NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	596.17
Volume:	546.164
LogP:	-0.258
LogD:	-0.086
LogS:	-4.389
# Rotatable Bonds:	6
TPSA:	245.29
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.185
Synthetic Accessibility Score:	4.885
Fsp3:	0.519
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.725
MDCK Permeability:	2.845029484888073e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.81
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	70.71326446533203%
Volume Distribution (VD):	0.365
Pgp-substrate:	26.23347282409668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.562
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.026

ADMET: Excretion

Clearance (CL):	1.562
Half-life (T1/2):	0.762

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.541
Rat Oral Acute Toxicity:	0.222
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.885
Carcinogencity:	0.394
Eye Corrosion:	0.003
Eye Irritation:	0.13
Respiratory Toxicity:	0.201

Download Data

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

Natural Product: NPC70436

Natural Product ID:	NPC70436
*Common Name:**	Mesity alcohol
IUPAC Name:	n.a.
Synonyms:	2,4,6-Trimethyl-Phenol; 2,4,6-Trimethylphenol
Standard InCHIKey:	BPRYUXCVCCNUFE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H12O/c1-6-4-7(2)9(10)8(3)5-6/h4-5,10H,1-3H3
SMILES:	Cc1cc(C)c(c(c1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001272] Cresols [CHEMONTID:0001275] Para cresols

*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
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO42012	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]

☑ 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
NPO42012	NPC70436	Other	Plant	11.5	4	19	mg/100g	Database [DUKE]

☑ 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	1
Others	6
Potency	5

Activity Type	# Activity
Cell Line	1
Organism	2
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	3.2	n.a.	PMID[524109]
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21689.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	611.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IC50	=	1400000.0	nM	PMID[524108]
NPT35	Others	n.a.		LogP	=	2.86	n.a.	PMID[524108]
NPT35	Others	n.a.		pKa	=	10.9	n.a.	PMID[524108]
NPT35	Others	n.a.		LogD	=	2.86	n.a.	PMID[524108]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Log 1/I50	=	2.85	1/M	PMID[524108]
NPT35	Others	n.a.		K	=	8.5	10'-4/M/s	PMID[524110]

☑ 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 NPC70436 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	310
0.1-0.2	2554
0.2-0.3	8312
0.3-0.4	11610
0.4-0.5	6738
0.5-0.6	9035
0.6-0.7	3283
0.7-0.8	672
0.8-0.85	123
0.85-0.9	49
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC204210
0.9438	High Similarity	NPC144682
0.9438	High Similarity	NPC8392
0.9231	High Similarity	NPC77492
0.913	High Similarity	NPC122005
0.913	High Similarity	NPC252821
0.913	High Similarity	NPC128723
0.9111	High Similarity	NPC289769
0.9091	High Similarity	NPC123273
0.9091	High Similarity	NPC318325
0.9091	High Similarity	NPC242240
0.9091	High Similarity	NPC258219
0.908	High Similarity	NPC23167
0.908	High Similarity	NPC407
0.908	High Similarity	NPC307235
0.907	High Similarity	NPC248817
0.907	High Similarity	NPC286904
0.9032	High Similarity	NPC225506
0.8977	High Similarity	NPC113460
0.8977	High Similarity	NPC19680
0.8977	High Similarity	NPC25493
0.8966	High Similarity	NPC155393
0.8966	High Similarity	NPC197783
0.8953	High Similarity	NPC124436
0.8953	High Similarity	NPC265146
0.8901	High Similarity	NPC128062
0.8889	High Similarity	NPC304541
0.8889	High Similarity	NPC306074
0.8876	High Similarity	NPC177420
0.8876	High Similarity	NPC280347
0.8864	High Similarity	NPC184169
0.8851	High Similarity	NPC175313
0.8778	High Similarity	NPC55561
0.8696	High Similarity	NPC27323
0.8696	High Similarity	NPC316301
0.8696	High Similarity	NPC152415
0.8681	High Similarity	NPC231150
0.8681	High Similarity	NPC155908
0.8681	High Similarity	NPC45040
0.8667	High Similarity	NPC98772
0.866	High Similarity	NPC99557
0.866	High Similarity	NPC138942
0.866	High Similarity	NPC243677
0.866	High Similarity	NPC219286
0.866	High Similarity	NPC303141
0.8646	High Similarity	NPC168829
0.8646	High Similarity	NPC470202
0.8632	High Similarity	NPC211885
0.8602	High Similarity	NPC26244
0.8602	High Similarity	NPC222146
0.8587	High Similarity	NPC271440
0.8587	High Similarity	NPC325292
0.8587	High Similarity	NPC138117
0.8571	High Similarity	NPC300017
0.8571	High Similarity	NPC271274
0.8571	High Similarity	NPC21594
0.8557	High Similarity	NPC288411
0.8556	High Similarity	NPC27974
0.8556	High Similarity	NPC104216
0.8542	High Similarity	NPC51015
0.8526	High Similarity	NPC80027
0.8511	High Similarity	NPC312132
0.8511	High Similarity	NPC473388
0.8511	High Similarity	NPC259512
0.8495	Intermediate Similarity	NPC151715
0.8495	Intermediate Similarity	NPC245187
0.8485	Intermediate Similarity	NPC228737
0.8485	Intermediate Similarity	NPC151477
0.8478	Intermediate Similarity	NPC270547
0.8454	Intermediate Similarity	NPC108497
0.8454	Intermediate Similarity	NPC269212
0.8427	Intermediate Similarity	NPC150837
0.8421	Intermediate Similarity	NPC79241
0.8421	Intermediate Similarity	NPC6597
0.8421	Intermediate Similarity	NPC225464
0.8404	Intermediate Similarity	NPC274678
0.8404	Intermediate Similarity	NPC313650
0.84	Intermediate Similarity	NPC470039
0.84	Intermediate Similarity	NPC61885
0.84	Intermediate Similarity	NPC63698
0.8387	Intermediate Similarity	NPC29373
0.8387	Intermediate Similarity	NPC162314
0.8387	Intermediate Similarity	NPC3358
0.8387	Intermediate Similarity	NPC181709
0.8387	Intermediate Similarity	NPC94139
0.8387	Intermediate Similarity	NPC210497
0.8387	Intermediate Similarity	NPC306884
0.8387	Intermediate Similarity	NPC55903
0.8387	Intermediate Similarity	NPC147284
0.8384	Intermediate Similarity	NPC54765
0.837	Intermediate Similarity	NPC192
0.837	Intermediate Similarity	NPC300478
0.837	Intermediate Similarity	NPC47950
0.8367	Intermediate Similarity	NPC238696
0.8367	Intermediate Similarity	NPC272029
0.8333	Intermediate Similarity	NPC33675
0.8333	Intermediate Similarity	NPC92730
0.8333	Intermediate Similarity	NPC299762
0.8317	Intermediate Similarity	NPC471954
0.8317	Intermediate Similarity	NPC75272
0.8317	Intermediate Similarity	NPC58865
0.8283	Intermediate Similarity	NPC117115
0.8247	Intermediate Similarity	NPC129373
0.8247	Intermediate Similarity	NPC48730
0.8247	Intermediate Similarity	NPC72729
0.8247	Intermediate Similarity	NPC174911
0.8247	Intermediate Similarity	NPC248396
0.8235	Intermediate Similarity	NPC296683
0.8235	Intermediate Similarity	NPC13482
0.8235	Intermediate Similarity	NPC224870
0.8229	Intermediate Similarity	NPC260000
0.8229	Intermediate Similarity	NPC152097
0.8229	Intermediate Similarity	NPC475078
0.8218	Intermediate Similarity	NPC262365
0.8218	Intermediate Similarity	NPC95344
0.8211	Intermediate Similarity	NPC246679
0.82	Intermediate Similarity	NPC469913
0.8182	Intermediate Similarity	NPC119860
0.8163	Intermediate Similarity	NPC252105
0.8163	Intermediate Similarity	NPC477685
0.8155	Intermediate Similarity	NPC165770
0.8155	Intermediate Similarity	NPC4493
0.8155	Intermediate Similarity	NPC151537
0.8155	Intermediate Similarity	NPC476632
0.8155	Intermediate Similarity	NPC260323
0.8155	Intermediate Similarity	NPC225679
0.8155	Intermediate Similarity	NPC176279
0.8155	Intermediate Similarity	NPC95716
0.8144	Intermediate Similarity	NPC260775
0.8144	Intermediate Similarity	NPC216468
0.8144	Intermediate Similarity	NPC78119
0.8144	Intermediate Similarity	NPC280869
0.8144	Intermediate Similarity	NPC51333
0.8144	Intermediate Similarity	NPC132078
0.8137	Intermediate Similarity	NPC314187
0.8125	Intermediate Similarity	NPC283711
0.8125	Intermediate Similarity	NPC82664
0.8125	Intermediate Similarity	NPC216520
0.8125	Intermediate Similarity	NPC292730
0.8125	Intermediate Similarity	NPC132271
0.8125	Intermediate Similarity	NPC202986
0.8105	Intermediate Similarity	NPC81010
0.8105	Intermediate Similarity	NPC32977
0.8105	Intermediate Similarity	NPC76938
0.81	Intermediate Similarity	NPC474839
0.8081	Intermediate Similarity	NPC235762
0.8081	Intermediate Similarity	NPC471228
0.8077	Intermediate Similarity	NPC250323
0.8077	Intermediate Similarity	NPC228425
0.8077	Intermediate Similarity	NPC46940
0.8077	Intermediate Similarity	NPC43525
0.8077	Intermediate Similarity	NPC471179
0.8068	Intermediate Similarity	NPC133050
0.8061	Intermediate Similarity	NPC130756
0.8061	Intermediate Similarity	NPC12931
0.8061	Intermediate Similarity	NPC213730
0.8061	Intermediate Similarity	NPC70677
0.8058	Intermediate Similarity	NPC44732
0.8058	Intermediate Similarity	NPC141782
0.8041	Intermediate Similarity	NPC474073
0.8041	Intermediate Similarity	NPC156313
0.8041	Intermediate Similarity	NPC32674
0.8041	Intermediate Similarity	NPC107619
0.8041	Intermediate Similarity	NPC109955
0.8039	Intermediate Similarity	NPC68260
0.8039	Intermediate Similarity	NPC279887
0.8021	Intermediate Similarity	NPC286006
0.8021	Intermediate Similarity	NPC107522
0.8021	Intermediate Similarity	NPC32714
0.802	Intermediate Similarity	NPC248904
0.8	Intermediate Similarity	NPC715
0.8	Intermediate Similarity	NPC263753
0.8	Intermediate Similarity	NPC35344
0.8	Intermediate Similarity	NPC218879
0.8	Intermediate Similarity	NPC117846
0.8	Intermediate Similarity	NPC120719
0.8	Intermediate Similarity	NPC475225
0.8	Intermediate Similarity	NPC244513
0.8	Intermediate Similarity	NPC475580
0.8	Intermediate Similarity	NPC141003
0.8	Intermediate Similarity	NPC242136
0.8	Intermediate Similarity	NPC227458
0.7981	Intermediate Similarity	NPC308689
0.798	Intermediate Similarity	NPC40258
0.798	Intermediate Similarity	NPC80800
0.798	Intermediate Similarity	NPC101025
0.798	Intermediate Similarity	NPC91461
0.798	Intermediate Similarity	NPC7686
0.798	Intermediate Similarity	NPC472585
0.798	Intermediate Similarity	NPC12221
0.798	Intermediate Similarity	NPC471578
0.7979	Intermediate Similarity	NPC312304
0.7979	Intermediate Similarity	NPC151764
0.7961	Intermediate Similarity	NPC282855
0.7961	Intermediate Similarity	NPC26013
0.7959	Intermediate Similarity	NPC171843
0.7959	Intermediate Similarity	NPC245561
0.7925	Intermediate Similarity	NPC195922
0.7925	Intermediate Similarity	NPC107240
0.7925	Intermediate Similarity	NPC12656

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 NPC70436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	1115
0.2-0.3	1696
0.3-0.4	2895
0.4-0.5	1796
0.5-0.6	938
0.6-0.7	291
0.7-0.8	45
0.8-0.85	6
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9438	High Similarity	NPD1809	Phase 2
0.9213	High Similarity	NPD845	Approved
0.8953	High Similarity	NPD111	Approved
0.8696	High Similarity	NPD1432	Clinical (unspecified phase)
0.8602	High Similarity	NPD844	Approved
0.8602	High Similarity	NPD2859	Approved
0.8602	High Similarity	NPD2860	Approved
0.8542	High Similarity	NPD940	Approved
0.8542	High Similarity	NPD846	Approved
0.8511	High Similarity	NPD288	Approved
0.8495	Intermediate Similarity	NPD2934	Approved
0.8495	Intermediate Similarity	NPD2933	Approved
0.8333	Intermediate Similarity	NPD3020	Approved
0.8247	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD2342	Discontinued
0.79	Intermediate Similarity	NPD9500	Approved
0.7822	Intermediate Similarity	NPD9608	Approved
0.7822	Intermediate Similarity	NPD9610	Approved
0.7736	Intermediate Similarity	NPD7635	Approved
0.77	Intermediate Similarity	NPD1242	Phase 1
0.7677	Intermediate Similarity	NPD9273	Approved
0.7674	Intermediate Similarity	NPD9087	Approved
0.7636	Intermediate Similarity	NPD5303	Approved
0.7636	Intermediate Similarity	NPD5304	Approved
0.7619	Intermediate Similarity	NPD4750	Phase 3
0.7619	Intermediate Similarity	NPD3021	Approved
0.7619	Intermediate Similarity	NPD3022	Approved
0.7614	Intermediate Similarity	NPD9294	Approved
0.7568	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4589	Approved
0.75	Intermediate Similarity	NPD1445	Approved
0.75	Intermediate Similarity	NPD1444	Approved
0.7434	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3143	Discontinued
0.7353	Intermediate Similarity	NPD3028	Approved
0.7339	Intermediate Similarity	NPD2229	Approved
0.7339	Intermediate Similarity	NPD2234	Approved
0.7339	Intermediate Similarity	NPD2228	Approved
0.7333	Intermediate Similarity	NPD9088	Approved
0.7321	Intermediate Similarity	NPD7330	Discontinued
0.7315	Intermediate Similarity	NPD228	Approved
0.7304	Intermediate Similarity	NPD3070	Discontinued
0.729	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1792	Phase 2
0.7264	Intermediate Similarity	NPD290	Approved
0.7241	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD255	Approved
0.7207	Intermediate Similarity	NPD6671	Approved
0.7207	Intermediate Similarity	NPD256	Approved
0.7196	Intermediate Similarity	NPD2684	Approved
0.7193	Intermediate Similarity	NPD4626	Approved
0.7172	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD968	Approved
0.7168	Intermediate Similarity	NPD3091	Approved
0.7143	Intermediate Similarity	NPD7636	Approved
0.7143	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1134	Approved
0.7119	Intermediate Similarity	NPD1133	Approved
0.7119	Intermediate Similarity	NPD1129	Approved
0.7119	Intermediate Similarity	NPD1131	Approved
0.7119	Intermediate Similarity	NPD1135	Approved
0.7117	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4093	Discontinued
0.7103	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9093	Approved
0.7091	Intermediate Similarity	NPD1138	Approved
0.7091	Intermediate Similarity	NPD9379	Approved
0.7091	Intermediate Similarity	NPD9377	Approved
0.7043	Intermediate Similarity	NPD4059	Approved
0.7043	Intermediate Similarity	NPD2286	Discontinued
0.7043	Intermediate Similarity	NPD2932	Approved
0.7043	Intermediate Similarity	NPD1751	Approved
0.7043	Intermediate Similarity	NPD3019	Approved
0.7037	Intermediate Similarity	NPD74	Approved
0.7037	Intermediate Similarity	NPD9266	Approved
0.7021	Intermediate Similarity	NPD9089	Approved
0.7018	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD1137	Approved
0.7	Intermediate Similarity	NPD1139	Approved
0.7	Intermediate Similarity	NPD4208	Discontinued
0.7	Intermediate Similarity	NPD4212	Discontinued
0.6991	Remote Similarity	NPD9493	Approved
0.6975	Remote Similarity	NPD1164	Approved
0.6964	Remote Similarity	NPD475	Phase 2
0.6964	Remote Similarity	NPD497	Approved
0.6964	Remote Similarity	NPD1791	Approved
0.6964	Remote Similarity	NPD1793	Approved
0.6944	Remote Similarity	NPD9264	Approved
0.6944	Remote Similarity	NPD9263	Approved
0.6944	Remote Similarity	NPD9267	Approved
0.6942	Remote Similarity	NPD4207	Discontinued
0.6937	Remote Similarity	NPD7843	Approved
0.6937	Remote Similarity	NPD821	Approved
0.693	Remote Similarity	NPD318	Approved
0.693	Remote Similarity	NPD16	Approved
0.693	Remote Similarity	NPD856	Approved
0.693	Remote Similarity	NPD317	Approved
0.6923	Remote Similarity	NPD3092	Approved
0.6923	Remote Similarity	NPD1610	Phase 2
0.6923	Remote Similarity	NPD422	Phase 1
0.6909	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD495	Approved
0.6875	Remote Similarity	NPD592	Approved
0.6875	Remote Similarity	NPD496	Approved
0.6875	Remote Similarity	NPD594	Approved
0.6875	Remote Similarity	NPD498	Approved
0.6875	Remote Similarity	NPD1398	Phase 1
0.687	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.687	Remote Similarity	NPD9545	Approved
0.6869	Remote Similarity	NPD9295	Approved
0.6842	Remote Similarity	NPD9568	Approved
0.6829	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9244	Approved
0.6818	Remote Similarity	NPD5451	Approved
0.6814	Remote Similarity	NPD9618	Approved
0.6814	Remote Similarity	NPD9614	Approved
0.681	Remote Similarity	NPD5691	Approved
0.6804	Remote Similarity	NPD9073	Approved
0.678	Remote Similarity	NPD1201	Approved
0.6777	Remote Similarity	NPD3691	Phase 2
0.6777	Remote Similarity	NPD3690	Phase 2
0.6754	Remote Similarity	NPD7157	Approved
0.6754	Remote Similarity	NPD6387	Discontinued
0.6752	Remote Similarity	NPD3095	Discontinued
0.675	Remote Similarity	NPD6696	Suspended
0.6724	Remote Similarity	NPD1759	Phase 1
0.672	Remote Similarity	NPD1555	Discontinued
0.672	Remote Similarity	NPD4060	Phase 1
0.6698	Remote Similarity	NPD1616	Discontinued
0.6697	Remote Similarity	NPD3134	Approved
0.6696	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7340	Approved
0.6694	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD4749	Approved
0.6667	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD4659	Approved
0.6667	Remote Similarity	NPD6583	Phase 3
0.6667	Remote Similarity	NPD9612	Approved
0.6667	Remote Similarity	NPD9611	Approved
0.6667	Remote Similarity	NPD9609	Approved
0.6667	Remote Similarity	NPD6582	Phase 2
0.664	Remote Similarity	NPD6405	Approved
0.664	Remote Similarity	NPD6407	Approved
0.6639	Remote Similarity	NPD2194	Approved
0.6639	Remote Similarity	NPD2195	Approved
0.6638	Remote Similarity	NPD1758	Phase 1
0.6638	Remote Similarity	NPD9613	Approved
0.6638	Remote Similarity	NPD9616	Approved
0.6638	Remote Similarity	NPD9615	Approved
0.6637	Remote Similarity	NPD5535	Approved
0.6636	Remote Similarity	NPD1358	Approved
0.6636	Remote Similarity	NPD4818	Approved
0.6636	Remote Similarity	NPD4817	Approved
0.6613	Remote Similarity	NPD4625	Phase 3
0.6612	Remote Similarity	NPD1283	Approved
0.661	Remote Similarity	NPD9381	Approved
0.661	Remote Similarity	NPD9384	Approved
0.661	Remote Similarity	NPD2667	Approved
0.661	Remote Similarity	NPD2668	Approved
0.6609	Remote Similarity	NPD709	Approved
0.6606	Remote Similarity	NPD9697	Approved
0.66	Remote Similarity	NPD9094	Approved
0.6585	Remote Similarity	NPD3636	Approved
0.6585	Remote Similarity	NPD3635	Approved
0.6585	Remote Similarity	NPD3637	Approved
0.6585	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2861	Phase 2
0.6585	Remote Similarity	NPD5736	Approved
0.6583	Remote Similarity	NPD2561	Approved
0.6583	Remote Similarity	NPD2562	Approved
0.6581	Remote Similarity	NPD316	Approved
0.6579	Remote Similarity	NPD5283	Phase 1
0.6574	Remote Similarity	NPD9261	Approved
0.6562	Remote Similarity	NPD3553	Approved
0.6562	Remote Similarity	NPD3555	Approved
0.6562	Remote Similarity	NPD3554	Approved
0.6562	Remote Similarity	NPD3552	Approved
0.6562	Remote Similarity	NPD9250	Approved
0.6557	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4103	Phase 2
0.6557	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD1470	Approved
0.6555	Remote Similarity	NPD3421	Phase 3
0.6555	Remote Similarity	NPD1981	Approved
0.6555	Remote Similarity	NPD3847	Discontinued
0.6555	Remote Similarity	NPD1983	Approved
0.6555	Remote Similarity	NPD1980	Approved
0.6538	Remote Similarity	NPD9296	Approved
0.6532	Remote Similarity	NPD2606	Approved
0.6532	Remote Similarity	NPD2605	Approved
0.6532	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD9622	Approved
0.6529	Remote Similarity	NPD1669	Approved
0.6525	Remote Similarity	NPD1651	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