NPASS Compound

Structure

NPC474948 OpenBabel07101718242D 34 38 0 0 1 0 0 0 0 0999 V2000 0.2894 5.4165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7894 2.8184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3909 2.3597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1736 3.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9819 -0.7216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7894 4.5505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8717 1.0388 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 -2.1447 1.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1392 -0.9903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2894 3.6844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6249 1.7169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0777 0.0000 C 0 0 2 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 -1.1744 1.3996 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 -2.8394 0.9222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8988 0.4384 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 -0.7106 1.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5637 -0.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5935 -0.2810 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 -0.7106 3.6844 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 0.6249 -2.0824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.2216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2106 4.5505 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 -1.1240 -1.1639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8388 0.9571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3928 -0.5982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2106 2.8184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 12 1 0 0 0 0 5 30 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 8 17 2 0 0 0 0 9 16 2 0 0 0 0 9 18 1 0 0 0 0 10 31 1 0 0 0 0 11 32 1 0 0 0 0 11 33 1 0 0 0 0 12 25 1 0 0 0 0 13 3 1 6 0 0 0 13 14 1 0 0 0 0 14 4 1 6 0 0 0 14 21 1 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 30 1 0 0 0 0 18 22 2 0 0 0 0 18 32 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 20 27 2 0 0 0 0 21 34 1 6 0 0 0 22 23 1 0 0 0 0 22 33 1 0 0 0 0 23 31 1 0 0 0 0 24 26 1 0 0 0 0 24 28 2 0 0 0 0 25 29 2 0 0 0 0 25 34 1 0 0 0 0 26 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.16
Volume:	462.063
LogP:	3.595
LogD:	3.589
LogS:	-4.637
# Rotatable Bonds:	4
TPSA:	97.36
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	5.321
Fsp3:	0.423
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.843
MDCK Permeability:	1.36889366331161e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.621

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	91.22258758544922%
Volume Distribution (VD):	0.938
Pgp-substrate:	6.424836158752441%

ADMET: Metabolism

CYP1A2-inhibitor:	0.227
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.975
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.961
CYP2C9-substrate:	0.154
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.965
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	5.224
Half-life (T1/2):	0.23

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.849
Drug-inuced Liver Injury (DILI):	0.228
AMES Toxicity:	0.247
Rat Oral Acute Toxicity:	0.536
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.446
Carcinogencity:	0.689
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC474948

Natural Product ID:	NPC474948
*Common Name:**	Interiotherin D
IUPAC Name:	n.a.
Synonyms:	Interiotherin D
Standard InCHIKey:	PFTANZOUWVSEQC-ZEZBFVHVSA-N
Standard InCHI:	InChI=1S/C26H26O8/c1-6-12(2)25(29)34-21-14(4)13(3)7-15-8-17(30-5)20(27)24(28)26(15)10-31-23-19(26)16(21)9-18-22(23)33-11-32-18/h6-9,13-14,21H,10-11H2,1-5H3/b12-6-,15-7-/t13-,14-,21-,26+/m1/s1
SMILES:	CC=C(C)C(=O)OC1C(C(C=C2C=C(C(=O)C(=O)C23COC4=C3C1=CC5=C4OCO5)OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489756
PubChem CID:	10050185
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
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350139]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[8946749]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14102	Kadsura interior	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	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[503836]
NPT2	Others	Unspecified		Activity	=	11.5	%	PMID[503836]
NPT2	Others	Unspecified		Activity	=	55.8	%	PMID[503836]
NPT2	Others	Unspecified		Activity	=	75.0	%	PMID[503836]
NPT2	Others	Unspecified		Activity	=	94.8	%	PMID[503836]

☑ 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 NPC474948 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	463
0.1-0.2	1640
0.2-0.3	3739
0.3-0.4	7998
0.4-0.5	10075
0.5-0.6	4796
0.6-0.7	7036
0.7-0.8	6616
0.8-0.85	291
0.85-0.9	26
0.9-0.95	11
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC42230
0.9747	High Similarity	NPC475953
0.963	High Similarity	NPC474568
0.9623	High Similarity	NPC474647
0.9241	High Similarity	NPC117154
0.8902	High Similarity	NPC61141
0.8834	High Similarity	NPC325122
0.8827	High Similarity	NPC477380
0.882	High Similarity	NPC348849
0.882	High Similarity	NPC178195
0.8805	High Similarity	NPC475170
0.8773	High Similarity	NPC477885
0.8671	High Similarity	NPC474446
0.8642	High Similarity	NPC475116
0.8634	High Similarity	NPC303519
0.8616	High Similarity	NPC25496
0.8614	High Similarity	NPC209411
0.8614	High Similarity	NPC239890
0.8589	High Similarity	NPC273578
0.858	High Similarity	NPC473732
0.858	High Similarity	NPC104353
0.8563	High Similarity	NPC170203
0.8544	High Similarity	NPC50696
0.8538	High Similarity	NPC178737
0.8528	High Similarity	NPC474514
0.8528	High Similarity	NPC308555
0.8512	High Similarity	NPC475865
0.8509	High Similarity	NPC85141
0.8503	High Similarity	NPC191352
0.8503	High Similarity	NPC258322
0.8485	Intermediate Similarity	NPC301897
0.848	Intermediate Similarity	NPC477883
0.8475	Intermediate Similarity	NPC475360
0.8466	Intermediate Similarity	NPC220577
0.8462	Intermediate Similarity	NPC477884
0.8462	Intermediate Similarity	NPC187923
0.8443	Intermediate Similarity	NPC131557
0.8443	Intermediate Similarity	NPC474770
0.8438	Intermediate Similarity	NPC87295
0.8428	Intermediate Similarity	NPC15743
0.8428	Intermediate Similarity	NPC475000
0.8424	Intermediate Similarity	NPC188962
0.8424	Intermediate Similarity	NPC284353
0.8424	Intermediate Similarity	NPC42871
0.8424	Intermediate Similarity	NPC202249
0.8424	Intermediate Similarity	NPC254163
0.8412	Intermediate Similarity	NPC472895
0.8405	Intermediate Similarity	NPC13985
0.8405	Intermediate Similarity	NPC474975
0.8405	Intermediate Similarity	NPC210642
0.8402	Intermediate Similarity	NPC469518
0.8402	Intermediate Similarity	NPC469475
0.8383	Intermediate Similarity	NPC104459
0.8383	Intermediate Similarity	NPC238405
0.8383	Intermediate Similarity	NPC257914
0.8382	Intermediate Similarity	NPC477881
0.8375	Intermediate Similarity	NPC27106
0.8373	Intermediate Similarity	NPC474983
0.8365	Intermediate Similarity	NPC474966
0.8364	Intermediate Similarity	NPC279930
0.8363	Intermediate Similarity	NPC471180
0.8354	Intermediate Similarity	NPC470380
0.8344	Intermediate Similarity	NPC149505
0.8344	Intermediate Similarity	NPC316989
0.8343	Intermediate Similarity	NPC76687
0.8343	Intermediate Similarity	NPC478199
0.8333	Intermediate Similarity	NPC198129
0.8333	Intermediate Similarity	NPC252281
0.8333	Intermediate Similarity	NPC139876
0.8333	Intermediate Similarity	NPC477375
0.8333	Intermediate Similarity	NPC327352
0.8323	Intermediate Similarity	NPC213482
0.8323	Intermediate Similarity	NPC220462
0.8323	Intermediate Similarity	NPC258644
0.8323	Intermediate Similarity	NPC193779
0.8313	Intermediate Similarity	NPC471746
0.8304	Intermediate Similarity	NPC475109
0.8303	Intermediate Similarity	NPC68882
0.8302	Intermediate Similarity	NPC46180
0.8302	Intermediate Similarity	NPC40237
0.8302	Intermediate Similarity	NPC151423
0.8294	Intermediate Similarity	NPC223006
0.8294	Intermediate Similarity	NPC272750
0.8294	Intermediate Similarity	NPC173729
0.8294	Intermediate Similarity	NPC134047
0.8291	Intermediate Similarity	NPC278076
0.8284	Intermediate Similarity	NPC319749
0.8282	Intermediate Similarity	NPC477374
0.8282	Intermediate Similarity	NPC322426
0.8282	Intermediate Similarity	NPC477698
0.8282	Intermediate Similarity	NPC477376
0.8274	Intermediate Similarity	NPC279732
0.8274	Intermediate Similarity	NPC15764
0.8272	Intermediate Similarity	NPC24257
0.8272	Intermediate Similarity	NPC153620
0.8263	Intermediate Similarity	NPC155063
0.8263	Intermediate Similarity	NPC29727
0.8261	Intermediate Similarity	NPC474158
0.8261	Intermediate Similarity	NPC184702
0.8261	Intermediate Similarity	NPC232883
0.8256	Intermediate Similarity	NPC79322
0.8253	Intermediate Similarity	NPC57211
0.8253	Intermediate Similarity	NPC312763
0.8253	Intermediate Similarity	NPC198461
0.825	Intermediate Similarity	NPC297985
0.8242	Intermediate Similarity	NPC56184
0.8239	Intermediate Similarity	NPC477880
0.8239	Intermediate Similarity	NPC51681
0.8239	Intermediate Similarity	NPC477882
0.8235	Intermediate Similarity	NPC144557
0.8235	Intermediate Similarity	NPC469512
0.8235	Intermediate Similarity	NPC280778
0.8235	Intermediate Similarity	NPC302741
0.8232	Intermediate Similarity	NPC177830
0.8225	Intermediate Similarity	NPC119910
0.8225	Intermediate Similarity	NPC63061
0.8225	Intermediate Similarity	NPC74749
0.8225	Intermediate Similarity	NPC19554
0.8225	Intermediate Similarity	NPC43971
0.8221	Intermediate Similarity	NPC40654
0.8221	Intermediate Similarity	NPC117463
0.8221	Intermediate Similarity	NPC262804
0.8218	Intermediate Similarity	NPC475964
0.8218	Intermediate Similarity	NPC471181
0.8217	Intermediate Similarity	NPC209229
0.8214	Intermediate Similarity	NPC207584
0.8214	Intermediate Similarity	NPC19947
0.821	Intermediate Similarity	NPC321958
0.821	Intermediate Similarity	NPC321696
0.8204	Intermediate Similarity	NPC79998
0.8204	Intermediate Similarity	NPC476363
0.8199	Intermediate Similarity	NPC92693
0.8199	Intermediate Similarity	NPC18211
0.8199	Intermediate Similarity	NPC218841
0.8199	Intermediate Similarity	NPC143092
0.8198	Intermediate Similarity	NPC476277
0.8198	Intermediate Similarity	NPC475214
0.8198	Intermediate Similarity	NPC113093
0.8193	Intermediate Similarity	NPC477962
0.8193	Intermediate Similarity	NPC477960
0.8193	Intermediate Similarity	NPC52623
0.8193	Intermediate Similarity	NPC477961
0.8187	Intermediate Similarity	NPC476822
0.8187	Intermediate Similarity	NPC210354
0.8187	Intermediate Similarity	NPC176586
0.8182	Intermediate Similarity	NPC164082
0.8182	Intermediate Similarity	NPC163002
0.8177	Intermediate Similarity	NPC201814
0.8176	Intermediate Similarity	NPC34376
0.8176	Intermediate Similarity	NPC309335
0.8176	Intermediate Similarity	NPC296540
0.8171	Intermediate Similarity	NPC472567
0.8171	Intermediate Similarity	NPC62640
0.8166	Intermediate Similarity	NPC68619
0.8166	Intermediate Similarity	NPC475095
0.8166	Intermediate Similarity	NPC50430
0.8166	Intermediate Similarity	NPC474043
0.8161	Intermediate Similarity	NPC91043
0.8161	Intermediate Similarity	NPC72249
0.816	Intermediate Similarity	NPC80230
0.816	Intermediate Similarity	NPC304687
0.816	Intermediate Similarity	NPC101755
0.816	Intermediate Similarity	NPC65574
0.816	Intermediate Similarity	NPC104024
0.8155	Intermediate Similarity	NPC150227
0.8155	Intermediate Similarity	NPC473323
0.8155	Intermediate Similarity	NPC261484
0.8155	Intermediate Similarity	NPC32373
0.8155	Intermediate Similarity	NPC237946
0.8155	Intermediate Similarity	NPC470625
0.8155	Intermediate Similarity	NPC164244
0.8148	Intermediate Similarity	NPC327651
0.8148	Intermediate Similarity	NPC318286
0.8144	Intermediate Similarity	NPC136757
0.8144	Intermediate Similarity	NPC244371
0.8144	Intermediate Similarity	NPC478213
0.814	Intermediate Similarity	NPC222531
0.8137	Intermediate Similarity	NPC218510
0.8137	Intermediate Similarity	NPC474288
0.8137	Intermediate Similarity	NPC76415
0.8133	Intermediate Similarity	NPC477699
0.8133	Intermediate Similarity	NPC474170
0.8133	Intermediate Similarity	NPC472535
0.8133	Intermediate Similarity	NPC474388
0.8133	Intermediate Similarity	NPC279061
0.8129	Intermediate Similarity	NPC469575
0.8129	Intermediate Similarity	NPC19948
0.8118	Intermediate Similarity	NPC218471
0.8118	Intermediate Similarity	NPC96593
0.8118	Intermediate Similarity	NPC239818
0.8118	Intermediate Similarity	NPC313368
0.8118	Intermediate Similarity	NPC269906
0.8114	Intermediate Similarity	NPC38438
0.8114	Intermediate Similarity	NPC469506
0.811	Intermediate Similarity	NPC52106
0.811	Intermediate Similarity	NPC473428
0.8107	Intermediate Similarity	NPC474990
0.8107	Intermediate Similarity	NPC84935
0.8107	Intermediate Similarity	NPC77679
0.8107	Intermediate Similarity	NPC190020

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 NPC474948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	990
0.2-0.3	2152
0.3-0.4	2579
0.4-0.5	1769
0.5-0.6	802
0.6-0.7	366
0.7-0.8	96
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8294	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD4967	Phase 2
0.8155	Intermediate Similarity	NPD4966	Approved
0.8155	Intermediate Similarity	NPD4965	Approved
0.8095	Intermediate Similarity	NPD3817	Phase 2
0.807	Intermediate Similarity	NPD7199	Phase 2
0.8059	Intermediate Similarity	NPD6234	Discontinued
0.8046	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD37	Approved
0.7953	Intermediate Similarity	NPD919	Approved
0.7941	Intermediate Similarity	NPD3882	Suspended
0.7921	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6599	Discontinued
0.7771	Intermediate Similarity	NPD3926	Phase 2
0.7759	Intermediate Similarity	NPD1247	Approved
0.774	Intermediate Similarity	NPD7228	Approved
0.7722	Intermediate Similarity	NPD7808	Phase 3
0.7711	Intermediate Similarity	NPD6799	Approved
0.7709	Intermediate Similarity	NPD6797	Phase 2
0.7692	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7251	Discontinued
0.7654	Intermediate Similarity	NPD7074	Phase 3
0.763	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7819	Suspended
0.7598	Intermediate Similarity	NPD7054	Approved
0.7586	Intermediate Similarity	NPD7075	Discontinued
0.7584	Intermediate Similarity	NPD7473	Discontinued
0.7569	Intermediate Similarity	NPD7240	Approved
0.7558	Intermediate Similarity	NPD1934	Approved
0.7558	Intermediate Similarity	NPD6801	Discontinued
0.7556	Intermediate Similarity	NPD7472	Approved
0.7543	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD3751	Discontinued
0.7528	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6166	Phase 2
0.7514	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5402	Approved
0.7459	Intermediate Similarity	NPD8434	Phase 2
0.7456	Intermediate Similarity	NPD2533	Approved
0.7456	Intermediate Similarity	NPD2534	Approved
0.7456	Intermediate Similarity	NPD2532	Approved
0.7418	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD3787	Discontinued
0.7414	Intermediate Similarity	NPD1465	Phase 2
0.7414	Intermediate Similarity	NPD2801	Approved
0.7414	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2796	Approved
0.7377	Intermediate Similarity	NPD6559	Discontinued
0.7368	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD2403	Approved
0.7333	Intermediate Similarity	NPD3748	Approved
0.7302	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5353	Approved
0.7267	Intermediate Similarity	NPD5403	Approved
0.7262	Intermediate Similarity	NPD1243	Approved
0.7262	Intermediate Similarity	NPD2800	Approved
0.7261	Intermediate Similarity	NPD3705	Approved
0.7251	Intermediate Similarity	NPD5401	Approved
0.7251	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5005	Approved
0.7231	Intermediate Similarity	NPD5006	Approved
0.7225	Intermediate Similarity	NPD1653	Approved
0.7219	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1512	Approved
0.7196	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8127	Discontinued
0.7152	Intermediate Similarity	NPD1933	Approved
0.7151	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4628	Phase 3
0.7118	Intermediate Similarity	NPD3750	Approved
0.7113	Intermediate Similarity	NPD4420	Approved
0.7102	Intermediate Similarity	NPD7411	Suspended
0.7095	Intermediate Similarity	NPD3749	Approved
0.7093	Intermediate Similarity	NPD1511	Approved
0.7088	Intermediate Similarity	NPD5242	Approved
0.7074	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6959	Discontinued
0.7067	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6355	Discontinued
0.7048	Intermediate Similarity	NPD447	Suspended
0.7048	Intermediate Similarity	NPD230	Phase 1
0.7045	Intermediate Similarity	NPD7028	Phase 2
0.7045	Intermediate Similarity	NPD4380	Phase 2
0.7041	Intermediate Similarity	NPD4107	Approved
0.7033	Intermediate Similarity	NPD7229	Phase 3
0.7031	Intermediate Similarity	NPD7296	Approved
0.7021	Intermediate Similarity	NPD8313	Approved
0.7021	Intermediate Similarity	NPD8312	Approved
0.7018	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4110	Phase 3
0.7005	Intermediate Similarity	NPD7685	Pre-registration
0.7	Intermediate Similarity	NPD1549	Phase 2
0.699	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6100	Approved
0.6982	Remote Similarity	NPD6099	Approved
0.6977	Remote Similarity	NPD6190	Approved
0.6954	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3146	Approved
0.6941	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5711	Approved
0.694	Remote Similarity	NPD5710	Approved
0.6935	Remote Similarity	NPD7435	Discontinued
0.6919	Remote Similarity	NPD4482	Phase 3
0.6893	Remote Similarity	NPD7458	Discontinued
0.6893	Remote Similarity	NPD3226	Approved
0.6882	Remote Similarity	NPD7799	Discontinued
0.6865	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7680	Approved
0.6848	Remote Similarity	NPD6832	Phase 2
0.6847	Remote Similarity	NPD8151	Discontinued
0.6842	Remote Similarity	NPD2971	Approved
0.6842	Remote Similarity	NPD2968	Approved
0.6842	Remote Similarity	NPD1471	Phase 3
0.6825	Remote Similarity	NPD6765	Approved
0.6825	Remote Similarity	NPD6764	Approved
0.6824	Remote Similarity	NPD1510	Phase 2
0.6824	Remote Similarity	NPD2799	Discontinued
0.6824	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6386	Approved
0.6816	Remote Similarity	NPD6385	Approved
0.6813	Remote Similarity	NPD17	Approved
0.6806	Remote Similarity	NPD8407	Phase 2
0.6805	Remote Similarity	NPD6651	Approved
0.6802	Remote Similarity	NPD2975	Approved
0.6802	Remote Similarity	NPD2973	Approved
0.6802	Remote Similarity	NPD2974	Approved
0.6788	Remote Similarity	NPD6841	Approved
0.6788	Remote Similarity	NPD6843	Phase 3
0.6788	Remote Similarity	NPD6842	Approved
0.6786	Remote Similarity	NPD1240	Approved
0.6786	Remote Similarity	NPD4060	Phase 1
0.6784	Remote Similarity	NPD2438	Suspended
0.6784	Remote Similarity	NPD4580	Approved
0.6784	Remote Similarity	NPD6780	Approved
0.6784	Remote Similarity	NPD6777	Approved
0.6784	Remote Similarity	NPD6781	Approved
0.6784	Remote Similarity	NPD6782	Approved
0.6784	Remote Similarity	NPD6776	Approved
0.6784	Remote Similarity	NPD6779	Approved
0.6784	Remote Similarity	NPD6778	Approved
0.6782	Remote Similarity	NPD3887	Approved
0.6774	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6798	Discontinued
0.6766	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6674	Discontinued
0.6763	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7768	Phase 2
0.6746	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2346	Discontinued
0.6744	Remote Similarity	NPD5762	Approved
0.6744	Remote Similarity	NPD5763	Approved
0.674	Remote Similarity	NPD8455	Phase 2
0.6737	Remote Similarity	NPD8368	Discontinued
0.6736	Remote Similarity	NPD8150	Discontinued
0.6732	Remote Similarity	NPD7874	Approved
0.6732	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7907	Approved
0.6726	Remote Similarity	NPD8032	Phase 2
0.6723	Remote Similarity	NPD6273	Approved
0.6723	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5089	Approved
0.6722	Remote Similarity	NPD5090	Approved
0.6706	Remote Similarity	NPD1607	Approved
0.67	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8404	Phase 2
0.6687	Remote Similarity	NPD1608	Approved
0.6686	Remote Similarity	NPD1551	Phase 2
0.6686	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2935	Discontinued
0.6684	Remote Similarity	NPD6784	Approved
0.6684	Remote Similarity	NPD6785	Approved
0.6684	Remote Similarity	NPD5953	Discontinued
0.6683	Remote Similarity	NPD7696	Phase 3
0.6683	Remote Similarity	NPD7697	Approved
0.6683	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD1296	Phase 2
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD2654	Approved
0.6667	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD7315	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD2494	Approved
0.6651	Remote Similarity	NPD8366	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