NPASS Compound

Structure

NPC470075 OpenBabel07101718232D 38 43 0 0 1 0 0 0 0 0999 V2000 -2.9577 0.5902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6379 -0.1428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4044 1.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4022 -1.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0932 -0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3972 -2.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7170 -1.4888 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 4.6894 -2.3430 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 4.3804 -1.3920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7624 0.5102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3944 -2.1472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0495 -0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6629 -0.3653 0.0000 C 0 0 0 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 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4533 1.4612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 5.6676 -2.5509 0.0000 O 0 0 0 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8944 -3.0132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0277 -0.8567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6613 2.4394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 0.3023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9577 -1.3209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 6 7 1 0 0 0 0 6 16 2 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 9 22 1 0 0 0 0 10 26 1 0 0 0 0 11 29 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 31 1 0 0 0 0 15 29 1 0 0 0 0 15 30 1 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 17 32 1 1 0 0 0 18 27 1 6 0 0 0 18 28 1 0 0 0 0 19 26 1 1 0 0 0 19 30 1 0 0 0 0 20 27 1 1 0 0 0 20 33 1 0 0 0 0 21 28 1 6 0 0 0 21 37 1 0 0 0 0 22 34 2 0 0 0 0 22 38 1 0 0 0 0 23 25 1 0 0 0 0 23 29 1 6 0 0 0 24 35 2 0 0 0 0 24 37 1 0 0 0 0 25 38 1 0 0 0 0 26 27 1 1 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 28 36 1 0 0 0 0 29 30 1 1 0 0 0 30 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.29
Volume:	535.873
LogP:	2.4
LogD:	1.204
LogS:	-3.808
# Rotatable Bonds:	3
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	6.732
Fsp3:	0.8
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:	-5.413
MDCK Permeability:	4.961945887771435e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.099
20% Bioavailability (F20%):	0.936
30% Bioavailability (F30%):	0.543

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.572
Plasma Protein Binding (PPB):	25.40420913696289%
Volume Distribution (VD):	0.38
Pgp-substrate:	54.27678680419922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.29
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.303
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	3.86
Half-life (T1/2):	0.529

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.86
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.714
Carcinogencity:	0.553
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC470075

Natural Product ID:	NPC470075
*Common Name:**	Angustifodilactone A
IUPAC Name:	n.a.
Synonyms:	Angustifodilactone A
Standard InCHIKey:	AGZMSHUZAZHKKN-LDUYZNKBSA-N
Standard InCHI:	InChI=1S/C30H42O8/c1-25(2)23-17(32)12-19-26(3)10-8-18(28(5,36)21-7-6-16(14-31)24(35)37-21)27(26,4)20(33)13-30(19)15-29(23,30)11-9-22(34)38-25/h6,9,11,17-21,23,31-33,36H,7-8,10,12-15H2,1-5H3/t17-,18-,19-,20-,21+,23-,26-,27-,28+,29+,30-/m0/s1
SMILES:	CC1(C2C(CC3C4(CCC(C4(C(CC35C2(C5)C=CC(=O)O1)O)C)C(C)(C6CC=C(C(=O)O6)CO)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669430
PubChem CID:	51003490
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	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
EC50	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	=	178.2	ug.mL-1	PMID[512495]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	13.3	ug.mL-1	PMID[512495]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	13.4	n.a.	PMID[512495]

☑ 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 NPC470075 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	230
0.1-0.2	1383
0.2-0.3	4176
0.3-0.4	7392
0.4-0.5	13552
0.5-0.6	7107
0.6-0.7	6233
0.7-0.8	2440
0.8-0.85	142
0.85-0.9	35
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC470076
0.9009	High Similarity	NPC216665
0.8962	High Similarity	NPC297617
0.8957	High Similarity	NPC23786
0.8957	High Similarity	NPC470265
0.887	High Similarity	NPC67569
0.8839	High Similarity	NPC43213
0.8718	High Similarity	NPC469789
0.8609	High Similarity	NPC50774
0.8609	High Similarity	NPC709
0.8571	High Similarity	NPC293112
0.8532	High Similarity	NPC473543
0.8522	High Similarity	NPC20302
0.8522	High Similarity	NPC140055
0.8522	High Similarity	NPC286528
0.8522	High Similarity	NPC167606
0.8487	Intermediate Similarity	NPC8369
0.8487	Intermediate Similarity	NPC8374
0.8462	Intermediate Similarity	NPC474370
0.844	Intermediate Similarity	NPC473523
0.844	Intermediate Similarity	NPC474124
0.8426	Intermediate Similarity	NPC475617
0.8417	Intermediate Similarity	NPC473635
0.8403	Intermediate Similarity	NPC11895
0.839	Intermediate Similarity	NPC46570
0.8376	Intermediate Similarity	NPC211093
0.8376	Intermediate Similarity	NPC473839
0.8376	Intermediate Similarity	NPC264954
0.8376	Intermediate Similarity	NPC473636
0.8376	Intermediate Similarity	NPC77689
0.8376	Intermediate Similarity	NPC278681
0.8374	Intermediate Similarity	NPC231240
0.8362	Intermediate Similarity	NPC470493
0.8362	Intermediate Similarity	NPC134430
0.8362	Intermediate Similarity	NPC473656
0.8362	Intermediate Similarity	NPC312824
0.8362	Intermediate Similarity	NPC183580
0.8362	Intermediate Similarity	NPC470492
0.8362	Intermediate Similarity	NPC475809
0.8361	Intermediate Similarity	NPC473593
0.8349	Intermediate Similarity	NPC109195
0.8349	Intermediate Similarity	NPC476471
0.8349	Intermediate Similarity	NPC475038
0.8349	Intermediate Similarity	NPC475344
0.8348	Intermediate Similarity	NPC147912
0.8348	Intermediate Similarity	NPC67259
0.8333	Intermediate Similarity	NPC172154
0.8333	Intermediate Similarity	NPC81736
0.8333	Intermediate Similarity	NPC38855
0.8319	Intermediate Similarity	NPC88326
0.8319	Intermediate Similarity	NPC107493
0.8319	Intermediate Similarity	NPC238850
0.8319	Intermediate Similarity	NPC170538
0.8319	Intermediate Similarity	NPC269642
0.8319	Intermediate Similarity	NPC153700
0.8306	Intermediate Similarity	NPC316915
0.8305	Intermediate Similarity	NPC112936
0.8304	Intermediate Similarity	NPC88701
0.8291	Intermediate Similarity	NPC16701
0.8261	Intermediate Similarity	NPC264153
0.8261	Intermediate Similarity	NPC122056
0.8257	Intermediate Similarity	NPC11974
0.8246	Intermediate Similarity	NPC71680
0.8246	Intermediate Similarity	NPC262083
0.8246	Intermediate Similarity	NPC255401
0.8246	Intermediate Similarity	NPC471484
0.8246	Intermediate Similarity	NPC284162
0.8241	Intermediate Similarity	NPC218107
0.8235	Intermediate Similarity	NPC4021
0.8235	Intermediate Similarity	NPC159456
0.823	Intermediate Similarity	NPC284828
0.823	Intermediate Similarity	NPC173905
0.823	Intermediate Similarity	NPC472216
0.823	Intermediate Similarity	NPC5475
0.8224	Intermediate Similarity	NPC195366
0.8224	Intermediate Similarity	NPC114743
0.822	Intermediate Similarity	NPC35171
0.822	Intermediate Similarity	NPC213761
0.8211	Intermediate Similarity	NPC134902
0.8211	Intermediate Similarity	NPC476966
0.8205	Intermediate Similarity	NPC185287
0.8205	Intermediate Similarity	NPC157380
0.8198	Intermediate Similarity	NPC475585
0.8198	Intermediate Similarity	NPC474550
0.8198	Intermediate Similarity	NPC473577
0.8182	Intermediate Similarity	NPC3381
0.8182	Intermediate Similarity	NPC470972
0.8182	Intermediate Similarity	NPC472552
0.8174	Intermediate Similarity	NPC241477
0.8174	Intermediate Similarity	NPC4573
0.8174	Intermediate Similarity	NPC470063
0.8174	Intermediate Similarity	NPC90952
0.8174	Intermediate Similarity	NPC236217
0.8174	Intermediate Similarity	NPC269530
0.8174	Intermediate Similarity	NPC277769
0.8165	Intermediate Similarity	NPC473510
0.8165	Intermediate Similarity	NPC230546
0.816	Intermediate Similarity	NPC469673
0.8158	Intermediate Similarity	NPC15551
0.8158	Intermediate Similarity	NPC181298
0.8151	Intermediate Similarity	NPC268530
0.8151	Intermediate Similarity	NPC154491
0.8151	Intermediate Similarity	NPC251226
0.8148	Intermediate Similarity	NPC210337
0.8145	Intermediate Similarity	NPC254823
0.8145	Intermediate Similarity	NPC196921
0.8145	Intermediate Similarity	NPC220757
0.8142	Intermediate Similarity	NPC181994
0.8142	Intermediate Similarity	NPC472218
0.8142	Intermediate Similarity	NPC475263
0.8142	Intermediate Similarity	NPC472217
0.8142	Intermediate Similarity	NPC472219
0.8136	Intermediate Similarity	NPC475372
0.8136	Intermediate Similarity	NPC186525
0.8125	Intermediate Similarity	NPC220217
0.8125	Intermediate Similarity	NPC475290
0.8125	Intermediate Similarity	NPC119855
0.8125	Intermediate Similarity	NPC470980
0.812	Intermediate Similarity	NPC207637
0.8108	Intermediate Similarity	NPC473694
0.8108	Intermediate Similarity	NPC471938
0.8108	Intermediate Similarity	NPC475623
0.8108	Intermediate Similarity	NPC475334
0.8108	Intermediate Similarity	NPC474822
0.8108	Intermediate Similarity	NPC472821
0.8103	Intermediate Similarity	NPC171126
0.8095	Intermediate Similarity	NPC476823
0.8091	Intermediate Similarity	NPC472554
0.8083	Intermediate Similarity	NPC312481
0.808	Intermediate Similarity	NPC34963
0.8073	Intermediate Similarity	NPC124512
0.8073	Intermediate Similarity	NPC159763
0.8073	Intermediate Similarity	NPC278386
0.807	Intermediate Similarity	NPC475065
0.807	Intermediate Similarity	NPC475274
0.8067	Intermediate Similarity	NPC312536
0.8067	Intermediate Similarity	NPC475520
0.8067	Intermediate Similarity	NPC475041
0.8067	Intermediate Similarity	NPC473274
0.8067	Intermediate Similarity	NPC472667
0.8067	Intermediate Similarity	NPC5292
0.8065	Intermediate Similarity	NPC35109
0.8065	Intermediate Similarity	NPC231529
0.8056	Intermediate Similarity	NPC54248
0.8056	Intermediate Similarity	NPC88009
0.8056	Intermediate Similarity	NPC288970
0.8056	Intermediate Similarity	NPC276103
0.8053	Intermediate Similarity	NPC329048
0.8053	Intermediate Similarity	NPC330011
0.8053	Intermediate Similarity	NPC471205
0.8053	Intermediate Similarity	NPC473586
0.8053	Intermediate Similarity	NPC187435
0.8053	Intermediate Similarity	NPC67321
0.8051	Intermediate Similarity	NPC55296
0.8051	Intermediate Similarity	NPC469684
0.8051	Intermediate Similarity	NPC203862
0.8051	Intermediate Similarity	NPC476959
0.8049	Intermediate Similarity	NPC42399
0.8037	Intermediate Similarity	NPC476186
0.8037	Intermediate Similarity	NPC119562
0.8037	Intermediate Similarity	NPC279410
0.8036	Intermediate Similarity	NPC471937
0.8036	Intermediate Similarity	NPC475335
0.8036	Intermediate Similarity	NPC121518
0.8036	Intermediate Similarity	NPC80809
0.8036	Intermediate Similarity	NPC161775
0.8036	Intermediate Similarity	NPC288502
0.8036	Intermediate Similarity	NPC201144
0.8036	Intermediate Similarity	NPC103298
0.8036	Intermediate Similarity	NPC475331
0.8036	Intermediate Similarity	NPC181104
0.8033	Intermediate Similarity	NPC470494
0.8018	Intermediate Similarity	NPC471914
0.8017	Intermediate Similarity	NPC191620
0.8017	Intermediate Similarity	NPC44537
0.8016	Intermediate Similarity	NPC476097
0.8016	Intermediate Similarity	NPC327664
0.8016	Intermediate Similarity	NPC470427
0.8016	Intermediate Similarity	NPC58029
0.8	Intermediate Similarity	NPC476961
0.8	Intermediate Similarity	NPC472214
0.8	Intermediate Similarity	NPC29133
0.8	Intermediate Similarity	NPC103491
0.8	Intermediate Similarity	NPC177047
0.8	Intermediate Similarity	NPC79579
0.8	Intermediate Similarity	NPC241935
0.8	Intermediate Similarity	NPC135369
0.8	Intermediate Similarity	NPC472215
0.8	Intermediate Similarity	NPC251680
0.8	Intermediate Similarity	NPC475885
0.8	Intermediate Similarity	NPC279478
0.7984	Intermediate Similarity	NPC245094
0.7984	Intermediate Similarity	NPC473620
0.7983	Intermediate Similarity	NPC124676
0.7983	Intermediate Similarity	NPC288679
0.7983	Intermediate Similarity	NPC146280
0.7983	Intermediate Similarity	NPC153440
0.7982	Intermediate Similarity	NPC38948
0.7982	Intermediate Similarity	NPC73911
0.7982	Intermediate Similarity	NPC475418

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 NPC470075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1468
0.2-0.3	3792
0.3-0.4	2466
0.4-0.5	742
0.5-0.6	258
0.6-0.7	182
0.7-0.8	49
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8522	High Similarity	NPD7115	Discovery
0.8073	Intermediate Similarity	NPD4225	Approved
0.8	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7639	Approved
0.7934	Intermediate Similarity	NPD7503	Approved
0.7909	Intermediate Similarity	NPD7638	Approved
0.7833	Intermediate Similarity	NPD7328	Approved
0.7833	Intermediate Similarity	NPD7327	Approved
0.7787	Intermediate Similarity	NPD8033	Approved
0.7769	Intermediate Similarity	NPD7516	Approved
0.7768	Intermediate Similarity	NPD5344	Discontinued
0.7705	Intermediate Similarity	NPD6319	Approved
0.7705	Intermediate Similarity	NPD8294	Approved
0.7705	Intermediate Similarity	NPD8377	Approved
0.7642	Intermediate Similarity	NPD8296	Approved
0.7642	Intermediate Similarity	NPD8380	Approved
0.7642	Intermediate Similarity	NPD8335	Approved
0.7642	Intermediate Similarity	NPD8379	Approved
0.7642	Intermediate Similarity	NPD8378	Approved
0.7638	Intermediate Similarity	NPD7319	Approved
0.7542	Intermediate Similarity	NPD6371	Approved
0.754	Intermediate Similarity	NPD7507	Approved
0.7521	Intermediate Similarity	NPD6686	Approved
0.7458	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD8297	Approved
0.7391	Intermediate Similarity	NPD7632	Discontinued
0.7368	Intermediate Similarity	NPD6648	Approved
0.7364	Intermediate Similarity	NPD7637	Suspended
0.7355	Intermediate Similarity	NPD4632	Approved
0.7323	Intermediate Similarity	NPD7492	Approved
0.728	Intermediate Similarity	NPD6054	Approved
0.7273	Intermediate Similarity	NPD7838	Discovery
0.7266	Intermediate Similarity	NPD6616	Approved
0.725	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7604	Phase 2
0.7227	Intermediate Similarity	NPD6899	Approved
0.7227	Intermediate Similarity	NPD6881	Approved
0.7209	Intermediate Similarity	NPD7078	Approved
0.719	Intermediate Similarity	NPD6650	Approved
0.719	Intermediate Similarity	NPD6649	Approved
0.7165	Intermediate Similarity	NPD6370	Approved
0.7154	Intermediate Similarity	NPD7736	Approved
0.7143	Intermediate Similarity	NPD5697	Approved
0.7131	Intermediate Similarity	NPD6882	Approved
0.7131	Intermediate Similarity	NPD6053	Discontinued
0.7107	Intermediate Similarity	NPD6883	Approved
0.7107	Intermediate Similarity	NPD4634	Approved
0.7107	Intermediate Similarity	NPD7290	Approved
0.7107	Intermediate Similarity	NPD7102	Approved
0.7087	Intermediate Similarity	NPD6016	Approved
0.7087	Intermediate Similarity	NPD6015	Approved
0.7083	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD6675	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.7049	Intermediate Similarity	NPD6869	Approved
0.7049	Intermediate Similarity	NPD6847	Approved
0.7049	Intermediate Similarity	NPD8130	Phase 1
0.7049	Intermediate Similarity	NPD6617	Approved
0.704	Intermediate Similarity	NPD6009	Approved
0.7031	Intermediate Similarity	NPD5988	Approved
0.7025	Intermediate Similarity	NPD6373	Approved
0.7025	Intermediate Similarity	NPD6013	Approved
0.7025	Intermediate Similarity	NPD6012	Approved
0.7025	Intermediate Similarity	NPD6014	Approved
0.7025	Intermediate Similarity	NPD6372	Approved
0.7008	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7524	Approved
0.6964	Remote Similarity	NPD6698	Approved
0.6964	Remote Similarity	NPD46	Approved
0.6953	Remote Similarity	NPD5983	Phase 2
0.6953	Remote Similarity	NPD8513	Phase 3
0.6949	Remote Similarity	NPD5211	Phase 2
0.6947	Remote Similarity	NPD8293	Discontinued
0.6942	Remote Similarity	NPD7320	Approved
0.6942	Remote Similarity	NPD6011	Approved
0.6935	Remote Similarity	NPD8133	Approved
0.6917	Remote Similarity	NPD6008	Approved
0.6881	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6336	Discontinued
0.686	Remote Similarity	NPD6412	Phase 2
0.686	Remote Similarity	NPD5701	Approved
0.6842	Remote Similarity	NPD6399	Phase 3
0.6838	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5141	Approved
0.6822	Remote Similarity	NPD8515	Approved
0.6822	Remote Similarity	NPD8517	Approved
0.6822	Remote Similarity	NPD8516	Approved
0.6822	Remote Similarity	NPD7525	Registered
0.6789	Remote Similarity	NPD6695	Phase 3
0.678	Remote Similarity	NPD5285	Approved
0.678	Remote Similarity	NPD5286	Approved
0.678	Remote Similarity	NPD4696	Approved
0.6754	Remote Similarity	NPD6079	Approved
0.6752	Remote Similarity	NPD6084	Phase 2
0.6752	Remote Similarity	NPD6083	Phase 2
0.6726	Remote Similarity	NPD6051	Approved
0.6718	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.664	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5174	Approved
0.6612	Remote Similarity	NPD5175	Approved
0.661	Remote Similarity	NPD4755	Approved
0.6609	Remote Similarity	NPD7983	Approved
0.6606	Remote Similarity	NPD6902	Approved
0.6589	Remote Similarity	NPD6335	Approved
0.6583	Remote Similarity	NPD5223	Approved
0.6581	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5328	Approved
0.6567	Remote Similarity	NPD8074	Phase 3
0.6565	Remote Similarity	NPD6921	Approved
0.6562	Remote Similarity	NPD6274	Approved
0.6552	Remote Similarity	NPD5778	Approved
0.6552	Remote Similarity	NPD5779	Approved
0.6552	Remote Similarity	NPD4202	Approved
0.6549	Remote Similarity	NPD7750	Discontinued
0.6549	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4729	Approved
0.6532	Remote Similarity	NPD4730	Approved
0.6525	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5221	Approved
0.6525	Remote Similarity	NPD5222	Approved
0.6519	Remote Similarity	NPD6033	Approved
0.6514	Remote Similarity	NPD6931	Approved
0.6514	Remote Similarity	NPD7514	Phase 3
0.6514	Remote Similarity	NPD6930	Phase 2
0.6512	Remote Similarity	NPD6317	Approved
0.6512	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4700	Approved
0.6496	Remote Similarity	NPD7260	Phase 2
0.6496	Remote Similarity	NPD7748	Approved
0.648	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5173	Approved
0.6471	Remote Similarity	NPD7902	Approved
0.6466	Remote Similarity	NPD8034	Phase 2
0.6466	Remote Similarity	NPD8035	Phase 2
0.6466	Remote Similarity	NPD7515	Phase 2
0.6462	Remote Similarity	NPD6313	Approved
0.6462	Remote Similarity	NPD6314	Approved
0.646	Remote Similarity	NPD3618	Phase 1
0.6446	Remote Similarity	NPD4159	Approved
0.6441	Remote Similarity	NPD5695	Phase 3
0.6441	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6868	Approved
0.6429	Remote Similarity	NPD5250	Approved
0.6429	Remote Similarity	NPD5247	Approved
0.6429	Remote Similarity	NPD4786	Approved
0.6429	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5249	Phase 3
0.6429	Remote Similarity	NPD5251	Approved
0.6429	Remote Similarity	NPD5248	Approved
0.6422	Remote Similarity	NPD6929	Approved
0.6417	Remote Similarity	NPD5696	Approved
0.6396	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD4768	Approved
0.6371	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD7332	Phase 2
0.6355	Remote Similarity	NPD7339	Approved
0.6355	Remote Similarity	NPD6942	Approved
0.6348	Remote Similarity	NPD5737	Approved
0.6348	Remote Similarity	NPD6672	Approved
0.633	Remote Similarity	NPD7145	Approved
0.6327	Remote Similarity	NPD7625	Phase 1
0.6325	Remote Similarity	NPD5693	Phase 1
0.6325	Remote Similarity	NPD7087	Discontinued
0.6325	Remote Similarity	NPD6411	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD6909	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD7521	Approved
0.6316	Remote Similarity	NPD6908	Approved
0.6316	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5956	Approved
0.6303	Remote Similarity	NPD4629	Approved
0.6303	Remote Similarity	NPD5210	Approved
0.6296	Remote Similarity	NPD6933	Approved
0.6293	Remote Similarity	NPD4753	Phase 2
0.6288	Remote Similarity	NPD4522	Approved
0.6273	Remote Similarity	NPD4195	Approved
0.627	Remote Similarity	NPD5128	Approved
0.6261	Remote Similarity	NPD4251	Approved
0.6261	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD5216	Approved
0.625	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD4697	Phase 3

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