NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	270.459
LogP:	3.073
LogD:	2.618
LogS:	-3.979
# Rotatable Bonds:	0
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	3.51
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.747
MDCK Permeability:	2.417978430457879e-05
Pgp-inhibitor:	0.249
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.192

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	98.52352905273438%
Volume Distribution (VD):	0.433
Pgp-substrate:	2.3292741775512695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.424
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.515
CYP2D6-inhibitor:	0.935
CYP2D6-substrate:	0.192
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	7.115
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.845
AMES Toxicity:	0.851
Rat Oral Acute Toxicity:	0.394
Maximum Recommended Daily Dose:	0.628
Skin Sensitization:	0.532
Carcinogencity:	0.856
Eye Corrosion:	0.008
Eye Irritation:	0.929
Respiratory Toxicity:	0.173

Download Data

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

Natural Product: NPC476821

Natural Product ID:	NPC476821
*Common Name:**	(2S)-7,8-dihydroxy-2,3,3-trimethyl-2H-benzo[f][1]benzofuran-4,9-dione
IUPAC Name:	(2S)-7,8-dihydroxy-2,3,3-trimethyl-2H-benzo[f][1]benzofuran-4,9-dione
Synonyms:
Standard InCHIKey:	UVWMPNRHULNSJS-LURJTMIESA-N
Standard InCHI:	InChI=1S/C15H14O5/c1-6-15(2,3)10-11(17)7-4-5-8(16)12(18)9(7)13(19)14(10)20-6/h4-6,16,18H,1-3H3/t6-/m0/s1
SMILES:	C[C@H]1C(C2=C(O1)C(=O)C3=C(C2=O)C=CC(=C3O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	137629319
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO6617	Chirita eburnea	Species	Gesneriaceae	Eukaryota	whole plant	Guangxi Province, China	2002-AUG	PMID[15921435]
NPO6617	Chirita eburnea	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	124820	nM	PMID[15921435]

☑ 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 NPC476821 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	361
0.1-0.2	1419
0.2-0.3	3316
0.3-0.4	8642
0.4-0.5	10434
0.5-0.6	4601
0.6-0.7	7893
0.7-0.8	5810
0.8-0.85	205
0.85-0.9	11
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9078	High Similarity	NPC38158
0.8968	High Similarity	NPC476822
0.8759	High Similarity	NPC114620
0.8759	High Similarity	NPC103337
0.8652	High Similarity	NPC117609
0.8591	High Similarity	NPC29932
0.8571	High Similarity	NPC324209
0.8562	High Similarity	NPC173980
0.8531	High Similarity	NPC309430
0.8511	High Similarity	NPC237225
0.8511	High Similarity	NPC165257
0.8493	Intermediate Similarity	NPC147418
0.8477	Intermediate Similarity	NPC136878
0.8477	Intermediate Similarity	NPC273798
0.8472	Intermediate Similarity	NPC4170
0.8472	Intermediate Similarity	NPC171968
0.8471	Intermediate Similarity	NPC477410
0.8456	Intermediate Similarity	NPC291078
0.8435	Intermediate Similarity	NPC61398
0.8435	Intermediate Similarity	NPC416
0.8431	Intermediate Similarity	NPC44378
0.8431	Intermediate Similarity	NPC280753
0.8403	Intermediate Similarity	NPC477406
0.8403	Intermediate Similarity	NPC477407
0.8403	Intermediate Similarity	NPC88864
0.84	Intermediate Similarity	NPC143898
0.8392	Intermediate Similarity	NPC198305
0.8392	Intermediate Similarity	NPC475741
0.8389	Intermediate Similarity	NPC84273
0.8369	Intermediate Similarity	NPC51037
0.8369	Intermediate Similarity	NPC231774
0.8367	Intermediate Similarity	NPC119542
0.8367	Intermediate Similarity	NPC264022
0.8366	Intermediate Similarity	NPC132810
0.8366	Intermediate Similarity	NPC94781
0.8345	Intermediate Similarity	NPC294226
0.8345	Intermediate Similarity	NPC254603
0.8333	Intermediate Similarity	NPC248068
0.8312	Intermediate Similarity	NPC120171
0.8311	Intermediate Similarity	NPC230811
0.8302	Intermediate Similarity	NPC313368
0.8302	Intermediate Similarity	NPC323965
0.8299	Intermediate Similarity	NPC315275
0.8289	Intermediate Similarity	NPC474630
0.828	Intermediate Similarity	NPC234485
0.8276	Intermediate Similarity	NPC17843
0.8269	Intermediate Similarity	NPC161159
0.8258	Intermediate Similarity	NPC103509
0.8252	Intermediate Similarity	NPC247250
0.8252	Intermediate Similarity	NPC767
0.8247	Intermediate Similarity	NPC112816
0.8247	Intermediate Similarity	NPC470479
0.8239	Intermediate Similarity	NPC1991
0.8231	Intermediate Similarity	NPC14377
0.8231	Intermediate Similarity	NPC258502
0.8231	Intermediate Similarity	NPC129752
0.8228	Intermediate Similarity	NPC471968
0.8227	Intermediate Similarity	NPC310540
0.8224	Intermediate Similarity	NPC477409
0.8219	Intermediate Similarity	NPC193169
0.8217	Intermediate Similarity	NPC127172
0.8212	Intermediate Similarity	NPC308572
0.8205	Intermediate Similarity	NPC302783
0.8205	Intermediate Similarity	NPC92747
0.8205	Intermediate Similarity	NPC473201
0.8205	Intermediate Similarity	NPC265862
0.8205	Intermediate Similarity	NPC205918
0.82	Intermediate Similarity	NPC203063
0.82	Intermediate Similarity	NPC156872
0.82	Intermediate Similarity	NPC471853
0.8194	Intermediate Similarity	NPC134293
0.8194	Intermediate Similarity	NPC478219
0.8188	Intermediate Similarity	NPC175552
0.8182	Intermediate Similarity	NPC472135
0.8182	Intermediate Similarity	NPC473787
0.8176	Intermediate Similarity	NPC86524
0.8176	Intermediate Similarity	NPC294300
0.8176	Intermediate Similarity	NPC326847
0.8176	Intermediate Similarity	NPC217602
0.8176	Intermediate Similarity	NPC317900
0.8176	Intermediate Similarity	NPC476404
0.8176	Intermediate Similarity	NPC473282
0.8176	Intermediate Similarity	NPC232996
0.8176	Intermediate Similarity	NPC104380
0.817	Intermediate Similarity	NPC160777
0.817	Intermediate Similarity	NPC73416
0.817	Intermediate Similarity	NPC28632
0.8165	Intermediate Similarity	NPC478133
0.8158	Intermediate Similarity	NPC238629
0.8151	Intermediate Similarity	NPC242358
0.8151	Intermediate Similarity	NPC246693
0.8151	Intermediate Similarity	NPC110609
0.8141	Intermediate Similarity	NPC280295
0.8137	Intermediate Similarity	NPC478134
0.8133	Intermediate Similarity	NPC216312
0.8133	Intermediate Similarity	NPC477408
0.8133	Intermediate Similarity	NPC299405
0.8133	Intermediate Similarity	NPC256463
0.8133	Intermediate Similarity	NPC476477
0.8133	Intermediate Similarity	NPC306835
0.8133	Intermediate Similarity	NPC111422
0.8133	Intermediate Similarity	NPC29771
0.8133	Intermediate Similarity	NPC471602
0.8129	Intermediate Similarity	NPC46549
0.8129	Intermediate Similarity	NPC264229
0.8121	Intermediate Similarity	NPC315306
0.8121	Intermediate Similarity	NPC313717
0.8113	Intermediate Similarity	NPC478223
0.811	Intermediate Similarity	NPC283041
0.8105	Intermediate Similarity	NPC103910
0.8101	Intermediate Similarity	NPC125487
0.8101	Intermediate Similarity	NPC312482
0.8101	Intermediate Similarity	NPC281703
0.8098	Intermediate Similarity	NPC314653
0.8098	Intermediate Similarity	NPC316262
0.8098	Intermediate Similarity	NPC191930
0.8092	Intermediate Similarity	NPC469855
0.8092	Intermediate Similarity	NPC314271
0.8092	Intermediate Similarity	NPC471972
0.8092	Intermediate Similarity	NPC30846
0.8092	Intermediate Similarity	NPC471971
0.8079	Intermediate Similarity	NPC42262
0.8079	Intermediate Similarity	NPC37992
0.8079	Intermediate Similarity	NPC241349
0.8079	Intermediate Similarity	NPC220496
0.8079	Intermediate Similarity	NPC147542
0.8079	Intermediate Similarity	NPC32749
0.8079	Intermediate Similarity	NPC327916
0.8077	Intermediate Similarity	NPC9099
0.8075	Intermediate Similarity	NPC472961
0.8075	Intermediate Similarity	NPC472962
0.8069	Intermediate Similarity	NPC278928
0.8067	Intermediate Similarity	NPC141368
0.8067	Intermediate Similarity	NPC475757
0.8067	Intermediate Similarity	NPC61590
0.8067	Intermediate Similarity	NPC112135
0.8067	Intermediate Similarity	NPC474640
0.8067	Intermediate Similarity	NPC325625
0.8065	Intermediate Similarity	NPC5568
0.8065	Intermediate Similarity	NPC58373
0.8063	Intermediate Similarity	NPC472889
0.8059	Intermediate Similarity	NPC182693
0.8054	Intermediate Similarity	NPC7464
0.8052	Intermediate Similarity	NPC478160
0.8052	Intermediate Similarity	NPC474309
0.8052	Intermediate Similarity	NPC258856
0.805	Intermediate Similarity	NPC471456
0.805	Intermediate Similarity	NPC314257
0.8049	Intermediate Similarity	NPC477517
0.8049	Intermediate Similarity	NPC20237
0.8039	Intermediate Similarity	NPC199936
0.8039	Intermediate Similarity	NPC21873
0.8038	Intermediate Similarity	NPC180388
0.8038	Intermediate Similarity	NPC115249
0.8038	Intermediate Similarity	NPC312338
0.8038	Intermediate Similarity	NPC149889
0.8037	Intermediate Similarity	NPC472281
0.8037	Intermediate Similarity	NPC249181
0.8037	Intermediate Similarity	NPC205265
0.8026	Intermediate Similarity	NPC472904
0.8026	Intermediate Similarity	NPC257003
0.8026	Intermediate Similarity	NPC471444
0.8026	Intermediate Similarity	NPC283292
0.8026	Intermediate Similarity	NPC110810
0.8025	Intermediate Similarity	NPC187354
0.8025	Intermediate Similarity	NPC117985
0.8025	Intermediate Similarity	NPC31132
0.8013	Intermediate Similarity	NPC142846
0.8013	Intermediate Similarity	NPC295339
0.8012	Intermediate Similarity	NPC245891
0.8012	Intermediate Similarity	NPC104876
0.8	Intermediate Similarity	NPC229264
0.8	Intermediate Similarity	NPC85734
0.8	Intermediate Similarity	NPC170742
0.8	Intermediate Similarity	NPC234175
0.8	Intermediate Similarity	NPC472134
0.8	Intermediate Similarity	NPC186392
0.8	Intermediate Similarity	NPC290030
0.8	Intermediate Similarity	NPC95715
0.8	Intermediate Similarity	NPC32058
0.8	Intermediate Similarity	NPC471970
0.7988	Intermediate Similarity	NPC473286
0.7988	Intermediate Similarity	NPC470735
0.7988	Intermediate Similarity	NPC329647
0.7988	Intermediate Similarity	NPC472277
0.7988	Intermediate Similarity	NPC472049
0.7987	Intermediate Similarity	NPC469854
0.7987	Intermediate Similarity	NPC8493
0.7987	Intermediate Similarity	NPC137301
0.7987	Intermediate Similarity	NPC155686
0.7987	Intermediate Similarity	NPC89664
0.7987	Intermediate Similarity	NPC145301
0.7987	Intermediate Similarity	NPC477048
0.7987	Intermediate Similarity	NPC475201
0.7987	Intermediate Similarity	NPC294679
0.7987	Intermediate Similarity	NPC107109
0.7987	Intermediate Similarity	NPC274085
0.7987	Intermediate Similarity	NPC469856
0.7987	Intermediate Similarity	NPC244691
0.7987	Intermediate Similarity	NPC144247

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 NPC476821 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	910
0.2-0.3	1748
0.3-0.4	2860
0.4-0.5	1869
0.5-0.6	994
0.6-0.7	386
0.7-0.8	64
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8176	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD943	Approved
0.7888	Intermediate Similarity	NPD3882	Suspended
0.7793	Intermediate Similarity	NPD1470	Approved
0.7764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1934	Approved
0.7697	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1512	Approved
0.7595	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1511	Approved
0.7517	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7456	Intermediate Similarity	NPD6166	Phase 2
0.7456	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6232	Discontinued
0.7439	Intermediate Similarity	NPD2801	Approved
0.7412	Intermediate Similarity	NPD7473	Discontinued
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2800	Approved
0.7375	Intermediate Similarity	NPD2534	Approved
0.7375	Intermediate Similarity	NPD2532	Approved
0.7375	Intermediate Similarity	NPD2533	Approved
0.7368	Intermediate Similarity	NPD3818	Discontinued
0.7362	Intermediate Similarity	NPD6599	Discontinued
0.7358	Intermediate Similarity	NPD3300	Phase 2
0.7342	Intermediate Similarity	NPD8166	Discontinued
0.7325	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7075	Discontinued
0.7301	Intermediate Similarity	NPD3226	Approved
0.7296	Intermediate Similarity	NPD6190	Approved
0.7289	Intermediate Similarity	NPD3817	Phase 2
0.7278	Intermediate Similarity	NPD1247	Approved
0.7267	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1471	Phase 3
0.7256	Intermediate Similarity	NPD4380	Phase 2
0.7244	Intermediate Similarity	NPD1510	Phase 2
0.7241	Intermediate Similarity	NPD6797	Phase 2
0.7233	Intermediate Similarity	NPD4628	Phase 3
0.7229	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1607	Approved
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD9494	Approved
0.7219	Intermediate Similarity	NPD5494	Approved
0.7215	Intermediate Similarity	NPD1549	Phase 2
0.7208	Intermediate Similarity	NPD1240	Approved
0.72	Intermediate Similarity	NPD7251	Discontinued
0.7191	Intermediate Similarity	NPD8434	Phase 2
0.7191	Intermediate Similarity	NPD8150	Discontinued
0.7176	Intermediate Similarity	NPD6959	Discontinued
0.7169	Intermediate Similarity	NPD6801	Discontinued
0.716	Intermediate Similarity	NPD919	Approved
0.7159	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7819	Suspended
0.7126	Intermediate Similarity	NPD1465	Phase 2
0.7114	Intermediate Similarity	NPD9269	Phase 2
0.7099	Intermediate Similarity	NPD6799	Approved
0.7099	Intermediate Similarity	NPD7390	Discontinued
0.7086	Intermediate Similarity	NPD7074	Phase 3
0.7069	Intermediate Similarity	NPD3751	Discontinued
0.7062	Intermediate Similarity	NPD7808	Phase 3
0.7044	Intermediate Similarity	NPD2346	Discontinued
0.7029	Intermediate Similarity	NPD7054	Approved
0.7029	Intermediate Similarity	NPD5844	Phase 1
0.7027	Intermediate Similarity	NPD2932	Approved
0.7007	Intermediate Similarity	NPD9545	Approved
0.6994	Remote Similarity	NPD3926	Phase 2
0.6989	Remote Similarity	NPD7472	Approved
0.6981	Remote Similarity	NPD5406	Approved
0.6981	Remote Similarity	NPD5404	Approved
0.6981	Remote Similarity	NPD5405	Approved
0.6981	Remote Similarity	NPD5408	Approved
0.6981	Remote Similarity	NPD2935	Discontinued
0.6975	Remote Similarity	NPD2309	Approved
0.6968	Remote Similarity	NPD3764	Approved
0.6959	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD447	Suspended
0.6932	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3019	Approved
0.6901	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6651	Approved
0.6882	Remote Similarity	NPD5402	Approved
0.6882	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2796	Approved
0.6867	Remote Similarity	NPD920	Approved
0.6865	Remote Similarity	NPD6534	Approved
0.6865	Remote Similarity	NPD6535	Approved
0.6862	Remote Similarity	NPD6782	Approved
0.6862	Remote Similarity	NPD6780	Approved
0.6862	Remote Similarity	NPD6778	Approved
0.6862	Remote Similarity	NPD6777	Approved
0.6862	Remote Similarity	NPD6781	Approved
0.6862	Remote Similarity	NPD6779	Approved
0.6862	Remote Similarity	NPD6776	Approved
0.686	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6234	Discontinued
0.6852	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9268	Approved
0.6842	Remote Similarity	NPD7435	Discontinued
0.6839	Remote Similarity	NPD5711	Approved
0.6839	Remote Similarity	NPD5710	Approved
0.6833	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6559	Discontinued
0.6815	Remote Similarity	NPD6663	Approved
0.6813	Remote Similarity	NPD2799	Discontinued
0.681	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3750	Approved
0.6802	Remote Similarity	NPD3749	Approved
0.68	Remote Similarity	NPD7907	Approved
0.68	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3057	Approved
0.6788	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5026	Approved
0.6778	Remote Similarity	NPD4954	Approved
0.6778	Remote Similarity	NPD36	Approved
0.6778	Remote Similarity	NPD5028	Approved
0.6778	Remote Similarity	NPD4955	Approved
0.6778	Remote Similarity	NPD5034	Approved
0.6774	Remote Similarity	NPD5736	Approved
0.6755	Remote Similarity	NPD7700	Phase 2
0.6755	Remote Similarity	NPD7699	Phase 2
0.6753	Remote Similarity	NPD1164	Approved
0.6747	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.674	Remote Similarity	NPD8313	Approved
0.674	Remote Similarity	NPD8312	Approved
0.6737	Remote Similarity	NPD2493	Approved
0.6737	Remote Similarity	NPD2494	Approved
0.6727	Remote Similarity	NPD7236	Approved
0.6722	Remote Similarity	NPD5030	Phase 2
0.6721	Remote Similarity	NPD5038	Approved
0.6721	Remote Similarity	NPD5037	Approved
0.6719	Remote Similarity	NPD8320	Phase 1
0.6719	Remote Similarity	NPD8319	Approved
0.6707	Remote Similarity	NPD6273	Approved
0.6706	Remote Similarity	NPD7411	Suspended
0.6703	Remote Similarity	NPD2490	Approved
0.6703	Remote Similarity	NPD2488	Approved
0.6702	Remote Similarity	NPD2491	Approved
0.6702	Remote Similarity	NPD3533	Approved
0.6702	Remote Similarity	NPD2972	Approved
0.67	Remote Similarity	NPD4665	Approved
0.67	Remote Similarity	NPD4111	Phase 1
0.6686	Remote Similarity	NPD8127	Discontinued
0.6686	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD37	Approved
0.6667	Remote Similarity	NPD5036	Approved
0.665	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3450	Approved
0.6649	Remote Similarity	NPD3452	Approved
0.6648	Remote Similarity	NPD3787	Discontinued
0.6647	Remote Similarity	NPD4965	Approved
0.6647	Remote Similarity	NPD5401	Approved
0.6647	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4966	Approved
0.6647	Remote Similarity	NPD4967	Phase 2
0.6646	Remote Similarity	NPD2313	Discontinued
0.6645	Remote Similarity	NPD3094	Phase 2
0.6644	Remote Similarity	NPD9493	Approved
0.6633	Remote Similarity	NPD7874	Approved
0.6633	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7870	Phase 2
0.6632	Remote Similarity	NPD4583	Approved
0.6632	Remote Similarity	NPD4582	Approved
0.6632	Remote Similarity	NPD7871	Phase 2
0.663	Remote Similarity	NPD7685	Pre-registration
0.663	Remote Similarity	NPD5027	Approved
0.663	Remote Similarity	NPD5031	Approved
0.663	Remote Similarity	NPD5029	Approved
0.6628	Remote Similarity	NPD5760	Phase 2
0.6628	Remote Similarity	NPD5761	Phase 2
0.6625	Remote Similarity	NPD6355	Discontinued
0.6623	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7701	Phase 2
0.6615	Remote Similarity	NPD3448	Approved
0.661	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7003	Approved
0.6606	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3092	Approved
0.6601	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD7228	Approved
0.6581	Remote Similarity	NPD1876	Approved
0.658	Remote Similarity	NPD4004	Approved
0.658	Remote Similarity	NPD4002	Approved
0.6573	Remote Similarity	NPD7852	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