NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.08
Volume:	197.524
LogP:	0.711
LogD:	0.86
LogS:	-1.973
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	2.712
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.571
MDCK Permeability:	1.965371484402567e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.52
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.418

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.953
Plasma Protein Binding (PPB):	34.57921600341797%
Volume Distribution (VD):	0.981
Pgp-substrate:	57.652557373046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.527
CYP1A2-substrate:	0.906
CYP2C19-inhibitor:	0.18
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.768
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.491

ADMET: Excretion

Clearance (CL):	7.209
Half-life (T1/2):	0.578

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.185
AMES Toxicity:	0.51
Rat Oral Acute Toxicity:	0.595
Maximum Recommended Daily Dose:	0.51
Skin Sensitization:	0.207
Carcinogencity:	0.608
Eye Corrosion:	0.006
Eye Irritation:	0.763
Respiratory Toxicity:	0.528

Download Data

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

Natural Product: NPC470841

Natural Product ID:	NPC470841
*Common Name:**	Nodulisporone
IUPAC Name:	4-hydroxy-8-methoxy-3,4-dihydro-2H-naphthalen-1-one
Synonyms:	nodulisporone
Standard InCHIKey:	YVFDRXJKRIDQPY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H12O3/c1-14-10-4-2-3-7-8(12)5-6-9(13)11(7)10/h2-4,8,12H,5-6H2,1H3
SMILES:	COc1cccc2c1C(=O)CCC2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226407
PubChem CID:	44423671
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12270179]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542359]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17363259]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25978520]

☑ 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	6

Activity Type	# Activity
Individual Protein	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	>	1000000.0	nM	PMID[487685]
NPT4232	Individual Protein	DNA polymerase delta subunit 1	Homo sapiens	IC50	>	1000000.0	nM	PMID[487685]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	IC50	=	82000.0	nM	PMID[487685]
NPT2	Others	Unspecified		IC50	>	1000000.0	nM	PMID[487685]

☑ 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 NPC470841 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	292
0.1-0.2	1418
0.2-0.3	3570
0.3-0.4	9487
0.4-0.5	9302
0.5-0.6	3988
0.6-0.7	8775
0.7-0.8	5504
0.8-0.85	317
0.85-0.9	33
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9174	High Similarity	NPC473662
0.9174	High Similarity	NPC7151
0.9174	High Similarity	NPC216297
0.896	High Similarity	NPC234890
0.896	High Similarity	NPC74507
0.8952	High Similarity	NPC217756
0.8947	High Similarity	NPC477408
0.8915	High Similarity	NPC205360
0.888	High Similarity	NPC182646
0.8846	High Similarity	NPC470160
0.8846	High Similarity	NPC477406
0.881	High Similarity	NPC4012
0.881	High Similarity	NPC152525
0.881	High Similarity	NPC68756
0.8788	High Similarity	NPC22222
0.8788	High Similarity	NPC281513
0.8769	High Similarity	NPC477412
0.875	High Similarity	NPC45537
0.8722	High Similarity	NPC141934
0.8623	High Similarity	NPC477409
0.8613	High Similarity	NPC329493
0.8603	High Similarity	NPC477537
0.8603	High Similarity	NPC477535
0.8571	High Similarity	NPC478018
0.855	High Similarity	NPC278787
0.855	High Similarity	NPC7569
0.8548	High Similarity	NPC171023
0.854	High Similarity	NPC124365
0.8538	High Similarity	NPC767
0.8538	High Similarity	NPC247250
0.8529	High Similarity	NPC1268
0.8527	High Similarity	NPC51037
0.8516	High Similarity	NPC91475
0.8516	High Similarity	NPC265910
0.8504	High Similarity	NPC46634
0.85	High Similarity	NPC300540
0.8489	Intermediate Similarity	NPC274085
0.8489	Intermediate Similarity	NPC89664
0.8485	Intermediate Similarity	NPC7012
0.8485	Intermediate Similarity	NPC141549
0.848	Intermediate Similarity	NPC201284
0.8473	Intermediate Similarity	NPC57552
0.8468	Intermediate Similarity	NPC240664
0.8462	Intermediate Similarity	NPC71525
0.8462	Intermediate Similarity	NPC298884
0.845	Intermediate Similarity	NPC224657
0.8444	Intermediate Similarity	NPC232996
0.8443	Intermediate Similarity	NPC279916
0.844	Intermediate Similarity	NPC71055
0.8433	Intermediate Similarity	NPC274876
0.8429	Intermediate Similarity	NPC478019
0.8413	Intermediate Similarity	NPC206778
0.8413	Intermediate Similarity	NPC285829
0.8409	Intermediate Similarity	NPC473271
0.84	Intermediate Similarity	NPC41567
0.8397	Intermediate Similarity	NPC237225
0.8387	Intermediate Similarity	NPC108288
0.8387	Intermediate Similarity	NPC477453
0.8385	Intermediate Similarity	NPC474264
0.8374	Intermediate Similarity	NPC470837
0.8372	Intermediate Similarity	NPC56332
0.8372	Intermediate Similarity	NPC470163
0.8372	Intermediate Similarity	NPC470162
0.8358	Intermediate Similarity	NPC477536
0.8346	Intermediate Similarity	NPC214702
0.8346	Intermediate Similarity	NPC470831
0.8345	Intermediate Similarity	NPC69755
0.8345	Intermediate Similarity	NPC49108
0.8333	Intermediate Similarity	NPC261759
0.8333	Intermediate Similarity	NPC473499
0.8321	Intermediate Similarity	NPC181715
0.8321	Intermediate Similarity	NPC126739
0.8321	Intermediate Similarity	NPC197666
0.8321	Intermediate Similarity	NPC98395
0.8308	Intermediate Similarity	NPC4164
0.8306	Intermediate Similarity	NPC240163
0.8296	Intermediate Similarity	NPC1249
0.8296	Intermediate Similarity	NPC474097
0.8295	Intermediate Similarity	NPC93730
0.8293	Intermediate Similarity	NPC53953
0.8286	Intermediate Similarity	NPC158871
0.8284	Intermediate Similarity	NPC242358
0.8284	Intermediate Similarity	NPC474340
0.8284	Intermediate Similarity	NPC118253
0.8284	Intermediate Similarity	NPC110609
0.8284	Intermediate Similarity	NPC246693
0.8284	Intermediate Similarity	NPC17843
0.8281	Intermediate Similarity	NPC314329
0.8276	Intermediate Similarity	NPC474843
0.8273	Intermediate Similarity	NPC84273
0.8271	Intermediate Similarity	NPC475741
0.8271	Intermediate Similarity	NPC199253
0.8271	Intermediate Similarity	NPC136588
0.8271	Intermediate Similarity	NPC147757
0.8268	Intermediate Similarity	NPC470092
0.8258	Intermediate Similarity	NPC165257
0.8252	Intermediate Similarity	NPC5537
0.8252	Intermediate Similarity	NPC153417
0.8248	Intermediate Similarity	NPC477534
0.8235	Intermediate Similarity	NPC142027
0.8235	Intermediate Similarity	NPC27407
0.8235	Intermediate Similarity	NPC298900
0.8231	Intermediate Similarity	NPC193805
0.8231	Intermediate Similarity	NPC310540
0.8227	Intermediate Similarity	NPC475201
0.8222	Intermediate Similarity	NPC43627
0.8222	Intermediate Similarity	NPC314048
0.8217	Intermediate Similarity	NPC300274
0.8217	Intermediate Similarity	NPC307174
0.8214	Intermediate Similarity	NPC474385
0.8207	Intermediate Similarity	NPC39819
0.8189	Intermediate Similarity	NPC232178
0.8188	Intermediate Similarity	NPC173980
0.8182	Intermediate Similarity	NPC472036
0.8175	Intermediate Similarity	NPC125252
0.8175	Intermediate Similarity	NPC472881
0.8175	Intermediate Similarity	NPC269414
0.8175	Intermediate Similarity	NPC242712
0.8175	Intermediate Similarity	NPC324929
0.8169	Intermediate Similarity	NPC73416
0.8169	Intermediate Similarity	NPC160777
0.8168	Intermediate Similarity	NPC167055
0.8168	Intermediate Similarity	NPC240744
0.816	Intermediate Similarity	NPC161304
0.8156	Intermediate Similarity	NPC476473
0.8156	Intermediate Similarity	NPC3732
0.8156	Intermediate Similarity	NPC51106
0.8156	Intermediate Similarity	NPC472006
0.8156	Intermediate Similarity	NPC53016
0.8156	Intermediate Similarity	NPC469542
0.8154	Intermediate Similarity	NPC375356
0.8151	Intermediate Similarity	NPC470340
0.8151	Intermediate Similarity	NPC268992
0.8151	Intermediate Similarity	NPC51824
0.8151	Intermediate Similarity	NPC473967
0.8151	Intermediate Similarity	NPC113608
0.8151	Intermediate Similarity	NPC470338
0.8151	Intermediate Similarity	NPC470337
0.8151	Intermediate Similarity	NPC281272
0.8148	Intermediate Similarity	NPC50763
0.8148	Intermediate Similarity	NPC478190
0.8148	Intermediate Similarity	NPC70622
0.8143	Intermediate Similarity	NPC130485
0.8143	Intermediate Similarity	NPC90411
0.8143	Intermediate Similarity	NPC475730
0.8143	Intermediate Similarity	NPC145673
0.8138	Intermediate Similarity	NPC255641
0.8138	Intermediate Similarity	NPC147735
0.8138	Intermediate Similarity	NPC202595
0.8138	Intermediate Similarity	NPC290954
0.8134	Intermediate Similarity	NPC198305
0.813	Intermediate Similarity	NPC54626
0.8129	Intermediate Similarity	NPC476477
0.8129	Intermediate Similarity	NPC268691
0.8129	Intermediate Similarity	NPC471602
0.8129	Intermediate Similarity	NPC111422
0.8129	Intermediate Similarity	NPC256463
0.8129	Intermediate Similarity	NPC216312
0.8129	Intermediate Similarity	NPC268052
0.8129	Intermediate Similarity	NPC29771
0.8129	Intermediate Similarity	NPC306835
0.8129	Intermediate Similarity	NPC299405
0.8125	Intermediate Similarity	NPC216624
0.8116	Intermediate Similarity	NPC284184
0.8116	Intermediate Similarity	NPC472367
0.8116	Intermediate Similarity	NPC472364
0.8116	Intermediate Similarity	NPC135837
0.8116	Intermediate Similarity	NPC305060
0.8116	Intermediate Similarity	NPC476333
0.8116	Intermediate Similarity	NPC473391
0.8116	Intermediate Similarity	NPC301341
0.8112	Intermediate Similarity	NPC107625
0.8112	Intermediate Similarity	NPC32058
0.8112	Intermediate Similarity	NPC472033
0.8112	Intermediate Similarity	NPC85734
0.811	Intermediate Similarity	NPC32298
0.8108	Intermediate Similarity	NPC478223
0.8106	Intermediate Similarity	NPC474737
0.8106	Intermediate Similarity	NPC49647
0.8106	Intermediate Similarity	NPC96915
0.8106	Intermediate Similarity	NPC3224
0.8106	Intermediate Similarity	NPC306765
0.8106	Intermediate Similarity	NPC295202
0.8106	Intermediate Similarity	NPC136342
0.8106	Intermediate Similarity	NPC177925
0.8106	Intermediate Similarity	NPC227741
0.8102	Intermediate Similarity	NPC470844
0.8102	Intermediate Similarity	NPC180905
0.8102	Intermediate Similarity	NPC182496
0.8099	Intermediate Similarity	NPC469385
0.8099	Intermediate Similarity	NPC86373
0.8099	Intermediate Similarity	NPC277426
0.8099	Intermediate Similarity	NPC211439
0.8099	Intermediate Similarity	NPC210425
0.8099	Intermediate Similarity	NPC306816
0.8099	Intermediate Similarity	NPC19896
0.8099	Intermediate Similarity	NPC280404
0.8095	Intermediate Similarity	NPC474000
0.8095	Intermediate Similarity	NPC135522
0.8092	Intermediate Similarity	NPC30216

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 NPC470841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	943
0.2-0.3	1422
0.3-0.4	2506
0.4-0.5	2003
0.5-0.6	1260
0.6-0.7	596
0.7-0.8	135
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8387	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD2346	Discontinued
0.8281	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD2798	Approved
0.814	Intermediate Similarity	NPD1201	Approved
0.8116	Intermediate Similarity	NPD2935	Discontinued
0.803	Intermediate Similarity	NPD1470	Approved
0.8015	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2313	Discontinued
0.7956	Intermediate Similarity	NPD447	Suspended
0.7953	Intermediate Similarity	NPD9493	Approved
0.7945	Intermediate Similarity	NPD3226	Approved
0.7939	Intermediate Similarity	NPD9717	Approved
0.7929	Intermediate Similarity	NPD2344	Approved
0.7914	Intermediate Similarity	NPD1510	Phase 2
0.7914	Intermediate Similarity	NPD2799	Discontinued
0.7899	Intermediate Similarity	NPD1607	Approved
0.7895	Intermediate Similarity	NPD1203	Approved
0.7887	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1876	Approved
0.782	Intermediate Similarity	NPD1283	Approved
0.7801	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6844	Discontinued
0.7769	Intermediate Similarity	NPD1651	Approved
0.7746	Intermediate Similarity	NPD1549	Phase 2
0.7737	Intermediate Similarity	NPD411	Approved
0.7721	Intermediate Similarity	NPD6832	Phase 2
0.7717	Intermediate Similarity	NPD1241	Discontinued
0.7708	Intermediate Similarity	NPD2309	Approved
0.7703	Intermediate Similarity	NPD2651	Approved
0.7703	Intermediate Similarity	NPD2649	Approved
0.7676	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1934	Approved
0.7647	Intermediate Similarity	NPD9494	Approved
0.7616	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7819	Suspended
0.7606	Intermediate Similarity	NPD2796	Approved
0.7606	Intermediate Similarity	NPD1551	Phase 2
0.7603	Intermediate Similarity	NPD1511	Approved
0.7594	Intermediate Similarity	NPD1281	Approved
0.7584	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4626	Approved
0.7574	Intermediate Similarity	NPD1019	Discontinued
0.7566	Intermediate Similarity	NPD5402	Approved
0.7552	Intermediate Similarity	NPD1471	Phase 3
0.7551	Intermediate Similarity	NPD2532	Approved
0.7551	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2533	Approved
0.7551	Intermediate Similarity	NPD2534	Approved
0.7537	Intermediate Similarity	NPD3972	Approved
0.7537	Intermediate Similarity	NPD1608	Approved
0.7533	Intermediate Similarity	NPD4380	Phase 2
0.7517	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD1512	Approved
0.7436	Intermediate Similarity	NPD6959	Discontinued
0.7432	Intermediate Similarity	NPD4661	Approved
0.7432	Intermediate Similarity	NPD4662	Approved
0.7413	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3882	Suspended
0.7397	Intermediate Similarity	NPD4628	Phase 3
0.7397	Intermediate Similarity	NPD3750	Approved
0.7389	Intermediate Similarity	NPD6232	Discontinued
0.7388	Intermediate Similarity	NPD3496	Discontinued
0.7381	Intermediate Similarity	NPD9264	Approved
0.7381	Intermediate Similarity	NPD9263	Approved
0.7381	Intermediate Similarity	NPD9267	Approved
0.7368	Intermediate Similarity	NPD5691	Approved
0.7358	Intermediate Similarity	NPD7473	Discontinued
0.7357	Intermediate Similarity	NPD3268	Approved
0.7338	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5403	Approved
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD709	Approved
0.7323	Intermediate Similarity	NPD9266	Approved
0.7323	Intermediate Similarity	NPD74	Approved
0.7319	Intermediate Similarity	NPD5647	Approved
0.7315	Intermediate Similarity	NPD5401	Approved
0.7313	Intermediate Similarity	NPD1778	Approved
0.7313	Intermediate Similarity	NPD17	Approved
0.7296	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6166	Phase 2
0.7293	Intermediate Similarity	NPD9545	Approved
0.7292	Intermediate Similarity	NPD4308	Phase 3
0.7292	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD1237	Approved
0.7256	Intermediate Similarity	NPD8312	Approved
0.7256	Intermediate Similarity	NPD8313	Approved
0.7254	Intermediate Similarity	NPD2979	Phase 3
0.7254	Intermediate Similarity	NPD943	Approved
0.7248	Intermediate Similarity	NPD6799	Approved
0.7246	Intermediate Similarity	NPD1164	Approved
0.7244	Intermediate Similarity	NPD290	Approved
0.7244	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4476	Approved
0.7241	Intermediate Similarity	NPD4477	Approved
0.7239	Intermediate Similarity	NPD5585	Approved
0.7234	Intermediate Similarity	NPD3764	Approved
0.7226	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3817	Phase 2
0.7211	Intermediate Similarity	NPD2800	Approved
0.7205	Intermediate Similarity	NPD3818	Discontinued
0.7203	Intermediate Similarity	NPD1933	Approved
0.7203	Intermediate Similarity	NPD6355	Discontinued
0.7197	Intermediate Similarity	NPD6671	Approved
0.7172	Intermediate Similarity	NPD3748	Approved
0.7172	Intermediate Similarity	NPD7033	Discontinued
0.7165	Intermediate Similarity	NPD968	Approved
0.7164	Intermediate Similarity	NPD1894	Discontinued
0.7161	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7054	Approved
0.7154	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2232	Approved
0.7153	Intermediate Similarity	NPD2233	Approved
0.7153	Intermediate Similarity	NPD2230	Approved
0.7153	Intermediate Similarity	NPD1481	Phase 2
0.7152	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD7411	Suspended
0.7143	Intermediate Similarity	NPD164	Approved
0.7134	Intermediate Similarity	NPD7075	Discontinued
0.7134	Intermediate Similarity	NPD3749	Approved
0.7133	Intermediate Similarity	NPD4060	Phase 1
0.7124	Intermediate Similarity	NPD7458	Discontinued
0.7123	Intermediate Similarity	NPD6099	Approved
0.7123	Intermediate Similarity	NPD6100	Approved
0.7122	Intermediate Similarity	NPD3266	Approved
0.7122	Intermediate Similarity	NPD3267	Approved
0.7117	Intermediate Similarity	NPD7074	Phase 3
0.7117	Intermediate Similarity	NPD7472	Approved
0.7115	Intermediate Similarity	NPD2296	Approved
0.7113	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6798	Discontinued
0.7099	Intermediate Similarity	NPD3751	Discontinued
0.7097	Intermediate Similarity	NPD6801	Discontinued
0.709	Intermediate Similarity	NPD5536	Phase 2
0.7086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1611	Approved
0.708	Intermediate Similarity	NPD1535	Discovery
0.7078	Intermediate Similarity	NPD6599	Discontinued
0.7077	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6797	Phase 2
0.707	Intermediate Similarity	NPD7768	Phase 2
0.7067	Intermediate Similarity	NPD3300	Phase 2
0.7063	Intermediate Similarity	NPD9261	Approved
0.7059	Intermediate Similarity	NPD3019	Approved
0.7059	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2932	Approved
0.7055	Intermediate Similarity	NPD5844	Phase 1
0.7054	Intermediate Similarity	NPD2182	Approved
0.7041	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6653	Approved
0.703	Intermediate Similarity	NPD7251	Discontinued
0.703	Intermediate Similarity	NPD6559	Discontinued
0.7029	Intermediate Similarity	NPD2235	Phase 2
0.7029	Intermediate Similarity	NPD2231	Phase 2
0.7027	Intermediate Similarity	NPD2424	Discontinued
0.7023	Intermediate Similarity	NPD228	Approved
0.7021	Intermediate Similarity	NPD2861	Phase 2
0.702	Intermediate Similarity	NPD7390	Discontinued
0.7014	Intermediate Similarity	NPD2238	Phase 2
0.7014	Intermediate Similarity	NPD4140	Approved
0.7014	Intermediate Similarity	NPD4307	Phase 2
0.7007	Intermediate Similarity	NPD5408	Approved
0.7007	Intermediate Similarity	NPD6032	Approved
0.7007	Intermediate Similarity	NPD2438	Suspended
0.7007	Intermediate Similarity	NPD5404	Approved
0.7007	Intermediate Similarity	NPD5406	Approved
0.7007	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD920	Approved
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9281	Approved
0.6988	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7808	Phase 3
0.6987	Remote Similarity	NPD37	Approved
0.6987	Remote Similarity	NPD6280	Approved
0.6987	Remote Similarity	NPD6279	Approved
0.6978	Remote Similarity	NPD4359	Approved
0.6974	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD230	Phase 1
0.6966	Remote Similarity	NPD4618	Approved
0.6966	Remote Similarity	NPD4622	Approved
0.6962	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6002	Phase 3
0.6959	Remote Similarity	NPD5763	Approved
0.6959	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6005	Phase 3
0.6959	Remote Similarity	NPD6004	Phase 3
0.6959	Remote Similarity	NPD5762	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