NPASS Compound

Structure

NPC305808 OpenBabel07101718322D 32 37 0 0 1 0 0 0 0 0999 V2000 -2.4271 -2.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8966 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7226 -1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7045 -2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -2.1756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3559 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2219 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0880 2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2219 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8200 2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8200 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0880 1.3090 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 4.2219 3.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -1.9945 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 2 15 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 25 1 0 0 0 0 9 20 1 0 0 0 0 10 19 1 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 31 1 0 0 0 0 14 1 1 6 0 0 0 15 24 1 0 0 0 0 15 27 1 6 0 0 0 16 9 1 6 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 26 1 1 0 0 0 18 25 1 1 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 28 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 30 2 0 0 0 0 23 11 1 1 0 0 0 23 24 1 0 0 0 0 23 32 1 0 0 0 0 24 25 1 1 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 27 8 1 1 0 0 0 27 31 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.3
Volume:	465.524
LogP:	3.957
LogD:	3.927
LogS:	-4.136
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.589
Synthetic Accessibility Score:	5.621
Fsp3:	0.963
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.77
MDCK Permeability:	1.8315642591915093e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.571
30% Bioavailability (F30%):	0.433

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.632
Plasma Protein Binding (PPB):	72.25728607177734%
Volume Distribution (VD):	1.165
Pgp-substrate:	11.836138725280762%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.55
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.746
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.158
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	13.521
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.953
Human Hepatotoxicity (H-HT):	0.284
Drug-inuced Liver Injury (DILI):	0.847
AMES Toxicity:	0.122
Rat Oral Acute Toxicity:	0.252
Maximum Recommended Daily Dose:	0.438
Skin Sensitization:	0.912
Carcinogencity:	0.574
Eye Corrosion:	0.02
Eye Irritation:	0.126
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC305808

Natural Product ID:	NPC305808
*Common Name:**	Porrigenin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BTSHHJQHTVNSLW-SLEDWXMVSA-N
Standard InCHI:	InChI=1S/C27H42O5/c1-14-5-8-27(31-13-14)15(2)24-23(32-27)11-18-16-9-20(28)19-10-21(29)22(30)12-26(19,4)17(16)6-7-25(18,24)3/h14-21,23-24,28-29H,5-13H2,1-4H3/t14-,15+,16-,17+,18+,19-,20-,21-,23+,24+,25+,26-,27-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5C[C@H]([C@H]6C[C@H](C(=O)C[C@]6(C)[C@H]5CC[C@]34C)O)O)O2)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466376
PubChem CID:	44566820
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
NPO33365	allium porrum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358643]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	12

Activity Type	# Activity
Cell Line	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2486	Cell Line	IGR-1	Homo sapiens	IC50	=	823.0	ug.mL-1	PMID[546633]
NPT2486	Cell Line	IGR-1	Homo sapiens	IC50	=	330.0	ug.mL-1	PMID[546633]
NPT2486	Cell Line	IGR-1	Homo sapiens	IC50	=	45.0	ug.mL-1	PMID[546633]
NPT1886	Cell Line	J774	Mus musculus	IC50	=	552.0	ug.mL-1	PMID[546633]
NPT1886	Cell Line	J774	Mus musculus	IC50	=	111.0	ug.mL-1	PMID[546633]
NPT1886	Cell Line	J774	Mus musculus	IC50	=	51.0	ug.mL-1	PMID[546633]
NPT3470	Cell Line	WEHI-164	Mus musculus	IC50	=	655.0	ug.mL-1	PMID[546633]
NPT3470	Cell Line	WEHI-164	Mus musculus	IC50	=	344.0	ug.mL-1	PMID[546633]
NPT3470	Cell Line	WEHI-164	Mus musculus	IC50	=	92.0	ug.mL-1	PMID[546633]
NPT168	Cell Line	P388	Mus musculus	IC50	=	837.0	ug.mL-1	PMID[546633]
NPT168	Cell Line	P388	Mus musculus	IC50	=	185.0	ug.mL-1	PMID[546633]
NPT168	Cell Line	P388	Mus musculus	IC50	=	74.0	ug.mL-1	PMID[546633]

☑ 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 NPC305808 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	432
0.1-0.2	3721
0.2-0.3	9915
0.3-0.4	13570
0.4-0.5	5961
0.5-0.6	4371
0.6-0.7	3595
0.7-0.8	1020
0.8-0.85	95
0.85-0.9	14
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9551	High Similarity	NPC161035
0.9451	High Similarity	NPC476728
0.8696	High Similarity	NPC77756
0.866	High Similarity	NPC178853
0.8636	High Similarity	NPC296734
0.8636	High Similarity	NPC24556
0.8627	High Similarity	NPC473062
0.85	High Similarity	NPC215408
0.8462	Intermediate Similarity	NPC476726
0.8462	Intermediate Similarity	NPC476727
0.8409	Intermediate Similarity	NPC257296
0.8409	Intermediate Similarity	NPC248944
0.8409	Intermediate Similarity	NPC7479
0.8404	Intermediate Similarity	NPC52756
0.84	Intermediate Similarity	NPC88469
0.8384	Intermediate Similarity	NPC213528
0.8384	Intermediate Similarity	NPC244969
0.8367	Intermediate Similarity	NPC41843
0.8352	Intermediate Similarity	NPC273290
0.8352	Intermediate Similarity	NPC232044
0.8351	Intermediate Similarity	NPC471241
0.8351	Intermediate Similarity	NPC472273
0.8333	Intermediate Similarity	NPC202898
0.8333	Intermediate Similarity	NPC327451
0.8333	Intermediate Similarity	NPC475319
0.8333	Intermediate Similarity	NPC92890
0.8316	Intermediate Similarity	NPC476189
0.83	Intermediate Similarity	NPC107385
0.8286	Intermediate Similarity	NPC97002
0.8283	Intermediate Similarity	NPC477172
0.8261	Intermediate Similarity	NPC80700
0.8252	Intermediate Similarity	NPC227879
0.8252	Intermediate Similarity	NPC220836
0.8252	Intermediate Similarity	NPC273002
0.8252	Intermediate Similarity	NPC92297
0.8252	Intermediate Similarity	NPC208333
0.8252	Intermediate Similarity	NPC233433
0.8252	Intermediate Similarity	NPC94086
0.8252	Intermediate Similarity	NPC473817
0.8247	Intermediate Similarity	NPC193785
0.8242	Intermediate Similarity	NPC227260
0.8229	Intermediate Similarity	NPC470424
0.8222	Intermediate Similarity	NPC470611
0.8218	Intermediate Similarity	NPC100078
0.8218	Intermediate Similarity	NPC327093
0.8218	Intermediate Similarity	NPC470167
0.8211	Intermediate Similarity	NPC475878
0.82	Intermediate Similarity	NPC470172
0.8191	Intermediate Similarity	NPC61688
0.8191	Intermediate Similarity	NPC200580
0.8182	Intermediate Similarity	NPC20028
0.8155	Intermediate Similarity	NPC472079
0.8144	Intermediate Similarity	NPC287354
0.8144	Intermediate Similarity	NPC62407
0.8137	Intermediate Similarity	NPC306776
0.8137	Intermediate Similarity	NPC166079
0.8131	Intermediate Similarity	NPC475490
0.8125	Intermediate Similarity	NPC472231
0.8125	Intermediate Similarity	NPC472232
0.8119	Intermediate Similarity	NPC34562
0.8119	Intermediate Similarity	NPC473406
0.8111	Intermediate Similarity	NPC469745
0.8085	Intermediate Similarity	NPC236459
0.8065	Intermediate Similarity	NPC472272
0.8065	Intermediate Similarity	NPC248216
0.8058	Intermediate Similarity	NPC203974
0.8056	Intermediate Similarity	NPC179429
0.8043	Intermediate Similarity	NPC471044
0.8043	Intermediate Similarity	NPC474996
0.8043	Intermediate Similarity	NPC473336
0.8022	Intermediate Similarity	NPC289486
0.8022	Intermediate Similarity	NPC61107
0.802	Intermediate Similarity	NPC310031
0.802	Intermediate Similarity	NPC80191
0.8	Intermediate Similarity	NPC67653
0.8	Intermediate Similarity	NPC163314
0.8	Intermediate Similarity	NPC471459
0.7979	Intermediate Similarity	NPC470920
0.7959	Intermediate Similarity	NPC215570
0.7941	Intermediate Similarity	NPC471253
0.7917	Intermediate Similarity	NPC473542
0.7917	Intermediate Similarity	NPC476296
0.7905	Intermediate Similarity	NPC228190
0.7905	Intermediate Similarity	NPC236753
0.7895	Intermediate Similarity	NPC90676
0.7889	Intermediate Similarity	NPC80891
0.7889	Intermediate Similarity	NPC320144
0.7889	Intermediate Similarity	NPC201276
0.7879	Intermediate Similarity	NPC475765
0.7879	Intermediate Similarity	NPC116683
0.7879	Intermediate Similarity	NPC156377
0.7879	Intermediate Similarity	NPC475785
0.787	Intermediate Similarity	NPC79193
0.7865	Intermediate Similarity	NPC221420
0.7864	Intermediate Similarity	NPC29705
0.785	Intermediate Similarity	NPC477492
0.785	Intermediate Similarity	NPC477489
0.7849	Intermediate Similarity	NPC237938
0.7849	Intermediate Similarity	NPC50438
0.7849	Intermediate Similarity	NPC473299
0.7849	Intermediate Similarity	NPC219535
0.7841	Intermediate Similarity	NPC159789
0.7835	Intermediate Similarity	NPC149966
0.7835	Intermediate Similarity	NPC474065
0.7835	Intermediate Similarity	NPC5632
0.7835	Intermediate Similarity	NPC59006
0.7826	Intermediate Similarity	NPC268040
0.7812	Intermediate Similarity	NPC477440
0.7812	Intermediate Similarity	NPC228059
0.7812	Intermediate Similarity	NPC477443
0.781	Intermediate Similarity	NPC316930
0.781	Intermediate Similarity	NPC94529
0.7802	Intermediate Similarity	NPC470609
0.78	Intermediate Similarity	NPC472145
0.7789	Intermediate Similarity	NPC210658
0.7789	Intermediate Similarity	NPC161928
0.7788	Intermediate Similarity	NPC4115
0.7778	Intermediate Similarity	NPC324700
0.7778	Intermediate Similarity	NPC185465
0.7778	Intermediate Similarity	NPC80089
0.7778	Intermediate Similarity	NPC224802
0.7778	Intermediate Similarity	NPC470031
0.7778	Intermediate Similarity	NPC171426
0.7778	Intermediate Similarity	NPC34046
0.7767	Intermediate Similarity	NPC266
0.7767	Intermediate Similarity	NPC469985
0.7757	Intermediate Similarity	NPC469824
0.7757	Intermediate Similarity	NPC470311
0.7755	Intermediate Similarity	NPC311246
0.7755	Intermediate Similarity	NPC88962
0.7755	Intermediate Similarity	NPC149400
0.7755	Intermediate Similarity	NPC182740
0.7755	Intermediate Similarity	NPC256104
0.7755	Intermediate Similarity	NPC472238
0.7755	Intermediate Similarity	NPC122083
0.7755	Intermediate Similarity	NPC167644
0.7755	Intermediate Similarity	NPC144790
0.7755	Intermediate Similarity	NPC211845
0.7755	Intermediate Similarity	NPC472237
0.7753	Intermediate Similarity	NPC472486
0.7753	Intermediate Similarity	NPC472487
0.7753	Intermediate Similarity	NPC475742
0.7753	Intermediate Similarity	NPC5767
0.7736	Intermediate Similarity	NPC471250
0.7736	Intermediate Similarity	NPC321661
0.7736	Intermediate Similarity	NPC320475
0.7732	Intermediate Similarity	NPC477442
0.7732	Intermediate Similarity	NPC477433
0.7732	Intermediate Similarity	NPC50443
0.7732	Intermediate Similarity	NPC18536
0.7732	Intermediate Similarity	NPC477444
0.7727	Intermediate Similarity	NPC254340
0.7723	Intermediate Similarity	NPC476294
0.7723	Intermediate Similarity	NPC472144
0.7723	Intermediate Similarity	NPC253995
0.7717	Intermediate Similarity	NPC58631
0.7708	Intermediate Similarity	NPC477614
0.7708	Intermediate Similarity	NPC128475
0.7708	Intermediate Similarity	NPC226491
0.7708	Intermediate Similarity	NPC281004
0.7692	Intermediate Similarity	NPC47281
0.7692	Intermediate Similarity	NPC13149
0.7692	Intermediate Similarity	NPC476176
0.7684	Intermediate Similarity	NPC474448
0.7684	Intermediate Similarity	NPC471240
0.7684	Intermediate Similarity	NPC83242
0.7684	Intermediate Similarity	NPC120395
0.7677	Intermediate Similarity	NPC329713
0.7677	Intermediate Similarity	NPC206878
0.7677	Intermediate Similarity	NPC131693
0.7677	Intermediate Similarity	NPC45959
0.7677	Intermediate Similarity	NPC3538
0.7677	Intermediate Similarity	NPC470423
0.7677	Intermediate Similarity	NPC179859
0.7677	Intermediate Similarity	NPC174024
0.7677	Intermediate Similarity	NPC175
0.7677	Intermediate Similarity	NPC475436
0.7677	Intermediate Similarity	NPC473851
0.7677	Intermediate Similarity	NPC76136
0.7677	Intermediate Similarity	NPC30687
0.7677	Intermediate Similarity	NPC312678
0.7677	Intermediate Similarity	NPC252253
0.7677	Intermediate Similarity	NPC113500
0.7677	Intermediate Similarity	NPC217567
0.7677	Intermediate Similarity	NPC291547
0.7677	Intermediate Similarity	NPC24960
0.7677	Intermediate Similarity	NPC253268
0.7677	Intermediate Similarity	NPC477224
0.7677	Intermediate Similarity	NPC473774
0.767	Intermediate Similarity	NPC309388
0.767	Intermediate Similarity	NPC475803
0.767	Intermediate Similarity	NPC471254
0.7667	Intermediate Similarity	NPC207010
0.7667	Intermediate Similarity	NPC317913
0.766	Intermediate Similarity	NPC477434
0.766	Intermediate Similarity	NPC105895
0.7647	Intermediate Similarity	NPC108371
0.7647	Intermediate Similarity	NPC470030
0.7647	Intermediate Similarity	NPC15390
0.7642	Intermediate Similarity	NPC469826

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 NPC305808 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	465
0.1-0.2	3809
0.2-0.3	3370
0.3-0.4	899
0.4-0.5	264
0.5-0.6	169
0.6-0.7	139
0.7-0.8	33
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8586	High Similarity	NPD8170	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD6928	Phase 2
0.7841	Intermediate Similarity	NPD3703	Phase 2
0.7778	Intermediate Similarity	NPD6115	Approved
0.7778	Intermediate Similarity	NPD6114	Approved
0.7778	Intermediate Similarity	NPD6697	Approved
0.7778	Intermediate Similarity	NPD6118	Approved
0.7667	Intermediate Similarity	NPD6116	Phase 1
0.7576	Intermediate Similarity	NPD8171	Discontinued
0.7556	Intermediate Similarity	NPD6117	Approved
0.7522	Intermediate Similarity	NPD6059	Approved
0.7522	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6370	Approved
0.7386	Intermediate Similarity	NPD4789	Approved
0.7386	Intermediate Similarity	NPD4244	Approved
0.7386	Intermediate Similarity	NPD4245	Approved
0.7373	Intermediate Similarity	NPD7736	Approved
0.7333	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6016	Approved
0.7304	Intermediate Similarity	NPD6015	Approved
0.7273	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3698	Phase 2
0.7273	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD7492	Approved
0.7255	Intermediate Similarity	NPD7991	Discontinued
0.7253	Intermediate Similarity	NPD3702	Approved
0.7241	Intermediate Similarity	NPD5988	Approved
0.7207	Intermediate Similarity	NPD6882	Approved
0.7203	Intermediate Similarity	NPD6616	Approved
0.7156	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD8293	Discontinued
0.713	Intermediate Similarity	NPD7128	Approved
0.713	Intermediate Similarity	NPD6402	Approved
0.713	Intermediate Similarity	NPD6675	Approved
0.713	Intermediate Similarity	NPD5739	Approved
0.7111	Intermediate Similarity	NPD5777	Approved
0.7105	Intermediate Similarity	NPD6009	Approved
0.7083	Intermediate Similarity	NPD6033	Approved
0.7075	Intermediate Similarity	NPD1700	Approved
0.7064	Intermediate Similarity	NPD6412	Phase 2
0.7059	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD6881	Approved
0.6966	Remote Similarity	NPD5360	Phase 3
0.6966	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD8034	Phase 2
0.6961	Remote Similarity	NPD8035	Phase 2
0.6952	Remote Similarity	NPD4755	Approved
0.6937	Remote Similarity	NPD6373	Approved
0.6937	Remote Similarity	NPD6372	Approved
0.6909	Remote Similarity	NPD5697	Approved
0.6909	Remote Similarity	NPD5701	Approved
0.6885	Remote Similarity	NPD7319	Approved
0.6875	Remote Similarity	NPD7290	Approved
0.6875	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD7102	Approved
0.6869	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6011	Approved
0.6842	Remote Similarity	NPD4632	Approved
0.6842	Remote Similarity	NPD8133	Approved
0.6822	Remote Similarity	NPD4696	Approved
0.6822	Remote Similarity	NPD5285	Approved
0.6822	Remote Similarity	NPD5286	Approved
0.6822	Remote Similarity	NPD4700	Approved
0.6818	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6008	Approved
0.6814	Remote Similarity	NPD6847	Approved
0.6814	Remote Similarity	NPD6869	Approved
0.6814	Remote Similarity	NPD6649	Approved
0.6814	Remote Similarity	NPD6650	Approved
0.6814	Remote Similarity	NPD8130	Phase 1
0.6814	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6617	Approved
0.681	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6012	Approved
0.6786	Remote Similarity	NPD6013	Approved
0.6786	Remote Similarity	NPD6014	Approved
0.6759	Remote Similarity	NPD5223	Approved
0.6754	Remote Similarity	NPD8297	Approved
0.6739	Remote Similarity	NPD6081	Approved
0.6724	Remote Similarity	NPD6940	Discontinued
0.6697	Remote Similarity	NPD5225	Approved
0.6697	Remote Similarity	NPD5226	Approved
0.6697	Remote Similarity	NPD5211	Phase 2
0.6697	Remote Similarity	NPD4633	Approved
0.6697	Remote Similarity	NPD5224	Approved
0.6696	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3671	Phase 1
0.6639	Remote Similarity	NPD6319	Approved
0.6637	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5174	Approved
0.6636	Remote Similarity	NPD5175	Approved
0.6636	Remote Similarity	NPD4754	Approved
0.6612	Remote Similarity	NPD6067	Discontinued
0.6612	Remote Similarity	NPD8328	Phase 3
0.6612	Remote Similarity	NPD7604	Phase 2
0.6602	Remote Similarity	NPD5328	Approved
0.6583	Remote Similarity	NPD5983	Phase 2
0.6579	Remote Similarity	NPD4634	Approved
0.6577	Remote Similarity	NPD5141	Approved
0.6574	Remote Similarity	NPD7638	Approved
0.6559	Remote Similarity	NPD4758	Discontinued
0.6556	Remote Similarity	NPD4224	Phase 2
0.6542	Remote Similarity	NPD5222	Approved
0.6542	Remote Similarity	NPD4697	Phase 3
0.6542	Remote Similarity	NPD5221	Approved
0.6542	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4767	Approved
0.6518	Remote Similarity	NPD4768	Approved
0.6514	Remote Similarity	NPD7639	Approved
0.6514	Remote Similarity	NPD7640	Approved
0.6504	Remote Similarity	NPD6336	Discontinued
0.65	Remote Similarity	NPD4788	Approved
0.6495	Remote Similarity	NPD4238	Approved
0.6495	Remote Similarity	NPD4802	Phase 2
0.6495	Remote Similarity	NPD5364	Discontinued
0.6481	Remote Similarity	NPD5173	Approved
0.6481	Remote Similarity	NPD6084	Phase 2
0.6481	Remote Similarity	NPD6083	Phase 2
0.6476	Remote Similarity	NPD6079	Approved
0.6471	Remote Similarity	NPD6335	Approved
0.6471	Remote Similarity	NPD7328	Approved
0.6471	Remote Similarity	NPD7327	Approved
0.6452	Remote Similarity	NPD4787	Phase 1
0.6446	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6274	Approved
0.6429	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7100	Approved
0.6417	Remote Similarity	NPD7101	Approved
0.6417	Remote Similarity	NPD7516	Approved
0.6415	Remote Similarity	NPD6399	Phase 3
0.6415	Remote Similarity	NPD4202	Approved
0.6404	Remote Similarity	NPD5128	Approved
0.6404	Remote Similarity	NPD4729	Approved
0.6404	Remote Similarity	NPD4730	Approved
0.6396	Remote Similarity	NPD7632	Discontinued
0.6387	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD8294	Approved
0.6364	Remote Similarity	NPD8377	Approved
0.6364	Remote Similarity	NPD8418	Phase 2
0.6333	Remote Similarity	NPD6313	Approved
0.6333	Remote Similarity	NPD6314	Approved
0.6311	Remote Similarity	NPD8296	Approved
0.6311	Remote Similarity	NPD8380	Approved
0.6311	Remote Similarity	NPD8335	Approved
0.6311	Remote Similarity	NPD8379	Approved
0.6311	Remote Similarity	NPD8033	Approved
0.6311	Remote Similarity	NPD6909	Approved
0.6311	Remote Similarity	NPD8378	Approved
0.6311	Remote Similarity	NPD6908	Approved
0.63	Remote Similarity	NPD1780	Approved
0.63	Remote Similarity	NPD1779	Approved
0.6293	Remote Similarity	NPD5248	Approved
0.6293	Remote Similarity	NPD5247	Approved
0.6293	Remote Similarity	NPD5249	Phase 3
0.6293	Remote Similarity	NPD5250	Approved
0.6293	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5251	Approved
0.6293	Remote Similarity	NPD5169	Approved
0.6293	Remote Similarity	NPD5135	Approved
0.6286	Remote Similarity	NPD4753	Phase 2
0.6275	Remote Similarity	NPD4786	Approved
0.6239	Remote Similarity	NPD5127	Approved
0.6239	Remote Similarity	NPD5216	Approved
0.6239	Remote Similarity	NPD5215	Approved
0.6239	Remote Similarity	NPD5217	Approved
0.6228	Remote Similarity	NPD6920	Discontinued
0.6204	Remote Similarity	NPD7748	Approved
0.619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7902	Approved
0.6176	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3669	Approved
0.6172	Remote Similarity	NPD5956	Approved
0.6168	Remote Similarity	NPD7515	Phase 2
0.6167	Remote Similarity	NPD6868	Approved
0.6154	Remote Similarity	NPD3618	Phase 1
0.6147	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5695	Phase 3
0.6126	Remote Similarity	NPD5696	Approved
0.6117	Remote Similarity	NPD3133	Approved
0.6117	Remote Similarity	NPD3666	Approved
0.6117	Remote Similarity	NPD3665	Phase 1
0.6083	Remote Similarity	NPD5167	Approved
0.6082	Remote Similarity	NPD1811	Approved
0.6082	Remote Similarity	NPD1810	Approved
0.6078	Remote Similarity	NPD3667	Approved
0.6058	Remote Similarity	NPD5329	Approved
0.6048	Remote Similarity	NPD6921	Approved
0.604	Remote Similarity	NPD7525	Registered
0.6038	Remote Similarity	NPD5737	Approved
0.6038	Remote Similarity	NPD6903	Approved
0.6038	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD4629	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