate Similarity	NPC205766
0.8224	Intermediate Similarity	NPC255641
0.8224	Intermediate Similarity	NPC470568
0.8224	Intermediate Similarity	NPC290954
0.8219	Intermediate Similarity	NPC143438
0.8217	Intermediate Similarity	NPC137232
0.8217	Intermediate Similarity	NPC18380
0.8214	Intermediate Similarity	NPC473017
0.8207	Intermediate Similarity	NPC477592
0.8205	Intermediate Similarity	NPC324736
0.8205	Intermediate Similarity	NPC186113
0.8201	Intermediate Similarity	NPC71610
0.8201	Intermediate Similarity	NPC267846
0.8201	Intermediate Similarity	NPC3224
0.8194	Intermediate Similarity	NPC290803
0.8194	Intermediate Similarity	NPC80035
0.8194	Intermediate Similarity	NPC249272
0.8188	Intermediate Similarity	NPC79627
0.8188	Intermediate Similarity	NPC68756
0.8188	Intermediate Similarity	NPC152525
0.8188	Intermediate Similarity	NPC477913
0.8182	Intermediate Similarity	NPC472211
0.8182	Intermediate Similarity	NPC53896
0.8182	Intermediate Similarity	NPC78307
0.8182	Intermediate Similarity	NPC225051
0.8182	Intermediate Similarity	NPC114183
0.8176	Intermediate Similarity	NPC471733
0.8175	Intermediate Similarity	NPC283514
0.8175	Intermediate Similarity	NPC300274
0.817	Intermediate Similarity	NPC35
0.817	Intermediate Similarity	NPC476552
0.817	Intermediate Similarity	NPC476551
0.817	Intermediate Similarity	NPC476553
0.8169	Intermediate Similarity	NPC471851
0.8169	Intermediate Similarity	NPC205992
0.8165	Intermediate Similarity	NPC478229
0.8165	Intermediate Similarity	NPC315772
0.8163	Intermediate Similarity	NPC168471
0.8163	Intermediate Similarity	NPC203063
0.8158	Intermediate Similarity	NPC478219
0.8156	Intermediate Similarity	NPC109123
0.8156	Intermediate Similarity	NPC474998
0.8156	Intermediate Similarity	NPC34414
0.8156	Intermediate Similarity	NPC276238
0.8156	Intermediate Similarity	NPC146647
0.8156	Intermediate Similarity	NPC474546
0.8153	Intermediate Similarity	NPC284495

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 NPC91019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	883
0.2-0.3	1351
0.3-0.4	2577
0.4-0.5	2288
0.5-0.6	1173
0.6-0.7	463
0.7-0.8	108
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8592	High Similarity	NPD5408	Approved
0.8592	High Similarity	NPD5406	Approved
0.8592	High Similarity	NPD5405	Approved
0.8592	High Similarity	NPD5404	Approved
0.8507	High Similarity	NPD1201	Approved
0.8435	Intermediate Similarity	NPD7390	Discontinued
0.8394	Intermediate Similarity	NPD1470	Approved
0.8392	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6959	Discontinued
0.7826	Intermediate Similarity	NPD3019	Approved
0.7785	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4380	Phase 2
0.774	Intermediate Similarity	NPD943	Approved
0.7698	Intermediate Similarity	NPD2932	Approved
0.7651	Intermediate Similarity	NPD1510	Phase 2
0.7622	Intermediate Similarity	NPD1164	Approved
0.761	Intermediate Similarity	NPD7819	Suspended
0.761	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2935	Discontinued
0.758	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7473	Discontinued
0.755	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3300	Phase 2
0.7516	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD1549	Phase 2
0.7436	Intermediate Similarity	NPD2534	Approved
0.7436	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2533	Approved
0.7436	Intermediate Similarity	NPD2532	Approved
0.7432	Intermediate Similarity	NPD6663	Approved
0.7429	Intermediate Similarity	NPD3091	Approved
0.7417	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7003	Approved
0.7403	Intermediate Similarity	NPD3750	Approved
0.74	Intermediate Similarity	NPD1607	Approved
0.7397	Intermediate Similarity	NPD5736	Approved
0.7394	Intermediate Similarity	NPD3023	Approved
0.7394	Intermediate Similarity	NPD3026	Approved
0.7386	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1240	Approved
0.7379	Intermediate Similarity	NPD3094	Phase 2
0.7376	Intermediate Similarity	NPD3025	Approved
0.7376	Intermediate Similarity	NPD3024	Approved
0.7375	Intermediate Similarity	NPD7411	Suspended
0.7368	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD8313	Approved
0.7365	Intermediate Similarity	NPD3764	Approved
0.7346	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3092	Approved
0.7329	Intermediate Similarity	NPD1934	Approved
0.7305	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6166	Phase 2
0.7278	Intermediate Similarity	NPD5844	Phase 1
0.7273	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3749	Approved
0.7256	Intermediate Similarity	NPD7075	Discontinued
0.7255	Intermediate Similarity	NPD2796	Approved
0.7251	Intermediate Similarity	NPD6559	Discontinued
0.725	Intermediate Similarity	NPD3226	Approved
0.7241	Intermediate Similarity	NPD8150	Discontinued
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2346	Discontinued
0.7203	Intermediate Similarity	NPD3095	Discontinued
0.719	Intermediate Similarity	NPD2799	Discontinued
0.7179	Intermediate Similarity	NPD8166	Discontinued
0.7178	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1511	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7118	Intermediate Similarity	NPD3818	Discontinued
0.7117	Intermediate Similarity	NPD6801	Discontinued
0.7117	Intermediate Similarity	NPD37	Approved
0.7115	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6535	Approved
0.7095	Intermediate Similarity	NPD2798	Approved
0.7095	Intermediate Similarity	NPD6534	Approved
0.7091	Intermediate Similarity	NPD3882	Suspended
0.7078	Intermediate Similarity	NPD3748	Approved
0.7076	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1876	Approved
0.7073	Intermediate Similarity	NPD2801	Approved
0.707	Intermediate Similarity	NPD3400	Discontinued
0.7063	Intermediate Similarity	NPD1512	Approved
0.7062	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7074	Phase 3
0.7032	Intermediate Similarity	NPD1551	Phase 2
0.703	Intermediate Similarity	NPD5402	Approved
0.7025	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5403	Approved
0.7014	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2342	Discontinued
0.6995	Remote Similarity	NPD6777	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD6782	Approved
0.6995	Remote Similarity	NPD6780	Approved
0.6995	Remote Similarity	NPD6781	Approved
0.6995	Remote Similarity	NPD6776	Approved
0.6988	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4966	Approved
0.6988	Remote Similarity	NPD4967	Phase 2
0.6988	Remote Similarity	NPD4965	Approved
0.698	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7700	Phase 2
0.6978	Remote Similarity	NPD7699	Phase 2
0.6977	Remote Similarity	NPD7054	Approved
0.6977	Remote Similarity	NPD6020	Phase 2
0.6966	Remote Similarity	NPD4059	Approved
0.6962	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1283	Approved
0.6957	Remote Similarity	NPD74	Approved
0.6957	Remote Similarity	NPD9266	Approved
0.6948	Remote Similarity	NPD6651	Approved
0.6936	Remote Similarity	NPD4956	Approved
0.6936	Remote Similarity	NPD7472	Approved
0.6935	Remote Similarity	NPD8319	Approved
0.6935	Remote Similarity	NPD8320	Phase 1
0.6923	Remote Similarity	NPD9493	Approved
0.6923	Remote Similarity	NPD8127	Discontinued
0.6919	Remote Similarity	NPD6823	Phase 2
0.6914	Remote Similarity	NPD5028	Approved
0.6914	Remote Similarity	NPD5034	Approved
0.6914	Remote Similarity	NPD4954	Approved
0.6914	Remote Similarity	NPD5026	Approved
0.6914	Remote Similarity	NPD4955	Approved
0.6914	Remote Similarity	NPD36	Approved
0.6908	Remote Similarity	NPD2313	Discontinued
0.6906	Remote Similarity	NPD4750	Phase 3
0.6905	Remote Similarity	NPD6234	Discontinued
0.6901	Remote Similarity	NPD5951	Approved
0.6899	Remote Similarity	NPD2800	Approved
0.6897	Remote Similarity	NPD1651	Approved
0.6897	Remote Similarity	NPD6797	Phase 2
0.6894	Remote Similarity	NPD5401	Approved
0.6893	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6599	Discontinued
0.6887	Remote Similarity	NPD4908	Phase 1
0.6884	Remote Similarity	NPD9263	Approved
0.6884	Remote Similarity	NPD9264	Approved
0.6884	Remote Similarity	NPD9267	Approved
0.6882	Remote Similarity	NPD7435	Discontinued
0.6882	Remote Similarity	NPD5710	Approved
0.6882	Remote Similarity	NPD7697	Approved
0.6882	Remote Similarity	NPD7696	Phase 3
0.6882	Remote Similarity	NPD5711	Approved
0.6882	Remote Similarity	NPD7698	Approved
0.6879	Remote Similarity	NPD2344	Approved
0.6879	Remote Similarity	NPD7635	Approved
0.6875	Remote Similarity	NPD5035	Approved
0.6875	Remote Similarity	NPD7236	Approved
0.6871	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5760	Phase 2
0.6867	Remote Similarity	NPD5761	Phase 2
0.6857	Remote Similarity	NPD5039	Approved
0.6857	Remote Similarity	NPD5030	Phase 2
0.6857	Remote Similarity	NPD7251	Discontinued
0.6855	Remote Similarity	NPD4628	Phase 3
0.6854	Remote Similarity	NPD5037	Approved
0.6854	Remote Similarity	NPD5038	Approved
0.6851	Remote Similarity	NPD6212	Phase 3
0.6851	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6213	Phase 3
0.6845	Remote Similarity	NPD7871	Phase 2
0.6845	Remote Similarity	NPD7870	Phase 2
0.6842	Remote Similarity	NPD7008	Discontinued
0.6832	Remote Similarity	NPD6799	Approved
0.6831	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3817	Phase 2
0.6824	Remote Similarity	NPD7199	Phase 2
0.6821	Remote Similarity	NPD2861	Phase 2
0.6821	Remote Similarity	NPD7228	Approved
0.6818	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7808	Phase 3
0.6815	Remote Similarity	NPD6099	Approved
0.6815	Remote Similarity	NPD6100	Approved
0.6813	Remote Similarity	NPD6190	Approved
0.68	Remote Similarity	NPD1203	Approved
0.68	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5036	Approved
0.6788	Remote Similarity	NPD1237	Approved
0.6784	Remote Similarity	NPD3787	Discontinued
0.6779	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7610	Discontinued
0.6757	Remote Similarity	NPD1281	Approved
0.675	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD3020	Approved
0.6738	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7701	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