NPASS Compound

Structure

NPC469470 OpenBabel07101719242D 25 30 0 0 1 0 0 0 0 0999 V2000 0.7682 -0.9530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4248 1.0136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0172 -2.0433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6050 -1.2343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0227 -1.9388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1982 -0.3207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7989 -1.2162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0623 1.0110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6637 0.0415 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6159 -1.0252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6649 -0.7162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4254 0.5768 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2037 -0.2162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9328 -0.7162 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7989 0.7838 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3501 0.2225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3678 -0.1919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6649 0.2838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 -0.2021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1108 0.2123 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6159 0.5928 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9328 0.2838 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.3341 -1.0887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4257 1.0562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 10 2 0 0 0 0 6 13 2 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 9 22 1 1 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 18 2 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 6 0 0 0 15 18 1 0 0 0 0 15 22 1 6 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.18
Volume:	340.956
LogP:	2.54
LogD:	2.626
LogS:	-3.058
# Rotatable Bonds:	1
TPSA:	57.72
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.837
Synthetic Accessibility Score:	5.933
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.586
MDCK Permeability:	8.434618393948767e-06
Pgp-inhibitor:	0.023
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.581
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.111

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.812
Plasma Protein Binding (PPB):	74.53653717041016%
Volume Distribution (VD):	2.813
Pgp-substrate:	21.267375946044922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.095
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.137
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.217
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.787
CYP3A4-inhibitor:	0.303
CYP3A4-substrate:	0.705

ADMET: Excretion

Clearance (CL):	6.626
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.625
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.468
Rat Oral Acute Toxicity:	0.727
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.09
Carcinogencity:	0.814
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC469470

Natural Product ID:	NPC469470
*Common Name:**	Alstoyunine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MCELWEQVMZEFMT-XQZKUMGPSA-N
Standard InCHI:	InChI=1S/C20H24N2O3/c1-9-16-12-8-15-18-11(10-5-3-4-6-13(10)21-18)7-14(22(9)15)17(12)19(23)25-20(16)24-2/h3-6,9,12,14-17,19-21,23H,7-8H2,1-2H3/t9-,12?,14-,15-,16+,17+,19+,20+/m0/s1
SMILES:	CC1C2C3CC4N1C(C3C(OC2OC)O)CC5=C4NC6=CC=CC=C56
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079511
PubChem CID:	46882285
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003759] Macroline 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
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19775092]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	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	2
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	27.76	%	PMID[548924]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	32.14	%	PMID[548924]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	38.36	%	PMID[548924]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[548924]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	40000.0	nM	PMID[548924]

☑ 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 NPC469470 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	358
0.1-0.2	1793
0.2-0.3	10459
0.3-0.4	21156
0.4-0.5	4656
0.5-0.6	2452
0.6-0.7	1423
0.7-0.8	359
0.8-0.85	24
0.85-0.9	12
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469501
0.9298	High Similarity	NPC139291
0.9298	High Similarity	NPC472108
0.9226	High Similarity	NPC472123
0.8966	High Similarity	NPC472109
0.8966	High Similarity	NPC472110
0.896	High Similarity	NPC187827
0.896	High Similarity	NPC472105
0.8786	High Similarity	NPC472122
0.8786	High Similarity	NPC24594
0.8713	High Similarity	NPC317430
0.8541	High Similarity	NPC52557
0.8539	High Similarity	NPC472104
0.8407	Intermediate Similarity	NPC175474
0.8315	Intermediate Similarity	NPC326575
0.8305	Intermediate Similarity	NPC189812
0.8305	Intermediate Similarity	NPC329688
0.8268	Intermediate Similarity	NPC133261
0.8254	Intermediate Similarity	NPC249040
0.8232	Intermediate Similarity	NPC174788
0.8216	Intermediate Similarity	NPC472097
0.8208	Intermediate Similarity	NPC255229
0.8208	Intermediate Similarity	NPC81229
0.8191	Intermediate Similarity	NPC52254
0.8172	Intermediate Similarity	NPC472113
0.8162	Intermediate Similarity	NPC472112
0.8158	Intermediate Similarity	NPC79129
0.8158	Intermediate Similarity	NPC195461
0.8158	Intermediate Similarity	NPC313985
0.8158	Intermediate Similarity	NPC81654
0.8158	Intermediate Similarity	NPC49196
0.8158	Intermediate Similarity	NPC249150
0.8132	Intermediate Similarity	NPC19679
0.8053	Intermediate Similarity	NPC50503
0.8035	Intermediate Similarity	NPC285469
0.8022	Intermediate Similarity	NPC15840
0.8011	Intermediate Similarity	NPC111602
0.8011	Intermediate Similarity	NPC196251
0.8011	Intermediate Similarity	NPC63199
0.8011	Intermediate Similarity	NPC102338
0.7989	Intermediate Similarity	NPC472294
0.797	Intermediate Similarity	NPC475422
0.7969	Intermediate Similarity	NPC254240
0.7969	Intermediate Similarity	NPC199851
0.7969	Intermediate Similarity	NPC312870
0.7969	Intermediate Similarity	NPC294909
0.7969	Intermediate Similarity	NPC128265
0.796	Intermediate Similarity	NPC82070
0.7959	Intermediate Similarity	NPC87755
0.795	Intermediate Similarity	NPC476114
0.7947	Intermediate Similarity	NPC245916
0.7919	Intermediate Similarity	NPC477548
0.7872	Intermediate Similarity	NPC95783
0.7861	Intermediate Similarity	NPC472323
0.7854	Intermediate Similarity	NPC475271
0.7853	Intermediate Similarity	NPC16667
0.7849	Intermediate Similarity	NPC79062
0.7849	Intermediate Similarity	NPC472107
0.7841	Intermediate Similarity	NPC221786
0.7841	Intermediate Similarity	NPC474880
0.7821	Intermediate Similarity	NPC49954
0.7821	Intermediate Similarity	NPC474561
0.7798	Intermediate Similarity	NPC88097
0.7797	Intermediate Similarity	NPC229173
0.7796	Intermediate Similarity	NPC472119
0.7772	Intermediate Similarity	NPC219336
0.7771	Intermediate Similarity	NPC207726
0.7766	Intermediate Similarity	NPC475841
0.7766	Intermediate Similarity	NPC474145
0.7765	Intermediate Similarity	NPC470508
0.7742	Intermediate Similarity	NPC143533
0.774	Intermediate Similarity	NPC476492
0.773	Intermediate Similarity	NPC469896
0.7722	Intermediate Similarity	NPC160105
0.7722	Intermediate Similarity	NPC54988
0.7717	Intermediate Similarity	NPC15573
0.7717	Intermediate Similarity	NPC183662
0.7717	Intermediate Similarity	NPC217372
0.7713	Intermediate Similarity	NPC66210
0.7701	Intermediate Similarity	NPC258480
0.77	Intermediate Similarity	NPC126066
0.7688	Intermediate Similarity	NPC233936
0.7684	Intermediate Similarity	NPC469762
0.768	Intermediate Similarity	NPC63751
0.7677	Intermediate Similarity	NPC472111
0.7654	Intermediate Similarity	NPC282231
0.765	Intermediate Similarity	NPC314603
0.764	Intermediate Similarity	NPC475990
0.764	Intermediate Similarity	NPC67056
0.7637	Intermediate Similarity	NPC474897
0.7637	Intermediate Similarity	NPC280548
0.7627	Intermediate Similarity	NPC469785
0.7619	Intermediate Similarity	NPC478077
0.7617	Intermediate Similarity	NPC19692
0.7617	Intermediate Similarity	NPC220151
0.7611	Intermediate Similarity	NPC311276
0.7611	Intermediate Similarity	NPC271797
0.7611	Intermediate Similarity	NPC21174
0.76	Intermediate Similarity	NPC475910
0.7598	Intermediate Similarity	NPC279918
0.7594	Intermediate Similarity	NPC71037
0.7592	Intermediate Similarity	NPC314333
0.7592	Intermediate Similarity	NPC329858
0.7586	Intermediate Similarity	NPC21605
0.7582	Intermediate Similarity	NPC201700
0.7576	Intermediate Similarity	NPC476115
0.7571	Intermediate Similarity	NPC470507
0.756	Intermediate Similarity	NPC198988
0.7554	Intermediate Similarity	NPC34508
0.7552	Intermediate Similarity	NPC243716
0.755	Intermediate Similarity	NPC474905
0.7542	Intermediate Similarity	NPC230869
0.7539	Intermediate Similarity	NPC46413
0.7526	Intermediate Similarity	NPC57994
0.7526	Intermediate Similarity	NPC289299
0.7515	Intermediate Similarity	NPC325252
0.7514	Intermediate Similarity	NPC469786
0.7514	Intermediate Similarity	NPC469763
0.7514	Intermediate Similarity	NPC472586
0.7514	Intermediate Similarity	NPC259644
0.7514	Intermediate Similarity	NPC194640
0.7514	Intermediate Similarity	NPC469765
0.7514	Intermediate Similarity	NPC469760
0.7514	Intermediate Similarity	NPC25008
0.7514	Intermediate Similarity	NPC73952
0.7513	Intermediate Similarity	NPC55493
0.75	Intermediate Similarity	NPC471080
0.75	Intermediate Similarity	NPC113626
0.75	Intermediate Similarity	NPC473868
0.75	Intermediate Similarity	NPC63157
0.75	Intermediate Similarity	NPC469592
0.75	Intermediate Similarity	NPC314394
0.7488	Intermediate Similarity	NPC470126
0.7487	Intermediate Similarity	NPC472443
0.7486	Intermediate Similarity	NPC154293
0.7473	Intermediate Similarity	NPC121903
0.7472	Intermediate Similarity	NPC211572
0.7472	Intermediate Similarity	NPC75540
0.7472	Intermediate Similarity	NPC212376
0.7472	Intermediate Similarity	NPC80597
0.7472	Intermediate Similarity	NPC70922
0.7471	Intermediate Similarity	NPC470440
0.7462	Intermediate Similarity	NPC241024
0.746	Intermediate Similarity	NPC163055
0.746	Intermediate Similarity	NPC472444
0.7453	Intermediate Similarity	NPC253580
0.7453	Intermediate Similarity	NPC33949
0.7443	Intermediate Similarity	NPC37548
0.7442	Intermediate Similarity	NPC59084
0.744	Intermediate Similarity	NPC469594
0.7437	Intermediate Similarity	NPC162730
0.7435	Intermediate Similarity	NPC235684
0.7435	Intermediate Similarity	NPC474707
0.7433	Intermediate Similarity	NPC59269
0.7433	Intermediate Similarity	NPC68354
0.7433	Intermediate Similarity	NPC151939
0.7427	Intermediate Similarity	NPC183407
0.7419	Intermediate Similarity	NPC37423
0.7419	Intermediate Similarity	NPC275305
0.7418	Intermediate Similarity	NPC40779
0.7418	Intermediate Similarity	NPC469541
0.7416	Intermediate Similarity	NPC471506
0.7415	Intermediate Similarity	NPC234078
0.7415	Intermediate Similarity	NPC221100
0.7411	Intermediate Similarity	NPC473640
0.7405	Intermediate Similarity	NPC158129
0.7398	Intermediate Similarity	NPC231342
0.7396	Intermediate Similarity	NPC204565
0.7396	Intermediate Similarity	NPC317030
0.7394	Intermediate Similarity	NPC270009
0.7389	Intermediate Similarity	NPC476116
0.7385	Intermediate Similarity	NPC81802
0.7385	Intermediate Similarity	NPC472210
0.7385	Intermediate Similarity	NPC247735
0.7385	Intermediate Similarity	NPC472295
0.7385	Intermediate Similarity	NPC269886
0.7381	Intermediate Similarity	NPC280272
0.738	Intermediate Similarity	NPC150048
0.738	Intermediate Similarity	NPC203754
0.738	Intermediate Similarity	NPC280852
0.7379	Intermediate Similarity	NPC313640
0.7376	Intermediate Similarity	NPC477065
0.7374	Intermediate Similarity	NPC100321
0.7368	Intermediate Similarity	NPC48938
0.7366	Intermediate Similarity	NPC161861
0.7358	Intermediate Similarity	NPC213629
0.7358	Intermediate Similarity	NPC173028
0.7358	Intermediate Similarity	NPC65215
0.7356	Intermediate Similarity	NPC281049
0.7354	Intermediate Similarity	NPC91179
0.7354	Intermediate Similarity	NPC300688
0.735	Intermediate Similarity	NPC474116
0.735	Intermediate Similarity	NPC476874
0.7341	Intermediate Similarity	NPC2949
0.734	Intermediate Similarity	NPC248454
0.734	Intermediate Similarity	NPC211997
0.734	Intermediate Similarity	NPC234987
0.7333	Intermediate Similarity	NPC141353
0.733	Intermediate Similarity	NPC475602
0.733	Intermediate Similarity	NPC165201

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 NPC469470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	514
0.2-0.3	810
0.3-0.4	1788
0.4-0.5	2949
0.5-0.6	2233
0.6-0.7	595
0.7-0.8	57
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8158	Intermediate Similarity	NPD4601	Approved
0.8158	Intermediate Similarity	NPD4600	Approved
0.7969	Intermediate Similarity	NPD4500	Approved
0.7969	Intermediate Similarity	NPD4501	Approved
0.7765	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2144	Approved
0.7594	Intermediate Similarity	NPD3038	Discontinued
0.7592	Intermediate Similarity	NPD4499	Approved
0.7541	Intermediate Similarity	NPD1325	Approved
0.7541	Intermediate Similarity	NPD1326	Approved
0.754	Intermediate Similarity	NPD6595	Phase 3
0.7526	Intermediate Similarity	NPD4602	Approved
0.75	Intermediate Similarity	NPD7957	Phase 1
0.75	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4079	Approved
0.7487	Intermediate Similarity	NPD4076	Approved
0.7474	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD3506	Approved
0.7433	Intermediate Similarity	NPD3505	Approved
0.7426	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5065	Approved
0.7393	Intermediate Similarity	NPD7271	Approved
0.7368	Intermediate Similarity	NPD5596	Phase 2
0.7368	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7731	Approved
0.7324	Intermediate Similarity	NPD7730	Approved
0.7322	Intermediate Similarity	NPD5138	Approved
0.7322	Intermediate Similarity	NPD5140	Approved
0.7313	Intermediate Similarity	NPD8072	Approved
0.7306	Intermediate Similarity	NPD8431	Approved
0.7303	Intermediate Similarity	NPD4463	Approved
0.7303	Intermediate Similarity	NPD4462	Approved
0.7302	Intermediate Similarity	NPD8386	Phase 2
0.7292	Intermediate Similarity	NPD6227	Discontinued
0.7287	Intermediate Similarity	NPD2381	Approved
0.7287	Intermediate Similarity	NPD2380	Approved
0.7287	Intermediate Similarity	NPD2382	Approved
0.7282	Intermediate Similarity	NPD5913	Phase 3
0.7282	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2092	Phase 2
0.7277	Intermediate Similarity	NPD2095	Phase 2
0.7277	Intermediate Similarity	NPD2094	Phase 2
0.7263	Intermediate Similarity	NPD2882	Phase 1
0.7256	Intermediate Similarity	NPD7824	Approved
0.724	Intermediate Similarity	NPD2096	Phase 2
0.724	Intermediate Similarity	NPD2091	Phase 2
0.7235	Intermediate Similarity	NPD7791	Approved
0.7235	Intermediate Similarity	NPD7790	Approved
0.7235	Intermediate Similarity	NPD7952	Approved
0.7235	Intermediate Similarity	NPD7951	Approved
0.7235	Intermediate Similarity	NPD7953	Approved
0.7235	Intermediate Similarity	NPD7950	Approved
0.7235	Intermediate Similarity	NPD7789	Approved
0.7234	Intermediate Similarity	NPD482	Approved
0.7216	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5104	Approved
0.7192	Intermediate Similarity	NPD8272	Phase 2
0.7186	Intermediate Similarity	NPD5003	Discontinued
0.7178	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6158	Phase 2
0.7158	Intermediate Similarity	NPD4181	Approved
0.7158	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6492	Phase 2
0.7143	Intermediate Similarity	NPD6281	Approved
0.7135	Intermediate Similarity	NPD1683	Approved
0.7128	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2837	Discontinued
0.7114	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6248	Phase 2
0.7114	Intermediate Similarity	NPD6249	Phase 2
0.7112	Intermediate Similarity	NPD4639	Approved
0.7112	Intermediate Similarity	NPD5021	Discontinued
0.7112	Intermediate Similarity	NPD4640	Approved
0.7112	Intermediate Similarity	NPD5862	Discovery
0.7112	Intermediate Similarity	NPD4638	Approved
0.7112	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8114	Approved
0.7108	Intermediate Similarity	NPD8115	Approved
0.7102	Intermediate Similarity	NPD1722	Approved
0.7097	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3393	Approved
0.7095	Intermediate Similarity	NPD3389	Approved
0.7095	Intermediate Similarity	NPD3394	Approved
0.7094	Intermediate Similarity	NPD8073	Approved
0.709	Intermediate Similarity	NPD750	Phase 2
0.7081	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4520	Approved
0.7047	Intermediate Similarity	NPD4203	Approved
0.7047	Intermediate Similarity	NPD4204	Approved
0.7043	Intermediate Similarity	NPD3323	Discontinued
0.7041	Intermediate Similarity	NPD2383	Phase 1
0.7039	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5254	Discontinued
0.7021	Intermediate Similarity	NPD2844	Phase 3
0.7006	Intermediate Similarity	NPD1592	Phase 3
0.7005	Intermediate Similarity	NPD2915	Discontinued
0.7005	Intermediate Similarity	NPD5658	Approved
0.7	Intermediate Similarity	NPD4703	Approved
0.7	Intermediate Similarity	NPD4702	Approved
0.6995	Remote Similarity	NPD7194	Discontinued
0.6995	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3385	Approved
0.699	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3003	Approved
0.6989	Remote Similarity	NPD786	Approved
0.6986	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6178	Phase 3
0.697	Remote Similarity	NPD8063	Discontinued
0.6963	Remote Similarity	NPD4128	Approved
0.6959	Remote Similarity	NPD7867	Phase 1
0.6959	Remote Similarity	NPD8408	Discontinued
0.6957	Remote Similarity	NPD8322	Phase 2
0.6957	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD4885	Approved
0.6954	Remote Similarity	NPD3961	Discontinued
0.6952	Remote Similarity	NPD3330	Phase 1
0.6948	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7716	Approved
0.6944	Remote Similarity	NPD7717	Approved
0.6942	Remote Similarity	NPD4036	Approved
0.6942	Remote Similarity	NPD4038	Approved
0.6942	Remote Similarity	NPD4035	Approved
0.6942	Remote Similarity	NPD4037	Approved
0.6942	Remote Similarity	NPD5426	Phase 3
0.6942	Remote Similarity	NPD4033	Approved
0.6942	Remote Similarity	NPD4039	Approved
0.6942	Remote Similarity	NPD32	Approved
0.6942	Remote Similarity	NPD31	Approved
0.6942	Remote Similarity	NPD4034	Approved
0.6942	Remote Similarity	NPD4122	Approved
0.694	Remote Similarity	NPD4120	Approved
0.694	Remote Similarity	NPD4121	Phase 3
0.6939	Remote Similarity	NPD5075	Discontinued
0.6919	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4326	Phase 2
0.6919	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4334	Discontinued
0.6919	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7944	Discontinued
0.6908	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7470	Discontinued
0.6902	Remote Similarity	NPD5742	Approved
0.6902	Remote Similarity	NPD5743	Approved
0.6902	Remote Similarity	NPD5741	Approved
0.6901	Remote Similarity	NPD8325	Phase 3
0.6901	Remote Similarity	NPD8326	Phase 3
0.6901	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7722	Suspended
0.6898	Remote Similarity	NPD2480	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7781	Approved
0.6895	Remote Similarity	NPD7780	Approved
0.6888	Remote Similarity	NPD4957	Phase 2
0.6884	Remote Similarity	NPD2564	Approved
0.6884	Remote Similarity	NPD2565	Phase 2
0.6881	Remote Similarity	NPD7935	Phase 2
0.6881	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7727	Phase 2
0.6878	Remote Similarity	NPD6307	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD8021	Approved
0.6869	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD8020	Approved
0.6868	Remote Similarity	NPD3100	Discontinued
0.6866	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1768	Approved
0.6857	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5555	Phase 1
0.685	Remote Similarity	NPD6272	Phase 1
0.685	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7948	Phase 1
0.6842	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2641	Approved
0.6842	Remote Similarity	NPD2640	Approved
0.6837	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD7234	Approved
0.6834	Remote Similarity	NPD7233	Approved
0.6832	Remote Similarity	NPD3324	Clinical (unspecified phase)

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