NPASS Compound

Structure

NPC303950 OpenBabel07101719522D 25 27 0 0 1 0 0 0 0 0999 V2000 4.7469 -2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3457 -3.1315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2257 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5714 -0.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7524 -2.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1646 -1.4090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1701 -1.5135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 0.3136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 9 1 0 0 0 0 3 24 1 0 0 0 0 4 10 2 0 0 0 0 4 12 1 0 0 0 0 5 10 1 0 0 0 0 5 14 2 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 16 2 0 0 0 0 8 15 1 0 0 0 0 8 25 1 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 11 25 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 6 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.11
Volume:	343.16
LogP:	3.226
LogD:	2.677
LogS:	-4.515
# Rotatable Bonds:	5
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	3.246
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.984
MDCK Permeability:	1.1947005077672657e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.942
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.301
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	94.78926849365234%
Volume Distribution (VD):	1.006
Pgp-substrate:	3.4018614292144775%

ADMET: Metabolism

CYP1A2-inhibitor:	0.591
CYP1A2-substrate:	0.578
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.233
CYP2C9-substrate:	0.728
CYP2D6-inhibitor:	0.287
CYP2D6-substrate:	0.327
CYP3A4-inhibitor:	0.626
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	12.086
Half-life (T1/2):	0.215

ADMET: Toxicity

hERG Blockers:	0.303
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.763
AMES Toxicity:	0.664
Rat Oral Acute Toxicity:	0.378
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.078
Carcinogencity:	0.123
Eye Corrosion:	0.003
Eye Irritation:	0.478
Respiratory Toxicity:	0.728

Download Data

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

Natural Product: NPC303950

Natural Product ID:	NPC303950
*Common Name:**	Gramniphenol E
IUPAC Name:	2,4-dihydroxy-7-[(2S)-2-hydroxy-3-methylbut-3-enoxy]-5-methoxyfluoren-9-one
Synonyms:	Gramniphenol E
Standard InCHIKey:	FBNGGGIWMGUFMK-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C19H18O6/c1-9(2)15(22)8-25-11-6-13-18(16(7-11)24-3)17-12(19(13)23)4-10(20)5-14(17)21/h4-7,15,20-22H,1,8H2,2-3H3/t15-/m1/s1
SMILES:	C=C(C)[C@@H](COc1cc2c(-c3c(cc(cc3O)O)C2=O)c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333779
PubChem CID:	71578157
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO33109	arundina gramnifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23368966]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
Others	3

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	200.0	ug.mL-1	PMID[481436]
NPT27	Others	Unspecified		Ratio CC50/EC50	>	126.6	n.a.	PMID[481436]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	7.16	%	PMID[481436]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	1.58	ug.mL-1	PMID[481436]

☑ 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 NPC303950 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	381
0.1-0.2	1466
0.2-0.3	3312
0.3-0.4	8359
0.4-0.5	10384
0.5-0.6	3370
0.6-0.7	5099
0.7-0.8	6896
0.8-0.85	2856
0.85-0.9	564
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC96031
0.9247	High Similarity	NPC18714
0.9116	High Similarity	NPC103752
0.8954	High Similarity	NPC106372
0.8954	High Similarity	NPC58668
0.894	High Similarity	NPC17101
0.894	High Similarity	NPC77903
0.894	High Similarity	NPC14875
0.8917	High Similarity	NPC470810
0.8896	High Similarity	NPC207624
0.8896	High Similarity	NPC474843
0.8889	High Similarity	NPC225854
0.8882	High Similarity	NPC216624
0.8875	High Similarity	NPC53640
0.8861	High Similarity	NPC74854
0.8861	High Similarity	NPC45124
0.8861	High Similarity	NPC30655
0.8854	High Similarity	NPC329091
0.8831	High Similarity	NPC272566
0.8831	High Similarity	NPC472423
0.8831	High Similarity	NPC474744
0.8831	High Similarity	NPC115324
0.8831	High Similarity	NPC23668
0.8831	High Similarity	NPC193976
0.8831	High Similarity	NPC474772
0.8805	High Similarity	NPC472964
0.8797	High Similarity	NPC220582
0.8797	High Similarity	NPC304839
0.8797	High Similarity	NPC472902
0.8782	High Similarity	NPC148938
0.8782	High Similarity	NPC67396
0.8774	High Similarity	NPC180944
0.8774	High Similarity	NPC142308
0.8774	High Similarity	NPC470340
0.8766	High Similarity	NPC472421
0.875	High Similarity	NPC475985
0.875	High Similarity	NPC133065
0.8733	High Similarity	NPC49108
0.8726	High Similarity	NPC180924
0.8726	High Similarity	NPC208152
0.8726	High Similarity	NPC24640
0.8726	High Similarity	NPC164427
0.8726	High Similarity	NPC78492
0.8718	High Similarity	NPC287504
0.8718	High Similarity	NPC235333
0.8718	High Similarity	NPC25127
0.8718	High Similarity	NPC469405
0.871	High Similarity	NPC151425
0.871	High Similarity	NPC263384
0.871	High Similarity	NPC471676
0.871	High Similarity	NPC200773
0.871	High Similarity	NPC472422
0.871	High Similarity	NPC471229
0.871	High Similarity	NPC244577
0.871	High Similarity	NPC72958
0.871	High Similarity	NPC70016
0.871	High Similarity	NPC240768
0.871	High Similarity	NPC232645
0.871	High Similarity	NPC215921
0.871	High Similarity	NPC472420
0.8696	High Similarity	NPC39306
0.8696	High Similarity	NPC326520
0.8693	High Similarity	NPC17816
0.8693	High Similarity	NPC81835
0.8693	High Similarity	NPC21835
0.8688	High Similarity	NPC211107
0.8688	High Similarity	NPC472402
0.8679	High Similarity	NPC321399
0.8679	High Similarity	NPC471976
0.8679	High Similarity	NPC36217
0.8679	High Similarity	NPC24627
0.8675	High Similarity	NPC310340
0.8675	High Similarity	NPC73028
0.8671	High Similarity	NPC241904
0.8671	High Similarity	NPC477833
0.8671	High Similarity	NPC96342
0.8671	High Similarity	NPC300727
0.8671	High Similarity	NPC164110
0.8671	High Similarity	NPC129684
0.8671	High Similarity	NPC246647
0.8671	High Similarity	NPC212967
0.8671	High Similarity	NPC299520
0.8662	High Similarity	NPC175192
0.8662	High Similarity	NPC297531
0.8662	High Similarity	NPC213936
0.8662	High Similarity	NPC255807
0.8662	High Similarity	NPC99199
0.8662	High Similarity	NPC31018
0.8654	High Similarity	NPC473996
0.8654	High Similarity	NPC171651
0.8654	High Similarity	NPC40356
0.8654	High Similarity	NPC327269
0.8654	High Similarity	NPC31627
0.8654	High Similarity	NPC268992
0.8654	High Similarity	NPC476238
0.8654	High Similarity	NPC87708
0.8654	High Similarity	NPC28103
0.8654	High Similarity	NPC154683
0.8654	High Similarity	NPC51824
0.8654	High Similarity	NPC243171
0.8654	High Similarity	NPC113608
0.8654	High Similarity	NPC470337
0.8654	High Similarity	NPC285623
0.8654	High Similarity	NPC35567
0.8654	High Similarity	NPC470338
0.8645	High Similarity	NPC202595
0.8645	High Similarity	NPC267117
0.8645	High Similarity	NPC338131
0.8645	High Similarity	NPC13282
0.8642	High Similarity	NPC170245
0.8642	High Similarity	NPC178851
0.8642	High Similarity	NPC477517
0.8636	High Similarity	NPC218569
0.8634	High Similarity	NPC474240
0.8634	High Similarity	NPC7483
0.8634	High Similarity	NPC124038
0.8634	High Similarity	NPC18100
0.8634	High Similarity	NPC197168
0.8627	High Similarity	NPC290133
0.8627	High Similarity	NPC316769
0.8627	High Similarity	NPC24136
0.8627	High Similarity	NPC187282
0.8627	High Similarity	NPC299011
0.8625	High Similarity	NPC3629
0.8625	High Similarity	NPC474186
0.8625	High Similarity	NPC269117
0.8618	High Similarity	NPC207732
0.8616	High Similarity	NPC85121
0.8616	High Similarity	NPC476242
0.8616	High Similarity	NPC210459
0.8616	High Similarity	NPC470339
0.8608	High Similarity	NPC274730
0.8608	High Similarity	NPC469474
0.8606	High Similarity	NPC98776
0.8599	High Similarity	NPC203080
0.8599	High Similarity	NPC472583
0.8599	High Similarity	NPC18727
0.8599	High Similarity	NPC223701
0.8599	High Similarity	NPC7989
0.8599	High Similarity	NPC293286
0.8599	High Similarity	NPC280937
0.8599	High Similarity	NPC183874
0.8599	High Similarity	NPC89474
0.8599	High Similarity	NPC155686
0.8598	High Similarity	NPC315306
0.8598	High Similarity	NPC313717
0.859	High Similarity	NPC474021
0.859	High Similarity	NPC471675
0.859	High Similarity	NPC132990
0.859	High Similarity	NPC470569
0.859	High Similarity	NPC278476
0.859	High Similarity	NPC262039
0.859	High Similarity	NPC472580
0.859	High Similarity	NPC170169
0.859	High Similarity	NPC319910
0.859	High Similarity	NPC472636
0.859	High Similarity	NPC46882
0.859	High Similarity	NPC262038
0.859	High Similarity	NPC254412
0.859	High Similarity	NPC149526
0.859	High Similarity	NPC471677
0.859	High Similarity	NPC75695
0.859	High Similarity	NPC474023
0.859	High Similarity	NPC474417
0.859	High Similarity	NPC78505
0.8589	High Similarity	NPC247973
0.8589	High Similarity	NPC6588
0.8589	High Similarity	NPC117854
0.8589	High Similarity	NPC477154
0.8581	High Similarity	NPC317492
0.8581	High Similarity	NPC65775
0.8581	High Similarity	NPC100985
0.8581	High Similarity	NPC97028
0.8581	High Similarity	NPC277032
0.8581	High Similarity	NPC89442
0.8581	High Similarity	NPC288036
0.8581	High Similarity	NPC473091
0.8581	High Similarity	NPC178202
0.8581	High Similarity	NPC10027
0.8581	High Similarity	NPC65589
0.8581	High Similarity	NPC158338
0.8581	High Similarity	NPC97029
0.858	High Similarity	NPC475888
0.858	High Similarity	NPC472277
0.858	High Similarity	NPC474591
0.858	High Similarity	NPC473286
0.858	High Similarity	NPC25361
0.8571	High Similarity	NPC476182
0.8571	High Similarity	NPC84515
0.8571	High Similarity	NPC44721
0.8571	High Similarity	NPC312056
0.8571	High Similarity	NPC211466
0.8571	High Similarity	NPC259632
0.8571	High Similarity	NPC81679
0.8571	High Similarity	NPC40086
0.8571	High Similarity	NPC201800
0.8571	High Similarity	NPC176869
0.8571	High Similarity	NPC122828
0.8571	High Similarity	NPC470670
0.8571	High Similarity	NPC202494

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 NPC303950 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	898
0.2-0.3	1692
0.3-0.4	2582
0.4-0.5	1867
0.5-0.6	1057
0.6-0.7	516
0.7-0.8	160
0.8-0.85	36
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8535	High Similarity	NPD1934	Approved
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8491	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD4380	Phase 2
0.8365	Intermediate Similarity	NPD2801	Approved
0.8364	Intermediate Similarity	NPD3818	Discontinued
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5844	Phase 1
0.8289	Intermediate Similarity	NPD1549	Phase 2
0.8282	Intermediate Similarity	NPD6959	Discontinued
0.825	Intermediate Similarity	NPD1465	Phase 2
0.825	Intermediate Similarity	NPD7819	Suspended
0.8242	Intermediate Similarity	NPD6166	Phase 2
0.8242	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7075	Discontinued
0.8205	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD4628	Phase 3
0.8158	Intermediate Similarity	NPD2796	Approved
0.8141	Intermediate Similarity	NPD1511	Approved
0.8141	Intermediate Similarity	NPD6799	Approved
0.8137	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5494	Approved
0.8107	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1510	Phase 2
0.8089	Intermediate Similarity	NPD2532	Approved
0.8089	Intermediate Similarity	NPD2533	Approved
0.8089	Intermediate Similarity	NPD2534	Approved
0.8075	Intermediate Similarity	NPD6801	Discontinued
0.8067	Intermediate Similarity	NPD1240	Approved
0.8063	Intermediate Similarity	NPD6599	Discontinued
0.8061	Intermediate Similarity	NPD7199	Phase 2
0.8059	Intermediate Similarity	NPD6559	Discontinued
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7074	Phase 3
0.8038	Intermediate Similarity	NPD1512	Approved
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD3749	Approved
0.7988	Intermediate Similarity	NPD7054	Approved
0.7976	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5402	Approved
0.7975	Intermediate Similarity	NPD3817	Phase 2
0.7961	Intermediate Similarity	NPD1607	Approved
0.7941	Intermediate Similarity	NPD7472	Approved
0.7895	Intermediate Similarity	NPD6797	Phase 2
0.7885	Intermediate Similarity	NPD2800	Approved
0.7882	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3748	Approved
0.7849	Intermediate Similarity	NPD7251	Discontinued
0.7824	Intermediate Similarity	NPD3751	Discontinued
0.7815	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6100	Approved
0.7806	Intermediate Similarity	NPD6099	Approved
0.7803	Intermediate Similarity	NPD7808	Phase 3
0.7803	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7771	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5403	Approved
0.7756	Intermediate Similarity	NPD2344	Approved
0.7751	Intermediate Similarity	NPD3926	Phase 2
0.775	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD37	Approved
0.7725	Intermediate Similarity	NPD6234	Discontinued
0.7712	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1613	Approved
0.7711	Intermediate Similarity	NPD7768	Phase 2
0.7711	Intermediate Similarity	NPD4966	Approved
0.7711	Intermediate Similarity	NPD4965	Approved
0.7711	Intermediate Similarity	NPD4967	Phase 2
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3787	Discontinued
0.7654	Intermediate Similarity	NPD920	Approved
0.764	Intermediate Similarity	NPD5401	Approved
0.7633	Intermediate Similarity	NPD1247	Approved
0.7632	Intermediate Similarity	NPD3027	Phase 3
0.7628	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD943	Approved
0.7593	Intermediate Similarity	NPD6273	Approved
0.7588	Intermediate Similarity	NPD7229	Phase 3
0.758	Intermediate Similarity	NPD1551	Phase 2
0.758	Intermediate Similarity	NPD2935	Discontinued
0.7562	Intermediate Similarity	NPD2309	Approved
0.7561	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3226	Approved
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6355	Discontinued
0.7547	Intermediate Similarity	NPD1243	Approved
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7685	Pre-registration
0.7533	Intermediate Similarity	NPD1876	Approved
0.7531	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD919	Approved
0.7514	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD5761	Phase 2
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD5760	Phase 2
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7390	Discontinued
0.7458	Intermediate Similarity	NPD8313	Approved
0.7458	Intermediate Similarity	NPD8312	Approved
0.7451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4908	Phase 1
0.7443	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7421	Intermediate Similarity	NPD5762	Approved
0.7421	Intermediate Similarity	NPD5763	Approved
0.7421	Intermediate Similarity	NPD2346	Discontinued
0.7407	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2799	Discontinued
0.7405	Intermediate Similarity	NPD7033	Discontinued
0.7405	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4625	Phase 3
0.7401	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5953	Discontinued
0.7375	Intermediate Similarity	NPD2424	Discontinued
0.7372	Intermediate Similarity	NPD4060	Phase 1
0.7371	Intermediate Similarity	NPD7286	Phase 2
0.7355	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3764	Approved
0.7349	Intermediate Similarity	NPD2649	Approved
0.7349	Intermediate Similarity	NPD2651	Approved
0.7348	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6190	Approved
0.7333	Intermediate Similarity	NPD1610	Phase 2
0.733	Intermediate Similarity	NPD8151	Discontinued
0.7326	Intermediate Similarity	NPD8127	Discontinued
0.7312	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1608	Approved
0.7284	Intermediate Similarity	NPD3892	Phase 2
0.7278	Intermediate Similarity	NPD6651	Approved
0.7273	Intermediate Similarity	NPD6778	Approved
0.7273	Intermediate Similarity	NPD6779	Approved
0.7273	Intermediate Similarity	NPD6776	Approved
0.7273	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6780	Approved
0.7273	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD6781	Approved
0.7273	Intermediate Similarity	NPD6777	Approved
0.7273	Intermediate Similarity	NPD9494	Approved
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.7244	Intermediate Similarity	NPD3268	Approved
0.7241	Intermediate Similarity	NPD5242	Approved
0.7235	Intermediate Similarity	NPD4288	Approved
0.7222	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD447	Suspended
0.7205	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6005	Phase 3
0.7205	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6002	Phase 3
0.7205	Intermediate Similarity	NPD6004	Phase 3
0.7186	Intermediate Similarity	NPD1653	Approved
0.7181	Intermediate Similarity	NPD1548	Phase 1
0.7176	Intermediate Similarity	NPD8455	Phase 2
0.7171	Intermediate Similarity	NPD3972	Approved
0.717	Intermediate Similarity	NPD6653	Approved
0.716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD1203	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7135	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7134	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4749	Approved
0.7124	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7177	Discontinued
0.7117	Intermediate Similarity	NPD1652	Phase 2
0.7115	Intermediate Similarity	NPD6832	Phase 2
0.7112	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD422	Phase 1
0.7102	Intermediate Similarity	NPD2403	Approved
0.7099	Intermediate Similarity	NPD1471	Phase 3
0.7097	Intermediate Similarity	NPD4360	Phase 2
0.7097	Intermediate Similarity	NPD4363	Phase 3
0.7097	Intermediate Similarity	NPD5647	Approved
0.7089	Intermediate Similarity	NPD6233	Phase 2
0.7086	Intermediate Similarity	NPD17	Approved
0.7081	Intermediate Similarity	NPD4308	Phase 3
0.7077	Intermediate Similarity	NPD7783	Phase 2
0.7077	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7003	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