NPASS Compound

Structure

NPC278283 OpenBabel07101719242D 24 25 0 0 1 0 0 0 0 0999 V2000 -5.4125 2.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8088 3.8911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2050 3.8911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3838 0.8987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6106 2.5023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4031 2.5023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6013 2.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8044 2.5023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6062 2.0393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0069 2.5023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8088 2.9652 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2050 2.9652 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4630 0.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0025 2.0393 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6062 1.1134 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1566 1.4900 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8044 0.6504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9057 0.1925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0025 1.1134 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4081 0.6504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0359 2.3957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8044 -0.2755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2819 -1.0466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 4 13 2 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 2 1 1 0 0 0 12 3 1 1 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 19 1 6 0 0 0 15 17 1 0 0 0 0 15 20 1 1 0 0 0 16 19 1 6 0 0 0 16 21 1 0 0 0 0 17 19 1 6 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.19
Volume:	353.473
LogP:	2.705
LogD:	1.458
LogS:	-2.394
# Rotatable Bonds:	5
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	5.71
Fsp3:	0.632
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:	-5.17
MDCK Permeability:	1.667141441430431e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.614
Human Intestinal Absorption (HIA):	0.548
20% Bioavailability (F20%):	0.715
30% Bioavailability (F30%):	0.802

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	79.00159454345703%
Volume Distribution (VD):	1.121
Pgp-substrate:	7.1504621505737305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.687
CYP2C9-inhibitor:	0.212
CYP2C9-substrate:	0.24
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.272
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	1.852
Half-life (T1/2):	0.69

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.018
Drug-inuced Liver Injury (DILI):	0.782
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.651
Carcinogencity:	0.002
Eye Corrosion:	0.004
Eye Irritation:	0.083
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC278283

Natural Product ID:	NPC278283
*Common Name:**	Spirolephtoshol
IUPAC Name:	(4R,5R,6R,7R,10R)-10-[(E,3R,5R)-3,5-dimethylhept-1-enyl]-4,6,7-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-8-en-1-one
Synonyms:	spirolephtoshol
Standard InCHIKey:	FCZKZHGNJNETSF-YTZRTTPESA-N
Standard InCHI:	InChI=1S/C19H28O5/c1-5-11(2)10-12(3)6-7-14-8-9-15(20)17(22)19(14)16(21)13(4)24-18(19)23/h6-9,11-12,14-17,20-22H,4-5,10H2,1-3H3/b7-6+/t11-,12+,14-,15-,16+,17+,19+/m1/s1
SMILES:	CC[C@H](C[C@H](/C=C/[C@@H]1C=C[C@H]([C@@H]([C@@]21C(=O)OC(=C)[C@@H]2O)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486248
PubChem CID:	44561069
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001967] Oxolanes

*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
NPO24465	Leptosphaeria doliolum	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18541425]
NPO24465	Leptosphaeria doliolum	Species	Leptosphaeriaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	EC50	=	20.0	ug.mL-1	PMID[478482]

☑ 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 NPC278283 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	164
0.1-0.2	1263
0.2-0.3	5040
0.3-0.4	12950
0.4-0.5	11262
0.5-0.6	8037
0.6-0.7	3619
0.7-0.8	346
0.8-0.85	9
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC32676
0.9277	High Similarity	NPC478112
0.8953	High Similarity	NPC478110
0.8409	Intermediate Similarity	NPC119740
0.8409	Intermediate Similarity	NPC150063
0.8256	Intermediate Similarity	NPC52923
0.8144	Intermediate Similarity	NPC220964
0.8144	Intermediate Similarity	NPC475676
0.8041	Intermediate Similarity	NPC4620
0.8	Intermediate Similarity	NPC137368
0.7935	Intermediate Similarity	NPC9447
0.7912	Intermediate Similarity	NPC87306
0.79	Intermediate Similarity	NPC474664
0.79	Intermediate Similarity	NPC14862
0.79	Intermediate Similarity	NPC233379
0.7857	Intermediate Similarity	NPC474165
0.7857	Intermediate Similarity	NPC69171
0.7826	Intermediate Similarity	NPC473455
0.7822	Intermediate Similarity	NPC15218
0.78	Intermediate Similarity	NPC324327
0.78	Intermediate Similarity	NPC474421
0.78	Intermediate Similarity	NPC326994
0.78	Intermediate Similarity	NPC194620
0.78	Intermediate Similarity	NPC72813
0.7791	Intermediate Similarity	NPC475210
0.7765	Intermediate Similarity	NPC474278
0.7755	Intermediate Similarity	NPC183571
0.7753	Intermediate Similarity	NPC219966
0.7727	Intermediate Similarity	NPC474252
0.7723	Intermediate Similarity	NPC327286
0.7723	Intermediate Similarity	NPC55972
0.7723	Intermediate Similarity	NPC169888
0.77	Intermediate Similarity	NPC9303
0.77	Intermediate Similarity	NPC475802
0.77	Intermediate Similarity	NPC16313
0.7692	Intermediate Similarity	NPC316629
0.7692	Intermediate Similarity	NPC473248
0.7634	Intermediate Similarity	NPC15059
0.7634	Intermediate Similarity	NPC474232
0.7614	Intermediate Similarity	NPC474980
0.7609	Intermediate Similarity	NPC153570
0.7609	Intermediate Similarity	NPC476803
0.7604	Intermediate Similarity	NPC477921
0.76	Intermediate Similarity	NPC146731
0.76	Intermediate Similarity	NPC203659
0.76	Intermediate Similarity	NPC296950
0.7586	Intermediate Similarity	NPC99651
0.7582	Intermediate Similarity	NPC469910
0.7573	Intermediate Similarity	NPC115257
0.7573	Intermediate Similarity	NPC161816
0.7556	Intermediate Similarity	NPC212363
0.7553	Intermediate Similarity	NPC473321
0.7553	Intermediate Similarity	NPC472199
0.75	Intermediate Similarity	NPC477922
0.75	Intermediate Similarity	NPC471142
0.75	Intermediate Similarity	NPC214694
0.75	Intermediate Similarity	NPC110989
0.7476	Intermediate Similarity	NPC475922
0.7474	Intermediate Similarity	NPC475912
0.7473	Intermediate Similarity	NPC21469
0.7471	Intermediate Similarity	NPC11796
0.7471	Intermediate Similarity	NPC218817
0.7447	Intermediate Similarity	NPC313670
0.7447	Intermediate Similarity	NPC473619
0.7426	Intermediate Similarity	NPC258532
0.7419	Intermediate Similarity	NPC473715
0.7419	Intermediate Similarity	NPC309656
0.7416	Intermediate Similarity	NPC297440
0.7412	Intermediate Similarity	NPC474280
0.7404	Intermediate Similarity	NPC235014
0.7404	Intermediate Similarity	NPC5103
0.74	Intermediate Similarity	NPC225353
0.7396	Intermediate Similarity	NPC472198
0.7386	Intermediate Similarity	NPC291260
0.7368	Intermediate Similarity	NPC208839
0.7368	Intermediate Similarity	NPC472197
0.7363	Intermediate Similarity	NPC158756
0.7363	Intermediate Similarity	NPC38569
0.7363	Intermediate Similarity	NPC163615
0.7347	Intermediate Similarity	NPC134454
0.7347	Intermediate Similarity	NPC474194
0.7347	Intermediate Similarity	NPC17326
0.7347	Intermediate Similarity	NPC40812
0.734	Intermediate Similarity	NPC79027
0.7327	Intermediate Similarity	NPC475871
0.7327	Intermediate Similarity	NPC475945
0.7327	Intermediate Similarity	NPC159533
0.7326	Intermediate Similarity	NPC473948
0.732	Intermediate Similarity	NPC270013
0.732	Intermediate Similarity	NPC14961
0.732	Intermediate Similarity	NPC36954
0.7308	Intermediate Similarity	NPC42662
0.73	Intermediate Similarity	NPC469657
0.73	Intermediate Similarity	NPC28304
0.73	Intermediate Similarity	NPC298255
0.73	Intermediate Similarity	NPC244456
0.73	Intermediate Similarity	NPC308824
0.73	Intermediate Similarity	NPC472753
0.7292	Intermediate Similarity	NPC162205
0.7292	Intermediate Similarity	NPC288240
0.7292	Intermediate Similarity	NPC61201
0.7292	Intermediate Similarity	NPC295204
0.7292	Intermediate Similarity	NPC273579
0.729	Intermediate Similarity	NPC117712
0.7283	Intermediate Similarity	NPC470755
0.7283	Intermediate Similarity	NPC155873
0.7282	Intermediate Similarity	NPC230541
0.7273	Intermediate Similarity	NPC127526
0.7273	Intermediate Similarity	NPC124512
0.7273	Intermediate Similarity	NPC278386
0.7273	Intermediate Similarity	NPC222303
0.7273	Intermediate Similarity	NPC159763
0.7273	Intermediate Similarity	NPC83895
0.7273	Intermediate Similarity	NPC187761
0.7273	Intermediate Similarity	NPC471144
0.7263	Intermediate Similarity	NPC214844
0.7263	Intermediate Similarity	NPC475855
0.7255	Intermediate Similarity	NPC472756
0.7253	Intermediate Similarity	NPC69469
0.7253	Intermediate Similarity	NPC116543
0.7245	Intermediate Similarity	NPC473859
0.7245	Intermediate Similarity	NPC469369
0.7245	Intermediate Similarity	NPC54731
0.7245	Intermediate Similarity	NPC469528
0.7245	Intermediate Similarity	NPC11396
0.7245	Intermediate Similarity	NPC306041
0.7245	Intermediate Similarity	NPC21302
0.7245	Intermediate Similarity	NPC241911
0.7234	Intermediate Similarity	NPC475819
0.7234	Intermediate Similarity	NPC476805
0.7234	Intermediate Similarity	NPC87189
0.7234	Intermediate Similarity	NPC228415
0.7228	Intermediate Similarity	NPC235369
0.7228	Intermediate Similarity	NPC474747
0.7228	Intermediate Similarity	NPC250545
0.7228	Intermediate Similarity	NPC13171
0.7228	Intermediate Similarity	NPC261117
0.7228	Intermediate Similarity	NPC195510
0.7228	Intermediate Similarity	NPC310804
0.7228	Intermediate Similarity	NPC472754
0.7222	Intermediate Similarity	NPC52861
0.7216	Intermediate Similarity	NPC81386
0.7216	Intermediate Similarity	NPC2003
0.7216	Intermediate Similarity	NPC25701
0.7216	Intermediate Similarity	NPC474035
0.7212	Intermediate Similarity	NPC264819
0.7212	Intermediate Similarity	NPC94377
0.7212	Intermediate Similarity	NPC308191
0.7204	Intermediate Similarity	NPC477994
0.7204	Intermediate Similarity	NPC477993
0.7204	Intermediate Similarity	NPC477668
0.72	Intermediate Similarity	NPC324667
0.72	Intermediate Similarity	NPC255677
0.72	Intermediate Similarity	NPC306344
0.72	Intermediate Similarity	NPC288876
0.72	Intermediate Similarity	NPC22149
0.72	Intermediate Similarity	NPC475949
0.7196	Intermediate Similarity	NPC469454
0.7196	Intermediate Similarity	NPC469463
0.7196	Intermediate Similarity	NPC469496
0.7191	Intermediate Similarity	NPC86971
0.7191	Intermediate Similarity	NPC321728
0.7188	Intermediate Similarity	NPC476705
0.7188	Intermediate Similarity	NPC184463
0.7188	Intermediate Similarity	NPC30515
0.7188	Intermediate Similarity	NPC230623
0.7184	Intermediate Similarity	NPC179891
0.7174	Intermediate Similarity	NPC476804
0.7174	Intermediate Similarity	NPC295799
0.7172	Intermediate Similarity	NPC266842
0.7172	Intermediate Similarity	NPC205143
0.717	Intermediate Similarity	NPC179798
0.717	Intermediate Similarity	NPC317107
0.717	Intermediate Similarity	NPC304180
0.7158	Intermediate Similarity	NPC473564
0.7158	Intermediate Similarity	NPC474032
0.7158	Intermediate Similarity	NPC133450
0.7157	Intermediate Similarity	NPC156681
0.7157	Intermediate Similarity	NPC472755
0.7156	Intermediate Similarity	NPC470775
0.7156	Intermediate Similarity	NPC469684
0.7156	Intermediate Similarity	NPC176513
0.7143	Intermediate Similarity	NPC304886
0.7143	Intermediate Similarity	NPC475046
0.7143	Intermediate Similarity	NPC472534
0.7143	Intermediate Similarity	NPC475659
0.7143	Intermediate Similarity	NPC143706
0.7143	Intermediate Similarity	NPC310450
0.7143	Intermediate Similarity	NPC474959
0.7143	Intermediate Similarity	NPC11383
0.7143	Intermediate Similarity	NPC141350
0.7143	Intermediate Similarity	NPC107476
0.7129	Intermediate Similarity	NPC474742
0.7129	Intermediate Similarity	NPC97435
0.7128	Intermediate Similarity	NPC477959
0.7128	Intermediate Similarity	NPC86005
0.7128	Intermediate Similarity	NPC179659
0.7128	Intermediate Similarity	NPC23622
0.7128	Intermediate Similarity	NPC472007
0.7128	Intermediate Similarity	NPC475037

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 NPC278283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1866
0.2-0.3	3910
0.3-0.4	2211
0.4-0.5	664
0.5-0.6	281
0.6-0.7	50
0.7-0.8	18
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7778	Intermediate Similarity	NPD4249	Approved
0.7692	Intermediate Similarity	NPD4251	Approved
0.7692	Intermediate Similarity	NPD4250	Approved
0.7553	Intermediate Similarity	NPD7983	Approved
0.7368	Intermediate Similarity	NPD7637	Suspended
0.7303	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4225	Approved
0.7253	Intermediate Similarity	NPD6110	Phase 1
0.7113	Intermediate Similarity	NPD5778	Approved
0.7113	Intermediate Similarity	NPD5779	Approved
0.7111	Intermediate Similarity	NPD4252	Approved
0.7083	Intermediate Similarity	NPD6698	Approved
0.7083	Intermediate Similarity	NPD46	Approved
0.7079	Intermediate Similarity	NPD4271	Approved
0.7079	Intermediate Similarity	NPD4268	Approved
0.7075	Intermediate Similarity	NPD6371	Approved
0.7041	Intermediate Similarity	NPD5282	Discontinued
0.6957	Remote Similarity	NPD4269	Approved
0.6957	Remote Similarity	NPD4270	Approved
0.6923	Remote Similarity	NPD4820	Approved
0.6923	Remote Similarity	NPD4821	Approved
0.6923	Remote Similarity	NPD4819	Approved
0.6923	Remote Similarity	NPD4822	Approved
0.6907	Remote Similarity	NPD5785	Approved
0.6889	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7154	Phase 3
0.6842	Remote Similarity	NPD5786	Approved
0.68	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD8515	Approved
0.6754	Remote Similarity	NPD8517	Approved
0.6754	Remote Similarity	NPD8516	Approved
0.6754	Remote Similarity	NPD8513	Phase 3
0.6737	Remote Similarity	NPD5363	Approved
0.6735	Remote Similarity	NPD7838	Discovery
0.6697	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6602	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6686	Approved
0.6569	Remote Similarity	NPD7839	Suspended
0.6549	Remote Similarity	NPD7115	Discovery
0.6526	Remote Similarity	NPD5362	Discontinued
0.6512	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5344	Discontinued
0.6471	Remote Similarity	NPD8074	Phase 3
0.6465	Remote Similarity	NPD5370	Suspended
0.6465	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6101	Approved
0.6455	Remote Similarity	NPD6421	Discontinued
0.6421	Remote Similarity	NPD5209	Approved
0.6421	Remote Similarity	NPD6435	Approved
0.6396	Remote Similarity	NPD2204	Approved
0.6381	Remote Similarity	NPD7639	Approved
0.6381	Remote Similarity	NPD7640	Approved
0.6354	Remote Similarity	NPD5332	Approved
0.6354	Remote Similarity	NPD5331	Approved
0.6316	Remote Similarity	NPD4790	Discontinued
0.6289	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7638	Approved
0.6275	Remote Similarity	NPD6399	Phase 3
0.6273	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7524	Approved
0.6239	Remote Similarity	NPD6319	Approved
0.6224	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5368	Approved
0.619	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6412	Phase 2
0.6122	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6648	Approved
0.6061	Remote Similarity	NPD1694	Approved
0.6053	Remote Similarity	NPD6053	Discontinued
0.6042	Remote Similarity	NPD7514	Phase 3
0.6042	Remote Similarity	NPD7332	Phase 2
0.6033	Remote Similarity	NPD8341	Approved
0.6033	Remote Similarity	NPD8299	Approved
0.6033	Remote Similarity	NPD8342	Approved
0.6033	Remote Similarity	NPD8340	Approved
0.6033	Remote Similarity	NPD7492	Approved
0.602	Remote Similarity	NPD6695	Phase 3
0.6018	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD7145	Approved
0.5984	Remote Similarity	NPD6616	Approved
0.5983	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.598	Remote Similarity	NPD1695	Approved
0.5979	Remote Similarity	NPD6902	Approved
0.5978	Remote Similarity	NPD4732	Discontinued
0.5966	Remote Similarity	NPD6054	Approved
0.596	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6109	Phase 1
0.595	Remote Similarity	NPD8328	Phase 3
0.5935	Remote Similarity	NPD7078	Approved
0.593	Remote Similarity	NPD368	Approved
0.5929	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6015	Approved
0.5917	Remote Similarity	NPD6016	Approved
0.5917	Remote Similarity	NPD8444	Approved
0.5917	Remote Similarity	NPD7503	Approved
0.5895	Remote Similarity	NPD6925	Approved
0.5895	Remote Similarity	NPD5776	Phase 2
0.5887	Remote Similarity	NPD7736	Approved
0.5868	Remote Similarity	NPD5988	Approved
0.5868	Remote Similarity	NPD6370	Approved
0.5854	Remote Similarity	NPD8273	Phase 1
0.5854	Remote Similarity	NPD8451	Approved
0.5851	Remote Similarity	NPD8264	Approved
0.5851	Remote Similarity	NPD8039	Approved
0.584	Remote Similarity	NPD7319	Approved
0.5833	Remote Similarity	NPD6059	Approved
0.582	Remote Similarity	NPD7642	Approved
0.582	Remote Similarity	NPD7829	Approved
0.582	Remote Similarity	NPD7830	Approved
0.5818	Remote Similarity	NPD7632	Discontinued
0.5806	Remote Similarity	NPD8448	Approved
0.5806	Remote Similarity	NPD8293	Discontinued
0.5804	Remote Similarity	NPD6008	Approved
0.5804	Remote Similarity	NPD5048	Discontinued
0.5795	Remote Similarity	NPD3197	Phase 1
0.5784	Remote Similarity	NPD7750	Discontinued
0.5776	Remote Similarity	NPD8297	Approved
0.5773	Remote Similarity	NPD6929	Approved
0.5758	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD3667	Approved
0.5752	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD5697	Approved
0.5741	Remote Similarity	NPD6084	Phase 2
0.5741	Remote Similarity	NPD7902	Approved
0.5741	Remote Similarity	NPD6083	Phase 2
0.5739	Remote Similarity	NPD4634	Approved
0.5729	Remote Similarity	NPD6932	Approved
0.5729	Remote Similarity	NPD4756	Discovery
0.5726	Remote Similarity	NPD7507	Approved
0.5714	Remote Similarity	NPD6930	Phase 2
0.5714	Remote Similarity	NPD6009	Approved
0.5714	Remote Similarity	NPD6931	Approved
0.5702	Remote Similarity	NPD6881	Approved
0.5702	Remote Similarity	NPD6899	Approved
0.5701	Remote Similarity	NPD5695	Phase 3
0.569	Remote Similarity	NPD6650	Approved
0.569	Remote Similarity	NPD6649	Approved
0.569	Remote Similarity	NPD1719	Phase 1
0.5688	Remote Similarity	NPD5696	Approved
0.567	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD8391	Approved
0.5669	Remote Similarity	NPD8392	Approved
0.5669	Remote Similarity	NPD8390	Approved
0.5667	Remote Similarity	NPD7641	Discontinued
0.5667	Remote Similarity	NPD7327	Approved
0.5667	Remote Similarity	NPD7328	Approved
0.5664	Remote Similarity	NPD6402	Approved
0.5664	Remote Similarity	NPD6675	Approved
0.5664	Remote Similarity	NPD5739	Approved
0.5664	Remote Similarity	NPD7128	Approved
0.5657	Remote Similarity	NPD6898	Phase 1
0.5656	Remote Similarity	NPD6921	Approved
0.5656	Remote Similarity	NPD5983	Phase 2
0.5656	Remote Similarity	NPD8033	Approved
0.5652	Remote Similarity	NPD6012	Approved
0.5652	Remote Similarity	NPD6013	Approved
0.5652	Remote Similarity	NPD6014	Approved
0.5652	Remote Similarity	NPD6373	Approved
0.5652	Remote Similarity	NPD6372	Approved
0.5649	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD4228	Discovery
0.5644	Remote Similarity	NPD4786	Approved
0.5625	Remote Similarity	NPD7260	Phase 2
0.5625	Remote Similarity	NPD6647	Phase 2
0.5625	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.562	Remote Similarity	NPD7516	Approved
0.5614	Remote Similarity	NPD6685	Approved
0.5614	Remote Similarity	NPD5701	Approved
0.5607	Remote Similarity	NPD7748	Approved
0.5603	Remote Similarity	NPD6883	Approved
0.5603	Remote Similarity	NPD7102	Approved
0.5603	Remote Similarity	NPD7290	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