NPASS Compound

Structure

NPC9867 OpenBabel07101718202D 25 30 0 0 1 0 0 0 0 0999 V2000 1.9400 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8004 -1.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8469 1.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5993 0.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2343 1.0462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4810 1.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2558 0.3264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5025 0.3638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8899 -0.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7065 -0.1392 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.9581 -1.1070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9199 -1.0143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1588 1.3264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1937 0.1618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 3.4781 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 4 1 0 0 0 0 4 19 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 11 1 0 0 0 0 7 23 1 0 0 0 0 7 24 1 0 0 0 0 8 12 1 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 21 1 6 0 0 0 10 13 2 0 0 0 0 10 23 1 0 0 0 0 11 18 1 1 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 1 0 0 0 15 22 1 0 0 0 0 16 18 1 1 0 0 0 16 25 1 0 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	347.14
Volume:	324.374
LogP:	0.886
LogD:	0.949
LogS:	-2.564
# Rotatable Bonds:	2
TPSA:	72.92
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.798
Synthetic Accessibility Score:	5.583
Fsp3:	0.667
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:	-5.206
MDCK Permeability:	2.9865523174521513e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.959
Plasma Protein Binding (PPB):	23.488508224487305%
Volume Distribution (VD):	1.214
Pgp-substrate:	59.60570526123047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.803
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.463
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.513
CYP3A4-inhibitor:	0.591
CYP3A4-substrate:	0.846

ADMET: Excretion

Clearance (CL):	6.837
Half-life (T1/2):	0.479

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.769
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.479
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.108
Carcinogencity:	0.524
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC9867

Natural Product ID:	NPC9867
*Common Name:**	MSOASAXKAHRWRY-GJEABJGOSA-N
IUPAC Name:	n.a.
Synonyms:	6Alpha-Hydroxyundulatine
Standard InCHIKey:	MSOASAXKAHRWRY-GJEABJGOSA-N
Standard InCHI:	InChI=1S/C18H21NO6/c1-21-9-6-11-18(16-14(9)25-16)3-4-19(11)17(20)12-8(18)5-10-13(15(12)22-2)24-7-23-10/h5,9,11,14,16-17,20H,3-4,6-7H2,1-2H3/t9-,11-,14+,16+,17-,18+/m1/s1
SMILES:	CO[C@@H]1C[C@@H]2[C@@]3(CCN2[C@@H](c2c3cc3c(c2OC)OCO3)O)[C@@H]2[C@H]1O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2146606
PubChem CID:	15479738
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004123] Crinine- and Haemanthamine-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
NPO33437	amaryllidaceae	Family	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22921081]

☑ 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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	25.0	%	PMID[547871]

☑ 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 NPC9867 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	344
0.1-0.2	1519
0.2-0.3	4511
0.3-0.4	11684
0.4-0.5	8008
0.5-0.6	11911
0.6-0.7	3901
0.7-0.8	721
0.8-0.85	73
0.85-0.9	20
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9464	High Similarity	NPC15919
0.9341	High Similarity	NPC65403
0.9181	High Similarity	NPC244554
0.9167	High Similarity	NPC311991
0.9053	High Similarity	NPC75958
0.9006	High Similarity	NPC187678
0.8889	High Similarity	NPC470739
0.8889	High Similarity	NPC225597
0.8889	High Similarity	NPC477640
0.883	High Similarity	NPC474475
0.8824	High Similarity	NPC100566
0.8772	High Similarity	NPC58766
0.8772	High Similarity	NPC266176
0.8772	High Similarity	NPC290759
0.8772	High Similarity	NPC158148
0.8772	High Similarity	NPC82533
0.8772	High Similarity	NPC475686
0.8713	High Similarity	NPC190332
0.8713	High Similarity	NPC181653
0.8686	High Similarity	NPC294790
0.8686	High Similarity	NPC148693
0.8686	High Similarity	NPC118633
0.8647	High Similarity	NPC320104
0.8639	High Similarity	NPC97072
0.8639	High Similarity	NPC215829
0.8629	High Similarity	NPC474470
0.8629	High Similarity	NPC237044
0.8621	High Similarity	NPC2314
0.8596	High Similarity	NPC180306
0.858	High Similarity	NPC474325
0.8571	High Similarity	NPC304675
0.8547	High Similarity	NPC476002
0.8531	High Similarity	NPC474745
0.85	High Similarity	NPC214116
0.8497	Intermediate Similarity	NPC252960
0.8492	Intermediate Similarity	NPC475981
0.8492	Intermediate Similarity	NPC474746
0.843	Intermediate Similarity	NPC218614
0.8421	Intermediate Similarity	NPC4304
0.8402	Intermediate Similarity	NPC78733
0.8391	Intermediate Similarity	NPC474324
0.8391	Intermediate Similarity	NPC57812
0.8352	Intermediate Similarity	NPC149090
0.8352	Intermediate Similarity	NPC19520
0.8343	Intermediate Similarity	NPC475845
0.8333	Intermediate Similarity	NPC275132
0.8333	Intermediate Similarity	NPC248642
0.8297	Intermediate Similarity	NPC230098
0.8297	Intermediate Similarity	NPC57036
0.8295	Intermediate Similarity	NPC474708
0.8287	Intermediate Similarity	NPC156576
0.8276	Intermediate Similarity	NPC24465
0.8276	Intermediate Similarity	NPC247972
0.8263	Intermediate Similarity	NPC37144
0.8263	Intermediate Similarity	NPC59907
0.8261	Intermediate Similarity	NPC63152
0.8239	Intermediate Similarity	NPC83198
0.8239	Intermediate Similarity	NPC204908
0.8229	Intermediate Similarity	NPC13916
0.8229	Intermediate Similarity	NPC264850
0.8222	Intermediate Similarity	NPC99179
0.8222	Intermediate Similarity	NPC126284
0.8216	Intermediate Similarity	NPC117717
0.8216	Intermediate Similarity	NPC24260
0.8208	Intermediate Similarity	NPC249274
0.8208	Intermediate Similarity	NPC205167
0.8207	Intermediate Similarity	NPC82763
0.8202	Intermediate Similarity	NPC152680
0.8202	Intermediate Similarity	NPC232386
0.8202	Intermediate Similarity	NPC190783
0.8187	Intermediate Similarity	NPC168250
0.8182	Intermediate Similarity	NPC210918
0.8171	Intermediate Similarity	NPC238530
0.8171	Intermediate Similarity	NPC276944
0.8171	Intermediate Similarity	NPC232514
0.8167	Intermediate Similarity	NPC114364
0.8167	Intermediate Similarity	NPC320223
0.8156	Intermediate Similarity	NPC128560
0.8156	Intermediate Similarity	NPC199465
0.8156	Intermediate Similarity	NPC49353
0.8156	Intermediate Similarity	NPC229166
0.8152	Intermediate Similarity	NPC186546
0.8152	Intermediate Similarity	NPC476576
0.814	Intermediate Similarity	NPC147091
0.814	Intermediate Similarity	NPC31311
0.814	Intermediate Similarity	NPC234392
0.8132	Intermediate Similarity	NPC299990
0.8132	Intermediate Similarity	NPC73492
0.8122	Intermediate Similarity	NPC470879
0.8122	Intermediate Similarity	NPC258695
0.8092	Intermediate Similarity	NPC129603
0.8081	Intermediate Similarity	NPC216459
0.8081	Intermediate Similarity	NPC41178
0.8081	Intermediate Similarity	NPC138487
0.8079	Intermediate Similarity	NPC247389
0.8077	Intermediate Similarity	NPC32413
0.8077	Intermediate Similarity	NPC474506
0.807	Intermediate Similarity	NPC233029
0.807	Intermediate Similarity	NPC210148
0.8068	Intermediate Similarity	NPC167546
0.8068	Intermediate Similarity	NPC16805
0.8068	Intermediate Similarity	NPC302527
0.8066	Intermediate Similarity	NPC23219
0.8047	Intermediate Similarity	NPC475959
0.8046	Intermediate Similarity	NPC59028
0.8046	Intermediate Similarity	NPC92191
0.8046	Intermediate Similarity	NPC111485
0.8045	Intermediate Similarity	NPC239775
0.8035	Intermediate Similarity	NPC146288
0.8031	Intermediate Similarity	NPC80472
0.8023	Intermediate Similarity	NPC219341
0.8023	Intermediate Similarity	NPC476432
0.8023	Intermediate Similarity	NPC24264
0.8011	Intermediate Similarity	NPC283999
0.8	Intermediate Similarity	NPC228040
0.8	Intermediate Similarity	NPC110374
0.8	Intermediate Similarity	NPC289743
0.7989	Intermediate Similarity	NPC315707
0.7989	Intermediate Similarity	NPC40389
0.7989	Intermediate Similarity	NPC148014
0.7989	Intermediate Similarity	NPC65490
0.7989	Intermediate Similarity	NPC78359
0.7978	Intermediate Similarity	NPC298979
0.7969	Intermediate Similarity	NPC2173
0.7969	Intermediate Similarity	NPC202771
0.7969	Intermediate Similarity	NPC119818
0.7969	Intermediate Similarity	NPC328700
0.7966	Intermediate Similarity	NPC225774
0.7965	Intermediate Similarity	NPC148898
0.7958	Intermediate Similarity	NPC475654
0.7943	Intermediate Similarity	NPC477080
0.7935	Intermediate Similarity	NPC116284
0.7933	Intermediate Similarity	NPC182257
0.7921	Intermediate Similarity	NPC124657
0.7914	Intermediate Similarity	NPC281581
0.7912	Intermediate Similarity	NPC115343
0.7912	Intermediate Similarity	NPC1291
0.7912	Intermediate Similarity	NPC112575
0.791	Intermediate Similarity	NPC108826
0.7903	Intermediate Similarity	NPC475919
0.7903	Intermediate Similarity	NPC474661
0.7892	Intermediate Similarity	NPC135772
0.7889	Intermediate Similarity	NPC168753
0.7889	Intermediate Similarity	NPC118274
0.7882	Intermediate Similarity	NPC476151
0.788	Intermediate Similarity	NPC155442
0.788	Intermediate Similarity	NPC477561
0.788	Intermediate Similarity	NPC476574
0.788	Intermediate Similarity	NPC312918
0.7877	Intermediate Similarity	NPC150879
0.7872	Intermediate Similarity	NPC475754
0.7872	Intermediate Similarity	NPC475597
0.7872	Intermediate Similarity	NPC473716
0.7861	Intermediate Similarity	NPC223124
0.7849	Intermediate Similarity	NPC16357
0.7849	Intermediate Similarity	NPC95426
0.7849	Intermediate Similarity	NPC274026
0.7849	Intermediate Similarity	NPC302245
0.7842	Intermediate Similarity	NPC162653
0.7838	Intermediate Similarity	NPC217748
0.7838	Intermediate Similarity	NPC233718
0.7838	Intermediate Similarity	NPC104196
0.7838	Intermediate Similarity	NPC222661
0.7838	Intermediate Similarity	NPC290005
0.7838	Intermediate Similarity	NPC185639
0.7838	Intermediate Similarity	NPC311973
0.7838	Intermediate Similarity	NPC476575
0.7838	Intermediate Similarity	NPC42663
0.7838	Intermediate Similarity	NPC223690
0.7838	Intermediate Similarity	NPC15414
0.7838	Intermediate Similarity	NPC285931
0.7838	Intermediate Similarity	NPC328155
0.7838	Intermediate Similarity	NPC49075
0.7838	Intermediate Similarity	NPC182052
0.7838	Intermediate Similarity	NPC181796
0.7838	Intermediate Similarity	NPC229373
0.7838	Intermediate Similarity	NPC90998
0.7838	Intermediate Similarity	NPC258657
0.7838	Intermediate Similarity	NPC271013
0.7838	Intermediate Similarity	NPC54654
0.7838	Intermediate Similarity	NPC251735
0.7838	Intermediate Similarity	NPC290582
0.7838	Intermediate Similarity	NPC279228
0.7838	Intermediate Similarity	NPC8836
0.7838	Intermediate Similarity	NPC239824
0.7838	Intermediate Similarity	NPC7715
0.7829	Intermediate Similarity	NPC323443
0.7829	Intermediate Similarity	NPC180756
0.7814	Intermediate Similarity	NPC241704
0.7807	Intermediate Similarity	NPC116465
0.7807	Intermediate Similarity	NPC212237
0.7807	Intermediate Similarity	NPC65312
0.7807	Intermediate Similarity	NPC139783
0.7797	Intermediate Similarity	NPC266753
0.7797	Intermediate Similarity	NPC18402
0.7797	Intermediate Similarity	NPC165797
0.7797	Intermediate Similarity	NPC232924
0.7797	Intermediate Similarity	NPC160298
0.7797	Intermediate Similarity	NPC477559
0.7797	Intermediate Similarity	NPC306902

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 NPC9867 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	671
0.2-0.3	1085
0.3-0.4	2766
0.4-0.5	2465
0.5-0.6	1470
0.6-0.7	390
0.7-0.8	98
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8023	Intermediate Similarity	NPD6071	Discontinued
0.7989	Intermediate Similarity	NPD2560	Approved
0.7989	Intermediate Similarity	NPD2563	Approved
0.7978	Intermediate Similarity	NPD2969	Approved
0.7978	Intermediate Similarity	NPD2970	Approved
0.7969	Intermediate Similarity	NPD5005	Approved
0.7969	Intermediate Similarity	NPD5006	Approved
0.7921	Intermediate Similarity	NPD3051	Approved
0.7838	Intermediate Similarity	NPD8053	Approved
0.7838	Intermediate Similarity	NPD8054	Approved
0.7833	Intermediate Similarity	NPD2489	Approved
0.7833	Intermediate Similarity	NPD27	Approved
0.7807	Intermediate Similarity	NPD7906	Approved
0.7802	Intermediate Similarity	NPD8156	Discontinued
0.7784	Intermediate Similarity	NPD7311	Approved
0.7784	Intermediate Similarity	NPD4577	Approved
0.7784	Intermediate Similarity	NPD4578	Approved
0.7784	Intermediate Similarity	NPD7312	Approved
0.7784	Intermediate Similarity	NPD7310	Approved
0.7784	Intermediate Similarity	NPD7313	Approved
0.776	Intermediate Similarity	NPD4420	Approved
0.7754	Intermediate Similarity	NPD4663	Approved
0.7747	Intermediate Similarity	NPD8099	Discontinued
0.7747	Intermediate Similarity	NPD8251	Approved
0.7747	Intermediate Similarity	NPD8252	Approved
0.7742	Intermediate Similarity	NPD7309	Approved
0.7714	Intermediate Similarity	NPD4773	Phase 2
0.7714	Intermediate Similarity	NPD4772	Phase 2
0.7674	Intermediate Similarity	NPD4584	Approved
0.7637	Intermediate Similarity	NPD4481	Phase 3
0.7633	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6788	Approved
0.7528	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD5582	Discontinued
0.746	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD2978	Approved
0.743	Intermediate Similarity	NPD2977	Approved
0.7399	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4237	Approved
0.7384	Intermediate Similarity	NPD4236	Phase 3
0.736	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2898	Approved
0.7347	Intermediate Similarity	NPD2973	Approved
0.7347	Intermediate Similarity	NPD2974	Approved
0.7347	Intermediate Similarity	NPD2975	Approved
0.7333	Intermediate Similarity	NPD5773	Approved
0.7333	Intermediate Similarity	NPD5772	Approved
0.7323	Intermediate Similarity	NPD4580	Approved
0.732	Intermediate Similarity	NPD7296	Approved
0.7308	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4005	Discontinued
0.7299	Intermediate Similarity	NPD5241	Discontinued
0.7286	Intermediate Similarity	NPD6997	Phase 2
0.7286	Intermediate Similarity	NPD2494	Approved
0.7286	Intermediate Similarity	NPD3450	Approved
0.7286	Intermediate Similarity	NPD3452	Approved
0.7286	Intermediate Similarity	NPD2493	Approved
0.7283	Intermediate Similarity	NPD5177	Phase 3
0.7273	Intermediate Similarity	NPD1424	Approved
0.7268	Intermediate Similarity	NPD7827	Phase 1
0.7264	Intermediate Similarity	NPD4583	Approved
0.7264	Intermediate Similarity	NPD4582	Approved
0.7257	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7047	Phase 3
0.7225	Intermediate Similarity	NPD7281	Phase 3
0.7225	Intermediate Similarity	NPD7280	Phase 3
0.7222	Intermediate Similarity	NPD6625	Approved
0.7214	Intermediate Similarity	NPD4002	Approved
0.7214	Intermediate Similarity	NPD4004	Approved
0.7213	Intermediate Similarity	NPD7831	Phase 2
0.7213	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4055	Discovery
0.7213	Intermediate Similarity	NPD7833	Phase 2
0.7189	Intermediate Similarity	NPD6107	Approved
0.7179	Intermediate Similarity	NPD2488	Approved
0.7179	Intermediate Similarity	NPD2490	Approved
0.7165	Intermediate Similarity	NPD6841	Approved
0.7165	Intermediate Similarity	NPD6843	Phase 3
0.7165	Intermediate Similarity	NPD6842	Approved
0.7159	Intermediate Similarity	NPD7124	Phase 2
0.7158	Intermediate Similarity	NPD4966	Approved
0.7158	Intermediate Similarity	NPD4965	Approved
0.7158	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD4010	Discontinued
0.7135	Intermediate Similarity	NPD2971	Approved
0.7135	Intermediate Similarity	NPD2968	Approved
0.712	Intermediate Similarity	NPD5604	Discontinued
0.7118	Intermediate Similarity	NPD2238	Phase 2
0.7111	Intermediate Similarity	NPD4017	Approved
0.7111	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3639	Approved
0.7095	Intermediate Similarity	NPD3640	Phase 3
0.7095	Intermediate Similarity	NPD6030	Approved
0.7095	Intermediate Similarity	NPD3641	Approved
0.7095	Intermediate Similarity	NPD6031	Approved
0.7088	Intermediate Similarity	NPD3382	Approved
0.7088	Intermediate Similarity	NPD3384	Approved
0.7088	Intermediate Similarity	NPD7298	Approved
0.7088	Intermediate Similarity	NPD3383	Approved
0.7083	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7549	Discontinued
0.7079	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4678	Approved
0.7072	Intermediate Similarity	NPD4675	Approved
0.7043	Intermediate Similarity	NPD5677	Discontinued
0.7043	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD8095	Phase 1
0.6995	Remote Similarity	NPD37	Approved
0.6989	Remote Similarity	NPD6234	Discontinued
0.6979	Remote Similarity	NPD7007	Discovery
0.6963	Remote Similarity	NPD5312	Approved
0.6963	Remote Similarity	NPD5313	Approved
0.6961	Remote Similarity	NPD4210	Discontinued
0.6954	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4040	Phase 1
0.6911	Remote Similarity	NPD7228	Approved
0.6897	Remote Similarity	NPD6111	Discontinued
0.6893	Remote Similarity	NPD3060	Approved
0.6878	Remote Similarity	NPD4166	Phase 2
0.6865	Remote Similarity	NPD4585	Approved
0.6857	Remote Similarity	NPD1753	Discontinued
0.6848	Remote Similarity	NPD5090	Approved
0.6848	Remote Similarity	NPD5089	Approved
0.6837	Remote Similarity	NPD6851	Approved
0.6837	Remote Similarity	NPD6853	Approved
0.6834	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2421	Approved
0.6833	Remote Similarity	NPD6723	Discontinued
0.6833	Remote Similarity	NPD7212	Phase 2
0.6833	Remote Similarity	NPD2420	Approved
0.6833	Remote Similarity	NPD7213	Phase 3
0.6829	Remote Similarity	NPD3057	Approved
0.6816	Remote Similarity	NPD2677	Approved
0.6813	Remote Similarity	NPD4727	Phase 1
0.6811	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6297	Approved
0.68	Remote Similarity	NPD2200	Suspended
0.6796	Remote Similarity	NPD7447	Phase 1
0.6796	Remote Similarity	NPD4123	Phase 3
0.6791	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1375	Discontinued
0.6776	Remote Similarity	NPD3686	Approved
0.6776	Remote Similarity	NPD3687	Approved
0.6774	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3705	Approved
0.6766	Remote Similarity	NPD7125	Discontinued
0.6763	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6090	Discontinued
0.6757	Remote Similarity	NPD6072	Discontinued
0.6754	Remote Similarity	NPD5242	Approved
0.6754	Remote Similarity	NPD6688	Approved
0.6754	Remote Similarity	NPD6687	Approved
0.6748	Remote Similarity	NPD3533	Approved
0.6748	Remote Similarity	NPD2972	Approved
0.6744	Remote Similarity	NPD4111	Phase 1
0.6744	Remote Similarity	NPD3027	Phase 3
0.6741	Remote Similarity	NPD7048	Phase 3
0.6739	Remote Similarity	NPD8153	Approved
0.6739	Remote Similarity	NPD8152	Approved
0.6737	Remote Similarity	NPD7199	Phase 2
0.6735	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1613	Approved
0.6722	Remote Similarity	NPD3692	Discontinued
0.6721	Remote Similarity	NPD5976	Discontinued
0.6715	Remote Similarity	NPD7497	Discontinued
0.6705	Remote Similarity	NPD5718	Phase 2
0.6705	Remote Similarity	NPD6896	Approved
0.6705	Remote Similarity	NPD6895	Approved
0.6704	Remote Similarity	NPD6674	Discontinued
0.6704	Remote Similarity	NPD4162	Approved
0.6703	Remote Similarity	NPD7019	Approved
0.6703	Remote Similarity	NPD7020	Approved
0.6703	Remote Similarity	NPD3158	Phase 1
0.6703	Remote Similarity	NPD3157	Approved
0.67	Remote Similarity	NPD2843	Phase 2
0.67	Remote Similarity	NPD2845	Phase 2
0.6686	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6667	Approved
0.6685	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6666	Approved
0.6684	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7240	Approved
0.6682	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD2491	Approved
0.6667	Remote Similarity	NPD3448	Approved
0.6667	Remote Similarity	NPD4475	Approved
0.6667	Remote Similarity	NPD4474	Approved
0.6667	Remote Similarity	NPD4665	Approved
0.6667	Remote Similarity	NPD7466	Approved
0.6667	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7526	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