NPASS Compound

Structure

NPC285345 OpenBabel07101718242D 31 33 0 0 0 0 0 0 0 0999 V2000 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -3.4641 -3.0000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 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 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 11 1 0 0 0 0 2 5 2 0 0 0 0 2 11 1 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 13 31 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 20 2 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 22 30 2 0 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.08
Volume:	410.873
LogP:	2.765
LogD:	1.413
LogS:	-3.289
# Rotatable Bonds:	5
TPSA:	168.66
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	3.002
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.051
MDCK Permeability:	1.1085954611189663e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.543
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	98.9950180053711%
Volume Distribution (VD):	0.354
Pgp-substrate:	1.5622280836105347%

ADMET: Metabolism

CYP1A2-inhibitor:	0.465
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.365
CYP2C9-substrate:	0.36
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.27
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	5.037
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.209
Human Hepatotoxicity (H-HT):	0.753
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.198
Maximum Recommended Daily Dose:	0.084
Skin Sensitization:	0.913
Carcinogencity:	0.443
Eye Corrosion:	0.003
Eye Irritation:	0.549
Respiratory Toxicity:	0.056

Download Data

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

Natural Product: NPC285345

Natural Product ID:	NPC285345
*Common Name:**	Phellibaumin D
IUPAC Name:	(Z)-3-(3,4-dihydroxyphenyl)-2-[6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2-oxopyran-3-yl]prop-2-enoic acid
Synonyms:	Phellibaumin D
Standard InCHIKey:	HODNKSQSWYYPLV-IHRVKPHJSA-N
Standard InCHI:	InChI=1S/C22H16O9/c23-15-5-2-11(8-17(15)25)1-4-13-10-19(27)20(22(30)31-13)14(21(28)29)7-12-3-6-16(24)18(26)9-12/h1-10,23-27H,(H,28,29)/b4-1+,14-7-
SMILES:	OC(=O)/C(=Cc1ccc(c(c1)O)O)/c1c(O)cc(oc1=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1780027
PubChem CID:	54728960
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0002503] Hydroxycinnamic acids

*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
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20708931]
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21531558]
NPO32484	phellinus baumii	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26077494]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	74620.0	nM	PMID[545414]

☑ 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 NPC285345 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	388
0.1-0.2	2004
0.2-0.3	5656
0.3-0.4	11262
0.4-0.5	5561
0.5-0.6	4448
0.6-0.7	6134
0.7-0.8	6037
0.8-0.85	1116
0.85-0.9	71
0.9-0.95	15
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9831	High Similarity	NPC67951
0.9748	High Similarity	NPC118584
0.9664	High Similarity	NPC197832
0.9661	High Similarity	NPC306100
0.9194	High Similarity	NPC477300
0.8968	High Similarity	NPC329344
0.8968	High Similarity	NPC217052
0.8968	High Similarity	NPC32626
0.8968	High Similarity	NPC237506
0.8966	High Similarity	NPC131530
0.896	High Similarity	NPC167463
0.896	High Similarity	NPC46192
0.8917	High Similarity	NPC263386
0.8917	High Similarity	NPC141791
0.8889	High Similarity	NPC208536
0.8889	High Similarity	NPC64111
0.8862	High Similarity	NPC212541
0.8833	High Similarity	NPC275519
0.8819	High Similarity	NPC285361
0.877	High Similarity	NPC470849
0.877	High Similarity	NPC470848
0.8769	High Similarity	NPC477301
0.8769	High Similarity	NPC311742
0.8699	High Similarity	NPC147654
0.8667	High Similarity	NPC281277
0.8655	High Similarity	NPC328593
0.8655	High Similarity	NPC261453
0.8655	High Similarity	NPC33749
0.8644	High Similarity	NPC51698
0.864	High Similarity	NPC246704
0.8607	High Similarity	NPC241634
0.8583	High Similarity	NPC233669
0.8583	High Similarity	NPC474967
0.8571	High Similarity	NPC289459
0.8571	High Similarity	NPC132921
0.8571	High Similarity	NPC95381
0.8559	High Similarity	NPC226250
0.8525	High Similarity	NPC309434
0.8525	High Similarity	NPC203124
0.8507	High Similarity	NPC471875
0.8504	High Similarity	NPC213552
0.8504	High Similarity	NPC120225
0.8504	High Similarity	NPC168653
0.8504	High Similarity	NPC251407
0.8504	High Similarity	NPC475695
0.85	High Similarity	NPC217472
0.8496	Intermediate Similarity	NPC279676
0.8496	Intermediate Similarity	NPC67349
0.8492	Intermediate Similarity	NPC288945
0.8485	Intermediate Similarity	NPC476870
0.8468	Intermediate Similarity	NPC471877
0.8462	Intermediate Similarity	NPC318799
0.8456	Intermediate Similarity	NPC285550
0.845	Intermediate Similarity	NPC83062
0.845	Intermediate Similarity	NPC94810
0.8448	Intermediate Similarity	NPC1075
0.8448	Intermediate Similarity	NPC294902
0.8448	Intermediate Similarity	NPC1786
0.8444	Intermediate Similarity	NPC9218
0.8413	Intermediate Similarity	NPC106659
0.8413	Intermediate Similarity	NPC18984
0.8413	Intermediate Similarity	NPC229084
0.8413	Intermediate Similarity	NPC160900
0.8409	Intermediate Similarity	NPC106406
0.8403	Intermediate Similarity	NPC297657
0.8397	Intermediate Similarity	NPC25581
0.8397	Intermediate Similarity	NPC18074
0.8397	Intermediate Similarity	NPC61
0.8397	Intermediate Similarity	NPC5419
0.8394	Intermediate Similarity	NPC183824
0.8387	Intermediate Similarity	NPC2058
0.8382	Intermediate Similarity	NPC91546
0.8372	Intermediate Similarity	NPC110313
0.837	Intermediate Similarity	NPC191280
0.837	Intermediate Similarity	NPC179505
0.837	Intermediate Similarity	NPC156709
0.8361	Intermediate Similarity	NPC277394
0.8361	Intermediate Similarity	NPC61062
0.8361	Intermediate Similarity	NPC299252
0.8359	Intermediate Similarity	NPC276014
0.8333	Intermediate Similarity	NPC168799
0.8333	Intermediate Similarity	NPC155209
0.8321	Intermediate Similarity	NPC198388
0.832	Intermediate Similarity	NPC204466
0.832	Intermediate Similarity	NPC189844
0.832	Intermediate Similarity	NPC109083
0.832	Intermediate Similarity	NPC269843
0.832	Intermediate Similarity	NPC224814
0.832	Intermediate Similarity	NPC14007
0.832	Intermediate Similarity	NPC60962
0.8309	Intermediate Similarity	NPC290664
0.8306	Intermediate Similarity	NPC70084
0.8293	Intermediate Similarity	NPC278652
0.8293	Intermediate Similarity	NPC610
0.8293	Intermediate Similarity	NPC200988
0.8293	Intermediate Similarity	NPC145023
0.8293	Intermediate Similarity	NPC175799
0.8293	Intermediate Similarity	NPC65791
0.8284	Intermediate Similarity	NPC120852
0.8284	Intermediate Similarity	NPC90431
0.8271	Intermediate Similarity	NPC287597
0.8271	Intermediate Similarity	NPC34293
0.8271	Intermediate Similarity	NPC886
0.8271	Intermediate Similarity	NPC135127
0.8254	Intermediate Similarity	NPC70752
0.8254	Intermediate Similarity	NPC472271
0.8248	Intermediate Similarity	NPC206095
0.8248	Intermediate Similarity	NPC297517
0.8248	Intermediate Similarity	NPC13818
0.8248	Intermediate Similarity	NPC35702
0.8248	Intermediate Similarity	NPC224389
0.8248	Intermediate Similarity	NPC477335
0.8248	Intermediate Similarity	NPC471027
0.824	Intermediate Similarity	NPC202474
0.8231	Intermediate Similarity	NPC478215
0.8226	Intermediate Similarity	NPC164706
0.8226	Intermediate Similarity	NPC107588
0.8226	Intermediate Similarity	NPC86198
0.8226	Intermediate Similarity	NPC272471
0.8226	Intermediate Similarity	NPC137537
0.8226	Intermediate Similarity	NPC70744
0.822	Intermediate Similarity	NPC260952
0.8203	Intermediate Similarity	NPC146886
0.8203	Intermediate Similarity	NPC60517
0.8203	Intermediate Similarity	NPC20443
0.8201	Intermediate Similarity	NPC258671
0.8201	Intermediate Similarity	NPC53884
0.8189	Intermediate Similarity	NPC286573
0.8188	Intermediate Similarity	NPC43158
0.8188	Intermediate Similarity	NPC258469
0.8188	Intermediate Similarity	NPC319628
0.8188	Intermediate Similarity	NPC220664
0.8188	Intermediate Similarity	NPC192831
0.8188	Intermediate Similarity	NPC303090
0.8188	Intermediate Similarity	NPC37331
0.8188	Intermediate Similarity	NPC284948
0.8188	Intermediate Similarity	NPC277315
0.8188	Intermediate Similarity	NPC472016
0.8168	Intermediate Similarity	NPC241354
0.8168	Intermediate Similarity	NPC229784
0.8168	Intermediate Similarity	NPC477293
0.8168	Intermediate Similarity	NPC477294
0.8167	Intermediate Similarity	NPC183700
0.8162	Intermediate Similarity	NPC37250
0.8162	Intermediate Similarity	NPC142703
0.8162	Intermediate Similarity	NPC219428
0.8162	Intermediate Similarity	NPC302857
0.8162	Intermediate Similarity	NPC152942
0.8162	Intermediate Similarity	NPC278068
0.816	Intermediate Similarity	NPC470214
0.816	Intermediate Similarity	NPC470215
0.816	Intermediate Similarity	NPC109371
0.8156	Intermediate Similarity	NPC1580
0.8156	Intermediate Similarity	NPC17042
0.8156	Intermediate Similarity	NPC155910
0.8154	Intermediate Similarity	NPC476873
0.8154	Intermediate Similarity	NPC276466
0.8154	Intermediate Similarity	NPC123722
0.8154	Intermediate Similarity	NPC151167
0.8154	Intermediate Similarity	NPC123228
0.8154	Intermediate Similarity	NPC5018
0.8148	Intermediate Similarity	NPC471664
0.8148	Intermediate Similarity	NPC471665
0.8148	Intermediate Similarity	NPC470572
0.8129	Intermediate Similarity	NPC470130
0.8129	Intermediate Similarity	NPC304956
0.8125	Intermediate Similarity	NPC224208
0.8125	Intermediate Similarity	NPC474275
0.812	Intermediate Similarity	NPC473285
0.8102	Intermediate Similarity	NPC274891
0.8102	Intermediate Similarity	NPC303683
0.8102	Intermediate Similarity	NPC106055
0.8102	Intermediate Similarity	NPC26241
0.8102	Intermediate Similarity	NPC288452
0.8102	Intermediate Similarity	NPC474875
0.8102	Intermediate Similarity	NPC110699
0.8102	Intermediate Similarity	NPC289690
0.8102	Intermediate Similarity	NPC476819
0.8102	Intermediate Similarity	NPC205751
0.8102	Intermediate Similarity	NPC476820
0.8102	Intermediate Similarity	NPC295492
0.8092	Intermediate Similarity	NPC232880
0.8088	Intermediate Similarity	NPC78363
0.8088	Intermediate Similarity	NPC126206
0.8088	Intermediate Similarity	NPC260425
0.8085	Intermediate Similarity	NPC322660
0.8085	Intermediate Similarity	NPC283081
0.8085	Intermediate Similarity	NPC299090
0.8085	Intermediate Similarity	NPC143892
0.8085	Intermediate Similarity	NPC221383
0.8083	Intermediate Similarity	NPC79543
0.808	Intermediate Similarity	NPC311091
0.808	Intermediate Similarity	NPC471033
0.808	Intermediate Similarity	NPC277460
0.8077	Intermediate Similarity	NPC179777
0.8077	Intermediate Similarity	NPC303680
0.8077	Intermediate Similarity	NPC90128
0.8077	Intermediate Similarity	NPC84076
0.8077	Intermediate Similarity	NPC147192
0.8074	Intermediate Similarity	NPC113295

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 NPC285345 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	1004
0.2-0.3	1827
0.3-0.4	2664
0.4-0.5	1777
0.5-0.6	1048
0.6-0.7	333
0.7-0.8	119
0.8-0.85	21
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8413	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD6190	Approved
0.8029	Intermediate Similarity	NPD7266	Discontinued
0.7857	Intermediate Similarity	NPD5536	Phase 2
0.7787	Intermediate Similarity	NPD3022	Approved
0.7787	Intermediate Similarity	NPD3021	Approved
0.773	Intermediate Similarity	NPD8166	Discontinued
0.7664	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD7095	Approved
0.75	Intermediate Similarity	NPD9269	Phase 2
0.7483	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD9494	Approved
0.7445	Intermediate Similarity	NPD3764	Approved
0.7381	Intermediate Similarity	NPD228	Approved
0.7365	Intermediate Similarity	NPD1653	Approved
0.7339	Intermediate Similarity	NPD1358	Approved
0.7329	Intermediate Similarity	NPD1511	Approved
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2935	Discontinued
0.7315	Intermediate Similarity	NPD3455	Phase 2
0.7299	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1535	Discovery
0.7286	Intermediate Similarity	NPD447	Suspended
0.7259	Intermediate Similarity	NPD3225	Approved
0.7258	Intermediate Similarity	NPD3134	Approved
0.7246	Intermediate Similarity	NPD3027	Phase 3
0.7239	Intermediate Similarity	NPD1481	Phase 2
0.7237	Intermediate Similarity	NPD2801	Approved
0.723	Intermediate Similarity	NPD1512	Approved
0.7226	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4060	Phase 1
0.7214	Intermediate Similarity	NPD943	Approved
0.7206	Intermediate Similarity	NPD2797	Approved
0.7197	Intermediate Similarity	NPD9268	Approved
0.7194	Intermediate Similarity	NPD2313	Discontinued
0.7188	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD2934	Approved
0.7143	Intermediate Similarity	NPD2933	Approved
0.7132	Intermediate Similarity	NPD5283	Phase 1
0.7124	Intermediate Similarity	NPD1465	Phase 2
0.7121	Intermediate Similarity	NPD9545	Approved
0.7099	Intermediate Similarity	NPD7685	Pre-registration
0.7092	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD825	Approved
0.7092	Intermediate Similarity	NPD1613	Approved
0.7092	Intermediate Similarity	NPD826	Approved
0.709	Intermediate Similarity	NPD3847	Discontinued
0.709	Intermediate Similarity	NPD3496	Discontinued
0.7083	Intermediate Similarity	NPD2860	Approved
0.7083	Intermediate Similarity	NPD2859	Approved
0.708	Intermediate Similarity	NPD1203	Approved
0.7078	Intermediate Similarity	NPD3817	Phase 2
0.7071	Intermediate Similarity	NPD6798	Discontinued
0.7071	Intermediate Similarity	NPD3268	Approved
0.7068	Intermediate Similarity	NPD5585	Approved
0.7063	Intermediate Similarity	NPD7097	Phase 1
0.7063	Intermediate Similarity	NPD3818	Discontinued
0.7051	Intermediate Similarity	NPD6234	Discontinued
0.7049	Intermediate Similarity	NPD3020	Approved
0.7042	Intermediate Similarity	NPD4340	Discontinued
0.7029	Intermediate Similarity	NPD257	Approved
0.7029	Intermediate Similarity	NPD258	Approved
0.7025	Intermediate Similarity	NPD6232	Discontinued
0.7015	Intermediate Similarity	NPD4626	Approved
0.7014	Intermediate Similarity	NPD2799	Discontinued
0.7013	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3750	Approved
0.7007	Intermediate Similarity	NPD4628	Phase 3
0.6992	Remote Similarity	NPD1894	Discontinued
0.6992	Remote Similarity	NPD1242	Phase 1
0.698	Remote Similarity	NPD4357	Discontinued
0.6978	Remote Similarity	NPD5736	Approved
0.6978	Remote Similarity	NPD9569	Approved
0.6966	Remote Similarity	NPD6032	Approved
0.696	Remote Similarity	NPD5909	Discontinued
0.6951	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1934	Approved
0.6933	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD555	Phase 2
0.6923	Remote Similarity	NPD3882	Suspended
0.6918	Remote Similarity	NPD2346	Discontinued
0.6912	Remote Similarity	NPD422	Phase 1
0.6905	Remote Similarity	NPD9697	Approved
0.6901	Remote Similarity	NPD4062	Phase 3
0.6901	Remote Similarity	NPD259	Phase 1
0.6899	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4308	Phase 3
0.6894	Remote Similarity	NPD7473	Discontinued
0.6892	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4110	Phase 3
0.6884	Remote Similarity	NPD1283	Approved
0.6863	Remote Similarity	NPD3226	Approved
0.6861	Remote Similarity	NPD1608	Approved
0.6859	Remote Similarity	NPD5402	Approved
0.685	Remote Similarity	NPD968	Approved
0.6842	Remote Similarity	NPD9493	Approved
0.6842	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD37	Approved
0.6835	Remote Similarity	NPD1470	Approved
0.6826	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4380	Phase 2
0.6815	Remote Similarity	NPD4966	Approved
0.6815	Remote Similarity	NPD5691	Approved
0.6815	Remote Similarity	NPD4965	Approved
0.6815	Remote Similarity	NPD4967	Phase 2
0.6815	Remote Similarity	NPD1357	Approved
0.6812	Remote Similarity	NPD2982	Phase 2
0.6812	Remote Similarity	NPD4359	Approved
0.6812	Remote Similarity	NPD2983	Phase 2
0.681	Remote Similarity	NPD7054	Approved
0.6809	Remote Similarity	NPD2614	Approved
0.6806	Remote Similarity	NPD1933	Approved
0.6803	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7440	Discontinued
0.6794	Remote Similarity	NPD9377	Approved
0.6794	Remote Similarity	NPD9379	Approved
0.6786	Remote Similarity	NPD2798	Approved
0.6783	Remote Similarity	NPD6663	Approved
0.6781	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6386	Approved
0.6774	Remote Similarity	NPD6385	Approved
0.6768	Remote Similarity	NPD7472	Approved
0.6767	Remote Similarity	NPD6671	Approved
0.6765	Remote Similarity	NPD1778	Approved
0.6765	Remote Similarity	NPD3019	Approved
0.6765	Remote Similarity	NPD2932	Approved
0.6763	Remote Similarity	NPD5310	Approved
0.6763	Remote Similarity	NPD5311	Approved
0.6761	Remote Similarity	NPD9537	Phase 1
0.6761	Remote Similarity	NPD9536	Phase 1
0.6759	Remote Similarity	NPD6653	Approved
0.675	Remote Similarity	NPD8127	Discontinued
0.6748	Remote Similarity	NPD7228	Approved
0.6739	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2981	Phase 2
0.6739	Remote Similarity	NPD9717	Approved
0.6738	Remote Similarity	NPD2861	Phase 2
0.6736	Remote Similarity	NPD2979	Phase 3
0.6736	Remote Similarity	NPD3620	Phase 2
0.6736	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1558	Phase 1
0.6735	Remote Similarity	NPD5405	Approved
0.6735	Remote Similarity	NPD5406	Approved
0.6735	Remote Similarity	NPD5408	Approved
0.6735	Remote Similarity	NPD5404	Approved
0.6728	Remote Similarity	NPD6166	Phase 2
0.6728	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6797	Phase 2
0.6716	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1164	Approved
0.6714	Remote Similarity	NPD3266	Approved
0.6714	Remote Similarity	NPD3053	Approved
0.6714	Remote Similarity	NPD3055	Approved
0.6714	Remote Similarity	NPD3267	Approved
0.6713	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.669	Remote Similarity	NPD274	Approved
0.669	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.669	Remote Similarity	NPD275	Approved
0.669	Remote Similarity	NPD6832	Phase 2
0.6689	Remote Similarity	NPD2344	Approved
0.6687	Remote Similarity	NPD7251	Discontinued
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6584	Phase 3
0.6667	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD7843	Approved
0.6667	Remote Similarity	NPD1510	Phase 2
0.6644	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD17	Approved
0.6642	Remote Similarity	NPD7157	Approved
0.6642	Remote Similarity	NPD4198	Discontinued
0.6623	Remote Similarity	NPD5403	Approved
0.6623	Remote Similarity	NPD2354	Approved
0.6622	Remote Similarity	NPD2438	Suspended
0.6622	Remote Similarity	NPD9570	Approved
0.6622	Remote Similarity	NPD1551	Phase 2
0.6621	Remote Similarity	NPD4140	Approved
0.6621	Remote Similarity	NPD3062	Approved
0.6621	Remote Similarity	NPD3059	Approved
0.6621	Remote Similarity	NPD3061	Approved
0.6621	Remote Similarity	NPD4307	Phase 2
0.662	Remote Similarity	NPD3018	Phase 2
0.6618	Remote Similarity	NPD1548	Phase 1
0.6617	Remote Similarity	NPD1241	Discontinued
0.6615	Remote Similarity	NPD9266	Approved
0.6615	Remote Similarity	NPD74	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