NPASS Compound

Structure

CID10764 OpenBabel06191715342D 40 43 0 0 0 0 0 0 0 0999 V2000 0.8275 -1.4333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6551 1.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6203 0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1377 -0.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4478 -1.4333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9652 1.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6203 -1.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1377 2.3889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4826 -1.4333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6551 -0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8275 1.4333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6203 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1377 0.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4478 -0.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9652 0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7927 -1.4333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3101 1.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3101 -0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8275 1.4333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6551 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8275 0.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7927 -0.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3101 0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3101 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8275 0.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4826 0.4778 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 4.1377 0.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6551 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2754 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7927 0.4778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9652 -1.9111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4826 2.3889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1377 -1.4333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6551 1.9111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4826 1.4333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1377 1.4333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6551 -0.9556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 8 2 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 16 2 0 0 0 0 14 24 1 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 23 2 0 0 0 0 17 33 1 0 0 0 0 18 24 2 0 0 0 0 18 34 1 0 0 0 0 19 25 2 0 0 0 0 19 35 1 0 0 0 0 20 26 2 0 0 0 0 20 36 1 0 0 0 0 21 22 1 0 0 0 0 21 27 2 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 29 1 0 0 0 0 26 28 1 0 0 0 0 26 30 1 0 0 0 0 27 37 1 0 0 0 0 28 38 1 0 0 0 0 29 39 2 0 0 0 0 30 40 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	135.05
Volume:	121.262
LogP:	-2.602
LogD:	-1.937
LogS:	-0.224
# Rotatable Bonds:	3
TPSA:	103.78
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	0
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.35
Synthetic Accessibility Score:	3.066
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.07
MDCK Permeability:	0.01980169489979744
Pgp-inhibitor:	0.0
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	10.608977317810059%
Volume Distribution (VD):	0.571
Pgp-substrate:	89.72294616699219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.052

ADMET: Excretion

Clearance (CL):	1.966
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.369
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.055
Carcinogencity:	0.049
Eye Corrosion:	0.009
Eye Irritation:	0.475
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC10764

Natural Product ID:	NPC10764
*Common Name:**	Phomalevone B
IUPAC Name:	[3-[3-(3,6-dihydroxy-2-methylbenzoyl)-2,4-dihydroxy-6-methylphenyl]-2,6-dihydroxy-4-methylphenyl]-(3,6-dihydroxy-2-methylphenyl)methanone
Synonyms:	Phomalevone B
Standard InCHIKey:	QNGZXAWVLALWLX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H26O10/c1-11-9-19(35)25(29(39)23-13(3)15(31)5-7-17(23)33)27(37)21(11)22-12(2)10-20(36)26(28(22)38)30(40)24-14(4)16(32)6-8-18(24)34/h5-10,31-38H,1-4H3
SMILES:	Cc1cc(O)c(c(c1c1c(C)cc(c(c1O)C(=O)c1c(O)ccc(c1C)O)O)O)C(=O)c1c(O)ccc(c1C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1765415
PubChem CID:	52937280
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000325] Biphenols

*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
NPO30877	Phoma	Genus	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11099218]
NPO30877	Phoma	Genus	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11671521]
NPO30877	Phoma	Genus	Didymellaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21247198]
NPO30877	Phoma	Genus	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	38.0	mm	PMID[464769]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	26.0	mm	PMID[464769]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	18.0	mm	PMID[464769]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	18.0	mm	PMID[464769]

☑ 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 NPC10764 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	412
0.1-0.2	1756
0.2-0.3	4093
0.3-0.4	11040
0.4-0.5	7857
0.5-0.6	5185
0.6-0.7	6545
0.7-0.8	5242
0.8-0.85	440
0.85-0.9	99
0.9-0.95	27
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9433	High Similarity	NPC227841
0.9371	High Similarity	NPC37709
0.9236	High Similarity	NPC290194
0.9225	High Similarity	NPC293545
0.9225	High Similarity	NPC296752
0.9225	High Similarity	NPC174905
0.9225	High Similarity	NPC313047
0.9225	High Similarity	NPC451542
0.9225	High Similarity	NPC295712
0.9225	High Similarity	NPC474203
0.922	High Similarity	NPC246638
0.9209	High Similarity	NPC245923
0.9137	High Similarity	NPC474813
0.9097	High Similarity	NPC471683
0.9085	High Similarity	NPC187843
0.9078	High Similarity	NPC143438
0.9078	High Similarity	NPC242994
0.9078	High Similarity	NPC138099
0.9071	High Similarity	NPC44960
0.9071	High Similarity	NPC474110
0.9051	High Similarity	NPC72669
0.9051	High Similarity	NPC474517
0.9034	High Similarity	NPC271944
0.9034	High Similarity	NPC110882
0.9034	High Similarity	NPC85393
0.9021	High Similarity	NPC19631
0.9021	High Similarity	NPC239136
0.9014	High Similarity	NPC181560
0.9014	High Similarity	NPC169452
0.9	High Similarity	NPC191976
0.8986	High Similarity	NPC35
0.898	High Similarity	NPC477221
0.8966	High Similarity	NPC12402
0.8958	High Similarity	NPC471682
0.8936	High Similarity	NPC53206
0.8936	High Similarity	NPC53414
0.8936	High Similarity	NPC62272
0.8936	High Similarity	NPC471905
0.8933	High Similarity	NPC66029
0.8929	High Similarity	NPC283088
0.8921	High Similarity	NPC267205
0.8889	High Similarity	NPC257644
0.8889	High Similarity	NPC193555
0.8889	High Similarity	NPC474961
0.8865	High Similarity	NPC155211
0.8865	High Similarity	NPC254847
0.8857	High Similarity	NPC282780
0.8857	High Similarity	NPC161964
0.8857	High Similarity	NPC166480
0.8857	High Similarity	NPC287604
0.8857	High Similarity	NPC472262
0.8808	High Similarity	NPC66508
0.8808	High Similarity	NPC226656
0.8777	High Similarity	NPC205992
0.8759	High Similarity	NPC135524
0.8758	High Similarity	NPC324736
0.875	High Similarity	NPC225243
0.8732	High Similarity	NPC118919
0.8732	High Similarity	NPC272268
0.8723	High Similarity	NPC44437
0.8701	High Similarity	NPC470342
0.8701	High Similarity	NPC476506
0.8701	High Similarity	NPC472060
0.8701	High Similarity	NPC472052
0.8696	High Similarity	NPC48248
0.869	High Similarity	NPC204045
0.869	High Similarity	NPC305845
0.8681	High Similarity	NPC190457
0.8671	High Similarity	NPC53001
0.8667	High Similarity	NPC205766
0.8662	High Similarity	NPC161632
0.8652	High Similarity	NPC225051
0.8652	High Similarity	NPC314048
0.8639	High Similarity	NPC471906
0.8639	High Similarity	NPC193703
0.8639	High Similarity	NPC21599
0.8639	High Similarity	NPC244691
0.8636	High Similarity	NPC177650
0.8633	High Similarity	NPC99731
0.8633	High Similarity	NPC92624
0.8618	High Similarity	NPC470408
0.8618	High Similarity	NPC182921
0.8618	High Similarity	NPC218870
0.8618	High Similarity	NPC474824
0.8611	High Similarity	NPC13715
0.8611	High Similarity	NPC87723
0.8592	High Similarity	NPC12070
0.8582	High Similarity	NPC175738
0.8581	High Similarity	NPC312993
0.8581	High Similarity	NPC186325
0.8581	High Similarity	NPC34482
0.8581	High Similarity	NPC68441
0.8571	High Similarity	NPC259942
0.8571	High Similarity	NPC238629
0.8562	High Similarity	NPC106519
0.8562	High Similarity	NPC91019
0.8562	High Similarity	NPC110810
0.8562	High Similarity	NPC290550
0.8561	High Similarity	NPC282923
0.8543	High Similarity	NPC315520
0.8543	High Similarity	NPC294646
0.8542	High Similarity	NPC305060
0.854	High Similarity	NPC173978
0.8535	High Similarity	NPC476505
0.8531	High Similarity	NPC249272
0.8526	High Similarity	NPC273467
0.8526	High Similarity	NPC189552
0.8523	High Similarity	NPC470570
0.8521	High Similarity	NPC114183
0.8521	High Similarity	NPC115458
0.8514	High Similarity	NPC48762
0.8511	High Similarity	NPC244699
0.8511	High Similarity	NPC85342
0.8506	High Similarity	NPC474861
0.8503	High Similarity	NPC85310
0.8503	High Similarity	NPC73061
0.8503	High Similarity	NPC137649
0.8497	Intermediate Similarity	NPC135522
0.8483	Intermediate Similarity	NPC20210
0.8481	Intermediate Similarity	NPC71390
0.8477	Intermediate Similarity	NPC329933
0.8467	Intermediate Similarity	NPC34802
0.8462	Intermediate Similarity	NPC270899
0.8462	Intermediate Similarity	NPC50924
0.8451	Intermediate Similarity	NPC58685
0.8447	Intermediate Similarity	NPC477836
0.8442	Intermediate Similarity	NPC254351
0.844	Intermediate Similarity	NPC55949
0.844	Intermediate Similarity	NPC31539
0.8435	Intermediate Similarity	NPC477275
0.8428	Intermediate Similarity	NPC30027
0.8421	Intermediate Similarity	NPC227122
0.8417	Intermediate Similarity	NPC160499
0.8417	Intermediate Similarity	NPC96915
0.8417	Intermediate Similarity	NPC267846
0.8403	Intermediate Similarity	NPC80035
0.8403	Intermediate Similarity	NPC290803
0.84	Intermediate Similarity	NPC143685
0.84	Intermediate Similarity	NPC147250
0.84	Intermediate Similarity	NPC314437
0.84	Intermediate Similarity	NPC476535
0.8397	Intermediate Similarity	NPC186113
0.8397	Intermediate Similarity	NPC18699
0.8397	Intermediate Similarity	NPC55443
0.8392	Intermediate Similarity	NPC180261
0.8392	Intermediate Similarity	NPC37299
0.8392	Intermediate Similarity	NPC53896
0.8378	Intermediate Similarity	NPC469520
0.8377	Intermediate Similarity	NPC329844
0.8377	Intermediate Similarity	NPC472211
0.8377	Intermediate Similarity	NPC95842
0.8377	Intermediate Similarity	NPC280530
0.8377	Intermediate Similarity	NPC178964
0.8369	Intermediate Similarity	NPC34414
0.8369	Intermediate Similarity	NPC146647
0.8369	Intermediate Similarity	NPC474998
0.8369	Intermediate Similarity	NPC109123
0.8367	Intermediate Similarity	NPC203063
0.8367	Intermediate Similarity	NPC96421
0.8365	Intermediate Similarity	NPC469664
0.8357	Intermediate Similarity	NPC72158
0.8357	Intermediate Similarity	NPC23126
0.8357	Intermediate Similarity	NPC98254
0.8357	Intermediate Similarity	NPC116513
0.8357	Intermediate Similarity	NPC103356
0.8357	Intermediate Similarity	NPC266689
0.8357	Intermediate Similarity	NPC30501
0.8357	Intermediate Similarity	NPC162612
0.8357	Intermediate Similarity	NPC471530
0.8357	Intermediate Similarity	NPC105157
0.8357	Intermediate Similarity	NPC190043
0.8357	Intermediate Similarity	NPC169250
0.8357	Intermediate Similarity	NPC100067
0.8356	Intermediate Similarity	NPC473622
0.8356	Intermediate Similarity	NPC123714
0.8356	Intermediate Similarity	NPC4214
0.8354	Intermediate Similarity	NPC15374
0.8345	Intermediate Similarity	NPC477454
0.8345	Intermediate Similarity	NPC103540
0.8344	Intermediate Similarity	NPC245584
0.8344	Intermediate Similarity	NPC289042
0.8344	Intermediate Similarity	NPC312929
0.8344	Intermediate Similarity	NPC162751
0.8344	Intermediate Similarity	NPC52161
0.8344	Intermediate Similarity	NPC56433
0.8344	Intermediate Similarity	NPC126767
0.8344	Intermediate Similarity	NPC284495
0.8344	Intermediate Similarity	NPC118027
0.8344	Intermediate Similarity	NPC190648
0.8333	Intermediate Similarity	NPC44199
0.8323	Intermediate Similarity	NPC318270
0.8322	Intermediate Similarity	NPC84266
0.8322	Intermediate Similarity	NPC70622
0.8321	Intermediate Similarity	NPC196976
0.8313	Intermediate Similarity	NPC477835
0.8312	Intermediate Similarity	NPC175978
0.8311	Intermediate Similarity	NPC92079
0.8311	Intermediate Similarity	NPC124365
0.8301	Intermediate Similarity	NPC147735
0.8301	Intermediate Similarity	NPC255641

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 NPC10764 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	984
0.2-0.3	1442
0.3-0.4	2965
0.4-0.5	1999
0.5-0.6	983
0.6-0.7	311
0.7-0.8	77
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9433	High Similarity	NPD7390	Discontinued
0.8936	High Similarity	NPD5405	Approved
0.8936	High Similarity	NPD5406	Approved
0.8936	High Similarity	NPD5404	Approved
0.8936	High Similarity	NPD5408	Approved
0.8865	High Similarity	NPD1509	Clinical (unspecified phase)
0.8581	High Similarity	NPD7422	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6959	Discontinued
0.8345	Intermediate Similarity	NPD1470	Approved
0.8321	Intermediate Similarity	NPD1201	Approved
0.8239	Intermediate Similarity	NPD6232	Discontinued
0.8199	Intermediate Similarity	NPD7473	Discontinued
0.7945	Intermediate Similarity	NPD943	Approved
0.7857	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7768	Phase 2
0.78	Intermediate Similarity	NPD2935	Discontinued
0.775	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7819	Suspended
0.7665	Intermediate Similarity	NPD5844	Phase 1
0.7658	Intermediate Similarity	NPD3226	Approved
0.7654	Intermediate Similarity	NPD3749	Approved
0.763	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2533	Approved
0.7628	Intermediate Similarity	NPD2532	Approved
0.7628	Intermediate Similarity	NPD2534	Approved
0.761	Intermediate Similarity	NPD4380	Phase 2
0.76	Intermediate Similarity	NPD1607	Approved
0.7586	Intermediate Similarity	NPD1164	Approved
0.7578	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2801	Approved
0.7562	Intermediate Similarity	NPD7411	Suspended
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3750	Approved
0.7484	Intermediate Similarity	NPD7003	Approved
0.7467	Intermediate Similarity	NPD1240	Approved
0.7443	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6559	Discontinued
0.7413	Intermediate Similarity	NPD3019	Approved
0.7386	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6166	Phase 2
0.7381	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5494	Approved
0.7342	Intermediate Similarity	NPD1511	Approved
0.7341	Intermediate Similarity	NPD8312	Approved
0.7341	Intermediate Similarity	NPD8313	Approved
0.7338	Intermediate Similarity	NPD7635	Approved
0.7333	Intermediate Similarity	NPD3764	Approved
0.7301	Intermediate Similarity	NPD1934	Approved
0.7292	Intermediate Similarity	NPD2932	Approved
0.729	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6535	Approved
0.7263	Intermediate Similarity	NPD6534	Approved
0.725	Intermediate Similarity	NPD1512	Approved
0.7244	Intermediate Similarity	NPD1549	Phase 2
0.7229	Intermediate Similarity	NPD7075	Discontinued
0.7226	Intermediate Similarity	NPD2342	Discontinued
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8150	Discontinued
0.7212	Intermediate Similarity	NPD5402	Approved
0.7197	Intermediate Similarity	NPD2800	Approved
0.7169	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3748	Approved
0.7161	Intermediate Similarity	NPD2799	Discontinued
0.7158	Intermediate Similarity	NPD6778	Approved
0.7158	Intermediate Similarity	NPD6781	Approved
0.7158	Intermediate Similarity	NPD6782	Approved
0.7158	Intermediate Similarity	NPD6780	Approved
0.7158	Intermediate Similarity	NPD6779	Approved
0.7158	Intermediate Similarity	NPD6777	Approved
0.7158	Intermediate Similarity	NPD6776	Approved
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD7699	Phase 2
0.7126	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4750	Phase 3
0.7115	Intermediate Similarity	NPD2796	Approved
0.7097	Intermediate Similarity	NPD7870	Phase 2
0.7097	Intermediate Similarity	NPD7871	Phase 2
0.7081	Intermediate Similarity	NPD6823	Phase 2
0.707	Intermediate Similarity	NPD2344	Approved
0.7066	Intermediate Similarity	NPD3882	Suspended
0.7059	Intermediate Similarity	NPD5710	Approved
0.7059	Intermediate Similarity	NPD5711	Approved
0.7052	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6020	Phase 2
0.7048	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1465	Phase 2
0.7043	Intermediate Similarity	NPD7696	Phase 3
0.7043	Intermediate Similarity	NPD7698	Approved
0.7043	Intermediate Similarity	NPD7435	Discontinued
0.7043	Intermediate Similarity	NPD7697	Approved
0.7037	Intermediate Similarity	NPD8151	Discontinued
0.7032	Intermediate Similarity	NPD6651	Approved
0.7017	Intermediate Similarity	NPD6213	Phase 3
0.7017	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6212	Phase 3
0.7011	Intermediate Similarity	NPD7074	Phase 3
0.7007	Intermediate Similarity	NPD3026	Approved
0.7007	Intermediate Similarity	NPD3023	Approved
0.7006	Intermediate Similarity	NPD1551	Phase 2
0.7006	Intermediate Similarity	NPD3817	Phase 2
0.7006	Intermediate Similarity	NPD6100	Approved
0.7006	Intermediate Similarity	NPD6099	Approved
0.6994	Remote Similarity	NPD3818	Discontinued
0.6993	Remote Similarity	NPD2313	Discontinued
0.6993	Remote Similarity	NPD5951	Approved
0.6993	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD37	Approved
0.6988	Remote Similarity	NPD6801	Discontinued
0.6986	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3025	Approved
0.6986	Remote Similarity	NPD1651	Approved
0.6986	Remote Similarity	NPD3024	Approved
0.6981	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6599	Discontinued
0.6954	Remote Similarity	NPD7054	Approved
0.6954	Remote Similarity	NPD2798	Approved
0.6939	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1283	Approved
0.6914	Remote Similarity	NPD7472	Approved
0.6913	Remote Similarity	NPD9269	Phase 2
0.6909	Remote Similarity	NPD7458	Discontinued
0.6905	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7177	Discontinued
0.6895	Remote Similarity	NPD7701	Phase 2
0.6894	Remote Similarity	NPD2309	Approved
0.6882	Remote Similarity	NPD6234	Discontinued
0.6878	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7783	Phase 2
0.6875	Remote Similarity	NPD497	Approved
0.6875	Remote Similarity	NPD6797	Phase 2
0.6871	Remote Similarity	NPD9268	Approved
0.6864	Remote Similarity	NPD4965	Approved
0.6864	Remote Similarity	NPD4966	Approved
0.6864	Remote Similarity	NPD4967	Phase 2
0.6863	Remote Similarity	NPD4908	Phase 1
0.6861	Remote Similarity	NPD940	Approved
0.6861	Remote Similarity	NPD846	Approved
0.686	Remote Similarity	NPD7229	Phase 3
0.6839	Remote Similarity	NPD5033	Approved
0.6836	Remote Similarity	NPD5031	Approved
0.6836	Remote Similarity	NPD5027	Approved
0.6836	Remote Similarity	NPD5029	Approved
0.6836	Remote Similarity	NPD7251	Discontinued
0.6832	Remote Similarity	NPD8166	Discontinued
0.6832	Remote Similarity	NPD3400	Discontinued
0.6825	Remote Similarity	NPD8320	Phase 1
0.6825	Remote Similarity	NPD8319	Approved
0.6824	Remote Similarity	NPD2286	Discontinued
0.6823	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7874	Approved
0.6821	Remote Similarity	NPD3926	Phase 2
0.6818	Remote Similarity	NPD7008	Discontinued
0.681	Remote Similarity	NPD6799	Approved
0.6809	Remote Similarity	NPD74	Approved
0.6809	Remote Similarity	NPD9266	Approved
0.6806	Remote Similarity	NPD496	Approved
0.6806	Remote Similarity	NPD495	Approved
0.6806	Remote Similarity	NPD498	Approved
0.6802	Remote Similarity	NPD1247	Approved
0.6798	Remote Similarity	NPD4954	Approved
0.6798	Remote Similarity	NPD5028	Approved
0.6798	Remote Similarity	NPD4955	Approved
0.6798	Remote Similarity	NPD7808	Phase 3
0.6798	Remote Similarity	NPD5034	Approved
0.6798	Remote Similarity	NPD36	Approved
0.6798	Remote Similarity	NPD5026	Approved
0.6788	Remote Similarity	NPD5403	Approved
0.6788	Remote Similarity	NPD920	Approved
0.6788	Remote Similarity	NPD7801	Approved
0.6788	Remote Similarity	NPD1242	Phase 1
0.6788	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7654	Discontinued
0.6781	Remote Similarity	NPD9493	Approved
0.678	Remote Similarity	NPD5953	Discontinued
0.677	Remote Similarity	NPD1243	Approved
0.6768	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3787	Discontinued
0.6758	Remote Similarity	NPD4287	Approved
0.6752	Remote Similarity	NPD230	Phase 1
0.6742	Remote Similarity	NPD5030	Phase 2
0.6742	Remote Similarity	NPD5039	Approved
0.674	Remote Similarity	NPD5038	Approved
0.674	Remote Similarity	NPD5037	Approved
0.6738	Remote Similarity	NPD9263	Approved
0.6738	Remote Similarity	NPD9264	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data