NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	493.25
Volume:	492.244
LogP:	2.809
LogD:	3.061
LogS:	-4.391
# Rotatable Bonds:	5
TPSA:	88.46
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	10
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	7.547
Fsp3:	0.69
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.247
MDCK Permeability:	1.539142249384895e-05
Pgp-inhibitor:	0.666
Pgp-substrate:	0.748
Human Intestinal Absorption (HIA):	0.196
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.925

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12
Plasma Protein Binding (PPB):	87.40534210205078%
Volume Distribution (VD):	1.34
Pgp-substrate:	13.289861679077148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.112
CYP2C9-substrate:	0.156
CYP2D6-inhibitor:	0.329
CYP2D6-substrate:	0.459
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.869

ADMET: Excretion

Clearance (CL):	8.414
Half-life (T1/2):	0.308

ADMET: Toxicity

hERG Blockers:	0.564
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.32
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.846
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.092
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC476500

Natural Product ID:	NPC476500
*Common Name:**	[(1R,5R,9R,11R,13R,16S,17R,18S,19S)-16,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-13-yl] 3,4-dimethoxybenzoate
IUPAC Name:	[(1R,5R,9R,11R,13R,16S,17R,18S,19S)-16,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-13-yl] 3,4-dimethoxybenzoate
Synonyms:	15-Veratroylpseudokobusine
Standard InCHIKey:	UGFXGERAVXLFDK-QLRGOLNFSA-N
Standard InCHI:	InChI=1S/C29H35NO6/c1-14-16-11-17-22-27-9-5-8-26(2)13-30(22)29(33,25(26)27)12-28(17,21(27)20(16)31)23(14)36-24(32)15-6-7-18(34-3)19(10-15)35-4/h6-7,10,16-17,20-23,25,31,33H,1,5,8-9,11-13H2,2-4H3/t16-,17+,20+,21+,22?,23-,25-,26+,27+,28?,29+/m1/s1
SMILES:	C[C@@]12CCC[C@]34[C@@H]1[C@]5(CC67[C@H]3[C@H]([C@H](C[C@H]6C4N5C2)C(=C)[C@H]7OC(=O)C8=CC(=C(C=C8)OC)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44445683
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003401] Villanovane, atisane, trachylobane or helvifulvane diterpenoids [CHEMONTID:0002738] Atisane diterpenoids

*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
NPO33634.1	Aconitum yesoense var. macroyesoense	Under-species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[18044843]

☑ 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

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	970000	nM	PMID[18044843]
NPT2	Others	Unspecified		IC50	=	2.9	ug/ml	PMID[18044843]

☑ 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 NPC476500 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	339
0.1-0.2	1426
0.2-0.3	3277
0.3-0.4	8231
0.4-0.5	11350
0.5-0.6	12889
0.6-0.7	4890
0.7-0.8	258
0.8-0.85	29
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8821	High Similarity	NPC476496
0.8673	High Similarity	NPC106840
0.8673	High Similarity	NPC476495
0.8673	High Similarity	NPC94687
0.8622	High Similarity	NPC326895
0.8205	Intermediate Similarity	NPC33256
0.8103	Intermediate Similarity	NPC172769
0.8103	Intermediate Similarity	NPC124690
0.8103	Intermediate Similarity	NPC205
0.8103	Intermediate Similarity	NPC184195
0.8103	Intermediate Similarity	NPC166521
0.8103	Intermediate Similarity	NPC281470
0.8095	Intermediate Similarity	NPC35680
0.8083	Intermediate Similarity	NPC162694
0.801	Intermediate Similarity	NPC94499
0.7979	Intermediate Similarity	NPC200726
0.7959	Intermediate Similarity	NPC108276
0.7959	Intermediate Similarity	NPC163578
0.7949	Intermediate Similarity	NPC141440
0.7938	Intermediate Similarity	NPC214629
0.7937	Intermediate Similarity	NPC177362
0.7908	Intermediate Similarity	NPC40539
0.7895	Intermediate Similarity	NPC202428
0.7895	Intermediate Similarity	NPC266545
0.7889	Intermediate Similarity	NPC66909
0.7876	Intermediate Similarity	NPC115906
0.7871	Intermediate Similarity	NPC67346
0.7861	Intermediate Similarity	NPC35345
0.7843	Intermediate Similarity	NPC80472
0.7822	Intermediate Similarity	NPC311781
0.7784	Intermediate Similarity	NPC473562
0.7783	Intermediate Similarity	NPC140577
0.7783	Intermediate Similarity	NPC97086
0.7783	Intermediate Similarity	NPC43069
0.7716	Intermediate Similarity	NPC230098
0.7696	Intermediate Similarity	NPC232533
0.7696	Intermediate Similarity	NPC286135
0.7662	Intermediate Similarity	NPC174783
0.7647	Intermediate Similarity	NPC64576
0.7647	Intermediate Similarity	NPC254045
0.7647	Intermediate Similarity	NPC201055
0.7647	Intermediate Similarity	NPC151470
0.7617	Intermediate Similarity	NPC329992
0.761	Intermediate Similarity	NPC243483
0.7606	Intermediate Similarity	NPC26353
0.7604	Intermediate Similarity	NPC476436
0.7602	Intermediate Similarity	NPC298339
0.7602	Intermediate Similarity	NPC160113
0.7602	Intermediate Similarity	NPC476220
0.759	Intermediate Similarity	NPC475197
0.759	Intermediate Similarity	NPC473467
0.759	Intermediate Similarity	NPC329816
0.7586	Intermediate Similarity	NPC83019
0.7574	Intermediate Similarity	NPC470646
0.7568	Intermediate Similarity	NPC154922
0.7565	Intermediate Similarity	NPC227683
0.7551	Intermediate Similarity	NPC474745
0.7548	Intermediate Similarity	NPC157958
0.7538	Intermediate Similarity	NPC473776
0.7538	Intermediate Similarity	NPC473205
0.7537	Intermediate Similarity	NPC204580
0.7524	Intermediate Similarity	NPC244191
0.7513	Intermediate Similarity	NPC305847
0.7513	Intermediate Similarity	NPC475780
0.7512	Intermediate Similarity	NPC72788
0.7512	Intermediate Similarity	NPC226652
0.7512	Intermediate Similarity	NPC120671
0.7512	Intermediate Similarity	NPC314100
0.75	Intermediate Similarity	NPC215098
0.75	Intermediate Similarity	NPC294790
0.75	Intermediate Similarity	NPC124302
0.75	Intermediate Similarity	NPC46744
0.75	Intermediate Similarity	NPC73020
0.75	Intermediate Similarity	NPC474325
0.75	Intermediate Similarity	NPC118633
0.75	Intermediate Similarity	NPC70290
0.75	Intermediate Similarity	NPC14622
0.75	Intermediate Similarity	NPC148693
0.7487	Intermediate Similarity	NPC188217
0.7487	Intermediate Similarity	NPC472803
0.7487	Intermediate Similarity	NPC304675
0.7476	Intermediate Similarity	NPC46990
0.7475	Intermediate Similarity	NPC302449
0.7475	Intermediate Similarity	NPC229234
0.7467	Intermediate Similarity	NPC476258
0.7467	Intermediate Similarity	NPC304837
0.7464	Intermediate Similarity	NPC11708
0.7462	Intermediate Similarity	NPC469438
0.7451	Intermediate Similarity	NPC475713
0.7451	Intermediate Similarity	NPC474432
0.7449	Intermediate Similarity	NPC474470
0.7449	Intermediate Similarity	NPC237044
0.7448	Intermediate Similarity	NPC474858
0.7447	Intermediate Similarity	NPC62051
0.7437	Intermediate Similarity	NPC474746
0.7437	Intermediate Similarity	NPC475981
0.7437	Intermediate Similarity	NPC475566
0.7433	Intermediate Similarity	NPC48671
0.7432	Intermediate Similarity	NPC476429
0.7427	Intermediate Similarity	NPC474427
0.7426	Intermediate Similarity	NPC226708
0.7426	Intermediate Similarity	NPC196231
0.7423	Intermediate Similarity	NPC474708
0.7416	Intermediate Similarity	NPC126211
0.7401	Intermediate Similarity	NPC113455
0.7394	Intermediate Similarity	NPC205392
0.7394	Intermediate Similarity	NPC105942
0.738	Intermediate Similarity	NPC261659
0.7376	Intermediate Similarity	NPC299855
0.7376	Intermediate Similarity	NPC96194
0.7374	Intermediate Similarity	NPC99179
0.7374	Intermediate Similarity	NPC475244
0.7371	Intermediate Similarity	NPC310572
0.7371	Intermediate Similarity	NPC475845
0.7366	Intermediate Similarity	NPC279665
0.7366	Intermediate Similarity	NPC279442
0.736	Intermediate Similarity	NPC241704
0.736	Intermediate Similarity	NPC148185
0.7358	Intermediate Similarity	NPC124657
0.7356	Intermediate Similarity	NPC202771
0.7356	Intermediate Similarity	NPC328700
0.7356	Intermediate Similarity	NPC119818
0.7356	Intermediate Similarity	NPC2173
0.7354	Intermediate Similarity	NPC323443
0.7354	Intermediate Similarity	NPC180756
0.734	Intermediate Similarity	NPC124842
0.734	Intermediate Similarity	NPC189704
0.7337	Intermediate Similarity	NPC469397
0.7326	Intermediate Similarity	NPC474305
0.732	Intermediate Similarity	NPC100420
0.732	Intermediate Similarity	NPC474324
0.732	Intermediate Similarity	NPC57812
0.731	Intermediate Similarity	NPC329969
0.7304	Intermediate Similarity	NPC475121
0.7304	Intermediate Similarity	NPC476067
0.7304	Intermediate Similarity	NPC120239
0.73	Intermediate Similarity	NPC248642
0.7295	Intermediate Similarity	NPC207239
0.7291	Intermediate Similarity	NPC470642
0.7286	Intermediate Similarity	NPC32154
0.7273	Intermediate Similarity	NPC474306
0.7273	Intermediate Similarity	NPC475848
0.7269	Intermediate Similarity	NPC38964
0.7264	Intermediate Similarity	NPC156576
0.7259	Intermediate Similarity	NPC475237
0.7259	Intermediate Similarity	NPC475641
0.7258	Intermediate Similarity	NPC214239
0.7256	Intermediate Similarity	NPC315253
0.7254	Intermediate Similarity	NPC218614
0.7254	Intermediate Similarity	NPC471003
0.7251	Intermediate Similarity	NPC314946
0.7245	Intermediate Similarity	NPC311991
0.724	Intermediate Similarity	NPC84349
0.724	Intermediate Similarity	NPC4304
0.7235	Intermediate Similarity	NPC473837
0.7231	Intermediate Similarity	NPC252960
0.7231	Intermediate Similarity	NPC120012
0.7228	Intermediate Similarity	NPC18306
0.7217	Intermediate Similarity	NPC258128
0.7214	Intermediate Similarity	NPC260300
0.7214	Intermediate Similarity	NPC275132
0.7208	Intermediate Similarity	NPC470739
0.7208	Intermediate Similarity	NPC118086
0.7208	Intermediate Similarity	NPC477640
0.7208	Intermediate Similarity	NPC225597
0.7204	Intermediate Similarity	NPC169605
0.7202	Intermediate Similarity	NPC68619
0.7202	Intermediate Similarity	NPC82056
0.72	Intermediate Similarity	NPC126284
0.72	Intermediate Similarity	NPC220961
0.72	Intermediate Similarity	NPC469354
0.7198	Intermediate Similarity	NPC475299
0.7196	Intermediate Similarity	NPC118033
0.7196	Intermediate Similarity	NPC119252
0.7194	Intermediate Similarity	NPC290759
0.7194	Intermediate Similarity	NPC158148
0.7194	Intermediate Similarity	NPC266176
0.7194	Intermediate Similarity	NPC470324
0.7194	Intermediate Similarity	NPC82533
0.719	Intermediate Similarity	NPC475747
0.7188	Intermediate Similarity	NPC7059
0.7188	Intermediate Similarity	NPC118804
0.7184	Intermediate Similarity	NPC230670
0.7184	Intermediate Similarity	NPC71385
0.7181	Intermediate Similarity	NPC253591
0.7179	Intermediate Similarity	NPC329717
0.7178	Intermediate Similarity	NPC93685
0.7178	Intermediate Similarity	NPC108191
0.7171	Intermediate Similarity	NPC63152
0.7171	Intermediate Similarity	NPC319549
0.717	Intermediate Similarity	NPC475768
0.7165	Intermediate Similarity	NPC320104
0.7165	Intermediate Similarity	NPC79571
0.7163	Intermediate Similarity	NPC293624
0.7163	Intermediate Similarity	NPC476358
0.7158	Intermediate Similarity	NPC121615
0.7158	Intermediate Similarity	NPC294511
0.7158	Intermediate Similarity	NPC267091
0.7158	Intermediate Similarity	NPC475579
0.7158	Intermediate Similarity	NPC473773

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 NPC476500 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	666
0.2-0.3	1380
0.3-0.4	2582
0.4-0.5	2684
0.5-0.6	1289
0.6-0.7	285
0.7-0.8	42
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
0.8854	High Similarity	NPD7497	Discontinued
0.795	Intermediate Similarity	NPD4107	Approved
0.7889	Intermediate Similarity	NPD2974	Approved
0.7889	Intermediate Similarity	NPD2973	Approved
0.7889	Intermediate Similarity	NPD2975	Approved
0.7876	Intermediate Similarity	NPD2968	Approved
0.7876	Intermediate Similarity	NPD2971	Approved
0.7871	Intermediate Similarity	NPD3057	Approved
0.7861	Intermediate Similarity	NPD4580	Approved
0.7831	Intermediate Similarity	NPD4481	Phase 3
0.7822	Intermediate Similarity	NPD4482	Phase 3
0.7819	Intermediate Similarity	NPD3051	Approved
0.7817	Intermediate Similarity	NPD2488	Approved
0.7817	Intermediate Similarity	NPD2490	Approved
0.7783	Intermediate Similarity	NPD3533	Approved
0.7783	Intermediate Similarity	NPD2972	Approved
0.7734	Intermediate Similarity	NPD2493	Approved
0.7734	Intermediate Similarity	NPD2494	Approved
0.7717	Intermediate Similarity	NPD6385	Approved
0.7717	Intermediate Similarity	NPD6386	Approved
0.771	Intermediate Similarity	NPD6997	Phase 2
0.7707	Intermediate Similarity	NPD4583	Approved
0.7707	Intermediate Similarity	NPD4582	Approved
0.7696	Intermediate Similarity	NPD2491	Approved
0.7684	Intermediate Similarity	NPD2970	Approved
0.7684	Intermediate Similarity	NPD2969	Approved
0.7674	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD4004	Approved
0.7659	Intermediate Similarity	NPD4002	Approved
0.7656	Intermediate Similarity	NPD5676	Approved
0.7647	Intermediate Similarity	NPD3452	Approved
0.7647	Intermediate Similarity	NPD3450	Approved
0.761	Intermediate Similarity	NPD3448	Approved
0.7602	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7047	Phase 3
0.757	Intermediate Similarity	NPD4111	Phase 1
0.757	Intermediate Similarity	NPD4665	Approved
0.7552	Intermediate Similarity	NPD27	Approved
0.7552	Intermediate Similarity	NPD2489	Approved
0.7513	Intermediate Similarity	NPD7310	Approved
0.7513	Intermediate Similarity	NPD7311	Approved
0.7513	Intermediate Similarity	NPD7312	Approved
0.7513	Intermediate Similarity	NPD7313	Approved
0.75	Intermediate Similarity	NPD4420	Approved
0.75	Intermediate Similarity	NPD7907	Approved
0.7488	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4663	Approved
0.7487	Intermediate Similarity	NPD8127	Discontinued
0.7475	Intermediate Similarity	NPD7309	Approved
0.745	Intermediate Similarity	NPD7906	Approved
0.7395	Intermediate Similarity	NPD5980	Discovery
0.7356	Intermediate Similarity	NPD5006	Approved
0.7356	Intermediate Similarity	NPD5005	Approved
0.7337	Intermediate Similarity	NPD4577	Approved
0.7337	Intermediate Similarity	NPD4578	Approved
0.7323	Intermediate Similarity	NPD7039	Approved
0.7323	Intermediate Similarity	NPD7038	Approved
0.7316	Intermediate Similarity	NPD5978	Approved
0.7316	Intermediate Similarity	NPD5977	Approved
0.73	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4040	Phase 1
0.7225	Intermediate Similarity	NPD5353	Approved
0.7194	Intermediate Similarity	NPD2898	Approved
0.7178	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7296	Approved
0.7158	Intermediate Similarity	NPD6873	Phase 2
0.7149	Intermediate Similarity	NPD7048	Phase 3
0.7121	Intermediate Similarity	NPD7177	Discontinued
0.7103	Intermediate Similarity	NPD7701	Phase 2
0.7092	Intermediate Similarity	NPD7315	Approved
0.7085	Intermediate Similarity	NPD5844	Phase 1
0.7062	Intermediate Similarity	NPD7833	Phase 2
0.7062	Intermediate Similarity	NPD7831	Phase 2
0.7062	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5242	Approved
0.7039	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7549	Discontinued
0.703	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6273	Approved
0.697	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7228	Approved
0.6943	Remote Similarity	NPD6844	Discontinued
0.6934	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7999	Approved
0.6923	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD4965	Approved
0.6923	Remote Similarity	NPD4967	Phase 2
0.6912	Remote Similarity	NPD7281	Phase 3
0.6912	Remote Similarity	NPD7280	Phase 3
0.6897	Remote Similarity	NPD7685	Pre-registration
0.6895	Remote Similarity	NPD7827	Phase 1
0.6891	Remote Similarity	NPD6677	Suspended
0.6887	Remote Similarity	NPD8285	Discontinued
0.6884	Remote Similarity	NPD8319	Approved
0.6884	Remote Similarity	NPD8320	Phase 1
0.6872	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5241	Discontinued
0.686	Remote Similarity	NPD7291	Discontinued
0.6856	Remote Similarity	NPD7577	Discontinued
0.6845	Remote Similarity	NPD4236	Phase 3
0.6845	Remote Similarity	NPD4237	Approved
0.6834	Remote Similarity	NPD5710	Approved
0.6834	Remote Similarity	NPD5711	Approved
0.6834	Remote Similarity	NPD6071	Discontinued
0.6833	Remote Similarity	NPD7930	Approved
0.6832	Remote Similarity	NPD5312	Approved
0.6832	Remote Similarity	NPD5313	Approved
0.6827	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6666	Approved
0.6825	Remote Similarity	NPD6667	Approved
0.6821	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5494	Approved
0.6814	Remote Similarity	NPD7240	Approved
0.6809	Remote Similarity	NPD4628	Phase 3
0.6809	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4110	Phase 3
0.6808	Remote Similarity	NPD7565	Approved
0.6808	Remote Similarity	NPD7810	Phase 3
0.6808	Remote Similarity	NPD7811	Phase 3
0.6804	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7874	Approved
0.6804	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7110	Phase 1
0.6802	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6625	Approved
0.6796	Remote Similarity	NPD6853	Approved
0.6796	Remote Similarity	NPD6851	Approved
0.6789	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7458	Discontinued
0.6788	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6107	Approved
0.6784	Remote Similarity	NPD7199	Phase 2
0.6776	Remote Similarity	NPD6782	Approved
0.6776	Remote Similarity	NPD6776	Approved
0.6776	Remote Similarity	NPD6779	Approved
0.6776	Remote Similarity	NPD6777	Approved
0.6776	Remote Similarity	NPD6778	Approved
0.6776	Remote Similarity	NPD6781	Approved
0.6776	Remote Similarity	NPD6780	Approved
0.6774	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD7783	Phase 2
0.6773	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD3640	Phase 3
0.6771	Remote Similarity	NPD3641	Approved
0.6771	Remote Similarity	NPD3639	Approved
0.6771	Remote Similarity	NPD8404	Phase 2
0.6771	Remote Similarity	NPD7427	Discontinued
0.6769	Remote Similarity	NPD37	Approved
0.6768	Remote Similarity	NPD6234	Discontinued
0.6759	Remote Similarity	NPD7697	Approved
0.6759	Remote Similarity	NPD7698	Approved
0.6759	Remote Similarity	NPD7696	Phase 3
0.6758	Remote Similarity	NPD8151	Discontinued
0.6753	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4210	Discontinued
0.6735	Remote Similarity	NPD5772	Approved
0.6735	Remote Similarity	NPD5773	Approved
0.6733	Remote Similarity	NPD7473	Discontinued
0.6728	Remote Similarity	NPD7870	Phase 2
0.6728	Remote Similarity	NPD7871	Phase 2
0.6718	Remote Similarity	NPD4772	Phase 2
0.6718	Remote Similarity	NPD4773	Phase 2
0.6701	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD2560	Approved
0.6701	Remote Similarity	NPD2563	Approved
0.6698	Remote Similarity	NPD4363	Phase 3
0.6698	Remote Similarity	NPD4360	Phase 2
0.6697	Remote Similarity	NPD7801	Approved
0.6697	Remote Similarity	NPD8161	Suspended
0.6685	Remote Similarity	NPD3110	Approved
0.6685	Remote Similarity	NPD3109	Approved
0.6684	Remote Similarity	NPD1670	Discontinued
0.6684	Remote Similarity	NPD4727	Phase 1
0.6684	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6297	Approved
0.6682	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD8156	Discontinued
0.6667	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4361	Phase 2
0.6667	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8059	Phase 3
0.6652	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6212	Phase 3
0.6651	Remote Similarity	NPD6213	Phase 3
0.6651	Remote Similarity	NPD8434	Phase 2
0.6651	Remote Similarity	NPD8150	Discontinued
0.665	Remote Similarity	NPD5760	Phase 2
0.665	Remote Similarity	NPD5761	Phase 2
0.6649	Remote Similarity	NPD3687	Approved
0.6649	Remote Similarity	NPD3686	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