NPASS Compound

Structure

NPC308572 OpenBabel07101718332D 21 24 0 0 1 0 0 0 0 0999 V2000 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 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 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 13 2 0 0 0 0 10 13 1 0 0 0 0 11 12 2 0 0 0 0 11 14 1 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 18 1 1 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 17 18 1 6 0 0 0 18 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.16
Volume:	301.483
LogP:	3.908
LogD:	3.189
LogS:	-4.724
# Rotatable Bonds:	0
TPSA:	49.83
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	4.614
Fsp3:	0.611
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:	-4.676
MDCK Permeability:	2.336208854103461e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.086

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219
Plasma Protein Binding (PPB):	92.60192108154297%
Volume Distribution (VD):	0.87
Pgp-substrate:	5.068211555480957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.461
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.701
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.473
CYP2C9-substrate:	0.672
CYP2D6-inhibitor:	0.335
CYP2D6-substrate:	0.845
CYP3A4-inhibitor:	0.341
CYP3A4-substrate:	0.463

ADMET: Excretion

Clearance (CL):	4.211
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.28
AMES Toxicity:	0.751
Rat Oral Acute Toxicity:	0.302
Maximum Recommended Daily Dose:	0.416
Skin Sensitization:	0.699
Carcinogencity:	0.216
Eye Corrosion:	0.007
Eye Irritation:	0.93
Respiratory Toxicity:	0.323

Download Data

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

Natural Product: NPC308572

Natural Product ID:	NPC308572
*Common Name:**	RYPYYHNKJXACLY-CGTJXYLNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RYPYYHNKJXACLY-CGTJXYLNSA-N
Standard InCHI:	InChI=1S/C18H22O3/c1-10-8-11-12(9-13(10)19)17(4)7-5-6-16(2,3)18(17)15(21-18)14(11)20/h8-9,15,19H,5-7H2,1-4H3/t15-,17+,18+/m0/s1
SMILES:	O=C1c2cc(C)c(cc2[C@@]2([C@@]3([C@H]1O3)C(C)(C)CCC2)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3261111
PubChem CID:	86302555
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	Eukaryota	Roots	Yucatan Peninsula	n.a.	PMID[24709561]
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	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	3

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	5900.0	nM	PMID[529873]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3100.0	nM	PMID[529873]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	70000.0	nM	PMID[529873]
NPT165	Cell Line	HeLa	Homo sapiens	Ratio IC50	>	11.9	n.a.	PMID[529873]
NPT165	Cell Line	HeLa	Homo sapiens	Ratio IC50	>	22.6	n.a.	PMID[529873]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Ratio IC50	>	3.0	n.a.	PMID[529873]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	70000.0	nM	PMID[529873]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23500.0	nM	PMID[529873]

☑ 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 NPC308572 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	359
0.1-0.2	1490
0.2-0.3	2991
0.3-0.4	7428
0.4-0.5	11245
0.5-0.6	6477
0.6-0.7	8605
0.7-0.8	3945
0.8-0.85	133
0.85-0.9	23
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9051	High Similarity	NPC78307
0.8966	High Similarity	NPC5568
0.8936	High Similarity	NPC114620
0.8936	High Similarity	NPC103337
0.8836	High Similarity	NPC472135
0.8794	High Similarity	NPC475957
0.8768	High Similarity	NPC471851
0.8759	High Similarity	NPC171460
0.875	High Similarity	NPC78364
0.875	High Similarity	NPC176130
0.875	High Similarity	NPC69424
0.875	High Similarity	NPC84672
0.8716	High Similarity	NPC120171
0.8714	High Similarity	NPC202225
0.8707	High Similarity	NPC215593
0.8696	High Similarity	NPC108129
0.869	High Similarity	NPC100242
0.8676	High Similarity	NPC254492
0.8649	High Similarity	NPC142846
0.8643	High Similarity	NPC477139
0.8639	High Similarity	NPC472134
0.863	High Similarity	NPC29932
0.8623	High Similarity	NPC303910
0.8621	High Similarity	NPC248068
0.8613	High Similarity	NPC72667
0.8571	High Similarity	NPC165612
0.8571	High Similarity	NPC478160
0.8553	High Similarity	NPC314257
0.8551	High Similarity	NPC3009
0.8514	High Similarity	NPC470570
0.8514	High Similarity	NPC136878
0.8511	High Similarity	NPC49742
0.8503	High Similarity	NPC471906
0.8493	Intermediate Similarity	NPC135524
0.8493	Intermediate Similarity	NPC201297
0.8489	Intermediate Similarity	NPC276238
0.8477	Intermediate Similarity	NPC205918
0.8467	Intermediate Similarity	NPC123506
0.8467	Intermediate Similarity	NPC474310
0.8462	Intermediate Similarity	NPC38158
0.8446	Intermediate Similarity	NPC474630
0.8446	Intermediate Similarity	NPC34482
0.844	Intermediate Similarity	NPC309430
0.8435	Intermediate Similarity	NPC478164
0.8431	Intermediate Similarity	NPC478133
0.8425	Intermediate Similarity	NPC305845
0.8425	Intermediate Similarity	NPC204045
0.8403	Intermediate Similarity	NPC119542
0.8403	Intermediate Similarity	NPC53001
0.84	Intermediate Similarity	NPC94781
0.8394	Intermediate Similarity	NPC199273
0.8389	Intermediate Similarity	NPC63918
0.8389	Intermediate Similarity	NPC285122
0.838	Intermediate Similarity	NPC314048
0.8378	Intermediate Similarity	NPC48762
0.8369	Intermediate Similarity	NPC476847
0.8369	Intermediate Similarity	NPC41847
0.8367	Intermediate Similarity	NPC474961
0.8366	Intermediate Similarity	NPC472211
0.8356	Intermediate Similarity	NPC315578
0.8356	Intermediate Similarity	NPC471853
0.8345	Intermediate Similarity	NPC13715
0.8345	Intermediate Similarity	NPC230811
0.8345	Intermediate Similarity	NPC87723
0.8344	Intermediate Similarity	NPC44378
0.8344	Intermediate Similarity	NPC280753
0.8333	Intermediate Similarity	NPC191976
0.8333	Intermediate Similarity	NPC474311
0.8333	Intermediate Similarity	NPC137750
0.8333	Intermediate Similarity	NPC471670
0.8322	Intermediate Similarity	NPC12070
0.8322	Intermediate Similarity	NPC170055
0.8311	Intermediate Similarity	NPC143898
0.8311	Intermediate Similarity	NPC354984
0.8299	Intermediate Similarity	NPC110810
0.8298	Intermediate Similarity	NPC253488
0.8289	Intermediate Similarity	NPC477914
0.8289	Intermediate Similarity	NPC470568
0.8288	Intermediate Similarity	NPC242994
0.8288	Intermediate Similarity	NPC138099
0.8288	Intermediate Similarity	NPC26924
0.8286	Intermediate Similarity	NPC96024
0.828	Intermediate Similarity	NPC478134
0.8276	Intermediate Similarity	NPC471905
0.8273	Intermediate Similarity	NPC71610
0.8264	Intermediate Similarity	NPC283088
0.8264	Intermediate Similarity	NPC249272
0.8261	Intermediate Similarity	NPC173978
0.8261	Intermediate Similarity	NPC181334
0.8258	Intermediate Similarity	NPC474360
0.8255	Intermediate Similarity	NPC218866
0.8255	Intermediate Similarity	NPC300684
0.8255	Intermediate Similarity	NPC84568
0.8255	Intermediate Similarity	NPC193703
0.8255	Intermediate Similarity	NPC21599
0.8255	Intermediate Similarity	NPC48130
0.8255	Intermediate Similarity	NPC79627
0.8255	Intermediate Similarity	NPC477913
0.8255	Intermediate Similarity	NPC244691
0.8252	Intermediate Similarity	NPC111845
0.8252	Intermediate Similarity	NPC254603
0.8252	Intermediate Similarity	NPC267205
0.8252	Intermediate Similarity	NPC52407
0.8252	Intermediate Similarity	NPC114183
0.8248	Intermediate Similarity	NPC282577
0.8239	Intermediate Similarity	NPC472049
0.8239	Intermediate Similarity	NPC474517
0.8239	Intermediate Similarity	NPC314653
0.8239	Intermediate Similarity	NPC72669
0.8239	Intermediate Similarity	NPC316262
0.8235	Intermediate Similarity	NPC470569
0.8235	Intermediate Similarity	NPC478148
0.8235	Intermediate Similarity	NPC474417
0.8235	Intermediate Similarity	NPC149526
0.8231	Intermediate Similarity	NPC169452
0.8231	Intermediate Similarity	NPC181560
0.8227	Intermediate Similarity	NPC99731
0.8219	Intermediate Similarity	NPC173980
0.8217	Intermediate Similarity	NPC313368
0.8212	Intermediate Similarity	NPC34802
0.8212	Intermediate Similarity	NPC476821
0.8212	Intermediate Similarity	NPC119767
0.8207	Intermediate Similarity	NPC254847
0.8207	Intermediate Similarity	NPC315275
0.8207	Intermediate Similarity	NPC86524
0.8205	Intermediate Similarity	NPC272196
0.8201	Intermediate Similarity	NPC87985
0.8194	Intermediate Similarity	NPC270899
0.8188	Intermediate Similarity	NPC273683
0.8188	Intermediate Similarity	NPC471187
0.8188	Intermediate Similarity	NPC159721
0.8188	Intermediate Similarity	NPC198014
0.8182	Intermediate Similarity	NPC154683
0.8182	Intermediate Similarity	NPC70622
0.8182	Intermediate Similarity	NPC40356
0.8176	Intermediate Similarity	NPC2681
0.8176	Intermediate Similarity	NPC272907
0.8175	Intermediate Similarity	NPC154696
0.8169	Intermediate Similarity	NPC198305
0.8169	Intermediate Similarity	NPC27659
0.8163	Intermediate Similarity	NPC190457
0.8158	Intermediate Similarity	NPC112816
0.8158	Intermediate Similarity	NPC470479
0.8156	Intermediate Similarity	NPC229894
0.8156	Intermediate Similarity	NPC48248
0.8156	Intermediate Similarity	NPC282923
0.8151	Intermediate Similarity	NPC6100
0.8151	Intermediate Similarity	NPC156888
0.8151	Intermediate Similarity	NPC470721
0.8151	Intermediate Similarity	NPC290601
0.8151	Intermediate Similarity	NPC53206
0.8151	Intermediate Similarity	NPC470722
0.8151	Intermediate Similarity	NPC53414
0.8146	Intermediate Similarity	NPC477208
0.8146	Intermediate Similarity	NPC147250
0.8146	Intermediate Similarity	NPC143685
0.8138	Intermediate Similarity	NPC22644
0.8138	Intermediate Similarity	NPC80035
0.8133	Intermediate Similarity	NPC260152
0.8133	Intermediate Similarity	NPC151607
0.8133	Intermediate Similarity	NPC42540
0.8129	Intermediate Similarity	NPC68756
0.8129	Intermediate Similarity	NPC182921
0.8129	Intermediate Similarity	NPC474824
0.8129	Intermediate Similarity	NPC152525
0.8129	Intermediate Similarity	NPC218870
0.8129	Intermediate Similarity	NPC470408
0.8125	Intermediate Similarity	NPC73544
0.8125	Intermediate Similarity	NPC4170
0.8125	Intermediate Similarity	NPC171968
0.8125	Intermediate Similarity	NPC138472
0.8125	Intermediate Similarity	NPC115458
0.8121	Intermediate Similarity	NPC19631
0.8121	Intermediate Similarity	NPC469520
0.8121	Intermediate Similarity	NPC85310
0.8121	Intermediate Similarity	NPC239136
0.8121	Intermediate Similarity	NPC193555
0.8117	Intermediate Similarity	NPC230848
0.8117	Intermediate Similarity	NPC72958
0.8117	Intermediate Similarity	NPC232645
0.8116	Intermediate Similarity	NPC11250
0.8116	Intermediate Similarity	NPC176208
0.8112	Intermediate Similarity	NPC18798
0.8112	Intermediate Similarity	NPC164295
0.8112	Intermediate Similarity	NPC17083
0.8112	Intermediate Similarity	NPC93015
0.8108	Intermediate Similarity	NPC168471
0.8105	Intermediate Similarity	NPC84142
0.8105	Intermediate Similarity	NPC478219
0.8105	Intermediate Similarity	NPC329933
0.8101	Intermediate Similarity	NPC284495
0.8101	Intermediate Similarity	NPC472618
0.8099	Intermediate Similarity	NPC117899
0.8095	Intermediate Similarity	NPC416
0.8095	Intermediate Similarity	NPC61398
0.8092	Intermediate Similarity	NPC56433
0.8092	Intermediate Similarity	NPC190648
0.8092	Intermediate Similarity	NPC126767
0.8092	Intermediate Similarity	NPC245584
0.8092	Intermediate Similarity	NPC289042

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 NPC308572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	935
0.2-0.3	1519
0.3-0.4	2747
0.4-0.5	2127
0.5-0.6	1045
0.6-0.7	408
0.7-0.8	45
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
0.8207	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD1201	Approved
0.7943	Intermediate Similarity	NPD1470	Approved
0.7895	Intermediate Similarity	NPD7390	Discontinued
0.7785	Intermediate Similarity	NPD5406	Approved
0.7785	Intermediate Similarity	NPD5404	Approved
0.7785	Intermediate Similarity	NPD5408	Approved
0.7785	Intermediate Similarity	NPD5405	Approved
0.7716	Intermediate Similarity	NPD6959	Discontinued
0.7698	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3019	Approved
0.7613	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7819	Suspended
0.7532	Intermediate Similarity	NPD3226	Approved
0.7531	Intermediate Similarity	NPD7075	Discontinued
0.7518	Intermediate Similarity	NPD2932	Approved
0.7516	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD6663	Approved
0.7484	Intermediate Similarity	NPD6599	Discontinued
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD7003	Approved
0.7467	Intermediate Similarity	NPD1607	Approved
0.7466	Intermediate Similarity	NPD5736	Approved
0.7453	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6100	Approved
0.7434	Intermediate Similarity	NPD6099	Approved
0.7432	Intermediate Similarity	NPD3764	Approved
0.7429	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8150	Discontinued
0.7389	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4380	Phase 2
0.7372	Intermediate Similarity	NPD3300	Phase 2
0.7368	Intermediate Similarity	NPD1510	Phase 2
0.7357	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6232	Discontinued
0.7338	Intermediate Similarity	NPD1549	Phase 2
0.7338	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1240	Approved
0.7321	Intermediate Similarity	NPD7473	Discontinued
0.732	Intermediate Similarity	NPD2796	Approved
0.7312	Intermediate Similarity	NPD7458	Discontinued
0.7284	Intermediate Similarity	NPD6801	Discontinued
0.7273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3882	Suspended
0.7255	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD9545	Approved
0.7244	Intermediate Similarity	NPD8166	Discontinued
0.7241	Intermediate Similarity	NPD3972	Approved
0.7235	Intermediate Similarity	NPD5844	Phase 1
0.7233	Intermediate Similarity	NPD6273	Approved
0.7222	Intermediate Similarity	NPD7411	Suspended
0.7219	Intermediate Similarity	NPD943	Approved
0.7214	Intermediate Similarity	NPD5951	Approved
0.7208	Intermediate Similarity	NPD2935	Discontinued
0.7197	Intermediate Similarity	NPD6190	Approved
0.7178	Intermediate Similarity	NPD1934	Approved
0.716	Intermediate Similarity	NPD6166	Phase 2
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7236	Approved
0.7151	Intermediate Similarity	NPD6535	Approved
0.7151	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3091	Approved
0.7119	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6799	Approved
0.7103	Intermediate Similarity	NPD3026	Approved
0.7103	Intermediate Similarity	NPD3023	Approved
0.7099	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1164	Approved
0.7083	Intermediate Similarity	NPD3024	Approved
0.7083	Intermediate Similarity	NPD3025	Approved
0.7076	Intermediate Similarity	NPD3751	Discontinued
0.707	Intermediate Similarity	NPD2800	Approved
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3092	Approved
0.7051	Intermediate Similarity	NPD2344	Approved
0.7049	Intermediate Similarity	NPD6782	Approved
0.7049	Intermediate Similarity	NPD6777	Approved
0.7049	Intermediate Similarity	NPD6776	Approved
0.7049	Intermediate Similarity	NPD6779	Approved
0.7049	Intermediate Similarity	NPD6780	Approved
0.7049	Intermediate Similarity	NPD6778	Approved
0.7049	Intermediate Similarity	NPD6781	Approved
0.7048	Intermediate Similarity	NPD7768	Phase 2
0.7037	Intermediate Similarity	NPD7239	Suspended
0.7035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7700	Phase 2
0.7033	Intermediate Similarity	NPD7699	Phase 2
0.7032	Intermediate Similarity	NPD2799	Discontinued
0.7027	Intermediate Similarity	NPD7435	Discontinued
0.7025	Intermediate Similarity	NPD3750	Approved
0.702	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7008	Discontinued
0.7019	Intermediate Similarity	NPD1512	Approved
0.7013	Intermediate Similarity	NPD6651	Approved
0.7006	Intermediate Similarity	NPD3749	Approved
0.6989	Remote Similarity	NPD8320	Phase 1
0.6989	Remote Similarity	NPD8319	Approved
0.6988	Remote Similarity	NPD3817	Phase 2
0.6977	Remote Similarity	NPD7177	Discontinued
0.6966	Remote Similarity	NPD1651	Approved
0.6952	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1471	Phase 3
0.6941	Remote Similarity	NPD5711	Approved
0.6941	Remote Similarity	NPD3787	Discontinued
0.6941	Remote Similarity	NPD5710	Approved
0.6935	Remote Similarity	NPD7697	Approved
0.6935	Remote Similarity	NPD7698	Approved
0.6935	Remote Similarity	NPD7696	Phase 3
0.6933	Remote Similarity	NPD2798	Approved
0.6932	Remote Similarity	NPD8313	Approved
0.6932	Remote Similarity	NPD8312	Approved
0.6928	Remote Similarity	NPD2801	Approved
0.6928	Remote Similarity	NPD5761	Phase 2
0.6928	Remote Similarity	NPD5760	Phase 2
0.6923	Remote Similarity	NPD5494	Approved
0.6918	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4626	Approved
0.6914	Remote Similarity	NPD6559	Discontinued
0.6913	Remote Similarity	NPD1283	Approved
0.691	Remote Similarity	NPD8434	Phase 2
0.6905	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7870	Phase 2
0.6898	Remote Similarity	NPD7871	Phase 2
0.6894	Remote Similarity	NPD1511	Approved
0.6883	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD7799	Discontinued
0.6875	Remote Similarity	NPD2309	Approved
0.6867	Remote Similarity	NPD3094	Phase 2
0.6857	Remote Similarity	NPD6797	Phase 2
0.6854	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5691	Approved
0.6839	Remote Similarity	NPD230	Phase 1
0.6835	Remote Similarity	NPD2342	Discontinued
0.6835	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7251	Discontinued
0.6806	Remote Similarity	NPD7874	Approved
0.6806	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4059	Approved
0.6803	Remote Similarity	NPD3095	Discontinued
0.68	Remote Similarity	NPD6696	Suspended
0.6797	Remote Similarity	NPD4625	Phase 3
0.6789	Remote Similarity	NPD7701	Phase 2
0.6786	Remote Similarity	NPD5402	Approved
0.6782	Remote Similarity	NPD3818	Discontinued
0.678	Remote Similarity	NPD7808	Phase 3
0.6772	Remote Similarity	NPD1551	Phase 2
0.677	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5403	Approved
0.6761	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD9493	Approved
0.6753	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2313	Discontinued
0.6753	Remote Similarity	NPD6798	Discontinued
0.6739	Remote Similarity	NPD1237	Approved
0.6736	Remote Similarity	NPD2629	Approved
0.6721	Remote Similarity	NPD6212	Phase 3
0.6721	Remote Similarity	NPD6213	Phase 3
0.6721	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7635	Approved
0.6711	Remote Similarity	NPD1281	Approved
0.671	Remote Similarity	NPD7961	Discontinued
0.671	Remote Similarity	NPD8032	Phase 2
0.6709	Remote Similarity	NPD3748	Approved
0.6709	Remote Similarity	NPD7033	Discontinued
0.6705	Remote Similarity	NPD7074	Phase 3
0.669	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1778	Approved
0.6689	Remote Similarity	NPD1876	Approved
0.6688	Remote Similarity	NPD7095	Approved
0.6687	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD36	Approved
0.6685	Remote Similarity	NPD4954	Approved
0.6685	Remote Similarity	NPD5028	Approved
0.6685	Remote Similarity	NPD5026	Approved
0.6685	Remote Similarity	NPD5034	Approved
0.6685	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4955	Approved
0.6684	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD919	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD2979	Phase 3
0.6648	Remote Similarity	NPD6020	Phase 2
0.6648	Remote Similarity	NPD7054	Approved
0.6647	Remote Similarity	NPD7057	Phase 3

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