NPASS Compound

Structure

CID296683 OpenBabel06191716102D 30 32 0 0 1 0 0 0 0 0999 V2000 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 7 2 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 27 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 26 2 0 0 0 0 22 18 1 1 0 0 0 22 23 1 0 0 0 0 23 25 1 6 0 0 0 24 26 1 0 0 0 0 24 27 2 0 0 0 0 25 28 2 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 28 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.26
Volume:	461.027
LogP:	7.758
LogD:	4.585
LogS:	-4.394
# Rotatable Bonds:	7
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	3.882
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.706
MDCK Permeability:	1.828064523579087e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.903
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	101.77111053466797%
Volume Distribution (VD):	0.619
Pgp-substrate:	0.3542386293411255%

ADMET: Metabolism

CYP1A2-inhibitor:	0.574
CYP1A2-substrate:	0.44
CYP2C19-inhibitor:	0.891
CYP2C19-substrate:	0.128
CYP2C9-inhibitor:	0.51
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.563
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.471
CYP3A4-substrate:	0.461

ADMET: Excretion

Clearance (CL):	7.473
Half-life (T1/2):	0.035

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.187
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.179
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.891
Carcinogencity:	0.452
Eye Corrosion:	0.003
Eye Irritation:	0.125
Respiratory Toxicity:	0.379

Download Data

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

Natural Product: NPC296683

Natural Product ID:	NPC296683
*Common Name:**	Monoterpenylmagnolol
IUPAC Name:	2-(2-hydroxy-5-prop-2-enylphenyl)-6-[(1S,6S)-3-methyl-6-propan-2-ylcyclohex-2-en-1-yl]-4-prop-2-enylphenol
Synonyms:
Standard InCHIKey:	QIWQHZQTBNPZSG-XZOQPEGZSA-N
Standard InCHI:	InChI=1S/C28H34O2/c1-6-8-20-11-13-27(29)24(15-20)26-17-21(9-7-2)16-25(28(26)30)23-14-19(5)10-12-22(23)18(3)4/h6-7,11,13-18,22-23,29-30H,1-2,8-10,12H2,3-5H3/t22-,23+/m0/s1
SMILES:	C=CCc1cc([C@@H]2C=C(C)CC[C@H]2C(C)C)c(c(c1)c1cc(CC=C)ccc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3765325
PubChem CID:	11732171
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives

*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
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	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	5
Others	1

Activity Type	# Activity
Cell Line	2
CELL-LINE	1
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	=	16600.0	nM	PMID[520133]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	18600.0	nM	PMID[520133]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10840.0	nM	PMID[520132]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14850.0	nM	PMID[520132]
NPT22158	CELL-LINE	HCC827	Homo sapiens	IC50	=	15850.0	nM	PMID[520133]
NPT35	Others	n.a.		Solubility	<	10.0	ug.mL-1	PMID[520133]

☑ 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 NPC296683 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	297
0.1-0.2	1603
0.2-0.3	3541
0.3-0.4	12095
0.4-0.5	7650
0.5-0.6	9299
0.6-0.7	6423
0.7-0.8	1499
0.8-0.85	214
0.85-0.9	64
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.951	High Similarity	NPC138942
0.9412	High Similarity	NPC288411
0.9314	High Similarity	NPC168829
0.9231	High Similarity	NPC271274
0.9159	High Similarity	NPC95716
0.9074	High Similarity	NPC46940
0.9057	High Similarity	NPC262365
0.8991	High Similarity	NPC715
0.8972	High Similarity	NPC58865
0.8922	High Similarity	NPC77492
0.8909	High Similarity	NPC195922
0.8899	High Similarity	NPC62867
0.8899	High Similarity	NPC177962
0.8899	High Similarity	NPC250323
0.8889	High Similarity	NPC13482
0.8879	High Similarity	NPC11554
0.8868	High Similarity	NPC54765
0.8846	High Similarity	NPC51015
0.8824	High Similarity	NPC216520
0.8824	High Similarity	NPC292730
0.8824	High Similarity	NPC473388
0.8824	High Similarity	NPC82664
0.8824	High Similarity	NPC132271
0.8807	High Similarity	NPC308689
0.8807	High Similarity	NPC266937
0.8807	High Similarity	NPC470770
0.8807	High Similarity	NPC151537
0.8785	High Similarity	NPC151477
0.8774	High Similarity	NPC99557
0.8774	High Similarity	NPC219286
0.875	High Similarity	NPC471668
0.875	High Similarity	NPC225506
0.8739	High Similarity	NPC12656
0.8727	High Similarity	NPC228425
0.8727	High Similarity	NPC286222
0.8725	High Similarity	NPC8392
0.8725	High Similarity	NPC26244
0.8716	High Similarity	NPC44732
0.8716	High Similarity	NPC141782
0.8704	High Similarity	NPC95344
0.8692	High Similarity	NPC21594
0.8684	High Similarity	NPC151197
0.8673	High Similarity	NPC299180
0.8673	High Similarity	NPC477136
0.8654	High Similarity	NPC122005
0.8654	High Similarity	NPC252821
0.8654	High Similarity	NPC92730
0.8649	High Similarity	NPC35344
0.8649	High Similarity	NPC141003
0.8636	High Similarity	NPC260323
0.8636	High Similarity	NPC176279
0.8636	High Similarity	NPC77772
0.8627	High Similarity	NPC151715
0.8627	High Similarity	NPC128062
0.8624	High Similarity	NPC314187
0.8598	High Similarity	NPC117115
0.8584	High Similarity	NPC308828
0.8584	High Similarity	NPC141001
0.8571	High Similarity	NPC268160
0.8571	High Similarity	NPC473137
0.8559	High Similarity	NPC228988
0.8558	High Similarity	NPC225464
0.8545	High Similarity	NPC132720
0.8532	High Similarity	NPC61885
0.8532	High Similarity	NPC63698
0.8529	High Similarity	NPC271440
0.8522	High Similarity	NPC93071
0.8505	High Similarity	NPC238696
0.8496	Intermediate Similarity	NPC147179
0.8496	Intermediate Similarity	NPC35797
0.8496	Intermediate Similarity	NPC192948
0.8491	Intermediate Similarity	NPC12221
0.8482	Intermediate Similarity	NPC117846
0.8482	Intermediate Similarity	NPC322239
0.8476	Intermediate Similarity	NPC128723
0.8468	Intermediate Similarity	NPC165770
0.8468	Intermediate Similarity	NPC4493
0.8468	Intermediate Similarity	NPC225679
0.8468	Intermediate Similarity	NPC476632
0.8448	Intermediate Similarity	NPC260832
0.8448	Intermediate Similarity	NPC475245
0.8448	Intermediate Similarity	NPC135467
0.844	Intermediate Similarity	NPC320439
0.8435	Intermediate Similarity	NPC469609
0.8431	Intermediate Similarity	NPC204210
0.8431	Intermediate Similarity	NPC45040
0.8431	Intermediate Similarity	NPC304541
0.8421	Intermediate Similarity	NPC469663
0.8421	Intermediate Similarity	NPC219112
0.8421	Intermediate Similarity	NPC38893
0.8421	Intermediate Similarity	NPC92
0.8421	Intermediate Similarity	NPC308311
0.8421	Intermediate Similarity	NPC477137
0.8411	Intermediate Similarity	NPC108497
0.8407	Intermediate Similarity	NPC107240
0.8396	Intermediate Similarity	NPC72729
0.8396	Intermediate Similarity	NPC248396
0.8396	Intermediate Similarity	NPC48730
0.8396	Intermediate Similarity	NPC129373
0.8393	Intermediate Similarity	NPC43525
0.8393	Intermediate Similarity	NPC166995
0.8381	Intermediate Similarity	NPC79241
0.8381	Intermediate Similarity	NPC6597
0.8376	Intermediate Similarity	NPC32322
0.8376	Intermediate Similarity	NPC259703
0.8365	Intermediate Similarity	NPC32714
0.8365	Intermediate Similarity	NPC274678
0.8365	Intermediate Similarity	NPC144682
0.8362	Intermediate Similarity	NPC469644
0.8362	Intermediate Similarity	NPC126002
0.8349	Intermediate Similarity	NPC469913
0.8349	Intermediate Similarity	NPC155072
0.8349	Intermediate Similarity	NPC248904
0.8348	Intermediate Similarity	NPC16030
0.8348	Intermediate Similarity	NPC304510
0.8348	Intermediate Similarity	NPC172219
0.8348	Intermediate Similarity	NPC470760
0.8333	Intermediate Similarity	NPC55561
0.8333	Intermediate Similarity	NPC475225
0.8333	Intermediate Similarity	NPC323810
0.8333	Intermediate Similarity	NPC84999
0.8333	Intermediate Similarity	NPC246760
0.8318	Intermediate Similarity	NPC252105
0.8318	Intermediate Similarity	NPC477685
0.8304	Intermediate Similarity	NPC54373
0.8304	Intermediate Similarity	NPC224527
0.8304	Intermediate Similarity	NPC469912
0.8304	Intermediate Similarity	NPC322753
0.8302	Intermediate Similarity	NPC132078
0.8302	Intermediate Similarity	NPC260775
0.8302	Intermediate Similarity	NPC51333
0.8302	Intermediate Similarity	NPC78119
0.8302	Intermediate Similarity	NPC216468
0.8291	Intermediate Similarity	NPC477037
0.8291	Intermediate Similarity	NPC318581
0.8291	Intermediate Similarity	NPC325544
0.8288	Intermediate Similarity	NPC254833
0.8288	Intermediate Similarity	NPC228343
0.8286	Intermediate Similarity	NPC312132
0.8286	Intermediate Similarity	NPC259512
0.8276	Intermediate Similarity	NPC471671
0.8276	Intermediate Similarity	NPC154030
0.8273	Intermediate Similarity	NPC228737
0.8269	Intermediate Similarity	NPC152415
0.8269	Intermediate Similarity	NPC316301
0.8269	Intermediate Similarity	NPC289769
0.8269	Intermediate Similarity	NPC27323
0.8269	Intermediate Similarity	NPC76938
0.8261	Intermediate Similarity	NPC115808
0.8261	Intermediate Similarity	NPC261973
0.8257	Intermediate Similarity	NPC47284
0.8257	Intermediate Similarity	NPC474839
0.8246	Intermediate Similarity	NPC249270
0.8246	Intermediate Similarity	NPC471534
0.8241	Intermediate Similarity	NPC135784
0.8241	Intermediate Similarity	NPC235762
0.8241	Intermediate Similarity	NPC471228
0.8241	Intermediate Similarity	NPC269212
0.8241	Intermediate Similarity	NPC233827
0.8235	Intermediate Similarity	NPC258219
0.8235	Intermediate Similarity	NPC71094
0.8235	Intermediate Similarity	NPC70436
0.8235	Intermediate Similarity	NPC123273
0.8235	Intermediate Similarity	NPC176208
0.8235	Intermediate Similarity	NPC318325
0.8235	Intermediate Similarity	NPC297057
0.8235	Intermediate Similarity	NPC280347
0.8235	Intermediate Similarity	NPC177420
0.8235	Intermediate Similarity	NPC242240
0.823	Intermediate Similarity	NPC471179
0.8224	Intermediate Similarity	NPC12931
0.8224	Intermediate Similarity	NPC213730
0.8224	Intermediate Similarity	NPC70677
0.8224	Intermediate Similarity	NPC130756
0.822	Intermediate Similarity	NPC129176
0.8208	Intermediate Similarity	NPC152097
0.8208	Intermediate Similarity	NPC32674
0.8208	Intermediate Similarity	NPC156313
0.8205	Intermediate Similarity	NPC176893
0.8205	Intermediate Similarity	NPC182240
0.8198	Intermediate Similarity	NPC201959
0.8182	Intermediate Similarity	NPC53740
0.8174	Intermediate Similarity	NPC469719
0.8173	Intermediate Similarity	NPC306884
0.8173	Intermediate Similarity	NPC210497
0.8173	Intermediate Similarity	NPC162314
0.8173	Intermediate Similarity	NPC94139
0.8173	Intermediate Similarity	NPC147284
0.8173	Intermediate Similarity	NPC3358
0.8165	Intermediate Similarity	NPC272029
0.8165	Intermediate Similarity	NPC119860
0.8158	Intermediate Similarity	NPC263753
0.8158	Intermediate Similarity	NPC321589
0.8158	Intermediate Similarity	NPC23804
0.8158	Intermediate Similarity	NPC317869
0.8151	Intermediate Similarity	NPC154696
0.8148	Intermediate Similarity	NPC7686
0.8148	Intermediate Similarity	NPC80800
0.8148	Intermediate Similarity	NPC40258
0.8148	Intermediate Similarity	NPC91461

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 NPC296683 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	1030
0.2-0.3	1099
0.3-0.4	2808
0.4-0.5	2065
0.5-0.6	1289
0.6-0.7	479
0.7-0.8	80
0.8-0.85	10
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.902	High Similarity	NPD3020	Approved
0.8899	High Similarity	NPD7635	Approved
0.8725	High Similarity	NPD2860	Approved
0.8725	High Similarity	NPD2859	Approved
0.8627	High Similarity	NPD2933	Approved
0.8627	High Similarity	NPD2934	Approved
0.8529	High Similarity	NPD845	Approved
0.844	Intermediate Similarity	NPD2342	Discontinued
0.8365	Intermediate Similarity	NPD1809	Phase 2
0.8288	Intermediate Similarity	NPD3021	Approved
0.8288	Intermediate Similarity	NPD3022	Approved
0.8286	Intermediate Similarity	NPD288	Approved
0.8269	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD844	Approved
0.8125	Intermediate Similarity	NPD4750	Phase 3
0.8056	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD2932	Approved
0.7982	Intermediate Similarity	NPD940	Approved
0.7982	Intermediate Similarity	NPD846	Approved
0.7966	Intermediate Similarity	NPD3091	Approved
0.7966	Intermediate Similarity	NPD5303	Approved
0.7966	Intermediate Similarity	NPD5304	Approved
0.7949	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD2229	Approved
0.7845	Intermediate Similarity	NPD2234	Approved
0.7845	Intermediate Similarity	NPD2228	Approved
0.7833	Intermediate Similarity	NPD3019	Approved
0.7833	Intermediate Similarity	NPD2286	Discontinued
0.7833	Intermediate Similarity	NPD4059	Approved
0.7833	Intermediate Similarity	NPD4589	Approved
0.7826	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4093	Discontinued
0.7745	Intermediate Similarity	NPD111	Approved
0.7705	Intermediate Similarity	NPD3092	Approved
0.7692	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD497	Approved
0.76	Intermediate Similarity	NPD3094	Phase 2
0.7589	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3028	Approved
0.7568	Intermediate Similarity	NPD1242	Phase 1
0.7563	Intermediate Similarity	NPD6671	Approved
0.7542	Intermediate Similarity	NPD495	Approved
0.7542	Intermediate Similarity	NPD496	Approved
0.7542	Intermediate Similarity	NPD498	Approved
0.7541	Intermediate Similarity	NPD3095	Discontinued
0.7521	Intermediate Similarity	NPD7330	Discontinued
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD1792	Phase 2
0.748	Intermediate Similarity	NPD5736	Approved
0.748	Intermediate Similarity	NPD2861	Phase 2
0.7422	Intermediate Similarity	NPD4908	Phase 1
0.7419	Intermediate Similarity	NPD1610	Phase 2
0.7398	Intermediate Similarity	NPD1751	Approved
0.7398	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD4626	Approved
0.7395	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1445	Approved
0.7391	Intermediate Similarity	NPD1444	Approved
0.7333	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4060	Phase 1
0.7323	Intermediate Similarity	NPD1164	Approved
0.7302	Intermediate Similarity	NPD4749	Approved
0.728	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD1201	Approved
0.728	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6387	Discontinued
0.7252	Intermediate Similarity	NPD6663	Approved
0.725	Intermediate Similarity	NPD5283	Phase 1
0.7244	Intermediate Similarity	NPD1283	Approved
0.7231	Intermediate Similarity	NPD5156	Approved
0.7231	Intermediate Similarity	NPD5155	Approved
0.7218	Intermediate Similarity	NPD4097	Suspended
0.7213	Intermediate Similarity	NPD7340	Approved
0.7213	Intermediate Similarity	NPD7636	Approved
0.7209	Intermediate Similarity	NPD3637	Approved
0.7209	Intermediate Similarity	NPD3636	Approved
0.7209	Intermediate Similarity	NPD3635	Approved
0.7203	Intermediate Similarity	NPD5451	Approved
0.72	Intermediate Similarity	NPD3023	Approved
0.72	Intermediate Similarity	NPD3026	Approved
0.7188	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3025	Approved
0.7177	Intermediate Similarity	NPD1651	Approved
0.7177	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3024	Approved
0.7176	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4659	Approved
0.7154	Intermediate Similarity	NPD2606	Approved
0.7154	Intermediate Similarity	NPD2605	Approved
0.7132	Intermediate Similarity	NPD2195	Approved
0.7132	Intermediate Similarity	NPD2194	Approved
0.7132	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4624	Approved
0.7121	Intermediate Similarity	NPD6405	Approved
0.7121	Intermediate Similarity	NPD6407	Approved
0.712	Intermediate Similarity	NPD2668	Approved
0.712	Intermediate Similarity	NPD2667	Approved
0.7109	Intermediate Similarity	NPD8651	Approved
0.7109	Intermediate Similarity	NPD6696	Suspended
0.7101	Intermediate Similarity	NPD7003	Approved
0.7097	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1548	Phase 1
0.7094	Intermediate Similarity	NPD968	Approved
0.7087	Intermediate Similarity	NPD2232	Approved
0.7087	Intermediate Similarity	NPD2233	Approved
0.7087	Intermediate Similarity	NPD2230	Approved
0.7069	Intermediate Similarity	NPD9610	Approved
0.7069	Intermediate Similarity	NPD9608	Approved
0.7063	Intermediate Similarity	NPD3143	Discontinued
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD5405	Approved
0.7054	Intermediate Similarity	NPD2797	Approved
0.7054	Intermediate Similarity	NPD1470	Approved
0.7054	Intermediate Similarity	NPD4103	Phase 2
0.7054	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5691	Approved
0.7031	Intermediate Similarity	NPD5327	Phase 3
0.7031	Intermediate Similarity	NPD6582	Phase 2
0.7031	Intermediate Similarity	NPD6583	Phase 3
0.7031	Intermediate Similarity	NPD1669	Approved
0.7025	Intermediate Similarity	NPD5535	Approved
0.7023	Intermediate Similarity	NPD3594	Approved
0.7023	Intermediate Similarity	NPD3595	Approved
0.7008	Intermediate Similarity	NPD1281	Approved
0.7008	Intermediate Similarity	NPD1611	Approved
0.7	Intermediate Similarity	NPD6584	Phase 3
0.6992	Remote Similarity	NPD709	Approved
0.6992	Remote Similarity	NPD7157	Approved
0.6985	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7743	Approved
0.6985	Remote Similarity	NPD7742	Approved
0.6983	Remote Similarity	NPD9500	Approved
0.6975	Remote Similarity	NPD2684	Approved
0.6967	Remote Similarity	NPD1398	Phase 1
0.6957	Remote Similarity	NPD1616	Discontinued
0.6953	Remote Similarity	NPD3070	Discontinued
0.695	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7390	Discontinued
0.695	Remote Similarity	NPD2421	Approved
0.695	Remote Similarity	NPD7041	Phase 2
0.695	Remote Similarity	NPD2420	Approved
0.6942	Remote Similarity	NPD228	Approved
0.694	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3620	Phase 2
0.6934	Remote Similarity	NPD2935	Discontinued
0.693	Remote Similarity	NPD9273	Approved
0.6929	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD475	Phase 2
0.6906	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4818	Approved
0.6897	Remote Similarity	NPD4817	Approved
0.6894	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6355	Discontinued
0.6889	Remote Similarity	NPD5735	Approved
0.6885	Remote Similarity	NPD7843	Approved
0.6885	Remote Similarity	NPD1138	Approved
0.687	Remote Similarity	NPD7451	Discontinued
0.687	Remote Similarity	NPD2798	Approved
0.6861	Remote Similarity	NPD2799	Discontinued
0.6861	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3400	Discontinued
0.6857	Remote Similarity	NPD8166	Discontinued
0.6846	Remote Similarity	NPD5310	Approved
0.6846	Remote Similarity	NPD5311	Approved
0.6842	Remote Similarity	NPD7095	Approved
0.6842	Remote Similarity	NPD3027	Phase 3
0.6838	Remote Similarity	NPD6353	Approved
0.6835	Remote Similarity	NPD4257	Approved
0.6835	Remote Similarity	NPD4256	Phase 2
0.6822	Remote Similarity	NPD2562	Approved
0.6822	Remote Similarity	NPD2561	Approved
0.6818	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4208	Discontinued
0.6815	Remote Similarity	NPD2979	Phase 3
0.6815	Remote Similarity	NPD4140	Approved
0.6815	Remote Similarity	NPD6346	Approved
0.6803	Remote Similarity	NPD1137	Approved
0.6803	Remote Similarity	NPD1139	Approved
0.68	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1983	Approved
0.6797	Remote Similarity	NPD3421	Phase 3
0.6797	Remote Similarity	NPD1981	Approved
0.6797	Remote Similarity	NPD1980	Approved
0.6797	Remote Similarity	NPD3847	Discontinued
0.6794	Remote Similarity	NPD1133	Approved
0.6794	Remote Similarity	NPD1135	Approved
0.6794	Remote Similarity	NPD1134	Approved
0.6794	Remote Similarity	NPD1131	Approved
0.6794	Remote Similarity	NPD1129	Approved
0.6794	Remote Similarity	NPD3055	Approved
0.6794	Remote Similarity	NPD3053	Approved
0.6791	Remote Similarity	NPD3268	Approved
0.6791	Remote Similarity	NPD2028	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