NPASS Compound

Structure

NPC474647 OpenBabel07101719522D 37 40 0 0 1 0 0 0 0 0999 V2000 -3.0918 -5.7850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5171 -5.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3026 -2.6254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3510 -3.6108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2835 2.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4768 0.2813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1549 -6.0536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4613 -1.5275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5929 -0.1506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2026 -2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9692 0.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5463 -1.9279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4539 -5.3766 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.4123 -2.2290 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9238 -2.7349 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0480 -0.9586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6414 -2.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0466 -2.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1657 0.7253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6414 -1.4406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2244 -2.8084 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0466 -1.4406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2026 -0.9533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2917 -1.0876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6897 -4.4310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9027 -0.3284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3656 -0.7884 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1935 0.7933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6437 -1.9964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6265 -4.1624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5507 0.5804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7107 1.5333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8658 -0.4779 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 1.9735 -2.7163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9735 -1.1394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9886 -3.7540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 13 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 16 2 0 0 0 0 9 19 1 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 11 27 1 0 0 0 0 11 34 1 0 0 0 0 12 35 1 0 0 0 0 12 36 1 0 0 0 0 13 25 1 0 0 0 0 14 3 1 6 0 0 0 14 15 1 0 0 0 0 15 4 1 6 0 0 0 15 21 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 18 35 1 0 0 0 0 19 28 2 0 0 0 0 19 32 1 0 0 0 0 20 23 2 0 0 0 0 20 27 1 0 0 0 0 21 37 1 6 0 0 0 22 23 1 0 0 0 0 22 36 1 0 0 0 0 23 34 1 0 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 24 29 2 0 0 0 0 25 30 2 0 0 0 0 25 37 1 0 0 0 0 26 31 2 0 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.2
Volume:	508.133
LogP:	4.069
LogD:	4.216
LogS:	-4.535
# Rotatable Bonds:	9
TPSA:	123.66
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.241
Synthetic Accessibility Score:	4.923
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.972
MDCK Permeability:	2.126688923453912e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.083

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.265
Plasma Protein Binding (PPB):	96.14826202392578%
Volume Distribution (VD):	1.051
Pgp-substrate:	4.929592609405518%

ADMET: Metabolism

CYP1A2-inhibitor:	0.122
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.964
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.946
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.291
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	4.196
Half-life (T1/2):	0.224

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.723
Drug-inuced Liver Injury (DILI):	0.315
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.268
Maximum Recommended Daily Dose:	0.239
Skin Sensitization:	0.031
Carcinogencity:	0.089
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.488

Download Data

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

Natural Product: NPC474647

Natural Product ID:	NPC474647
*Common Name:**	Taiwanschirin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JXMLIDFLHAGBOD-PYWBWJTHSA-N
Standard InCHI:	InChI=1S/C27H32O10/c1-7-13(2)25(30)37-21-15(4)14(3)8-16(9-19(28)32-5)27(24(29)26(31)33-6)11-34-23-20(27)17(21)10-18-22(23)36-12-35-18/h9-10,13-15,21H,7-8,11-12H2,1-6H3/b16-9-/t13?,14-,15-,21-,27?/m1/s1
SMILES:	CCC(C)C(=O)OC1C(C(CC(=CC(=O)OC)C2(COC3=C2C1=CC4=C3OCO4)C(=O)C(=O)OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477934
PubChem CID:	44584768
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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[544672]
NPT27	Others	Unspecified		Activity	=	14.1	IU/L	PMID[544672]
NPT27	Others	Unspecified		Activity	=	14.8	IU/L	PMID[544672]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Activity	=	43.0	%	PMID[544672]

☑ 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 NPC474647 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	450
0.1-0.2	1627
0.2-0.3	3838
0.3-0.4	8333
0.4-0.5	9956
0.5-0.6	4680
0.6-0.7	7177
0.7-0.8	6338
0.8-0.85	265
0.85-0.9	17
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC475953
0.9747	High Similarity	NPC42230
0.9623	High Similarity	NPC474948
0.9506	High Similarity	NPC474568
0.9114	High Similarity	NPC117154
0.8938	High Similarity	NPC477380
0.8896	High Similarity	NPC61141
0.8882	High Similarity	NPC477885
0.8827	High Similarity	NPC325122
0.8812	High Similarity	NPC348849
0.8812	High Similarity	NPC178195
0.8742	High Similarity	NPC303519
0.8679	High Similarity	NPC475170
0.8634	High Similarity	NPC475116
0.8634	High Similarity	NPC474514
0.858	High Similarity	NPC477883
0.858	High Similarity	NPC273578
0.8571	High Similarity	NPC473732
0.8563	High Similarity	NPC477884
0.8529	High Similarity	NPC178737
0.8503	High Similarity	NPC475865
0.85	High Similarity	NPC85141
0.8494	Intermediate Similarity	NPC209411
0.8494	Intermediate Similarity	NPC239890
0.8494	Intermediate Similarity	NPC191352
0.8494	Intermediate Similarity	NPC258322
0.8491	Intermediate Similarity	NPC25496
0.8481	Intermediate Similarity	NPC27106
0.848	Intermediate Similarity	NPC477881
0.8476	Intermediate Similarity	NPC301897
0.8476	Intermediate Similarity	NPC29727
0.8462	Intermediate Similarity	NPC471180
0.8457	Intermediate Similarity	NPC220577
0.8457	Intermediate Similarity	NPC104353
0.8457	Intermediate Similarity	NPC470380
0.8447	Intermediate Similarity	NPC316989
0.8438	Intermediate Similarity	NPC327352
0.8438	Intermediate Similarity	NPC477375
0.8438	Intermediate Similarity	NPC252281
0.8438	Intermediate Similarity	NPC198129
0.8434	Intermediate Similarity	NPC63061
0.8434	Intermediate Similarity	NPC131557
0.8428	Intermediate Similarity	NPC321958
0.8428	Intermediate Similarity	NPC474446
0.8428	Intermediate Similarity	NPC87295
0.8428	Intermediate Similarity	NPC321696
0.8405	Intermediate Similarity	NPC308555
0.8395	Intermediate Similarity	NPC474975
0.8395	Intermediate Similarity	NPC210642
0.8395	Intermediate Similarity	NPC13985
0.8393	Intermediate Similarity	NPC469475
0.8393	Intermediate Similarity	NPC469518
0.8385	Intermediate Similarity	NPC322426
0.8385	Intermediate Similarity	NPC477376
0.8385	Intermediate Similarity	NPC477374
0.8383	Intermediate Similarity	NPC319749
0.8373	Intermediate Similarity	NPC257914
0.8373	Intermediate Similarity	NPC238405
0.8373	Intermediate Similarity	NPC104459
0.8365	Intermediate Similarity	NPC318286
0.8365	Intermediate Similarity	NPC327651
0.8362	Intermediate Similarity	NPC475360
0.8343	Intermediate Similarity	NPC187923
0.8343	Intermediate Similarity	NPC170203
0.8333	Intermediate Similarity	NPC477880
0.8333	Intermediate Similarity	NPC149505
0.8333	Intermediate Similarity	NPC469512
0.8333	Intermediate Similarity	NPC477882
0.8323	Intermediate Similarity	NPC209229
0.8323	Intermediate Similarity	NPC474770
0.8314	Intermediate Similarity	NPC471181
0.8313	Intermediate Similarity	NPC258644
0.8303	Intermediate Similarity	NPC188962
0.8303	Intermediate Similarity	NPC42871
0.8303	Intermediate Similarity	NPC79998
0.8303	Intermediate Similarity	NPC284353
0.8303	Intermediate Similarity	NPC471746
0.8303	Intermediate Similarity	NPC202249
0.8303	Intermediate Similarity	NPC254163
0.8302	Intermediate Similarity	NPC143092
0.8302	Intermediate Similarity	NPC18211
0.8302	Intermediate Similarity	NPC475000
0.8302	Intermediate Similarity	NPC50696
0.8302	Intermediate Similarity	NPC326144
0.8294	Intermediate Similarity	NPC475214
0.8294	Intermediate Similarity	NPC472895
0.8291	Intermediate Similarity	NPC151423
0.8291	Intermediate Similarity	NPC40237
0.8272	Intermediate Similarity	NPC477698
0.8263	Intermediate Similarity	NPC279732
0.8253	Intermediate Similarity	NPC473323
0.8253	Intermediate Similarity	NPC474983
0.8253	Intermediate Similarity	NPC155063
0.8246	Intermediate Similarity	NPC79322
0.8242	Intermediate Similarity	NPC473425
0.8242	Intermediate Similarity	NPC198461
0.8242	Intermediate Similarity	NPC279930
0.8242	Intermediate Similarity	NPC312763
0.8239	Intermediate Similarity	NPC76415
0.8239	Intermediate Similarity	NPC474966
0.8239	Intermediate Similarity	NPC218510
0.8235	Intermediate Similarity	NPC222531
0.8232	Intermediate Similarity	NPC56184
0.8225	Intermediate Similarity	NPC76687
0.8225	Intermediate Similarity	NPC280778
0.8225	Intermediate Similarity	NPC478199
0.8214	Intermediate Similarity	NPC139876
0.8214	Intermediate Similarity	NPC119910
0.8204	Intermediate Similarity	NPC19947
0.8204	Intermediate Similarity	NPC207584
0.8204	Intermediate Similarity	NPC220462
0.8199	Intermediate Similarity	NPC193779
0.8199	Intermediate Similarity	NPC213482
0.8198	Intermediate Similarity	NPC476180
0.8193	Intermediate Similarity	NPC238834
0.8187	Intermediate Similarity	NPC15743
0.8187	Intermediate Similarity	NPC118162
0.8187	Intermediate Similarity	NPC474036
0.8187	Intermediate Similarity	NPC83049
0.8187	Intermediate Similarity	NPC320471
0.8187	Intermediate Similarity	NPC92693
0.8187	Intermediate Similarity	NPC475109
0.8187	Intermediate Similarity	NPC218841
0.8187	Intermediate Similarity	NPC113093
0.8182	Intermediate Similarity	NPC53669
0.8182	Intermediate Similarity	NPC297271
0.8182	Intermediate Similarity	NPC16791
0.8182	Intermediate Similarity	NPC477962
0.8182	Intermediate Similarity	NPC126405
0.8182	Intermediate Similarity	NPC477961
0.8182	Intermediate Similarity	NPC477377
0.8182	Intermediate Similarity	NPC68882
0.8182	Intermediate Similarity	NPC217708
0.8182	Intermediate Similarity	NPC77237
0.8182	Intermediate Similarity	NPC308739
0.8182	Intermediate Similarity	NPC24562
0.8182	Intermediate Similarity	NPC477960
0.8176	Intermediate Similarity	NPC46180
0.8176	Intermediate Similarity	NPC272750
0.8176	Intermediate Similarity	NPC176586
0.8176	Intermediate Similarity	NPC173729
0.8176	Intermediate Similarity	NPC223006
0.8176	Intermediate Similarity	NPC134047
0.8176	Intermediate Similarity	NPC210354
0.8171	Intermediate Similarity	NPC224472
0.8171	Intermediate Similarity	NPC164082
0.8166	Intermediate Similarity	NPC309335
0.8166	Intermediate Similarity	NPC296540
0.8155	Intermediate Similarity	NPC15764
0.8155	Intermediate Similarity	NPC474043
0.8155	Intermediate Similarity	NPC50430
0.815	Intermediate Similarity	NPC475434
0.815	Intermediate Similarity	NPC91043
0.8148	Intermediate Similarity	NPC65574
0.8148	Intermediate Similarity	NPC80230
0.8148	Intermediate Similarity	NPC101755
0.8148	Intermediate Similarity	NPC304687
0.8148	Intermediate Similarity	NPC153620
0.8148	Intermediate Similarity	NPC104024
0.8148	Intermediate Similarity	NPC24257
0.8144	Intermediate Similarity	NPC237946
0.8144	Intermediate Similarity	NPC257277
0.8144	Intermediate Similarity	NPC150227
0.8144	Intermediate Similarity	NPC32373
0.8137	Intermediate Similarity	NPC184702
0.8137	Intermediate Similarity	NPC474158
0.8133	Intermediate Similarity	NPC57211
0.8133	Intermediate Similarity	NPC136757
0.8133	Intermediate Similarity	NPC473664
0.8125	Intermediate Similarity	NPC297985
0.8125	Intermediate Similarity	NPC474288
0.8121	Intermediate Similarity	NPC477699
0.8121	Intermediate Similarity	NPC474170
0.8121	Intermediate Similarity	NPC474388
0.8121	Intermediate Similarity	NPC477378
0.8121	Intermediate Similarity	NPC472535
0.8121	Intermediate Similarity	NPC475229
0.8118	Intermediate Similarity	NPC469575
0.8118	Intermediate Similarity	NPC144557
0.8118	Intermediate Similarity	NPC414831
0.8118	Intermediate Similarity	NPC302741
0.811	Intermediate Similarity	NPC473989
0.8107	Intermediate Similarity	NPC96593
0.8107	Intermediate Similarity	NPC74749
0.8107	Intermediate Similarity	NPC43971
0.8107	Intermediate Similarity	NPC19554
0.8103	Intermediate Similarity	NPC475964
0.8103	Intermediate Similarity	NPC469506
0.8098	Intermediate Similarity	NPC262804
0.8098	Intermediate Similarity	NPC117463
0.8098	Intermediate Similarity	NPC40654
0.8095	Intermediate Similarity	NPC190020
0.8095	Intermediate Similarity	NPC84935
0.8095	Intermediate Similarity	NPC77679
0.8092	Intermediate Similarity	NPC476771
0.809	Intermediate Similarity	NPC475148
0.809	Intermediate Similarity	NPC475656
0.8084	Intermediate Similarity	NPC34725
0.8084	Intermediate Similarity	NPC122623
0.8084	Intermediate Similarity	NPC199926

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 NPC474647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	994
0.2-0.3	2209
0.3-0.4	2582
0.4-0.5	1730
0.5-0.6	799
0.6-0.7	357
0.7-0.8	96
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8284	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD4967	Phase 2
0.8144	Intermediate Similarity	NPD4965	Approved
0.8144	Intermediate Similarity	NPD4966	Approved
0.8084	Intermediate Similarity	NPD3817	Phase 2
0.8059	Intermediate Similarity	NPD7199	Phase 2
0.8047	Intermediate Similarity	NPD6234	Discontinued
0.7964	Intermediate Similarity	NPD37	Approved
0.7931	Intermediate Similarity	NPD3818	Discontinued
0.791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5494	Approved
0.7879	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD919	Approved
0.7829	Intermediate Similarity	NPD7228	Approved
0.7824	Intermediate Similarity	NPD3882	Suspended
0.7809	Intermediate Similarity	NPD7808	Phase 3
0.7753	Intermediate Similarity	NPD7251	Discontinued
0.774	Intermediate Similarity	NPD7074	Phase 3
0.7738	Intermediate Similarity	NPD6599	Discontinued
0.7697	Intermediate Similarity	NPD6797	Phase 2
0.7684	Intermediate Similarity	NPD7054	Approved
0.768	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7473	Discontinued
0.7657	Intermediate Similarity	NPD3926	Phase 2
0.7654	Intermediate Similarity	NPD7240	Approved
0.7644	Intermediate Similarity	NPD1247	Approved
0.764	Intermediate Similarity	NPD7472	Approved
0.7602	Intermediate Similarity	NPD7819	Suspended
0.7602	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6799	Approved
0.7572	Intermediate Similarity	NPD7075	Discontinued
0.7545	Intermediate Similarity	NPD2534	Approved
0.7545	Intermediate Similarity	NPD2532	Approved
0.7545	Intermediate Similarity	NPD2533	Approved
0.7544	Intermediate Similarity	NPD1934	Approved
0.7514	Intermediate Similarity	NPD6166	Phase 2
0.7514	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6232	Discontinued
0.7486	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD8434	Phase 2
0.7442	Intermediate Similarity	NPD6801	Discontinued
0.7401	Intermediate Similarity	NPD3787	Discontinued
0.7399	Intermediate Similarity	NPD2801	Approved
0.7399	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5844	Phase 1
0.7371	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5402	Approved
0.7355	Intermediate Similarity	NPD3705	Approved
0.7333	Intermediate Similarity	NPD3751	Discontinued
0.733	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1465	Phase 2
0.7287	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2796	Approved
0.7268	Intermediate Similarity	NPD6559	Discontinued
0.7257	Intermediate Similarity	NPD5353	Approved
0.7251	Intermediate Similarity	NPD920	Approved
0.7222	Intermediate Similarity	NPD2403	Approved
0.7216	Intermediate Similarity	NPD5006	Approved
0.7216	Intermediate Similarity	NPD5005	Approved
0.7196	Intermediate Similarity	NPD7296	Approved
0.7193	Intermediate Similarity	NPD1512	Approved
0.716	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5403	Approved
0.7151	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD2800	Approved
0.7143	Intermediate Similarity	NPD1243	Approved
0.7135	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5401	Approved
0.7134	Intermediate Similarity	NPD6355	Discontinued
0.7111	Intermediate Similarity	NPD7229	Phase 3
0.711	Intermediate Similarity	NPD1653	Approved
0.7108	Intermediate Similarity	NPD3748	Approved
0.7101	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4420	Approved
0.709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1511	Approved
0.7066	Intermediate Similarity	NPD6100	Approved
0.7066	Intermediate Similarity	NPD6099	Approved
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6959	Discontinued
0.7035	Intermediate Similarity	NPD3146	Approved
0.7035	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1933	Approved
0.703	Intermediate Similarity	NPD447	Suspended
0.703	Intermediate Similarity	NPD230	Phase 1
0.7018	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8312	Approved
0.7005	Intermediate Similarity	NPD8313	Approved
0.7	Intermediate Similarity	NPD4628	Phase 3
0.7	Intermediate Similarity	NPD4110	Phase 3
0.7	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7411	Suspended
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6983	Remote Similarity	NPD3749	Approved
0.6978	Remote Similarity	NPD5242	Approved
0.6936	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7028	Phase 2
0.6932	Remote Similarity	NPD4380	Phase 2
0.6923	Remote Similarity	NPD5711	Approved
0.6923	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5710	Approved
0.6919	Remote Similarity	NPD7680	Approved
0.6919	Remote Similarity	NPD7435	Discontinued
0.6901	Remote Similarity	NPD3750	Approved
0.6901	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1549	Phase 2
0.6875	Remote Similarity	NPD7458	Discontinued
0.686	Remote Similarity	NPD6190	Approved
0.6853	Remote Similarity	NPD4107	Approved
0.6848	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6674	Discontinued
0.6832	Remote Similarity	NPD8151	Discontinued
0.6829	Remote Similarity	NPD6832	Phase 2
0.6825	Remote Similarity	NPD2971	Approved
0.6825	Remote Similarity	NPD2968	Approved
0.6824	Remote Similarity	NPD5763	Approved
0.6824	Remote Similarity	NPD5762	Approved
0.6816	Remote Similarity	NPD8455	Phase 2
0.6807	Remote Similarity	NPD8032	Phase 2
0.6805	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6385	Approved
0.6798	Remote Similarity	NPD6386	Approved
0.6792	Remote Similarity	NPD17	Approved
0.6789	Remote Similarity	NPD8407	Phase 2
0.6786	Remote Similarity	NPD2973	Approved
0.6786	Remote Similarity	NPD6651	Approved
0.6786	Remote Similarity	NPD2975	Approved
0.6786	Remote Similarity	NPD2974	Approved
0.678	Remote Similarity	NPD3226	Approved
0.6774	Remote Similarity	NPD7799	Discontinued
0.6771	Remote Similarity	NPD6842	Approved
0.6771	Remote Similarity	NPD6841	Approved
0.6771	Remote Similarity	NPD6843	Phase 3
0.6768	Remote Similarity	NPD4580	Approved
0.6766	Remote Similarity	NPD4060	Phase 1
0.6765	Remote Similarity	NPD2438	Suspended
0.6757	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6798	Discontinued
0.6744	Remote Similarity	NPD2654	Approved
0.674	Remote Similarity	NPD7768	Phase 2
0.6739	Remote Similarity	NPD7315	Approved
0.6734	Remote Similarity	NPD4482	Phase 3
0.6725	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6002	Phase 3
0.6725	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6005	Phase 3
0.6725	Remote Similarity	NPD1471	Phase 3
0.6725	Remote Similarity	NPD6004	Phase 3
0.672	Remote Similarity	NPD8368	Discontinued
0.6716	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7874	Approved
0.6706	Remote Similarity	NPD2799	Discontinued
0.6706	Remote Similarity	NPD1510	Phase 2
0.6705	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD5090	Approved
0.6704	Remote Similarity	NPD5089	Approved
0.6687	Remote Similarity	NPD7095	Approved
0.6683	Remote Similarity	NPD6781	Approved
0.6683	Remote Similarity	NPD6780	Approved
0.6683	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6777	Approved
0.6683	Remote Similarity	NPD8404	Phase 2
0.6683	Remote Similarity	NPD6778	Approved
0.6683	Remote Similarity	NPD6782	Approved
0.6683	Remote Similarity	NPD6776	Approved
0.6683	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD1240	Approved
0.665	Remote Similarity	NPD2493	Approved
0.665	Remote Similarity	NPD2494	Approved
0.6648	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1296	Phase 2
0.6646	Remote Similarity	NPD3266	Approved
0.6646	Remote Similarity	NPD3267	Approved
0.6636	Remote Similarity	NPD6625	Approved
0.6635	Remote Similarity	NPD7907	Approved
0.6634	Remote Similarity	NPD7870	Phase 2
0.6634	Remote Similarity	NPD8319	Approved
0.6634	Remote Similarity	NPD4583	Approved
0.6634	Remote Similarity	NPD4582	Approved
0.6634	Remote Similarity	NPD7871	Phase 2
0.6634	Remote Similarity	NPD8320	Phase 1

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