NPASS Compound

Natural Product: NPC45210

Natural Product ID	NPC45210
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QRBQBRULJDJSSP-XTPLGFNASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102117122
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 103108 0 0 0 0 0 0 0 0999 V2000 1.5465 -3.7928 -2.4008 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1973 -2.4235 -2.4160 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9420 -2.4169 -3.7768 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2972 -2.4049 -1.4087 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6930 -2.3154 -0.0512 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0528 -0.9541 0.0827 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3946 -0.7218 1.3853 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0427 -0.9226 1.5968 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9259 -0.8156 0.3113 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0646 -2.2630 -0.0608 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0466 -0.0108 -0.5446 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3963 1.2192 -0.8352 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6490 1.7758 -0.3124 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6814 2.9849 0.0207 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7324 0.8075 -0.2470 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0956 1.3746 -0.0464 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3613 2.1527 1.1609 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2898 2.3379 -1.2410 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6638 2.8730 -1.3595 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7860 2.0083 -0.9656 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4769 0.6231 -0.5500 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0659 -0.3291 -1.6139 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2491 0.2222 0.7113 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0607 0.2667 -0.3858 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7869 -0.8781 0.5298 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3922 -1.3819 0.2699 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3029 -0.3397 0.5911 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4324 -0.1308 2.0804 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5008 2.6175 0.0975 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7983 3.3096 -2.7064 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2504 -0.4867 -1.0952 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2220 -1.2876 -2.3259 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0672 -1.7048 -2.7396 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3348 -0.1074 0.1734 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5866 0.7658 -0.6619 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 -0.3392 1.2120 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3933 0.3750 1.3740 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3745 1.2558 2.6191 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4947 2.2645 2.4318 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6047 1.7021 1.6059 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6840 0.2135 1.5704 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2987 -0.3771 2.8277 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5373 -1.7344 2.6360 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5013 -0.4298 1.3080 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6159 2.2011 0.2985 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9136 2.8192 3.6294 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1362 1.9383 2.5670 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5440 -3.6815 -2.8725 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4247 -4.2162 -1.4052 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0851 -4.5320 -3.0562 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2177 -2.4703 -4.5976 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6470 -3.2652 -3.7246 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5411 -1.4773 -3.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0041 -1.5556 -1.5291 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8271 -3.3778 -1.4778 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0271 -3.1596 0.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4973 -2.3612 0.7334 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9402 -1.3973 2.1232 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7210 0.3023 1.7684 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3379 -0.1107 2.3197 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2384 -1.8576 2.1358 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1592 -2.8038 -0.3010 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3931 -2.7558 0.9129 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8024 -2.5451 -0.7890 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2504 1.8839 -1.4694 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8402 0.3561 -1.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4012 2.5511 1.5615 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9392 3.1041 0.9423 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9067 1.6979 1.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5881 3.1715 -1.2270 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0240 1.7203 -2.1411 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6924 3.8507 -0.7884 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5456 2.0194 -1.8062 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1369 -0.4707 -1.4584 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4846 -1.2621 -1.6504 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9111 0.2121 -2.5826 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0658 -0.8451 0.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1207 0.9080 1.5397 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3476 0.2620 0.4447 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6859 -0.0873 -1.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4336 -1.7283 0.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1169 -0.7943 1.5483 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2921 -2.3147 0.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 -1.4308 -0.8634 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5058 -0.1599 2.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0539 -1.0534 2.5769 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0518 0.8113 2.4611 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4597 2.3720 0.0649 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3514 4.1227 -2.7613 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8223 0.4515 -1.4354 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4690 -0.6678 -3.2594 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6096 -0.8879 -2.9829 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4634 1.1157 0.5230 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4326 0.7007 3.5540 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0481 3.1044 1.8206 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5671 2.0674 2.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3853 -0.0488 0.7236 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6087 -0.3021 3.6926 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2479 0.1755 3.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8571 -2.1292 2.0661 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9256 3.1285 0.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9263 3.8095 3.5855 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9994 2.3104 1.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 20 29 1 0 19 30 1 0 11 31 1 0 31 32 1 0 32 33 1 0 6 34 1 1 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 32 2 1 0 44 37 1 0 31 6 1 0 27 9 1 0 27 15 1 0 24 16 1 0 1 48 1 0 1 49 1 0 1 50 1 0 3 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 10 62 1 0 10 63 1 0 10 64 1 0 12 65 1 0 15 66 1 6 17 67 1 0 17 68 1 0 17 69 1 0 18 70 1 0 18 71 1 0 19 72 1 1 20 73 1 6 22 74 1 0 22 75 1 0 22 76 1 0 23 77 1 0 23 78 1 0 23 79 1 0 24 80 1 6 25 81 1 0 25 82 1 0 26 83 1 0 26 84 1 0 28 85 1 0 28 86 1 0 28 87 1 0 29 88 1 0 30 89 1 0 31 90 1 6 32 91 1 6 33 92 1 0 37 93 1 6 38 94 1 1 39 95 1 6 40 96 1 1 41 97 1 6 42 98 1 0 42 99 1 0 43100 1 0 45101 1 0 46102 1 0 47103 1 0 M END

Standard InCHIKey	QRBQBRULJDJSSP-XTPLGFNASA-N
Standard InCHI	InChI=1S/C36H56O11/c1-31(2)10-12-36(30(45)47-29-25(42)24(41)23(40)20(16-37)46-29)13-11-34(6)17(22(36)28(31)44)14-18(38)26-33(5)15-19(39)27(43)32(3,4)21(33)8-9-35(26,34)7/h14,19-29,37,39-44H,8-13,15-16H2,1-7H3/t19-,20-,21+,22-,23-,24+,25-,26-,27+,28+,29+,33+,34-,35-,36+/m1/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC(=O)[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@@H]1O)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	664.38	Volume:	668.656 ? Van der Waals volume.
Dense:	0.994	LogP:	1.335 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.844 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.828 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	34.0
TPSA:	194.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.217	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.553	Fsp³:	0.889
MCE-18:	135.294 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.775	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.278 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.113	Promiscuous compounds:	0.318

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.889	MDCK Permeability:	-5.042
Pgp-inhibitor:	0.0	Pgp-substrate:	0.173
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.542
20% Bioavailability (F20%):	0.925	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.695	MRP1:	0.471
Plasma Protein Binding (PPB):	76.616%	Volume Distribution (VD):	-0.19
Fu:	17.098% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.005
BSEP inhibitor:	0.148

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.936
HLM stability:	0.641 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.848

Half-life (T1/2):

2.712

ADMET: Toxicity

hERG Blockers:	0.015	hERG Blockers (10um):	0.029
Human Hepatotoxicity (H-HT):	0.782	Drug-induced Liver Injury (DILI):	0.719
AMES Toxicity:	0.856	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.045	Skin Sensitization:	0.999
Carcinogencity:	0.466	Eye Corrosion:	0.0
Eye Irritation:	0.024	Respiratory Toxicity:	0.029
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.981
Hematotoxicity:	0.66	Drug-induced Nephrotoxicity:	0.991
Genotoxicity:	0.441	RPMI-8226 Immunitoxicity:	0.124
A549 Cytotoxicity:	0.462	Hek293 Cytotoxicity:	0.154
BCF:	0.634 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.459 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.246 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.351 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26650	Terminalia chebula	Species	Combretaceae	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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC45210 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	20557
0.1-0.2	24015
0.2-0.3	4545
0.3-0.4	595
0.4-0.5	119
0.5-0.6	17
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8816	High Similarity	NPC187056
0.8816	High Similarity	NPC606216
0.8816	High Similarity	NPC607023
0.7722	Intermediate Similarity	NPC605954
0.6786	Remote Similarity	NPC116794
0.6506	Remote Similarity	NPC191763
0.6437	Remote Similarity	NPC7870
0.6437	Remote Similarity	NPC75747
0.625	Remote Similarity	NPC310014
0.625	Remote Similarity	NPC269315
0.5699	Remote Similarity	NPC128925
0.5699	Remote Similarity	NPC256798
0.5652	Remote Similarity	NPC102914
0.5604	Remote Similarity	NPC65590
0.5604	Remote Similarity	NPC125923
0.5543	Remote Similarity	NPC68419
0.5484	Remote Similarity	NPC271138
0.5484	Remote Similarity	NPC110139
0.5484	Remote Similarity	NPC108709
0.5437	Remote Similarity	NPC473401
0.5426	Remote Similarity	NPC220984
0.5294	Remote Similarity	NPC161674
0.5275	Remote Similarity	NPC167383
0.5217	Remote Similarity	NPC46388
0.5106	Remote Similarity	NPC199457
0.5094	Remote Similarity	NPC148417
0.5053	Remote Similarity	NPC604133

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC45210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7263
0.1-0.2	1772
0.2-0.3	106
0.3-0.4	9
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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