NPASS Compound

Structure

CID116178 OpenBabel06191715472D 26 29 0 0 1 0 0 0 0 0999 V2000 -4.3005 2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 4.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 1.9487 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3005 1.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 3.6808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 13 2 0 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.14
Volume:	356.743
LogP:	2.596
LogD:	2.337
LogS:	-4.242
# Rotatable Bonds:	3
TPSA:	80.92
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	3.696
Fsp3:	0.35
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:	-4.866
MDCK Permeability:	1.0557068890193477e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.079
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.143

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.725
Plasma Protein Binding (PPB):	93.67112731933594%
Volume Distribution (VD):	0.625
Pgp-substrate:	3.9701626300811768%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.228
CYP2C19-substrate:	0.55
CYP2C9-inhibitor:	0.547
CYP2C9-substrate:	0.763
CYP2D6-inhibitor:	0.552
CYP2D6-substrate:	0.489
CYP3A4-inhibitor:	0.19
CYP3A4-substrate:	0.391

ADMET: Excretion

Clearance (CL):	4.528
Half-life (T1/2):	0.232

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.13
AMES Toxicity:	0.82
Rat Oral Acute Toxicity:	0.433
Maximum Recommended Daily Dose:	0.773
Skin Sensitization:	0.545
Carcinogencity:	0.926
Eye Corrosion:	0.003
Eye Irritation:	0.374
Respiratory Toxicity:	0.248

Download Data

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

Natural Product: NPC116178

Natural Product ID:	NPC116178
*Common Name:**	Gravacridondiolmonomethyl Ether
IUPAC Name:	5-hydroxy-2-(2-hydroxy-1-methoxypropan-2-yl)-11-methyl-1,2-dihydrofuro[2,3-c]acridin-6-one
Synonyms:	Gravacridondiolmonomethyl Ether
Standard InCHIKey:	YYTVGIBSAJVHGD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H21NO5/c1-20(24,10-25-3)16-8-12-15(26-16)9-14(22)17-18(12)21(2)13-7-5-4-6-11(13)19(17)23/h4-7,9,16,22,24H,8,10H2,1-3H3
SMILES:	CC(COC)(C1Cc2c(cc(c3c2n(C)c2ccccc2c3=O)O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560820
PubChem CID:	5317837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001811] Acridones

*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
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12568545]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191562]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28093914]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3000.0	nM	PMID[468709]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3000.0	nM	PMID[468709]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	3000.0	nM	PMID[468709]

☑ 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 NPC116178 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	469
0.1-0.2	2189
0.2-0.3	9423
0.3-0.4	7870
0.4-0.5	7350
0.5-0.6	10513
0.6-0.7	4420
0.7-0.8	405
0.8-0.85	30
0.85-0.9	16
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9947	High Similarity	NPC217903
0.9842	High Similarity	NPC321166
0.9734	High Similarity	NPC198160
0.9592	High Similarity	NPC329830
0.9316	High Similarity	NPC15987
0.9105	High Similarity	NPC234933
0.9043	High Similarity	NPC206109
0.9043	High Similarity	NPC114039
0.8945	High Similarity	NPC30749
0.8939	High Similarity	NPC295479
0.8939	High Similarity	NPC220241
0.8918	High Similarity	NPC288759
0.8894	High Similarity	NPC305542
0.8832	High Similarity	NPC212123
0.8827	High Similarity	NPC301292
0.8827	High Similarity	NPC313112
0.8763	High Similarity	NPC241263
0.8676	High Similarity	NPC182853
0.8612	High Similarity	NPC13249
0.8594	High Similarity	NPC1820
0.8585	High Similarity	NPC134702
0.8564	High Similarity	NPC218303
0.8551	High Similarity	NPC118189
0.8529	High Similarity	NPC176113
0.8511	High Similarity	NPC298320
0.8462	Intermediate Similarity	NPC76478
0.8462	Intermediate Similarity	NPC7560
0.8439	Intermediate Similarity	NPC148391
0.8424	Intermediate Similarity	NPC474366
0.839	Intermediate Similarity	NPC114468
0.835	Intermediate Similarity	NPC2905
0.8325	Intermediate Similarity	NPC170333
0.8317	Intermediate Similarity	NPC87560
0.8317	Intermediate Similarity	NPC195120
0.8301	Intermediate Similarity	NPC268223
0.8216	Intermediate Similarity	NPC285254
0.8152	Intermediate Similarity	NPC157983
0.8152	Intermediate Similarity	NPC118154
0.8088	Intermediate Similarity	NPC133156
0.8068	Intermediate Similarity	NPC25961
0.799	Intermediate Similarity	NPC327005
0.7951	Intermediate Similarity	NPC41216
0.7926	Intermediate Similarity	NPC204867
0.7789	Intermediate Similarity	NPC299582
0.7685	Intermediate Similarity	NPC471825
0.766	Intermediate Similarity	NPC472580
0.7619	Intermediate Similarity	NPC477957
0.7619	Intermediate Similarity	NPC473996
0.7602	Intermediate Similarity	NPC129578
0.758	Intermediate Similarity	NPC251071
0.7566	Intermediate Similarity	NPC472636
0.7563	Intermediate Similarity	NPC9475
0.7538	Intermediate Similarity	NPC309692
0.7537	Intermediate Similarity	NPC469437
0.7526	Intermediate Similarity	NPC476238
0.7526	Intermediate Similarity	NPC31627
0.7526	Intermediate Similarity	NPC327269
0.7526	Intermediate Similarity	NPC285623
0.7513	Intermediate Similarity	NPC472421
0.7489	Intermediate Similarity	NPC469439
0.7474	Intermediate Similarity	NPC474772
0.7474	Intermediate Similarity	NPC472422
0.7474	Intermediate Similarity	NPC471676
0.7474	Intermediate Similarity	NPC263384
0.7474	Intermediate Similarity	NPC471675
0.7474	Intermediate Similarity	NPC474744
0.7474	Intermediate Similarity	NPC244577
0.7474	Intermediate Similarity	NPC472420
0.7474	Intermediate Similarity	NPC472423
0.7452	Intermediate Similarity	NPC17677
0.7452	Intermediate Similarity	NPC83019
0.7451	Intermediate Similarity	NPC45389
0.7421	Intermediate Similarity	NPC148124
0.7404	Intermediate Similarity	NPC204580
0.7396	Intermediate Similarity	NPC223701
0.7396	Intermediate Similarity	NPC7989
0.7396	Intermediate Similarity	NPC472583
0.7389	Intermediate Similarity	NPC476429
0.7383	Intermediate Similarity	NPC207873
0.7383	Intermediate Similarity	NPC100573
0.7382	Intermediate Similarity	NPC471677
0.738	Intermediate Similarity	NPC151171
0.7376	Intermediate Similarity	NPC99724
0.7368	Intermediate Similarity	NPC472628
0.7358	Intermediate Similarity	NPC477958
0.7354	Intermediate Similarity	NPC122886
0.7354	Intermediate Similarity	NPC472627
0.7354	Intermediate Similarity	NPC14875
0.7349	Intermediate Similarity	NPC477160
0.7344	Intermediate Similarity	NPC171651
0.7344	Intermediate Similarity	NPC475790
0.7344	Intermediate Similarity	NPC243171
0.7344	Intermediate Similarity	NPC35567
0.734	Intermediate Similarity	NPC209040
0.7327	Intermediate Similarity	NPC127996
0.7324	Intermediate Similarity	NPC268077
0.7316	Intermediate Similarity	NPC168085
0.7313	Intermediate Similarity	NPC5167
0.7313	Intermediate Similarity	NPC85613
0.7308	Intermediate Similarity	NPC264938
0.7306	Intermediate Similarity	NPC293286
0.7306	Intermediate Similarity	NPC469405
0.73	Intermediate Similarity	NPC127082
0.7297	Intermediate Similarity	NPC128476
0.7296	Intermediate Similarity	NPC328102
0.7296	Intermediate Similarity	NPC472624
0.7292	Intermediate Similarity	NPC319910
0.7292	Intermediate Similarity	NPC254412
0.7292	Intermediate Similarity	NPC262038
0.7292	Intermediate Similarity	NPC262039
0.7292	Intermediate Similarity	NPC474021
0.7292	Intermediate Similarity	NPC474023
0.7292	Intermediate Similarity	NPC278476
0.7289	Intermediate Similarity	NPC248903
0.7287	Intermediate Similarity	NPC143896
0.7287	Intermediate Similarity	NPC310130
0.7287	Intermediate Similarity	NPC68104
0.7287	Intermediate Similarity	NPC221432
0.7287	Intermediate Similarity	NPC478086
0.7287	Intermediate Similarity	NPC150408
0.7287	Intermediate Similarity	NPC164980
0.7287	Intermediate Similarity	NPC18585
0.7287	Intermediate Similarity	NPC39329
0.7287	Intermediate Similarity	NPC175504
0.7287	Intermediate Similarity	NPC257097
0.7287	Intermediate Similarity	NPC91560
0.7287	Intermediate Similarity	NPC75049
0.7287	Intermediate Similarity	NPC149026
0.7287	Intermediate Similarity	NPC214166
0.7287	Intermediate Similarity	NPC169591
0.7287	Intermediate Similarity	NPC316816
0.7287	Intermediate Similarity	NPC166138
0.7287	Intermediate Similarity	NPC106985
0.7284	Intermediate Similarity	NPC469722
0.7282	Intermediate Similarity	NPC474059
0.7277	Intermediate Similarity	NPC97746
0.7277	Intermediate Similarity	NPC89442
0.7277	Intermediate Similarity	NPC317492
0.7273	Intermediate Similarity	NPC472581
0.7273	Intermediate Similarity	NPC124038
0.7268	Intermediate Similarity	NPC108937
0.7268	Intermediate Similarity	NPC304207
0.7268	Intermediate Similarity	NPC48579
0.7268	Intermediate Similarity	NPC207809
0.7268	Intermediate Similarity	NPC217706
0.7268	Intermediate Similarity	NPC279218
0.7268	Intermediate Similarity	NPC259710
0.7268	Intermediate Similarity	NPC470681
0.7264	Intermediate Similarity	NPC471489
0.7263	Intermediate Similarity	NPC110303
0.7263	Intermediate Similarity	NPC296998
0.7263	Intermediate Similarity	NPC23728
0.7263	Intermediate Similarity	NPC473077
0.7259	Intermediate Similarity	NPC30655
0.7259	Intermediate Similarity	NPC92589
0.7259	Intermediate Similarity	NPC74854
0.7259	Intermediate Similarity	NPC45124
0.7256	Intermediate Similarity	NPC478075
0.7254	Intermediate Similarity	NPC150123
0.7254	Intermediate Similarity	NPC244583
0.7254	Intermediate Similarity	NPC217149
0.7254	Intermediate Similarity	NPC216035
0.7254	Intermediate Similarity	NPC10807
0.7254	Intermediate Similarity	NPC161881
0.7254	Intermediate Similarity	NPC138288
0.7254	Intermediate Similarity	NPC56232
0.7254	Intermediate Similarity	NPC210597
0.7253	Intermediate Similarity	NPC188400
0.725	Intermediate Similarity	NPC168153
0.7249	Intermediate Similarity	NPC236766
0.7249	Intermediate Similarity	NPC473013
0.7249	Intermediate Similarity	NPC131568
0.7249	Intermediate Similarity	NPC473015
0.7249	Intermediate Similarity	NPC197252
0.7249	Intermediate Similarity	NPC131579
0.7244	Intermediate Similarity	NPC476436
0.7244	Intermediate Similarity	NPC26928
0.7243	Intermediate Similarity	NPC87714
0.724	Intermediate Similarity	NPC105136
0.7236	Intermediate Similarity	NPC108433
0.7236	Intermediate Similarity	NPC300053
0.7234	Intermediate Similarity	NPC177354
0.7234	Intermediate Similarity	NPC107572
0.7234	Intermediate Similarity	NPC161506
0.7234	Intermediate Similarity	NPC37496
0.7234	Intermediate Similarity	NPC125855
0.7234	Intermediate Similarity	NPC166934
0.7234	Intermediate Similarity	NPC64915
0.7234	Intermediate Similarity	NPC147145
0.7234	Intermediate Similarity	NPC76338
0.7234	Intermediate Similarity	NPC265040
0.7234	Intermediate Similarity	NPC306829
0.7234	Intermediate Similarity	NPC1089
0.7234	Intermediate Similarity	NPC194432
0.7234	Intermediate Similarity	NPC296917
0.7234	Intermediate Similarity	NPC167624
0.7234	Intermediate Similarity	NPC324134
0.7234	Intermediate Similarity	NPC166482
0.7234	Intermediate Similarity	NPC32739
0.7234	Intermediate Similarity	NPC66515

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 NPC116178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	628
0.2-0.3	937
0.3-0.4	1675
0.4-0.5	2565
0.5-0.6	2157
0.6-0.7	775
0.7-0.8	96
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8454	Intermediate Similarity	NPD2899	Discontinued
0.8009	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3298	Approved
0.767	Intermediate Similarity	NPD6874	Approved
0.7667	Intermediate Similarity	NPD7584	Approved
0.7659	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8461	Discontinued
0.75	Intermediate Similarity	NPD3297	Approved
0.7443	Intermediate Similarity	NPD5496	Approved
0.7397	Intermediate Similarity	NPD6198	Phase 1
0.7395	Intermediate Similarity	NPD5726	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6625	Approved
0.7356	Intermediate Similarity	NPD4361	Phase 2
0.7356	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4363	Phase 3
0.7308	Intermediate Similarity	NPD4360	Phase 2
0.7301	Intermediate Similarity	NPD4981	Phase 2
0.7269	Intermediate Similarity	NPD6962	Phase 2
0.7244	Intermediate Similarity	NPD7186	Phase 3
0.7222	Intermediate Similarity	NPD5183	Approved
0.7222	Intermediate Similarity	NPD5186	Approved
0.7222	Intermediate Similarity	NPD7585	Approved
0.7217	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5937	Approved
0.7194	Intermediate Similarity	NPD7075	Discontinued
0.7193	Intermediate Similarity	NPD8067	Phase 3
0.7192	Intermediate Similarity	NPD6104	Discontinued
0.7176	Intermediate Similarity	NPD7583	Approved
0.715	Intermediate Similarity	NPD4380	Phase 2
0.7137	Intermediate Similarity	NPD1483	Discontinued
0.7128	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3925	Approved
0.7123	Intermediate Similarity	NPD4668	Phase 2
0.7114	Intermediate Similarity	NPD3446	Phase 1
0.7112	Intermediate Similarity	NPD4846	Phase 2
0.7097	Intermediate Similarity	NPD6296	Discontinued
0.7094	Intermediate Similarity	NPD7417	Discontinued
0.707	Intermediate Similarity	NPD5006	Approved
0.707	Intermediate Similarity	NPD5005	Approved
0.7059	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4373	Phase 2
0.7044	Intermediate Similarity	NPD6020	Phase 2
0.7044	Intermediate Similarity	NPD3793	Phase 3
0.7029	Intermediate Similarity	NPD8367	Approved
0.7021	Intermediate Similarity	NPD1549	Phase 2
0.7019	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4465	Phase 2
0.7005	Intermediate Similarity	NPD4467	Phase 2
0.7005	Intermediate Similarity	NPD5102	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7626	Approved
0.6991	Remote Similarity	NPD7627	Approved
0.699	Remote Similarity	NPD1934	Approved
0.6983	Remote Similarity	NPD8492	Approved
0.6979	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD3823	Discontinued
0.6968	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD683	Approved
0.6968	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7803	Approved
0.6961	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7654	Discontinued
0.6948	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD955	Approved
0.6935	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD4952	Phase 3
0.6923	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7907	Approved
0.6913	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7922	Phase 1
0.6907	Remote Similarity	NPD4613	Phase 2
0.6907	Remote Similarity	NPD7560	Approved
0.6905	Remote Similarity	NPD1898	Discontinued
0.6904	Remote Similarity	NPD6801	Discontinued
0.6897	Remote Similarity	NPD2248	Approved
0.6897	Remote Similarity	NPD2246	Approved
0.6891	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3154	Approved
0.689	Remote Similarity	NPD3153	Approved
0.6884	Remote Similarity	NPD4420	Approved
0.6884	Remote Similarity	NPD3882	Suspended
0.6878	Remote Similarity	NPD6790	Phase 1
0.6875	Remote Similarity	NPD7559	Phase 2
0.6872	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3452	Approved
0.6866	Remote Similarity	NPD2494	Approved
0.6866	Remote Similarity	NPD3450	Approved
0.6866	Remote Similarity	NPD2493	Approved
0.6864	Remote Similarity	NPD7263	Phase 2
0.6856	Remote Similarity	NPD7278	Phase 2
0.6856	Remote Similarity	NPD7279	Phase 2
0.6854	Remote Similarity	NPD4466	Phase 1
0.6854	Remote Similarity	NPD4539	Phase 1
0.6853	Remote Similarity	NPD7411	Suspended
0.6847	Remote Similarity	NPD5860	Discontinued
0.6847	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2821	Approved
0.6828	Remote Similarity	NPD4665	Approved
0.6828	Remote Similarity	NPD4111	Phase 1
0.6825	Remote Similarity	NPD2796	Approved
0.6816	Remote Similarity	NPD1945	Phase 1
0.6814	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6997	Phase 2
0.6806	Remote Similarity	NPD2654	Approved
0.6806	Remote Similarity	NPD5071	Phase 2
0.6802	Remote Similarity	NPD7708	Approved
0.68	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7546	Discontinued
0.6792	Remote Similarity	NPD5928	Phase 1
0.6792	Remote Similarity	NPD4258	Approved
0.6792	Remote Similarity	NPD4259	Approved
0.6789	Remote Similarity	NPD6321	Discontinued
0.6784	Remote Similarity	NPD1926	Approved
0.6784	Remote Similarity	NPD7819	Suspended
0.6782	Remote Similarity	NPD5494	Approved
0.6779	Remote Similarity	NPD6559	Discontinued
0.6773	Remote Similarity	NPD4582	Approved
0.6773	Remote Similarity	NPD4583	Approved
0.6772	Remote Similarity	NPD1510	Phase 2
0.6771	Remote Similarity	NPD5914	Approved
0.6768	Remote Similarity	NPD2366	Approved
0.6765	Remote Similarity	NPD5242	Approved
0.6761	Remote Similarity	NPD7955	Approved
0.6761	Remote Similarity	NPD2488	Approved
0.6761	Remote Similarity	NPD7956	Approved
0.6761	Remote Similarity	NPD2490	Approved
0.6759	Remote Similarity	NPD2975	Approved
0.6759	Remote Similarity	NPD2973	Approved
0.6759	Remote Similarity	NPD2974	Approved
0.6758	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD3057	Approved
0.6757	Remote Similarity	NPD7701	Phase 2
0.6753	Remote Similarity	NPD6799	Approved
0.6751	Remote Similarity	NPD7048	Phase 3
0.6749	Remote Similarity	NPD6457	Approved
0.6748	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3818	Discontinued
0.6743	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7577	Discontinued
0.6734	Remote Similarity	NPD6844	Discontinued
0.6732	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6166	Phase 2
0.6727	Remote Similarity	NPD7497	Discontinued
0.6727	Remote Similarity	NPD4004	Approved
0.6727	Remote Similarity	NPD4002	Approved
0.6725	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7224	Discontinued
0.6724	Remote Similarity	NPD7223	Discontinued
0.6716	Remote Similarity	NPD5710	Approved
0.6716	Remote Similarity	NPD5711	Approved
0.6715	Remote Similarity	NPD3965	Phase 1
0.6712	Remote Similarity	NPD7043	Discontinued
0.6711	Remote Similarity	NPD5632	Approved
0.6709	Remote Similarity	NPD6199	Discontinued
0.6708	Remote Similarity	NPD6716	Phase 1
0.67	Remote Similarity	NPD2801	Approved
0.6699	Remote Similarity	NPD5637	Discontinued
0.6697	Remote Similarity	NPD7810	Phase 3
0.6697	Remote Similarity	NPD1880	Phase 3
0.6697	Remote Similarity	NPD7811	Phase 3
0.6696	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7556	Discontinued
0.6696	Remote Similarity	NPD5025	Approved
0.6695	Remote Similarity	NPD6723	Discontinued
0.6694	Remote Similarity	NPD5488	Discontinued
0.6683	Remote Similarity	NPD5890	Approved
0.6683	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5889	Approved
0.6683	Remote Similarity	NPD7479	Phase 2
0.6682	Remote Similarity	NPD2907	Approved
0.6682	Remote Similarity	NPD4605	Approved
0.6682	Remote Similarity	NPD2491	Approved
0.6682	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD3533	Approved
0.6682	Remote Similarity	NPD8054	Approved
0.6682	Remote Similarity	NPD2906	Approved
0.6682	Remote Similarity	NPD4604	Approved
0.6682	Remote Similarity	NPD2972	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