NPASS Compound

Structure

NPC308976 OpenBabel07101719522D 25 28 0 0 1 0 0 0 0 0999 V2000 0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 -0.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 1.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 2.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3917 1.0649 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8558 -0.9351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8558 1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 2.0594 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 8 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 24 1 0 0 0 0 10 7 1 6 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 18 1 6 0 0 0 16 8 1 1 0 0 0 16 25 1 0 0 0 0 17 9 1 1 0 0 0 17 24 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	328.735
LogP:	1.654
LogD:	1.508
LogS:	-3.425
# Rotatable Bonds:	2
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.487
Synthetic Accessibility Score:	3.883
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.095
MDCK Permeability:	5.6273784139193594e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	91.1416244506836%
Volume Distribution (VD):	0.531
Pgp-substrate:	17.29229164123535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.356
CYP2C9-substrate:	0.716
CYP2D6-inhibitor:	0.138
CYP2D6-substrate:	0.299
CYP3A4-inhibitor:	0.524
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	19.576
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.87
AMES Toxicity:	0.42
Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.949
Carcinogencity:	0.174
Eye Corrosion:	0.014
Eye Irritation:	0.932
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC308976

Natural Product ID:	NPC308976
*Common Name:**	(+)-3,4,3',4'-Tetrahydroxy-9,7'alpha-Epoxylignano-7 Alpha,9'-Lactone
IUPAC Name:	(3S,3aS,6S,6aR)-3,6-bis(3,4-dihydroxyphenyl)-3,3a,6,6a-tetrahydro-1H-furo[3,4-c]furan-4-one
Synonyms:
Standard InCHIKey:	DFZNKMAEHVZMHR-YQMWTZAJSA-N
Standard InCHI:	InChI=1S/C18H16O7/c19-11-3-1-8(5-13(11)21)16-10-7-24-17(15(10)18(23)25-16)9-2-4-12(20)14(22)6-9/h1-6,10,15-17,19-22H,7H2/t10-,15-,16+,17+/m0/s1
SMILES:	c1cc(c(cc1[C@@H]1[C@H]2CO[C@H](c3ccc(c(c3)O)O)[C@H]2C(=O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227135
PubChem CID:	16681478
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

*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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	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
IC50	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	5600.0	nM	PMID[505866]
NPT257	Individual Protein	Arachidonate 15-lipoxygenase	Oryctolagus cuniculus	IC50	=	520.0	nM	PMID[505866]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	90200.0	nM	PMID[505866]

☑ 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 NPC308976 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	315
0.1-0.2	1194
0.2-0.3	2928
0.3-0.4	6755
0.4-0.5	11869
0.5-0.6	5279
0.6-0.7	11167
0.7-0.8	3012
0.8-0.85	150
0.85-0.9	21
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9489	High Similarity	NPC223185
0.9098	High Similarity	NPC318799
0.9085	High Similarity	NPC125570
0.9058	High Similarity	NPC100675
0.9037	High Similarity	NPC106406
0.9	High Similarity	NPC131747
0.9	High Similarity	NPC257682
0.9	High Similarity	NPC146355
0.8966	High Similarity	NPC473236
0.8921	High Similarity	NPC9218
0.8865	High Similarity	NPC27159
0.8865	High Similarity	NPC183824
0.8857	High Similarity	NPC253722
0.8857	High Similarity	NPC31751
0.8857	High Similarity	NPC253481
0.8841	High Similarity	NPC281780
0.8806	High Similarity	NPC214246
0.8794	High Similarity	NPC273657
0.8794	High Similarity	NPC106920
0.8794	High Similarity	NPC285550
0.8784	High Similarity	NPC478055
0.8779	High Similarity	NPC473451
0.8776	High Similarity	NPC136757
0.8769	High Similarity	NPC472271
0.8769	High Similarity	NPC322332
0.8767	High Similarity	NPC477699
0.8759	High Similarity	NPC67247
0.8759	High Similarity	NPC176814
0.8759	High Similarity	NPC300776
0.8759	High Similarity	NPC4982
0.8759	High Similarity	NPC68779
0.8759	High Similarity	NPC5310
0.8741	High Similarity	NPC3982
0.8714	High Similarity	NPC156709
0.8714	High Similarity	NPC147379
0.8714	High Similarity	NPC179505
0.8696	High Similarity	NPC470990
0.869	High Similarity	NPC145569
0.869	High Similarity	NPC216223
0.8662	High Similarity	NPC477697
0.8662	High Similarity	NPC477696
0.8662	High Similarity	NPC470811
0.8652	High Similarity	NPC282291
0.8652	High Similarity	NPC166137
0.8639	High Similarity	NPC56184
0.8633	High Similarity	NPC471988
0.863	High Similarity	NPC32197
0.8601	High Similarity	NPC470130
0.8571	High Similarity	NPC67349
0.8571	High Similarity	NPC279676
0.8571	High Similarity	NPC85565
0.8562	High Similarity	NPC174512
0.8562	High Similarity	NPC477695
0.8562	High Similarity	NPC474965
0.8562	High Similarity	NPC668
0.8562	High Similarity	NPC293757
0.8561	High Similarity	NPC113295
0.8552	High Similarity	NPC229264
0.854	High Similarity	NPC228346
0.854	High Similarity	NPC158079
0.854	High Similarity	NPC115207
0.854	High Similarity	NPC7171
0.854	High Similarity	NPC161557
0.854	High Similarity	NPC27843
0.854	High Similarity	NPC198388
0.854	High Similarity	NPC40432
0.8514	High Similarity	NPC476434
0.85	High Similarity	NPC90431
0.8493	Intermediate Similarity	NPC1580
0.8478	Intermediate Similarity	NPC61
0.8478	Intermediate Similarity	NPC18074
0.8478	Intermediate Similarity	NPC5419
0.8478	Intermediate Similarity	NPC207400
0.8478	Intermediate Similarity	NPC181049
0.8478	Intermediate Similarity	NPC25581
0.8467	Intermediate Similarity	NPC186316
0.8462	Intermediate Similarity	NPC52664
0.8456	Intermediate Similarity	NPC299706
0.8456	Intermediate Similarity	NPC245615
0.8456	Intermediate Similarity	NPC61604
0.8456	Intermediate Similarity	NPC115466
0.8446	Intermediate Similarity	NPC477700
0.8435	Intermediate Similarity	NPC477698
0.8433	Intermediate Similarity	NPC288945
0.8425	Intermediate Similarity	NPC299090
0.8425	Intermediate Similarity	NPC283081
0.8425	Intermediate Similarity	NPC143892
0.8425	Intermediate Similarity	NPC221383
0.8421	Intermediate Similarity	NPC76211
0.8417	Intermediate Similarity	NPC168799
0.8417	Intermediate Similarity	NPC155209
0.8417	Intermediate Similarity	NPC471749
0.8409	Intermediate Similarity	NPC98305
0.8406	Intermediate Similarity	NPC469480
0.84	Intermediate Similarity	NPC477299
0.8392	Intermediate Similarity	NPC29599
0.8392	Intermediate Similarity	NPC470991
0.8389	Intermediate Similarity	NPC267091
0.8389	Intermediate Similarity	NPC270268
0.8385	Intermediate Similarity	NPC325295
0.8385	Intermediate Similarity	NPC76308
0.8369	Intermediate Similarity	NPC209229
0.8367	Intermediate Similarity	NPC192568
0.8367	Intermediate Similarity	NPC471076
0.8357	Intermediate Similarity	NPC248150
0.8357	Intermediate Similarity	NPC474895
0.8346	Intermediate Similarity	NPC147654
0.8345	Intermediate Similarity	NPC474692
0.8345	Intermediate Similarity	NPC4940
0.8344	Intermediate Similarity	NPC203757
0.8344	Intermediate Similarity	NPC38699
0.8333	Intermediate Similarity	NPC265454
0.8333	Intermediate Similarity	NPC131971
0.8333	Intermediate Similarity	NPC257582
0.8333	Intermediate Similarity	NPC34634
0.8333	Intermediate Similarity	NPC67467
0.8333	Intermediate Similarity	NPC178574
0.8333	Intermediate Similarity	NPC145305
0.8333	Intermediate Similarity	NPC174495
0.8333	Intermediate Similarity	NPC153739
0.8333	Intermediate Similarity	NPC241522
0.8333	Intermediate Similarity	NPC64201
0.8333	Intermediate Similarity	NPC65591
0.8333	Intermediate Similarity	NPC92164
0.8333	Intermediate Similarity	NPC187998
0.8333	Intermediate Similarity	NPC42300
0.8333	Intermediate Similarity	NPC77040
0.8333	Intermediate Similarity	NPC142985
0.8333	Intermediate Similarity	NPC242807
0.8322	Intermediate Similarity	NPC32079
0.8322	Intermediate Similarity	NPC164082
0.8322	Intermediate Similarity	NPC243891
0.8321	Intermediate Similarity	NPC45774
0.8321	Intermediate Similarity	NPC11258
0.8321	Intermediate Similarity	NPC128208
0.8321	Intermediate Similarity	NPC21867
0.8321	Intermediate Similarity	NPC282703
0.8321	Intermediate Similarity	NPC184733
0.8321	Intermediate Similarity	NPC86198
0.8321	Intermediate Similarity	NPC129570
0.831	Intermediate Similarity	NPC14022
0.831	Intermediate Similarity	NPC62907
0.8299	Intermediate Similarity	NPC191899
0.8299	Intermediate Similarity	NPC246229
0.8298	Intermediate Similarity	NPC103398
0.8298	Intermediate Similarity	NPC99572
0.8298	Intermediate Similarity	NPC126409
0.8298	Intermediate Similarity	NPC142547
0.8298	Intermediate Similarity	NPC180171
0.8298	Intermediate Similarity	NPC158325
0.8298	Intermediate Similarity	NPC135777
0.8298	Intermediate Similarity	NPC211386
0.8298	Intermediate Similarity	NPC123988
0.8289	Intermediate Similarity	NPC163635
0.8288	Intermediate Similarity	NPC53884
0.8288	Intermediate Similarity	NPC477702
0.8288	Intermediate Similarity	NPC258671
0.8278	Intermediate Similarity	NPC25127
0.8278	Intermediate Similarity	NPC30009
0.8278	Intermediate Similarity	NPC103197
0.8273	Intermediate Similarity	NPC277804
0.8267	Intermediate Similarity	NPC95498
0.8267	Intermediate Similarity	NPC246566
0.8261	Intermediate Similarity	NPC94810
0.8261	Intermediate Similarity	NPC475875
0.8261	Intermediate Similarity	NPC241354
0.8258	Intermediate Similarity	NPC144557
0.8258	Intermediate Similarity	NPC470214
0.8258	Intermediate Similarity	NPC109371
0.8258	Intermediate Similarity	NPC470215
0.8258	Intermediate Similarity	NPC70084
0.8255	Intermediate Similarity	NPC158635
0.8255	Intermediate Similarity	NPC229882
0.8252	Intermediate Similarity	NPC123526
0.8252	Intermediate Similarity	NPC220942
0.8252	Intermediate Similarity	NPC302857
0.8252	Intermediate Similarity	NPC193666
0.8252	Intermediate Similarity	NPC152942
0.8252	Intermediate Similarity	NPC37250
0.8252	Intermediate Similarity	NPC88640
0.8252	Intermediate Similarity	NPC219428
0.8252	Intermediate Similarity	NPC142703
0.8252	Intermediate Similarity	NPC278068
0.8248	Intermediate Similarity	NPC223807
0.8247	Intermediate Similarity	NPC239818
0.8247	Intermediate Similarity	NPC268718
0.8247	Intermediate Similarity	NPC218471
0.8247	Intermediate Similarity	NPC150943
0.8247	Intermediate Similarity	NPC91634
0.8244	Intermediate Similarity	NPC145023
0.8244	Intermediate Similarity	NPC200988
0.8244	Intermediate Similarity	NPC610
0.8244	Intermediate Similarity	NPC175799
0.8243	Intermediate Similarity	NPC476463
0.8243	Intermediate Similarity	NPC236166
0.8239	Intermediate Similarity	NPC470572
0.8231	Intermediate Similarity	NPC30890
0.8231	Intermediate Similarity	NPC212890
0.8224	Intermediate Similarity	NPC476642
0.8222	Intermediate Similarity	NPC212541

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 NPC308976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	735
0.2-0.3	1611
0.3-0.4	2670
0.4-0.5	2174
0.5-0.6	1186
0.6-0.7	455
0.7-0.8	54
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8301	Intermediate Similarity	NPD6234	Discontinued
0.8151	Intermediate Similarity	NPD6190	Approved
0.8052	Intermediate Similarity	NPD4967	Phase 2
0.8052	Intermediate Similarity	NPD4966	Approved
0.8052	Intermediate Similarity	NPD4965	Approved
0.7937	Intermediate Similarity	NPD7228	Approved
0.7902	Intermediate Similarity	NPD230	Phase 1
0.7857	Intermediate Similarity	NPD37	Approved
0.7817	Intermediate Similarity	NPD3764	Approved
0.78	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7266	Discontinued
0.7746	Intermediate Similarity	NPD3027	Phase 3
0.7718	Intermediate Similarity	NPD8166	Discontinued
0.7707	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6355	Discontinued
0.7634	Intermediate Similarity	NPD3022	Approved
0.7634	Intermediate Similarity	NPD3021	Approved
0.7628	Intermediate Similarity	NPD1934	Approved
0.7607	Intermediate Similarity	NPD3818	Discontinued
0.76	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4110	Phase 3
0.7595	Intermediate Similarity	NPD3882	Suspended
0.756	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6663	Approved
0.7516	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD1608	Approved
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD2801	Approved
0.7466	Intermediate Similarity	NPD1613	Approved
0.7466	Intermediate Similarity	NPD943	Approved
0.7466	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1511	Approved
0.745	Intermediate Similarity	NPD2935	Discontinued
0.745	Intermediate Similarity	NPD9570	Approved
0.7425	Intermediate Similarity	NPD7240	Approved
0.7423	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6005	Phase 3
0.74	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6004	Phase 3
0.74	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6002	Phase 3
0.7397	Intermediate Similarity	NPD6233	Phase 2
0.7396	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7033	Discontinued
0.7362	Intermediate Similarity	NPD6232	Discontinued
0.7361	Intermediate Similarity	NPD5736	Approved
0.7361	Intermediate Similarity	NPD2861	Phase 2
0.7355	Intermediate Similarity	NPD1512	Approved
0.7347	Intermediate Similarity	NPD826	Approved
0.7347	Intermediate Similarity	NPD825	Approved
0.7347	Intermediate Similarity	NPD4060	Phase 1
0.7333	Intermediate Similarity	NPD7473	Discontinued
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7329	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3455	Phase 2
0.7324	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7685	Pre-registration
0.7312	Intermediate Similarity	NPD3817	Phase 2
0.731	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5647	Approved
0.729	Intermediate Similarity	NPD2534	Approved
0.729	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2532	Approved
0.729	Intermediate Similarity	NPD2533	Approved
0.7286	Intermediate Similarity	NPD17	Approved
0.7285	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6166	Phase 2
0.7273	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD9545	Approved
0.7254	Intermediate Similarity	NPD9269	Phase 2
0.7248	Intermediate Similarity	NPD6653	Approved
0.7241	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5494	Approved
0.7237	Intermediate Similarity	NPD5958	Discontinued
0.7237	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2979	Phase 3
0.7219	Intermediate Similarity	NPD2438	Suspended
0.7202	Intermediate Similarity	NPD7074	Phase 3
0.7183	Intermediate Similarity	NPD1535	Discovery
0.7172	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4380	Phase 2
0.7162	Intermediate Similarity	NPD4062	Phase 3
0.716	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5283	Phase 1
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD3400	Discontinued
0.7133	Intermediate Similarity	NPD1481	Phase 2
0.7126	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7075	Discontinued
0.7103	Intermediate Similarity	NPD2797	Approved
0.7101	Intermediate Similarity	NPD7472	Approved
0.7099	Intermediate Similarity	NPD5402	Approved
0.7095	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5585	Approved
0.7091	Intermediate Similarity	NPD8127	Discontinued
0.7089	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD447	Suspended
0.7067	Intermediate Similarity	NPD555	Phase 2
0.7063	Intermediate Similarity	NPD3705	Approved
0.7063	Intermediate Similarity	NPD1281	Approved
0.7059	Intermediate Similarity	NPD6797	Phase 2
0.7059	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD257	Approved
0.7055	Intermediate Similarity	NPD258	Approved
0.7048	Intermediate Similarity	NPD7229	Phase 3
0.7042	Intermediate Similarity	NPD2932	Approved
0.7042	Intermediate Similarity	NPD3019	Approved
0.7041	Intermediate Similarity	NPD5844	Phase 1
0.7039	Intermediate Similarity	NPD1510	Phase 2
0.7039	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8455	Phase 2
0.7037	Intermediate Similarity	NPD7819	Suspended
0.7037	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7680	Approved
0.7032	Intermediate Similarity	NPD3750	Approved
0.7019	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6559	Discontinued
0.7018	Intermediate Similarity	NPD7251	Discontinued
0.7013	Intermediate Similarity	NPD4534	Discontinued
0.7013	Intermediate Similarity	NPD1549	Phase 2
0.7012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD228	Approved
0.7007	Intermediate Similarity	NPD9494	Approved
0.7006	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3620	Phase 2
0.6993	Remote Similarity	NPD1551	Phase 2
0.6993	Remote Similarity	NPD5404	Approved
0.6993	Remote Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD5408	Approved
0.6993	Remote Similarity	NPD5405	Approved
0.6993	Remote Similarity	NPD3847	Discontinued
0.6986	Remote Similarity	NPD3094	Phase 2
0.698	Remote Similarity	NPD3268	Approved
0.6978	Remote Similarity	NPD2629	Approved
0.6972	Remote Similarity	NPD9268	Approved
0.6968	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4908	Phase 1
0.6957	Remote Similarity	NPD6599	Discontinued
0.6951	Remote Similarity	NPD7768	Phase 2
0.6949	Remote Similarity	NPD7296	Approved
0.6948	Remote Similarity	NPD5762	Approved
0.6948	Remote Similarity	NPD5763	Approved
0.6947	Remote Similarity	NPD3020	Approved
0.6946	Remote Similarity	NPD3787	Discontinued
0.6946	Remote Similarity	NPD7315	Approved
0.6944	Remote Similarity	NPD1610	Phase 2
0.694	Remote Similarity	NPD5048	Discontinued
0.6937	Remote Similarity	NPD1653	Approved
0.6936	Remote Similarity	NPD8313	Approved
0.6936	Remote Similarity	NPD8312	Approved
0.6933	Remote Similarity	NPD259	Phase 1
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6273	Approved
0.6914	Remote Similarity	NPD8150	Discontinued
0.6914	Remote Similarity	NPD8434	Phase 2
0.6914	Remote Similarity	NPD6385	Approved
0.6914	Remote Similarity	NPD6386	Approved
0.6909	Remote Similarity	NPD3749	Approved
0.6894	Remote Similarity	NPD3226	Approved
0.6892	Remote Similarity	NPD9569	Approved
0.689	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4140	Approved
0.6887	Remote Similarity	NPD1240	Approved
0.6887	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2531	Phase 2
0.6883	Remote Similarity	NPD6032	Approved
0.6879	Remote Similarity	NPD9493	Approved
0.6879	Remote Similarity	NPD7808	Phase 3
0.6875	Remote Similarity	NPD5403	Approved
0.6871	Remote Similarity	NPD1164	Approved
0.6871	Remote Similarity	NPD6801	Discontinued
0.6871	Remote Similarity	NPD1470	Approved
0.6871	Remote Similarity	NPD1203	Approved
0.6867	Remote Similarity	NPD2313	Discontinued
0.6867	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7097	Phase 1
0.6853	Remote Similarity	NPD1651	Approved
0.6852	Remote Similarity	NPD7028	Phase 2
0.6849	Remote Similarity	NPD4359	Approved
0.6846	Remote Similarity	NPD2614	Approved
0.6839	Remote Similarity	NPD2346	Discontinued
0.6839	Remote Similarity	NPD2344	Approved
0.6839	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5536	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