NPASS Compound

Structure

NPC275507 OpenBabel07101719242D 22 23 0 0 1 0 0 0 0 0999 V2000 0.3727 6.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5317 5.0158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2330 1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0454 3.6776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1625 4.6557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6977 3.0085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5806 5.3249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4898 2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4487 2.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -1.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -1.7796 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 2 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 14 19 2 0 0 0 0 15 18 1 0 0 0 0 15 20 2 0 0 0 0 16 18 1 6 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.15
Volume:	322.113
LogP:	2.895
LogD:	1.975
LogS:	-4.363
# Rotatable Bonds:	4
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	4.658
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.753
MDCK Permeability:	2.3667254936299287e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.228
20% Bioavailability (F20%):	0.076
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.336
Plasma Protein Binding (PPB):	90.80140686035156%
Volume Distribution (VD):	0.946
Pgp-substrate:	7.3660993576049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.648
CYP2C19-substrate:	0.605
CYP2C9-inhibitor:	0.262
CYP2C9-substrate:	0.569
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.159
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	5.84
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.83
Drug-inuced Liver Injury (DILI):	0.226
AMES Toxicity:	0.67
Rat Oral Acute Toxicity:	0.768
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.676
Carcinogencity:	0.109
Eye Corrosion:	0.004
Eye Irritation:	0.025
Respiratory Toxicity:	0.748

Download Data

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

Natural Product: NPC275507

Natural Product ID:	NPC275507
*Common Name:**	(+)-Miliusane Viii
IUPAC Name:	(1R,5R)-1-[(1E)-2,6-dimethylhepta-1,5-dienyl]-2-oxaspiro[4.5]dec-7-ene-3,6,9-trione
Synonyms:	(+)-Miliusane VIII
Standard InCHIKey:	NCOZLBGVSVAXKL-MKPVWWQNSA-N
Standard InCHI:	InChI=1S/C18H22O4/c1-12(2)5-4-6-13(3)9-16-18(11-17(21)22-16)10-14(19)7-8-15(18)20/h5,7-9,16H,4,6,10-11H2,1-3H3/b13-9+/t16-,18+/m1/s1
SMILES:	CC(=CCC/C(=C/[C@@H]1[C@@]2(CC(=O)C=CC2=O)CC(=O)O1)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL201579
PubChem CID:	11681021
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO22093	Miliusa sinensis	Species	Annonaceae	Eukaryota	dried leaves, twigs, and flowers	Vietnam	n.a.	PMID[16420055]
NPO22093	Miliusa sinensis	Species	Annonaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	47350.0	nM	PMID[568667]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	=	63580.0	nM	PMID[568667]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	=	33440.0	nM	PMID[568667]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	43380.0	nM	PMID[568667]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	26420.0	nM	PMID[568667]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	>	10900.0	nM	PMID[568667]

☑ 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 NPC275507 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	188
0.1-0.2	1550
0.2-0.3	7866
0.3-0.4	15265
0.4-0.5	9482
0.5-0.6	5895
0.6-0.7	2205
0.7-0.8	232
0.8-0.85	7
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9125	High Similarity	NPC163615
0.9125	High Similarity	NPC38569
0.9012	High Similarity	NPC155873
0.8795	High Similarity	NPC473248
0.869	High Similarity	NPC153570
0.8588	High Similarity	NPC78008
0.8588	High Similarity	NPC87306
0.8488	Intermediate Similarity	NPC473455
0.8111	Intermediate Similarity	NPC214694
0.8049	Intermediate Similarity	NPC473980
0.8049	Intermediate Similarity	NPC473981
0.8023	Intermediate Similarity	NPC279859
0.8023	Intermediate Similarity	NPC38576
0.8	Intermediate Similarity	NPC219966
0.7976	Intermediate Similarity	NPC475690
0.7976	Intermediate Similarity	NPC173609
0.7927	Intermediate Similarity	NPC475699
0.7875	Intermediate Similarity	NPC15499
0.7875	Intermediate Similarity	NPC117746
0.7875	Intermediate Similarity	NPC294434
0.7875	Intermediate Similarity	NPC476355
0.7875	Intermediate Similarity	NPC259599
0.7805	Intermediate Similarity	NPC57744
0.7791	Intermediate Similarity	NPC149869
0.7778	Intermediate Similarity	NPC284185
0.7711	Intermediate Similarity	NPC471220
0.7711	Intermediate Similarity	NPC128276
0.7711	Intermediate Similarity	NPC253749
0.7692	Intermediate Similarity	NPC470256
0.7683	Intermediate Similarity	NPC27205
0.7683	Intermediate Similarity	NPC123360
0.7674	Intermediate Similarity	NPC52923
0.7667	Intermediate Similarity	NPC253144
0.7667	Intermediate Similarity	NPC471818
0.766	Intermediate Similarity	NPC54843
0.7654	Intermediate Similarity	NPC140287
0.7647	Intermediate Similarity	NPC42470
0.7647	Intermediate Similarity	NPC474980
0.7625	Intermediate Similarity	NPC163003
0.7619	Intermediate Similarity	NPC471299
0.7619	Intermediate Similarity	NPC270126
0.7619	Intermediate Similarity	NPC178277
0.7595	Intermediate Similarity	NPC476591
0.7595	Intermediate Similarity	NPC88877
0.759	Intermediate Similarity	NPC187568
0.759	Intermediate Similarity	NPC41780
0.7582	Intermediate Similarity	NPC150978
0.7582	Intermediate Similarity	NPC123177
0.7582	Intermediate Similarity	NPC70595
0.7582	Intermediate Similarity	NPC74103
0.7564	Intermediate Similarity	NPC203335
0.7564	Intermediate Similarity	NPC194871
0.7531	Intermediate Similarity	NPC287878
0.7529	Intermediate Similarity	NPC223904
0.7528	Intermediate Similarity	NPC478144
0.7527	Intermediate Similarity	NPC474490
0.75	Intermediate Similarity	NPC93763
0.75	Intermediate Similarity	NPC21471
0.75	Intermediate Similarity	NPC165383
0.75	Intermediate Similarity	NPC108816
0.75	Intermediate Similarity	NPC177932
0.75	Intermediate Similarity	NPC33570
0.7471	Intermediate Similarity	NPC475947
0.7471	Intermediate Similarity	NPC318468
0.7444	Intermediate Similarity	NPC469653
0.7444	Intermediate Similarity	NPC226863
0.7444	Intermediate Similarity	NPC469631
0.7444	Intermediate Similarity	NPC471047
0.7444	Intermediate Similarity	NPC469628
0.7444	Intermediate Similarity	NPC475906
0.7442	Intermediate Similarity	NPC471325
0.7419	Intermediate Similarity	NPC470697
0.7412	Intermediate Similarity	NPC150646
0.7407	Intermediate Similarity	NPC257618
0.7391	Intermediate Similarity	NPC233437
0.7391	Intermediate Similarity	NPC472705
0.7391	Intermediate Similarity	NPC207641
0.7381	Intermediate Similarity	NPC141789
0.7381	Intermediate Similarity	NPC171204
0.7381	Intermediate Similarity	NPC476028
0.7381	Intermediate Similarity	NPC97516
0.7375	Intermediate Similarity	NPC473603
0.7375	Intermediate Similarity	NPC476059
0.7356	Intermediate Similarity	NPC85772
0.7333	Intermediate Similarity	NPC478145
0.7333	Intermediate Similarity	NPC72513
0.7326	Intermediate Similarity	NPC281132
0.7317	Intermediate Similarity	NPC58956
0.7317	Intermediate Similarity	NPC269206
0.7317	Intermediate Similarity	NPC295633
0.7312	Intermediate Similarity	NPC475302
0.7303	Intermediate Similarity	NPC110405
0.7303	Intermediate Similarity	NPC125290
0.7303	Intermediate Similarity	NPC161957
0.7303	Intermediate Similarity	NPC470755
0.7303	Intermediate Similarity	NPC189311
0.7294	Intermediate Similarity	NPC267231
0.7292	Intermediate Similarity	NPC141191
0.7284	Intermediate Similarity	NPC469660
0.7283	Intermediate Similarity	NPC469372
0.7273	Intermediate Similarity	NPC215294
0.7273	Intermediate Similarity	NPC16488
0.7273	Intermediate Similarity	NPC193198
0.7273	Intermediate Similarity	NPC474658
0.7263	Intermediate Similarity	NPC185553
0.7262	Intermediate Similarity	NPC40353
0.7253	Intermediate Similarity	NPC119740
0.7253	Intermediate Similarity	NPC150063
0.7253	Intermediate Similarity	NPC215831
0.725	Intermediate Similarity	NPC218477
0.7241	Intermediate Similarity	NPC301477
0.7241	Intermediate Similarity	NPC281949
0.7241	Intermediate Similarity	NPC25684
0.7237	Intermediate Similarity	NPC79756
0.7234	Intermediate Similarity	NPC167219
0.7234	Intermediate Similarity	NPC148463
0.7234	Intermediate Similarity	NPC84893
0.7234	Intermediate Similarity	NPC477130
0.7234	Intermediate Similarity	NPC477129
0.7229	Intermediate Similarity	NPC474758
0.7222	Intermediate Similarity	NPC220478
0.7222	Intermediate Similarity	NPC104961
0.7222	Intermediate Similarity	NPC261721
0.7222	Intermediate Similarity	NPC70422
0.7222	Intermediate Similarity	NPC70555
0.7215	Intermediate Similarity	NPC248125
0.7209	Intermediate Similarity	NPC469620
0.7209	Intermediate Similarity	NPC264227
0.7209	Intermediate Similarity	NPC63649
0.7209	Intermediate Similarity	NPC472965
0.7209	Intermediate Similarity	NPC469690
0.7204	Intermediate Similarity	NPC111114
0.7204	Intermediate Similarity	NPC300312
0.7204	Intermediate Similarity	NPC261607
0.7191	Intermediate Similarity	NPC158756
0.7191	Intermediate Similarity	NPC31086
0.7191	Intermediate Similarity	NPC474359
0.7188	Intermediate Similarity	NPC169205
0.7176	Intermediate Similarity	NPC476794
0.7176	Intermediate Similarity	NPC474760
0.7176	Intermediate Similarity	NPC320630
0.7176	Intermediate Similarity	NPC7563
0.7176	Intermediate Similarity	NPC65603
0.7176	Intermediate Similarity	NPC473825
0.7176	Intermediate Similarity	NPC116177
0.7176	Intermediate Similarity	NPC470240
0.7174	Intermediate Similarity	NPC73995
0.7159	Intermediate Similarity	NPC178676
0.7158	Intermediate Similarity	NPC48803
0.7158	Intermediate Similarity	NPC193645
0.7158	Intermediate Similarity	NPC473369
0.7158	Intermediate Similarity	NPC275960
0.7158	Intermediate Similarity	NPC90121
0.7143	Intermediate Similarity	NPC151648
0.7143	Intermediate Similarity	NPC244166
0.7143	Intermediate Similarity	NPC155587
0.7143	Intermediate Similarity	NPC138408
0.7143	Intermediate Similarity	NPC193351
0.7143	Intermediate Similarity	NPC226669
0.7129	Intermediate Similarity	NPC133422
0.7128	Intermediate Similarity	NPC475657
0.7128	Intermediate Similarity	NPC469692
0.7128	Intermediate Similarity	NPC469645
0.7126	Intermediate Similarity	NPC160582
0.7125	Intermediate Similarity	NPC106613
0.7111	Intermediate Similarity	NPC28887
0.7111	Intermediate Similarity	NPC471060
0.7111	Intermediate Similarity	NPC215364
0.7111	Intermediate Similarity	NPC261380
0.7108	Intermediate Similarity	NPC276336
0.7108	Intermediate Similarity	NPC16349
0.7108	Intermediate Similarity	NPC474705
0.7108	Intermediate Similarity	NPC222244
0.71	Intermediate Similarity	NPC472756
0.7097	Intermediate Similarity	NPC145666
0.7097	Intermediate Similarity	NPC152467
0.7097	Intermediate Similarity	NPC51653
0.7097	Intermediate Similarity	NPC212679
0.7097	Intermediate Similarity	NPC469595
0.7097	Intermediate Similarity	NPC220454
0.7097	Intermediate Similarity	NPC51486
0.7093	Intermediate Similarity	NPC279532
0.7093	Intermediate Similarity	NPC127526
0.7089	Intermediate Similarity	NPC470688
0.7083	Intermediate Similarity	NPC476275
0.7083	Intermediate Similarity	NPC21302
0.7083	Intermediate Similarity	NPC11396
0.7079	Intermediate Similarity	NPC22611
0.7079	Intermediate Similarity	NPC40746
0.7079	Intermediate Similarity	NPC161045
0.7079	Intermediate Similarity	NPC39588
0.7079	Intermediate Similarity	NPC169575
0.7073	Intermediate Similarity	NPC472017
0.7065	Intermediate Similarity	NPC475902
0.7065	Intermediate Similarity	NPC477128
0.7065	Intermediate Similarity	NPC475819
0.7065	Intermediate Similarity	NPC476805
0.7059	Intermediate Similarity	NPC235906
0.7053	Intermediate Similarity	NPC476415
0.7053	Intermediate Similarity	NPC121825

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 NPC275507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	2031
0.2-0.3	4285
0.3-0.4	1908
0.4-0.5	485
0.5-0.6	233
0.6-0.7	40
0.7-0.8	2
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
0.7765	Intermediate Similarity	NPD5209	Approved
0.75	Intermediate Similarity	NPD1694	Approved
0.7158	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5785	Approved
0.6966	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8039	Approved
0.6667	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4225	Approved
0.6559	Remote Similarity	NPD5363	Approved
0.6489	Remote Similarity	NPD5786	Approved
0.6383	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4252	Approved
0.6341	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7521	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.6277	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7115	Discovery
0.6237	Remote Similarity	NPD4270	Approved
0.6237	Remote Similarity	NPD4269	Approved
0.62	Remote Similarity	NPD7900	Approved
0.62	Remote Similarity	NPD5282	Discontinued
0.62	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6903	Approved
0.6186	Remote Similarity	NPD6672	Approved
0.6186	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5737	Approved
0.6162	Remote Similarity	NPD5693	Phase 1
0.6162	Remote Similarity	NPD6411	Approved
0.6147	Remote Similarity	NPD6371	Approved
0.6129	Remote Similarity	NPD5369	Approved
0.6117	Remote Similarity	NPD5696	Approved
0.61	Remote Similarity	NPD6399	Phase 3
0.61	Remote Similarity	NPD5778	Approved
0.61	Remote Similarity	NPD5779	Approved
0.6082	Remote Similarity	NPD3573	Approved
0.6061	Remote Similarity	NPD6698	Approved
0.6061	Remote Similarity	NPD5207	Approved
0.6061	Remote Similarity	NPD46	Approved
0.6053	Remote Similarity	NPD6927	Phase 3
0.6044	Remote Similarity	NPD4756	Discovery
0.6026	Remote Similarity	NPD9298	Approved
0.6019	Remote Similarity	NPD7902	Approved
0.6019	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD6110	Phase 1
0.6	Remote Similarity	NPD7154	Phase 3
0.598	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7638	Approved
0.596	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.596	Remote Similarity	NPD1695	Approved
0.596	Remote Similarity	NPD5370	Suspended
0.596	Remote Similarity	NPD6101	Approved
0.5946	Remote Similarity	NPD6649	Approved
0.5946	Remote Similarity	NPD6650	Approved
0.5926	Remote Similarity	NPD6008	Approved
0.5905	Remote Similarity	NPD7639	Approved
0.5905	Remote Similarity	NPD7640	Approved
0.5895	Remote Similarity	NPD6435	Approved
0.5882	Remote Similarity	NPD7748	Approved
0.5876	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5697	Approved
0.5851	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7983	Approved
0.5842	Remote Similarity	NPD5694	Approved
0.5833	Remote Similarity	NPD5362	Discontinued
0.5825	Remote Similarity	NPD4629	Approved
0.5825	Remote Similarity	NPD5210	Approved
0.5825	Remote Similarity	NPD5695	Phase 3
0.5818	Remote Similarity	NPD6881	Approved
0.5818	Remote Similarity	NPD6686	Approved
0.5818	Remote Similarity	NPD6011	Approved
0.5818	Remote Similarity	NPD6899	Approved
0.5814	Remote Similarity	NPD7331	Phase 2
0.5814	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6080	Approved
0.58	Remote Similarity	NPD6051	Approved
0.58	Remote Similarity	NPD6673	Approved
0.58	Remote Similarity	NPD6904	Approved
0.5769	Remote Similarity	NPD7732	Phase 3
0.5769	Remote Similarity	NPD7839	Suspended
0.5766	Remote Similarity	NPD6012	Approved
0.5766	Remote Similarity	NPD6373	Approved
0.5766	Remote Similarity	NPD6014	Approved
0.5766	Remote Similarity	NPD6372	Approved
0.5766	Remote Similarity	NPD6013	Approved
0.5747	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD7838	Discovery
0.5743	Remote Similarity	NPD5692	Phase 3
0.5728	Remote Similarity	NPD6001	Approved
0.5727	Remote Similarity	NPD6614	Approved
0.5727	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7260	Phase 2
0.5714	Remote Similarity	NPD6883	Approved
0.5714	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD4194	Approved
0.5714	Remote Similarity	NPD4191	Approved
0.5714	Remote Similarity	NPD4193	Approved
0.5714	Remote Similarity	NPD7290	Approved
0.5714	Remote Similarity	NPD4192	Approved
0.5714	Remote Similarity	NPD6084	Phase 2
0.57	Remote Similarity	NPD5208	Approved
0.5686	Remote Similarity	NPD6079	Approved
0.5686	Remote Similarity	NPD5281	Approved
0.5686	Remote Similarity	NPD6050	Approved
0.5686	Remote Similarity	NPD5284	Approved
0.5686	Remote Similarity	NPD7515	Phase 2
0.5684	Remote Similarity	NPD5368	Approved
0.5664	Remote Similarity	NPD6617	Approved
0.5664	Remote Similarity	NPD6869	Approved
0.5664	Remote Similarity	NPD6847	Approved
0.5664	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8130	Phase 1
0.5658	Remote Similarity	NPD5343	Approved
0.5657	Remote Similarity	NPD3618	Phase 1
0.5657	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4249	Approved
0.5638	Remote Similarity	NPD4268	Approved
0.5638	Remote Similarity	NPD4271	Approved
0.5636	Remote Similarity	NPD6675	Approved
0.5636	Remote Similarity	NPD5739	Approved
0.5636	Remote Similarity	NPD7128	Approved
0.5636	Remote Similarity	NPD6402	Approved
0.5619	Remote Similarity	NPD4697	Phase 3
0.5619	Remote Similarity	NPD5222	Approved
0.5619	Remote Similarity	NPD5221	Approved
0.5619	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD8297	Approved
0.5614	Remote Similarity	NPD6882	Approved
0.5612	Remote Similarity	NPD3665	Phase 1
0.5612	Remote Similarity	NPD3666	Approved
0.5612	Remote Similarity	NPD3133	Approved
0.56	Remote Similarity	NPD4251	Approved
0.56	Remote Similarity	NPD3174	Discontinued
0.56	Remote Similarity	NPD4250	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