NPASS Compound

Structure

NPC231536 OpenBabel07101719512D 34 39 0 0 0 0 0 0 0 0999 V2000 1.9400 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7564 -1.3489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7619 -1.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 -0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9374 0.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3442 -0.5399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5768 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3551 -0.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 -0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9429 0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3387 -0.6445 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 -1.6180 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3551 1.2872 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 2.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 4 2 0 0 0 0 2 16 1 0 0 0 0 3 5 2 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 10 1 0 0 0 0 6 20 2 0 0 0 0 7 11 1 0 0 0 0 7 21 2 0 0 0 0 8 12 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 30 2 0 0 0 0 11 31 2 0 0 0 0 12 34 1 0 0 0 0 13 34 1 0 0 0 0 14 16 2 0 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 26 2 0 0 0 0 22 30 1 0 0 0 0 23 27 2 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	575.03
Volume:	486.123
LogP:	6.186
LogD:	4.267
LogS:	-5.795
# Rotatable Bonds:	6
TPSA:	60.6
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	3.007
Fsp3:	0.185
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.738
MDCK Permeability:	9.066415259439964e-06
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.345
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.816
Plasma Protein Binding (PPB):	96.59721374511719%
Volume Distribution (VD):	4.001
Pgp-substrate:	3.3065881729125977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.887
CYP2C19-inhibitor:	0.618
CYP2C19-substrate:	0.64
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.334
CYP2D6-inhibitor:	0.969
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.369
CYP3A4-substrate:	0.793

ADMET: Excretion

Clearance (CL):	2.395
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.97
Human Hepatotoxicity (H-HT):	0.825
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.872
Carcinogencity:	0.137
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.994

Download Data

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

Natural Product: NPC231536

Natural Product ID:	NPC231536
*Common Name:**	Plakortamine C
IUPAC Name:	2-(7-bromo-9H-pyrido[3,4-b]indol-1-yl)-N-[2-(7-bromo-9H-pyrido[3,4-b]indol-1-yl)ethyl]-N-methylethanamine
Synonyms:	Plakortamine C
Standard InCHIKey:	XOTOOXJTBNMZDQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H23Br2N5/c1-34(12-8-22-26-20(6-10-30-22)18-4-2-16(28)14-24(18)32-26)13-9-23-27-21(7-11-31-23)19-5-3-17(29)15-25(19)33-27/h2-7,10-11,14-15,32-33H,8-9,12-13H2,1H3
SMILES:	CN(CCc1c2c(ccn1)c1ccc(cc1[nH]2)Br)CCc1c2c(ccn1)c1ccc(cc1[nH]2)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449671
PubChem CID:	10393386
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[12350142]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[15387674]
NPO2117	Plakortis nigra	Species	Plakinidae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	2150.0	nM	PMID[520653]

☑ 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 NPC231536 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	1209
0.1-0.2	14765
0.2-0.3	18439
0.3-0.4	3770
0.4-0.5	1813
0.5-0.6	1561
0.6-0.7	871
0.7-0.8	238
0.8-0.85	22
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC82331
0.9006	High Similarity	NPC474958
0.9	High Similarity	NPC477611
0.8929	High Similarity	NPC274229
0.8786	High Similarity	NPC280852
0.8693	High Similarity	NPC307191
0.8538	High Similarity	NPC317105
0.8448	Intermediate Similarity	NPC97343
0.8343	Intermediate Similarity	NPC325903
0.8343	Intermediate Similarity	NPC141926
0.8287	Intermediate Similarity	NPC108011
0.8214	Intermediate Similarity	NPC201380
0.8214	Intermediate Similarity	NPC179787
0.8211	Intermediate Similarity	NPC475935
0.8211	Intermediate Similarity	NPC52909
0.8211	Intermediate Similarity	NPC94211
0.8171	Intermediate Similarity	NPC2165
0.8166	Intermediate Similarity	NPC321911
0.8158	Intermediate Similarity	NPC269203
0.8158	Intermediate Similarity	NPC13456
0.8158	Intermediate Similarity	NPC23420
0.8158	Intermediate Similarity	NPC166209
0.8158	Intermediate Similarity	NPC77241
0.8158	Intermediate Similarity	NPC303820
0.8158	Intermediate Similarity	NPC205254
0.8158	Intermediate Similarity	NPC106771
0.8155	Intermediate Similarity	NPC63545
0.8118	Intermediate Similarity	NPC53947
0.8114	Intermediate Similarity	NPC149265
0.8107	Intermediate Similarity	NPC469811
0.8105	Intermediate Similarity	NPC474318
0.8105	Intermediate Similarity	NPC268744
0.8105	Intermediate Similarity	NPC220797
0.8105	Intermediate Similarity	NPC153123
0.8105	Intermediate Similarity	NPC201266
0.8105	Intermediate Similarity	NPC475914
0.8103	Intermediate Similarity	NPC229173
0.8068	Intermediate Similarity	NPC17751
0.8047	Intermediate Similarity	NPC288838
0.7989	Intermediate Similarity	NPC216643
0.7979	Intermediate Similarity	NPC473761
0.7977	Intermediate Similarity	NPC34844
0.7965	Intermediate Similarity	NPC470233
0.7955	Intermediate Similarity	NPC470203
0.7953	Intermediate Similarity	NPC2272
0.7943	Intermediate Similarity	NPC221786
0.7943	Intermediate Similarity	NPC474880
0.7943	Intermediate Similarity	NPC475990
0.7917	Intermediate Similarity	NPC237414
0.791	Intermediate Similarity	NPC247987
0.7898	Intermediate Similarity	NPC122141
0.7898	Intermediate Similarity	NPC470204
0.7886	Intermediate Similarity	NPC236711
0.7833	Intermediate Similarity	NPC474897
0.7803	Intermediate Similarity	NPC40070
0.7802	Intermediate Similarity	NPC471579
0.7802	Intermediate Similarity	NPC280297
0.7771	Intermediate Similarity	NPC476219
0.7765	Intermediate Similarity	NPC195507
0.7751	Intermediate Similarity	NPC115611
0.7749	Intermediate Similarity	NPC474180
0.7749	Intermediate Similarity	NPC188821
0.774	Intermediate Similarity	NPC92796
0.774	Intermediate Similarity	NPC135141
0.7697	Intermediate Similarity	NPC44773
0.7697	Intermediate Similarity	NPC215584
0.7692	Intermediate Similarity	NPC88097
0.7692	Intermediate Similarity	NPC73767
0.7692	Intermediate Similarity	NPC316811
0.7692	Intermediate Similarity	NPC110126
0.7667	Intermediate Similarity	NPC280864
0.7647	Intermediate Similarity	NPC469780
0.7647	Intermediate Similarity	NPC284635
0.7647	Intermediate Similarity	NPC469784
0.7647	Intermediate Similarity	NPC469761
0.7647	Intermediate Similarity	NPC469768
0.7647	Intermediate Similarity	NPC469767
0.7647	Intermediate Similarity	NPC469779
0.7647	Intermediate Similarity	NPC469783
0.764	Intermediate Similarity	NPC56765
0.763	Intermediate Similarity	NPC316069
0.7602	Intermediate Similarity	NPC469766
0.759	Intermediate Similarity	NPC474389
0.7586	Intermediate Similarity	NPC470703
0.7586	Intermediate Similarity	NPC470111
0.7574	Intermediate Similarity	NPC105127
0.7574	Intermediate Similarity	NPC84911
0.756	Intermediate Similarity	NPC198988
0.7556	Intermediate Similarity	NPC253687
0.7538	Intermediate Similarity	NPC470505
0.7537	Intermediate Similarity	NPC473218
0.7537	Intermediate Similarity	NPC470702
0.7515	Intermediate Similarity	NPC29886
0.7515	Intermediate Similarity	NPC261195
0.7515	Intermediate Similarity	NPC96102
0.7487	Intermediate Similarity	NPC276540
0.7487	Intermediate Similarity	NPC233050
0.7486	Intermediate Similarity	NPC21605
0.7474	Intermediate Similarity	NPC99939
0.7474	Intermediate Similarity	NPC326422
0.7474	Intermediate Similarity	NPC15102
0.7474	Intermediate Similarity	NPC308931
0.7472	Intermediate Similarity	NPC476297
0.7471	Intermediate Similarity	NPC251722
0.7471	Intermediate Similarity	NPC314102
0.7459	Intermediate Similarity	NPC225018
0.7444	Intermediate Similarity	NPC318065
0.7444	Intermediate Similarity	NPC206819
0.7442	Intermediate Similarity	NPC59084
0.7433	Intermediate Similarity	NPC59269
0.7432	Intermediate Similarity	NPC478183
0.7423	Intermediate Similarity	NPC477167
0.7423	Intermediate Similarity	NPC473342
0.7423	Intermediate Similarity	NPC304187
0.7423	Intermediate Similarity	NPC477166
0.7419	Intermediate Similarity	NPC297034
0.7418	Intermediate Similarity	NPC478184
0.7418	Intermediate Similarity	NPC478182
0.7415	Intermediate Similarity	NPC477610
0.7412	Intermediate Similarity	NPC325252
0.7411	Intermediate Similarity	NPC265576
0.7407	Intermediate Similarity	NPC243381
0.7407	Intermediate Similarity	NPC275292
0.74	Intermediate Similarity	NPC317701
0.7399	Intermediate Similarity	NPC63157
0.7399	Intermediate Similarity	NPC473868
0.7389	Intermediate Similarity	NPC286427
0.7376	Intermediate Similarity	NPC166492
0.7376	Intermediate Similarity	NPC473362
0.7371	Intermediate Similarity	NPC314372
0.7356	Intermediate Similarity	NPC20144
0.7356	Intermediate Similarity	NPC190296
0.7354	Intermediate Similarity	NPC314919
0.7348	Intermediate Similarity	NPC41257
0.7341	Intermediate Similarity	NPC279081
0.7341	Intermediate Similarity	NPC2949
0.733	Intermediate Similarity	NPC143872
0.7322	Intermediate Similarity	NPC90723
0.7315	Intermediate Similarity	NPC474357
0.7308	Intermediate Similarity	NPC304926
0.7308	Intermediate Similarity	NPC476041
0.7308	Intermediate Similarity	NPC477114
0.7303	Intermediate Similarity	NPC24678
0.7303	Intermediate Similarity	NPC105818
0.7278	Intermediate Similarity	NPC82295
0.7269	Intermediate Similarity	NPC267078
0.7269	Intermediate Similarity	NPC935
0.7253	Intermediate Similarity	NPC293487
0.7253	Intermediate Similarity	NPC477591
0.7245	Intermediate Similarity	NPC314058
0.7245	Intermediate Similarity	NPC316018
0.7245	Intermediate Similarity	NPC315617
0.7245	Intermediate Similarity	NPC316359
0.7243	Intermediate Similarity	NPC56233
0.7241	Intermediate Similarity	NPC230002
0.724	Intermediate Similarity	NPC472294
0.7225	Intermediate Similarity	NPC191415
0.7222	Intermediate Similarity	NPC469763
0.7222	Intermediate Similarity	NPC469760
0.7222	Intermediate Similarity	NPC232798
0.7222	Intermediate Similarity	NPC259644
0.7222	Intermediate Similarity	NPC469765
0.7222	Intermediate Similarity	NPC73952
0.7222	Intermediate Similarity	NPC470323
0.7222	Intermediate Similarity	NPC200214
0.7222	Intermediate Similarity	NPC25008
0.7222	Intermediate Similarity	NPC469786
0.7209	Intermediate Similarity	NPC477607
0.7209	Intermediate Similarity	NPC477608
0.7207	Intermediate Similarity	NPC33421
0.72	Intermediate Similarity	NPC477004
0.7196	Intermediate Similarity	NPC121903
0.7191	Intermediate Similarity	NPC471957
0.719	Intermediate Similarity	NPC477609
0.7182	Intermediate Similarity	NPC75540
0.7182	Intermediate Similarity	NPC211572
0.7182	Intermediate Similarity	NPC80597
0.7182	Intermediate Similarity	NPC212376
0.7182	Intermediate Similarity	NPC70922
0.7181	Intermediate Similarity	NPC64055
0.7181	Intermediate Similarity	NPC161861
0.7176	Intermediate Similarity	NPC475450
0.7175	Intermediate Similarity	NPC159856
0.7175	Intermediate Similarity	NPC204141
0.7175	Intermediate Similarity	NPC470440
0.7173	Intermediate Similarity	NPC16659
0.7168	Intermediate Similarity	NPC150259
0.7166	Intermediate Similarity	NPC194411
0.7163	Intermediate Similarity	NPC473757
0.7157	Intermediate Similarity	NPC324149
0.7157	Intermediate Similarity	NPC475288
0.7151	Intermediate Similarity	NPC109447
0.715	Intermediate Similarity	NPC284678
0.715	Intermediate Similarity	NPC110158
0.7135	Intermediate Similarity	NPC21174
0.7135	Intermediate Similarity	NPC271797
0.7135	Intermediate Similarity	NPC473930
0.713	Intermediate Similarity	NPC314954
0.7129	Intermediate Similarity	NPC250835
0.7128	Intermediate Similarity	NPC201634

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 NPC231536 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	496
0.1-0.2	939
0.2-0.3	1294
0.3-0.4	2441
0.4-0.5	1956
0.5-0.6	1451
0.6-0.7	517
0.7-0.8	55
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8129	Intermediate Similarity	NPD2837	Discontinued
0.8022	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD3323	Discontinued
0.7706	Intermediate Similarity	NPD1722	Approved
0.7692	Intermediate Similarity	NPD2071	Approved
0.7692	Intermediate Similarity	NPD2068	Approved
0.7692	Intermediate Similarity	NPD2070	Approved
0.7692	Intermediate Similarity	NPD2069	Approved
0.7688	Intermediate Similarity	NPD4547	Phase 3
0.7661	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2172	Phase 1
0.7588	Intermediate Similarity	NPD786	Approved
0.7543	Intermediate Similarity	NPD3100	Discontinued
0.7515	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1895	Discontinued
0.7444	Intermediate Similarity	NPD5418	Discontinued
0.744	Intermediate Similarity	NPD1994	Approved
0.744	Intermediate Similarity	NPD1993	Approved
0.744	Intermediate Similarity	NPD1995	Approved
0.7433	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD4181	Approved
0.7396	Intermediate Similarity	NPD3385	Approved
0.7394	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6595	Phase 3
0.7341	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5065	Approved
0.7326	Intermediate Similarity	NPD4128	Approved
0.7321	Intermediate Similarity	NPD715	Phase 3
0.732	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3609	Approved
0.7312	Intermediate Similarity	NPD3610	Approved
0.731	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7394	Phase 2
0.7302	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5462	Discontinued
0.7257	Intermediate Similarity	NPD2006	Phase 2
0.7254	Intermediate Similarity	NPD2793	Discontinued
0.7247	Intermediate Similarity	NPD2430	Phase 2
0.7243	Intermediate Similarity	NPD2639	Approved
0.7243	Intermediate Similarity	NPD2642	Approved
0.7232	Intermediate Similarity	NPD1683	Approved
0.7222	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5254	Discontinued
0.7204	Intermediate Similarity	NPD2641	Approved
0.7204	Intermediate Similarity	NPD2640	Approved
0.7204	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD976	Approved
0.7182	Intermediate Similarity	NPD977	Approved
0.7182	Intermediate Similarity	NPD975	Approved
0.7176	Intermediate Similarity	NPD803	Phase 1
0.7166	Intermediate Similarity	NPD5436	Phase 1
0.7165	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7111	Discontinued
0.7143	Intermediate Similarity	NPD4886	Phase 2
0.7135	Intermediate Similarity	NPD7469	Discontinued
0.7128	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3961	Discontinued
0.7118	Intermediate Similarity	NPD3476	Approved
0.7118	Intermediate Similarity	NPD3475	Approved
0.7112	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4075	Phase 2
0.7098	Intermediate Similarity	NPD5106	Approved
0.7098	Intermediate Similarity	NPD5105	Approved
0.7093	Intermediate Similarity	NPD3944	Approved
0.7093	Intermediate Similarity	NPD3942	Approved
0.7085	Intermediate Similarity	NPD7618	Phase 3
0.7085	Intermediate Similarity	NPD7619	Phase 3
0.7083	Intermediate Similarity	NPD5962	Phase 2
0.7081	Intermediate Similarity	NPD6771	Discontinued
0.7077	Intermediate Similarity	NPD6217	Discontinued
0.7069	Intermediate Similarity	NPD45	Approved
0.7069	Intermediate Similarity	NPD6554	Approved
0.7059	Intermediate Similarity	NPD2364	Suspended
0.7047	Intermediate Similarity	NPD1708	Approved
0.7047	Intermediate Similarity	NPD1707	Approved
0.7041	Intermediate Similarity	NPD2118	Approved
0.7041	Intermediate Similarity	NPD2119	Approved
0.7037	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6828	Phase 2
0.7033	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1404	Approved
0.7027	Intermediate Similarity	NPD1403	Approved
0.7021	Intermediate Similarity	NPD2333	Discontinued
0.702	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3348	Phase 2
0.701	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7217	Approved
0.7	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7216	Approved
0.6995	Remote Similarity	NPD6816	Phase 3
0.699	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD3506	Approved
0.6979	Remote Similarity	NPD3505	Approved
0.6974	Remote Similarity	NPD7564	Discontinued
0.6968	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1183	Approved
0.6959	Remote Similarity	NPD3654	Approved
0.6957	Remote Similarity	NPD2580	Discontinued
0.6954	Remote Similarity	NPD8431	Approved
0.6954	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4079	Approved
0.6943	Remote Similarity	NPD4076	Approved
0.6941	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD991	Phase 2
0.6931	Remote Similarity	NPD2880	Discontinued
0.6927	Remote Similarity	NPD3015	Discontinued
0.6927	Remote Similarity	NPD4872	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4463	Approved
0.6923	Remote Similarity	NPD4462	Approved
0.6919	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD1313	Approved
0.6914	Remote Similarity	NPD1256	Approved
0.6914	Remote Similarity	NPD1254	Approved
0.6914	Remote Similarity	NPD1253	Approved
0.6914	Remote Similarity	NPD1255	Approved
0.6908	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4902	Discontinued
0.6902	Remote Similarity	NPD2165	Phase 1
0.6901	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4615	Phase 2
0.6898	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD5315	Discontinued
0.6897	Remote Similarity	NPD4029	Approved
0.6897	Remote Similarity	NPD4030	Approved
0.6897	Remote Similarity	NPD4028	Approved
0.6895	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6178	Phase 3
0.6881	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7445	Phase 1
0.6875	Remote Similarity	NPD1262	Discovery
0.6875	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD3114	Approved
0.6865	Remote Similarity	NPD3113	Approved
0.6865	Remote Similarity	NPD3112	Approved
0.6865	Remote Similarity	NPD3115	Approved
0.6853	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6459	Phase 2
0.6842	Remote Similarity	NPD7665	Phase 2
0.6842	Remote Similarity	NPD2443	Approved
0.6842	Remote Similarity	NPD2442	Approved
0.6842	Remote Similarity	NPD7666	Phase 3
0.6839	Remote Similarity	NPD2406	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2367	Phase 2
0.6825	Remote Similarity	NPD1333	Phase 3
0.6823	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6285	Phase 2
0.6809	Remote Similarity	NPD1015	Phase 2
0.6809	Remote Similarity	NPD1016	Phase 2
0.6806	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD2144	Approved
0.6802	Remote Similarity	NPD4957	Phase 2
0.68	Remote Similarity	NPD6133	Discontinued
0.6798	Remote Similarity	NPD2316	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4352	Phase 1
0.6789	Remote Similarity	NPD439	Approved
0.6789	Remote Similarity	NPD438	Approved
0.6788	Remote Similarity	NPD3859	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5426	Phase 3
0.6774	Remote Similarity	NPD2927	Phase 3
0.6774	Remote Similarity	NPD2150	Discontinued
0.6771	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6664	Approved
0.6751	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2008	Discontinued
0.6738	Remote Similarity	NPD4326	Phase 2
0.6738	Remote Similarity	NPD6497	Approved
0.6735	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD5642	Approved
0.6733	Remote Similarity	NPD2839	Phase 2
0.6733	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4922	Phase 2
0.6721	Remote Similarity	NPD1661	Suspended
0.6719	Remote Similarity	NPD4024	Phase 3
0.6717	Remote Similarity	NPD5892	Approved
0.6717	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2411	Approved
0.6713	Remote Similarity	NPD6470	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