NPASS Compound

Structure

NPC180306 OpenBabel07101718182D 26 29 0 0 1 0 0 0 0 0999 V2000 1.2708 -3.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9400 -2.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 11 2 0 0 0 0 8 9 1 0 0 0 0 8 11 1 0 0 0 0 9 21 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 12 16 1 0 0 0 0 13 7 1 6 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 12 1 6 0 0 0 15 17 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 11 1 1 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	361.19
Volume:	364.652
LogP:	1.951
LogD:	2.524
LogS:	-2.404
# Rotatable Bonds:	4
TPSA:	49.39
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.769
Synthetic Accessibility Score:	4.283
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:	-4.639
MDCK Permeability:	2.6742778572952375e-05
Pgp-inhibitor:	0.538
Pgp-substrate:	0.053
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	62.997650146484375%
Volume Distribution (VD):	1.897
Pgp-substrate:	25.94666862487793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.95
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.445
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.846
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	9.493
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.322
Drug-inuced Liver Injury (DILI):	0.125
AMES Toxicity:	0.363
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.117
Carcinogencity:	0.839
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC180306

Natural Product ID:	NPC180306
*Common Name:**	(+)-O-Methylnerinine
IUPAC Name:	(5aR,7S,11bS,11cS)-7,8,9,10-tetramethoxy-1-methyl-3,5,5a,7,11b,11c-hexahydro-2H-isochromeno[3,4-g]indole
Synonyms:	(+)-O-Methylnerinine
Standard InCHIKey:	LPEKOSCSUJGQQB-PCFVDWANSA-N
Standard InCHI:	InChI=1S/C20H27NO5/c1-21-9-8-11-6-7-13-15(17(11)21)12-10-14(22-2)18(23-3)19(24-4)16(12)20(25-5)26-13/h6,10,13,15,17,20H,7-9H2,1-5H3/t13-,15-,17-,20+/m1/s1
SMILES:	CO[C@H]1O[C@@H]2CC=C3[C@H]([C@@H]2c2c1c(OC)c(c(c2)OC)OC)N(C)CC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208205
PubChem CID:	71459807
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004122] Homolycorine-type amaryllidaceae 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
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	whole plants	n.a.	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2348199]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26913788]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[561842]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[561842]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[561842]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[561842]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[561842]

☑ 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 NPC180306 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	305
0.1-0.2	1455
0.2-0.3	4901
0.3-0.4	12441
0.4-0.5	6571
0.5-0.6	11075
0.6-0.7	4539
0.7-0.8	1273
0.8-0.85	106
0.85-0.9	27
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9172	High Similarity	NPC4304
0.9012	High Similarity	NPC75958
0.8773	High Similarity	NPC474324
0.8773	High Similarity	NPC57812
0.872	High Similarity	NPC475845
0.869	High Similarity	NPC244554
0.8667	High Similarity	NPC474708
0.8614	High Similarity	NPC19520
0.8614	High Similarity	NPC149090
0.8614	High Similarity	NPC65403
0.8596	High Similarity	NPC9867
0.8589	High Similarity	NPC218614
0.8589	High Similarity	NPC320104
0.8545	High Similarity	NPC181653
0.8545	High Similarity	NPC190332
0.8545	High Similarity	NPC252960
0.8535	High Similarity	NPC37144
0.8535	High Similarity	NPC59907
0.8512	High Similarity	NPC304675
0.8462	Intermediate Similarity	NPC237044
0.8434	Intermediate Similarity	NPC100566
0.8412	Intermediate Similarity	NPC474325
0.8402	Intermediate Similarity	NPC187678
0.8363	Intermediate Similarity	NPC258695
0.8363	Intermediate Similarity	NPC474745
0.8363	Intermediate Similarity	NPC470879
0.8333	Intermediate Similarity	NPC78733
0.8324	Intermediate Similarity	NPC475981
0.8324	Intermediate Similarity	NPC474746
0.8323	Intermediate Similarity	NPC247389
0.8314	Intermediate Similarity	NPC474506
0.8314	Intermediate Similarity	NPC32413
0.8313	Intermediate Similarity	NPC167546
0.8313	Intermediate Similarity	NPC302527
0.8313	Intermediate Similarity	NPC16805
0.8304	Intermediate Similarity	NPC15919
0.8304	Intermediate Similarity	NPC118633
0.8304	Intermediate Similarity	NPC148693
0.8304	Intermediate Similarity	NPC294790
0.8284	Intermediate Similarity	NPC225597
0.8284	Intermediate Similarity	NPC470739
0.8284	Intermediate Similarity	NPC477640
0.8282	Intermediate Similarity	NPC146288
0.8282	Intermediate Similarity	NPC323443
0.8282	Intermediate Similarity	NPC180756
0.8274	Intermediate Similarity	NPC266176
0.8274	Intermediate Similarity	NPC290759
0.8274	Intermediate Similarity	NPC82533
0.8274	Intermediate Similarity	NPC158148
0.8266	Intermediate Similarity	NPC299990
0.8266	Intermediate Similarity	NPC73492
0.8263	Intermediate Similarity	NPC476002
0.8263	Intermediate Similarity	NPC219341
0.8263	Intermediate Similarity	NPC24264
0.8263	Intermediate Similarity	NPC476432
0.8251	Intermediate Similarity	NPC80472
0.8242	Intermediate Similarity	NPC205167
0.8242	Intermediate Similarity	NPC249274
0.8235	Intermediate Similarity	NPC2314
0.8229	Intermediate Similarity	NPC214116
0.8225	Intermediate Similarity	NPC474475
0.8225	Intermediate Similarity	NPC311991
0.8221	Intermediate Similarity	NPC41178
0.8221	Intermediate Similarity	NPC138487
0.8221	Intermediate Similarity	NPC216459
0.8214	Intermediate Similarity	NPC210918
0.821	Intermediate Similarity	NPC148898
0.8204	Intermediate Similarity	NPC225774
0.8204	Intermediate Similarity	NPC247972
0.8198	Intermediate Similarity	NPC23219
0.8187	Intermediate Similarity	NPC475959
0.8187	Intermediate Similarity	NPC49353
0.8166	Intermediate Similarity	NPC58766
0.8166	Intermediate Similarity	NPC182257
0.8166	Intermediate Similarity	NPC475686
0.814	Intermediate Similarity	NPC112575
0.814	Intermediate Similarity	NPC474470
0.814	Intermediate Similarity	NPC35680
0.8137	Intermediate Similarity	NPC211296
0.8125	Intermediate Similarity	NPC57036
0.8125	Intermediate Similarity	NPC230098
0.809	Intermediate Similarity	NPC63152
0.8061	Intermediate Similarity	NPC31311
0.8061	Intermediate Similarity	NPC234392
0.8057	Intermediate Similarity	NPC248642
0.8046	Intermediate Similarity	NPC99179
0.8034	Intermediate Similarity	NPC281581
0.8034	Intermediate Similarity	NPC82763
0.8024	Intermediate Similarity	NPC306902
0.8024	Intermediate Similarity	NPC97072
0.8024	Intermediate Similarity	NPC232924
0.8024	Intermediate Similarity	NPC266753
0.8024	Intermediate Similarity	NPC477559
0.8024	Intermediate Similarity	NPC160298
0.8024	Intermediate Similarity	NPC215829
0.8012	Intermediate Similarity	NPC6152
0.8011	Intermediate Similarity	NPC156576
0.7989	Intermediate Similarity	NPC475597
0.7989	Intermediate Similarity	NPC114364
0.7989	Intermediate Similarity	NPC473716
0.7989	Intermediate Similarity	NPC320223
0.7988	Intermediate Similarity	NPC24465
0.7988	Intermediate Similarity	NPC233029
0.7988	Intermediate Similarity	NPC210148
0.7978	Intermediate Similarity	NPC476576
0.7978	Intermediate Similarity	NPC186546
0.7977	Intermediate Similarity	NPC128560
0.7977	Intermediate Similarity	NPC229166
0.7977	Intermediate Similarity	NPC199465
0.7964	Intermediate Similarity	NPC477080
0.7962	Intermediate Similarity	NPC196420
0.7956	Intermediate Similarity	NPC33256
0.7955	Intermediate Similarity	NPC275132
0.7953	Intermediate Similarity	NPC204908
0.7953	Intermediate Similarity	NPC83198
0.795	Intermediate Similarity	NPC473934
0.7944	Intermediate Similarity	NPC24260
0.7944	Intermediate Similarity	NPC117717
0.7943	Intermediate Similarity	NPC126284
0.7941	Intermediate Similarity	NPC264850
0.7941	Intermediate Similarity	NPC124657
0.7941	Intermediate Similarity	NPC13916
0.7921	Intermediate Similarity	NPC474661
0.7921	Intermediate Similarity	NPC475919
0.7919	Intermediate Similarity	NPC152680
0.7919	Intermediate Similarity	NPC190783
0.7919	Intermediate Similarity	NPC110374
0.7919	Intermediate Similarity	NPC289743
0.7919	Intermediate Similarity	NPC232386
0.7907	Intermediate Similarity	NPC474953
0.7904	Intermediate Similarity	NPC476572
0.7895	Intermediate Similarity	NPC204947
0.7892	Intermediate Similarity	NPC328700
0.7892	Intermediate Similarity	NPC202771
0.7892	Intermediate Similarity	NPC2173
0.7892	Intermediate Similarity	NPC99659
0.7892	Intermediate Similarity	NPC119818
0.7892	Intermediate Similarity	NPC93593
0.7892	Intermediate Similarity	NPC244112
0.7892	Intermediate Similarity	NPC325871
0.7888	Intermediate Similarity	NPC145304
0.7888	Intermediate Similarity	NPC130926
0.7882	Intermediate Similarity	NPC231198
0.7882	Intermediate Similarity	NPC276944
0.7882	Intermediate Similarity	NPC238530
0.7882	Intermediate Similarity	NPC232514
0.7877	Intermediate Similarity	NPC237579
0.7866	Intermediate Similarity	NPC223125
0.7862	Intermediate Similarity	NPC216434
0.7862	Intermediate Similarity	NPC103448
0.7861	Intermediate Similarity	NPC239775
0.7861	Intermediate Similarity	NPC276890
0.7861	Intermediate Similarity	NPC227060
0.7861	Intermediate Similarity	NPC76682
0.7861	Intermediate Similarity	NPC198498
0.7861	Intermediate Similarity	NPC10908
0.7861	Intermediate Similarity	NPC63646
0.7861	Intermediate Similarity	NPC115284
0.7861	Intermediate Similarity	NPC317145
0.7861	Intermediate Similarity	NPC317439
0.7857	Intermediate Similarity	NPC69360
0.7857	Intermediate Similarity	NPC59028
0.7857	Intermediate Similarity	NPC92191
0.7853	Intermediate Similarity	NPC7467
0.7841	Intermediate Similarity	NPC267408
0.7834	Intermediate Similarity	NPC7018
0.7829	Intermediate Similarity	NPC283999
0.7829	Intermediate Similarity	NPC115343
0.7829	Intermediate Similarity	NPC1291
0.7829	Intermediate Similarity	NPC293093
0.7821	Intermediate Similarity	NPC162694
0.7818	Intermediate Similarity	NPC474560
0.7818	Intermediate Similarity	NPC218575
0.7816	Intermediate Similarity	NPC129518
0.7816	Intermediate Similarity	NPC228040
0.7816	Intermediate Similarity	NPC251580
0.7816	Intermediate Similarity	NPC41376
0.7816	Intermediate Similarity	NPC12424
0.7797	Intermediate Similarity	NPC305847
0.7791	Intermediate Similarity	NPC106295
0.7791	Intermediate Similarity	NPC476144
0.7791	Intermediate Similarity	NPC51957
0.7791	Intermediate Similarity	NPC16107
0.7791	Intermediate Similarity	NPC210437
0.7791	Intermediate Similarity	NPC298186
0.7791	Intermediate Similarity	NPC298979
0.7791	Intermediate Similarity	NPC301189
0.779	Intermediate Similarity	NPC475754
0.7784	Intermediate Similarity	NPC123323
0.7778	Intermediate Similarity	NPC141440
0.7771	Intermediate Similarity	NPC256776
0.7771	Intermediate Similarity	NPC145722
0.7771	Intermediate Similarity	NPC223124
0.7771	Intermediate Similarity	NPC11147
0.7771	Intermediate Similarity	NPC185680
0.7764	Intermediate Similarity	NPC474295
0.7764	Intermediate Similarity	NPC80326
0.7759	Intermediate Similarity	NPC10871
0.7759	Intermediate Similarity	NPC57272
0.7756	Intermediate Similarity	NPC65183

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 NPC180306 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	697
0.2-0.3	1168
0.3-0.4	2763
0.4-0.5	2342
0.5-0.6	1354
0.6-0.7	513
0.7-0.8	119
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
0.8166	Intermediate Similarity	NPD4481	Phase 3
0.8165	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2969	Approved
0.8	Intermediate Similarity	NPD2970	Approved
0.7941	Intermediate Similarity	NPD3051	Approved
0.7919	Intermediate Similarity	NPD8156	Discontinued
0.7892	Intermediate Similarity	NPD5005	Approved
0.7892	Intermediate Similarity	NPD5006	Approved
0.7861	Intermediate Similarity	NPD8252	Approved
0.7861	Intermediate Similarity	NPD8251	Approved
0.7861	Intermediate Similarity	NPD8099	Discontinued
0.7849	Intermediate Similarity	NPD27	Approved
0.7849	Intermediate Similarity	NPD2489	Approved
0.7797	Intermediate Similarity	NPD7313	Approved
0.7797	Intermediate Similarity	NPD7312	Approved
0.7797	Intermediate Similarity	NPD7310	Approved
0.7797	Intermediate Similarity	NPD7311	Approved
0.7791	Intermediate Similarity	NPD4584	Approved
0.7753	Intermediate Similarity	NPD7309	Approved
0.775	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7906	Approved
0.7716	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4577	Approved
0.7697	Intermediate Similarity	NPD4578	Approved
0.7692	Intermediate Similarity	NPD2563	Approved
0.7692	Intermediate Similarity	NPD2560	Approved
0.7679	Intermediate Similarity	NPD3384	Approved
0.7679	Intermediate Similarity	NPD3382	Approved
0.7679	Intermediate Similarity	NPD3383	Approved
0.7677	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD4420	Approved
0.7669	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7124	Phase 2
0.7667	Intermediate Similarity	NPD4663	Approved
0.7654	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4210	Discontinued
0.7647	Intermediate Similarity	NPD6788	Approved
0.763	Intermediate Similarity	NPD6071	Discontinued
0.7619	Intermediate Similarity	NPD4773	Phase 2
0.7619	Intermediate Similarity	NPD4772	Phase 2
0.7602	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4237	Approved
0.7593	Intermediate Similarity	NPD4236	Phase 3
0.7562	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8053	Approved
0.7556	Intermediate Similarity	NPD8054	Approved
0.7529	Intermediate Similarity	NPD4585	Approved
0.7529	Intermediate Similarity	NPD2978	Approved
0.7529	Intermediate Similarity	NPD5773	Approved
0.7529	Intermediate Similarity	NPD5772	Approved
0.7529	Intermediate Similarity	NPD2977	Approved
0.7527	Intermediate Similarity	NPD6843	Phase 3
0.7527	Intermediate Similarity	NPD6842	Approved
0.7527	Intermediate Similarity	NPD6841	Approved
0.75	Intermediate Similarity	NPD2971	Approved
0.75	Intermediate Similarity	NPD6111	Discontinued
0.75	Intermediate Similarity	NPD7296	Approved
0.75	Intermediate Similarity	NPD2968	Approved
0.75	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD4005	Discontinued
0.7471	Intermediate Similarity	NPD6107	Approved
0.747	Intermediate Similarity	NPD1424	Approved
0.7468	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5241	Discontinued
0.7391	Intermediate Similarity	NPD2200	Suspended
0.7381	Intermediate Similarity	NPD3641	Approved
0.7381	Intermediate Similarity	NPD3640	Phase 3
0.7381	Intermediate Similarity	NPD3639	Approved
0.734	Intermediate Similarity	NPD2975	Approved
0.734	Intermediate Similarity	NPD2974	Approved
0.734	Intermediate Similarity	NPD2973	Approved
0.7333	Intermediate Similarity	NPD7466	Approved
0.7333	Intermediate Similarity	NPD5754	Discontinued
0.7316	Intermediate Similarity	NPD4580	Approved
0.7312	Intermediate Similarity	NPD2238	Phase 2
0.731	Intermediate Similarity	NPD5090	Approved
0.731	Intermediate Similarity	NPD5089	Approved
0.7299	Intermediate Similarity	NPD4055	Discovery
0.7278	Intermediate Similarity	NPD4727	Phase 1
0.7278	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5177	Phase 3
0.7267	Intermediate Similarity	NPD37	Approved
0.7267	Intermediate Similarity	NPD7298	Approved
0.7262	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1375	Discontinued
0.7241	Intermediate Similarity	NPD4967	Phase 2
0.7241	Intermediate Similarity	NPD4966	Approved
0.7241	Intermediate Similarity	NPD4965	Approved
0.7225	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5312	Approved
0.7222	Intermediate Similarity	NPD5313	Approved
0.7219	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5297	Approved
0.7193	Intermediate Similarity	NPD4017	Approved
0.7188	Intermediate Similarity	NPD3452	Approved
0.7188	Intermediate Similarity	NPD2494	Approved
0.7188	Intermediate Similarity	NPD2493	Approved
0.7188	Intermediate Similarity	NPD5718	Phase 2
0.7188	Intermediate Similarity	NPD3450	Approved
0.7178	Intermediate Similarity	NPD6896	Approved
0.7178	Intermediate Similarity	NPD6895	Approved
0.7176	Intermediate Similarity	NPD6030	Approved
0.7176	Intermediate Similarity	NPD6031	Approved
0.7172	Intermediate Similarity	NPD7827	Phase 1
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7166	Intermediate Similarity	NPD2490	Approved
0.7166	Intermediate Similarity	NPD2488	Approved
0.7165	Intermediate Similarity	NPD4583	Approved
0.7165	Intermediate Similarity	NPD4582	Approved
0.7159	Intermediate Similarity	NPD6234	Discontinued
0.7158	Intermediate Similarity	NPD7549	Discontinued
0.7151	Intermediate Similarity	NPD2898	Approved
0.7151	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4107	Approved
0.7135	Intermediate Similarity	NPD4166	Phase 2
0.7134	Intermediate Similarity	NPD4108	Discontinued
0.7119	Intermediate Similarity	NPD5677	Discontinued
0.7117	Intermediate Similarity	NPD2492	Phase 1
0.7113	Intermediate Similarity	NPD4004	Approved
0.7113	Intermediate Similarity	NPD4002	Approved
0.7108	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3109	Approved
0.7099	Intermediate Similarity	NPD3110	Approved
0.7086	Intermediate Similarity	NPD5353	Approved
0.7083	Intermediate Similarity	NPD8095	Phase 1
0.7072	Intermediate Similarity	NPD7228	Approved
0.7052	Intermediate Similarity	NPD4675	Approved
0.7052	Intermediate Similarity	NPD4678	Approved
0.7027	Intermediate Similarity	NPD7281	Phase 3
0.7027	Intermediate Similarity	NPD7280	Phase 3
0.7024	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3489	Phase 3
0.701	Intermediate Similarity	NPD4482	Phase 3
0.7006	Intermediate Similarity	NPD7831	Phase 2
0.7006	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5604	Discontinued
0.7006	Intermediate Similarity	NPD7833	Phase 2
0.7	Intermediate Similarity	NPD5242	Approved
0.6982	Remote Similarity	NPD2677	Approved
0.6977	Remote Similarity	NPD5976	Discontinued
0.6973	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6625	Approved
0.6964	Remote Similarity	NPD4162	Approved
0.6964	Remote Similarity	NPD3060	Approved
0.6941	Remote Similarity	NPD6667	Approved
0.6941	Remote Similarity	NPD6666	Approved
0.6935	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4475	Approved
0.6933	Remote Similarity	NPD4474	Approved
0.6931	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1753	Discontinued
0.6927	Remote Similarity	NPD5582	Discontinued
0.6927	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6331	Phase 2
0.6919	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7240	Approved
0.6919	Remote Similarity	NPD7526	Approved
0.6919	Remote Similarity	NPD52	Approved
0.6914	Remote Similarity	NPD6386	Approved
0.6914	Remote Similarity	NPD6385	Approved
0.6908	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1774	Approved
0.6901	Remote Similarity	NPD3124	Discontinued
0.6901	Remote Similarity	NPD7213	Phase 3
0.6901	Remote Similarity	NPD7212	Phase 2
0.6897	Remote Similarity	NPD7047	Phase 3
0.6889	Remote Similarity	NPD7199	Phase 2
0.6888	Remote Similarity	NPD3057	Approved
0.6886	Remote Similarity	NPD3454	Phase 3
0.6882	Remote Similarity	NPD3692	Discontinued
0.6882	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2122	Discontinued
0.6875	Remote Similarity	NPD4098	Discontinued
0.6872	Remote Similarity	NPD7400	Phase 3
0.6865	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7447	Phase 1
0.686	Remote Similarity	NPD3158	Phase 1
0.686	Remote Similarity	NPD3157	Approved
0.6851	Remote Similarity	NPD4010	Discontinued
0.6845	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3122	Phase 3
0.6839	Remote Similarity	NPD3686	Approved
0.6839	Remote Similarity	NPD3687	Approved
0.6833	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7110	Phase 1
0.6813	Remote Similarity	NPD6688	Approved
0.6813	Remote Similarity	NPD6687	Approved
0.6813	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3027	Phase 3
0.6807	Remote Similarity	NPD2653	Approved
0.6802	Remote Similarity	NPD3533	Approved
0.6802	Remote Similarity	NPD2972	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