NPASS Compound

Structure

CID48105 OpenBabel06191715382D 25 28 0 0 1 0 0 0 0 0999 V2000 -3.8983 2.3773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1462 1.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8404 2.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7125 1.9577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -1.0070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6794 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 0.9696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8399 -0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8395 2.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6853 -1.5334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1980 1.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8397 1.4549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3586 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6792 0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6794 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5191 1.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3588 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5195 -0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9700 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8402 1.4545 0.0000 C 0 0 0 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 -1.8035 2.5257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5190 2.4552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0794 -0.6478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7213 -1.4323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 22 2 0 0 0 0 10 24 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 12 9 1 6 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 18 2 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 1 0 0 0 21 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.2
Volume:	362.161
LogP:	4.913
LogD:	3.984
LogS:	-3.95
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.795
Synthetic Accessibility Score:	4.496
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.771
MDCK Permeability:	2.7220701667829417e-05
Pgp-inhibitor:	0.254
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.441
30% Bioavailability (F30%):	0.581

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.852
Plasma Protein Binding (PPB):	87.22809600830078%
Volume Distribution (VD):	5.73
Pgp-substrate:	2.27339243888855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.239
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.565
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.474
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.878
CYP2D6-substrate:	0.293
CYP3A4-inhibitor:	0.79
CYP3A4-substrate:	0.63

ADMET: Excretion

Clearance (CL):	11.156
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.059
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.314
Skin Sensitization:	0.89
Carcinogencity:	0.372
Eye Corrosion:	0.003
Eye Irritation:	0.853
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC48105

Natural Product ID:	NPC48105
*Common Name:**	Taiwaniaquinol A
IUPAC Name:	(6R,6aS,10aS)-5-hydroxy-7,7,10a-trimethyl-4-propan-2-yl-6a,8,9,10-tetrahydro-6H-indeno[2,1-g][1,3]benzodioxole-6-carbaldehyde
Synonyms:
Standard InCHIKey:	WZYATGGRHPWBCT-VTOVKPRRSA-N
Standard InCHI:	InChI=1S/C21H28O4/c1-11(2)13-16(23)14-12(9-22)19-20(3,4)7-6-8-21(19,5)15(14)18-17(13)24-10-25-18/h9,11-12,19,23H,6-8,10H2,1-5H3/t12-,19-,21+/m0/s1
SMILES:	O=C[C@H]1c2c(O)c(C(C)C)c3c(c2[C@@]2([C@@H]1C(C)(C)CCC2)C)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088069
PubChem CID:	15276284
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	twig	n.a.	PMID[22474975]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31347365]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014350]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	8300.0	nM	PMID[469461]

☑ 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 NPC48105 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	392
0.1-0.2	1839
0.2-0.3	3757
0.3-0.4	8981
0.4-0.5	10465
0.5-0.6	4742
0.6-0.7	9893
0.7-0.8	2577
0.8-0.85	45
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.94	High Similarity	NPC50269
0.915	High Similarity	NPC218628
0.8734	High Similarity	NPC276815
0.8734	High Similarity	NPC25850
0.8679	High Similarity	NPC283301
0.8375	Intermediate Similarity	NPC273248
0.8313	Intermediate Similarity	NPC161778
0.8293	Intermediate Similarity	NPC65746
0.828	Intermediate Similarity	NPC116019
0.8253	Intermediate Similarity	NPC102372
0.8221	Intermediate Similarity	NPC474990
0.8193	Intermediate Similarity	NPC173587
0.8193	Intermediate Similarity	NPC208120
0.8187	Intermediate Similarity	NPC196771
0.8165	Intermediate Similarity	NPC169682
0.8155	Intermediate Similarity	NPC232936
0.8144	Intermediate Similarity	NPC21016
0.8144	Intermediate Similarity	NPC146584
0.8118	Intermediate Similarity	NPC292794
0.8113	Intermediate Similarity	NPC304821
0.811	Intermediate Similarity	NPC163527
0.811	Intermediate Similarity	NPC115281
0.811	Intermediate Similarity	NPC19947
0.811	Intermediate Similarity	NPC207584
0.811	Intermediate Similarity	NPC181168
0.8107	Intermediate Similarity	NPC213416
0.8095	Intermediate Similarity	NPC174734
0.8095	Intermediate Similarity	NPC474042
0.8086	Intermediate Similarity	NPC245948
0.8086	Intermediate Similarity	NPC38469
0.8084	Intermediate Similarity	NPC475055
0.805	Intermediate Similarity	NPC58752
0.8049	Intermediate Similarity	NPC32373
0.8049	Intermediate Similarity	NPC237946
0.8037	Intermediate Similarity	NPC273578
0.8037	Intermediate Similarity	NPC103197
0.8037	Intermediate Similarity	NPC30009
0.8012	Intermediate Similarity	NPC303989
0.8012	Intermediate Similarity	NPC91634
0.8012	Intermediate Similarity	NPC268718
0.8012	Intermediate Similarity	NPC150943
0.8012	Intermediate Similarity	NPC474770
0.8	Intermediate Similarity	NPC117911
0.8	Intermediate Similarity	NPC470757
0.7989	Intermediate Similarity	NPC329161
0.7989	Intermediate Similarity	NPC470091
0.7989	Intermediate Similarity	NPC240887
0.7987	Intermediate Similarity	NPC33832
0.7987	Intermediate Similarity	NPC87295
0.7976	Intermediate Similarity	NPC475865
0.7976	Intermediate Similarity	NPC29055
0.7964	Intermediate Similarity	NPC288149
0.7953	Intermediate Similarity	NPC477670
0.7952	Intermediate Similarity	NPC472565
0.7941	Intermediate Similarity	NPC471180
0.7929	Intermediate Similarity	NPC327652
0.7917	Intermediate Similarity	NPC116838
0.7917	Intermediate Similarity	NPC22130
0.7917	Intermediate Similarity	NPC215612
0.7917	Intermediate Similarity	NPC469575
0.7907	Intermediate Similarity	NPC223375
0.7907	Intermediate Similarity	NPC471181
0.7907	Intermediate Similarity	NPC475825
0.7904	Intermediate Similarity	NPC470358
0.7904	Intermediate Similarity	NPC96593
0.7904	Intermediate Similarity	NPC119910
0.7901	Intermediate Similarity	NPC149505
0.7901	Intermediate Similarity	NPC177830
0.7892	Intermediate Similarity	NPC167595
0.7885	Intermediate Similarity	NPC9068
0.7882	Intermediate Similarity	NPC329119
0.7879	Intermediate Similarity	NPC188962
0.7879	Intermediate Similarity	NPC42871
0.7879	Intermediate Similarity	NPC202249
0.7871	Intermediate Similarity	NPC197166
0.787	Intermediate Similarity	NPC116759
0.787	Intermediate Similarity	NPC469518
0.787	Intermediate Similarity	NPC14294
0.787	Intermediate Similarity	NPC469475
0.7866	Intermediate Similarity	NPC20337
0.7866	Intermediate Similarity	NPC477960
0.7866	Intermediate Similarity	NPC474514
0.7866	Intermediate Similarity	NPC477961
0.7866	Intermediate Similarity	NPC477962
0.7861	Intermediate Similarity	NPC470942
0.7853	Intermediate Similarity	NPC474975
0.7853	Intermediate Similarity	NPC210642
0.7853	Intermediate Similarity	NPC13985
0.7849	Intermediate Similarity	NPC246716
0.7849	Intermediate Similarity	NPC17219
0.7849	Intermediate Similarity	NPC239440
0.7849	Intermediate Similarity	NPC20543
0.7844	Intermediate Similarity	NPC45846
0.7844	Intermediate Similarity	NPC475095
0.7844	Intermediate Similarity	NPC215375
0.7844	Intermediate Similarity	NPC125713
0.7844	Intermediate Similarity	NPC62518
0.784	Intermediate Similarity	NPC174512
0.784	Intermediate Similarity	NPC472567
0.784	Intermediate Similarity	NPC477695
0.784	Intermediate Similarity	NPC668
0.784	Intermediate Similarity	NPC145569
0.784	Intermediate Similarity	NPC293757
0.784	Intermediate Similarity	NPC474965
0.784	Intermediate Similarity	NPC216223
0.7836	Intermediate Similarity	NPC45760
0.7836	Intermediate Similarity	NPC272485
0.7836	Intermediate Similarity	NPC292788
0.7829	Intermediate Similarity	NPC258483
0.7826	Intermediate Similarity	NPC65574
0.7826	Intermediate Similarity	NPC80230
0.7826	Intermediate Similarity	NPC104024
0.7826	Intermediate Similarity	NPC246229
0.7826	Intermediate Similarity	NPC304687
0.7826	Intermediate Similarity	NPC101755
0.7826	Intermediate Similarity	NPC191899
0.7824	Intermediate Similarity	NPC25361
0.7811	Intermediate Similarity	NPC476244
0.7811	Intermediate Similarity	NPC474763
0.7811	Intermediate Similarity	NPC469512
0.7805	Intermediate Similarity	NPC477673
0.7805	Intermediate Similarity	NPC477672
0.7805	Intermediate Similarity	NPC220577
0.7805	Intermediate Similarity	NPC104353
0.7805	Intermediate Similarity	NPC477699
0.7799	Intermediate Similarity	NPC474808
0.7798	Intermediate Similarity	NPC155302
0.7798	Intermediate Similarity	NPC161947
0.7798	Intermediate Similarity	NPC21046
0.7791	Intermediate Similarity	NPC26568
0.7791	Intermediate Similarity	NPC24425
0.7791	Intermediate Similarity	NPC211309
0.7785	Intermediate Similarity	NPC475907
0.7784	Intermediate Similarity	NPC179732
0.7784	Intermediate Similarity	NPC220462
0.7778	Intermediate Similarity	NPC71726
0.7778	Intermediate Similarity	NPC261502
0.7778	Intermediate Similarity	NPC165460
0.7778	Intermediate Similarity	NPC472452
0.7771	Intermediate Similarity	NPC478238
0.7771	Intermediate Similarity	NPC30951
0.7771	Intermediate Similarity	NPC238834
0.7771	Intermediate Similarity	NPC6369
0.7771	Intermediate Similarity	NPC478050
0.7771	Intermediate Similarity	NPC472048
0.7765	Intermediate Similarity	NPC317781
0.7765	Intermediate Similarity	NPC156082
0.7765	Intermediate Similarity	NPC197168
0.7764	Intermediate Similarity	NPC471689
0.7764	Intermediate Similarity	NPC75694
0.7764	Intermediate Similarity	NPC472560
0.7759	Intermediate Similarity	NPC181523
0.7758	Intermediate Similarity	NPC178574
0.7758	Intermediate Similarity	NPC65591
0.7751	Intermediate Similarity	NPC152424
0.7751	Intermediate Similarity	NPC87431
0.7751	Intermediate Similarity	NPC260640
0.7751	Intermediate Similarity	NPC295009
0.7751	Intermediate Similarity	NPC100465
0.7751	Intermediate Similarity	NPC66288
0.7746	Intermediate Similarity	NPC1827
0.7746	Intermediate Similarity	NPC10576
0.7744	Intermediate Similarity	NPC303519
0.7744	Intermediate Similarity	NPC477700
0.7744	Intermediate Similarity	NPC234152
0.7744	Intermediate Similarity	NPC163002
0.7738	Intermediate Similarity	NPC474043
0.7736	Intermediate Similarity	NPC191231
0.7733	Intermediate Similarity	NPC185498
0.773	Intermediate Similarity	NPC177476
0.773	Intermediate Similarity	NPC477698
0.773	Intermediate Similarity	NPC471852
0.773	Intermediate Similarity	NPC262455
0.773	Intermediate Similarity	NPC470359
0.7727	Intermediate Similarity	NPC29587
0.7725	Intermediate Similarity	NPC109765
0.7725	Intermediate Similarity	NPC197751
0.7722	Intermediate Similarity	NPC284464
0.7719	Intermediate Similarity	NPC326520
0.7719	Intermediate Similarity	NPC112981
0.7719	Intermediate Similarity	NPC222531
0.7719	Intermediate Similarity	NPC473286
0.7714	Intermediate Similarity	NPC469438
0.7714	Intermediate Similarity	NPC139350
0.7714	Intermediate Similarity	NPC289147
0.7714	Intermediate Similarity	NPC469354
0.7714	Intermediate Similarity	NPC236327
0.7714	Intermediate Similarity	NPC290304
0.7711	Intermediate Similarity	NPC477669
0.7711	Intermediate Similarity	NPC77430
0.7711	Intermediate Similarity	NPC136757
0.7706	Intermediate Similarity	NPC198796
0.7702	Intermediate Similarity	NPC180953
0.7701	Intermediate Similarity	NPC307286
0.7701	Intermediate Similarity	NPC471688
0.7701	Intermediate Similarity	NPC178737
0.7697	Intermediate Similarity	NPC470332
0.7697	Intermediate Similarity	NPC75377
0.7697	Intermediate Similarity	NPC279061
0.7697	Intermediate Similarity	NPC56184

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 NPC48105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	1092
0.2-0.3	2268
0.3-0.4	2806
0.4-0.5	1625
0.5-0.6	708
0.6-0.7	275
0.7-0.8	33
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8086	Intermediate Similarity	NPD37	Approved
0.8061	Intermediate Similarity	NPD6234	Discontinued
0.8049	Intermediate Similarity	NPD4966	Approved
0.8049	Intermediate Similarity	NPD4965	Approved
0.8049	Intermediate Similarity	NPD4967	Phase 2
0.7964	Intermediate Similarity	NPD7199	Phase 2
0.787	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7733	Intermediate Similarity	NPD7228	Approved
0.7602	Intermediate Similarity	NPD6232	Discontinued
0.7572	Intermediate Similarity	NPD7473	Discontinued
0.7486	Intermediate Similarity	NPD5844	Phase 1
0.7389	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7240	Approved
0.733	Intermediate Similarity	NPD3818	Discontinued
0.7321	Intermediate Similarity	NPD7028	Phase 2
0.7283	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2800	Approved
0.7239	Intermediate Similarity	NPD6674	Discontinued
0.7238	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD5711	Approved
0.7193	Intermediate Similarity	NPD2801	Approved
0.7188	Intermediate Similarity	NPD6651	Approved
0.7167	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD6100	Approved
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3882	Suspended
0.7093	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7074	Phase 3
0.7035	Intermediate Similarity	NPD1934	Approved
0.7033	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7054	Approved
0.6994	Remote Similarity	NPD1465	Phase 2
0.6989	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.697	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7472	Approved
0.6959	Remote Similarity	NPD7458	Discontinued
0.6949	Remote Similarity	NPD6959	Discontinued
0.6949	Remote Similarity	NPD1247	Approved
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7229	Phase 3
0.6903	Remote Similarity	NPD3705	Approved
0.6886	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7685	Pre-registration
0.6875	Remote Similarity	NPD3027	Phase 3
0.6854	Remote Similarity	NPD8127	Discontinued
0.6852	Remote Similarity	NPD3620	Phase 2
0.6852	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7808	Phase 3
0.6832	Remote Similarity	NPD7985	Registered
0.6831	Remote Similarity	NPD6797	Phase 2
0.6821	Remote Similarity	NPD7680	Approved
0.68	Remote Similarity	NPD7819	Suspended
0.6793	Remote Similarity	NPD7251	Discontinued
0.6792	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4110	Phase 3
0.678	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6696	Suspended
0.6761	Remote Similarity	NPD3817	Phase 2
0.6747	Remote Similarity	NPD2935	Discontinued
0.6742	Remote Similarity	NPD919	Approved
0.674	Remote Similarity	NPD6166	Phase 2
0.674	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4380	Phase 2
0.6724	Remote Similarity	NPD6599	Discontinued
0.6722	Remote Similarity	NPD3787	Discontinued
0.6721	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD230	Phase 1
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5761	Phase 2
0.6705	Remote Similarity	NPD1653	Approved
0.6705	Remote Similarity	NPD5760	Phase 2
0.6686	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD6781	Approved
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD6778	Approved
0.6667	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD6782	Approved
0.6648	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7340	Approved
0.6614	Remote Similarity	NPD8434	Phase 2
0.6592	Remote Similarity	NPD7075	Discontinued
0.659	Remote Similarity	NPD1512	Approved
0.6587	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1510	Phase 2
0.6576	Remote Similarity	NPD3751	Discontinued
0.6573	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD8151	Discontinued
0.6566	Remote Similarity	NPD7698	Approved
0.6566	Remote Similarity	NPD7696	Phase 3
0.6566	Remote Similarity	NPD7697	Approved
0.6566	Remote Similarity	NPD7435	Discontinued
0.6564	Remote Similarity	NPD4625	Phase 3
0.6559	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD920	Approved
0.6548	Remote Similarity	NPD2438	Suspended
0.6545	Remote Similarity	NPD4060	Phase 1
0.6545	Remote Similarity	NPD2979	Phase 3
0.6545	Remote Similarity	NPD1613	Approved
0.6545	Remote Similarity	NPD1240	Approved
0.6545	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD8313	Approved
0.6543	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2861	Phase 2
0.6543	Remote Similarity	NPD8312	Approved
0.6543	Remote Similarity	NPD9494	Approved
0.6536	Remote Similarity	NPD1398	Phase 1
0.6533	Remote Similarity	NPD7871	Phase 2
0.6533	Remote Similarity	NPD7870	Phase 2
0.6524	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5762	Approved
0.6509	Remote Similarity	NPD5763	Approved
0.6503	Remote Similarity	NPD3926	Phase 2
0.6503	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1357	Approved
0.6495	Remote Similarity	NPD6535	Approved
0.6495	Remote Similarity	NPD6534	Approved
0.6491	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7003	Approved
0.6491	Remote Similarity	NPD3750	Approved
0.6485	Remote Similarity	NPD6663	Approved
0.6478	Remote Similarity	NPD1281	Approved
0.6474	Remote Similarity	NPD7390	Discontinued
0.6465	Remote Similarity	NPD2493	Approved
0.6465	Remote Similarity	NPD2494	Approved
0.6461	Remote Similarity	NPD6801	Discontinued
0.6456	Remote Similarity	NPD2932	Approved
0.6456	Remote Similarity	NPD3019	Approved
0.645	Remote Similarity	NPD1551	Phase 2
0.645	Remote Similarity	NPD4583	Approved
0.645	Remote Similarity	NPD4582	Approved
0.6437	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7701	Phase 2
0.6432	Remote Similarity	NPD6823	Phase 2
0.6429	Remote Similarity	NPD2973	Approved
0.6429	Remote Similarity	NPD2974	Approved
0.6429	Remote Similarity	NPD2975	Approved
0.6425	Remote Similarity	NPD8455	Phase 2
0.6422	Remote Similarity	NPD7801	Approved
0.6422	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7783	Phase 2
0.6414	Remote Similarity	NPD4580	Approved
0.6413	Remote Similarity	NPD5242	Approved
0.6412	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD3749	Approved
0.6407	Remote Similarity	NPD3657	Discovery
0.6407	Remote Similarity	NPD6355	Discontinued
0.6404	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7411	Suspended
0.6402	Remote Similarity	NPD4908	Phase 1
0.64	Remote Similarity	NPD4004	Approved
0.64	Remote Similarity	NPD6273	Approved
0.64	Remote Similarity	NPD4002	Approved
0.64	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4749	Approved
0.6396	Remote Similarity	NPD7699	Phase 2
0.6396	Remote Similarity	NPD7700	Phase 2
0.6395	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1651	Approved
0.639	Remote Similarity	NPD7827	Phase 1
0.6389	Remote Similarity	NPD5353	Approved
0.6386	Remote Similarity	NPD8032	Phase 2
0.6384	Remote Similarity	NPD3226	Approved
0.6382	Remote Similarity	NPD3450	Approved
0.6382	Remote Similarity	NPD3452	Approved
0.6379	Remote Similarity	NPD6799	Approved
0.6374	Remote Similarity	NPD1549	Phase 2
0.6373	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7874	Approved
0.6369	Remote Similarity	NPD7644	Approved
0.6369	Remote Similarity	NPD4097	Suspended
0.6364	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7315	Approved
0.6358	Remote Similarity	NPD6190	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