NPASS Compound

Structure

NPC218838 OpenBabel07101719152D 23 25 0 0 1 0 0 0 0 0999 V2000 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5254 0.6088 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9568 -1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6516 -0.6741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9909 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1056 0.2169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5075 0.4701 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 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6639 -0.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3985 0.9240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 23 1 0 0 0 0 12 15 2 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 6 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 6 0 0 0 18 20 1 6 0 0 0 18 22 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	3.746
LogD:	4.07
LogS:	-4.261
# Rotatable Bonds:	3
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.83
Synthetic Accessibility Score:	4.609
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.629
MDCK Permeability:	3.5542179830372334e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.108
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.331
30% Bioavailability (F30%):	0.198

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	97.54637908935547%
Volume Distribution (VD):	2.275
Pgp-substrate:	4.112938404083252%

ADMET: Metabolism

CYP1A2-inhibitor:	0.28
CYP1A2-substrate:	0.187
CYP2C19-inhibitor:	0.287
CYP2C19-substrate:	0.418
CYP2C9-inhibitor:	0.524
CYP2C9-substrate:	0.516
CYP2D6-inhibitor:	0.134
CYP2D6-substrate:	0.562
CYP3A4-inhibitor:	0.562
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	10.821
Half-life (T1/2):	0.684

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.841
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.093
Carcinogencity:	0.114
Eye Corrosion:	0.021
Eye Irritation:	0.391
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC218838

Natural Product ID:	NPC218838
*Common Name:**	6Alpha,7Alpha-Dihydroxyannonene
IUPAC Name:	(1R,2S,3S,4R,4aR,8aR)-4-[2-(furan-3-yl)ethyl]-3,4,8,8a-tetramethyl-1,2,3,4a,5,6-hexahydronaphthalene-1,2-diol
Synonyms:	6Alpha,7Alpha-Dihydroxyannonene
Standard InCHIKey:	HAFUEVCORQGSRZ-QIXFSGBHSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13-6-5-7-16-19(3,10-8-15-9-11-23-12-15)14(2)17(21)18(22)20(13,16)4/h6,9,11-12,14,16-18,21-22H,5,7-8,10H2,1-4H3/t14-,16-,17+,18+,19+,20+/m1/s1
SMILES:	CC1=CCC[C@@H]2[C@@](C)(CCc3ccoc3)[C@H](C)[C@@H]([C@@H]([C@@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL475396
PubChem CID:	25195056
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO32668	ptychopetalum olacoides	Species	Olacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18821798]
NPO32668	ptychopetalum olacoides	Species	Olacaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[19095451]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	205.3	um	PMID[558203]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	201.5	um	PMID[558203]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	173.1	um	PMID[558203]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	115.8	um	PMID[558203]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	104.0	um	PMID[558203]

☑ 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 NPC218838 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	260
0.1-0.2	1168
0.2-0.3	2661
0.3-0.4	5833
0.4-0.5	11695
0.5-0.6	9725
0.6-0.7	10197
0.7-0.8	949
0.8-0.85	135
0.85-0.9	64
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC476947
0.9683	High Similarity	NPC61788
0.9286	High Similarity	NPC23086
0.9185	High Similarity	NPC52412
0.9118	High Similarity	NPC476946
0.8993	High Similarity	NPC302987
0.8992	High Similarity	NPC112706
0.8992	High Similarity	NPC207294
0.8986	High Similarity	NPC5676
0.8968	High Similarity	NPC477967
0.8915	High Similarity	NPC83178
0.8897	High Similarity	NPC67003
0.8865	High Similarity	NPC470998
0.8865	High Similarity	NPC234494
0.8837	High Similarity	NPC46536
0.8837	High Similarity	NPC138139
0.8806	High Similarity	NPC158525
0.8803	High Similarity	NPC196846
0.8803	High Similarity	NPC470997
0.8794	High Similarity	NPC471007
0.8788	High Similarity	NPC298190
0.8779	High Similarity	NPC59502
0.8769	High Similarity	NPC290955
0.876	High Similarity	NPC290193
0.8759	High Similarity	NPC90296
0.8741	High Similarity	NPC46896
0.8732	High Similarity	NPC125182
0.8732	High Similarity	NPC69647
0.8714	High Similarity	NPC185456
0.8705	High Similarity	NPC243577
0.8702	High Similarity	NPC477966
0.8702	High Similarity	NPC477123
0.8686	High Similarity	NPC90953
0.8686	High Similarity	NPC202260
0.8681	High Similarity	NPC470996
0.8681	High Similarity	NPC33938
0.8651	High Similarity	NPC243704
0.8647	High Similarity	NPC89133
0.8633	High Similarity	NPC121158
0.8626	High Similarity	NPC246392
0.8615	High Similarity	NPC300098
0.8605	High Similarity	NPC272899
0.8605	High Similarity	NPC16922
0.8592	High Similarity	NPC471174
0.8592	High Similarity	NPC255414
0.8582	High Similarity	NPC473982
0.8562	High Similarity	NPC141538
0.8562	High Similarity	NPC296807
0.8562	High Similarity	NPC92979
0.8562	High Similarity	NPC155939
0.8561	High Similarity	NPC477039
0.8561	High Similarity	NPC329707
0.8561	High Similarity	NPC477040
0.8561	High Similarity	NPC26532
0.8561	High Similarity	NPC279877
0.856	High Similarity	NPC150895
0.8552	High Similarity	NPC294511
0.8552	High Similarity	NPC121615
0.8511	High Similarity	NPC476944
0.8511	High Similarity	NPC251865
0.85	High Similarity	NPC263337
0.8493	Intermediate Similarity	NPC98206
0.8493	Intermediate Similarity	NPC253201
0.8493	Intermediate Similarity	NPC237259
0.8493	Intermediate Similarity	NPC302054
0.8493	Intermediate Similarity	NPC34421
0.8489	Intermediate Similarity	NPC56197
0.8473	Intermediate Similarity	NPC303010
0.8473	Intermediate Similarity	NPC179354
0.8462	Intermediate Similarity	NPC216755
0.8446	Intermediate Similarity	NPC197137
0.8433	Intermediate Similarity	NPC476925
0.8429	Intermediate Similarity	NPC205765
0.8425	Intermediate Similarity	NPC268905
0.8425	Intermediate Similarity	NPC472672
0.8421	Intermediate Similarity	NPC476917
0.8421	Intermediate Similarity	NPC327527
0.8414	Intermediate Similarity	NPC228842
0.8409	Intermediate Similarity	NPC74612
0.8406	Intermediate Similarity	NPC470742
0.8406	Intermediate Similarity	NPC307401
0.8406	Intermediate Similarity	NPC4764
0.8397	Intermediate Similarity	NPC477038
0.8397	Intermediate Similarity	NPC130275
0.8397	Intermediate Similarity	NPC477965
0.8392	Intermediate Similarity	NPC346
0.8392	Intermediate Similarity	NPC470999
0.8385	Intermediate Similarity	NPC473379
0.8385	Intermediate Similarity	NPC471549
0.8385	Intermediate Similarity	NPC317217
0.8382	Intermediate Similarity	NPC471006
0.8358	Intermediate Similarity	NPC198904
0.8345	Intermediate Similarity	NPC236532
0.8345	Intermediate Similarity	NPC195325
0.8345	Intermediate Similarity	NPC471996
0.8345	Intermediate Similarity	NPC472654
0.8333	Intermediate Similarity	NPC146872
0.8333	Intermediate Similarity	NPC474829
0.8322	Intermediate Similarity	NPC472777
0.8322	Intermediate Similarity	NPC194499
0.8322	Intermediate Similarity	NPC472778
0.8322	Intermediate Similarity	NPC472776
0.8311	Intermediate Similarity	NPC264943
0.8311	Intermediate Similarity	NPC214541
0.8311	Intermediate Similarity	NPC44675
0.8309	Intermediate Similarity	NPC471995
0.8299	Intermediate Similarity	NPC469503
0.8281	Intermediate Similarity	NPC212918
0.8273	Intermediate Similarity	NPC310830
0.8267	Intermediate Similarity	NPC475967
0.8267	Intermediate Similarity	NPC472671
0.8261	Intermediate Similarity	NPC92941
0.8258	Intermediate Similarity	NPC243269
0.8258	Intermediate Similarity	NPC178382
0.8252	Intermediate Similarity	NPC199044
0.8252	Intermediate Similarity	NPC238843
0.8243	Intermediate Similarity	NPC178932
0.8243	Intermediate Similarity	NPC57998
0.8239	Intermediate Similarity	NPC475519
0.8231	Intermediate Similarity	NPC272590
0.8227	Intermediate Similarity	NPC148374
0.8222	Intermediate Similarity	NPC120836
0.8222	Intermediate Similarity	NPC223063
0.8219	Intermediate Similarity	NPC471001
0.8217	Intermediate Similarity	NPC87466
0.8214	Intermediate Similarity	NPC472376
0.8209	Intermediate Similarity	NPC474830
0.8209	Intermediate Similarity	NPC476016
0.8207	Intermediate Similarity	NPC250228
0.8207	Intermediate Similarity	NPC71821
0.82	Intermediate Similarity	NPC299038
0.82	Intermediate Similarity	NPC214495
0.82	Intermediate Similarity	NPC88007
0.82	Intermediate Similarity	NPC470118
0.82	Intermediate Similarity	NPC475066
0.82	Intermediate Similarity	NPC470119
0.82	Intermediate Similarity	NPC261597
0.82	Intermediate Similarity	NPC7059
0.8195	Intermediate Similarity	NPC471074
0.8195	Intermediate Similarity	NPC473885
0.8188	Intermediate Similarity	NPC469336
0.8188	Intermediate Similarity	NPC35000
0.8182	Intermediate Similarity	NPC267632
0.8176	Intermediate Similarity	NPC476939
0.8176	Intermediate Similarity	NPC246164
0.8176	Intermediate Similarity	NPC476940
0.817	Intermediate Similarity	NPC276551
0.8168	Intermediate Similarity	NPC97566
0.8163	Intermediate Similarity	NPC5180
0.8163	Intermediate Similarity	NPC212257
0.8158	Intermediate Similarity	NPC470792
0.8158	Intermediate Similarity	NPC149896
0.8158	Intermediate Similarity	NPC79571
0.8158	Intermediate Similarity	NPC211777
0.8158	Intermediate Similarity	NPC18986
0.8158	Intermediate Similarity	NPC69028
0.8158	Intermediate Similarity	NPC200782
0.8151	Intermediate Similarity	NPC476941
0.8151	Intermediate Similarity	NPC476942
0.8151	Intermediate Similarity	NPC93666
0.8146	Intermediate Similarity	NPC475226
0.8146	Intermediate Similarity	NPC307383
0.8146	Intermediate Similarity	NPC84349
0.8143	Intermediate Similarity	NPC170604
0.8143	Intermediate Similarity	NPC215109
0.814	Intermediate Similarity	NPC144745
0.814	Intermediate Similarity	NPC208906
0.8138	Intermediate Similarity	NPC471292
0.8134	Intermediate Similarity	NPC474260
0.8134	Intermediate Similarity	NPC329922
0.8134	Intermediate Similarity	NPC81912
0.8134	Intermediate Similarity	NPC329694
0.8121	Intermediate Similarity	NPC30222
0.812	Intermediate Similarity	NPC118853
0.8117	Intermediate Similarity	NPC470875
0.8116	Intermediate Similarity	NPC470740
0.8116	Intermediate Similarity	NPC293253
0.8112	Intermediate Similarity	NPC62103
0.8112	Intermediate Similarity	NPC20578
0.8108	Intermediate Similarity	NPC291150
0.8108	Intermediate Similarity	NPC471000
0.8108	Intermediate Similarity	NPC116717
0.8106	Intermediate Similarity	NPC36255
0.8105	Intermediate Similarity	NPC292389
0.8105	Intermediate Similarity	NPC283209
0.8105	Intermediate Similarity	NPC472773
0.8105	Intermediate Similarity	NPC469338
0.8105	Intermediate Similarity	NPC198047
0.8099	Intermediate Similarity	NPC473983
0.8099	Intermediate Similarity	NPC201370
0.8092	Intermediate Similarity	NPC287559
0.8092	Intermediate Similarity	NPC477402
0.8092	Intermediate Similarity	NPC8389
0.8092	Intermediate Similarity	NPC470789
0.8088	Intermediate Similarity	NPC208389
0.8085	Intermediate Similarity	NPC476943
0.8085	Intermediate Similarity	NPC220094
0.8082	Intermediate Similarity	NPC476937
0.8082	Intermediate Similarity	NPC476938
0.8079	Intermediate Similarity	NPC45101

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 NPC218838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	894
0.2-0.3	1789
0.3-0.4	2655
0.4-0.5	2057
0.5-0.6	1149
0.6-0.7	338
0.7-0.8	19
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
0.8067	Intermediate Similarity	NPD5760	Phase 2
0.8067	Intermediate Similarity	NPD5761	Phase 2
0.7718	Intermediate Similarity	NPD6273	Approved
0.7655	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4628	Phase 3
0.753	Intermediate Similarity	NPD8434	Phase 2
0.7439	Intermediate Similarity	NPD6764	Approved
0.7439	Intermediate Similarity	NPD6765	Approved
0.7262	Intermediate Similarity	NPD6785	Approved
0.7262	Intermediate Similarity	NPD6784	Approved
0.7192	Intermediate Similarity	NPD6355	Discontinued
0.7181	Intermediate Similarity	NPD1471	Phase 3
0.7181	Intermediate Similarity	NPD2344	Approved
0.7164	Intermediate Similarity	NPD1241	Discontinued
0.7162	Intermediate Similarity	NPD2799	Discontinued
0.7152	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7003	Approved
0.7152	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD3972	Approved
0.7123	Intermediate Similarity	NPD4140	Approved
0.7115	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD8127	Discontinued
0.7075	Intermediate Similarity	NPD5735	Approved
0.7042	Intermediate Similarity	NPD1876	Approved
0.7024	Intermediate Similarity	NPD6559	Discontinued
0.7014	Intermediate Similarity	NPD9494	Approved
0.6993	Remote Similarity	NPD2309	Approved
0.6975	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2346	Discontinued
0.695	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2798	Approved
0.6939	Remote Similarity	NPD8032	Phase 2
0.6934	Remote Similarity	NPD7157	Approved
0.6929	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD8166	Discontinued
0.6923	Remote Similarity	NPD1283	Approved
0.6899	Remote Similarity	NPD7458	Discontinued
0.6899	Remote Similarity	NPD2651	Approved
0.6899	Remote Similarity	NPD2649	Approved
0.6875	Remote Similarity	NPD2797	Approved
0.6871	Remote Similarity	NPD6798	Discontinued
0.6863	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6599	Discontinued
0.6855	Remote Similarity	NPD7028	Phase 2
0.6853	Remote Similarity	NPD5327	Phase 3
0.6842	Remote Similarity	NPD5763	Approved
0.6842	Remote Similarity	NPD5762	Approved
0.6832	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1778	Approved
0.6803	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4534	Discontinued
0.6797	Remote Similarity	NPD2424	Discontinued
0.6796	Remote Similarity	NPD3057	Approved
0.6791	Remote Similarity	NPD2684	Approved
0.6783	Remote Similarity	NPD1608	Approved
0.6779	Remote Similarity	NPD4060	Phase 1
0.6779	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3620	Phase 2
0.6776	Remote Similarity	NPD4476	Approved
0.6776	Remote Similarity	NPD4477	Approved
0.6776	Remote Similarity	NPD2935	Discontinued
0.6776	Remote Similarity	NPD2796	Approved
0.6766	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2313	Discontinued
0.6752	Remote Similarity	NPD4662	Approved
0.6752	Remote Similarity	NPD4661	Approved
0.6748	Remote Similarity	NPD3882	Suspended
0.6746	Remote Similarity	NPD5844	Phase 1
0.6738	Remote Similarity	NPD5585	Approved
0.6738	Remote Similarity	NPD5691	Approved
0.6738	Remote Similarity	NPD1651	Approved
0.6735	Remote Similarity	NPD6832	Phase 2
0.6732	Remote Similarity	NPD6005	Phase 3
0.6732	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6004	Phase 3
0.6732	Remote Similarity	NPD6002	Phase 3
0.6731	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7236	Approved
0.6728	Remote Similarity	NPD7819	Suspended
0.6728	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5494	Approved
0.6713	Remote Similarity	NPD1281	Approved
0.6712	Remote Similarity	NPD5647	Approved
0.6711	Remote Similarity	NPD4308	Phase 3
0.671	Remote Similarity	NPD3750	Approved
0.6703	Remote Similarity	NPD2491	Approved
0.6703	Remote Similarity	NPD3533	Approved
0.6703	Remote Similarity	NPD2972	Approved
0.6691	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4626	Approved
0.669	Remote Similarity	NPD8651	Approved
0.669	Remote Similarity	NPD2932	Approved
0.6689	Remote Similarity	NPD6653	Approved
0.6689	Remote Similarity	NPD7095	Approved
0.6689	Remote Similarity	NPD6353	Approved
0.6688	Remote Similarity	NPD5958	Discontinued
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD919	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD6100	Approved
0.6646	Remote Similarity	NPD4380	Phase 2
0.6646	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2800	Approved
0.6644	Remote Similarity	NPD3268	Approved
0.6644	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD447	Suspended
0.6619	Remote Similarity	NPD2629	Approved
0.6612	Remote Similarity	NPD3448	Approved
0.6606	Remote Similarity	NPD7075	Discontinued
0.6601	Remote Similarity	NPD3748	Approved
0.66	Remote Similarity	NPD4062	Phase 3
0.66	Remote Similarity	NPD6663	Approved
0.66	Remote Similarity	NPD6233	Phase 2
0.6599	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD7843	Approved
0.6593	Remote Similarity	NPD290	Approved
0.6588	Remote Similarity	NPD3818	Discontinued
0.6587	Remote Similarity	NPD1247	Approved
0.6585	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3226	Approved
0.6582	Remote Similarity	NPD6799	Approved
0.6581	Remote Similarity	NPD1549	Phase 2
0.6573	Remote Similarity	NPD3019	Approved
0.6573	Remote Similarity	NPD17	Approved
0.6569	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6279	Approved
0.6564	Remote Similarity	NPD6280	Approved
0.6564	Remote Similarity	NPD6801	Discontinued
0.6564	Remote Similarity	NPD37	Approved
0.6556	Remote Similarity	NPD3142	Approved
0.6556	Remote Similarity	NPD3140	Approved
0.6556	Remote Similarity	NPD4307	Phase 2
0.6554	Remote Similarity	NPD5736	Approved
0.6549	Remote Similarity	NPD1894	Discontinued
0.6545	Remote Similarity	NPD4965	Approved
0.6545	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4967	Phase 2
0.6545	Remote Similarity	NPD4966	Approved
0.6541	Remote Similarity	NPD2534	Approved
0.6541	Remote Similarity	NPD2533	Approved
0.6541	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2532	Approved
0.6538	Remote Similarity	NPD1243	Approved
0.6533	Remote Similarity	NPD411	Approved
0.6533	Remote Similarity	NPD3764	Approved
0.6531	Remote Similarity	NPD1203	Approved
0.6528	Remote Similarity	NPD3496	Discontinued
0.6522	Remote Similarity	NPD7239	Suspended
0.6516	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8404	Phase 2
0.6507	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4359	Approved
0.6506	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6677	Suspended
0.65	Remote Similarity	NPD5049	Phase 3
0.6491	Remote Similarity	NPD2163	Approved
0.6488	Remote Similarity	NPD7199	Phase 2
0.6486	Remote Similarity	NPD4624	Approved
0.6485	Remote Similarity	NPD2296	Approved
0.6479	Remote Similarity	NPD9092	Discovery
0.6478	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6166	Phase 2
0.6471	Remote Similarity	NPD1607	Approved
0.6471	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7008	Discontinued
0.6467	Remote Similarity	NPD6234	Discontinued
0.6463	Remote Similarity	NPD6844	Discontinued
0.6463	Remote Similarity	NPD6696	Suspended
0.646	Remote Similarity	NPD3869	Phase 3
0.646	Remote Similarity	NPD3873	Phase 3
0.646	Remote Similarity	NPD5403	Approved
0.6457	Remote Similarity	NPD8312	Approved
0.6457	Remote Similarity	NPD8313	Approved
0.6456	Remote Similarity	NPD3887	Approved
0.6456	Remote Similarity	NPD2354	Approved
0.6452	Remote Similarity	NPD2531	Phase 2
0.6447	Remote Similarity	NPD1240	Approved
0.6446	Remote Similarity	NPD7768	Phase 2
0.6443	Remote Similarity	NPD2861	Phase 2
0.6438	Remote Similarity	NPD5401	Approved
0.6434	Remote Similarity	NPD9545	Approved
0.6433	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7097	Phase 1
0.6424	Remote Similarity	NPD2801	Approved
0.6424	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1699	Clinical (unspecified phase)

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