NPASS Compound

Structure

NPC476364 OpenBabel07101719152D 25 28 0 0 1 0 0 0 0 0999 V2000 4.1599 2.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6596 -0.4447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0474 -1.3006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2010 1.9603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8089 1.0795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8788 2.6055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7138 3.0876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7138 1.1593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6570 0.2244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0324 2.1234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9431 0.2005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8788 1.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8912 0.8780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5487 2.6055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5487 1.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0438 1.1593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1631 1.5515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5262 1.4686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4821 0.8350 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0453 2.2811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4409 0.9357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1482 -0.9527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4657 2.9034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4657 1.3434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 2 11 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 10 25 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 6 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 12 1 1 0 0 0 16 17 1 0 0 0 0 17 18 1 6 0 0 0 17 19 1 0 0 0 0 18 21 2 0 0 0 0 19 20 1 1 0 0 0 19 22 1 0 0 0 0 20 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.15
Volume:	348.383
LogP:	2.609
LogD:	2.371
LogS:	-3.841
# Rotatable Bonds:	4
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.852
Synthetic Accessibility Score:	5.084
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.531
MDCK Permeability:	1.4365728020493407e-05
Pgp-inhibitor:	0.924
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.2

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15
Plasma Protein Binding (PPB):	90.1448745727539%
Volume Distribution (VD):	1.129
Pgp-substrate:	4.686047077178955%

ADMET: Metabolism

CYP1A2-inhibitor:	0.706
CYP1A2-substrate:	0.786
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.679
CYP2C9-inhibitor:	0.28
CYP2C9-substrate:	0.344
CYP2D6-inhibitor:	0.951
CYP2D6-substrate:	0.629
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.459

ADMET: Excretion

Clearance (CL):	11.557
Half-life (T1/2):	0.293

ADMET: Toxicity

hERG Blockers:	0.331
Human Hepatotoxicity (H-HT):	0.596
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.485
Maximum Recommended Daily Dose:	0.832
Skin Sensitization:	0.379
Carcinogencity:	0.366
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC476364

Natural Product ID:	NPC476364
*Common Name:**	Ocophylol A
IUPAC Name:	(1S,5S,6R,7R,8R)-7-(1,3-benzodioxol-5-yl)-8-hydroxy-5-methoxy-6-methyl-3-prop-2-enylbicyclo[3.2.1]oct-3-en-2-one
Synonyms:
Standard InCHIKey:	ARFBOYDNJXQGTO-IXYCQQMVSA-N
Standard InCHI:	InChI=1S/C20H22O5/c1-4-5-13-9-20(23-3)11(2)16(17(18(13)21)19(20)22)12-6-7-14-15(8-12)25-10-24-14/h4,6-9,11,16-17,19,22H,1,5,10H2,2-3H3/t11-,16+,17-,19-,20-/m1/s1
SMILES:	C=CCC1=C[C@]2(OC)[C@@H]([C@@H](C1=O)[C@@H]([C@H]2C)c1ccc2c(c1)OCO2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL585724
PubChem CID:	45487110
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19548690]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO27964	Nectandra amazonum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27964	Nectandra amazonum	Species	Lauraceae	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	6
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	88600.0	nM	PMID[507672]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	312000.0	nM	PMID[507672]
NPT2	Others	Unspecified		IC50	=	256000.0	nM	PMID[507672]
NPT2	Others	Unspecified		Ratio IC50	=	0.284	n.a.	PMID[507672]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3080.0	nM	PMID[507672]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	45600.0	nM	PMID[507672]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	636000.0	nM	PMID[507672]

☑ 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 NPC476364 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	346
0.1-0.2	1360
0.2-0.3	2911
0.3-0.4	6979
0.4-0.5	11308
0.5-0.6	5786
0.6-0.7	10661
0.7-0.8	3227
0.8-0.85	97
0.85-0.9	14
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC476337
0.9521	High Similarity	NPC476359
0.9521	High Similarity	NPC476338
0.9359	High Similarity	NPC476277
0.9257	High Similarity	NPC476336
0.9205	High Similarity	NPC476335
0.8924	High Similarity	NPC476244
0.891	High Similarity	NPC476340
0.8824	High Similarity	NPC12854
0.88	High Similarity	NPC15743
0.8758	High Similarity	NPC472567
0.8734	High Similarity	NPC472565
0.8734	High Similarity	NPC475095
0.8733	High Similarity	NPC472564
0.8725	High Similarity	NPC51681
0.8662	High Similarity	NPC476363
0.8645	High Similarity	NPC163002
0.85	High Similarity	NPC76211
0.85	High Similarity	NPC179914
0.8497	Intermediate Similarity	NPC327052
0.8471	Intermediate Similarity	NPC28724
0.8457	Intermediate Similarity	NPC206815
0.8447	Intermediate Similarity	NPC474936
0.8442	Intermediate Similarity	NPC30890
0.8421	Intermediate Similarity	NPC96194
0.8421	Intermediate Similarity	NPC299855
0.8421	Intermediate Similarity	NPC104956
0.8408	Intermediate Similarity	NPC475379
0.84	Intermediate Similarity	NPC166184
0.8387	Intermediate Similarity	NPC153620
0.8387	Intermediate Similarity	NPC24257
0.8372	Intermediate Similarity	NPC189704
0.8344	Intermediate Similarity	NPC476011
0.8333	Intermediate Similarity	NPC239818
0.8333	Intermediate Similarity	NPC107739
0.8333	Intermediate Similarity	NPC218471
0.8324	Intermediate Similarity	NPC476067
0.8324	Intermediate Similarity	NPC475121
0.8323	Intermediate Similarity	NPC189054
0.8323	Intermediate Similarity	NPC476362
0.8323	Intermediate Similarity	NPC286919
0.8323	Intermediate Similarity	NPC475663
0.8313	Intermediate Similarity	NPC475484
0.8312	Intermediate Similarity	NPC46161
0.8312	Intermediate Similarity	NPC239608
0.8312	Intermediate Similarity	NPC46880
0.8303	Intermediate Similarity	NPC301910
0.8303	Intermediate Similarity	NPC130730
0.8302	Intermediate Similarity	NPC308555
0.8299	Intermediate Similarity	NPC477694
0.8299	Intermediate Similarity	NPC477705
0.8289	Intermediate Similarity	NPC470855
0.8284	Intermediate Similarity	NPC23593
0.8272	Intermediate Similarity	NPC469384
0.8255	Intermediate Similarity	NPC327410
0.8243	Intermediate Similarity	NPC477706
0.8242	Intermediate Similarity	NPC180586
0.8235	Intermediate Similarity	NPC28398
0.8219	Intermediate Similarity	NPC64948
0.8205	Intermediate Similarity	NPC472560
0.8204	Intermediate Similarity	NPC21956
0.8199	Intermediate Similarity	NPC254163
0.8193	Intermediate Similarity	NPC282551
0.8187	Intermediate Similarity	NPC236089
0.8187	Intermediate Similarity	NPC327225
0.8182	Intermediate Similarity	NPC475299
0.8176	Intermediate Similarity	NPC178048
0.8176	Intermediate Similarity	NPC62354
0.8176	Intermediate Similarity	NPC263955
0.8171	Intermediate Similarity	NPC230670
0.8171	Intermediate Similarity	NPC71385
0.817	Intermediate Similarity	NPC474784
0.817	Intermediate Similarity	NPC322021
0.8166	Intermediate Similarity	NPC195972
0.8158	Intermediate Similarity	NPC52968
0.8158	Intermediate Similarity	NPC231719
0.8153	Intermediate Similarity	NPC25496
0.8148	Intermediate Similarity	NPC475378
0.8137	Intermediate Similarity	NPC25127
0.8133	Intermediate Similarity	NPC475738
0.8129	Intermediate Similarity	NPC29587
0.8125	Intermediate Similarity	NPC56184
0.8125	Intermediate Similarity	NPC112708
0.8125	Intermediate Similarity	NPC151425
0.8121	Intermediate Similarity	NPC76687
0.8117	Intermediate Similarity	NPC323601
0.8113	Intermediate Similarity	NPC227980
0.8113	Intermediate Similarity	NPC147224
0.8101	Intermediate Similarity	NPC308178
0.8098	Intermediate Similarity	NPC220462
0.8089	Intermediate Similarity	NPC3982
0.8086	Intermediate Similarity	NPC186316
0.8079	Intermediate Similarity	NPC473711
0.8072	Intermediate Similarity	NPC100420
0.8072	Intermediate Similarity	NPC469475
0.8072	Intermediate Similarity	NPC469518
0.8072	Intermediate Similarity	NPC100425
0.8054	Intermediate Similarity	NPC233961
0.8054	Intermediate Similarity	NPC280399
0.8054	Intermediate Similarity	NPC339621
0.805	Intermediate Similarity	NPC96599
0.805	Intermediate Similarity	NPC161955
0.805	Intermediate Similarity	NPC474903
0.805	Intermediate Similarity	NPC477698
0.8049	Intermediate Similarity	NPC68619
0.8037	Intermediate Similarity	NPC261090
0.8037	Intermediate Similarity	NPC478248
0.8037	Intermediate Similarity	NPC478055
0.8026	Intermediate Similarity	NPC174191
0.8025	Intermediate Similarity	NPC287504
0.8025	Intermediate Similarity	NPC478232
0.8025	Intermediate Similarity	NPC223185
0.8025	Intermediate Similarity	NPC136757
0.8013	Intermediate Similarity	NPC86455
0.8013	Intermediate Similarity	NPC125134
0.8013	Intermediate Similarity	NPC137920
0.8012	Intermediate Similarity	NPC203664
0.8012	Intermediate Similarity	NPC475244
0.8	Intermediate Similarity	NPC240592
0.8	Intermediate Similarity	NPC470685
0.8	Intermediate Similarity	NPC166137
0.8	Intermediate Similarity	NPC138993
0.8	Intermediate Similarity	NPC158635
0.8	Intermediate Similarity	NPC205054
0.8	Intermediate Similarity	NPC472961
0.8	Intermediate Similarity	NPC229882
0.8	Intermediate Similarity	NPC117346
0.8	Intermediate Similarity	NPC282291
0.8	Intermediate Similarity	NPC475170
0.8	Intermediate Similarity	NPC472962
0.7989	Intermediate Similarity	NPC186746
0.7988	Intermediate Similarity	NPC226759
0.7988	Intermediate Similarity	NPC474990
0.7987	Intermediate Similarity	NPC325625
0.7987	Intermediate Similarity	NPC98009
0.7964	Intermediate Similarity	NPC109990
0.7964	Intermediate Similarity	NPC475865
0.7963	Intermediate Similarity	NPC137813
0.7963	Intermediate Similarity	NPC44730
0.7963	Intermediate Similarity	NPC89693
0.7963	Intermediate Similarity	NPC229548
0.7963	Intermediate Similarity	NPC478241
0.7961	Intermediate Similarity	NPC37065
0.7953	Intermediate Similarity	NPC473467
0.7953	Intermediate Similarity	NPC105137
0.7953	Intermediate Similarity	NPC475197
0.7952	Intermediate Similarity	NPC99968
0.795	Intermediate Similarity	NPC289021
0.795	Intermediate Similarity	NPC269914
0.795	Intermediate Similarity	NPC477700
0.795	Intermediate Similarity	NPC478249
0.795	Intermediate Similarity	NPC32079
0.795	Intermediate Similarity	NPC234152
0.795	Intermediate Similarity	NPC164082
0.795	Intermediate Similarity	NPC158546
0.7949	Intermediate Similarity	NPC52664
0.7947	Intermediate Similarity	NPC259742
0.7947	Intermediate Similarity	NPC219671
0.7947	Intermediate Similarity	NPC104077
0.7947	Intermediate Similarity	NPC147616
0.7945	Intermediate Similarity	NPC244876
0.7941	Intermediate Similarity	NPC212748
0.7937	Intermediate Similarity	NPC145569
0.7937	Intermediate Similarity	NPC478242
0.7937	Intermediate Similarity	NPC216223
0.7935	Intermediate Similarity	NPC278076
0.7933	Intermediate Similarity	NPC142985
0.7933	Intermediate Similarity	NPC195292
0.7927	Intermediate Similarity	NPC478223
0.7922	Intermediate Similarity	NPC14022
0.7917	Intermediate Similarity	NPC474301
0.7911	Intermediate Similarity	NPC213900
0.7911	Intermediate Similarity	NPC210330
0.7908	Intermediate Similarity	NPC470990
0.7907	Intermediate Similarity	NPC469438
0.7904	Intermediate Similarity	NPC125991
0.7904	Intermediate Similarity	NPC469512
0.7904	Intermediate Similarity	NPC145847
0.7901	Intermediate Similarity	NPC289438
0.7901	Intermediate Similarity	NPC477699
0.7898	Intermediate Similarity	NPC186296
0.7895	Intermediate Similarity	NPC469506
0.7895	Intermediate Similarity	NPC205915
0.7888	Intermediate Similarity	NPC177830
0.7886	Intermediate Similarity	NPC473883
0.7885	Intermediate Similarity	NPC137501
0.7885	Intermediate Similarity	NPC159387
0.7885	Intermediate Similarity	NPC100675
0.7885	Intermediate Similarity	NPC7518
0.7885	Intermediate Similarity	NPC154262
0.7885	Intermediate Similarity	NPC476334
0.7881	Intermediate Similarity	NPC469480
0.7879	Intermediate Similarity	NPC223335
0.7879	Intermediate Similarity	NPC40920
0.7877	Intermediate Similarity	NPC256167
0.7875	Intermediate Similarity	NPC473428
0.7874	Intermediate Similarity	NPC108191
0.7874	Intermediate Similarity	NPC93685
0.7871	Intermediate Similarity	NPC318575
0.7866	Intermediate Similarity	NPC10205

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 NPC476364 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	835
0.2-0.3	1769
0.3-0.4	2693
0.4-0.5	2047
0.5-0.6	1050
0.6-0.7	405
0.7-0.8	49
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
0.8408	Intermediate Similarity	NPD7028	Phase 2
0.8059	Intermediate Similarity	NPD7685	Pre-registration
0.8025	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7199	Phase 2
0.7874	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3818	Discontinued
0.7751	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD37	Approved
0.7711	Intermediate Similarity	NPD4966	Approved
0.7711	Intermediate Similarity	NPD4967	Phase 2
0.7711	Intermediate Similarity	NPD4965	Approved
0.7654	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD3882	Suspended
0.7471	Intermediate Similarity	NPD5494	Approved
0.7434	Intermediate Similarity	NPD5647	Approved
0.7429	Intermediate Similarity	NPD7074	Phase 3
0.7427	Intermediate Similarity	NPD8127	Discontinued
0.7414	Intermediate Similarity	NPD7228	Approved
0.7391	Intermediate Similarity	NPD4628	Phase 3
0.7371	Intermediate Similarity	NPD7054	Approved
0.7333	Intermediate Similarity	NPD3705	Approved
0.733	Intermediate Similarity	NPD7472	Approved
0.7321	Intermediate Similarity	NPD1934	Approved
0.7284	Intermediate Similarity	NPD4110	Phase 3
0.7284	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9494	Approved
0.7261	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3620	Phase 2
0.7253	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1357	Approved
0.7247	Intermediate Similarity	NPD7240	Approved
0.7237	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3751	Discontinued
0.7216	Intermediate Similarity	NPD7799	Discontinued
0.7207	Intermediate Similarity	NPD7808	Phase 3
0.7207	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5762	Approved
0.7205	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6005	Phase 3
0.7205	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6002	Phase 3
0.7205	Intermediate Similarity	NPD6004	Phase 3
0.7205	Intermediate Similarity	NPD5763	Approved
0.7191	Intermediate Similarity	NPD6797	Phase 2
0.7176	Intermediate Similarity	NPD5761	Phase 2
0.7176	Intermediate Similarity	NPD5760	Phase 2
0.7176	Intermediate Similarity	NPD2801	Approved
0.7169	Intermediate Similarity	NPD6273	Approved
0.7159	Intermediate Similarity	NPD7473	Discontinued
0.7151	Intermediate Similarity	NPD7251	Discontinued
0.7151	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD3817	Phase 2
0.7134	Intermediate Similarity	NPD6190	Approved
0.7114	Intermediate Similarity	NPD5536	Phase 2
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7107	Intermediate Similarity	NPD5735	Approved
0.7102	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6166	Phase 2
0.7101	Intermediate Similarity	NPD4380	Phase 2
0.7086	Intermediate Similarity	NPD3787	Discontinued
0.7086	Intermediate Similarity	NPD6232	Discontinued
0.7076	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3027	Phase 3
0.7063	Intermediate Similarity	NPD6653	Approved
0.7056	Intermediate Similarity	NPD6765	Approved
0.7056	Intermediate Similarity	NPD6764	Approved
0.7049	Intermediate Similarity	NPD8434	Phase 2
0.7011	Intermediate Similarity	NPD919	Approved
0.6994	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7266	Discontinued
0.6989	Remote Similarity	NPD7296	Approved
0.6989	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2798	Approved
0.6983	Remote Similarity	NPD5844	Phase 1
0.6983	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7819	Suspended
0.6975	Remote Similarity	NPD7033	Discontinued
0.6975	Remote Similarity	NPD2799	Discontinued
0.697	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8166	Discontinued
0.6968	Remote Similarity	NPD1876	Approved
0.6959	Remote Similarity	NPD5283	Phase 1
0.6954	Remote Similarity	NPD7075	Discontinued
0.6949	Remote Similarity	NPD3926	Phase 2
0.6948	Remote Similarity	NPD1608	Approved
0.6946	Remote Similarity	NPD6799	Approved
0.694	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4140	Approved
0.6936	Remote Similarity	NPD5978	Approved
0.6936	Remote Similarity	NPD5977	Approved
0.6932	Remote Similarity	NPD1247	Approved
0.6919	Remote Similarity	NPD6801	Discontinued
0.6909	Remote Similarity	NPD6674	Discontinued
0.6909	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2532	Approved
0.6905	Remote Similarity	NPD2533	Approved
0.6905	Remote Similarity	NPD2534	Approved
0.6902	Remote Similarity	NPD6785	Approved
0.6902	Remote Similarity	NPD6784	Approved
0.6901	Remote Similarity	NPD6599	Discontinued
0.6894	Remote Similarity	NPD230	Phase 1
0.6885	Remote Similarity	NPD8312	Approved
0.6885	Remote Similarity	NPD8313	Approved
0.6882	Remote Similarity	NPD1653	Approved
0.6871	Remote Similarity	NPD1510	Phase 2
0.686	Remote Similarity	NPD6385	Approved
0.686	Remote Similarity	NPD6386	Approved
0.6848	Remote Similarity	NPD2424	Discontinued
0.6848	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1511	Approved
0.6832	Remote Similarity	NPD1240	Approved
0.6829	Remote Similarity	NPD5712	Approved
0.6829	Remote Similarity	NPD2796	Approved
0.6829	Remote Similarity	NPD2935	Discontinued
0.6805	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.679	Remote Similarity	NPD447	Suspended
0.679	Remote Similarity	NPD3657	Discovery
0.6788	Remote Similarity	NPD2344	Approved
0.6782	Remote Similarity	NPD8455	Phase 2
0.6772	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4624	Approved
0.677	Remote Similarity	NPD6663	Approved
0.6766	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1512	Approved
0.6753	Remote Similarity	NPD17	Approved
0.6752	Remote Similarity	NPD1283	Approved
0.6748	Remote Similarity	NPD1607	Approved
0.6748	Remote Similarity	NPD6353	Approved
0.6747	Remote Similarity	NPD1549	Phase 2
0.6743	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5353	Approved
0.6736	Remote Similarity	NPD6777	Approved
0.6736	Remote Similarity	NPD6776	Approved
0.6736	Remote Similarity	NPD6778	Approved
0.6736	Remote Similarity	NPD6779	Approved
0.6736	Remote Similarity	NPD6780	Approved
0.6736	Remote Similarity	NPD6782	Approved
0.6736	Remote Similarity	NPD6781	Approved
0.6733	Remote Similarity	NPD1241	Discontinued
0.6731	Remote Similarity	NPD3972	Approved
0.6728	Remote Similarity	NPD943	Approved
0.6721	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7497	Discontinued
0.6711	Remote Similarity	NPD228	Approved
0.6708	Remote Similarity	NPD6798	Discontinued
0.6708	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3764	Approved
0.6707	Remote Similarity	NPD2800	Approved
0.6707	Remote Similarity	NPD7097	Phase 1
0.6706	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7315	Approved
0.6688	Remote Similarity	NPD1651	Approved
0.6687	Remote Similarity	NPD1933	Approved
0.6687	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1375	Discontinued
0.6686	Remote Similarity	NPD5058	Phase 3
0.6686	Remote Similarity	NPD7236	Approved
0.6684	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD5242	Approved
0.6667	Remote Similarity	NPD3092	Approved
0.6648	Remote Similarity	NPD5402	Approved
0.6648	Remote Similarity	NPD2163	Approved
0.6647	Remote Similarity	NPD4357	Discontinued
0.6647	Remote Similarity	NPD5958	Discontinued
0.6647	Remote Similarity	NPD3226	Approved
0.6646	Remote Similarity	NPD7095	Approved
0.6645	Remote Similarity	NPD2932	Approved
0.6634	Remote Similarity	NPD7930	Approved
0.6633	Remote Similarity	NPD7435	Discontinued
0.6633	Remote Similarity	NPD7680	Approved
0.6629	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD920	Approved
0.6627	Remote Similarity	NPD2438	Suspended
0.6627	Remote Similarity	NPD2309	Approved
0.6626	Remote Similarity	NPD4060	Phase 1
0.6625	Remote Similarity	NPD5736	Approved
0.6625	Remote Similarity	NPD2861	Phase 2
0.6623	Remote Similarity	NPD9545	Approved
0.6608	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3146	Approved
0.6608	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4236	Phase 3
0.6607	Remote Similarity	NPD4237	Approved
0.6604	Remote Similarity	NPD6362	Approved
0.6604	Remote Similarity	NPD3094	Phase 2
0.6596	Remote Similarity	NPD8150	Discontinued
0.6591	Remote Similarity	NPD2977	Approved
0.6591	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1465	Phase 2
0.6591	Remote Similarity	NPD2978	Approved
0.659	Remote Similarity	NPD4210	Discontinued

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