NPASS Compound

Structure

NPC151197 OpenBabel07101718192D 35 36 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5622 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 -0.8660 -1.5000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 -3.4641 -1.0000 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 -1.7321 -0.0000 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 0.0000 -1.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5622 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 22 2 0 0 0 0 16 27 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 24 1 0 0 0 0 19 31 1 0 0 0 0 23 24 1 0 0 0 0 25 27 2 0 0 0 0 25 29 1 0 0 0 0 26 28 2 0 0 0 0 26 30 1 0 0 0 0 27 32 1 0 0 0 0 28 33 1 0 0 0 0 29 5 1 1 0 0 0 29 34 1 0 0 0 0 30 6 1 6 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	538.455
LogP:	5.924
LogD:	4.168
LogS:	-4.062
# Rotatable Bonds:	13
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.23
Synthetic Accessibility Score:	3.818
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.767
MDCK Permeability:	2.1195533918216825e-05
Pgp-inhibitor:	0.62
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.867

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	97.28257751464844%
Volume Distribution (VD):	4.192
Pgp-substrate:	3.8558456897735596%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.195
CYP2C19-inhibitor:	0.398
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.528
CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.875
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.872
CYP3A4-substrate:	0.802

ADMET: Excretion

Clearance (CL):	11.259
Half-life (T1/2):	0.343

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.144
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.76
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.129
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC151197

Natural Product ID:	NPC151197
*Common Name:**	Disydonol C
IUPAC Name:	4-[[3-hydroxy-4-[(2S)-2-hydroxy-6-methylheptan-2-yl]phenyl]methyl]-5-(hydroxymethyl)-2-[(2S)-2-hydroxy-6-methylheptan-2-yl]phenol
Synonyms:	Disydonol C
Standard InCHIKey:	IVRQFCVGCSKHLJ-KYJUHHDHSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-20(2)9-7-13-29(5,34)25-12-11-22(16-27(25)32)15-23-17-26(28(33)18-24(23)19-31)30(6,35)14-8-10-21(3)4/h11-12,16-18,20-21,31-35H,7-10,13-15,19H2,1-6H3/t29-,30-/m0/s1
SMILES:	OCc1cc(O)c(cc1Cc1ccc(c(c1)O)[C@](CCCC(C)C)(O)C)[C@](CCCC(C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1946642
PubChem CID:	57334111
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2.91	ug.mL-1	PMID[480253]
NPT2306	Cell Line	Ca-Ski	Homo sapiens	IC50	=	10.2	ug.mL-1	PMID[480253]

☑ 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 NPC151197 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	299
0.1-0.2	1383
0.2-0.3	3073
0.3-0.4	10740
0.4-0.5	9160
0.5-0.6	7912
0.6-0.7	7520
0.7-0.8	2342
0.8-0.85	183
0.85-0.9	81
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC132720
0.9123	High Similarity	NPC474486
0.9027	High Similarity	NPC302371
0.8966	High Similarity	NPC477136
0.8957	High Similarity	NPC35797
0.8957	High Similarity	NPC192948
0.8929	High Similarity	NPC58865
0.8919	High Similarity	NPC66834
0.8919	High Similarity	NPC151477
0.8879	High Similarity	NPC469663
0.8879	High Similarity	NPC477137
0.8879	High Similarity	NPC38893
0.8879	High Similarity	NPC92
0.8879	High Similarity	NPC219112
0.8879	High Similarity	NPC308828
0.8879	High Similarity	NPC308311
0.887	High Similarity	NPC268160
0.886	High Similarity	NPC228425
0.886	High Similarity	NPC46940
0.8814	High Similarity	NPC469644
0.8803	High Similarity	NPC304510
0.8803	High Similarity	NPC172219
0.8803	High Similarity	NPC470760
0.8793	High Similarity	NPC147179
0.8783	High Similarity	NPC715
0.8772	High Similarity	NPC151537
0.8772	High Similarity	NPC95716
0.8739	High Similarity	NPC117115
0.8739	High Similarity	NPC223451
0.8729	High Similarity	NPC9592
0.8729	High Similarity	NPC471671
0.8729	High Similarity	NPC48781
0.8729	High Similarity	NPC469609
0.8718	High Similarity	NPC471668
0.8718	High Similarity	NPC115808
0.8707	High Similarity	NPC195922
0.8707	High Similarity	NPC107240
0.8696	High Similarity	NPC250323
0.8696	High Similarity	NPC228452
0.8684	High Similarity	NPC296683
0.8673	High Similarity	NPC11554
0.8673	High Similarity	NPC262365
0.8661	High Similarity	NPC21594
0.8649	High Similarity	NPC475225
0.8649	High Similarity	NPC323810
0.8644	High Similarity	NPC299180
0.8621	High Similarity	NPC261343
0.8621	High Similarity	NPC263753
0.8621	High Similarity	NPC117846
0.8609	High Similarity	NPC176279
0.8609	High Similarity	NPC469912
0.8609	High Similarity	NPC260323
0.8609	High Similarity	NPC308689
0.8607	High Similarity	NPC261992
0.8583	High Similarity	NPC260832
0.8583	High Similarity	NPC135467
0.8571	High Similarity	NPC154030
0.8571	High Similarity	NPC138942
0.8559	High Similarity	NPC471228
0.8559	High Similarity	NPC137496
0.8559	High Similarity	NPC474387
0.8559	High Similarity	NPC154511
0.8559	High Similarity	NPC235762
0.8559	High Similarity	NPC474358
0.8559	High Similarity	NPC247858
0.8559	High Similarity	NPC257540
0.8547	High Similarity	NPC12656
0.8547	High Similarity	NPC473137
0.8534	High Similarity	NPC43525
0.8534	High Similarity	NPC166995
0.8525	High Similarity	NPC188997
0.8525	High Similarity	NPC71094
0.8522	High Similarity	NPC44732
0.8522	High Similarity	NPC141782
0.8522	High Similarity	NPC13482
0.8512	High Similarity	NPC129176
0.85	High Similarity	NPC126002
0.85	High Similarity	NPC93071
0.8482	Intermediate Similarity	NPC288411
0.8482	Intermediate Similarity	NPC238696
0.8475	Intermediate Similarity	NPC246760
0.8475	Intermediate Similarity	NPC84999
0.8468	Intermediate Similarity	NPC4286
0.8468	Intermediate Similarity	NPC76119
0.8462	Intermediate Similarity	NPC23804
0.8455	Intermediate Similarity	NPC471187
0.8448	Intermediate Similarity	NPC165770
0.8448	Intermediate Similarity	NPC4493
0.8448	Intermediate Similarity	NPC225679
0.8448	Intermediate Similarity	NPC224527
0.8448	Intermediate Similarity	NPC476632
0.8443	Intermediate Similarity	NPC237667
0.8435	Intermediate Similarity	NPC314187
0.8421	Intermediate Similarity	NPC474352
0.8417	Intermediate Similarity	NPC206
0.8403	Intermediate Similarity	NPC261973
0.8403	Intermediate Similarity	NPC141001
0.8393	Intermediate Similarity	NPC168829
0.839	Intermediate Similarity	NPC249270
0.8378	Intermediate Similarity	NPC72729
0.8378	Intermediate Similarity	NPC174911
0.8376	Intermediate Similarity	NPC62867
0.8376	Intermediate Similarity	NPC471179
0.8376	Intermediate Similarity	NPC473521
0.8376	Intermediate Similarity	NPC177962
0.8362	Intermediate Similarity	NPC224870
0.8361	Intermediate Similarity	NPC24125
0.8333	Intermediate Similarity	NPC473221
0.8333	Intermediate Similarity	NPC54765
0.8333	Intermediate Similarity	NPC271274
0.8333	Intermediate Similarity	NPC320864
0.832	Intermediate Similarity	NPC105031
0.8319	Intermediate Similarity	NPC232165
0.8319	Intermediate Similarity	NPC272029
0.8319	Intermediate Similarity	NPC469719
0.8306	Intermediate Similarity	NPC53567
0.8305	Intermediate Similarity	NPC319803
0.8305	Intermediate Similarity	NPC322239
0.8304	Intermediate Similarity	NPC40258
0.8304	Intermediate Similarity	NPC7686
0.8304	Intermediate Similarity	NPC91461
0.8293	Intermediate Similarity	NPC39029
0.8291	Intermediate Similarity	NPC77772
0.8291	Intermediate Similarity	NPC470770
0.8291	Intermediate Similarity	NPC266937
0.8288	Intermediate Similarity	NPC128723
0.8281	Intermediate Similarity	NPC470727
0.8279	Intermediate Similarity	NPC68339
0.8279	Intermediate Similarity	NPC478121
0.8279	Intermediate Similarity	NPC318581
0.8279	Intermediate Similarity	NPC477037
0.8279	Intermediate Similarity	NPC472071
0.8279	Intermediate Similarity	NPC325544
0.8276	Intermediate Similarity	NPC33728
0.8276	Intermediate Similarity	NPC19808
0.8264	Intermediate Similarity	NPC164649
0.8264	Intermediate Similarity	NPC63010
0.8264	Intermediate Similarity	NPC48342
0.8261	Intermediate Similarity	NPC320439
0.8254	Intermediate Similarity	NPC82299
0.8254	Intermediate Similarity	NPC470724
0.8246	Intermediate Similarity	NPC471350
0.824	Intermediate Similarity	NPC224342
0.824	Intermediate Similarity	NPC139774
0.824	Intermediate Similarity	NPC174729
0.824	Intermediate Similarity	NPC181334
0.8235	Intermediate Similarity	NPC471534
0.8231	Intermediate Similarity	NPC474453
0.823	Intermediate Similarity	NPC108497
0.823	Intermediate Similarity	NPC168393
0.8226	Intermediate Similarity	NPC152946
0.8226	Intermediate Similarity	NPC121168
0.8226	Intermediate Similarity	NPC471794
0.8226	Intermediate Similarity	NPC11250
0.8226	Intermediate Similarity	NPC297057
0.8214	Intermediate Similarity	NPC294741
0.8214	Intermediate Similarity	NPC213730
0.8211	Intermediate Similarity	NPC32322
0.8211	Intermediate Similarity	NPC328504
0.8211	Intermediate Similarity	NPC241001
0.8211	Intermediate Similarity	NPC277798
0.8211	Intermediate Similarity	NPC259703
0.8211	Intermediate Similarity	NPC100108
0.8205	Intermediate Similarity	NPC475018
0.8198	Intermediate Similarity	NPC79241
0.8198	Intermediate Similarity	NPC6597
0.8198	Intermediate Similarity	NPC77492
0.8197	Intermediate Similarity	NPC217174
0.8197	Intermediate Similarity	NPC323074
0.8197	Intermediate Similarity	NPC160235
0.8197	Intermediate Similarity	NPC121866
0.8197	Intermediate Similarity	NPC191866
0.819	Intermediate Similarity	NPC63698
0.819	Intermediate Similarity	NPC174981
0.819	Intermediate Similarity	NPC61885
0.819	Intermediate Similarity	NPC95344
0.8189	Intermediate Similarity	NPC476536
0.8189	Intermediate Similarity	NPC471077
0.8182	Intermediate Similarity	NPC16030
0.8175	Intermediate Similarity	NPC470726
0.8175	Intermediate Similarity	NPC124030
0.8174	Intermediate Similarity	NPC469913
0.8174	Intermediate Similarity	NPC53740
0.8174	Intermediate Similarity	NPC67250
0.816	Intermediate Similarity	NPC198014
0.8151	Intermediate Similarity	NPC471485
0.8151	Intermediate Similarity	NPC317869
0.8145	Intermediate Similarity	NPC474115
0.8145	Intermediate Similarity	NPC475166
0.8145	Intermediate Similarity	NPC253627
0.8142	Intermediate Similarity	NPC252105
0.8142	Intermediate Similarity	NPC80800
0.8142	Intermediate Similarity	NPC477685
0.8142	Intermediate Similarity	NPC12221
0.814	Intermediate Similarity	NPC472369
0.8136	Intermediate Similarity	NPC187583
0.8136	Intermediate Similarity	NPC179002
0.8136	Intermediate Similarity	NPC257430
0.8136	Intermediate Similarity	NPC54373
0.8136	Intermediate Similarity	NPC322753

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 NPC151197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	954
0.2-0.3	1367
0.3-0.4	2799
0.4-0.5	1972
0.5-0.6	1211
0.6-0.7	498
0.7-0.8	91
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.886	High Similarity	NPD7635	Approved
0.8288	Intermediate Similarity	NPD3020	Approved
0.8264	Intermediate Similarity	NPD3091	Approved
0.8261	Intermediate Similarity	NPD2342	Discontinued
0.8175	Intermediate Similarity	NPD3094	Phase 2
0.816	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD4750	Phase 3
0.812	Intermediate Similarity	NPD3022	Approved
0.812	Intermediate Similarity	NPD3021	Approved
0.8108	Intermediate Similarity	NPD288	Approved
0.8018	Intermediate Similarity	NPD2859	Approved
0.8018	Intermediate Similarity	NPD2860	Approved
0.8018	Intermediate Similarity	NPD844	Approved
0.8	Intermediate Similarity	NPD3092	Approved
0.7984	Intermediate Similarity	NPD3095	Discontinued
0.7951	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD2933	Approved
0.7928	Intermediate Similarity	NPD2934	Approved
0.784	Intermediate Similarity	NPD4059	Approved
0.7838	Intermediate Similarity	NPD845	Approved
0.7787	Intermediate Similarity	NPD497	Approved
0.7786	Intermediate Similarity	NPD4625	Phase 3
0.7759	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4060	Phase 1
0.7739	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD495	Approved
0.7705	Intermediate Similarity	NPD498	Approved
0.7705	Intermediate Similarity	NPD496	Approved
0.7699	Intermediate Similarity	NPD1809	Phase 2
0.7698	Intermediate Similarity	NPD4626	Approved
0.7698	Intermediate Similarity	NPD2286	Discontinued
0.7698	Intermediate Similarity	NPD3019	Approved
0.7698	Intermediate Similarity	NPD2932	Approved
0.7692	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD940	Approved
0.7672	Intermediate Similarity	NPD846	Approved
0.7634	Intermediate Similarity	NPD5736	Approved
0.763	Intermediate Similarity	NPD4097	Suspended
0.7619	Intermediate Similarity	NPD4093	Discontinued
0.7611	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1242	Phase 1
0.7561	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD7340	Approved
0.748	Intermediate Similarity	NPD5691	Approved
0.7444	Intermediate Similarity	NPD4908	Phase 1
0.744	Intermediate Similarity	NPD6671	Approved
0.7422	Intermediate Similarity	NPD1751	Approved
0.7419	Intermediate Similarity	NPD2228	Approved
0.7419	Intermediate Similarity	NPD2234	Approved
0.7419	Intermediate Similarity	NPD2229	Approved
0.7407	Intermediate Similarity	NPD6407	Approved
0.7407	Intermediate Similarity	NPD6405	Approved
0.7407	Intermediate Similarity	NPD6663	Approved
0.7405	Intermediate Similarity	NPD1283	Approved
0.7405	Intermediate Similarity	NPD6696	Suspended
0.7402	Intermediate Similarity	NPD5304	Approved
0.7402	Intermediate Similarity	NPD5303	Approved
0.7388	Intermediate Similarity	NPD3027	Phase 3
0.7377	Intermediate Similarity	NPD1792	Phase 2
0.7368	Intermediate Similarity	NPD2861	Phase 2
0.7348	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1651	Approved
0.7343	Intermediate Similarity	NPD7041	Phase 2
0.7343	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5405	Approved
0.7338	Intermediate Similarity	NPD5406	Approved
0.7338	Intermediate Similarity	NPD5408	Approved
0.7338	Intermediate Similarity	NPD5404	Approved
0.7328	Intermediate Similarity	NPD4749	Approved
0.7308	Intermediate Similarity	NPD1610	Phase 2
0.7308	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4624	Approved
0.7287	Intermediate Similarity	NPD4589	Approved
0.728	Intermediate Similarity	NPD5283	Phase 1
0.728	Intermediate Similarity	NPD1398	Phase 1
0.7266	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD7743	Approved
0.7266	Intermediate Similarity	NPD7742	Approved
0.7252	Intermediate Similarity	NPD2233	Approved
0.7252	Intermediate Similarity	NPD2230	Approved
0.7252	Intermediate Similarity	NPD2232	Approved
0.7231	Intermediate Similarity	NPD3026	Approved
0.7231	Intermediate Similarity	NPD3023	Approved
0.7226	Intermediate Similarity	NPD3620	Phase 2
0.7226	Intermediate Similarity	NPD2238	Phase 2
0.7226	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2979	Phase 3
0.7222	Intermediate Similarity	NPD7390	Discontinued
0.7214	Intermediate Similarity	NPD2935	Discontinued
0.7209	Intermediate Similarity	NPD3025	Approved
0.7209	Intermediate Similarity	NPD3024	Approved
0.7197	Intermediate Similarity	NPD5327	Phase 3
0.7183	Intermediate Similarity	NPD6674	Discontinued
0.7176	Intermediate Similarity	NPD1611	Approved
0.7176	Intermediate Similarity	NPD1201	Approved
0.7176	Intermediate Similarity	NPD1281	Approved
0.7174	Intermediate Similarity	NPD5735	Approved
0.7172	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2195	Approved
0.7164	Intermediate Similarity	NPD2194	Approved
0.7154	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3028	Approved
0.7132	Intermediate Similarity	NPD5156	Approved
0.7132	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5155	Approved
0.7131	Intermediate Similarity	NPD1444	Approved
0.7131	Intermediate Similarity	NPD1445	Approved
0.7123	Intermediate Similarity	NPD6090	Discontinued
0.7122	Intermediate Similarity	NPD6353	Approved
0.7117	Intermediate Similarity	NPD111	Approved
0.7111	Intermediate Similarity	NPD3637	Approved
0.7111	Intermediate Similarity	NPD3635	Approved
0.7111	Intermediate Similarity	NPD3636	Approved
0.7101	Intermediate Similarity	NPD1613	Approved
0.7101	Intermediate Similarity	NPD4140	Approved
0.7101	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1470	Approved
0.7068	Intermediate Similarity	NPD1669	Approved
0.7059	Intermediate Similarity	NPD2606	Approved
0.7059	Intermediate Similarity	NPD2605	Approved
0.7042	Intermediate Similarity	NPD5762	Approved
0.7042	Intermediate Similarity	NPD5763	Approved
0.7031	Intermediate Similarity	NPD7157	Approved
0.7023	Intermediate Similarity	NPD5126	Approved
0.7023	Intermediate Similarity	NPD5125	Phase 3
0.7021	Intermediate Similarity	NPD4108	Discontinued
0.702	Intermediate Similarity	NPD5929	Approved
0.7	Intermediate Similarity	NPD7330	Discontinued
0.7	Intermediate Similarity	NPD2568	Approved
0.7	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD7741	Discontinued
0.698	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6100	Approved
0.6972	Remote Similarity	NPD2438	Suspended
0.6972	Remote Similarity	NPD6099	Approved
0.6966	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1135	Approved
0.6963	Remote Similarity	NPD1133	Approved
0.6963	Remote Similarity	NPD1129	Approved
0.6963	Remote Similarity	NPD1134	Approved
0.6963	Remote Similarity	NPD4103	Phase 2
0.6963	Remote Similarity	NPD1131	Approved
0.6963	Remote Similarity	NPD1164	Approved
0.695	Remote Similarity	NPD3554	Approved
0.695	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3552	Approved
0.695	Remote Similarity	NPD3553	Approved
0.695	Remote Similarity	NPD3555	Approved
0.6944	Remote Similarity	NPD3638	Discontinued
0.694	Remote Similarity	NPD4659	Approved
0.6934	Remote Similarity	NPD3595	Approved
0.6934	Remote Similarity	NPD3594	Approved
0.6934	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7843	Approved
0.6923	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6584	Phase 3
0.6899	Remote Similarity	NPD6387	Discontinued
0.6899	Remote Similarity	NPD709	Approved
0.6897	Remote Similarity	NPD3400	Discontinued
0.6897	Remote Similarity	NPD8166	Discontinued
0.6897	Remote Similarity	NPD7003	Approved
0.6894	Remote Similarity	NPD2668	Approved
0.6894	Remote Similarity	NPD2667	Approved
0.6889	Remote Similarity	NPD8651	Approved
0.688	Remote Similarity	NPD2684	Approved
0.6879	Remote Similarity	NPD2157	Approved
0.6875	Remote Similarity	NPD7037	Approved
0.6861	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD968	Approved
0.6853	Remote Similarity	NPD2531	Phase 2
0.685	Remote Similarity	NPD228	Approved
0.6842	Remote Similarity	NPD37	Approved
0.6835	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7985	Registered
0.6822	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9618	Approved
0.6822	Remote Similarity	NPD9614	Approved
0.6809	Remote Similarity	NPD6355	Discontinued
0.6806	Remote Similarity	NPD4725	Approved
0.6806	Remote Similarity	NPD7266	Discontinued
0.6806	Remote Similarity	NPD4726	Approved
0.6806	Remote Similarity	NPD4721	Approved
0.6794	Remote Similarity	NPD7644	Approved
0.6792	Remote Similarity	NPD7473	Discontinued
0.6788	Remote Similarity	NPD3690	Phase 2
0.6788	Remote Similarity	NPD3691	Phase 2
0.6781	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3892	Phase 2
0.6763	Remote Similarity	NPD7095	Approved
0.6761	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5314	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