NPASS Compound

Structure

NPC133261 OpenBabel07101719522D 23 27 0 0 1 0 0 0 0 0999 V2000 -0.3383 -1.9846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2660 -1.7300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5810 1.2592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5810 0.2973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8526 0.8437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7479 1.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7479 -0.1837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3913 2.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4741 0.2227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6030 1.5268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3479 2.5358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9149 1.2592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9149 0.2973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5654 0.7782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5221 0.8788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3120 -0.5149 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5320 -0.5734 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7526 0.1313 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9133 1.7576 0.0000 N 0 0 3 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 -1.7930 -1.3480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1806 -1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 12 2 0 0 0 0 7 14 2 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 6 0 0 0 17 22 1 0 0 0 0 18 21 1 0 0 0 0 18 23 1 6 0 0 0 19 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.18
Volume:	323.426
LogP:	2.606
LogD:	2.557
LogS:	-2.281
# Rotatable Bonds:	1
TPSA:	48.63
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.851
Synthetic Accessibility Score:	4.161
Fsp3:	0.579
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.16
MDCK Permeability:	1.0887141797866207e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.832
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.935
Plasma Protein Binding (PPB):	82.01937866210938%
Volume Distribution (VD):	2.832
Pgp-substrate:	14.547601699829102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.814
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.731
CYP3A4-inhibitor:	0.071
CYP3A4-substrate:	0.648

ADMET: Excretion

Clearance (CL):	11.073
Half-life (T1/2):	0.45

ADMET: Toxicity

hERG Blockers:	0.174
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.089
AMES Toxicity:	0.289
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.058
Carcinogencity:	0.082
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.704

Download Data

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

Natural Product: NPC133261

Natural Product ID:	NPC133261
*Common Name:**	MLUWIHFRNPEMDX-OKYOBFRVSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Eburnamaline
Standard InCHIKey:	MLUWIHFRNPEMDX-OKYOBFRVSA-N
Standard InCHI:	InChI=1S/C19H24N2O2/c1-2-19-9-5-10-20-11-8-13-12-6-3-4-7-14(12)21(15(13)16(19)20)18(23)17(19)22/h3-4,6-7,16-18,22-23H,2,5,8-11H2,1H3/t16-,17-,18+,19-/m0/s1
SMILES:	CC[C@]12CCCN3CCc4c5ccccc5n(c4[C@@H]13)[C@@H]([C@@H]2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088489
PubChem CID:	44613905
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002671] Eburnan-type 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
NPO32945	leuconotis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20035556]
NPO32945	leuconotis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20515042]

☑ 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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[475314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[475314]

☑ 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 NPC133261 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	286
0.1-0.2	1489
0.2-0.3	10253
0.3-0.4	21364
0.4-0.5	4021
0.5-0.6	2812
0.6-0.7	1940
0.7-0.8	480
0.8-0.85	32
0.85-0.9	14
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9152	High Similarity	NPC24594
0.9152	High Similarity	NPC472122
0.9125	High Similarity	NPC255229
0.9125	High Similarity	NPC81229
0.9102	High Similarity	NPC472105
0.9102	High Similarity	NPC187827
0.8982	High Similarity	NPC326575
0.8882	High Similarity	NPC472109
0.8882	High Similarity	NPC472110
0.8802	High Similarity	NPC472123
0.8663	High Similarity	NPC139291
0.8663	High Similarity	NPC472108
0.8655	High Similarity	NPC15840
0.8596	High Similarity	NPC57994
0.8596	High Similarity	NPC289299
0.8555	High Similarity	NPC472104
0.8412	Intermediate Similarity	NPC158129
0.8409	Intermediate Similarity	NPC478077
0.8402	Intermediate Similarity	NPC317430
0.8362	Intermediate Similarity	NPC472323
0.8352	Intermediate Similarity	NPC472107
0.8352	Intermediate Similarity	NPC79062
0.8268	Intermediate Similarity	NPC469501
0.8268	Intermediate Similarity	NPC469470
0.8266	Intermediate Similarity	NPC150048
0.8266	Intermediate Similarity	NPC203754
0.8249	Intermediate Similarity	NPC62510
0.8239	Intermediate Similarity	NPC143533
0.8225	Intermediate Similarity	NPC469541
0.8192	Intermediate Similarity	NPC258480
0.8161	Intermediate Similarity	NPC134586
0.8152	Intermediate Similarity	NPC52557
0.8136	Intermediate Similarity	NPC19679
0.8114	Intermediate Similarity	NPC211997
0.8105	Intermediate Similarity	NPC469589
0.8103	Intermediate Similarity	NPC329688
0.8103	Intermediate Similarity	NPC189812
0.8103	Intermediate Similarity	NPC472586
0.8101	Intermediate Similarity	NPC66210
0.8095	Intermediate Similarity	NPC129721
0.809	Intermediate Similarity	NPC472119
0.8086	Intermediate Similarity	NPC20144
0.8068	Intermediate Similarity	NPC472443
0.8065	Intermediate Similarity	NPC249040
0.8057	Intermediate Similarity	NPC121903
0.8042	Intermediate Similarity	NPC472111
0.8036	Intermediate Similarity	NPC285469
0.8022	Intermediate Similarity	NPC472097
0.7978	Intermediate Similarity	NPC113626
0.7933	Intermediate Similarity	NPC472444
0.7907	Intermediate Similarity	NPC469813
0.7907	Intermediate Similarity	NPC78375
0.7907	Intermediate Similarity	NPC476446
0.7889	Intermediate Similarity	NPC472294
0.7877	Intermediate Similarity	NPC314394
0.7876	Intermediate Similarity	NPC475422
0.787	Intermediate Similarity	NPC207726
0.7865	Intermediate Similarity	NPC87755
0.7861	Intermediate Similarity	NPC470508
0.7849	Intermediate Similarity	NPC16667
0.7849	Intermediate Similarity	NPC472116
0.7849	Intermediate Similarity	NPC194881
0.7814	Intermediate Similarity	NPC175474
0.7791	Intermediate Similarity	NPC104483
0.7778	Intermediate Similarity	NPC313985
0.7778	Intermediate Similarity	NPC49196
0.7778	Intermediate Similarity	NPC195461
0.7778	Intermediate Similarity	NPC79129
0.7778	Intermediate Similarity	NPC81654
0.7778	Intermediate Similarity	NPC249150
0.7772	Intermediate Similarity	NPC472112
0.7772	Intermediate Similarity	NPC95783
0.7766	Intermediate Similarity	NPC50503
0.7765	Intermediate Similarity	NPC270009
0.7755	Intermediate Similarity	NPC471080
0.7755	Intermediate Similarity	NPC469592
0.7754	Intermediate Similarity	NPC245916
0.774	Intermediate Similarity	NPC34508
0.7734	Intermediate Similarity	NPC476492
0.7733	Intermediate Similarity	NPC67056
0.7713	Intermediate Similarity	NPC469736
0.7709	Intermediate Similarity	NPC234987
0.7688	Intermediate Similarity	NPC472113
0.7672	Intermediate Similarity	NPC149708
0.7637	Intermediate Similarity	NPC159125
0.7634	Intermediate Similarity	NPC473763
0.7634	Intermediate Similarity	NPC117244
0.7627	Intermediate Similarity	NPC280548
0.7614	Intermediate Similarity	NPC49954
0.7614	Intermediate Similarity	NPC54988
0.7614	Intermediate Similarity	NPC474561
0.7611	Intermediate Similarity	NPC293472
0.76	Intermediate Similarity	NPC40779
0.76	Intermediate Similarity	NPC469594
0.7592	Intermediate Similarity	NPC470497
0.7582	Intermediate Similarity	NPC233936
0.7571	Intermediate Similarity	NPC63751
0.7571	Intermediate Similarity	NPC154293
0.7569	Intermediate Similarity	NPC219336
0.7569	Intermediate Similarity	NPC248462
0.7568	Intermediate Similarity	NPC204565
0.7558	Intermediate Similarity	NPC470507
0.7553	Intermediate Similarity	NPC474177
0.7543	Intermediate Similarity	NPC282231
0.754	Intermediate Similarity	NPC243716
0.7527	Intermediate Similarity	NPC65215
0.7527	Intermediate Similarity	NPC173028
0.7514	Intermediate Similarity	NPC217372
0.7514	Intermediate Similarity	NPC183662
0.7514	Intermediate Similarity	NPC151939
0.7514	Intermediate Similarity	NPC160105
0.7514	Intermediate Similarity	NPC15573
0.75	Intermediate Similarity	NPC194640
0.75	Intermediate Similarity	NPC311276
0.75	Intermediate Similarity	NPC469938
0.7487	Intermediate Similarity	NPC475841
0.7487	Intermediate Similarity	NPC265576
0.7487	Intermediate Similarity	NPC474145
0.7486	Intermediate Similarity	NPC279918
0.7486	Intermediate Similarity	NPC192270
0.7485	Intermediate Similarity	NPC40070
0.7473	Intermediate Similarity	NPC317030
0.7472	Intermediate Similarity	NPC201700
0.7471	Intermediate Similarity	NPC469762
0.747	Intermediate Similarity	NPC88097
0.7449	Intermediate Similarity	NPC473362
0.7449	Intermediate Similarity	NPC166492
0.7444	Intermediate Similarity	NPC314603
0.744	Intermediate Similarity	NPC253580
0.7436	Intermediate Similarity	NPC118832
0.7436	Intermediate Similarity	NPC165349
0.7436	Intermediate Similarity	NPC329708
0.7436	Intermediate Similarity	NPC264166
0.7436	Intermediate Similarity	NPC274291
0.7436	Intermediate Similarity	NPC47059
0.7435	Intermediate Similarity	NPC232130
0.7433	Intermediate Similarity	NPC111602
0.7433	Intermediate Similarity	NPC102338
0.7433	Intermediate Similarity	NPC63199
0.7433	Intermediate Similarity	NPC196251
0.7432	Intermediate Similarity	NPC300688
0.7432	Intermediate Similarity	NPC469896
0.7429	Intermediate Similarity	NPC230869
0.7427	Intermediate Similarity	NPC37548
0.7424	Intermediate Similarity	NPC126066
0.7421	Intermediate Similarity	NPC133366
0.7419	Intermediate Similarity	NPC474707
0.7414	Intermediate Similarity	NPC469785
0.7409	Intermediate Similarity	NPC312870
0.7409	Intermediate Similarity	NPC294909
0.7409	Intermediate Similarity	NPC254240
0.7409	Intermediate Similarity	NPC199851
0.7409	Intermediate Similarity	NPC128265
0.7405	Intermediate Similarity	NPC470003
0.7402	Intermediate Similarity	NPC471506
0.7396	Intermediate Similarity	NPC470499
0.7391	Intermediate Similarity	NPC470126
0.7371	Intermediate Similarity	NPC475506
0.7366	Intermediate Similarity	NPC188387
0.7366	Intermediate Similarity	NPC15102
0.7366	Intermediate Similarity	NPC163421
0.7356	Intermediate Similarity	NPC471458
0.7353	Intermediate Similarity	NPC472100
0.7351	Intermediate Similarity	NPC48938
0.7351	Intermediate Similarity	NPC163055
0.7337	Intermediate Similarity	NPC5145
0.7333	Intermediate Similarity	NPC328318
0.7333	Intermediate Similarity	NPC328596
0.7333	Intermediate Similarity	NPC155143
0.733	Intermediate Similarity	NPC221786
0.733	Intermediate Similarity	NPC84508
0.733	Intermediate Similarity	NPC474880
0.7327	Intermediate Similarity	NPC251936
0.7326	Intermediate Similarity	NPC187951
0.7323	Intermediate Similarity	NPC314957
0.7322	Intermediate Similarity	NPC64436
0.7322	Intermediate Similarity	NPC59269
0.7312	Intermediate Similarity	NPC165201
0.731	Intermediate Similarity	NPC475288
0.731	Intermediate Similarity	NPC238457
0.7306	Intermediate Similarity	NPC473640
0.7304	Intermediate Similarity	NPC52254
0.7303	Intermediate Similarity	NPC271797
0.7303	Intermediate Similarity	NPC21174
0.7299	Intermediate Similarity	NPC469786
0.7299	Intermediate Similarity	NPC73952
0.7299	Intermediate Similarity	NPC469765
0.7299	Intermediate Similarity	NPC469763
0.7299	Intermediate Similarity	NPC469760
0.7299	Intermediate Similarity	NPC259644
0.7299	Intermediate Similarity	NPC25008
0.7292	Intermediate Similarity	NPC231342
0.7288	Intermediate Similarity	NPC229173
0.7287	Intermediate Similarity	NPC119700
0.7282	Intermediate Similarity	NPC162748
0.7277	Intermediate Similarity	NPC250835
0.7273	Intermediate Similarity	NPC33949
0.7273	Intermediate Similarity	NPC53344
0.7268	Intermediate Similarity	NPC32200
0.7268	Intermediate Similarity	NPC100321

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 NPC133261 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	526
0.2-0.3	651
0.3-0.4	1521
0.4-0.5	2598
0.5-0.6	2504
0.6-0.7	1016
0.7-0.8	165
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8596	High Similarity	NPD4602	Approved
0.801	Intermediate Similarity	NPD4520	Approved
0.7955	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4600	Approved
0.7778	Intermediate Similarity	NPD8408	Discontinued
0.7778	Intermediate Similarity	NPD4601	Approved
0.776	Intermediate Similarity	NPD2383	Phase 1
0.7753	Intermediate Similarity	NPD2382	Approved
0.7753	Intermediate Similarity	NPD5104	Approved
0.7753	Intermediate Similarity	NPD2380	Approved
0.7753	Intermediate Similarity	NPD2381	Approved
0.7701	Intermediate Similarity	NPD7944	Discontinued
0.7696	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4638	Approved
0.767	Intermediate Similarity	NPD4639	Approved
0.767	Intermediate Similarity	NPD4640	Approved
0.7657	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD6227	Discontinued
0.7647	Intermediate Similarity	NPD6158	Phase 2
0.7647	Intermediate Similarity	NPD2882	Phase 1
0.7647	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4121	Phase 3
0.7602	Intermediate Similarity	NPD4120	Approved
0.7593	Intermediate Similarity	NPD3385	Approved
0.7574	Intermediate Similarity	NPD4703	Approved
0.7574	Intermediate Similarity	NPD4702	Approved
0.7572	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4326	Phase 2
0.7572	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5862	Discovery
0.7568	Intermediate Similarity	NPD8020	Approved
0.7568	Intermediate Similarity	NPD8021	Approved
0.7558	Intermediate Similarity	NPD5741	Approved
0.7558	Intermediate Similarity	NPD5743	Approved
0.7558	Intermediate Similarity	NPD5742	Approved
0.7557	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD5075	Discontinued
0.7545	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5255	Approved
0.7514	Intermediate Similarity	NPD8122	Approved
0.7514	Intermediate Similarity	NPD8123	Approved
0.7472	Intermediate Similarity	NPD5021	Discontinued
0.7458	Intermediate Similarity	NPD2915	Discontinued
0.7436	Intermediate Similarity	NPD4039	Approved
0.7436	Intermediate Similarity	NPD4122	Approved
0.7436	Intermediate Similarity	NPD4035	Approved
0.7436	Intermediate Similarity	NPD4037	Approved
0.7436	Intermediate Similarity	NPD4038	Approved
0.7436	Intermediate Similarity	NPD4036	Approved
0.7436	Intermediate Similarity	NPD4034	Approved
0.7436	Intermediate Similarity	NPD4033	Approved
0.7436	Intermediate Similarity	NPD31	Approved
0.7436	Intermediate Similarity	NPD32	Approved
0.7432	Intermediate Similarity	NPD6595	Phase 3
0.743	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD4500	Approved
0.7409	Intermediate Similarity	NPD4501	Approved
0.7403	Intermediate Similarity	NPD6492	Phase 2
0.7398	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7935	Phase 2
0.7377	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7222	Phase 2
0.7358	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5596	Phase 2
0.7348	Intermediate Similarity	NPD750	Phase 2
0.7346	Intermediate Similarity	NPD3654	Approved
0.7337	Intermediate Similarity	NPD5899	Approved
0.7337	Intermediate Similarity	NPD6452	Discontinued
0.7337	Intermediate Similarity	NPD5897	Approved
0.7337	Intermediate Similarity	NPD5898	Approved
0.7337	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6159	Phase 2
0.731	Intermediate Similarity	NPD1683	Approved
0.7306	Intermediate Similarity	NPD4397	Phase 1
0.7302	Intermediate Similarity	NPD8063	Discontinued
0.7297	Intermediate Similarity	NPD4203	Approved
0.7297	Intermediate Similarity	NPD4204	Approved
0.7283	Intermediate Similarity	NPD4079	Approved
0.7283	Intermediate Similarity	NPD8386	Phase 2
0.7283	Intermediate Similarity	NPD4076	Approved
0.7273	Intermediate Similarity	NPD5555	Phase 1
0.7268	Intermediate Similarity	NPD5100	Phase 3
0.7267	Intermediate Similarity	NPD4547	Phase 3
0.7259	Intermediate Similarity	NPD8114	Approved
0.7259	Intermediate Similarity	NPD8115	Approved
0.7258	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7112	Discontinued
0.7238	Intermediate Similarity	NPD1325	Approved
0.7238	Intermediate Similarity	NPD1326	Approved
0.7236	Intermediate Similarity	NPD7665	Phase 2
0.7236	Intermediate Similarity	NPD7666	Phase 3
0.7228	Intermediate Similarity	NPD3506	Approved
0.7228	Intermediate Similarity	NPD3505	Approved
0.7225	Intermediate Similarity	NPD6978	Phase 2
0.7225	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6455	Phase 3
0.7219	Intermediate Similarity	NPD4957	Phase 2
0.7216	Intermediate Similarity	NPD6026	Approved
0.7216	Intermediate Similarity	NPD7778	Approved
0.7216	Intermediate Similarity	NPD53	Approved
0.7216	Intermediate Similarity	NPD7777	Approved
0.7213	Intermediate Similarity	NPD5065	Approved
0.7212	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4499	Approved
0.7211	Intermediate Similarity	NPD6281	Approved
0.7209	Intermediate Similarity	NPD7469	Discontinued
0.7204	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8431	Approved
0.7184	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3082	Discontinued
0.7173	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5913	Phase 3
0.7168	Intermediate Similarity	NPD1661	Suspended
0.7159	Intermediate Similarity	NPD6285	Phase 2
0.7158	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7418	Discontinued
0.7158	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7474	Suspended
0.7143	Intermediate Similarity	NPD6554	Approved
0.7143	Intermediate Similarity	NPD45	Approved
0.7136	Intermediate Similarity	NPD3003	Approved
0.7136	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7194	Discontinued
0.7136	Intermediate Similarity	NPD7001	Phase 3
0.7135	Intermediate Similarity	NPD3525	Discontinued
0.7135	Intermediate Similarity	NPD3717	Discontinued
0.7135	Intermediate Similarity	NPD4047	Discontinued
0.7135	Intermediate Similarity	NPD2144	Approved
0.7135	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5138	Approved
0.7111	Intermediate Similarity	NPD5140	Approved
0.7107	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7452	Approved
0.71	Intermediate Similarity	NPD7453	Approved
0.7094	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2175	Phase 3
0.7092	Intermediate Similarity	NPD6248	Phase 2
0.7092	Intermediate Similarity	NPD2176	Approved
0.7092	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2177	Approved
0.7092	Intermediate Similarity	NPD6249	Phase 2
0.709	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD8272	Phase 2
0.7083	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6206	Phase 1
0.7074	Intermediate Similarity	NPD2095	Phase 2
0.7074	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2094	Phase 2
0.7074	Intermediate Similarity	NPD2092	Phase 2
0.7068	Intermediate Similarity	NPD4334	Discontinued
0.7062	Intermediate Similarity	NPD4427	Phase 2
0.705	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7957	Phase 1
0.7047	Intermediate Similarity	NPD6619	Phase 3
0.7041	Intermediate Similarity	NPD6261	Phase 3
0.7037	Intermediate Similarity	NPD2091	Phase 2
0.7037	Intermediate Similarity	NPD7483	Phase 2
0.7037	Intermediate Similarity	NPD2096	Phase 2
0.7037	Intermediate Similarity	NPD7482	Phase 2
0.7027	Intermediate Similarity	NPD482	Approved
0.7021	Intermediate Similarity	NPD3038	Discontinued
0.702	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD8322	Phase 2
0.7005	Intermediate Similarity	NPD6999	Discontinued
0.7005	Intermediate Similarity	NPD1768	Approved
0.7005	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7824	Approved
0.6989	Remote Similarity	NPD4463	Approved
0.6989	Remote Similarity	NPD4462	Approved
0.6989	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD2581	Approved
0.6983	Remote Similarity	NPD2582	Approved
0.698	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5020	Approved
0.6967	Remote Similarity	NPD7271	Approved
0.6965	Remote Similarity	NPD5530	Phase 1
0.6963	Remote Similarity	NPD5444	Phase 1
0.6959	Remote Similarity	NPD6569	Phase 2
0.6957	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3230	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