NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	465.09
Volume:	427.478
LogP:	2.971
LogD:	1.249
LogS:	-3.865
# Rotatable Bonds:	10
TPSA:	191.96
# H-Bond Aceptor:	13
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	3.32
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.28
MDCK Permeability:	4.017180981463753e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.479
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.651

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	94.31488037109375%
Volume Distribution (VD):	0.287
Pgp-substrate:	6.165401458740234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.54
CYP1A2-substrate:	0.663
CYP2C19-inhibitor:	0.142
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.736
CYP2C9-substrate:	0.805
CYP2D6-inhibitor:	0.277
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.183
CYP3A4-substrate:	0.083

ADMET: Excretion

Clearance (CL):	5.198
Half-life (T1/2):	0.917

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.439
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.15
Skin Sensitization:	0.698
Carcinogencity:	0.02
Eye Corrosion:	0.008
Eye Irritation:	0.695
Respiratory Toxicity:	0.235

Download Data

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

Natural Product: NPC477828

Natural Product ID:	NPC477828
*Common Name:**	Pseudogymnoascin C
IUPAC Name:	2-[2-hydroxy-6-(4-hydroxy-6-methoxy-2-methoxycarbonyl-3-nitrophenoxy)-4-methylbenzoyl]oxypropanoic acid
Synonyms:
Standard InCHIKey:	OCYICDINBUIUEQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19NO12/c1-8-5-10(22)14(20(27)32-9(2)18(24)25)12(6-8)33-17-13(30-3)7-11(23)16(21(28)29)15(17)19(26)31-4/h5-7,9,22-23H,1-4H3,(H,24,25)
SMILES:	CC1=CC(=C(C(=C1)OC2=C(C=C(C(=C2C(=O)OC)[N+](=O)[O-])O)OC)C(=O)OC(C)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122177639
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO33556	Pseudogymnoascus sp.	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25732560]

☑ 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	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	MIC95	=	64	ug/ml	PMID[25732560]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC95	=	64	ug/ml	PMID[25732560]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC95	=	64	ug/ml	PMID[25732560]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC95	=	64	ug/ml	PMID[25732560]
NPT20	Organism	Candida albicans	Candida albicans	MIC95	=	64	ug/ml	PMID[25732560]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC95	=	64	ug/ml	PMID[25732560]

☑ 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 NPC477828 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	410
0.1-0.2	2354
0.2-0.3	8679
0.3-0.4	10062
0.4-0.5	6077
0.5-0.6	10799
0.6-0.7	4300
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9689	High Similarity	NPC477826
0.9689	High Similarity	NPC477827
0.9635	High Similarity	NPC477825
0.7717	Intermediate Similarity	NPC76478
0.7557	Intermediate Similarity	NPC118189
0.7523	Intermediate Similarity	NPC148391
0.7512	Intermediate Similarity	NPC98416
0.75	Intermediate Similarity	NPC182853
0.7467	Intermediate Similarity	NPC13249
0.7445	Intermediate Similarity	NPC227033
0.7443	Intermediate Similarity	NPC2905
0.7421	Intermediate Similarity	NPC134702
0.7399	Intermediate Similarity	NPC7560
0.7397	Intermediate Similarity	NPC114468
0.7358	Intermediate Similarity	NPC164527
0.7358	Intermediate Similarity	NPC213382
0.733	Intermediate Similarity	NPC240684
0.7318	Intermediate Similarity	NPC268223
0.7306	Intermediate Similarity	NPC106334
0.7306	Intermediate Similarity	NPC295479
0.7306	Intermediate Similarity	NPC285527
0.7306	Intermediate Similarity	NPC220241
0.7285	Intermediate Similarity	NPC290227
0.7269	Intermediate Similarity	NPC285254
0.7268	Intermediate Similarity	NPC225129
0.7124	Intermediate Similarity	NPC157983
0.7124	Intermediate Similarity	NPC118154
0.7123	Intermediate Similarity	NPC212123
0.7117	Intermediate Similarity	NPC305542
0.7085	Intermediate Similarity	NPC30749
0.7072	Intermediate Similarity	NPC218303
0.7054	Intermediate Similarity	NPC176113
0.704	Intermediate Similarity	NPC116178
0.704	Intermediate Similarity	NPC91234
0.7035	Intermediate Similarity	NPC195120
0.7035	Intermediate Similarity	NPC87560
0.703	Intermediate Similarity	NPC217950
0.7027	Intermediate Similarity	NPC474366
0.702	Intermediate Similarity	NPC289968
0.7015	Intermediate Similarity	NPC287458
0.7009	Intermediate Similarity	NPC217903
0.6987	Remote Similarity	NPC251071
0.6982	Remote Similarity	NPC85661
0.6982	Remote Similarity	NPC121510
0.6982	Remote Similarity	NPC171882
0.698	Remote Similarity	NPC130955
0.698	Remote Similarity	NPC98892
0.6965	Remote Similarity	NPC472438
0.6965	Remote Similarity	NPC7973
0.6965	Remote Similarity	NPC78302
0.6965	Remote Similarity	NPC235215
0.6965	Remote Similarity	NPC29841
0.6957	Remote Similarity	NPC72696
0.6946	Remote Similarity	NPC112418
0.6938	Remote Similarity	NPC264735
0.6937	Remote Similarity	NPC46679
0.6933	Remote Similarity	NPC227361
0.6933	Remote Similarity	NPC124658
0.6933	Remote Similarity	NPC321166
0.6931	Remote Similarity	NPC19687
0.6931	Remote Similarity	NPC115798
0.6931	Remote Similarity	NPC18772
0.6931	Remote Similarity	NPC22472
0.6931	Remote Similarity	NPC18607
0.6931	Remote Similarity	NPC9609
0.6931	Remote Similarity	NPC152166
0.6931	Remote Similarity	NPC25495
0.6931	Remote Similarity	NPC300943
0.6931	Remote Similarity	NPC288669
0.6931	Remote Similarity	NPC7846
0.6931	Remote Similarity	NPC191459
0.6931	Remote Similarity	NPC176300
0.6931	Remote Similarity	NPC253634
0.6931	Remote Similarity	NPC130894
0.6931	Remote Similarity	NPC105242
0.6931	Remote Similarity	NPC143828
0.6931	Remote Similarity	NPC204854
0.6931	Remote Similarity	NPC261004
0.6931	Remote Similarity	NPC4481
0.6927	Remote Similarity	NPC470457
0.692	Remote Similarity	NPC61731
0.692	Remote Similarity	NPC186569
0.6915	Remote Similarity	NPC268161
0.6915	Remote Similarity	NPC55619
0.6915	Remote Similarity	NPC178854
0.6915	Remote Similarity	NPC100916
0.6915	Remote Similarity	NPC200388
0.6915	Remote Similarity	NPC474520
0.6914	Remote Similarity	NPC317567
0.6912	Remote Similarity	NPC471745
0.6908	Remote Similarity	NPC9475
0.6908	Remote Similarity	NPC280493
0.6905	Remote Similarity	NPC198324
0.6905	Remote Similarity	NPC472380
0.6905	Remote Similarity	NPC472385
0.6905	Remote Similarity	NPC472384
0.6905	Remote Similarity	NPC472382
0.69	Remote Similarity	NPC246204
0.6897	Remote Similarity	NPC471744
0.6892	Remote Similarity	NPC198160
0.6881	Remote Similarity	NPC93376
0.6881	Remote Similarity	NPC305663
0.6881	Remote Similarity	NPC189179
0.6881	Remote Similarity	NPC224137
0.6881	Remote Similarity	NPC176665
0.6881	Remote Similarity	NPC163524
0.6881	Remote Similarity	NPC75215
0.6881	Remote Similarity	NPC227192
0.6881	Remote Similarity	NPC203891
0.6881	Remote Similarity	NPC101830
0.6881	Remote Similarity	NPC287979
0.6881	Remote Similarity	NPC110070
0.6878	Remote Similarity	NPC470459
0.6866	Remote Similarity	NPC189960
0.6866	Remote Similarity	NPC32557
0.686	Remote Similarity	NPC158761
0.686	Remote Similarity	NPC470456
0.6857	Remote Similarity	NPC115760
0.6857	Remote Similarity	NPC210094
0.6857	Remote Similarity	NPC135277
0.6857	Remote Similarity	NPC101191
0.6857	Remote Similarity	NPC237435
0.6857	Remote Similarity	NPC477848
0.6857	Remote Similarity	NPC49344
0.6857	Remote Similarity	NPC43211
0.685	Remote Similarity	NPC75069
0.685	Remote Similarity	NPC199773
0.6847	Remote Similarity	NPC193842
0.6847	Remote Similarity	NPC195832
0.6847	Remote Similarity	NPC152904
0.6842	Remote Similarity	NPC476370
0.6832	Remote Similarity	NPC245546
0.6832	Remote Similarity	NPC292107
0.6832	Remote Similarity	NPC98661
0.6832	Remote Similarity	NPC54928
0.6832	Remote Similarity	NPC43243
0.6832	Remote Similarity	NPC49824
0.6832	Remote Similarity	NPC266960
0.6832	Remote Similarity	NPC247017
0.6827	Remote Similarity	NPC476279
0.6825	Remote Similarity	NPC211532
0.6825	Remote Similarity	NPC233994
0.6825	Remote Similarity	NPC268533
0.6816	Remote Similarity	NPC299435
0.6816	Remote Similarity	NPC75279
0.6816	Remote Similarity	NPC260604
0.6816	Remote Similarity	NPC298802
0.6816	Remote Similarity	NPC250822
0.6816	Remote Similarity	NPC58382
0.6816	Remote Similarity	NPC86485
0.6816	Remote Similarity	NPC276409
0.6816	Remote Similarity	NPC162351
0.6814	Remote Similarity	NPC246478
0.6814	Remote Similarity	NPC263449
0.6812	Remote Similarity	NPC470462
0.6812	Remote Similarity	NPC20216
0.681	Remote Similarity	NPC169977
0.681	Remote Similarity	NPC476374
0.681	Remote Similarity	NPC42773
0.681	Remote Similarity	NPC24043
0.681	Remote Similarity	NPC101026
0.681	Remote Similarity	NPC21666
0.681	Remote Similarity	NPC4390
0.681	Remote Similarity	NPC45522
0.6802	Remote Similarity	NPC38961
0.68	Remote Similarity	NPC76376
0.6798	Remote Similarity	NPC162869
0.6798	Remote Similarity	NPC471479
0.6798	Remote Similarity	NPC470402
0.6798	Remote Similarity	NPC474836
0.6798	Remote Similarity	NPC48208
0.6798	Remote Similarity	NPC156057
0.6798	Remote Similarity	NPC471515
0.6798	Remote Similarity	NPC475267
0.6798	Remote Similarity	NPC474208
0.6797	Remote Similarity	NPC329830
0.6796	Remote Similarity	NPC41301
0.6796	Remote Similarity	NPC156082
0.6794	Remote Similarity	NPC109827
0.6794	Remote Similarity	NPC17219
0.6794	Remote Similarity	NPC124470
0.6794	Remote Similarity	NPC246716
0.6783	Remote Similarity	NPC256422
0.6782	Remote Similarity	NPC280339
0.6782	Remote Similarity	NPC276059
0.6782	Remote Similarity	NPC214138
0.6782	Remote Similarity	NPC286052
0.6782	Remote Similarity	NPC2476
0.6782	Remote Similarity	NPC163780
0.6782	Remote Similarity	NPC37392
0.6782	Remote Similarity	NPC167815
0.6782	Remote Similarity	NPC34725
0.6782	Remote Similarity	NPC227325
0.6782	Remote Similarity	NPC213622
0.6782	Remote Similarity	NPC208197
0.6782	Remote Similarity	NPC201136
0.6782	Remote Similarity	NPC183597
0.6782	Remote Similarity	NPC476642
0.6782	Remote Similarity	NPC44079
0.6782	Remote Similarity	NPC92659

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 NPC477828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	843
0.2-0.3	1849
0.3-0.4	2530
0.4-0.5	2340
0.5-0.6	1113
0.6-0.7	185
0.7-0.8	3
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
0.7626	Intermediate Similarity	NPD2899	Discontinued
0.7445	Intermediate Similarity	NPD8067	Phase 3
0.7202	Intermediate Similarity	NPD6296	Discontinued
0.7155	Intermediate Similarity	NPD6625	Approved
0.6914	Remote Similarity	NPD8367	Approved
0.6908	Remote Similarity	NPD1221	Approved
0.6866	Remote Similarity	NPD3817	Phase 2
0.6866	Remote Similarity	NPD5402	Approved
0.6863	Remote Similarity	NPD2821	Approved
0.6857	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8492	Approved
0.6763	Remote Similarity	NPD1220	Phase 1
0.6749	Remote Similarity	NPD3882	Suspended
0.6733	Remote Similarity	NPD2801	Approved
0.6728	Remote Similarity	NPD7125	Discontinued
0.6716	Remote Similarity	NPD955	Approved
0.6667	Remote Similarity	NPD7476	Discontinued
0.6634	Remote Similarity	NPD2672	Discontinued
0.6634	Remote Similarity	NPD2366	Approved
0.6626	Remote Similarity	NPD1852	Discontinued
0.6603	Remote Similarity	NPD6166	Phase 2
0.6603	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1934	Approved
0.6585	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6874	Approved
0.6574	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7075	Discontinued
0.6547	Remote Similarity	NPD2339	Phase 3
0.6544	Remote Similarity	NPD1898	Discontinued
0.6542	Remote Similarity	NPD7808	Phase 3
0.6526	Remote Similarity	NPD6184	Discontinued
0.6526	Remote Similarity	NPD6797	Phase 2
0.6517	Remote Similarity	NPD5403	Approved
0.6515	Remote Similarity	NPD6723	Discontinued
0.6507	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6232	Discontinued
0.6502	Remote Similarity	NPD3684	Discontinued
0.6495	Remote Similarity	NPD6104	Discontinued
0.6495	Remote Similarity	NPD7251	Discontinued
0.649	Remote Similarity	NPD3251	Approved
0.6489	Remote Similarity	NPD5006	Approved
0.6489	Remote Similarity	NPD5005	Approved
0.6489	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD8461	Discontinued
0.6481	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5242	Approved
0.6471	Remote Similarity	NPD7256	Discontinued
0.6465	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3818	Discontinued
0.645	Remote Similarity	NPD6799	Approved
0.6436	Remote Similarity	NPD711	Discontinued
0.6432	Remote Similarity	NPD7054	Approved
0.6432	Remote Similarity	NPD5844	Phase 1
0.6432	Remote Similarity	NPD7891	Discontinued
0.6429	Remote Similarity	NPD1551	Phase 2
0.6422	Remote Similarity	NPD6599	Discontinued
0.6418	Remote Similarity	NPD5401	Approved
0.6415	Remote Similarity	NPD7473	Discontinued
0.6413	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7074	Phase 3
0.6402	Remote Similarity	NPD7472	Approved
0.64	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD3453	Discontinued
0.6386	Remote Similarity	NPD1512	Approved
0.6372	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2246	Approved
0.6368	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2248	Approved
0.6364	Remote Similarity	NPD3252	Approved
0.636	Remote Similarity	NPD3298	Approved
0.6359	Remote Similarity	NPD7546	Discontinued
0.6359	Remote Similarity	NPD6801	Discontinued
0.6343	Remote Similarity	NPD7038	Approved
0.6343	Remote Similarity	NPD7039	Approved
0.6336	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7783	Phase 2
0.633	Remote Similarity	NPD6045	Phase 3
0.6327	Remote Similarity	NPD6779	Approved
0.6327	Remote Similarity	NPD6777	Approved
0.6327	Remote Similarity	NPD6776	Approved
0.6327	Remote Similarity	NPD6781	Approved
0.6327	Remote Similarity	NPD6780	Approved
0.6327	Remote Similarity	NPD6782	Approved
0.6327	Remote Similarity	NPD6778	Approved
0.6316	Remote Similarity	NPD7435	Discontinued
0.6311	Remote Similarity	NPD4420	Approved
0.6311	Remote Similarity	NPD4668	Phase 2
0.6308	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD447	Suspended
0.6307	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7584	Approved
0.6303	Remote Similarity	NPD7907	Approved
0.6295	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7874	Approved
0.6293	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD3925	Approved
0.629	Remote Similarity	NPD2845	Phase 2
0.629	Remote Similarity	NPD2843	Phase 2
0.6287	Remote Similarity	NPD1511	Approved
0.6284	Remote Similarity	NPD9468	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD8404	Phase 2
0.6267	Remote Similarity	NPD6559	Discontinued
0.6266	Remote Similarity	NPD1945	Phase 1
0.6262	Remote Similarity	NPD3296	Phase 1
0.6256	Remote Similarity	NPD5494	Approved
0.6245	Remote Similarity	NPD6198	Phase 1
0.6245	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD7263	Phase 2
0.6233	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD2681	Approved
0.6226	Remote Similarity	NPD2680	Approved
0.6211	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7585	Approved
0.6205	Remote Similarity	NPD6213	Phase 3
0.6205	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD6212	Phase 3
0.6204	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.62	Remote Similarity	NPD1483	Discontinued
0.6197	Remote Similarity	NPD683	Approved
0.6195	Remote Similarity	NPD4604	Approved
0.6195	Remote Similarity	NPD4605	Approved
0.6186	Remote Similarity	NPD7559	Phase 2
0.6184	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD3912	Discontinued
0.6176	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7698	Approved
0.6174	Remote Similarity	NPD7697	Approved
0.6174	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7696	Phase 3
0.6172	Remote Similarity	NPD1465	Phase 2
0.6171	Remote Similarity	NPD2792	Approved
0.6169	Remote Similarity	NPD4846	Phase 2
0.6164	Remote Similarity	NPD7583	Approved
0.6161	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD2494	Approved
0.6157	Remote Similarity	NPD2493	Approved
0.6157	Remote Similarity	NPD3452	Approved
0.6157	Remote Similarity	NPD3450	Approved
0.6154	Remote Similarity	NPD6386	Approved
0.6154	Remote Similarity	NPD3154	Approved
0.6154	Remote Similarity	NPD3153	Approved
0.6154	Remote Similarity	NPD5914	Approved
0.6154	Remote Similarity	NPD6385	Approved
0.6151	Remote Similarity	NPD5519	Discontinued
0.615	Remote Similarity	NPD1247	Approved
0.6147	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7871	Phase 2
0.6147	Remote Similarity	NPD7870	Phase 2
0.6147	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD5353	Approved
0.6141	Remote Similarity	NPD4049	Phase 2
0.614	Remote Similarity	NPD3297	Approved
0.6139	Remote Similarity	NPD1196	Approved
0.6137	Remote Similarity	NPD7701	Phase 2
0.6135	Remote Similarity	NPD3455	Phase 2
0.6132	Remote Similarity	NPD6234	Discontinued
0.6132	Remote Similarity	NPD919	Approved
0.613	Remote Similarity	NPD6823	Phase 2
0.6126	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD8150	Discontinued
0.6125	Remote Similarity	NPD3437	Discontinued
0.6123	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD6190	Approved
0.6106	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6534	Approved
0.6106	Remote Similarity	NPD6535	Approved
0.6106	Remote Similarity	NPD4380	Phase 2
0.61	Remote Similarity	NPD2935	Discontinued
0.6099	Remote Similarity	NPD3398	Discontinued
0.6098	Remote Similarity	NPD2532	Approved
0.6098	Remote Similarity	NPD2534	Approved
0.6098	Remote Similarity	NPD2533	Approved
0.6095	Remote Similarity	NPD7819	Suspended
0.6091	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD1195	Approved
0.6087	Remote Similarity	NPD1653	Approved
0.6083	Remote Similarity	NPD4111	Phase 1
0.6083	Remote Similarity	NPD4665	Approved
0.6078	Remote Similarity	NPD4583	Approved
0.6078	Remote Similarity	NPD4582	Approved
0.6075	Remote Similarity	NPD6959	Discontinued
0.6068	Remote Similarity	NPD2906	Approved
0.6068	Remote Similarity	NPD2907	Approved
0.6068	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD230	Phase 1
0.6059	Remote Similarity	NPD7801	Approved
0.6053	Remote Similarity	NPD2974	Approved
0.6053	Remote Similarity	NPD2975	Approved
0.6053	Remote Similarity	NPD2973	Approved
0.6049	Remote Similarity	NPD1543	Discontinued
0.6048	Remote Similarity	NPD37	Approved
0.6048	Remote Similarity	NPD6844	Discontinued
0.6047	Remote Similarity	NPD4606	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