NPASS Compound

Structure

NPC473365 OpenBabel07101718332D 37 42 0 0 1 0 0 0 0 0999 V2000 4.4464 -0.6573 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 5.4052 -0.9414 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 3.9545 -2.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2859 -1.6498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9451 -1.2527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7210 -1.3457 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 4.6722 1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5333 -1.7289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7622 -1.0617 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6387 -1.9137 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 4.9133 -2.6021 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 3.0898 2.2226 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 2.6831 -0.3090 0.0000 C 0 0 2 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 1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6667 1.6226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2493 -2.6878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5975 -2.1977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1467 -3.5744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5021 3.0316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 3 2 0 0 0 0 1 11 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 11 2 0 0 0 0 5 19 1 0 0 0 0 6 12 2 0 0 0 0 6 20 1 0 0 0 0 7 14 1 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 21 2 0 0 0 0 10 14 1 0 0 0 0 10 22 2 0 0 0 0 13 29 1 0 0 0 0 14 30 2 0 0 0 0 15 11 1 6 0 0 0 15 23 1 0 0 0 0 16 24 2 0 0 0 0 17 19 2 0 0 0 0 17 31 1 0 0 0 0 18 20 2 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 21 24 1 0 0 0 0 21 35 1 0 0 0 0 22 25 1 0 0 0 0 22 37 1 0 0 0 0 23 16 1 1 0 0 0 23 25 1 0 0 0 0 25 26 1 0 0 0 0 26 24 1 6 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 27 36 1 1 0 0 0 28 12 1 6 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.14
Volume:	491.616
LogP:	2.829
LogD:	1.843
LogS:	-4.302
# Rotatable Bonds:	2
TPSA:	167.91
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	4.709
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.226
MDCK Permeability:	5.359656370274024e-06
Pgp-inhibitor:	0.027
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.547
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	91.29821014404297%
Volume Distribution (VD):	0.494
Pgp-substrate:	6.491866588592529%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.678
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.543
CYP3A4-substrate:	0.345

ADMET: Excretion

Clearance (CL):	17.3
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.558
AMES Toxicity:	0.47
Rat Oral Acute Toxicity:	0.441
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.957
Carcinogencity:	0.267
Eye Corrosion:	0.003
Eye Irritation:	0.904
Respiratory Toxicity:	0.122

Download Data

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

Natural Product: NPC473365

Natural Product ID:	NPC473365
*Common Name:**	Jezonocinol C
IUPAC Name:	n.a.
Synonyms:	Jezonocinol C
Standard InCHIKey:	LCRLZIMLAUAPJF-IWSVXSTESA-N
Standard InCHI:	InChI=1S/C28H24O9/c29-13-8-16-23-15(11-1-3-17(31)19(33)5-11)7-14(30)10-22-25(23)26(24(16)21(35)9-13)27(36)28(37-22)12-2-4-18(32)20(34)6-12/h1-6,8-10,15,23,25-29,31-36H,7H2/t15-,23+,25?,26+,27-,28+/m0/s1
SMILES:	Oc1cc(O)c2c(c1)[C@@H]1C3[C@@H]2[C@H](O)[C@H](OC3=CC(=O)C[C@H]1c1ccc(c(c1)O)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403353
PubChem CID:	23634535
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17907781]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[19646881]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		SC50	=	3.83	uM	PMID[470454]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	2.3	n.a.	PMID[470455]

☑ 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 NPC473365 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	405
0.1-0.2	1388
0.2-0.3	2902
0.3-0.4	7317
0.4-0.5	11334
0.5-0.6	4667
0.6-0.7	6602
0.7-0.8	7799
0.8-0.85	282
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8544	High Similarity	NPC203757
0.8523	High Similarity	NPC476393
0.8491	Intermediate Similarity	NPC165483
0.8477	Intermediate Similarity	NPC178054
0.8471	Intermediate Similarity	NPC476434
0.8418	Intermediate Similarity	NPC474656
0.8418	Intermediate Similarity	NPC65591
0.8418	Intermediate Similarity	NPC178574
0.8395	Intermediate Similarity	NPC158188
0.8395	Intermediate Similarity	NPC177100
0.8395	Intermediate Similarity	NPC142252
0.8395	Intermediate Similarity	NPC139540
0.8387	Intermediate Similarity	NPC30720
0.8385	Intermediate Similarity	NPC166456
0.8385	Intermediate Similarity	NPC7543
0.8385	Intermediate Similarity	NPC98083
0.8385	Intermediate Similarity	NPC94220
0.8385	Intermediate Similarity	NPC24339
0.8373	Intermediate Similarity	NPC279209
0.8373	Intermediate Similarity	NPC102277
0.8354	Intermediate Similarity	NPC227485
0.8344	Intermediate Similarity	NPC42797
0.8344	Intermediate Similarity	NPC14030
0.8344	Intermediate Similarity	NPC473445
0.8344	Intermediate Similarity	NPC291957
0.8333	Intermediate Similarity	NPC171706
0.8333	Intermediate Similarity	NPC329836
0.8333	Intermediate Similarity	NPC301089
0.8333	Intermediate Similarity	NPC24164
0.8333	Intermediate Similarity	NPC24627
0.8323	Intermediate Similarity	NPC268515
0.8323	Intermediate Similarity	NPC156818
0.8323	Intermediate Similarity	NPC289322
0.8323	Intermediate Similarity	NPC38779
0.8323	Intermediate Similarity	NPC40222
0.8323	Intermediate Similarity	NPC68324
0.8323	Intermediate Similarity	NPC160512
0.8323	Intermediate Similarity	NPC114179
0.8313	Intermediate Similarity	NPC188079
0.8313	Intermediate Similarity	NPC67396
0.8312	Intermediate Similarity	NPC15659
0.8312	Intermediate Similarity	NPC304894
0.8301	Intermediate Similarity	NPC277784
0.8294	Intermediate Similarity	NPC198902
0.8293	Intermediate Similarity	NPC470898
0.8293	Intermediate Similarity	NPC291977
0.8288	Intermediate Similarity	NPC148366
0.8288	Intermediate Similarity	NPC311293
0.8282	Intermediate Similarity	NPC109061
0.8282	Intermediate Similarity	NPC84324
0.8282	Intermediate Similarity	NPC124747
0.8282	Intermediate Similarity	NPC165970
0.8282	Intermediate Similarity	NPC66618
0.8282	Intermediate Similarity	NPC155754
0.8282	Intermediate Similarity	NPC288131
0.8282	Intermediate Similarity	NPC113163
0.8282	Intermediate Similarity	NPC305987
0.8278	Intermediate Similarity	NPC94994
0.8272	Intermediate Similarity	NPC53545
0.8272	Intermediate Similarity	NPC284127
0.8272	Intermediate Similarity	NPC117418
0.8272	Intermediate Similarity	NPC476410
0.8272	Intermediate Similarity	NPC172202
0.8261	Intermediate Similarity	NPC291948
0.8261	Intermediate Similarity	NPC300845
0.8261	Intermediate Similarity	NPC104983
0.8261	Intermediate Similarity	NPC250436
0.8261	Intermediate Similarity	NPC469474
0.8261	Intermediate Similarity	NPC88803
0.8261	Intermediate Similarity	NPC24640
0.8253	Intermediate Similarity	NPC311912
0.825	Intermediate Similarity	NPC303950
0.825	Intermediate Similarity	NPC125487
0.825	Intermediate Similarity	NPC281703
0.8247	Intermediate Similarity	NPC135767
0.8247	Intermediate Similarity	NPC173203
0.8247	Intermediate Similarity	NPC274721
0.8247	Intermediate Similarity	NPC163508
0.8247	Intermediate Similarity	NPC155392
0.8242	Intermediate Similarity	NPC125039
0.8242	Intermediate Similarity	NPC58223
0.8242	Intermediate Similarity	NPC7154
0.8242	Intermediate Similarity	NPC7688
0.8242	Intermediate Similarity	NPC72787
0.8242	Intermediate Similarity	NPC36916
0.8242	Intermediate Similarity	NPC471788
0.8242	Intermediate Similarity	NPC36
0.8239	Intermediate Similarity	NPC270268
0.8235	Intermediate Similarity	NPC475783
0.8235	Intermediate Similarity	NPC38473
0.8235	Intermediate Similarity	NPC9218
0.8232	Intermediate Similarity	NPC219927
0.8232	Intermediate Similarity	NPC477841
0.8232	Intermediate Similarity	NPC476247
0.8232	Intermediate Similarity	NPC472964
0.8221	Intermediate Similarity	NPC472902
0.8221	Intermediate Similarity	NPC101731
0.8221	Intermediate Similarity	NPC53889
0.8221	Intermediate Similarity	NPC321399
0.8221	Intermediate Similarity	NPC36217
0.8217	Intermediate Similarity	NPC81835
0.8217	Intermediate Similarity	NPC20757
0.8217	Intermediate Similarity	NPC227516
0.8217	Intermediate Similarity	NPC476463
0.8217	Intermediate Similarity	NPC142528
0.8214	Intermediate Similarity	NPC257667
0.8214	Intermediate Similarity	NPC186847
0.8214	Intermediate Similarity	NPC469506
0.8214	Intermediate Similarity	NPC4200
0.8214	Intermediate Similarity	NPC472454
0.821	Intermediate Similarity	NPC183851
0.821	Intermediate Similarity	NPC63454
0.8205	Intermediate Similarity	NPC211758
0.8205	Intermediate Similarity	NPC474799
0.8205	Intermediate Similarity	NPC87794
0.8204	Intermediate Similarity	NPC300307
0.8204	Intermediate Similarity	NPC88557
0.8194	Intermediate Similarity	NPC277951
0.8194	Intermediate Similarity	NPC317237
0.8194	Intermediate Similarity	NPC44530
0.8194	Intermediate Similarity	NPC16353
0.8193	Intermediate Similarity	NPC175793
0.8193	Intermediate Similarity	NPC224851
0.8193	Intermediate Similarity	NPC43065
0.8193	Intermediate Similarity	NPC171985
0.8193	Intermediate Similarity	NPC320741
0.8187	Intermediate Similarity	NPC470769
0.8187	Intermediate Similarity	NPC478220
0.8187	Intermediate Similarity	NPC475141
0.8182	Intermediate Similarity	NPC116759
0.8182	Intermediate Similarity	NPC14294
0.8182	Intermediate Similarity	NPC476295
0.8182	Intermediate Similarity	NPC186686
0.8182	Intermediate Similarity	NPC121290
0.8182	Intermediate Similarity	NPC214279
0.8171	Intermediate Similarity	NPC289771
0.8171	Intermediate Similarity	NPC26326
0.817	Intermediate Similarity	NPC86744
0.8165	Intermediate Similarity	NPC106524
0.8165	Intermediate Similarity	NPC290695
0.816	Intermediate Similarity	NPC210459
0.816	Intermediate Similarity	NPC87317
0.816	Intermediate Similarity	NPC329091
0.8153	Intermediate Similarity	NPC236202
0.8153	Intermediate Similarity	NPC204770
0.8153	Intermediate Similarity	NPC108811
0.8153	Intermediate Similarity	NPC202742
0.8153	Intermediate Similarity	NPC263940
0.8153	Intermediate Similarity	NPC262911
0.8153	Intermediate Similarity	NPC294558
0.8153	Intermediate Similarity	NPC472333
0.8153	Intermediate Similarity	NPC208507
0.8153	Intermediate Similarity	NPC82917
0.8153	Intermediate Similarity	NPC18185
0.8153	Intermediate Similarity	NPC170103
0.8153	Intermediate Similarity	NPC268366
0.8153	Intermediate Similarity	NPC70409
0.8153	Intermediate Similarity	NPC58190
0.8148	Intermediate Similarity	NPC227062
0.8148	Intermediate Similarity	NPC318432
0.8144	Intermediate Similarity	NPC470271
0.8144	Intermediate Similarity	NPC311389
0.8144	Intermediate Similarity	NPC217781
0.8144	Intermediate Similarity	NPC260266
0.8144	Intermediate Similarity	NPC243877
0.8144	Intermediate Similarity	NPC14662
0.8144	Intermediate Similarity	NPC474024
0.8137	Intermediate Similarity	NPC18727
0.8137	Intermediate Similarity	NPC473736
0.8137	Intermediate Similarity	NPC25127
0.8137	Intermediate Similarity	NPC287504
0.8133	Intermediate Similarity	NPC293319
0.8133	Intermediate Similarity	NPC162169
0.8133	Intermediate Similarity	NPC166851
0.8133	Intermediate Similarity	NPC477840
0.8129	Intermediate Similarity	NPC469630
0.8121	Intermediate Similarity	NPC149389
0.8121	Intermediate Similarity	NPC237424
0.8121	Intermediate Similarity	NPC211107
0.8121	Intermediate Similarity	NPC472635
0.8121	Intermediate Similarity	NPC201800
0.8121	Intermediate Similarity	NPC238168
0.8121	Intermediate Similarity	NPC249070
0.8117	Intermediate Similarity	NPC19158
0.811	Intermediate Similarity	NPC470183
0.811	Intermediate Similarity	NPC268718
0.811	Intermediate Similarity	NPC150943
0.811	Intermediate Similarity	NPC474960
0.811	Intermediate Similarity	NPC91634
0.8105	Intermediate Similarity	NPC230124
0.8105	Intermediate Similarity	NPC114171
0.8105	Intermediate Similarity	NPC6300
0.8105	Intermediate Similarity	NPC184613
0.8101	Intermediate Similarity	NPC304821
0.8101	Intermediate Similarity	NPC252402
0.8101	Intermediate Similarity	NPC162751
0.8101	Intermediate Similarity	NPC102934
0.8101	Intermediate Similarity	NPC52161
0.8098	Intermediate Similarity	NPC470827
0.8098	Intermediate Similarity	NPC474010

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 NPC473365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	822
0.2-0.3	1594
0.3-0.4	2757
0.4-0.5	2046
0.5-0.6	1028
0.6-0.7	464
0.7-0.8	94
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6166	Phase 2
0.8171	Intermediate Similarity	NPD7199	Phase 2
0.8107	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1934	Approved
0.8049	Intermediate Similarity	NPD6234	Discontinued
0.8036	Intermediate Similarity	NPD7228	Approved
0.8025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD37	Approved
0.795	Intermediate Similarity	NPD4380	Phase 2
0.7947	Intermediate Similarity	NPD1613	Approved
0.7947	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4966	Approved
0.7927	Intermediate Similarity	NPD4965	Approved
0.7927	Intermediate Similarity	NPD4967	Phase 2
0.7882	Intermediate Similarity	NPD5844	Phase 1
0.7874	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7074	Phase 3
0.7824	Intermediate Similarity	NPD3818	Discontinued
0.7785	Intermediate Similarity	NPD6190	Approved
0.7778	Intermediate Similarity	NPD7054	Approved
0.7765	Intermediate Similarity	NPD7473	Discontinued
0.7748	Intermediate Similarity	NPD3027	Phase 3
0.7733	Intermediate Similarity	NPD7472	Approved
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7697	Intermediate Similarity	NPD2801	Approved
0.7692	Intermediate Similarity	NPD6232	Discontinued
0.7688	Intermediate Similarity	NPD6797	Phase 2
0.7688	Intermediate Similarity	NPD1511	Approved
0.7682	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7251	Discontinued
0.7633	Intermediate Similarity	NPD6959	Discontinued
0.7616	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD3882	Suspended
0.76	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1512	Approved
0.7574	Intermediate Similarity	NPD5494	Approved
0.7566	Intermediate Similarity	NPD4908	Phase 1
0.7543	Intermediate Similarity	NPD7240	Approved
0.7532	Intermediate Similarity	NPD7266	Discontinued
0.7531	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8127	Discontinued
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD7808	Phase 3
0.7468	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6559	Discontinued
0.7443	Intermediate Similarity	NPD7685	Pre-registration
0.744	Intermediate Similarity	NPD3817	Phase 2
0.7423	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7405	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1653	Approved
0.7391	Intermediate Similarity	NPD8166	Discontinued
0.7386	Intermediate Similarity	NPD2861	Phase 2
0.7384	Intermediate Similarity	NPD3787	Discontinued
0.7381	Intermediate Similarity	NPD7819	Suspended
0.7375	Intermediate Similarity	NPD1549	Phase 2
0.7372	Intermediate Similarity	NPD943	Approved
0.7353	Intermediate Similarity	NPD7075	Discontinued
0.7337	Intermediate Similarity	NPD5402	Approved
0.7333	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7296	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7262	Intermediate Similarity	NPD7411	Suspended
0.7261	Intermediate Similarity	NPD3620	Phase 2
0.7261	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7390	Discontinued
0.7253	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3749	Approved
0.725	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD6099	Approved
0.7249	Intermediate Similarity	NPD7680	Approved
0.7246	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3764	Approved
0.7229	Intermediate Similarity	NPD5403	Approved
0.7219	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3748	Approved
0.7176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8455	Phase 2
0.716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7124	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6801	Discontinued
0.7108	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5401	Approved
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7102	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7768	Phase 2
0.7086	Intermediate Similarity	NPD3019	Approved
0.7086	Intermediate Similarity	NPD7229	Phase 3
0.7081	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6273	Approved
0.7044	Intermediate Similarity	NPD1240	Approved
0.7037	Intermediate Similarity	NPD2796	Approved
0.7033	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3094	Phase 2
0.7025	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6798	Discontinued
0.7012	Intermediate Similarity	NPD6674	Discontinued
0.7006	Intermediate Similarity	NPD2532	Approved
0.7006	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD7028	Phase 2
0.6994	Remote Similarity	NPD5762	Approved
0.6994	Remote Similarity	NPD5763	Approved
0.6981	Remote Similarity	NPD6663	Approved
0.6975	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2932	Approved
0.697	Remote Similarity	NPD4628	Phase 3
0.697	Remote Similarity	NPD3892	Phase 2
0.6962	Remote Similarity	NPD4625	Phase 3
0.6957	Remote Similarity	NPD1607	Approved
0.6949	Remote Similarity	NPD3926	Phase 2
0.6946	Remote Similarity	NPD6799	Approved
0.6943	Remote Similarity	NPD5736	Approved
0.6937	Remote Similarity	NPD4060	Phase 1
0.6933	Remote Similarity	NPD5408	Approved
0.6933	Remote Similarity	NPD5405	Approved
0.6933	Remote Similarity	NPD5404	Approved
0.6933	Remote Similarity	NPD5406	Approved
0.6923	Remote Similarity	NPD7549	Discontinued
0.6909	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6599	Discontinued
0.6894	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5124	Phase 1
0.6888	Remote Similarity	NPD8151	Discontinued
0.6883	Remote Similarity	NPD1201	Approved
0.6883	Remote Similarity	NPD3092	Approved
0.6875	Remote Similarity	NPD6233	Phase 2
0.6867	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4110	Phase 3
0.686	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1876	Approved
0.6848	Remote Similarity	NPD2424	Discontinued
0.6842	Remote Similarity	NPD1548	Phase 1
0.6835	Remote Similarity	NPD3018	Phase 2
0.6829	Remote Similarity	NPD2935	Discontinued
0.6825	Remote Similarity	NPD6534	Approved
0.6825	Remote Similarity	NPD6535	Approved
0.6823	Remote Similarity	NPD6776	Approved
0.6823	Remote Similarity	NPD6782	Approved
0.6823	Remote Similarity	NPD6777	Approved
0.6823	Remote Similarity	NPD6781	Approved
0.6823	Remote Similarity	NPD6779	Approved
0.6823	Remote Similarity	NPD6780	Approved
0.6823	Remote Similarity	NPD6778	Approved
0.6815	Remote Similarity	NPD2797	Approved
0.6815	Remote Similarity	NPD1470	Approved
0.6813	Remote Similarity	NPD3268	Approved
0.6813	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1652	Phase 2
0.6804	Remote Similarity	NPD4002	Approved
0.6804	Remote Similarity	NPD4004	Approved
0.6803	Remote Similarity	NPD3021	Approved
0.6803	Remote Similarity	NPD3022	Approved
0.6795	Remote Similarity	NPD4749	Approved
0.679	Remote Similarity	NPD5735	Approved
0.6788	Remote Similarity	NPD2494	Approved
0.6788	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3452	Approved
0.6788	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6005	Phase 3
0.6788	Remote Similarity	NPD3450	Approved
0.6788	Remote Similarity	NPD2493	Approved
0.6788	Remote Similarity	NPD6002	Phase 3
0.6788	Remote Similarity	NPD6004	Phase 3
0.6769	Remote Similarity	NPD4583	Approved
0.6769	Remote Similarity	NPD4582	Approved
0.6768	Remote Similarity	NPD7033	Discontinued
0.6768	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7003	Approved
0.6766	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2490	Approved
0.6755	Remote Similarity	NPD2488	Approved
0.6753	Remote Similarity	NPD6823	Phase 2
0.6748	Remote Similarity	NPD6653	Approved
0.6746	Remote Similarity	NPD4357	Discontinued
0.6744	Remote Similarity	NPD3226	Approved
0.6738	Remote Similarity	NPD6841	Approved
0.6738	Remote Similarity	NPD6843	Phase 3
0.6738	Remote Similarity	NPD6842	Approved
0.6736	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3091	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