NPASS Compound

Structure

NPC186647 OpenBabel07101719242D 24 27 0 0 0 0 0 0 0 0999 V2000 -0.6945 4.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 -1.8345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6356 -0.2485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7696 -0.7485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6356 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9036 -0.2485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7696 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4265 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0376 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4265 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3890 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9036 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0376 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 -0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 0.7515 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 0.7818 -0.6235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 3.7515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 -1.3345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 2 0 0 0 0 13 15 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.11
Volume:	337.552
LogP:	4.515
LogD:	3.734
LogS:	-6.394
# Rotatable Bonds:	3
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.702
Synthetic Accessibility Score:	2.323
Fsp3:	0.095
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.005
MDCK Permeability:	2.01530747290235e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.518
30% Bioavailability (F30%):	0.34

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	98.51519012451172%
Volume Distribution (VD):	0.436
Pgp-substrate:	0.5434160828590393%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.463
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.754
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	4.624
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.55
Human Hepatotoxicity (H-HT):	0.855
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.941
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.703
Skin Sensitization:	0.944
Carcinogencity:	0.94
Eye Corrosion:	0.004
Eye Irritation:	0.838
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC186647

Natural Product ID:	NPC186647
*Common Name:**	RGAMWXVDURAYGK-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RGAMWXVDURAYGK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H16O3/c1-23-17-11-8-14-12-18(24-2)21(22)20-15(9-10-16(17)19(14)20)13-6-4-3-5-7-13/h3-12H,1-2H3
SMILES:	COC1=Cc2ccc(c3c2c(C1=O)c(cc3)c1ccccc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3589054
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002044] Phenylnaphthalenes

*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
NPO32893	haemodorum spicatum	Species	Haemodoraceae	Eukaryota	n.a.	Australian	n.a.	PMID[26090896]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	1.0	mm	PMID[456046]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	3.0	mm	PMID[456046]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	IZ	=	1.0	mm	PMID[456046]

☑ 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 NPC186647 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	495
0.1-0.2	1885
0.2-0.3	4401
0.3-0.4	11798
0.4-0.5	6130
0.5-0.6	4934
0.6-0.7	8350
0.7-0.8	4507
0.8-0.85	153
0.85-0.9	33
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9489	High Similarity	NPC472836
0.9466	High Similarity	NPC183103
0.9394	High Similarity	NPC470406
0.9231	High Similarity	NPC428300
0.9118	High Similarity	NPC290601
0.9111	High Similarity	NPC22644
0.9098	High Similarity	NPC164295
0.9098	High Similarity	NPC239134
0.9085	High Similarity	NPC472839
0.9085	High Similarity	NPC472841
0.9044	High Similarity	NPC471670
0.9028	High Similarity	NPC472838
0.9028	High Similarity	NPC306011
0.9008	High Similarity	NPC474737
0.8986	High Similarity	NPC470407
0.8936	High Similarity	NPC308006
0.8864	High Similarity	NPC177925
0.8836	High Similarity	NPC27615
0.8828	High Similarity	NPC58310
0.8828	High Similarity	NPC295977
0.8794	High Similarity	NPC201297
0.875	High Similarity	NPC478163
0.8667	High Similarity	NPC57552
0.8662	High Similarity	NPC69755
0.8658	High Similarity	NPC288353
0.8639	High Similarity	NPC474414
0.863	High Similarity	NPC80370
0.8621	High Similarity	NPC58373
0.8613	High Similarity	NPC312560
0.8601	High Similarity	NPC53016
0.8601	High Similarity	NPC472840
0.8591	High Similarity	NPC478161
0.8591	High Similarity	NPC478159
0.8571	High Similarity	NPC75432
0.8571	High Similarity	NPC301341
0.8561	High Similarity	NPC88065
0.8561	High Similarity	NPC89504
0.8561	High Similarity	NPC95485
0.854	High Similarity	NPC279596
0.8514	High Similarity	NPC189773
0.8514	High Similarity	NPC230848
0.8511	High Similarity	NPC475104
0.8489	Intermediate Similarity	NPC1249
0.8483	Intermediate Similarity	NPC478166
0.8483	Intermediate Similarity	NPC49282
0.8472	Intermediate Similarity	NPC167663
0.8467	Intermediate Similarity	NPC27659
0.8467	Intermediate Similarity	NPC470725
0.8456	Intermediate Similarity	NPC181675
0.8456	Intermediate Similarity	NPC96024
0.8451	Intermediate Similarity	NPC223336
0.8444	Intermediate Similarity	NPC474264
0.844	Intermediate Similarity	NPC284184
0.8435	Intermediate Similarity	NPC474107
0.8385	Intermediate Similarity	NPC469954
0.8378	Intermediate Similarity	NPC300983
0.8378	Intermediate Similarity	NPC472837
0.8367	Intermediate Similarity	NPC478018
0.8356	Intermediate Similarity	NPC478160
0.8356	Intermediate Similarity	NPC478019
0.8344	Intermediate Similarity	NPC226656
0.8344	Intermediate Similarity	NPC3898
0.8344	Intermediate Similarity	NPC66508
0.8333	Intermediate Similarity	NPC253488
0.8333	Intermediate Similarity	NPC245395
0.8333	Intermediate Similarity	NPC149780
0.8301	Intermediate Similarity	NPC228654
0.8299	Intermediate Similarity	NPC39361
0.8296	Intermediate Similarity	NPC56332
0.8296	Intermediate Similarity	NPC164014
0.8289	Intermediate Similarity	NPC276231
0.8288	Intermediate Similarity	NPC189650
0.8288	Intermediate Similarity	NPC290038
0.8288	Intermediate Similarity	NPC245522
0.8288	Intermediate Similarity	NPC114513
0.8267	Intermediate Similarity	NPC144283
0.8261	Intermediate Similarity	NPC276238
0.8261	Intermediate Similarity	NPC171460
0.8255	Intermediate Similarity	NPC329933
0.8252	Intermediate Similarity	NPC233707
0.8244	Intermediate Similarity	NPC25648
0.8243	Intermediate Similarity	NPC34802
0.8239	Intermediate Similarity	NPC475549
0.8239	Intermediate Similarity	NPC232996
0.8235	Intermediate Similarity	NPC67197
0.8235	Intermediate Similarity	NPC232387
0.8227	Intermediate Similarity	NPC324117
0.8227	Intermediate Similarity	NPC209858
0.8222	Intermediate Similarity	NPC182646
0.8219	Intermediate Similarity	NPC478164
0.8214	Intermediate Similarity	NPC474340
0.8194	Intermediate Similarity	NPC1268
0.8194	Intermediate Similarity	NPC477408
0.8194	Intermediate Similarity	NPC219686
0.8188	Intermediate Similarity	NPC474556
0.8182	Intermediate Similarity	NPC324736
0.8182	Intermediate Similarity	NPC245891
0.8182	Intermediate Similarity	NPC104876
0.8182	Intermediate Similarity	NPC264022
0.8175	Intermediate Similarity	NPC254492
0.817	Intermediate Similarity	NPC213401
0.817	Intermediate Similarity	NPC279605
0.8169	Intermediate Similarity	NPC217914
0.8163	Intermediate Similarity	NPC300603
0.8163	Intermediate Similarity	NPC309169
0.8163	Intermediate Similarity	NPC91694
0.8163	Intermediate Similarity	NPC260152
0.8163	Intermediate Similarity	NPC196941
0.8162	Intermediate Similarity	NPC199273
0.8158	Intermediate Similarity	NPC329844
0.8156	Intermediate Similarity	NPC78307
0.8151	Intermediate Similarity	NPC137920
0.8151	Intermediate Similarity	NPC141817
0.8151	Intermediate Similarity	NPC176030
0.8151	Intermediate Similarity	NPC192597
0.8151	Intermediate Similarity	NPC169214
0.8151	Intermediate Similarity	NPC86455
0.8151	Intermediate Similarity	NPC229218
0.8151	Intermediate Similarity	NPC125134
0.8146	Intermediate Similarity	NPC118332
0.8143	Intermediate Similarity	NPC301717
0.8143	Intermediate Similarity	NPC205360
0.8121	Intermediate Similarity	NPC118027
0.8121	Intermediate Similarity	NPC289042
0.8121	Intermediate Similarity	NPC190648
0.8121	Intermediate Similarity	NPC126767
0.8121	Intermediate Similarity	NPC312929
0.8121	Intermediate Similarity	NPC56433
0.8121	Intermediate Similarity	NPC245584
0.8117	Intermediate Similarity	NPC474637
0.8116	Intermediate Similarity	NPC72667
0.8116	Intermediate Similarity	NPC78364
0.8116	Intermediate Similarity	NPC176130
0.8116	Intermediate Similarity	NPC69424
0.8116	Intermediate Similarity	NPC84672
0.8102	Intermediate Similarity	NPC123506
0.8099	Intermediate Similarity	NPC274876
0.8099	Intermediate Similarity	NPC213122
0.8099	Intermediate Similarity	NPC50924
0.8095	Intermediate Similarity	NPC163948
0.8095	Intermediate Similarity	NPC84266
0.8092	Intermediate Similarity	NPC164912
0.8092	Intermediate Similarity	NPC10429
0.8085	Intermediate Similarity	NPC153453
0.8082	Intermediate Similarity	NPC124365
0.8079	Intermediate Similarity	NPC255641
0.8079	Intermediate Similarity	NPC475718
0.8079	Intermediate Similarity	NPC290954
0.8079	Intermediate Similarity	NPC205766
0.8079	Intermediate Similarity	NPC470568
0.8079	Intermediate Similarity	NPC474660
0.8077	Intermediate Similarity	NPC67377
0.8069	Intermediate Similarity	NPC476191
0.8067	Intermediate Similarity	NPC95526
0.8067	Intermediate Similarity	NPC472056
0.8056	Intermediate Similarity	NPC470721
0.8056	Intermediate Similarity	NPC6100
0.8056	Intermediate Similarity	NPC156888
0.8056	Intermediate Similarity	NPC470722
0.8054	Intermediate Similarity	NPC473927
0.8052	Intermediate Similarity	NPC474360
0.8045	Intermediate Similarity	NPC171023
0.8042	Intermediate Similarity	NPC283088
0.8041	Intermediate Similarity	NPC93241
0.8041	Intermediate Similarity	NPC471305
0.8041	Intermediate Similarity	NPC27798
0.8041	Intermediate Similarity	NPC471451
0.8038	Intermediate Similarity	NPC26386
0.8029	Intermediate Similarity	NPC30216
0.8029	Intermediate Similarity	NPC111088
0.8028	Intermediate Similarity	NPC59459
0.8028	Intermediate Similarity	NPC225051
0.8027	Intermediate Similarity	NPC182255
0.8027	Intermediate Similarity	NPC94076
0.8026	Intermediate Similarity	NPC149526
0.8026	Intermediate Similarity	NPC473201
0.8026	Intermediate Similarity	NPC470569
0.8026	Intermediate Similarity	NPC474417
0.8026	Intermediate Similarity	NPC118427
0.8026	Intermediate Similarity	NPC302783
0.8025	Intermediate Similarity	NPC475144
0.8015	Intermediate Similarity	NPC282577
0.8014	Intermediate Similarity	NPC477412
0.8014	Intermediate Similarity	NPC471851
0.8014	Intermediate Similarity	NPC72669
0.8014	Intermediate Similarity	NPC474517
0.8013	Intermediate Similarity	NPC472052
0.8013	Intermediate Similarity	NPC472298
0.8013	Intermediate Similarity	NPC65784
0.8013	Intermediate Similarity	NPC472060
0.8013	Intermediate Similarity	NPC284495
0.8013	Intermediate Similarity	NPC158338
0.8013	Intermediate Similarity	NPC100985
0.8013	Intermediate Similarity	NPC288036
0.8013	Intermediate Similarity	NPC97029
0.8013	Intermediate Similarity	NPC470342
0.8013	Intermediate Similarity	NPC97028
0.8013	Intermediate Similarity	NPC65589
0.8	Intermediate Similarity	NPC167098
0.8	Intermediate Similarity	NPC52692

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 NPC186647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	466
0.1-0.2	994
0.2-0.3	1253
0.3-0.4	2592
0.4-0.5	2051
0.5-0.6	1165
0.6-0.7	498
0.7-0.8	125
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8538	High Similarity	NPD1651	Approved
0.8462	Intermediate Similarity	NPD7003	Approved
0.8421	Intermediate Similarity	NPD3972	Approved
0.8209	Intermediate Similarity	NPD1281	Approved
0.8029	Intermediate Similarity	NPD1876	Approved
0.8029	Intermediate Similarity	NPD1283	Approved
0.7895	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7458	Discontinued
0.7891	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD2346	Discontinued
0.7877	Intermediate Similarity	NPD1471	Phase 3
0.7852	Intermediate Similarity	NPD5691	Approved
0.7832	Intermediate Similarity	NPD2979	Phase 3
0.7794	Intermediate Similarity	NPD4626	Approved
0.7786	Intermediate Similarity	NPD2798	Approved
0.774	Intermediate Similarity	NPD3748	Approved
0.7736	Intermediate Similarity	NPD6959	Discontinued
0.7697	Intermediate Similarity	NPD6273	Approved
0.7692	Intermediate Similarity	NPD7819	Suspended
0.7688	Intermediate Similarity	NPD6232	Discontinued
0.7687	Intermediate Similarity	NPD2935	Discontinued
0.7687	Intermediate Similarity	NPD2796	Approved
0.7669	Intermediate Similarity	NPD5844	Phase 1
0.7662	Intermediate Similarity	NPD3226	Approved
0.7654	Intermediate Similarity	NPD7473	Discontinued
0.7643	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2344	Approved
0.7632	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2799	Discontinued
0.7603	Intermediate Similarity	NPD1607	Approved
0.7568	Intermediate Similarity	NPD5404	Approved
0.7568	Intermediate Similarity	NPD5408	Approved
0.7568	Intermediate Similarity	NPD5406	Approved
0.7568	Intermediate Similarity	NPD5405	Approved
0.7568	Intermediate Similarity	NPD2531	Phase 2
0.7568	Intermediate Similarity	NPD2438	Suspended
0.7566	Intermediate Similarity	NPD7390	Discontinued
0.7554	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD1241	Discontinued
0.7536	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD8032	Phase 2
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD7177	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3750	Approved
0.7468	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1240	Approved
0.7452	Intermediate Similarity	NPD7411	Suspended
0.7448	Intermediate Similarity	NPD6798	Discontinued
0.7434	Intermediate Similarity	NPD2309	Approved
0.7429	Intermediate Similarity	NPD1201	Approved
0.7421	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1510	Phase 2
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7347	Intermediate Similarity	NPD4060	Phase 1
0.7347	Intermediate Similarity	NPD4307	Phase 2
0.7346	Intermediate Similarity	NPD5494	Approved
0.7343	Intermediate Similarity	NPD1470	Approved
0.7338	Intermediate Similarity	NPD6799	Approved
0.7329	Intermediate Similarity	NPD7075	Discontinued
0.7329	Intermediate Similarity	NPD2313	Discontinued
0.7326	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3887	Approved
0.7319	Intermediate Similarity	NPD5536	Phase 2
0.7305	Intermediate Similarity	NPD1611	Approved
0.7296	Intermediate Similarity	NPD6801	Discontinued
0.729	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD17	Approved
0.7285	Intermediate Similarity	NPD2353	Approved
0.7285	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4380	Phase 2
0.7273	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7768	Phase 2
0.726	Intermediate Similarity	NPD7008	Discontinued
0.725	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2897	Discontinued
0.7222	Intermediate Similarity	NPD3749	Approved
0.7222	Intermediate Similarity	NPD3267	Approved
0.7222	Intermediate Similarity	NPD3266	Approved
0.7219	Intermediate Similarity	NPD4476	Approved
0.7219	Intermediate Similarity	NPD4477	Approved
0.7214	Intermediate Similarity	NPD3025	Approved
0.7214	Intermediate Similarity	NPD3024	Approved
0.7212	Intermediate Similarity	NPD3926	Phase 2
0.7211	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3764	Approved
0.7208	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3817	Phase 2
0.7205	Intermediate Similarity	NPD5978	Approved
0.7205	Intermediate Similarity	NPD5977	Approved
0.7203	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6832	Phase 2
0.719	Intermediate Similarity	NPD1243	Approved
0.7188	Intermediate Similarity	NPD6280	Approved
0.7188	Intermediate Similarity	NPD6279	Approved
0.7181	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD2534	Approved
0.7179	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2532	Approved
0.7178	Intermediate Similarity	NPD919	Approved
0.7169	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6166	Phase 2
0.7163	Intermediate Similarity	NPD3019	Approved
0.7163	Intermediate Similarity	NPD2932	Approved
0.716	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD7095	Approved
0.7134	Intermediate Similarity	NPD5049	Phase 3
0.7133	Intermediate Similarity	NPD1608	Approved
0.7124	Intermediate Similarity	NPD1549	Phase 2
0.7124	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3142	Approved
0.7114	Intermediate Similarity	NPD3140	Approved
0.7113	Intermediate Similarity	NPD3023	Approved
0.7113	Intermediate Similarity	NPD3026	Approved
0.7111	Intermediate Similarity	NPD5451	Approved
0.7105	Intermediate Similarity	NPD6100	Approved
0.7105	Intermediate Similarity	NPD6099	Approved
0.7103	Intermediate Similarity	NPD2797	Approved
0.7097	Intermediate Similarity	NPD2354	Approved
0.7095	Intermediate Similarity	NPD3268	Approved
0.7092	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1247	Approved
0.7089	Intermediate Similarity	NPD7427	Discontinued
0.7083	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5327	Phase 3
0.7081	Intermediate Similarity	NPD7577	Discontinued
0.7067	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7236	Approved
0.7047	Intermediate Similarity	NPD6233	Phase 2
0.7042	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD8166	Discontinued
0.7029	Intermediate Similarity	NPD5283	Phase 1
0.7027	Intermediate Similarity	NPD4625	Phase 3
0.7025	Intermediate Similarity	NPD1512	Approved
0.702	Intermediate Similarity	NPD4097	Suspended
0.7007	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3751	Discontinued
0.6981	Remote Similarity	NPD920	Approved
0.6978	Remote Similarity	NPD5951	Approved
0.6975	Remote Similarity	NPD1934	Approved
0.6966	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1669	Approved
0.6963	Remote Similarity	NPD2342	Discontinued
0.6962	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7028	Phase 2
0.6957	Remote Similarity	NPD5535	Approved
0.6946	Remote Similarity	NPD7229	Phase 3
0.6943	Remote Similarity	NPD3300	Phase 2
0.6941	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4624	Approved
0.6937	Remote Similarity	NPD7239	Suspended
0.6936	Remote Similarity	NPD8313	Approved
0.6936	Remote Similarity	NPD8312	Approved
0.6933	Remote Similarity	NPD2801	Approved
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6559	Discontinued
0.6914	Remote Similarity	NPD6873	Phase 2
0.6914	Remote Similarity	NPD8150	Discontinued
0.6913	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1511	Approved
0.6894	Remote Similarity	NPD2649	Approved
0.6894	Remote Similarity	NPD2651	Approved
0.689	Remote Similarity	NPD5402	Approved
0.689	Remote Similarity	NPD2296	Approved
0.6887	Remote Similarity	NPD4140	Approved
0.6875	Remote Similarity	NPD3869	Phase 3
0.6875	Remote Similarity	NPD3873	Phase 3
0.6875	Remote Similarity	NPD5403	Approved
0.6871	Remote Similarity	NPD1164	Approved
0.6868	Remote Similarity	NPD6782	Approved
0.6868	Remote Similarity	NPD6778	Approved
0.6868	Remote Similarity	NPD6777	Approved
0.6868	Remote Similarity	NPD6781	Approved
0.6868	Remote Similarity	NPD6780	Approved
0.6868	Remote Similarity	NPD6776	Approved
0.6868	Remote Similarity	NPD6779	Approved
0.6867	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8055	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