NPASS Compound

Structure

NPC474568 OpenBabel07101719252D 39 44 0 0 1 0 0 0 0 0999 V2000 1.3481 -2.3844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5654 -1.6816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1158 -2.2216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9819 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0461 -0.3608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5461 -1.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5461 0.5052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5461 -1.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5461 0.5052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0461 -0.3608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5461 -1.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4638 -1.2743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6249 -1.0824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4940 1.0366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7880 0.6157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1055 3.6120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1744 -1.3996 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7993 -1.0388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0461 -0.3608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.7216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7993 0.3173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2498 -0.7216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2184 1.9979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5461 -1.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8290 0.5592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0461 -0.3608 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2481 2.2398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2498 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5534 1.5205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6249 0.3608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0461 -2.0928 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6249 1.3608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1158 -1.2216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1158 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4460 1.5554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7483 2.8459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1783 3.2374 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0461 -0.3608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 34 1 0 0 0 0 4 35 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 19 2 0 0 0 0 9 19 1 0 0 0 0 10 11 2 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 20 2 0 0 0 0 13 22 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 36 1 0 0 0 0 16 37 1 0 0 0 0 16 38 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 18 2 1 6 0 0 0 18 26 1 0 0 0 0 20 31 1 0 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 22 28 2 0 0 0 0 22 34 1 0 0 0 0 23 27 2 0 0 0 0 23 37 1 0 0 0 0 24 32 2 0 0 0 0 24 39 1 0 0 0 0 25 29 2 0 0 0 0 25 31 1 0 0 0 0 26 39 1 6 0 0 0 27 29 1 0 0 0 0 27 38 1 0 0 0 0 28 30 1 0 0 0 0 28 35 1 0 0 0 0 29 36 1 0 0 0 0 30 31 1 0 0 0 0 30 33 2 0 0 0 0 31 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.19
Volume:	534.714
LogP:	4.967
LogD:	4.692
LogS:	-5.484
# Rotatable Bonds:	6
TPSA:	89.52
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	5.146
Fsp3:	0.355
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.817
MDCK Permeability:	1.412469646311365e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.105

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	95.13433837890625%
Volume Distribution (VD):	0.65
Pgp-substrate:	4.6543426513671875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.347
CYP1A2-substrate:	0.785
CYP2C19-inhibitor:	0.978
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.97
CYP2C9-substrate:	0.366
CYP2D6-inhibitor:	0.911
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.979
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	7.596
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.459
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.586
Maximum Recommended Daily Dose:	0.375
Skin Sensitization:	0.226
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.119
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC474568

Natural Product ID:	NPC474568
*Common Name:**	Schiarisanrin D
IUPAC Name:	n.a.
Synonyms:	Schiarisanrin D
Standard InCHIKey:	ACFUZZGYRLQTDI-VNUPLTAFSA-N
Standard InCHI:	InChI=1S/C31H30O8/c1-17-12-20-13-22(34-3)28(35-4)30(33)31(20)15-36-29-25(31)21(14-23-27(29)38-16-37-23)26(18(17)2)39-24(32)11-10-19-8-6-5-7-9-19/h5-11,13-14,17-18,26H,12,15-16H2,1-4H3/b11-10+/t17-,18-,26-,31+/m1/s1
SMILES:	COC1=C(OC)C=C2[C@@]3(C1=O)COc1c3c(cc3c1OCO3)[C@@H]([C@@H]([C@@H](C2)C)C)OC(=O)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL473877
PubChem CID:	44584767
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO10144	Kadsura matsudai	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11215493]
NPO10144	Kadsura matsudai	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325232]
NPO10144	Kadsura matsudai	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10144	Kadsura matsudai	Species	Schisandraceae	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
Others	6

Activity Type	# Activity
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Activity	<	25.0	%	PMID[522524]
NPT27	Others	Unspecified		Activity	=	20.1	IU/L	PMID[522524]
NPT27	Others	Unspecified		Activity	=	22.0	IU/L	PMID[522524]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Activity	=	42.9	%	PMID[522524]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Activity	=	27.0	%	PMID[522524]

☑ 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 NPC474568 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	473
0.1-0.2	1658
0.2-0.3	3669
0.3-0.4	8196
0.4-0.5	9967
0.5-0.6	4509
0.6-0.7	6584
0.7-0.8	7172
0.8-0.85	423
0.85-0.9	32
0.9-0.95	5
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9752	High Similarity	NPC42230
0.963	High Similarity	NPC474948
0.9627	High Similarity	NPC475953
0.9506	High Similarity	NPC474647
0.913	High Similarity	NPC117154
0.903	High Similarity	NPC61141
0.8963	High Similarity	NPC325122
0.8957	High Similarity	NPC477380
0.8951	High Similarity	NPC348849
0.8951	High Similarity	NPC178195
0.8902	High Similarity	NPC477885
0.8855	High Similarity	NPC258322
0.8855	High Similarity	NPC191352
0.8824	High Similarity	NPC477883
0.881	High Similarity	NPC477884
0.8765	High Similarity	NPC303519
0.8743	High Similarity	NPC209411
0.8743	High Similarity	NPC239890
0.8727	High Similarity	NPC301897
0.8721	High Similarity	NPC477881
0.872	High Similarity	NPC273578
0.8704	High Similarity	NPC475170
0.8701	High Similarity	NPC475360
0.8686	High Similarity	NPC170203
0.8683	High Similarity	NPC131557
0.8667	High Similarity	NPC284353
0.8663	High Similarity	NPC178737
0.8659	High Similarity	NPC308555
0.8659	High Similarity	NPC474514
0.8642	High Similarity	NPC85141
0.8639	High Similarity	NPC475865
0.8631	High Similarity	NPC319749
0.8623	High Similarity	NPC257914
0.8623	High Similarity	NPC238405
0.8623	High Similarity	NPC104459
0.8614	High Similarity	NPC474983
0.8606	High Similarity	NPC279930
0.8598	High Similarity	NPC104353
0.8598	High Similarity	NPC220577
0.8596	High Similarity	NPC79322
0.8588	High Similarity	NPC187923
0.858	High Similarity	NPC478199
0.858	High Similarity	NPC280778
0.8571	High Similarity	NPC477882
0.8571	High Similarity	NPC477880
0.8563	High Similarity	NPC258644
0.8554	High Similarity	NPC471746
0.8554	High Similarity	NPC254163
0.8545	High Similarity	NPC68882
0.8537	High Similarity	NPC210642
0.8537	High Similarity	NPC474975
0.8537	High Similarity	NPC13985
0.8529	High Similarity	NPC223006
0.8529	High Similarity	NPC272750
0.8529	High Similarity	NPC173729
0.8529	High Similarity	NPC469518
0.8529	High Similarity	NPC469475
0.8529	High Similarity	NPC134047
0.8519	High Similarity	NPC25496
0.8503	High Similarity	NPC155063
0.8488	Intermediate Similarity	NPC471180
0.8476	Intermediate Similarity	NPC316989
0.8476	Intermediate Similarity	NPC149505
0.8471	Intermediate Similarity	NPC302741
0.8471	Intermediate Similarity	NPC144557
0.8466	Intermediate Similarity	NPC477375
0.8466	Intermediate Similarity	NPC198129
0.8466	Intermediate Similarity	NPC327352
0.8466	Intermediate Similarity	NPC252281
0.8462	Intermediate Similarity	NPC74749
0.8462	Intermediate Similarity	NPC43971
0.8462	Intermediate Similarity	NPC139876
0.8462	Intermediate Similarity	NPC474770
0.8462	Intermediate Similarity	NPC19554
0.8457	Intermediate Similarity	NPC87295
0.8457	Intermediate Similarity	NPC474446
0.8448	Intermediate Similarity	NPC469506
0.8447	Intermediate Similarity	NPC475000
0.8447	Intermediate Similarity	NPC50696
0.8443	Intermediate Similarity	NPC188962
0.8443	Intermediate Similarity	NPC42871
0.8443	Intermediate Similarity	NPC202249
0.8434	Intermediate Similarity	NPC475116
0.8434	Intermediate Similarity	NPC477377
0.843	Intermediate Similarity	NPC320471
0.843	Intermediate Similarity	NPC118162
0.843	Intermediate Similarity	NPC83049
0.843	Intermediate Similarity	NPC475214
0.843	Intermediate Similarity	NPC113093
0.8415	Intermediate Similarity	NPC322426
0.8415	Intermediate Similarity	NPC477374
0.8415	Intermediate Similarity	NPC477376
0.8412	Intermediate Similarity	NPC34376
0.8405	Intermediate Similarity	NPC153620
0.8405	Intermediate Similarity	NPC24257
0.8402	Intermediate Similarity	NPC68619
0.8402	Intermediate Similarity	NPC15764
0.8402	Intermediate Similarity	NPC50430
0.84	Intermediate Similarity	NPC62640
0.8395	Intermediate Similarity	NPC474158
0.8393	Intermediate Similarity	NPC470625
0.8393	Intermediate Similarity	NPC29727
0.8391	Intermediate Similarity	NPC72249
0.8391	Intermediate Similarity	NPC91043
0.8383	Intermediate Similarity	NPC478213
0.8383	Intermediate Similarity	NPC57211
0.8383	Intermediate Similarity	NPC198461
0.8383	Intermediate Similarity	NPC312763
0.8383	Intermediate Similarity	NPC244371
0.8382	Intermediate Similarity	NPC311912
0.8373	Intermediate Similarity	NPC474170
0.8373	Intermediate Similarity	NPC477378
0.8373	Intermediate Similarity	NPC474388
0.8373	Intermediate Similarity	NPC472535
0.8373	Intermediate Similarity	NPC56184
0.8373	Intermediate Similarity	NPC473732
0.8373	Intermediate Similarity	NPC475229
0.8363	Intermediate Similarity	NPC76687
0.8363	Intermediate Similarity	NPC469512
0.8363	Intermediate Similarity	NPC19948
0.8354	Intermediate Similarity	NPC262804
0.8354	Intermediate Similarity	NPC117463
0.8354	Intermediate Similarity	NPC40654
0.8353	Intermediate Similarity	NPC63061
0.8353	Intermediate Similarity	NPC96593
0.8353	Intermediate Similarity	NPC119910
0.8353	Intermediate Similarity	NPC269906
0.8344	Intermediate Similarity	NPC193779
0.8344	Intermediate Similarity	NPC213482
0.8344	Intermediate Similarity	NPC321958
0.8344	Intermediate Similarity	NPC321696
0.8343	Intermediate Similarity	NPC19947
0.8343	Intermediate Similarity	NPC310206
0.8343	Intermediate Similarity	NPC471181
0.8343	Intermediate Similarity	NPC207584
0.8343	Intermediate Similarity	NPC475964
0.8333	Intermediate Similarity	NPC15743
0.8333	Intermediate Similarity	NPC34725
0.8333	Intermediate Similarity	NPC143092
0.8333	Intermediate Similarity	NPC241774
0.8333	Intermediate Similarity	NPC476180
0.8333	Intermediate Similarity	NPC88557
0.8333	Intermediate Similarity	NPC122623
0.8333	Intermediate Similarity	NPC276059
0.8333	Intermediate Similarity	NPC18211
0.8333	Intermediate Similarity	NPC474036
0.8324	Intermediate Similarity	NPC472895
0.8323	Intermediate Similarity	NPC292460
0.8323	Intermediate Similarity	NPC477960
0.8323	Intermediate Similarity	NPC176586
0.8323	Intermediate Similarity	NPC210354
0.8323	Intermediate Similarity	NPC477961
0.8323	Intermediate Similarity	NPC52623
0.8323	Intermediate Similarity	NPC153008
0.8323	Intermediate Similarity	NPC477962
0.8323	Intermediate Similarity	NPC40237
0.8323	Intermediate Similarity	NPC151423
0.8323	Intermediate Similarity	NPC148497
0.8315	Intermediate Similarity	NPC244903
0.8313	Intermediate Similarity	NPC177839
0.8305	Intermediate Similarity	NPC472384
0.8305	Intermediate Similarity	NPC472382
0.8305	Intermediate Similarity	NPC156635
0.8305	Intermediate Similarity	NPC154741
0.8305	Intermediate Similarity	NPC472380
0.8305	Intermediate Similarity	NPC296018
0.8305	Intermediate Similarity	NPC473713
0.8304	Intermediate Similarity	NPC309335
0.8304	Intermediate Similarity	NPC288149
0.8304	Intermediate Similarity	NPC296540
0.8303	Intermediate Similarity	NPC477698
0.8297	Intermediate Similarity	NPC201814
0.8295	Intermediate Similarity	NPC72455
0.8295	Intermediate Similarity	NPC4390
0.8294	Intermediate Similarity	NPC474043
0.8294	Intermediate Similarity	NPC125713
0.8294	Intermediate Similarity	NPC113055
0.8293	Intermediate Similarity	NPC65574
0.8293	Intermediate Similarity	NPC80230
0.8293	Intermediate Similarity	NPC304687
0.8293	Intermediate Similarity	NPC101755
0.8293	Intermediate Similarity	NPC104024
0.8286	Intermediate Similarity	NPC212748
0.8286	Intermediate Similarity	NPC475434
0.8284	Intermediate Similarity	NPC473323
0.8284	Intermediate Similarity	NPC257277
0.8284	Intermediate Similarity	NPC261484
0.8284	Intermediate Similarity	NPC237946
0.8284	Intermediate Similarity	NPC32373
0.8282	Intermediate Similarity	NPC327651
0.8282	Intermediate Similarity	NPC318286
0.8276	Intermediate Similarity	NPC149244
0.8276	Intermediate Similarity	NPC116745
0.8276	Intermediate Similarity	NPC215802
0.8276	Intermediate Similarity	NPC167231
0.8276	Intermediate Similarity	NPC76482
0.8276	Intermediate Similarity	NPC48640
0.8274	Intermediate Similarity	NPC186507
0.8272	Intermediate Similarity	NPC76415
0.8272	Intermediate Similarity	NPC218510

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 NPC474568 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	941
0.2-0.3	1936
0.3-0.4	2648
0.4-0.5	1887
0.5-0.6	835
0.6-0.7	398
0.7-0.8	102
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8529	High Similarity	NPD7184	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.8304	Intermediate Similarity	NPD7199	Phase 2
0.8284	Intermediate Similarity	NPD4967	Phase 2
0.8284	Intermediate Similarity	NPD4965	Approved
0.8284	Intermediate Similarity	NPD4966	Approved
0.8276	Intermediate Similarity	NPD3818	Discontinued
0.8246	Intermediate Similarity	NPD5494	Approved
0.8242	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6234	Discontinued
0.8146	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD37	Approved
0.807	Intermediate Similarity	NPD3882	Suspended
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7977	Intermediate Similarity	NPD919	Approved
0.7944	Intermediate Similarity	NPD7808	Phase 3
0.7933	Intermediate Similarity	NPD6797	Phase 2
0.7912	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3926	Phase 2
0.7889	Intermediate Similarity	NPD7251	Discontinued
0.7877	Intermediate Similarity	NPD7074	Phase 3
0.7865	Intermediate Similarity	NPD7228	Approved
0.7849	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7819	Suspended
0.7844	Intermediate Similarity	NPD6799	Approved
0.7821	Intermediate Similarity	NPD7054	Approved
0.7816	Intermediate Similarity	NPD7075	Discontinued
0.7809	Intermediate Similarity	NPD7473	Discontinued
0.7791	Intermediate Similarity	NPD1934	Approved
0.7791	Intermediate Similarity	NPD6801	Discontinued
0.7784	Intermediate Similarity	NPD1247	Approved
0.7778	Intermediate Similarity	NPD7472	Approved
0.7772	Intermediate Similarity	NPD8434	Phase 2
0.7765	Intermediate Similarity	NPD3751	Discontinued
0.7759	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6166	Phase 2
0.7753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6232	Discontinued
0.7738	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5844	Phase 1
0.7714	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD5402	Approved
0.7692	Intermediate Similarity	NPD7240	Approved
0.7644	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD2801	Approved
0.764	Intermediate Similarity	NPD3787	Discontinued
0.7636	Intermediate Similarity	NPD2796	Approved
0.7624	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6559	Discontinued
0.7576	Intermediate Similarity	NPD3748	Approved
0.7543	Intermediate Similarity	NPD1465	Phase 2
0.7541	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7472	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1512	Approved
0.7436	Intermediate Similarity	NPD5006	Approved
0.7436	Intermediate Similarity	NPD5005	Approved
0.7407	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD920	Approved
0.7394	Intermediate Similarity	NPD1933	Approved
0.7384	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3750	Approved
0.733	Intermediate Similarity	NPD7411	Suspended
0.7326	Intermediate Similarity	NPD1511	Approved
0.732	Intermediate Similarity	NPD4420	Approved
0.7318	Intermediate Similarity	NPD3749	Approved
0.7293	Intermediate Similarity	NPD8127	Discontinued
0.7283	Intermediate Similarity	NPD2532	Approved
0.7283	Intermediate Similarity	NPD2534	Approved
0.7283	Intermediate Similarity	NPD2533	Approved
0.7283	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4380	Phase 2
0.7257	Intermediate Similarity	NPD1653	Approved
0.7253	Intermediate Similarity	NPD7229	Phase 3
0.7251	Intermediate Similarity	NPD4628	Phase 3
0.7235	Intermediate Similarity	NPD1549	Phase 2
0.7235	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8313	Approved
0.7234	Intermediate Similarity	NPD8312	Approved
0.7219	Intermediate Similarity	NPD7685	Pre-registration
0.7213	Intermediate Similarity	NPD5242	Approved
0.7212	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6190	Approved
0.7207	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6959	Discontinued
0.7196	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1243	Approved
0.7186	Intermediate Similarity	NPD6355	Discontinued
0.7184	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7028	Phase 2
0.7174	Intermediate Similarity	NPD2403	Approved
0.7168	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7435	Discontinued
0.7119	Intermediate Similarity	NPD3226	Approved
0.7119	Intermediate Similarity	NPD7458	Discontinued
0.7111	Intermediate Similarity	NPD5353	Approved
0.7107	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2800	Approved
0.7081	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3705	Approved
0.7071	Intermediate Similarity	NPD4107	Approved
0.7059	Intermediate Similarity	NPD1510	Phase 2
0.7052	Intermediate Similarity	NPD4110	Phase 3
0.7052	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7680	Approved
0.7018	Intermediate Similarity	NPD6099	Approved
0.7018	Intermediate Similarity	NPD6100	Approved
0.7016	Intermediate Similarity	NPD8407	Phase 2
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.7005	Intermediate Similarity	NPD7799	Discontinued
0.6994	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6832	Phase 2
0.6985	Remote Similarity	NPD6779	Approved
0.6985	Remote Similarity	NPD6781	Approved
0.6985	Remote Similarity	NPD6777	Approved
0.6985	Remote Similarity	NPD6776	Approved
0.6985	Remote Similarity	NPD6782	Approved
0.6985	Remote Similarity	NPD6780	Approved
0.6985	Remote Similarity	NPD6778	Approved
0.6982	Remote Similarity	NPD447	Suspended
0.6978	Remote Similarity	NPD7768	Phase 2
0.6977	Remote Similarity	NPD1471	Phase 3
0.6977	Remote Similarity	NPD2346	Discontinued
0.6971	Remote Similarity	NPD8404	Phase 2
0.6963	Remote Similarity	NPD2971	Approved
0.6963	Remote Similarity	NPD2968	Approved
0.6961	Remote Similarity	NPD8455	Phase 2
0.6961	Remote Similarity	NPD8151	Discontinued
0.6959	Remote Similarity	NPD2799	Discontinued
0.6957	Remote Similarity	NPD17	Approved
0.6954	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4482	Phase 3
0.6949	Remote Similarity	NPD6273	Approved
0.6947	Remote Similarity	NPD6764	Approved
0.6947	Remote Similarity	NPD6765	Approved
0.6947	Remote Similarity	NPD8368	Discontinued
0.6944	Remote Similarity	NPD6385	Approved
0.6944	Remote Similarity	NPD6386	Approved
0.6943	Remote Similarity	NPD8150	Discontinued
0.6927	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7874	Approved
0.6923	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD1240	Approved
0.6919	Remote Similarity	NPD2974	Approved
0.6919	Remote Similarity	NPD2975	Approved
0.6919	Remote Similarity	NPD2973	Approved
0.6919	Remote Similarity	NPD2438	Suspended
0.6914	Remote Similarity	NPD3887	Approved
0.6909	Remote Similarity	NPD3266	Approved
0.6909	Remote Similarity	NPD3267	Approved
0.69	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4580	Approved
0.6893	Remote Similarity	NPD3146	Approved
0.6893	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7296	Approved
0.6882	Remote Similarity	NPD230	Phase 1
0.6882	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7697	Approved
0.6881	Remote Similarity	NPD7696	Phase 3
0.6881	Remote Similarity	NPD7698	Approved
0.6864	Remote Similarity	NPD6233	Phase 2
0.6864	Remote Similarity	NPD8032	Phase 2
0.686	Remote Similarity	NPD7033	Discontinued
0.6854	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8319	Approved
0.6847	Remote Similarity	NPD7870	Phase 2
0.6847	Remote Similarity	NPD7871	Phase 2
0.6847	Remote Similarity	NPD8320	Phase 1
0.6845	Remote Similarity	NPD7095	Approved
0.6842	Remote Similarity	NPD1607	Approved
0.6839	Remote Similarity	NPD2897	Discontinued
0.6829	Remote Similarity	NPD1608	Approved
0.6824	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1613	Approved
0.6821	Remote Similarity	NPD1551	Phase 2
0.6821	Remote Similarity	NPD2935	Discontinued
0.6806	Remote Similarity	NPD5953	Discontinued
0.6805	Remote Similarity	NPD3268	Approved
0.6804	Remote Similarity	NPD6785	Approved
0.6804	Remote Similarity	NPD6784	Approved
0.68	Remote Similarity	NPD6674	Discontinued
0.6791	Remote Similarity	NPD5711	Approved
0.6791	Remote Similarity	NPD5710	Approved
0.6782	Remote Similarity	NPD2494	Approved
0.6782	Remote Similarity	NPD5762	Approved
0.6782	Remote Similarity	NPD5763	Approved
0.6782	Remote Similarity	NPD7266	Discontinued
0.6782	Remote Similarity	NPD2493	Approved
0.6776	Remote Similarity	NPD5761	Phase 2
0.6776	Remote Similarity	NPD5760	Phase 2
0.6766	Remote Similarity	NPD2798	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